Jacobie is the founder of C2G Advisors and brokered the landmark Vacasa and Casago deal. He walks through EBITDA, multiples, take rate, churn, and the real steps to turn a small management business into something worth millions. If you have ever thought about selling your rental business one day, this is the playbook for what to build toward now.

TIMESTAMPS

00:00 Meet the man who brokers STR company sales

00:25 What C2G does and the size of deals they run

02:25 Inside the Vacasa and Casago deal

09:10 Why big money is moving into a fragmented industry

10:32 The state of the market and why the next few years favor sellers

13:30 How companies are valued by size (the multiple ladder)

16:00 Why smaller deals pay you less cash up front

17:56 Turning a lifestyle business into a sellable asset

21:00 The magic number that opens the door to real buyers

24:35 Can you sell on co-host contracts instead of full management?

26:35 Mike Reilly asks: how do I acquire another company?

32:45 The KPIs that actually drive your valuation

41:12 The fee trick that quietly raises your take rate

42:45 Where the whole industry is headed next

Want the KPI scorecard from this episode? DM @strsecrets on Instagram.

Learn more about C2G Advisors: https://c2gadvisors.com

Connect with Jacobie: jacobie@c2gadvisors.com

Subscribe for new episodes every Monday.

#ShortTermRentals #PropertyManagement #AirbnbHost #VacationRentals #STRSecrets #RealEstateInvesting #BusinessExit #MergersAndAcquisitions

The next software. The next tech company. The next shiny object.

Jason Muth did the opposite. And it built him a 53-unit business in about two years.

In this episode, Jason joins the show to break down how he grew Prideaway Stays from his first client in April 2024 to 53 properties under management, with zero acquisitions and 100 percent organic growth.

No buying other companies. No chasing every new tactic. Just one market, one avatar, and a relentless focus most operators are too distracted to hold.

In this episode:

→ Why Jason picked one town, went all in, and refused to look at a single other market

→ The organic growth engine behind 53 units, from handwritten direct mail to referrals from cleaners and owners

→ How he walked away from a career at some of the biggest media companies in the country and became the go-to short-term rental expert in his market

→ The delegation moment on a cruise that finally forced him to stop doing everything himself

→ How he educates owners with simple monthly videos and real data, and why that consistency builds trust that closes deals

→ Why the market has shifted, how property values doubled while revenue did not, and what that means for owners today

→ His number one secret to success: make big decisions fast, and stop chasing shiny objects

If you feel overwhelmed by every new tool and tactic in this space, this episode is the reset you need.

About Jason:

Jason Muth left W-2 life in 2022, after his real estate side hustle became more profitable than his corporate career at companies like Comcast, NBCUniversal, and iHeartMedia. He is the founder of Prideaway Stays, a boutique, gay-owned, tech-driven co-hosting business in Provincetown, MA, and the owner of Straightforward Short-Term Rentals in Massachusetts and New Hampshire. He also hosts the SmartStay Show.

Connect with Jason:

Instagram: @prideawaystays

Podcast: SmartStay Show, on YouTube, Spotify, and Apple Podcasts

Free 6-step course to start your day right: level.strsecrets.com/pc-book

In this episode, we sat down with Cam to walk through the whole acquisition, start to finish. He bought a 40 year old management company, one started by a founder of Vrbo, and he shares the exact moves that got it done.

Inside this episode:

How Cam went from 18 units to 140 plus by buying one company

Why he skipped the bank and used seller financing plus a friends and family raise

How he and his partner put in just 30 percent and got the seller to carry the rest

The 10,000 dollar move that can save you from a 1 million dollar mistake

The 35,000 dollar cost he forgot to check, and how it bit him after closing

The room full of bigger operators that made him stop thinking small

If you have ever felt like real growth is out of reach, this one will change how you think about what is possible.

Want to be in the room with operators doing deals like this? Check out the STR Secrets Mastermind: strsecrets.com/apply

Connect with Cameron Masters on Instagram: @cameron.masters_

New episodes every Monday.

Connect with Mike Reilly : https://www.instagram.com/mikereillync/

Most operators think busy season is the worst time to look for new properties. Mike Reilly just signed 7 new contracts that prove them wrong.

Last quarter his team at NC Stays reached out to 1,000 homeowners. They opened 68 real conversations. They signed 7 new properties, and 19 more deals are still on the table. And all of it started in the middle of peak season.

Why? Because of one thing most operators never check: the 90 day notice window. Most management contracts renew in the fall. If a homeowner wants to leave their property manager, they have to say so 90 days before the contract renews. So if you wait until September to start talking to owners, they're already stuck for another year.

In this 18 minute training, Mike walks through his COHOST funnel step by step:

C: Create awareness. A simple website, social posts, and a list of homes you want.

O: Open the conversation. Send a free 5 minute video showing the owner what they're missing. Don't ask for a meeting.

H: Hold the discovery call. This is where deals are really won, and where you filter out bad-fit owners.

O: Offer your solution.

S: Sign the contract. Including the $2,500 upgrade rule Mike puts in every contract.

T: Take over and onboard. This pairs with last week's onboarding episode.

Plus the story of a beach house owner losing $30,000 to $40,000 a year because his best photo was buried at spot #68 in his listing. And why it takes about 4.5 calls before an owner signs.

If you have no new leads right now, this episode shows you why. Save it.

Want the owner contact lists, the CRM, and a community of operators growing past 50 listings? Check out the STR Secrets Mastermind: [LINK]

New episodes every Monday.

Connect with Mike Reilly : https://www.instagram.com/mikereillync/

How do you onboard 7 vacation rental properties in one month without burning out your team?

Mike Reilly breaks down the exact 6 stage onboarding system NC Stays uses for every new property, from the first homeowner call to the post launch celebration.

Homeowner trust in property managers is at an all time low.

Nearly every owner has been burned before.

The managers who onboard properties with a real system are locking in 5 to 10 year relationships and standing out in a market flooded with new co-hosts.

In this training you'll learn the full checklist:

• Why the first 30 days with a homeowner decides the next 10 years
• The 6 stages of onboarding: Handoff, On-Site Setup, Photography, Listing & Software Setup, Final Touches, and Post Launch
• How Mike's team uses Meta glasses to capture every inch of a home and turn it into checklists automatically
• The QR code trick that eliminates guest questions about the grill, hot tub, sauna, and game room
• The exact roles to hire: project manager, contractor help, listing team, and data quality
• How one Pinehurst property pulled $30,000 in bookings from mood boards alone, before it was even ready
• The review stay strategy that gets Airbnb pushing your listing to page one in week one

TIMESTAMPS

00:00 Trailer

00:37 Welcome back + what's coming for the podcast

02:02 Onboarding 7 properties in one month (all 4,000+ sq ft)

03:59 The trust crisis and why onboarding is your biggest advantage

05:00 The system and the 6 roles you need on your team

07:58 The 6 stages of onboarding explained

08:01 Stage 1: The Handoff (welcome email, onboarding form, group text)

09:55 Stage 2: On-Site Setup with Meta glasses

11:12 QR codes, inventory counts, and the house manual

14:30 Stage 3: Photography (lifestyle shots, staging, shot lists)

15:35 Stage 4: Listing & Software Setup (custom GPT listings, PriceLabs)

16:55 $30,000 in bookings from mood boards before launch

17:36 Stage 5: Final Touches (data quality, review stays, financials)

19:07 Stage 6: Post Launch (social posts, email list, owner shareables)

20:02 Why you can't scale without this process

20:41 Inside the STR Secrets Mastermind

no idea.

In this episode, Mike Sjogren returns to the show with Mike Reilly. And they open with a

trend that changes everything.

In 2022, most short-term rentals in the US were run by hosts with fewer than 20 units. By 2025, that share had dropped hard. The reason is not that hosts quit. It is that private equity quietly started buying up management companies, because the margins are good and the industry is wide open.

Mike breaks down what that means for you, and reveals the project STR Secrets has spent 16 months building to help members cash in on it.

In this episode:

→ The data behind the great short-term rental consolidation, and why the big money is moving in now

→ Freedom Collective: the new vehicle built to help operators sell their management company for a 6 to 8X exit instead of a 3 to 5X

→ How 22 members generated over $3 million in new management commissions in about 7 weeks, including one who acquired a company and added 122 doors in a single quarter

→ The full AI Summit recap

→ Why the most important hire of the next few years is an AI mplementation specialist, and why the CEO's job is to cast the vision, not tinker in the tools until 3am

→ Mike's own Q2 numbers from the new AI-powered CRM: 1,000 leads, 68 opportunities, 7 new clients, and $211,000 in new commissions, while taking only 10 percent of the sales calls himself

Whether you have your first property or your fiftieth, this episode will change how you think about where this industry is headed.

Ready to scale and exit the right way? Apply to work with us: strsecrets.com/apply

300 episodes later, this is his last one.

In this final solo show, recorded from his grandparents' house in Sardinia, Emanuele Pani answers the same question this podcast has asked every guest for six years.

What is your number one secret to success?

Only this time, he answers it for himself.

E shares the 5 lessons that changed his life more than anything else.

The lessons that took him from chasing more information, more courses, and more outside validation, to the most peace, health, and happiness he has ever felt.

In this episode:

→ Why your identity, not your strategy, decides how far you go

→ The difference between goals and standards, and why standards are the ones that actually shape your future

→ How the story you tell about yourself becomes the life you live

→ Why every level of growth costs you the person you used to be

→ The inside-out truth about success that no system or strategy can replace

This is not a goodbye.

It is a thank you to a community that has spent six years in E's ears.

In your cars. In your kitchens. On your morning walks.

And it is a torch being passed.

Thank you for everything, E.

Free 6-step course to start your day right: level.strsecrets.com/pc-book

Join the community: STR Secrets Facebook Group

You can follow E's next chapter on his new show, CEO Mindset, available

now on Spotify and Apple Podcasts.

Open heart surgery patients. Life or death. No room for error.

And in the gaps between shifts, sometimes still in his scrubs, he was quietly building a short-term rental business that would set him free.

In this episode, E sits down with Jeremy Rosen for one of the most honest W2-escape stories this show has ever told.

Jeremy joined STR Secrets with 4 properties and a full-time nursing job he loved but knew he had to leave. He went from 4 to 8 to 12 to 20 properties, all while clocking 12-hour shifts at the VA. Then he merged his own company into Five Star Vacation Home Rentals, where he now owns the San Antonio division, part of a portfolio of 70 properties across Central Texas. And he finally walked away from nursing for good.

Today, based in San Antonio, Texas, Jeremy focuses on revenue optimization, guest experience, property operations, and scaling high performing vacation rental portfolios.

In this episode:

→ The exact mindset shift that took Jeremy from sick patients to happy guests, and the nurse's instinct that makes him a better host than most operators will ever be

→ How he used his days off, while everyone else scrolled, to prospect, sell, and grow

→ The "who not how" decision that broke him out of doing everything himself, and the one hire that changed his entire business

→ Why he refused to build in secret, and how speaking his goals out loud actually made them happen

→ The honest truth about quitting your W2 that almost nobody talks about, including the strange struggle of suddenly owning all of your own time

→ Why "everything is figureoutable" is the only belief you need to finally make the leap

If you have a good job you're scared to leave, this is the episode you need to hear.

Connect with Jeremy:

Instagram and Facebook: @fivestarvhr

Email: jeremy@fivestarvacationhomerentals.com

Website: fivestarvhr.com

Free 6-step course to start your day right: level.strsecrets.com/pc-book

Join the community: STR Secrets Facebook Group

His wife said something to him that he'll never forget.

"I would let every business burn to the ground if it meant that when it's nighttime and on weekends, we could spend it as a family."

Dave Menapace didn't argue. Didn't defend himself.

He sat with it. And then he changed everything.

In this episode, E sits down with STR Secrets coach and Five Star Co-Host founder

Dave Menapace — on his birthday — for a raw, unfiltered look at four years of

building, burning down, and rebuilding a short-term rental management company

the right way.

Dave left corporate healthcare in April 2022 with two STRs and a vision.

Four years later, he's managing 58 properties. He signed number 58 this morning.

But the path there? It looked nothing like what he planned.

In this episode:

→ The "seven streams vs. seven jobs" mistake that keeps most operators broke

and burned out — and how Dave finally broke the cycle

→ How he started Five Star Co-Host over from scratch after realizing

he'd built it wrong the first time

→ The $100K IRA withdrawal that gave him the team he needed to grow

→ Why he went from 30 properties to 58 in just 5 months — and the three

obsessions that made it possible

→ The $80,000 trust account crisis that hit in September 2025 — and why

his response to it doubled the business

→ What it actually takes to build a management company worth $100M

(and why Dave believes it's just a choice)

This is not a highlight reel.

It's the version of the story most people are too scared to tell.

Want to connect with Dave? Find him on Instagram: @dave_menapace

Join the community: STR Secrets Facebook Group

Free 6-step course: level.strsecrets.com/pc-book

Timestamps:

00:00 - "Seven streams of income is not seven jobs"

08:07 - Leaving corporate, WealthCon, and the birth of Five Star Co-Host

15:48 - The Miami pool moment Kim told E: "my husband is doing a million things"

32:21 - The most important thing Kim ever said to Dave

35:45 - The three obsessions that unlocked 30 to 58 properties in 5 months

48:17 - The $80,000 crisis and what focus does under pressure

Only 10 seats left

. This is where direct bookings, AI agents, and the next decade of STR get built — live, with the operators leading the charge.

👉 strsecrets.com/aisummit

Most STR operators don't have an information problem.

They have an identity problem.

In this solo episode, mindset coach and STR Secrets co-host Emanuele Pani

breaks down the framework he's been using inside the weekly STR Secrets mindset

calls — and explains exactly why so many operators stay stuck despite doing

all the right things.

If your results haven't caught up to your effort, this episode is for you.

What you'll learn:

→ Why goals are working against you — and why standards change everything

→ The thermostat analogy: why your belief system resets your results back

to where they've always been

→ The LOVE framework for breaking old identity patterns (Liberate, Optimize,

Velocity, Elevate)

→ Why external validation from clients is a ceiling on your business

→ The one question that shows whether your internal story matches

your external goals

→ E's 5 daily affirmations and exactly how to use them morning and night

📘 Free 6-step STR course: level.strsecrets.com/pc-book

💬 Join us: STR Secrets Facebook Group

Timestamps:

00:00 - Why E goes to Italy every summer (and what it actually cost to get there)

09:00 - Stop setting goals. Start setting standards

12:00 - The LOVE framework: how to free yourself from old stories

16:00 - The thermostat analogy: why doing the work is not enough

20:00 - Three questions to ask yourself right now

23:00 - The 5 affirmations that reset your identity every single day"

Only 20 seats left. Use code "PODCAST" for a flat $1000 discount:

👉 strsecrets.com/aisummit

The coupon expires Monday

This is where direct bookings, AI agents, and the next decade of STR get built — live, with the operators leading the charge.

Yorkshire, UK — Mark Simpson spent $50,000 on human appointment setters last year. They did almost nothing.

Then he built one AI agent named Icarus. In 7 days, it closed a $5,000 deal. Cost? Less than $20.

Two months later, Mark has 18 AI agents running inside Boostly. They've generated $54,000 in revenue. And he says he's never hiring a human setter again.

Mark Simpson is the founder of Boostly — the company helping STR operators escape over-reliance on Airbnb and own their direct bookings. He grew up on a farm in North Yorkshire, where his family ran a BNB. Over the last decade, he's refined the most complete direct bookings playbook in the vacation rental industry. Now on his 7th appearance on the show, he's back with the rawest, most honest take on AI agents we've had to date.

This is his blueprint for direct bookings, AI agents, and what's about to happen to operators who don't adapt.

What you'll learn:

→ Why Mark predicts Airbnb's commission is going from 15.5% to 20% — and what the data shows

→ The 65% direct booking goal — and why going 100% direct is just as dangerous as 100% Airbnb

→ The 3 things every direct booking website needs that 90% of operators still get wrong

→ The exact story of Icarus: how Mark built his first AI agent in 2 days and made his money back in 7

→ How Boostly went from a team of 20 to a team of 150 without hiring a single human

→ Why 0.05% of people pay for AI Pro — and how $18 a month puts you in the top 99.5% globally

→ The "18 minutes a day" rule that quietly turns operators into AI power users

→ How Mark trained his entire 22-person team on AI without overwhelming a single person

→ The honest answer to "are you teaching your team to replace themselves?"

→ Why "the cream rises to the top" — and which roles are about to disappear

🎙️ Guest: Mark Simpson | Founder, Boostly

🔗 Website: https://www.boostly.co.uk

🔗 Boostly Connect: https://boostlyconnect.com

🔗 LinkedIn: Mark Simpson

🔗 Instagram: https://www.instagram.com/boostlyuk

🔗 Facebook: https://www.facebook.com/mrmarksimpson

🔗 Book recommendation link: http://bit.ly/2WEOm1v

─────────────────────────────

⏱️ TIMECODES

─────────────────────────────

00:00 - The $50K wasted on human setters and the AI agent that changed everything

01:32 - Mark Simpson returns for his record-breaking 7th episode

02:15 - Life update: 4 kids, World Cup tickets, and the UK trip this summer

03:29 - "Don't build your home on someone else's land" — Mark's signature line

04:00 - Airbnb's fee hike from 3% to 15.5% — and why he saw it coming in 2022

04:30 - The next prediction: why Airbnb is going to 20% commission

06:38 - Top 3 things every operator needs to start direct bookings TODAY

07:02 - Why WordPress still wins in 2026 (and why your PMS landing page isn't a real website)

08:54 - When to flip from "this is a hobby" to "this is a business" (around property 6-7)

09:30 - Why exit-ready businesses always have strong direct booking revenue

11:51 - What does "good" look like? The 65% direct booking benchmark

13:49 - The two-part myth: high-converting website AND content/SEO effort

14:27 - Why hospitality operators are spoiled — and why that's a problem

16:40 - The fundamentals of business that STR operators keep ignoring

17:26 - The "do you know anyone" referral mindset most operators are too scared to use

19:55 - The mirror moment: who do you actually blame for missing your goals?

20:36 - AI agents — Mark's full breakdown starts here

20:57 - Why The Matrix in 1999 still defines how Mark thinks about AI

22:00 - The OpenClaude story: how one weekend GitHub project broke the industry open

24:50 - The breaking point: firing the $50K setter and going all in

25:30 - Meet Icarus — Mark's first AI agent (and the Greek myth behind the name)

26:00 - Real result: $5,000 booking closed in 7 days for under $20 in AI costs

26:30 - 18 agents, $54,000 in revenue, 2 months later

27:19 - Reality check for the shiny object chasers

29:00 - "I'm an idiot" — Mark on why anyone can do this

30:00 - All 22 Boostly employees now have their own AI agent

31:30 - The Google Chrome extension a non-technical team member built in one week

33:00 - The $18 Pro plan stat: why 99.5% of the world isn't paying yet (and what that means for you)

34:00 - The 18 minutes a day rule that compounds into mastery

35:00 - How Mark rolled AI out to his team without overwhelming anyone

36:30 - Comet by Perplexity: the agentic browser changing how teams work

38:04 - "Aren't you teaching them to replace themselves?" The hard question

38:55 - Mark's brutally honest answer (it's not what you think)

41:27 - Why AI Agent Manager is the #1 role being hired for right now

41:51 - The danger of going 100% AI (same risk as going 100% direct)

43:21 - Life on the human side: paddle, books, and saying goodbye to soccer

44:43 - 6 hours back in his day — what Mark plans to do with it

46:55 - The two killers of every operator: lack of attention and poverty of imagination

47:41 - Boostly Connect — the free tool that pulls your PMS data anywhere

49:04 - Mark's #1 secret to AI agent success: just start

─────────────────────────────

🎁 FREE RESOURCES

─────────────────────────────

Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

Boostly Direct Booking Playbook (Mark's book): http://bit.ly/2WEOm1v

Boostly Connect (free up to 10 listings): https://boostlyconnect.com

─────────────────────────────

🔥 STR AI SUMMIT — June 23-24 | Freedom Factory, Beverly, MA

The exact AI systems Mark talks about in this episode? They get built with you LIVE at the summit.

Don't just listen to the playbook. Leave with it installed.

Only 100 seats.

👉 strsecrets.com/aisummit

─────────────────────────────

#ShortTermRental #DirectBookings #AIforSTR #Boostly #STRSecrets #VacationRental #PropertyManagement #AirbnbInvesting #AIAgents #STRScaling

Every homeowner conversation starts the same way.

They want to know what their property can earn.

And if you can't answer that question fast, professionally, and with data behind it —

someone else will.

In this week's training, Mike sits down with STR Secrets coach Ryan Lefebvre to

demo the AI-powered comp analysis tool that's helping property managers turn more

conversations into signed contracts.

Ryan went from 1-2 comp requests a week to 10 a week — from realtors and investors

who now send him every new listing because he delivers branded, data-backed reports

in minutes, not hours.

In this episode:

→ The exact tool Ryan built using Claude that generates a full comp report in

2 to 10 minutes (vs. 20-30 minutes manually)

→ How to use conservative, base, and optimistic revenue projections to handle

any homeowner conversation on the spot

→ Why realtors are becoming one of the fastest referral pipelines for new

management contracts — and how to tap in

→ The AI rabbit hole warning: why building your own tools can quietly kill

your business growth

→ Mike's financial freedom math: exactly how much you need invested to hit

$100K a month in cash flow

→ Why arbitrage is a dead end — and what the data on the biggest arbitrage

companies actually shows

This is not theory. Ryan runs live comps during the session on real properties

submitted by the audience — you'll see exactly how the tool works in real time.

Want the comp tool? DM COMP at mike.sjogren

and we'll send it straight to you.

Ready to install this and a full AI system for your business live?

Timestamps:

00:00 - Intro & Ryan Lefebvre's background

01:42 - From financial crime analyst to AI builder for STR

04:22 - How the comp tool works and what it produces

06:33 - Live demo: running an Airbnb listing in real time

09:26 - Interactive sliders and revenue scenario conversations

11:17 - How to handle bad comps and sparse markets

13:36 - Live demo: running a property address

17:34 - How the tool handles off-market or renovated properties

22:38 - Using comp reports to show homeowners the gap between unmanaged and managed

26:41 - AI Summit: what's being covered and who's speaking

29:04 - Ticket pricing and how to register

32:02 - Alex case study: 2 properties to 35 in one year

35:29 - The AI rabbit hole warning

38:00 - Using AI at any portfolio size

41:06 - Mike's financial freedom math ($8M at 15% = $1.2M/year)

44:46 - Why arbitrage is a dead model

49:27 - Should you replace your channel manager with AI? (No. Here's why)

52:45 - Q&A: summit details, recordings, revenue manager AI tool

Use code "MEMORIAL500" while checking out at strsecrets.com/aisummit

You're doing the work. You're managing the properties. You're showing up every day.

So why does it feel like you're spinning your wheels?

In this solo show, Chris Petzy and Emanuele Pani get raw about the real reason STR

operators stall out — and it has nothing to do with the market, your pricing strategy,

or your occupancy rate.

In this episode:

→ The 3 silent causes of business stagnation (and which one is quietly killing your

growth right now)

→ Why split focus will never equal scale — and the one decision Chris made that

changed everything

→ The identity gap: how to stop making decisions from who you've been and start

making them from who you're becoming

→ E's 5 daily affirmations that rewire how you start every single day

→ Why hiring for today's need is the biggest mistake scaling operators make

If the last six months didn't go the way you planned, this episode is your reset.

Ready to build the business that funds the life?

Apply to work with us: strsecrets.com/apply

🔥 STR AI SUMMIT — June 23-24 | Freedom Factory, Beverly, MA

Dr. Rachel is flying in to spend 2 full hours building this exact system with you live.

You won't just learn it. You'll leave with it installed. Only 70 seats left.

👉 strsecrets.com/aisummit

Most STR operators know they need to post more. They just don't have the time, the team, or the system to do it.

Dr. Rachel Gainsbrugh does. And in Portfolio Clinic Episode 8, she pulls back the curtain on the exact AI content engine she built to generate weeks of social content without living on her phone.

Dr. Rachel is a former full-time physician turned full-time real estate investor, entrepreneur, AI strategist, and founder of Short Term Gems. She built her entire content system out of necessity — and now it runs largely without her.

In this episode, Mike Sjogren sits down with Dr. Rachel to walk through the full system live: from raw meeting notes to scheduled carousels, with AI agents doing most of the heavy lifting.

What you'll learn:

→ The 7-11-4 rule: why buyers need 7 hours of content across 11 touchpoints on 4 platforms before they trust you enough to write you a check

→ Meet Vega — the AI agent that processes all your meeting notes every night and sorts them into content, SOPs, and coaching opportunities before you wake up

→ Meet Carrie — the carousel sniper that takes one Airbnb link and delivers 10 ready-to-post carousels including captions and CTAs

→ Meet Contesta — the content queen that formats everything for each platform and sends it to scheduling automatically

→ How a property manager with 80 doors sent 60 personalized owner emails in 2 hours (he used to spend his whole weekend on it)

→ How to train your AI like an employee using SOPs — and why that one step changes everything

→ The AI data privacy protocol that keeps your sensitive files in a sandbox and out of reach

→ Why posting once or twice a week means you are already losing to operators using this system

🎙️ Guest: Dr. Rachel Gainsbrugh | Founder, Short Term Gems

🔗 Get Carrie the Carousel Sniper Agent: https://level.strsecrets.com/drrachel

─────────────────────────────

⏱️ TIMECODES

00:00 - Cold open: Carrie the carousel sniper demo — one Airbnb link, ten carousels

00:57 - Mike and Dr. Rachel intro — why she's the go-to AI person in the space

01:34 - Dr. Rachel's background: from full-time doctor to AI-powered STR investor

02:13 - The 7-11-4 rule: the Modern Trust Formula every operator needs to understand

03:04 - Two content angles for STR operators: repeat guests and new client acquisition

03:39 - Why Dr. Rachel built this system (she hates being on camera)

05:24 - The note taker habit that turns every meeting into a content asset

05:48 - The Plaud Note Pin: the wearable AI recorder Mike and Rachel swear by

07:09 - Meet Vega: the AI night agent that sorts all your meetings while you sleep

07:53 - How Vega triages every meeting into four buckets before you wake up

08:15 - Real demo: Vega identifies a coaching frame used 14 times across calls and flags it

09:23 - 425 meetings reviewed by AI that no human ever had time to touch

09:56 - How Vega processes data directly from Fireflies, Otter, and Plaud using schema

13:22 - Step two: turning the content database into actual social posts with Contesta

13:58 - Real proof: 80-door property manager sends 60 personalized owner emails in 2 hours

14:22 - How Contesta routes content to Phoebe (Facebook) and schedules it automatically

15:15 - How Mike applies this to property walkthroughs and hotel renovation updates

16:14 - Why guest reviews are an untapped content goldmine most operators ignore

17:20 - The one thing Dr. Rachel warns against: asking AI to write posts with no context

18:05 - How to sell through your real stories: the three-part owner acquisition framework

19:15 - Mike's local events agent: scraping tourism data to feed newsletters and social

20:18 - Why showing your journey (not the polish) is what builds trust and drives bookings

21:46 - Meet Carrie: the carousel sniper — live demo walkthrough

23:11 - Carrie in action: pulling property photos from Airbnb, building 8-10 slide carousels

24:50 - Guest reviews as carousel slides: 122 reviews turned into content automatically

25:29 - Carrie delivers: full carousel batch plus caption, CTA, and downloads folder

26:00 - Is all of this through Claude? Yes — Claude Co-Work and Claude Code

27:04 - How long it took to build Carrie (two months) and how fast it runs now (one command)

28:44 - Train AI like an employee: the SOP-first method for consistent results

29:49 - Real world result: executive assistant elevated from admin to EA after AI frees her up

31:47 - Dr. Rachel is speaking at the AI Summit — two full hours of live building with you

33:43 - How to train Claude with SOPs, PDFs, and audit loops

35:26 - AI quality is only as good as your SOP — garbage in, garbage out

36:31 - Who owns your property photos? What every operator needs in their photographer contract

37:19 - The Night Janitor: the AI agent that organized 16,000 photos and files in minutes

39:15 - How to talk to Claude about your messy photo library and get a real solution

41:05 - Claude Code vs. Claude Co-Work: when to use which for scheduling and automation

41:35 - Should you have separate social accounts for owner acquisition vs. guest direct bookings?

43:49 - Training AI vs. training humans: why right now is the best time to be an operator

47:02 - AI Summit preview: June 23-24, Freedom Factory, Beverly MA — build it live with Rachel

48:19 - The volume reality: someone using this system is posting 3x a day while you post twice a week

─────────────────────────────

🎁 FREE RESOURCES

Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

#ShortTermRental #AIforSTR #STRSecrets #VacationRental #PropertyManagement #ContentStrategy #AirbnbInvesting #AIAgents #DirectBookings #STRScaling

Only 100 seats. Built for operators who are serious about what comes next.

👉 strsecrets.com/aisummit

If you're managing 5, 10, or 50+ properties and wondering whether AI is a tool or a threat — Marcus Räder has the answer. And it's not what most people are saying.

Marcus is the co-founder and CEO of Hostaway — the first vacation rental software company to reach unicorn status and the recipient of the largest funding round in vacation rental history: $365 million led by General Atlantic.

He's been in this industry for over a decade. He's seen every wave. And right now, he's more excited — and more concerned for unprepared operators — than ever before.

In this episode, E and Chris sits down with Marcus for one of the most candid, far-reaching conversations in the show's history. From AI and private equity to running 100 marathons in 100 cities — this one goes deep.

What you'll learn:

→ Why private equity is circling STR operators right now and what it means for your business valuation

→ The #1 thing AI can't do for your properties (and where most operators are dangerously overconfident)

→ Why "more data = more visibility" is the new SEO — and how to make your listings AI-search-proof

→ The direct booking strategy that still works in 2026 (the basics haven't changed as much as you think)

→ How to build a team that thinks 3 years ahead when they're wired to think about today

→ The honest truth about building a big business vs. just being great at your job

→ What losing 70 pounds and running 17 marathons taught Marcus about scaling anything

🎙️ Guest: Marcus Räder | Co-Founder & CEO, Hostaway

🔗 Connect: https://www.linkedin.com/in/marketingmarcus/

🌐 Website: hostaway.com

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⏱️ TIMECODES

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00:00 - The hard truth: adapt to AI or lose guests to someone who did

02:01 - E & Chris reconnect — scaling conference takeaways + the Sardinia deal update

05:39 - Introducing Marcus Räder: building Hostaway into a $1B business

08:50 - Living the hybrid US-Europe life with family (7 months abroad)

11:48 - Hostaway's origin story: from channel manager to full PMS to $365M raise

14:03 - What it actually feels like to run a unicorn — the founder's relationship with time

16:20 - How to build a team that thinks years ahead when employees focus on today

17:34 - Why Marcus's best hires came from web hosting, not STR

19:37 - AI in STR: excited or worried? Marcus's honest take from the CEO seat

21:47 - The viral meme that perfectly exposes the DIY AI trap

22:45 - What STR operators really do during peak season (it's not what you think)

23:06 - Where AI fails: raccoons, hurricanes, guest injuries, and edge cases

24:15 - How Hostaway built its AI control layer for guest communications

27:00 - Build in-house vs. stay third party: Marcus's framework for scaled operators

28:33 - The hidden danger of AI models that silently update and change answers

29:41 - The Uber lesson every STR operator needs to hear right now

31:25 - Will AI become a race to the bottom? Where monetization is heading

32:07 - The pool pump disruption: how AI reshapes maintenance costs and who profits

34:00 - "Findability" — go ask AI to find YOUR property right now and see what happens

35:15 - Why private equity is turning STR businesses into 10x assets with AI

36:18 - What the next decade of Hostaway looks like

38:33 - Direct bookings in 2026: the dead-simple strategy most operators still skip

39:26 - Why your listing description is failing AI search (and the wall of text fix)

41:42 - Data is the new currency: whoever gives AI the most wins the booking

42:13 - Build big or go work for someone — Marcus's hard truth about entrepreneurship

43:13 - 100 marathons in 100 cities: the health journey and what flat feet taught him

47:07 - The calorie analogy that explains how small disciplines compound at scale

49:36 - Marcus's #1 secret to STR success: boring, consistent, and most people skip it

─────────────────────────────

🎁 FREE RESOURCES

─────────────────────────────

Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

─────────────────────────────

#ShortTermRental #AirbnbInvesting #STRSecrets #VacationRental #PropertyManagement #STRScaling #AIforSTR #Hostaway #DirectBookings #RealEstateInvesting

Mike Sjogren spent over $5,000 in API credits in two months learning AI the hard way. And he wants to make sure you don't have to.

In this Portfolio Clinic training, Mike breaks down the top 10 AI mistakes that cost him real money — from not understanding context windows to memory file bloat to giving an agent 15 tasks at once and wondering why nothing got done. He then walks through exactly how STR operators should be using AI right now across three buckets: getting more properties, getting more bookings, and getting more time back.

He also shows how he rebuilt his Florida direct booking website in under a day for under $200 using Manus, how his AI agent scrapes top boutique hotel social media content overnight and delivers a morning brief, and why the goal is never to build your own software — it's to use AI as a bolt-on to everything you already have.

DM Mike on Instagram @mike.sjogren and comment PROMPT to get the free PDF of all the prompts he used to build his direct booking website.

STR AI Summit — June 23-24 at the Freedom Factory in Beverly, MA. 100 seats only.

strsecrets.com/aisummit

Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

Timestamps:

0:00 - Why Mike Is Doing This Training (And How Much It Cost Him)

2:15 - Mistake #1: Not Understanding Context Windows ($6 Per Message)

5:30 - Mistake #2: Memory File Bloat — Why AI Gets Dumber Over Time

7:45 - Mistake #3: Using Your Most Expensive Model for Everything

10:00 - Mistake #4: Broken Cron Jobs — How to Schedule Tasks That Actually Run

13:00 - Mistake #5: Treating AI Like an Employee Who Can Handle 15 Things at Once

16:30 - Mistake #6: Not QC-ing the Output

18:00 - Mistake #7: Trying to Build Your Own PMS or Pricing Tool

20:30 - The 3 STR Buckets: More Properties, More Bookings, More Time

23:00 - How to Use AI to Automate Your Entire Prospecting Pipeline

27:00 - How to Use AI to Get More Bookings Right Now

30:00 - How to Rebuild Your Direct Booking Website With AI for Under $200

36:00 - How Mike's Overnight Agent Scrapes Top Hotel Content Every Night

39:00 - The 10 Rules for Using AI Without Burning Your Budget

42:00 - How to Motivate Your Team to Use AI Without Fear

46:00 - Where to Start If You're Brand New to AI

48:00 - STR AI Summit: June 23-24 at the Freedom Factory

Only 100 seats. Early bird: $1,497.

strsecrets.com/aisummit

Tying your identity to your door count is the fastest way to burn out—or worse. In 2008, Rod Khleif lost $50 million. He calls it an expensive "seminar."

In this episode, E sits down with Rod to discuss how he rebuilt his massive real estate portfolio by fundamentally changing his peer group and his mindset.

Today, Rod's students own over 260,000 units, and he has fed more than 160,000 children through his Tiny Hands Foundation. He breaks down the massive demographic shift he calls the "Silver Tsunami"—why the demand for senior housing is about to explode, and how his team is acquiring assisted living facilities for $40,000 a door.

He also shares a massive wake-up call regarding Artificial Intelligence, explaining exactly how his own marketing team is using Claude AI to replace 95% of their manual workload.

Connect with Rod Khleif:

Website: http://Rodkhleif.com

Podcast: Lifetime Cash Flow Through Real Estate Investing

Instagram: https://www.instagram.com/rod_khleif/

Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

100 seats only. Grab your ticket: https://www.strsecrets.com/aisummit

Most STR operators have built a great lifestyle business. But here's the hard truth: only 1 in 10 businesses will ever successfully sell. The rest close and walk away with nothing.

In this Portfolio Clinic training, Mike Sjogren breaks down exactly how STR management companies are valued — and what operators need to start doing right now to build a business with a real exit strategy.

He walks through the EBITDA formula, the exact valuation metrics used by C2G Advisors (the top M&A firm in the STR industry), why rental arbitrage and co-hosting businesses get little to no value from buyers, and why private equity has been quietly acquiring STR management companies since 2022.

He also introduces the Freedom Collective — STR Secrets' own roll-up model designed to give operators a share of the upside instead of selling to private equity at a discount. And he breaks down how AI agents can automate an entire acquisition pipeline from property data scraping to sales call booking.

Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

Career or kids. No middle ground.

Then her daughter was diagnosed with leukemia at three years old.

And everything changed.

Jane Ng left corporate America to care for her daughter full time. Her daughter survived — but was left with a brain injury that means she will never be fully independent. Jane will care for her for the rest of her life.

So going back to a W2 was never an option.

Instead she found real estate. Then short term rentals. Then co-hosting. Then a coaching business helping other moms do the same thing.

Today she owns 4 STRs, co-hosts 11 properties, runs a coaching business — and is home every single day for her kids.

Here's what she shared in this episode:

→ How she bought her first out-of-state property for $50K while parked on the side of a road in New Orleans

→ Why STRs are one of the most powerful tax savings tools for stay-at-home parents

→ How she built a team that runs the whole operation — with just one weekly check-in call

→ How she structures her week so she is never tied to her phone

→ The mindset shift that stopped her from quitting when things got hard

→ How she uses AI to find her next STR market before she even talks to a realtor

→ Why hospitality — not just for guests but for cleaners, neighbors, and vendors — is her #1 secret

This episode is for every mom who thinks she has to choose.

She doesn't.

Connect with Jane:

Instagram: @theinvestingmom

YouTube: @theinvestingmom

Connect with us:

Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

Timestamps:

0:00 - Intro

4:10 - Introducing Jane Ng: The Investing Mom

4:42 - How Jane's Daughter's Diagnosis Changed Her Life Forever

6:21 - Why Going Back to a W2 Was Never an Option

7:03 - Parked on the Side of a Road in New Orleans: The Moment Everything Changed

8:20 - From Long-Term Rentals to STRs: The 1031 Exchange That Started It All

9:18 - Why Her Daughter's Illness Made Her Braver in Business

11:39 - The Middle Ground: How STRs Let Her Be a Mom and an Operator

13:28 - The Identity Guilt That Holds Moms Back — and How to Get Past It

15:10 - Her Morning Routine: Up at 5:30, Kids First, Business Second

18:01 - Portfolio Overview: 4 Owned STRs, 11 Co-Hosted Properties, 3 Businesses

18:25 - Why the STR Tax Loophole Is a Game Changer for Stay-at-Home Parents

20:32 - How Co-Hosting Started: She Said No 6 Times Before Saying Yes

22:06 - How She Built Her Social Presence as a Self-Described Introvert

25:49 - How She Manages Everything: VA Structure, Weekly Check-Ins and Time Blocking

28:07 - How She Structures Her Week to Never Feel Tied to Her Phone

31:07 - Start Small: How to Build Good Habits Without Overwhelming Yourself

36:46 - How She Uses AI to Find Her Next STR Market

39:19 - Her #1 Secret to STR Success: Hospitality for Everyone

Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

Apply to work with us: https://strsecrets.com/apply

STR Secrets Podcast: https://strsecrets.com/podcast

Most luxury STR owners write that electric bill every month without ever knowing what's causing it. David VanWert did the same thing — until he built a platform to fix it.

In this episode, E and Chris sit down with David VanWert, founder of Umbra and owner of seven STR cabins in the Smoky Mountains and Mammoth Lakes. David built Umbra after spending years watching energy costs silently destroy the profitability of high-end vacation rentals — and after realizing no existing solution was built for the STR world.

In this episode David covers:

- What Umbra does: smart power monitoring and automation built specifically for large luxury STRs

- How Umbra integrates with your PMS to automatically cut power when guests check out

- Real results: 45% reduction in electricity cost per night, $620 saved in one month on one property, 30% lower bill YoY

- How silent system failures — clogged AC units, water leaks, tripped breakers — get caught before they become emergencies

- Why electricity costs in the Smoky Mountains regularly hit $2,000-$3,000 per cabin in winter — and how to stop that

- How David scaled to seven properties in under five years using second home loans, cost segregation studies, and the STR tax loophole

- Why the STR tax play — not cash flow — is the real opportunity for high-income earners buying right now

- David's full AI workflow: how he rebuilt his entire business from the ground up using Claude

- How he cut a 100-hour design project down to under 20 hours with AI

- Why he believes operators have a 4-6 year window to get ahead of AI before things get "weird"

- The time study method: how to audit every 15-minute block of your day and identify what AI can automate

- What happens to property managers and co-hosts when AI agents handle all communications, scheduling, and pricing

- David's #1 secret to STR success: tenacity

This is a rare conversation — equal parts operations, tech, and honest truth about where this industry is headed.

---

About David VanWert:

David VanWert is the founder of Umbra, a power-monitoring and automation platform built specifically for large luxury short-term rentals. He owns seven cabins — six in the Smoky Mountains and one in Mammoth Lakes — and built Umbra after experiencing firsthand how much energy waste and property risk goes undetected in high-end vacation rentals. His background is in technology and design, and he now splits his time between operating his own portfolio and helping other owners and property managers answer one simple question: what's running right now, and should it be?

Connect with David and Umbra:

Website: umbra-energy.com

Instagram: @umbraenergy

Facebook: Umbra Energy

Timestamps:

0:00 - Intro

1:22 - Introducing David VanWert and Umbra

5:28 - E's Michelin Restaurant Story: Service Is Black and White, Hospitality Is Color

9:06 - What Is Umbra and Why Did David Build It?

10:58 - The Real Cost of Running a Luxury STR: $2,000-$3,000 Electric Bills in the Smokies

12:49 - How Umbra Works: Smart Power Automation Tied to Your PMS

14:34 - Real Results: 45% Reduction, $620 Saved in One Month

16:37 - How Umbra Catches Silent Failures Before They Become Emergencies

18:34 - David's Background: From High-End Home Automation to STR Investor

20:26 - How David Scaled to Seven Properties in Under Five Years

21:58 - The STR Tax Play: Why High-Income Earners Should Be Buying Right Now

24:30 - Is the STR Market Still Worth It? What David Is Seeing Today

27:46 - How David Rebuilt His Entire Workflow Using Claude and AI

33:25 - From 100 Hours to 20: How AI Changed His Design Business

40:13 - The 4-6 Year Window: Why You Need to Get Ahead of AI Right Now

43:11 - What Happens to Property Managers When AI Handles Everything?

45:00 - Where to Start With AI If You Have No Tech Background

47:26 - David's #1 Secret to STR Success: Tenacity

If you haven't updated your pricing yet — your next booking will pay you less than you expect.

Btw you can grab the spreadsheet from here : https://www.strsecrets.com/airbnbfee

Also, if you want to talk to us directly: http://strsecrets.com/implement

In this training Mike covers:

- What the Airbnb fee change actually means: 15.5% host-only fee applies to nightly rate, cleaning fee, resort fee, pet fee — everything

- Why the split fee showing back up in your account is a bug — not a reversal

- The exact price increase you need to make: 18.34% minimum for direct owners

- How co-hosts and property managers need to handle this differently — and why checking the listing owner's account first matters

- The fee change spreadsheet walkthrough — how to model the right scenario for your business (comment FEE CHANGE to get it)

- How to split the channel fee with your homeowner so nobody loses

- How to track your Airbnb algorithm ranking after raising prices using Rank Breeze

- Why five-star properties make 18% more in RevPAR than 4.7-star properties — and how that matters more right now

- How Mike's portfolio is pacing 130% of June goals and 120% of July goals — and why

- Why now is the time to get on Vrbo — Mike is seeing 10% more bookings YoY from Vrbo this year

- How to retarget past guests with text messages and automated campaigns to offset any Airbnb drop

- Listing optimization basics: why your first five photos, your copy, and your reviews are your most valuable assets right now

This is the most important training for STR operators this month.

📲 Connect with STR Secrets:

STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

Apply to work with us: https://strsecrets.com/apply

STR Secrets Podcast: https://strsecrets.com/podcast

Timestamps:

0:00 - What Just Happened: Airbnb's Fee Change Explained

1:16 - The Split Fee Is Not Back — It Was a Bug

2:23 - What 15.5% Host-Only Fee Actually Means for Your Payout

3:04 - Step 1: Increase Your Airbnb Pricing by 18.34% Right Now

4:27 - Step 2: Track Your Algorithm Ranking After Raising Prices

5:44 - How to Check and Confirm Your Fee Setting in Airbnb

8:21 - The Fee Change Spreadsheet Walkthrough

12:30 - How to Split the Channel Fee With Your Homeowner

14:26 - What Co-Hosts and Property Managers Need to Do Differently

15:12 - How to Make Pricing Changes Inside Your PMS

16:03 - Testing Price Increases: 15% vs 18% vs 25% — What We've Seen

18:01 - The Airbnb Algorithm: What Actually Moves Your Ranking

18:25 - Five-Star Properties Make 18% More in RevPAR

19:48 - Virtual Stays, Friends and Family Reviews and Algorithm Boosts

20:15 - Mike's Portfolio Is Pacing 130% of June Goals — Here's Why

21:03 - Get on Vrbo: Mike Is Up 10% YoY From Vrbo This Year

22:15 - Retarget Past Guests With Text Campaigns Right Now

23:45 - Listing Optimization Basics: Photos, Copy and Reviews

24:07 - Action Steps and Where to Get the Spreadsheet

STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

E just got back from the Unreasonable Hospitality Summit in Nashville — and this solo episode is his full recap.

Will Guidara wrote Unreasonable Hospitality during COVID. He took Eleven Madison Park from a nice restaurant to the #1 restaurant in the world — the only restaurant to ever go from one Michelin star to three in a single year.

His philosophy: service is what you do for people. Hospitality is how you make them feel.

In this episode E breaks down the biggest lessons from the summit — how to systematize hospitality so your team delivers it consistently, why hiring the person over the resume matters more than you think, how to build a culture of praise and feedback that makes teams want to grow, and why the magic moments your guests remember are never accidental.

He also tackles the AI question head on: the answer is not cutting your team — it is repurposing them to create more human moments in a world where genuine connection is becoming a scarce resource.

The episode closes with the question Will Guidara asked the room that E says called him to greatness: "What would you attempt to do if you knew you couldn't fail?"

Get the book: Unreasonable Hospitality by Will Guidara

New book: Unreasonable Hospitality Field Guide (released April 28, 2026)

Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

If you want to join our weekly free training:

https://www.facebook.com/groups/STRentalsecrets

Most property managers and co-hosts pitch homeowners on management fees.

Mike Reilly pitches them on $100,000 in tax savings. And it closes more deals than anything else.

In this Portfolio Clinic training, Mike breaks down the STR tax loophole — why it works, who qualifies, and exactly how to use it to attract high-income homeowners and win management contracts.

This is not investment or tax advice. But it is the most powerful conversation you can have with a prospective homeowner — and most co-hosts and property managers are never having it.

In this training Mike covers:

- Why taxes are the #1 expense for every high-income W2 earner and business owner

- How a doctor making $375K in California goes from a $145K tax bill to a $47K tax bill — with one STR

- What a cost segregation study is and how it accelerates depreciation in year one

- The two requirements to qualify for the STR loophole: 7-day average stay and 100+ hours of material participation

- Why 90% of CPAs don't know this loophole exists — and how to help your homeowner educate theirs

- The exact conversation flow to have with prospective and new homeowners

- How Mike charges a $20-25K consulting and design fee upfront — then takes over management in year two

- Real results: one homeowner got $80K back this year, another got $60K last year

- How to structure the deal so the homeowner qualifies AND you get the management contract

- What to do with a cost segregation study if the homeowner wants to be fully passive

- How to handle depreciation recapture and when to recommend a 1031 exchange

This is one of the highest-leverage strategies a co-host or property manager can learn right now.

Want help implementing this in your business?

Go to: https://strsecrets.com/implement

📲 Connect with STR Secrets:

Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

Apply to work with us: https://strsecrets.com/apply

STR Secrets Podcast: https://strsecrets.com/podcast

Timestamps:

0:00 - Why Taxes Are Your Homeowner's Biggest Expense

3:20 - The Math: How a Doctor Paying $145K in Taxes Can Change Everything With One STR

6:00 - What Is a Cost Segregation Study and Why Every Homeowner Needs One

8:30 - How Much Can You Depreciate in Year One? (The 25% Rule)

10:00 - The Two Tests to Qualify for the STR Loophole

12:00 - Running the Numbers: From $145K Tax Bill to $47K With One Property

14:30 - The Exact Conversation to Have With Every Prospective Homeowner

16:30 - How to Charge a Consulting Fee and Design Fee Upfront

18:00 - Real Results: $80K Back This Year, $60K Last Year

19:30 - What If the Homeowner Wants to Be Fully Passive?

21:00 - Depreciation Recapture and When to Recommend a 1031 Exchange

22:00 - Q&A: Cost Seg on an Existing Property, Passive Losses and More

Most couples don't survive a loss like that. Instead, it became the moment that changed everything.

In this episode, E and Chris sit down with Cara and Mark Truckey — two STR Secrets boardroom alumni who have built a real estate portfolio of 65+ units across Wisconsin and Florida while raising three kids and running multiple businesses.

This is one of the most honest and human conversations we have had on this show.

In this episode Cara and Mark cover:

- How losing their son reshaped their entire perspective on time, work, and money

- How Cara quit her hospital job in 2020 and Mark quit his plumbing W-2 in 2021

- How they went from a few house flips to 65+ rental units across two states

- Their first STR — a lake property in Wisconsin they bought by accident

- Why Mark struggled with delegation for years — and the 80/20 rule that broke the pattern

- How to find the right people for the right seats — and why belief in the vision matters more than skills

- How Cara transitioned into Savvy Realty as a top agent in the Tampa Clearwater market

- What actually keeps a husband and wife business partnership aligned

- The daily habit that is their real superpower — and has nothing to do with business

- How to change your identity before the results show up

- Mark's upcoming $130 million capital campaign for a K-12 school in Wisconsin

- Cara's goal: 40 STRs under management in Florida by end of 2027

- Their #1 secrets to success: courage and fighting past limiting beliefs

If you want to increase your revenue, automate your day to day operations and spend more time with your kids: http://strsecrets.com/apply

If you want to join our weekly free training:

https://www.facebook.com/groups/STRentalsecrets

Connect with Cara:

Instagram: www.instagram.com/caratruckey

Facebook: www.facebook.com/caratruckey

Savvy Realty: www.savvy.realty/cara

Timestamps:

0:00 - Highlights

1:00 - Introducing Cara and Mark Truckey

5:05 - Their Story: Growing Up in Wisconsin and Losing Their Son in 2016

7:32 - How Grief Changed Their Relationship With Time and Money

9:03 - How They Built the Portfolio: Flips, BRRRs and Their First Accidental STR

10:21 - How They Split the Business: Cara on Sales, Mark on Construction

11:56 - Building the Team: Florida and Wisconsin Operations

14:11 - Mark's Delegation Journey: The 80/20 Rule That Changed Everything

16:48 - Right People in the Right Seats: Why Belief in the Vision Matters Most

18:24 - Identity First: You Have to Become the Person Before the Results Show Up

21:33 - How to Actually Change Your Identity — Not Just Understand It

24:28 - Why Being Part of a Mastermind Has Always Been Their Edge

25:25 - Running a Business With Your Spouse — What Actually Works

26:47 - Spiritual Alignment: The Foundation That Kept Them Together Through Tragedy

27:23 - The Matthew McConaughey Analogy: You Won't Always Walk Side by Side

32:21 - How Cara Made the Decision to Join Savvy Realty

35:00 - Their Real Superpower: Health, Accountability and Alignment

38:27 - What's Next: Mark's $130M School Campaign and Cara's Management Goals

42:23 - Their #1 Secrets to STR Success

If you want to join our weekly free training:

https://www.facebook.com/groups/STRentalsecrets

Every time a past guest books your property again through Airbnb — Airbnb takes the fee. Again. Repeat guests generate over $1 billion in revenue for Airbnb annually. And most STR operators are doing nothing to capture that themselves.

In this Portfolio Clinic session, Mike Reilly breaks down the direct booking system he uses across his 30-property portfolio — and reviews a real direct booking website live with a community member.

He walks through how to collect guest info from every Airbnb and Vrbo stay, how to build a 12-touch text and email funnel that brings guests back without the OTA in the middle, and how to incentivize your team to close direct bookings on your behalf.

He also covers the occupancy tax process most operators get wrong, why your contact list is a business asset that increases your company's exit value, and what actually makes a direct booking website convert.

If you are still relying 80-100% on Airbnb for bookings — this is the training that changes that.

Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

Timestamps:

0:00 - Why Airbnb Makes $1 Billion From Your Repeat Guests

2:27 - Why You Can't Build a Business on Someone Else's Land

4:36 - How Airbnb's Fee Change Impacted Revenue (And What to Do)

7:05 - Occupancy Tax: The Mistake That Could Cost You a Six-Figure Bill

9:23 - Live Website Review: Lori's Direct Booking Site

13:43 - What Makes a Direct Booking Website Actually Convert

19:53 - How to Collect Guest Info From Every Airbnb and Vrbo Stay

21:15 - The QR Code Exit Strategy That Drives Direct Bookings

21:35 - The 12-Touch Text and Email Funnel for Repeat Guests

24:34 - Why Mike Pays His Team $50 Per Direct Booking Closed

25:41 - Two Social Posts a Week — Done by Your Team, Not You

27:32 - How a 3,000-Contact CRM Protects You If Airbnb Shuts You Down

31:07 - Why Direct Bookings Increase Your Company's Exit Valuation

33:54 - Action Items and Closing Thoughts

If you want to join our weekly free training:

https://www.facebook.com/groups/STRentalsecrets

Most STR operators don't think about regulation until it's already too late.

Julie pulls back the curtain on what’s really happening in short-term rental regulation and why hosts can’t afford to stay invisible. From local politics to nationwide advocacy, this episode is a wake-up call for operators who think regulation is someone else’s problem.

Here's what we covered:

• How Julie went from accidental host to industry advocate

• Why anti-STR arguments often hide deeper community concerns

• The biggest mistake hosts make when regulations start changing

• Why advocacy is not charity, but a real business investment

• How small hosts can contribute without becoming full-time activists

• What the Right to Rent Collaborative is building for the future of the industry

Guest Bio:

Julie Marks is Executive Director of the Right to Rent Collaborative (R2RC), a national initiative supporting state and local short-term rental associations in building advocacy capacity, legal readiness, and sustainable funding infrastructure. An association founder and industry advocate, Julie works at the intersection of national strategy and local execution, helping communities organize and engage effectively with policymakers.

Julie founded the Vermont Short-Term Rental Alliance (VTSTRA) in 2021 and served on the Vacation Rental Management Association’s Government Affairs Council from 2022 to 2024. She operates Homestead Hospitality in Vermont and manages rental properties in Vermont and Washington.

Connect with Guest:

julie@r2rcollaborative.org

https://www.linkedin.com/in/juliemarksvt/

https://www.instagram.com/vtstra/

https://www.instagram.com/r2rcollaborative/

Timestamps:

0:00 - Intro

8:01 - Introducing Julie Marks

8:28 - How Julie Accidentally Became an STR Advocate

10:00 - From Op-Ed to Statewide Alliance: The Vermont Story

11:26 - Why the Same Fight Is Happening in Every Market

12:23 - What Communities Are Really Upset About (It's Not What You Think)

16:19 - The Hard Truth: What STRs Have Genuinely Changed

18:34 - Why "It Won't Happen in My Market" Is a Dangerous Assumption

21:16 - How to Get Involved Without Going to Every City Hall Meeting

23:35 - What the Right to Rent Collaborative Does and How It Works

26:17 - "I'm Too Small to Matter" — Julie's Response

28:21 - The $2 Per Booking Model: Your Business Insurance Policy

29:08 - Why This Is a Branding Opportunity, Not Just an Obligation

35:52 - How to Start a Local Association From Scratch

38:23 - Where to Find Julie and Get Connected

39:36 - Julie's #1 Secret to STR Success

If you want to join our weekly free training:

https://www.facebook.com/groups/STRentalsecrets

This one is different.

At our last STR acquisitions event at the Freedom Factory in Beverly, MA, we did something we'd never done before.

We filled a hat with real homeowner objections — things operators hear every day — and had four coaches handle them live on stage in front of 50 operators.

No prep. No script. No safety net.

Coaches Mike Reilly, Dave, Darryl, and E took turns handling objections like "your fees are too high," "you're not local," "I don't want to be locked in," and "I want to take advantage of the STR tax loophole." Each coach handled them differently — because that's the point. There is no single right answer. There's the answer that fits your voice.

This is an hour of live, unfiltered STR sales training recorded in the room. If you're growing a property management or cohosting business, this episode will change how you handle objections.

Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

If you want us to review your listing, org chart, pricing or anything related to STR business, join here:

➡ https://www.facebook.com/groups/STRentalsecrets

Most STR companies obsess over guest reviews.

Blue Gems obsesses over owner profitability.

And they grew to 180 properties under management doing it.

In this episode, recorded live at the Freedom Factory in Beverly, MA, E and Chris sits down with Aidan Groll — co-founder of Blue Gems Management, one of Florida's fastest-growing STR companies. Aidan and his partner JB manage 180+ properties across Orlando and Clearwater Beach with a 36-person team — and grew almost entirely through organic relationships, not paid ads.

In this episode Aidan breaks down:

- How he went from a corporate accounting job to buying his first duplex in March 2020

- How a 400 sq ft backyard ADU made $50K in its first year and convinced him to go all in on STRs

- Why Blue Gems puts owners 70% over guests — and how they pitch that to new clients

- Their full org chart at 180 units: 14 in maintenance, 7 in guest experience, 3 in sales and more

- Why they do ALL maintenance in-house — and why speed was the deciding factor

- How they automated 70% of guest communication with AI in the last year

- Their 7-day contract-to-live-listing goal and how they hit it consistently

- How they choose markets based on regulatory stability — not just cash flow

- Why they shut down their podcast and social media for 2+ years to focus on growth

- Their plan to reach 350-400 units through acquisitions of smaller operators

- The Valley of Disappointment — and why most people quit right before it gets good

- Aidan's #1 secret to STR success: patience

This is a masterclass in building a real, scalable STR management business.

---

About Aidan Groll:

Aidan Groll is the co-founder of Blue Gems Management, an Orlando-based vacation rental management company that has grown to oversee 180+ properties across Florida. Originally a real estate investor with a background in corporate accounting, Aidan and his business partner JB pivoted to short-term rentals in late 2021 — building their own management infrastructure before opening to third-party clients in early 2023. Since then, Blue Gems has scaled to a 36-person team with full in-house maintenance operations, serving property owners across Orlando and Clearwater Beach.

Time Stamps:

0:00 - intro

0:54 - Introducing Aidan Groll and Blue Gems Management

1:28 - What Blue Gems Does Differently (Owner-First Philosophy)

4:14 - The Real Cost of Building This Business

5:08 - Aidan's Origin Story: From Accounting Job to House Hacking in 2020

7:54 - The $50K ADU That Changed Everything

9:10 - Scaling to 180 Properties: How Blue Gems Grew Without Paid Ads

10:46 - The Contrarian Take: Why They Don't Chase 5-Star Reviews

13:46 - How to Pitch the Owner-First Model to New Clients

18:26 - Inside the Org Chart: 36 People, 180 Properties

20:08 - Why They Do All Maintenance In-House

25:38 - How AI Automated 70% of Guest Communication

29:54 - From Signed Contract to Live Listing in 7 Days

31:18 - How to Choose Markets Based on Regulatory Stability

36:49 - Why Aidan Is Selling His Portfolio to Bet on the Management Company

40:41 - The Real Cost of Building This Business

43:59 - The Future: 350+ Units and Acquiring Smaller Operators

47:15 - Aidan's #1 Secret to STR Success

Connect with Aidan:

Instagram: https://www.instagram.com/aidangroll/

LinkedIn: https://www.linkedin.com/in/aidan-groll

Email: aidan@bluegems.group

📲 Connect with STR Secrets:

Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

STR Secrets Podcast: https://strsecrets.com/podcast

If you want to increase your revenue, automate your day to day operations and spend more time with your kids: http://strsecrets.com/apply

If you want to join these live trainings:

https://www.facebook.com/groups/STRentalsecrets

This is the first episode of the STR Portfolio Clinic. A brand new series where me and Mike Sjogren pull up real STR listings on screen and diagnose what's working and what's not. Live. In front of everyone. No filter.

This episode is all about listings.

We reviewed two real Airbnb properties from operators who volunteered to put their listings on the hot seat.

First up is a brand new beach cottage in Oak Island, North Carolina. Second row from the ocean. Clean listing. But nobody's clicking on it. We broke down why and gave the owner a full game plan on the spot.

Then we pulled up a riverfront property in Murphy, North Carolina. Fly fishing right off the deck. Beautiful area. Went an entire summer with zero bookings. It took about 10 seconds to see what was wrong.

We also break down the ALE framework which stands for amenities, location, and experiences. This is the framework behind how we build listings across 30+ properties that generated over $5M in bookings last year.

If your listing has been sitting or your bookings have slowed down, this episode will show you exactly what to fix and in what order.

Want your listing or business reviewed on a future episode? Drop CLINIC in our DMs

TIMESTAMPS:

0:00 - What is the Portfolio Clinic

0:55 - The ALE Framework: Amenities, Location, Experiences

4:17 - Listing Review #1: Beach Cottage in Oak Island, NC

5:09 - Photo feedback: It's clean but it's too white

6:31 - How to use AI for sunset and lifestyle shots

7:15 - Staging amenities: Reilly's beach property example

8:41 - Who's your avatar and why it changes your photos

9:12 - Sjogren: The wizard room hero image strategy

10:33 - Using ChatGPT to create twilight shots

11:38 - Interior updates vs working with what you have

12:47 - Getting five star reviews on a new listing

13:52 - The combined listing strategy for side by side properties

16:58 - Aerial shot hack to show both properties

17:48 - Listing Review #2: Riverfront A-Frame in Murphy, NC

18:16 - Sjogren's first reaction: "I don't love this first photo"

19:04 - Andy's story: Zero bookings since launch

19:56 - Why you need to relaunch dead listings

20:35 - Phone photos are killing your listing

21:24 - What lifestyle photos this property actually needs

22:47 - Comp analysis: What top properties in Murphy look like

25:02 - Brutal feedback: The photos make it look dark and dated

26:35 - Staging the deck and outdoor space

28:41 - The game plan: Photos, relaunch, pricing, reviews

29:42 - The Airbnb new listing push and why Andy missed it

30:09 - Small changes that pay for themselves in one night

30:47 - Insurance and liability for offering amenities

33:23 - Bonus: Quick review of Christie's listing

35:40 - What's coming next and the Freedom Factory event

Most people end Q1 the same way they started it.

Behind on goals. Ahead on excuses.

In this solo episode, E breaks down why that happens — and what to actually do about it before Q2 starts.

This isn't a motivational pep talk.

It's a direct, honest look at the real reason you keep self-sabotaging — even when you know exactly what you need to do.

In this episode, E covers:

- Why the brain doesn't perceive time as time — and what that means for how you're living

- Tony Robbins' 3 S's framework: State → Story → Systems (and why you're skipping the first two)

- The 5 core wounds that create self-sabotage: rejection, abandonment, humiliation, betrayal, and injustice

- The difference between being self-centered vs. self-aware — and why it changes everything

- The belief thermostat: why you always reduce yourself back to what you think you're worth

- 3 questions to ask yourself right now as you close out Q1

- The one question E asks himself that "terrifies the shit out of him" — and keeps him moving

If the year hasn't gone the way you planned — this episode is the reset you need.

📲 Connect with STR Secrets:

Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

Apply to work with us: https://strsecrets.com/apply

STR Secrets Podcast: https://strsecrets.com/podcast

Timestamps:

0:00 - Intro

2:09 - Q1 Check-In: Are You Still Holding Your Standards?

3:57 - Why Time Feels Like It's Running Away (The Science of Memory Markers)

6:13 - Stop Just Learning — Start Experimenting

7:13 - Tony Robbins' 3 S's: State, Story, and Systems

9:23 - Why Mindset Work Alone Keeps Failing You

9:47 - The 5 Core Wounds Behind Every Self-Sabotage Pattern

11:23 - How Your Brain's 3 Layers Are Keeping You Stuck

13:38 - Self-Centered vs. Self-Aware: The Shift That Changes Everything

15:37 - The Belief Thermostat: Why You Keep Reducing Yourself

17:05 - Your Honest Q1 Review: Facts Only, No Stories

18:38 - 3 Questions to Ask Yourself Before Q2 Starts

20:33 - Nobody Is Coming to Save You

22:56 - "Is This the Final Version of You?"

Check out our free 6 step course: https://level.strsecrets.com/pc-book

If you want to join these live trainings:

https://www.facebook.com/groups/STRentalsecrets

If your listings aren't getting booked right now — don't panic and drop your prices.

In this week's Thursday training, Mike Reilly sits down with Maryann Wahhab, revenue management expert and STR operator across 6 states, to break down exactly what's working right now to get booked at the rates you want.

Maryann went from college basketball coach to full-time STR revenue manager — and now helps operators stop leaving money on the table in soft markets.

In this episode, Mike and Maryann cover:

- Why your slow bookings are probably a listing problem — not a pricing problem

- The booking window zones every operator needs to understand (and how to price each one)

- How Mike went 30% up year over year on Vrbo with one simple OTA trick

- The "booking velocity" metric Maryann tracks at 7, 15, and 30-day marks

- How a listing went from page 6 to page 2 on Airbnb in one week

- Why virtual stays are a game changer for dead listings

- The full listing re-optimization playbook for properties with no bookings in 30+ days

- How to use Airbnb's rule sets and length-of-stay discounts to capture more revenue in slow season

This is the training your listings need right now.

---

🎙️ About Maryann Wahhab:

Maryann is a revenue management expert and STR operator managing properties across 6 states. A former Division I basketball coach, she left the game in 2023 to manage properties full-time — and now helps STR operators maximize revenue in any market condition.

---

Timecodes:

0:00 - Why Your Listings Aren't Getting Booked Right Now

2:30 - Meet Maryann Wahhab: From Basketball Coach to STR Expert

6:00 - How to Read Your Market Before You Touch Your Prices

10:00 - Booking Window Zones Explained (And How to Price Each One)

15:30 - Booking Velocity: The Metric That Tells You When to Act

20:00 - How to Play the Airbnb and Vrbo Algorithm Game

25:30 - The OTA Trick That Got Mike 30% Up Year Over Year on Vrbo

30:00 - Virtual Stays and How to Reinvigorate a Dead Listing

36:00 - The Full Re-Optimization Playbook for Struggling Listings

41:30 - Length-of-Stay Discounts and Airbnb Rule Sets in Slow Season

46:00 - How to Differentiate Your Listing So You're Never in a Price War

Instagram: https://www.instagram.com/sean_bakhtiari/

Check out Seacoast 2 Summit: https://www.seacoast2summit.com

Check out our free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

What happens when a corporate finance guy from Boston decides he's done working for someone else — and bets on short-term rentals?

Sean Bakhtiari is the co-founder of Seacoast 2 Summit Vacation Rentals and The Bakhtiari Group, a top-performing real estate sales team across Massachusetts, New Hampshire, and Maine. As an active STR investor, his work sits at the intersection of real estate, hospitality, and investment strategy throughout New England.

After 9 years in Boston's financial district, Sean bought his first STR. Then a second. Then started building a management company.

At 12 properties, he hit a wall. He was good at business development and client relationships. But systems, operations, and scale? Not his strengths. That's when a serendipitous call from Chris changed everything.

Today, Sean and Chris co-run Seacoast to Summit Vacation Rentals — managing 120+ properties across the New Hampshire seacoast, lakes and mountains region, and North Shore of Massachusetts. Almost entirely on referrals, with virtually no paid marketing.

In this episode, Sean and Chris pull back the curtain on:

- How they identified each other as the right partner (and what 3 things you need to align on before you sign anything)

- Sean's "help first, never sell" philosophy — and why it's responsible for most of their growth

- Why they've said no to 10+ deals in the last 3 months (and why that's the right call)

- The two fears they stay up at night thinking about as they scale

- How to delegate without feeling like you're losing control

- What it takes to keep your team culture intact as you grow

- Why boutique hotels might be the next frontier for this business

This is a rare episode — a founder bringing on his business partner and pulling off the veil on how a real, values-driven STR company actually works at scale.

---

Timestamps:

0:00 - Introducing Sean Bakhtiari: Chris's Business Partner

2:45 - How Sean Went From Corporate Finance to STR Management

6:30 - Building Seacoast to Summit: From 12 to 120 Properties

10:15 - How Sean and Chris Found Each Other (The Serendipitous Call)

15:00 - The 3 Things You Must Align On Before Partnering

18:30 - The "Help First" Sales Mindset That Built the Business

23:00 - Why They Said No to 10 Deals in 3 Months

27:00 - The Two Fears They Have About Growing Too Fast

32:30 - How to Delegate Without Losing Control

37:00 - Keeping Team Culture Intact at Scale

42:00 - What the Future Looks Like: Boutique Hotels and Brand Building

46:00 - Sean's #1 Secret to STR Success

Instagram: @jeremiahkwatson

Business: www.affluentvacays.com

Check out our free 6 step course: https://level.strsecrets.com/pc-book

STR Secrets FB group https://www.facebook.com/groups/STRentalsecrets

He did everything people told him to do.

Got clean. Went to college. Got a good job. Made good money.

And he was still unhappy.

In this episode, we talk with Jeremiah Watson. Jeremiah just quit his corporate job. He now runs an 18-property cohosting business in Los Angeles. He is the 73rd person to leave their job through STR Secrets.

Here's what you'll learn:

→ How Jeremiah went from addiction and jail to building a real business

→ Why he lost $50K his first year — and what he changed

→ How he got his first cohosting deal with one cold call

→ The small team that runs his business today

→ His goal: 66 properties by the end of 2026

This is what actually doing the work looks like.

Timestamps:

00:00 - Who Is Jeremiah Watson?

03:12 - From Addiction and Jail to Turning His Life Around

08:11 - Why He Chased the Corporate Dream

11:36 - He Tried STRs and Lost $50K in Year One

13:16 - How He Found Cohosting and Got His First Deal

16:36 - How He Grew From 1 to 18 Properties

19:11 - His Team and How the Business Runs Today

21:27 - His Big Goal: 66 Properties by End of 2026

22:45 - What to Do If You Have a Job and No Time

27:06 - How to Balance Drive With Gratitude

31:57 - Why This Business Is About More Than Money

It’s about building the team that can support the growth.

In this episode, Chris and E sit down with Alex Hall — talent advisor and leadership strategist — to break down the real challenges STR operators face when building teams.

From job clarity and org structure to burnout, hiring, and leadership development, Alex shares the frameworks that help operators scale from a handful of listings to a real company.

If you're trying to grow beyond the stage where you do everything yourself, this episode is a masterclass in leadership and people management.

Inside this episode:

• Why most STR companies don’t actually know who reports to who

• The biggest hiring mistake operators make while scaling

• How to structure a team from 10 to 100+ listings

• Why burnout happens during fast growth

• The leadership habits that retain great talent

• When to introduce equity or long-term incentives

If you want a real business — not just a portfolio of properties — it starts with leadership.

Guest Bio:

Alex Hall is the founder of Valinor Talent Solutions, where he serves as a fractional HR executive helping growing companies build strong people strategies, leadership development, and scalable teams. With over a decade of experience in talent and organizational development, he partners with businesses to create high-performing workplaces. Alex works with short-term rentals to develop their talent strategy so they can focus on delivering exceptional guest experiences through thoughtful design, strong systems, and hospitality-driven service.

Guest Contacts:

alex@valinortalent.com

www.valinortalent.com

Get FREE Access to our 6 STEP course:

https://www.strsecrets.com/podcast

Timestamps:

00:00 – Why Most Teams Don’t Know Their Role

02:00 – Success, Identity, and Leadership Growth

04:30 – Introducing Alex Hall: Talent Advisor for STR Operators

07:25 – When STR Businesses Actually Need HR Support

09:20 – The 3 Levels of Team Structure as You Scale

12:40 – The Most Common Hiring Problems in STR Companies

14:00 – Why Job Clarity and Accountability Are Missing

17:10 – The 33% Rule: When Leaders Outgrow Their Team

20:05 – Burnout Signals Every Operator Should Watch

23:20 – Building Org Structures for 10–100 Listings

26:00 – Why Systems Matter More Than Org Charts

27:00 – How Great Leaders Reward and Motivate Teams

30:00 – Equity vs Performance Bonuses for Key Employees

33:00 – The 3 Rules of Leadership: Clear, Kind, Respectful

36:10 – Leadership Lessons for First-Time Founders

39:50 – AI’s Role in Future STR Operations

42:40 – Final Advice for Building a Great STR Team

Instagram ➡️ https://www.instagram.com/mikereillync/

Follow this link for the Free training:

https://level.strsecrets.com/pc-book

You want to grow a property management business, you will eventually hit the same wall:

You become the person slowing things down.

In this video, I share the exact playbook we built before hiring our first salesperson.

Inside this training you’ll learn:

• The perfect type of property we target

• The exact type of homeowner we want to work with

• The biggest problems Airbnb owners face today

• How we show our value to sign new clients

• The "UI Method" for finding struggling Airbnb properties

• The exact numbers and goals we set for our sales team

• The best ways we find and talk to new owners

• Our step-by-step sales process and first phone calls

• What happens right after an owner signs with us

If you want to grow your company to 30, 40, or 50+ properties, you need a sales plan that works every single time.

This episode shows you exactly how we built ours.

Subscribe for new weekly videos ➡️ https://bit.ly/2Nrn4XO

Timestamps:

00:00 – Why You Need a Sales Plan

01:12 – The 4 Steps of Our Sales Playbook

02:10 – Finding the Perfect Property

03:05 – The Perfect Homeowner

04:18 – Problems Airbnb Owners Face

05:45 – Creating a Strong Offer

07:00 – Why You Need a CRM Software

08:50 – Sales Goals and Numbers to Track

10:20 – The Experiment: 120 Calls in 6 Weeks

11:35 – Our Sales Win Rates

12:18 – How to Find Leads: The UI Method

13:30 – Using Referrals and Partners

14:05 – Direct Mail and Ads

15:05 – Running Facebook Ads for Leads

16:10 – Our Sales Process

17:20 – The First Call and Asking Questions

18:15 – Handling Owner Concerns

19:05 – Bringing on a New Owner

20:00 – Weekly Sales Tracking

21:10 – Hiring and Testing a Salesperson

Connect with us on other social media platforms:

STR Secrets FB group ➡️ https://www.facebook.com/groups/STRentalsecrets

Michael Sjogren FB Page ➡️ https://www.facebook.com/theAirbnbGuy

Instagram ➡️ https://www.instagram.com/miike.sjogren

Linkedin ➡️ https://www.linkedin.com/in/mikesjogren

Then 2008 hit.

Reserves drained.

Assets liquidated.

Eventually — bankruptcy.

Most investors never come back from that.

In this episode, Jon St. Leger breaks down:

• What the 2008 crash really felt like

• Why he keeps his portfolio at 33% LTV

• How to prepare for the next recession

• What “Equity Manifestation” actually means

• How he turned a 20-room motel into a 47-key boutique hotel

• Why delayed gratification builds real wealth

• The blue-collar advantage most people ignore

Jon now owns 13+ short-term rentals, long-term rentals, and is breaking ground on a beachfront boutique hotel in the Outer Banks.

If you’re serious about building generational wealth in real estate — this one is different.

Follow Jon on Instagram: @jon_boy14

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

TimeStamps:

00:00 – Equity Manifestation & The $100M Vision

02:00 – Identity, Mindset & Future Self Thinking

05:30 – From Blue Collar Beginnings to Construction Company

09:45 – Building a Portfolio… Then 2008 Hit

12:30 – The Mental Toll of Bankruptcy

14:45 – Lessons From the Crash: Reserves & Exit Strategies

17:00 – Why He Keeps 33% Loan-to-Value

19:00 – Not Overleveraging in Growth Cycles

21:30 – From STR Portfolio to Boutique Hotel Developer

24:00 – Turning a 20-Room Motel into 47 Keys

27:00 – Getting Town Buy-In & Emotional Attachment

30:00 – Leading Teams & Maintaining Morale

32:30 – The Power of Delayed Gratification

35:00 – Return on Sweat Equity (R.O.S.E.)

37:00 – Blue Collar Wealth Strategy

39:00 – The $100M Real Estate Target

41:00 – Where Opportunity Lives & Final Advice

Supply is rising.

Middle-class travel is tightening.

Occupancy is projected to decline.

Rates are compressing.

If your Airbnb still looks like 2024… you're in trouble.

In this training, I break down my full 4-step photography system:

– What to upgrade BEFORE hiring a photographer

– How to properly interview lifestyle photographers

– What to do on photo day to maximize impact

– How we use AI to write captions and enhance photos

– How we organize everything inside our operating system

If you’re scaling a property management or co-hosting business, this is not optional anymore.

Timestamps:

00:00 – Why 2026 Will Be Harder for STR Operators

02:12 – Supply Is Rising, Occupancy Is Falling (The Reality Check)

03:30 – Step 1: Refresh Before You Photograph

06:10 – Using ROI Analysis to Justify Property Upgrades

09:20 – Real Estate vs Lifestyle Photography (Huge Difference)

12:05 – What Elite STR Photos Actually Look Like

16:00 – How to Properly Interview a Photographer

19:10 – Photo Day Execution: Staging That Converts

22:15 – Organizing Photos for Scalable Operations

25:00 – Using AI to Write Captions for Every Photo

27:00 – Editing & Enhancing Photos with AI

29:15 – The Freedom Operating System Explained

32:00 – How to Scale Photography Across Multiple Listings

34:15 – Mastermind, CRM, and 2026 Growth Strategy

36:50 – Final Advice: Upgrade or Get Left Behind

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

They don’t.

In this Boardroom recap from the Freedom Factory, we unpack the real reasons businesses stall — and it’s not systems.

It’s people, identity, and the state you operate from.

Inside this episode:

• Why most business bottlenecks are solved by the right “who”

• The difference between hiring people and developing talent

• W2 vs 1099 mistakes operators make

• Why State → Story → Strategy is the real order of success

• The 4 archetypes running your decisions (Warrior, Magician, Lover, Sovereign)

• Why high performers get stuck in Warrior mode

• How seasonality applies to your business and your life

• Why kindness to yourself is a competitive advantage

If you feel like something is holding you back… this episode will hit.

Timestamps:

00:00 – Boardroom at the Freedom Factory Recap

02:15 – From Cooked Books to 80,000 Meals a Week

04:10 – Visionaries Get Small When Stuck in Operations

05:45 – The “Right Who” Solves Most Bottlenecks

07:50 – Building Talent Structure (Not Just Hiring)

10:40 – W2 vs 1099: What Operators Must Understand

12:20 – The 3 S’s of Breakthrough: State > Story > Strategy

15:05 – The 4 Archetypes Running Your Life

18:30 – Warrior Mode & The Seasonality of Growth

21:10 – Kindness, Presence & The Power of Awareness

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, she breaks down how she pivoted during the pandemic, why most investors don’t have enough grit, and how mastering calendar discipline can completely transform your rental income.

We dive into:

• Why community changes everything in real estate

• The biggest mistake STR hosts make when pivoting to midterm rentals

• Calendar discipline and how to control guest behavior

• How to use data tools like PriceLabs the right way

• Building multiple income streams without burning out

• Protecting your time while scaling a real estate business

If you’ve been feeling stuck, burned out, or uncertain about the next step in your rental business — this episode will challenge you to think differently.

Timecodes:

00:00 – Intro

03:12 – Why Community Is a Competitive Advantage

05:00 – The Power of Grit in Business

07:02 – Vivian’s Real Estate Journey (2004–2018 Gap Explained)

09:56 – Corporate Burnout at Apple & Transferable Skills

13:05 – Why Most Investors Pivot Too Fast

16:48 – Why Midterm Rentals Make More Strategic Sense

21:41 – The Calendar Discipline Most Hosts Ignore

25:31 – Transitioning from STR to MTR the Smart Way

30:29 – Why Vivian Built Her Own Platform

35:07 – Building Teams Without Burning Out

38:10 – Setting Boundaries & Protecting Your Time

42:05 – The 80% Confidence Rule (Just Do It)

Guest Bio:

Vivian Yip started investing in 2004 but took her journey more seriously after being inspired by a hotel owner she met at a random airport encounter in Chicago. She and her husband started to flip houses in 2018 and ended up making enough to afford to keep the real estate. She always dreamed of leaving the corporate world, so she used her steady paycheck at Apple to support their real estate goals. In 2019, she started her first short-term rental and was forced to pivot in 2020 with the pandemic. Now she runs multiple businesses focused on short-term rentals, mid-term rentals, and corporate housing, and she coaches others on the strategy behind securing profitable leases from Airbnb and beyond.

Guest Link:

Instagram.com/vivianyip_official

vivian@vivianyip.com

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, Madison Rifkin breaks down what actually works when partnering with content creators, why follower count is a useless metric, and how STR operators should think about social media as a long-term control channel — not a quick ROI play.

We also go deeper into founder identity, building brands that can be sold, and the mistakes operators make when they tie everything to themselves.

If you want more direct bookings, stronger brand trust, and a business that isn’t dependent on Airbnb alone, this episode is required listening.

Inside the episode:

• Why follower count doesn’t matter anymore

• How to vet influencers the right way

• The real way to think about ROI from content creators

• Why social media is your only true control channel

• Content ideas that work even without a “viral” property

• Founder identity mistakes that kill exits

• How to build a brand that survives without you

Timestamps:

00:00 – Why Influencer Marketing Is Broken for Most STR Hosts

03:20 – Madison’s Journey Building Mount and Entering STRs

06:40 – Why Follower Count Is a Terrible Metric

10:10 – How to Vet Influencers Based on Brand Alignment

13:30 – The Truth About ROI in Influencer Marketing

17:10 – Why Social Media Is a Control Channel, Not an Ad

20:00 – Content That Works Without a “Viral” Property

23:10 – Founder Identity and Why It Hurts Exits

26:30 – Building a Brand That Isn’t Tied to You

30:45 – Lessons From Selling a Company and Starting the Next Chapter

Guest Bio:

Madison Rifkin is the Founder and CEO of Mount where she finds the world's best hidden gems. She connects STR hosts and local businesses to local influencers and travel content creators so travelers can discover these hidden gems. She’s rooted in the Short Term Rental Industry where she’s won the Rising Star Award in 2022 and 2023.

Guest links:

https://www.linkedin.com/in/madison-rifkin-23037712a/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, we sit down with Hayley Anderson, a 22-year-old operator already on her second business, to unpack the mindset, discipline, and leadership traits that actually drive growth. From failing early to building confidence through reps, this conversation goes far beyond arbitrage or co-hosting.

If you want to scale your business — or your life — this episode will challenge how you think about comfort, confidence, and commitment.

Inside the episode:

• Why conviction matters more than experience

• How confidence is built through reps and failure

• The leadership habit that quietly builds culture

• Why comfort is the enemy of growth

• Learning to bet on yourself before results show up

• Applying mindset across business, relationships, and life

Timestamps:

00:00 – Intro

04:20 – Hayley’s Early Hustle and Second Business at 22

08:10 – Confidence Is Built Through Reps, Not Motivation

12:30 – Failing Early Without Letting It Define You

16:40 – Comfort vs Growth: The Tradeoff Most Avoid

20:15 – Leadership Starts With Small Cultural Habits

24:35 – Betting on Yourself Before Results Show Up

29:00 – Applying Mindset Across Business and Life

33:40 – Why Age, Model, and Capital Matter Less Than Belief

38:10 – The One Trait That Predicts Long-Term Success

Guest Bio:

Hailie Maarie Anderson is a 22 year old short term rental host operating over 70 rentals across three markets, all run 100% remotely through a blend of technology and teams.

While scaling her own portfolio, she has taken the stage at industry events to share her systems and insights, and has successfully coached over 1,300 individuals to start and scale their own short term rental businesses. Hailie’s mission is to be a leading voice for those who want to build and live an unconventional life, one without limits!

Guest Link:

https://www.instagram.com/hailiemaarie/?hl=en

https://www.tiktok.com/@hailiemaarie

https://youtube.com/@hailiemaarie?si=3qCgG6OPXqwZTgU2

https://www.linkedin.com/in/hailie-maarie-4b20a5276/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, we break down AirDNA’s 2026 outlook and translate the data into real, tactical decisions for hosts and property managers. Demand is softening, supply is shifting, and average properties are losing ground — but operators who adapt will win.

This is a data-backed walkthrough of what’s changing, why it matters, and exactly what to do next.

If you want the Training on how you should look at increasing your pricing so that you are not making 15 to 18% less than you were a year over year just click the link and DM "FEE".

https://ig.me/m/mike.sjogren?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T035&utm_content=FEE

Inside this episode:

• What AirDNA’s 2026 data actually says about demand and supply

• Why average properties will lose occupancy and revenue

• The markets and property types positioned to outperform

• How to talk homeowners into smart upgrades (with ROI)

• Why property managers are pulling ahead of solo hosts

• Using AI and systems to protect reviews and prevent burnout

00:00 – What the 2026 STR Outlook Means for Hosts & Property Managers

03:30 – Why STR Supply Has Flattened (And Why That Matters)

06:10 – Demand Is Softening: The Economic Reality Hosts Must Accept

09:15 – Average Properties Will Lose Occupancy in 2026

12:00 – Why Larger, Luxury Properties Are Winning Again

15:00 – Shedding Low-Performing Properties to Refocus Growth

18:20 – Coastal & Urban Markets: Where Smart Money Is Moving

21:00 – How to Sell Homeowners on Strategic Property Upgrades

24:30 – Property Managers vs Solo Hosts: The Performance Gap

27:40 – AI, Systems, and the Only Way to Scale Without Burning Out

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, we break down what actually changes when you go from being a solo operator to leading a real team. From earning respect instead of demanding it, to building systems that support people (not suffocate them), this conversation unpacks the leadership shifts required to scale without chaos.

If you’re growing doors, people, or partnerships — this episode will change how you think about leadership.

Inside the episode:

• The two ways leaders earn respect (and why only one works)

• Why supporting team members’ goals makes you more valuable

• How ego quietly slows down growth

• Leading teams through systems, not micromanagement

• What it really takes to earn buy-in as a leader

• Why consistency beats motivation when scaling

00:00 – The Two Ways Leaders Show Up (Title vs Example)

04:10 – Why Supporting Team Growth Makes You More Valuable

08:05 – From Solo Operator to Leading People

12:30 – Letting Go of Ego to Scale Faster

16:05 – Earning Respect Without Authority

20:10 – Using Systems to Reduce Team Burnout

24:05 – Aligning Company Goals With Personal Goals

28:00 – Consistency Over Motivation in Leadership

32:10 – Scaling Teams Without Losing Culture

36:20 – The Leadership Standard That Sustains Long-Term Growth

Guest Bio:

Ryan Leake, originally from Mill Valley, CA, moved to Austin, TX in 2023, where he left corporate America and founded Host Del Casa, a short-term rental management company.

After successfully building the business, Host Del Casa merged with Five Star Vacation Home Rentals (FSVHR), where Ryan now serves as a Managing Partner for the #1 luxury short-term rental management company in Central Texas - managing 60+ luxury short-term rental properties across Austin and San Antonio.

In addition to his role at FSVHR, Ryan became a coach and consultant for STR Secrets, the leading short-term rental business coaching program, where he helped operators overcome self-limiting beliefs and build profitable, lifestyle-driven STR businesses.

Today, Ryan continues to coach and mentor new short-term rental operators, share insights as a thought leader in the space, and prioritize a life designed around freedom, impact, and balance.

Guest Link:

www.instagram.com/itsaleake

ryan-leake.com

fivestarvhr.com

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, Frank Bosi (Hostfully) joins the show to unpack the real challenges STR leaders face as they scale—pressure, decision fatigue, emotional weight, and the constant tension between automation and hospitality.

Drawing from years inside luxury hotels like Ritz-Carlton and Four Seasons, Frank breaks down what most operators get wrong about tech stacks, leadership, hiring, and guest experience—and how to build systems that create confidence instead of doubt.

Inside this episode:

1. Why tech stack decisions are emotional, not logical
2. How disconnected tools quietly create leadership stress
3. The difference between automating tasks vs removing hospitality
4. What luxury hotels get right about training and consistency
5. Why leaders must absorb pressure instead of passing it down
6. How to hire people who protect your brand when you’re not watching

This is a must-listen for any STR operator building a team, scaling systems, or feeling the weight of leadership.

00:01 – Why Tech Stack Decisions Are Emotional, Not Logical

03:45 – Automation vs Hospitality: Where Operators Go Too Far

07:10 – The Weight of Leadership Most People Aren’t Ready For

11:00 – Why Disconnected Tools Create Doubt and Stress

15:20 – Lessons STR Operators Can Steal From Luxury Hotels

19:10 – Why Leaders Can’t Have “Bad Days” Publicly

23:30 – Hiring People Who Protect Your Brand When You’re Not There

27:40 – Training, Standards, and Why Consistency Beats Luxury

31:50 – Using Tech to Create Confidence, Not Complexity

36:40 – The Real Role of a Leader in Scaling STR Operations

Guest Bio:

Frank Bosi is the Senior Director of Partnerships at Hostfully, a leading platform supporting short-term rental operators around the world. He drives strategic relationships across the STR ecosystem; working with technology partners, influencers, coaches & thought leaders to help property managers scale and deliver great guest experiences.

Frank also actively contributes to industry conversations through webinars, events and podcasts (such as this) designed to help operators grow smarter, faster, and more profitably.

Outside of work, Frank prioritizes faith, fitness, and family; spending his free time with his wife and kids, training CrossFit, and staying focused on overall wellbeing.

Guest Link:

https://www.instagram.com/frank_bosi/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, E and Chris break down why most people start the year motivated… then quietly drift back into old patterns. The problem isn’t strategy, tools, or ambition — it’s misalignment between who you say you want to become and how you actually spend your time.

This conversation dives deep into identity, courage, time audits, consistency, and the hidden habits that either compound your growth or quietly sabotage it.

Inside this episode:

1. Why your calendar tells the truth about your real priorities
2. The “perfect week” exercise that exposes misalignment fast
3. Why every new level requires letting go of your old identity
4. How fear, comfort, and ego silently slow your progress
5. The power of small, consistent actions over big intentions
6. Why courage often means saying “no,” not “yes”

If you’ve ever felt busy but stuck — this episode will hit home.

00:00 – Why New Year Motivation Dies Faster Than You Expect

02:05 – The Reality Check: When Goals Collide With Real Life

04:20 – The Calendar Test: Do Your Actions Match Your Goals?

07:40 – Designing Your “Perfect Week” (And What It Exposes)

10:55 – Your Dreams Are Expensive — Here’s the True Cost

14:30 – Killing the Old Version of Yourself to Level Up

17:55 – Faith vs Fear: Making Decisions Without Freezing

21:30 – Small Habits That Quietly Compound Massive Change

25:10 – Letting Go of Ego to Create Space for Growth

29:05 – Enjoyment, Consistency, and Becoming Your Best Self

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, we break down what actually separates top-performing short-term rentals from the ones stuck in the middle. From design and amenities to operations, leadership, and systems—this is a real look at how elite STR businesses are built and sustained in hyper-competitive markets.

This isn’t theory. It’s what’s working right now.

Inside this episode:

- Why “good enough” STRs are getting crushed

- The amenity arms race (and how to win without wasting money)

- What guests notice that most hosts completely miss

- How ops and hospitality matter more than design long-term

- Why disciplined systems protect profit—even in down years

- The leadership mindset required to scale without chaos

If you want longevity in this industry, this episode is required listening.

00:06:15 – Becoming “The Guy” in a Hyper-Competitive STR Market

07:45 – Why Copying Competitors Is a Losing Strategy

09:15 – The New Minimum Standard for STR Design & Amenities

11:40 – Why Half-Upgraded Properties Always Underperform

18:50 – The Amenity Arms Race: What Actually Moves Revenue

20:00 – When Design Stops Mattering and Ops Take Over

26:10 – Building Teams and Systems That Don’t Break Under Stress

30:45 – Leadership Lessons from Military and STR Operations

34:05 – How Efficiency Protects Profit in Down Revenue Years

39:35 – The Long-Term STR Play: Scale, Discipline, and Longevity

Guest Bio:

Shane O’Connor is the CEO & Founder of Alchemy Real Estate & Alchemy Hosting. Alchemy is based in Tampa, FL, building a portfolio of Short-Term Rental assets primarily focused in Central Florida. By delivering vertically integrated, top-tier service from beginning to end in the investment process, Alchemy has grown from a single property (and single employee) to 11 properties & a team of four in less than a year. In that same time, Alchemy will have also delivered more than $3M in closed real estate deals for its clients.

By the end of 2022, it is Shane’s goal to have a blended Direct Ownership & Co Hosting portfolio of 30 properties centered in Florida, to then begin expanding to other markets. Shane is a graduate of the United States Naval Academy and served as an Officer in the U.S. Navy for 9 years. He received an M.S. Degree in Real Estate from the University of Florida. He runs the company with his brother, Captain Devin O’Connor, who is an active duty Marine Corps helicopter pilot in addition to being the Director of Operations for Alchemy.

Guest Link:

https://www.instagram.com/oc_dreams19/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, Chris and E break down why goals alone don’t create change, how identity drives momentum, and the real reason most people stall out by February. This is a deep, practical conversation on discipline, accountability, emotionalized goals, and how to build habits that actually stick.

If you’ve ever felt stuck despite “doing all the right things,” this episode will reframe how you think about growth — personally and professionally.

Inside this episode:

• Why identity matters more than motivation

• How emotionalized goals create automatic discipline

• The “never two days in a row” rule that builds momentum

• Why most people sabotage themselves without realizing it

• How to design accountability that actually works

• Turning small daily actions into long-term transformation

👉 If this episode resonated, share it with someone who’s setting big goals this year — and subscribe for more real conversations on growth, leadership, and execution.

00:00 – Why the Point of a Goal Is Growth, Not the Outcome

02:05 – Identity vs Outcomes: The Real Way to Set Goals

04:20 – Emotionalizing Goals to Create Immediate Action

06:10 – Going Deeper on “Why” Using the Seven Layers Exercise

08:35 – Shifting from “I Have To” to “I Get To”

10:15 – Building Momentum with Small, Non-Sexy Wins

12:40 – Vision First: Thinking Big Enough for the Next Level

15:05 – Quarterly Sprints and the Power of the 12-Week Year

17:40 – Time Blocking Life, Family, and Business (In That Order)

20:30 – Accountability, Never Missing Twice, and Staying in Motion

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, Stacey St. John breaks down how self-awareness, intuition, mindset, and values-driven leadership shape long-term success in business and life. From recognizing limiting beliefs to building aligned teams and managing energy, this conversation goes far beyond surface-level motivation.

If you’ve ever felt stuck, overwhelmed, or pulled in too many directions — this episode explains why and what to do about it.

Inside this conversation:

1. How intuition and body awareness guide better decisions
2. Why identity drives action (and keeps people stuck)
3. The difference between excitement and misalignment
4. How to hire and lead based on values, not resumes
5. Practical mindset tools to reset stress and overwhelm
6. Why self-image and internal stories affect performance
7. How high performers accept feedback without ego

00:00 – Why Most Entrepreneurs Stay Stuck (It’s Not Strategy)

03:45 – Introducing Stacey & Why Mindset Drives Everything

07:20 – Front Pocket vs Back Pocket Decisions Explained

10:50 – Learning to Trust Intuition Without Second-Guessing

14:30 – Energy, Stress, and Showing Up as a Leader on Bad Days

18:10 – Building the Right Team: Values Over Skills

22:40 – Why Misaligned Hires Quietly Kill Momentum

27:05 – Identity Shifts Required to Reach the Next Level

31:20 – Rewriting Internal Stories That Limit Growth

35:50 – Integrating Mindset Work Into Daily Business Life

Guest Bio:

Stacey St. John is a visionary real estate entrepreneur who is reshaping the short-term rental industry for women on Airbnb. She founded the Female Short-Term Rental Investors Facebook Group, The STR Sisterhood, and The Short-Term Rental Virtual Summit for Women. Stacey began her short-term rental journey on Airbnb in 2020; she quickly realized the industry’s potential and the opportunity to empower women through real estate investing to help them create successful, profitable “Airbnb businesses.” She has since built a 7-figure portfolio and left her corporate career to focus on her mission. Stacey is a strong advocate for women in business and is committed to creating a more equitable and inclusive industry. She is a frequent speaker at short-term rental and Airbnb industry events and is a regular contributor to industry publications.

Guest Link:

https://www.instagram.com/stacey_st.john/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, Chris and E sit down with Shahar Goldboim, founder of BOOM, to break down how AI is fundamentally changing short-term rental operations, exits, and scale.

From selling a property management company to building tech that replaces broken workflows, this conversation dives deep into why fragmented tools are failing and why operators who don’t adapt will fall behind.

Inside this episode:

• Why “tech-enabled” STR businesses still fail
• The biggest mistakes operators make when exiting
• Why one company can’t do funds, PM, design, and tech well
• How AI eliminates 80% of guest communication (without killing hospitality)
• Why fragmented STR software stacks are breaking ops
• How AI becomes the new infrastructure for scale

00:00 – Why Solving Everything Breaks Most Tech-Enabled STR Companies

03:05 – “Business as a Service” vs Traditional STR Software Stacks

06:20 – From Operator to Platform Builder: Shahar’s Real Estate Path

10:10 – Why Tech-Enabled PMs Fail Without Focus

14:30 – The Hidden Cost of Fragmented PMS + Tools

18:05 – Why AI Fails Without Full Operational Data

22:40 – How AI Can Eliminate 80% of Guest Communication

27:15 – The Real Bottleneck: Scaling Ops, Not Software

32:10 – Why All-in-One STR Platforms Are the Future

38:20 – The Direction of AI, Automation, and STR Businesses

Guest Bio:

Shahar Goldboim is the Co-Founder and CEO of Boom, the world’s first Autonomous Property Management System (AiPMS)—a platform redefining how real estate assets are operated through AI. Before founding Boom, he built DesignedVR, a hospitality management company overseeing more than $150 million in assets. This extensive experience gave him a firsthand understanding of the intricate, day-to-day challenges property operators face.

Throughout his career, Goldboim has been involved in hundreds of millions of dollars in real estate transactions as an investor and broker, and has deployed over $50 million in syndication funds. That deep operational and financial experience shaped his belief that the future of property management lies in automation, intelligence, and human-centered design.

Today, Boom merges hospitality, real estate, and AI to help operators around the world manage smarter, scale faster, and unlock the full potential of their assets.

Guest Link:

https://www.linkedin.com/in/shahar-goldboim-80820b95?utm_source=share&utm_campaign=share_via&utm_content=profile&utm_medium=ios_app

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, Chris and E sit down with Mark Lumpkin from STR Cribs, the company behind 500+ STR setups, to break down the real reasons properties fail and what the best operators do differently.

If you’re buying, designing, furnishing, or managing STRs — this is a masterclass in thinking like a pro instead of an amateur.

Inside this episode:

• The biggest mistakes investors make when buying or furnishing STRs

• Why “more amenities” isn’t the answer — strategic amenities are

• How to work with (and filter out) bad owners

• The 80/20 rule for projects, clients, and portfolio performance

• Why elite STR teams operate like “SEAL Team 6”

• How culture, tension, and standards lead to scale

• The future of STR Cribs and Mark’s next business moves

Guest Bio:

Mark Lumpkin helps investors set up highly profitable STRs all over the country.

00:00 – How STR Cribs Started & Grew to 500+ Setups

00:04:45 – Why High-Net-Worth Investors Still Make Rookie Mistakes

00:09:10 – The Amenities Strategy That Actually Drives Bookings

00:13:55 – Institutional Investors vs Mom-and-Pop Operators

00:18:25 – The Problem With Owners Who Want to “Test It First”

00:22:40 – The 80/20 Rule, Pumpkin Planning & Firing Bad Clients

00:27:05 – Sniper vs Machine Gun: How to Focus Your Time as an Operator

00:31:30 – The STR Cribs Hiring Philosophy: SEAL Team 6

00:36:15 – Creating a High-Performance Culture Through Healthy Tension

00:41:50 – What’s Next for STR Cribs & Mark’s Personal Vision

Guest Link:

https://www.linkedin.com/in/mark-lumpkin-84b173142/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, Bernie Cesareo reveals the mindset and identity shifts that transformed his life, his confidence, and his STR businesses — from shrinking portfolios to scaling multiple companies with clarity and purpose.

This episode breaks down the real reason most hosts stay stuck, how to think and act like a CEO, and the inner work required to grow a business that matches the life you want.

Inside this episode:

• The identity upgrade that changed Bernie’s life

• How self-image controls your STR results

• Why talking about your vision attracts the right people

• The shift from operator → leader → CEO

• How Bernie built multiple businesses by delegating

• Why gratitude, belief, and clarity fuel massive growth

00:01:12 – Bernie’s Big Mindset Shift: Stop Doing Everything Yourself

00:04:07 – “Assume the Wish Fulfilled”: Rewriting Your Identity

00:08:10 – Manifesting the Dream Jeep: Breaking 30 Years of Beliefs

00:11:20 – Running Multiple STR Businesses Through Identity Upgrades

00:14:36 – Lifestyle Freedom: Why Bernie Never Misses His Son’s Games

00:17:00 – The Elder-Care Village Vision: Thinking Bigger Than STR

00:20:12 – From Player to Coach to CEO: Letting Go of Control

00:24:18 – Correcting Systems, Not People: Real Leadership

00:28:55 – How Speaking Your Vision Attracts the Right Opportunities

00:33:42 – Gratitude, Belief, and the Identity That Builds Your Future

Guest Bio:

Bernie Cesareo and his wife Courtney started the company by turning a long-term rental in their hometown into a short-term rental and doing everything themselves from guest support to cleaning and maintenance. Happily surprised with the success and popularity of this property, they decided to turn this side hustle into a primary business. They loved providing quality accommodations and creating great value for their guests and felt they could do this on a larger scale. They started growing the business by becoming co-hosts for other property owners and have added team members to help make everything run smoothly. After several years, they have a team of 8 that manages anywhere from 20-40 properties.

Guest Link:

https://eaglestays.com/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

With Sonder filing bankruptcy and operators across the country getting crushed by fixed leases, the truth is clear: the STR model you choose determines whether you scale… or sink.

In this episode, we break down why arbitrage is failing, what Sonder’s collapse teaches every host, and why co-hosting remains the most profitable, low-risk, scalable model in 2025 and beyond.

Inside this episode:

 • Why arbitrage collapses under pressure

 • The hidden costs operators never calculate

 • Why co-hosting produces higher margins with lower risk

 • How boutique operators beat centralized “big brand” models

 • What the fastest-growing hosts are doing differently

 • The shift every STR operator must make in 2025

Message me to get a free resource and see how the program could fit your goals.

Click the link below:

https://go.strsecrets.com/podcast?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T034&utm_content=RESOURCE

00:01:00 – The Real Cost of Arbitrage: Leases, Debt & Cash Burn

00:02:30 – Why Arbitrage Margins Collapse in Today’s Market

00:03:45 – Co-Hosting vs. Arbitrage: The Risk Difference

00:05:10 – Arbitrage at Scale Becomes a Cash-Flow Death Trap

00:06:15 – Real Examples of Small Operators Losing Money

00:07:10 – The Tiny Margin of Error That Kills Arbitrage Deals

00:08:30 – Why Co-Hosting Wins: Low CAC, High Lifetime Value

00:10:20 – How Operators Are Scaling Co-Hosting With $0 Spend

00:12:20 – Centralized vs. Local: Why Guest Experience Matters

00:15:00 – Why Arbitrage Can’t Keep Up With Industry Changes

00:17:00 – The Bankruptcy Wave: Small Operators Getting Hit

00:18:30 – How to Pivot Out of Arbitrage Before It’s Too Late

00:20:10 – What a Healthy Co-Hosting/PM Business Looks Like

00:22:00 – No Get-Rich-Quick: The Reality of STR Success

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

Whether you're starting with 5 doors or aiming for 500, Brooke breaks down the playbook that actually works.

Inside this episode:

• Why most PMs never break past 50–100 properties

• The REAL reason owner acquisition is so difficult

• Brooke’s formula for predictable PM growth

• Why marketing is now non-negotiable for property managers

• What the top PMs are doing differently

• How the industry is shifting — and where the opportunity is

00:02:11 – Brooke’s Story: How He Scaled to 500 Properties

00:06:34 – Why Most Property Managers Plateau at 50–100 Doors

00:09:58 – Owner Acquisition: The Hardest Part of PM Growth

00:13:22 – Why Homeowners Don’t Convert (And What They Really Want)

00:17:45 – The Data Behind Fast-Growing PM Companies

00:21:18 – Why Marketing Is No Longer Optional for PMs

00:25:40 – Building a Real Sales Pipeline for Property Management

00:30:12 – Brooke’s Predictable Growth Formula Explained

00:34:49 – Industry Shifts: Consolidation, Competition, and Opportunity

00:38:27 – The Future of PM Growth (And How to Win the Next Wave)

Guest Bio:

Brooke Pfautz is one of the industry's foremost experts in growing vacation rental inventory. He literally wrote the book on inventory growth – and it’s already a three-category Amazon bestseller. Brooke got his start in the industry in 2007 when he co-founded Vantage Resort Realty in Ocean City, MD, and took an idea on a napkin to more than 500 properties in just five years. After a successful exit, he went on to grow inventory for other major vacation rental brands as a Chief Business Development Officer in multiple destinations. Most recently, as an executive at a leading vacation rental software company, he saw first-hand through MasterMind groups that he launched and facilitated what worked and what didn’t for the 20 largest and most successful companies in the country. Today, Brooke leads Vintory, the first and only CRM & Sales and Marketing Automation Platform designed exclusively for Vacation Rental Managers to grow their inventory. At Vintory, a team of over 50 growth experts is laser-focused on one thing: helping VRMs hit or exceed their inventory growth goals.

Guest Link:

https://www.instagram.com/vintoryhq/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, we break down the difference between operators who burn out… and operators who build real companies that survive, scale, and eventually sell for life-changing money.

We also cover the hard lessons from companies that grew too fast, collapsed, or went bankrupt—and how to avoid their mistakes.

In this episode you’ll learn:

• Why your STR business already has real enterprise value

• What happens if everything lives in your head (and how to fix it)

• The operational mistakes that bankrupted a fast-growing STR company

• How to build systems that survive without you

• What buyers REALLY look for in an STR business

• The path to a 7–8 figure STR exit

If you want help building an STR business that actually runs without you — and is worth something one day — click the link below:

https://go.strsecrets.com/podcast?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T033&utm_content=STRS

00:01:41 - Sonder going bankrupt

00:03:15 - talking about exits / long hold / vision

00:05:09 - private equity, Blackstone, KKR, etc.

00:06:47 - Vacasa, hyper-local focus, selling to PE

00:08:47 - SOP playbook, fear of death, what happens if you’re gone

00:10:20 - CEO role, brand, numbers, game plan

00:12:00 - not as easy as it looks, 70% with PMs 20+ units

00:13:19 - PE criteria, churn, “can somebody else run my business?”

00:14:55 - Built to Sell, books, contracts, “you not being the system”

Get FREE Access to our Community and Weekly Trainings:

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Recorded LIVE inside the brand-new Freedom Factory, Mike, E., Chris, and Reilly break down the mindset, seasons, strategy, and direction that will define the next 5 years of short-term rentals… and your future in it.

• The story behind building the Freedom Factory

• Mike’s “origin moment” and how it shaped everything

• The dark seasons every entrepreneur must push through

• Why property management will create more millionaires than arbitrage

• The new PM roll-up and what it means for exits

• How STR Secrets is evolving with 3 new shows & deeper curriculum

00:01:41 – The Freedom Factory: How This All Started

00:04:52 – Mike’s Full Circle Moment at the Old Staples Desk

00:08:35 – The “Dark Seasons” of Entrepreneurship

00:12:48 – The Four Phases of Growth Every Operator Goes Through

00:16:55 – Chris’s Story: Going Broke to Buying His First STR

00:20:33 – Riley’s Risk: Payroll on a Credit Card & Buying His First Property

00:24:40 – The Identity Shift Needed to Enter Your Next Season

00:28:53 – Why Property Management Will Create More Millionaires

00:32:41 – The PM Roll-Up & Hotel Fund Vision

00:37:58 – The New Era of STR Secrets: Three Shows + Bigger Vision

Get FREE Access to our Community and Weekly Trainings:

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In this episode, we walk through how top operators are using AI and automation to scale smarter, simplify operations, and outpace the competition.

• How AI is transforming pricing, operations, and marketing

• The biggest mistake hosts make when “trying” automation

• Tools that save hours per week without losing the human touch

• Why your business model must evolve in 2025

• The new advantage: data-driven decision-making

Get the full AI Automation Playbook at strsecrets.com/ai

00:00:18 – Why AI Is the Next Big Shift in STR

00:02:12 – What Hosts Get Wrong About Automation

00:05:09 – The Tools Replacing Busywork in STR Operations

00:08:47 – How AI Enhances the Guest Experience

00:11:38 – Dynamic Pricing and Predictive Data in Action

00:15:22 – Building Systems That Learn While You Scale

00:19:10 – How to Combine AI With a Human Team

00:23:38 – Avoiding the “Set It and Forget It” Trap

00:27:41 – The STR Playbook for 2025 and Beyond

00:30:52 – Final Take: Use AI Before It Uses You

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, we break down how to stop making decisions from lack, step into an identity-led mindset, and actually create the conditions for growth.

• Desire vs. paradigm: the two voices in your head

• How to make decisions from faith, not fear

• The identity → behavior → reality chain

• Why discipline is just choosing desire repeatedly

• What to do when growth feels uncomfortable

• How your environment can hold you back

00:00:00 – Desire vs Fear: The Two Lenses

00:00:12 – Paradigm = Fear and Lack

00:01:44 – Choosing to Live From Desire

00:03:08 – The Identity → Behavior → Reality Flow

00:05:06 – Why Your Current Behavior Matches Your Identity

00:06:49 – Discipline = Making Desire-Based Decisions

00:08:05 – Asking: “Is This from Desire or Fear?”

00:10:12 – Growth Requires Discomfort

00:13:24 – Fear Speaks Louder Than Desire (At First)

00:16:22 – Growth Is Continuous If You Keep Choosing It

Get FREE Access to our Community and Weekly Trainings:

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This episode breaks down exactly when to hire, who to hire first, how to onboard them, and how to keep them executing so you can grow your STR business instead of babysitting it.

• When it’s actually time to hire (not too early, not too late)

• Who your first hire should be in an STR business

• Sample VA schedule for guest communications

• How to onboard using SOPs instead of winging it

• What to pay and where to find VAs

• The weekly meeting rhythm that keeps them accountable

Want to Grab the Hiring and Onboarding Templates?

Just click the link below and DM us "VA".

Link: https://ig.me/m/mike.sjogren?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T031&utm_content=VA

00:00:04 – When to Hire Your First Person

00:00:29 – Signs You’re Doing a 40–60 Hour Week

00:03:52 – Operator First or Sales First?

00:10:07 – Sample STR VA Schedule (Guest Comms)

00:10:24 – What to Pay and What They Do

00:17:42 – Onboarding With SOPs, Not Vibes

00:17:52 – Weekly Meetings and Task Lists

00:18:56 – Growing Their Responsibilities Over Time

00:28:03 – Where to Find VAs

00:28:43 – Use Our Hiring & Onboarding Templates

Get FREE Access to our Community and Weekly Trainings:

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This episode breaks down how most hosts trap themselves in operations — and how to build systems that finally let you step out and scale up.

• Why “hustle” kills long-term growth

• The systems that keep your business running without you

• How to delegate without losing control

• Why buying back your time is your real ROI

• A blueprint to turn chaos into clarity

If you’re tired of putting out fires and want your STR to finally run smoothly,

go to strsecrets.com/ops

00:00:12 – Why Every STR Needs an Operating System

00:04:28 – Automating Guest and Team Communication

00:08:17 – Tracking Operations Like a Real Business

00:11:45 – How to Build Repeatable Systems That Scale

00:15:33 – Managing 100+ Units Without Losing Control

00:19:58 – Training Teams to Operate Like Owners

00:24:40 – Optimizing Listings for Efficiency and ROI

00:29:25 – The Data Metrics Every Operator Should Track

00:33:54 – Using Tech and SOPs to Eliminate Chaos

00:38:42 – The Future of STR Businesses Runs on Systems

Guest Bio:

Michael Dinwiddie is a real estate investor, Airbnb Superhost, and leader in hospitality operation who combines short-term rental management experience with a background in product marketing and customer experience design. As the founder of Togethere Vacation Rentals, Michael manages premium short-term rentals and boutique hotels across Washington State, helping owners increase profitability while creating meaningful guest experiences.

He also built Hospitality HQ, an operating system and training platform that equips hosts and managers with the tools, automations, and processes needed to scale efficiently. Michael’s work bridges the gap between hospitality and technology—bringing professional systems to help scale the next generation of short-term rental entrepreneurs.

Guest Link:

instagram.com/michael.dinwiddie/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

From the new pricing structure to changes in visibility and payout logic, this episode breaks down what’s changed — and how hosts can respond before profits vanish.

We cover:

• Airbnb’s latest Q4 update and what it really means

• Why “Buy Now, Pay Later” hurts your revenue

• The 18% gap between guest and host payout

• How the algorithm update affects your bookings

• The steps to protect your listing performance right now

Want to track and protect your profits after the new Airbnb updates?

Just click the link below and DM us "AIRBNB" to get the exact spreadsheet Reilly shared.

https://ig.me/m/mike.sjogren?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T030&utm_content=AIRBNB

00:01:14 – The “Buy Now, Pay Later” Effect on Host Payouts

00:02:08 – Hidden Revenue Gaps in Airbnb’s Host Fee Changes

00:04:42 – What the Data Says About Visibility and Bookings

00:06:10 – How to Read and Use the Airbnb Spreadsheet

00:08:55 – Revenue Management Tips for the New Update

00:11:24 – Why Some Homeowners Will Lose More Than Others

00:14:58 – Understanding PM Revenue and Homeowner Splits

00:15:24 – Airbnb Host-Only Fee Changes Explained

00:16:01 – Channel Fee Split: How Airbnb Is Changing Payments

00:17:42 – The Real Fix: Adjusting Pricing to Protect Profit

00:19:33 – Why Transparency and Strategy Now Matter More Than Ever

00:21:14 – Recap: The Future of STR Hosting After These Updates

Get FREE Access to our Community and Weekly Trainings:

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From hidden pricing shifts to the new “Buy Now, Pay Later” feature — this episode breaks down what’s happening behind the scenes and how it impacts your bottom line.

• Airbnb’s latest update — and what it really means for hosts

• The 18% pricing gap no one saw coming

• Why “Buy Now, Pay Later” could destroy your cash flow

• How to protect your listings from revenue loss

• The survival strategy hosts need for 2025

00:02:15 – The Buy Now, Pay Later Trap

00:04:50 – Why Airbnb’s Update Is Dangerous for Hosts

00:06:30 – How Guest Cancellations Can Bankrupt Your Month

00:10:22 – The Real Impact of Airbnb’s Policy Changes

00:14:18 – Protecting Your Listings With Better Pricing Strategy

00:18:45 – Revenue Management: How to Fight Back

00:23:10 – Why Market Compression Is Crippling Small Hosts

00:27:40 – The STR Survival Plan for 2025

Get FREE Access to our Community and Weekly Trainings:

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Fabio Moro reveals the brutal truths of running short-term rentals in Italy, and what it really takes to survive in a shifting STR landscape.

• Why most foreign investors get crushed in Italy

• The systems you must have to manage remotely

• What happens when the STR gold rush slows down

• How to protect your properties from market shifts

• Lessons from building a sustainable business, not a gamble

00:01:11 – How Fabio Started Investing in Italy From Abroad

00:03:45 – Finding and Trusting the Right Local Partners

00:06:20 – Turning Old Properties Into Luxury Short-Term Rentals

00:09:42 – Why Italy Is a Hidden Gem for STR Investing

00:12:55 – The Real Costs of Renovating in a Foreign Market

00:16:28 – Remote Management Systems That Actually Work

00:20:12 – Designing Guest Experiences That Command Higher Rates

00:23:40 – Due Diligence and Financial Discipline in STR Investing

00:28:10 – Scaling With Intent: Quality Over Quantity

00:32:02 – The End Goal: Freedom, Culture, and Sustainable Growth

Guest Bio:

Formerly a Partner at a major commodity trading firm with ventures spanning the US and Asia, Fabio now channels his international experience into developing distinctive villas and hospitality projects in Italy, guided by a vision of understated luxury, design and local authenticity

Guest Link:

casaroverella.it

palazzosanvito.it

Get FREE Access to our Community and Weekly Trainings:

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In this episode, he reveals how leadership, culture, and vision turned TechVestor into one of the most respected brands in STR investing.

• How leadership shapes the future of the STR industry

• Building a culture that scales with integrity and precision

• Setting new standards for quality and operations

• Why great teams outperform any market cycle

• The mindset shift every STR leader needs to make

00:03:22 – The Real Problem: Bad Operators Drag the Industry Down

00:07:40 – Leadership and Vision: Believing Before Anyone Else Does

00:11:56 – Building High-Trust Teams That Scale

00:15:38 – Culture Over Everything: The Real Competitive Advantage

00:20:25 – Systems That Outlast the Founder

00:25:44 – The Truth About Scaling: Leadership vs. Management

00:30:57 – How TechVestor Blends Tech and Real Estate to Win

00:35:46 – The Future of STR Leadership and Industry Standards

00:40:38 – Legacy Leadership: Culture, Vision, and Setting the Bar Higher

Guest Bio:

Sief Khafagi is an ex-techie turned real estate investor who has helped thousands diversify into real estate. Today, he’s the founder of Techvestor, one of the first institutional-grade and backed STR portfolios. With their vertically integrated advantages across acquisitions, renovation, design, management, and more, Techvestor is the leader in short-term rentals as an asset class. Backed by in-house technology, one of the deepest talent benches in the industry, and most recently, institutional backing, they're on a path to 500+ owned STRs over the coming years.

Guest Link:

https://www.linkedin.com/in/siefkhafagi/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this breakdown, we show you exactly how to rebuild your listing from the ground up to rank higher, convert faster, and stand out in a crowded market.

• The step-by-step to create a perfect, profit-ready listing

• The mistakes 90% of hosts make in titles and descriptions

• How to fix your visuals and brand in minutes

• What data says about click-through and conversions

• The system top hosts use to stay booked year-round

Want to make your Listing Perfect? Grab the FREE Guide.

Click the link below and DM us "OPTIMIZE"

https://ig.me/m/mike.sjogren?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T029&utm_content=OPTIMIZE

00:00:56 – Creating the Perfect Listing: What Goes Into It

00:03:39 – The Listing Description Framework (Step-by-Step)

00:05:34 – Lifestyle Photos That Drive Bookings

00:09:16 – Photo Strategy: Location, Amenities, Experience

00:13:24 – Use Captions to Boost Click-Through Rate

00:14:24 – The Big Description Mistake: Paragraphs vs Bullets

00:21:44 – Are You Actually Optimized? The Search-to-Listing Check

00:24:03 – KPIs to Optimize Your Listing (Property Refresh Cadence)

00:25:30 – Test Photos for Higher Conversions & CTR

00:26:57 – Build Your Direct-Booking Brand (After You Dominate Airbnb)

Get FREE Access to our Community and Weekly Trainings:

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In this episode, Thibault shares actionable strategies that hosts can use to protect margins, win more bookings, and scale smarter.

• Why Airbnb’s new fee model has hosts freaking out

• How to price for what guests see (not what you keep)

• Tools like PriceLabs—and why they’re useless without context

• How European vs. U.S. guests think about fees differently

• When to simplify pricing and present “one clean price”

• The principles of occupancy, demand, and market alignment

00:05:12 – 3 Pricing Foundations Every Host Must Know

00:07:02 – Why Hosts Are Freaking Out About Airbnb Fees

00:08:22 – The Real Reason Airbnb Changed Its Fees

00:09:15 – The Only Price That Matters to Guests

00:10:24 – Why “One Clean Price” Converts Better

00:11:50 – Airbnb vs. Vrbo vs. Booking.com Costs Compared

00:12:09 – How Airbnb Went From Host-Friendly to Guest-First

00:24:50 – Are More Bookings Always Better?

00:25:04 – AI + Pricing Strategy: Where the Future Is Headed

00:25:22 – Who Owns Mistakes—You or the Machine?

Guest Bio:

Thibault Masson is the Head of Product Marketing at PriceLabs. His short-term rental journey started as a villa owner in Bali and St. Barts, which gave him firsthand insight into the opportunities and challenges of hosting. That passion for hospitality later brought him to Booking.com, where he worked on vacation rental strategy at a global scale, and inspired him to launch Rental Scale-Up as a platform for industry knowledge-sharing. Today at PriceLabs, Thibault brings together his experience as a host, tech marketer, and industry advocate to help property managers worldwide grow through smarter pricing and revenue management.

Guest Link:

https://www.linkedin.com/in/thibaultmasson

Get FREE Access to our Community and Weekly Trainings:

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• How to pitch revenue expectations with confidence

• The $10K guarantee that beat out competitors

• Proposal + deal analyzer templates revealed

• How to handle homeowners on the phone

• Closing tactics to avoid being ghosted

• The 13-day timeline broken down step by step

Want the ACTUAL Step by Step Training? Just click the link below.

https://go.strsecrets.com/watch-strs-vacasa?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T028&utm_content=StepByStep2

In this episode, Matt shares his hard-earned lessons on revenue management, scaling, and the mindset shifts that set top operators apart.

• The truth about revenue management: when to DIY vs. hire

• How beginners can scale from 1–2 units to many

• Success traits Matt has seen across hundreds of operators

• Why your calendar is the foundation of business success

• The mindset shift: “If you can’t help yourself, you can’t help others”

• How to design life first, then build STR around it

00:02 – DIY Revenue Management: Matt’s 3 Best Tips

14:11 – Success Traits vs. Failure Traits

15:29 – The Power of a Strong WHY

18:29 – Calendar & Life Buckets for STR Success

19:08 – If You Can’t Help Yourself, You Can’t Help Others

20:52 – Designing Life First, Then Business

Guest Bio:

Matthew McDonald is a short-term rentals and hotels investor and coach.

Guest Link:

matt.mcdonald@strsecrets.com

Get FREE Access to our Community and Weekly Trainings:

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In this episode, finance expert Ben Coons breaks down the numbers behind gross vs. net commission models—and what you must do to protect your margins.

• Gross vs. net commission explained in plain English

• How Airbnb’s fee hits managers vs. homeowners

• Why this change is different from Vrbo and Booking.com

• Pricing adjustments to avoid eating the new fee

• Commission stacking and where your money really goes

• How to communicate fee changes to homeowners clearly

• Key takeaways to stay profitable under the new system

Co-hosts and homeowners: want the real numbers on Airbnb’s 15% fee?

Click the link and DM us “SPREADSHEET” and we’ll send you the file.

Link: https://ig.me/m/mike.sjogren?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T027&utm_content=Spreadsheet

00:04:30 – Example Scenarios: Who Really Pays the Fee

00:07:00 – Comparing Airbnb, Vrbo, and Booking.com

00:11:30 – Impact on Gross Model Operators

00:14:00 – Impact on Net Model Operators

00:18:30 – The Homeowner’s Point of View

00:23:30 – Commission Stacking: The Hidden Cost

00:26:00 – Pricing Adjustments to Stay Profitable

00:29:00 – How to Communicate Fee Changes to Homeowners

00:32:00 – Key Takeaways: Run the Numbers & Adapt Early

Get FREE Access to our Community and Weekly Trainings:

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In this episode, Chris shares practical frameworks and timeless principles that every business owner (and STR host) can use to stand out, attract clients, and scale smarter.

• Why marketing and sales matter more than ever

• The real difference between content and community

• How to build a personal brand the right way

• Authentic content vs. performative posting

• Head vs. heart: the two frames of content

• Why information ≠ transformation in business

• How to message to your avatar’s pain + desire

• Funnels, ads, and what they can’t replace

• Systems for managing leads without overwhelm

• Why investing in belief shifts your identity

00:01:27 – Why Listen to Chris (Marketing & Sales Depth)

00:03:07 – Community Leverage > Content Alone

00:11:38 – “Give Me a Framework” Moment

00:12:02 – Starting a Brand the Right Way

00:15:05 – Content Resistance, Authenticity, and Output

00:16:48 – Frames of Content: Head vs. Heart

00:21:26 – Information ≠ Transformation

00:26:33 – Avatar, Pain + Desire (Messaging 101)

00:28:15 – Ads, Funnels, and Social Avoidance

00:34:45 – Investing in Belief and Identity Shift

Get FREE Access to our Community and Weekly Trainings:

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In this episode, we break down the cohosting model step by step—from the basics to the systems that let you scale sustainably.

• What cohosting really is (and how it works)

• The 3 key things you need before starting

• How to choose the right market for success

• Proven ways to find clients and grow your portfolio

• The cohost funnel: your roadmap from startup to scale-up

Want the tested and proven Pitch Deck? Just click the link below and DM us "Pitchdeck"

https://ig.me/m/mike.sjogren?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T026&utm_content=Pitchdeck

00:04:45 – What Is Cohosting

00:11:49 – Cohosting vs. Arbitrage

00:12:59 – Why Arbitrage Is Failing

00:15:45 – Why Cohosting Is a Better Model

00:17:26 – Three Key Things Before Starting

00:23:40 – Market Selection for STR

00:26:52 – Acquisition Channels for Clients

00:28:15 – The Cohost Funnel Framework

00:29:40 – Tracking Where You Are in the Funnel

00:34:10 – Special Giveaway for Listeners

Get FREE Access to our Community and Weekly Trainings:

http://group.strsecrets.com/

In this episode, Emanuele and Mike break down how STR can fuel bigger goals, lasting freedom, and a life by design.

• Why STR is a tool, not the destination

• The mindset shift that changes how you build

• How to keep your bigger vision in focus

• Avoiding the trap of chasing unit count

• Using business to buy back your time and freedom

00:03:21 – Designing a Business That Lasts

00:05:26 – Keeping Your Bigger Vision Alive

00:06:32 – The Mindset Shift for STR Success

00:11:00 – The Mindset Shift for STR Success

00:12:15 – Why Belief Fuels Momentum

00:15:27 – Designing a Business That Lasts

00:17:11 – Designing a Business That Lasts

00:19:35 – How to Build Lasting Momentum

00:20:25 – Designing a Business That Lasts

00:20:56 – Scaling With the Right Mindset

Get FREE Access to our Community and Weekly Trainings:

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In this episode, he joins Emanuele to break down the science behind choosing the right markets and making STR numbers work for you.

• How John analyzed 100+ STR markets with zero failures

• The method he uses to “decipher the numbers”

• Why market selection is the real make-or-break skill

• Common mistakes hosts make when running numbers

• How to use data to build a sustainable STR portfolio

00:04:20 – Using Data to Drive STR Success

00:07:23 – Using Data to Drive STR Success

00:08:38 – How to Analyze STR Markets Effectively

00:09:33 – Using Data to Drive STR Success

00:10:45 – How to Analyze STR Markets Effectively

00:19:15 – Learning From Costly STR Mistakes

00:19:53 – Spotting Profitable STR Deals

00:21:15 – How to Analyze STR Markets Effectively

00:22:57 – How to Analyze STR Markets Effectively

00:25:27 – Using Data to Drive STR Success

Guest Bio:

John Bianchi is the Founder of STR Search. He has successfully directed over $100M+ investments into cash-flowing Airbnbs across the country. As a master of deciphering complex datasets, John has a 100% success rate across 250 + properties for helping his clients acquire cash-flowing Airbnbs. When he's not poring over data, he’s spending quality time with his family.

Guest Link:

https://www.instagram.com/theairbnbdataguy/

Get FREE Access to our Community and Weekly Trainings:

http://group.strsecrets.com/

This episode dives into how that moment reshaped his approach to business—and why building systems that outlast you is the true measure of success.

• The turning point when Steve realized he couldn’t keep grinding

• Why time freedom matters more than unit count

• How to design an STR business that runs without you

• Systems vs. hustle: the real key to longevity

• Lessons every host should apply before burnout hits

00:06:06 – Why Time Freedom Beats Unit Count

00:08:03 – The Health Crisis That Sparked Change

00:11:22 – Reframing Success Around Freedom

00:14:48 – Designing a Business That Runs Without You

00:16:52 – Shifting From Hustle to Sustainability

00:20:08 – Systems That Keep Growing Without You

00:26:32 – Avoiding the Burnout Trap

00:29:10 – Lessons From Scaling the Wrong Way

00:33:49 – Time Freedom as the Real Metric

00:34:20 – Building an STR Business That Lasts

Guest Bio:

Steve Resnick left the corporate world to pursue a career in co-hosting. He scaled from 12 to 99 properties in less than 2 years.

Guest Link:

https://linktr.ee/heavenlyrez

Get FREE Access to our Community and Weekly Trainings:

http://group.strsecrets.com/

This episode dives deep into mindset, grit, and the obstacles that stop most people before they ever scale.

• The difference between interest and commitment

• Why obstacles are often just excuses in disguise

• Lessons from Navy SEALs on resilience

• How to reframe challenges into momentum

• What separates consistent winners from quitters

👉 Do you really want it? Prove it—click the link below and start building your STR business today.

https://go.strsecrets.com/podcast?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T025&utm_content=Wantit

00:00:02 – Deciding If You Really Want It

00:01:29 – The First Mindset Shift Toward Success

00:02:24 – Breaking Through Excuses and Rationalizations

00:03:26 – Why Most People Quit Too Early

00:04:50 – Building Grit When Challenges Stack Up

00:06:01 – Turning Pain Into Long-Term Discipline

00:07:15 – Lessons on Focus From Elite Performers

00:08:29 – How to Push Past Mental Barriers

00:09:39 – Recommitting When Doubt Creeps In

00:10:58 – Keys to Sustainable Personal and Business Growth

Get FREE Access to our Community and Weekly Trainings:

http://group.strsecrets.com/

But the ones that work? They’re powered by more than numbers.

In this episode, we break down both sides of the equation: finding deals that actually perform and delivering hospitality that scales profit.

• 10-point hospitality playbook

• Why 95% of STR deals never make sense on paper

• The creative edge investors need to make deals work

• Why service ≠ hospitality (and why guests feel the difference)

• How to balance ROI with guest delight and repeat bookings

00:03:56 – Service vs. Hospitality

00:06:11 – Setting Higher Financial Targets

00:08:09 – Guest Experience at Every Stay

00:15:12 – Building a Hospitality-Driven Team

00:16:23 – Guest-Centric Business Model

00:17:17 – Scaling Means Scaling Leadership

00:20:27 – The Roots of Modern Hospitality

00:22:52 – Designing Emotional Guest Checkpoints

Get FREE Access to our Community and Weekly Trainings:

http://group.strsecrets.com/

In this episode, they share the systems, deals, and mindset that made it possible.

• How they pivoted from co-living to STRs

• The growth path from a handful of units to 80

• Systems they rely on to keep operations tight

• The partnerships that accelerated their scale

• Lessons learned about market selection and timing

00:04:31 - Learning from a high-functioning real estate company

00:05:52 - Landing a management gig through direct outreach

00:08:04 - Managing a growing number of people

00:10:15 - Staying focused while running STR operations

00:14:42 - Biggest drags on a short-term rental business

00:16:05 - What each founder values most in the business

00:18:59 - Identifying problems and fixing them

00:20:48 - Preventing issues from stacking up

00:23:39 - Taking responsibility for team mistakes

00:26:57 - Boutique hotel as a pivotal business asset

00:28:39 - Balancing investment strategy with STR management

00:34:36 - Staying at your own properties to evaluate quality

00:37:18 - Challenges get easier with experience

Guest Bio:

Blake Anthony Carter and Jeremy Courtney have both been operating in real estate and property management for over a decade. They initially got started in the co-living space, which led them to short-term rentals. They eventually sold our co-living business and with all-in on short-term rentals. Blake and Jeremy started a Facebook group and a meet-up group that allowed them to become known as the go-to guys for STRs in Austin. Their company is called Cribs. Blake and Jeremy now own a boutique hotel and three SF doors. They manage over 80 listings and have a real estate sales/consultant team.

Guest Link:

https://www.instagram.com/blake.anthony.carter

https://www.instagram.com/thejeremycourtney

Get FREE Access to our Community and Weekly Trainings:

http://group.strsecrets.com/

In this episode, we dive into what it takes to scale, the operational demands behind success, and how to grow without sacrificing your life.

• How the top U.S. property manager was built since 2021

 • The workload reality behind rapid STR growth

 • Why work-life balance is elusive in property management

 • How to keep guest satisfaction high while scaling

 • Lessons on building a sustainable management model

Want to get crystal clear on your goals and scale your STR business?

Click the link below to book a discovery call and see if our Mastermind is the right fit for you.

Link: https://go.strsecrets.com/podcast?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T024&utm_content=Goal

00:00:43 - Guest Introduction: Jamie Lane on the Report

00:04:58 - Operational Quality: Maintaining Cleaning at Scale

00:05:53 - Local PM Groups vs. National Lists

00:08:26 - Threshold: ~20 Listings Per Market To Appear

00:10:28 - Work Ethic Analogy (Kobe at 3:00am)

00:12:56 - Hiring/Team/Tech Stack

00:15:28 - Value Score Signal vs. Outcome

00:16:37 - Seasonality or Demand Shifts

00:19:48 - Methodology: Econometric Models to Isolate Drivers

00:22:04 - Pricing Tactics to Drive Occupancy

00:24:40 - Market Share / Portfolio Size

00:25:12 - Policy Analysis: Cleaning Fees Across Managers

Get FREE Access to our Community and Weekly Trainings:

http://group.strsecrets.com/

In this episode, we break down the systems, hiring moves, and mindset shifts that free you from the day-to-day grind—so you can grow faster.

• Why you always need that next big goal

• The real reason we become entrepreneurs: time control

• How to qualify and hire your first key player

• Setting up turnover checklists that run without you

• The role that keeps properties guest-ready every day

• Why you must have someone who can step in for you

• The investment that buys back your time

• How to stop micromanaging and reacting to fires

00:04:03 - Why you always need that next big goal

00:04:01 - The real reason we become entrepreneurs: time control

00:10:35 - How to qualify and hire your first key player

00:09:25 - Setting up turnover checklists that run without you

00:01:06 - The role that keeps properties guest-ready every day

00:13:57 - Why you must have someone who can step in for you

00:00:01 - The investment that buys back your time

00:19:51 - How to stop micromanaging and reacting to fires

Get FREE Access to our Community and Weekly Trainings:

http://group.strsecrets.com/

From attracting 30 members to the mastermind to tactical takeaways from a 2000+ person event, we break it all down.

• Why raw content works better than polished

• The one onboarding question that reveals true goals

• STR WealthCon recap: biggest takeaways

• How to get ROI from live events

• The vibe shift in the STR community

-

Want to get crystal clear on your goals and scale your STR business?

Click the link below to book a discovery call and see if our Mastermind is the right fit for you.

Link: https://go.strsecrets.com/podcast?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T023&utm_content=Clear

-

00:03:01 - Raw Content That Converts

00:05:55 - Massive Takeaways From WealthCon

00:08:42 - Unlock Event ROI Secrets

00:11:32- Mindset Shift Every Host Needs

00:14:25 - Behind the Scenes of a Power Launch

00:16:54- High-Impact Networking Tips

00:19:32- Underrated Gold From Live Events

00:22:21 - Mastering the Referral Flywheel

00:25:06- Growth Hacks for Ambitious Hosts

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

But they’re not designed for how people actually *live.*

In this episode, guest architect Zeke Freeman shares the hidden design flaws baked into most houses — and how his process reshapes spaces around *real human behavior.*

Whether you’re remodeling a home, designing an Airbnb, or dreaming about your next property, this episode will flip how you think about space, function, and flow.

What you’ll learn:

- Why most homes don’t reflect how people actually use them

- How to design with *invisible behavior patterns* in mind

- The “door test” for practical flow in short-term rentals

- Why your home may be sending the wrong emotional signals

- Zeke’s process for uncovering how a space wants to work — before you build

00:01:15 - Designing Identity: From Architecture to Personal Branding

00:04:32 - Why Architects Make Great Entrepreneurs

00:07:58 - Thinking in Systems: A Superpower for Founders

00:10:40 - Applying Space Planning to Business Structure

00:14:06 - Designing Offers Like Floor Plans

00:17:21 - Why Constraints Fuel Creativity

00:21:44 - How Messaging Is Like Structural Engineering

00:26:02 - From Drafting Buildings to Drafting Funnels

00:30:55 - The Hidden Layer of Brand Architecture

00:35:19 - Why Most Founders Skip the Blueprint Phase

00:40:46 - Using Architectural Thinking to Scale Operations

00:45:10 - Form Follows Function in Business Too

Guest Bio:

Zeke Freeman is a visionary architect, builder, and passionate advocate for the transformative power of design. With over two decades dedicated to shaping the realms of hospitality and Colorado's modern design, Zeke has emerged as a leader in boutique hotels, hospitality development, and strategic business management. As the CEO of TheRootTeam, which includes an international team of Architects, an estate brokerage, and a Hospitality Development Company, Zeke Freeman has not only left an indelible mark in Colorado Architecture but has also steered the company towards its 12th year of success, bringing many beautiful projects and many more impacted lives together across the Front Range. Zeke is also the host of the RADicalhospitality show, which explores the intersection of Architecture, Development, and Hospitality.

Guest Link:

https://linktr.ee/zfreeman1

Get FREE Access to our Community and Weekly Trainings:

http://group.strsecrets.com/

In this episode, Adam breaks down the 5 core sales frameworks he teaches to high-performance closers in STR and beyond.

From reframing rejection to diagnosing like a doctor, this is the mindset, structure, and clarity that separates amateurs from closers.

What You’ll Learn:

• The “doctor frame” for every sales call
• Why connection > charisma
• The mindset shift every new closer must make
• Why your pitch must pass the “grunt test”
• How sales becomes your ultimate life skill

Guest Bio:

With over $100 million in sales to his name, Adam Stein brings a rare mix of high-performance sales strategy and human-centered communication to the mic. Having taken more than 4,000 sales calls and reviewed over 10,000, he's coached and led sales teams from startup scrappers to 9-figure juggernauts. An avid golfer and father of two awesome boys, Adam blends psychology, mindset, and real-world sales mastery to help entrepreneurs sell with confidence, clarity, alignment, and compassion.

00:04:31 - Learning from a high-level sales mentor changed everything

00:08:54 - Overcoming mindset blocks was the first real sales battle

00:13:04 - Sales is philosophy — not just tactics

00:17:26 - Old-school sales techniques don’t work in STR anymore

00:21:58 - Great salespeople are obsessed with discovery

00:26:12 - Your pitch must pass the “grunt test”

00:30:35 - If you don’t believe in what you’re offering, they’ll feel it

00:34:48 - Diagnosing like a doctor earns trust and conversions

00:39:10 - Sales is service when done with integrity and empathy

Guest Link:

https://www.instagram.com/the.salesscientist/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

This episode breaks down exactly why $150K–$200K is now the minimum to win, and how to outpace the competition by investing in what actually matters.

You’ll learn:

• How Mike’s team turned a $715K property into a 26%+ cash-on-cash winner

• Why outdated listings are getting crushed in today’s market

• The new furnishing rule of thumb (hint: it’s not $6K per room anymore)

• Why “I’ll add amenities later” is the biggest red flag from investors

• Real-world examples of design ROI and creative deal structuring

• How to dominate Year 2 with direct bookings, not just Airbnb

If you’re serious about STR, this episode will shift how you think about budget, value, and building long-term cash flow.

-

Want bookings before you're even done renovating?

Just click the link below to get the Free Training.

https://go.strsecrets.com/podcast?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T022&utm_content=PreLaunch

-

00:03:30 – Budget Furniture and Low Investment No Longer Work in B or C Markets

00:05:00 – Reinvesting in Amenities Can Revive Underperforming Properties

00:07:15 – Pre-Launching With Mood Boards Can Generate Bookings Before Renovation Ends

00:09:03 – Investing More in Amenities Can Double or Triple Cash-on-Cash Returns

00:13:02 – You Need Direct Bookings—Don’t Rely Only on Airbnb and VRBO

00:15:01 – You’re Competing on ADR Only If You’ve Maxed Out the Amenity Strategy

00:23:29 – Borrow Amenities From Other Markets to Win in Your Own

00:25:16 – Don’t Wait to Upgrade—Do It Upfront or You’ll Lose Money

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, Patrick breaks down his roll-up strategy for short-term rental management businesses, focusing on Joshua Tree.

You’ll learn:

• How to value STR property management companies

• The hidden formula top performers are using (4.9+ reviews + max RevPAR)

• How he’s creating additional revenue from Netflix, OF shoots, and more

• The underrated power of real hospitality, hyper-local service, and partner alignment

This isn’t just about scaling, it’s about building a legacy business in a saturated market.

00:00:11 - Become the Local Expert, Not a Nationwide Manager

00:08:45 - Three Business Lessons from Open Water Swimming

00:09:03 - Use a Roll-Up Strategy to Scale Management Companies

00:10:00 - Study High-Performing PMs for 4.9+ Ratings at Scale

00:11:20 - How to Value and Buy STR Management Companies

00:13:32 - Use Off-Market Outreach to Acquire Small Managers

00:17:00 - Full-Service PM is the Only Way to Compete in Joshua Tree

00:21:22 - Add Production Shoots to Maximize Weekday Revenue

00:25:45 - How to Get Featured by Netflix and PR Agencies

00:35:00 - Partnerships are Marriages—Choose and Lead with Trust

Guest Bio:

Patryk Swietek is a 28-year-old entrepreneur with a background in building tech companies since the age of 14. Ever since getting into real estate at 24 years old, he's been a thought leader in the STR industry, teaching the co-hosting model with his own Amazon best seller book and online podcast. He scaled from 5 of his own properties to managing over 100 signed properties in Joshua Tree in under 1 year. He has bought 3 STR co-hosting companies to become the #1 co-host in one of the most competitive vacation rental markets in the country. His company and homes have been featured on Netflix, Wall Street Journal, NY Times, Dwell, etc.

Guest Link:

https://www.instagram.com/patryk_swietek

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, we break down exactly how the short-term rental tax loophole works, how you can use it to eliminate 5–6 figures of taxable income, and what rules you must follow to stay IRS-compliant.

Whether you own 1 property or manage dozens, this is one of the most powerful tools in your financial playbook.

You’ll Learn:

• Why this loophole can save you $40K+ per property

• The 2 conditions to qualify for non-passive treatment

• How cost segregation studies supercharge your deductions

• Why co-hosts & PMs can charge consulting fees using this

• What to avoid if you don’t want the IRS to audit you

Want to directly talk about taxes and how you can make use of the tax loophole for STRs? Just click the link below:

https://go.strsecrets.com/podcast?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T021&utm_content=Taxes

00:05:08 – Powerful Tax Strategy to Slash Your Income

00:06:01 – How One Property Saved Me $92,000 in Taxes

00:09:02 – Must-Know Criteria to Unlock STR Tax Benefits

00:09:11 – Track This or Risk Losing Your Tax Deductions

00:10:16 – Use It Wrong, Lose It All

00:12:03 – Avoid This Common Mistake with Friends and Family

00:13:04 – How to Legally Save $40,000 with Depreciation

00:16:06 – Transform OK Deals Into Great Ones

00:17:17 – A Brilliant Offer Property Managers Should Use

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

In this episode:

• Jeff’s journey from VRBO and Expedia to Furnished Finder

• Why monthly rentals are the most underserved niche in real estate

• How to price your MTR listings for max profit

• The 3 types of hosts who thrive on Furnished Finder

• Tech upgrades, new guest demographics, and the future of midterms

• Why most Airbnb hosts still don’t understand real returns

Whether you’re a casual host or a pro operator, this episode will help you rethink your strategy, lower your fees, and build a more resilient rental business.

Guest Bio:

Jeff Hurst is the President and CEO of Furnished Finder, a role he assumed in November 2023 at the invitation of the company’s founders. Prior to that, Hurst was the Chief Operating Officer of Expedia Brands and Co-Lead of Expedia Group Marketing. Before that, he was the President of Vrbo and Chief Strategy Officer of HomeAway, where he oversaw the company’s successful sale to Expedia, Inc. Before venturing into the vacation rental industry, Hurst worked as a consultant at McKinsey & Company, collaborating with consumer brands on corporate strategy, mergers and acquisitions, and pricing strategies. Hurst received his MBA from the Stanford Graduate School of Business and BA from the University of Texas at Austin.

00:05:00 - Game-Changing Insights: Luxury Brands in Vacation Rentals

00:10:00 - Unstoppable Leaders: CEOs Who Shaped My Philosophy

00:15:00 - Winning Balance: How I Prioritize Family, CEO Role, & Life

00:20:00 - Bold Moves: Why I Chose Furnish Finder Over Other CEO Jobs

00:25:00 - Secret Advantage: Choosing the Right City & Team First

00:30:00 - Proven Blueprint: Advice to My Son on Career & Leadership

00:35:00 - Power Tip: Best Way to Reconnect with Furnish Finder

00:40:00 - Ultimate Secret: #1 Tip for Short Term Rental Success

00:45:00 - Smart Hack: How Hosts Save Money by Reverse-Engineering Airbnb

Guest Link:

https://www.linkedin.com/in/jeff-hurst-atx

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

In this episode, we break down exactly what changed and what to do about it.

Here’s what you’ll learn:

• Why Airbnb is auto-switching hosts to a “Firm” policy, without clear consent

• What happened to the original Strict policy (spoiler: it’s weaker now)

• The difference between “Strict,” “Firm,” and the new “Limited” cancellation options

• Real refund scenarios, who gets paid when guests cancel

• Why Mike is switching to “Limited” on all new listings

• How to check if your policy was changed (and how to fix it)

Don’t let Airbnb rewrite your house rules without you knowing.

Want to get the latest Airbnb Policy One-Pager?

Just click the link below and DM the word "Policy".

Link: https://ig.me/m/mike.sjogren?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T020&utm_content=Policy

00:00 - Airbnb Cancellation Policy Changes & How To Adapt

01:24 - Choosing the Right Cancellation Policy: Strict vs Firm vs Limited

02:49 - How To Use Rank Breeze To Track Your Airbnb Rankings

04:14 - Opting Out of Airbnb’s Forced Policy Changes

05:39 - How New Listings Are Affected By Airbnb’s Updated Rules

07:04 - Strategies for Competing in Saturated STR Markets

08:29 - Building Repeat Clients & Getting Direct Bookings

09:54 - Protecting Against Chargebacks With Rental Agreements

11:19 - Know Your Market’s Booking Window & Adjust Policies

12:44 - Using Tools Like AirDNA & Rank Breeze To Optimize Revenue

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

In this episode, you’ll learn:

• Why most first-time hosts shouldn’t expect a profit (and what to aim for instead)

• The $65K reno gamble that paid off, plus how to pitch owners to invest

• 5 non-negotiables every STR investor needs to check before buying

• How to match properties to real investor goals (not hype)

• What to say when a listing has bad photos, ugly furniture, and zero bookings

• How to turn stale listings into discounted wins using seller credits

• The mindset shift that helped turn their lowest income year into their highest ever

Whether you’re starting from scratch or trying to turn things around, this episode is packed with honest advice and real numbers to help you grow the right way.

Don’t go it alone, learn from people who’ve already done it.

00:01:14 - Revenue Boost: Previous Owner’s $30K Shows Untapped Potential

00:05:05 - Hustle Story: From Mowing Lawns to Building Wealth

00:09:37 - Mindset Shift: Realizing It Was Never Just a Job

00:13:00 - Profit Jump: Small Changes, Big Revenue Growth to $70K

00:16:54 - Unique Selling Point: Win Without a Pool

00:19:31 - Client Filter: Say ‘No’ More Often to Grow Stronger

00:20:42 - Investor Clarity: Aligning with Each Investor’s True Goal

00:22:45 - Negotiation Win: Securing $130K in Seller Credits

00:26:29 - Host Reality: Why Airbnb Won’t Help When It Matters

Guest Bio:

Joe Rohne bought my first two short-term rentals in 2022, one with his wife and one with a business partner. Within three months, he shifted into cohosting and picked up 2 cabins in Branson. Joe went to the STR Wealth Conference and met a bunch of people. From there, he started his own cohost mastermind to have weekly calls and help each other grow. He grew to 12 mostly luxury cohost properties. Joe sold his first two STRs in 2024 and upgraded to a larger luxury property, and is looking to buy another this year. All this turned into him having a co-host podcast and helping others get into this space. He has been a realtor for 5+ years in St. Louis, and got his license in Florida to sell in Panama City Beach, which is where the majority of his STR business is. In August 2024, Joe got linked with Tyler and the Savvy team, and he is now building a team that services the entire panhandle. He currently has ten co-hosts and one owned property.

Guest Link:

facebook.com/joe.rohne

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

Just 18 months later?

He runs 37 listings, left his W-2, and built a profitable, freedom-filled business, all without using his own capital.

In this episode, we break down exactly how he did it:

• The red flags in his arbitrage model that forced a pivot
• How he turned losses into leverage with a co-hosting pitch
• A case study that took one property from $90K → $211K
• The “Underserved Investor Method” for finding hidden gems
• Why volume doesn’t matter, precision does
• And the system he used to scale without capital or burnout

If you’re stuck, tired, or scaling blindly, this might be the episode that saves your business.

00:00 - Burned Out at 11 Units, Freedom at 37: The Mark Story

00:01 - Rising Rents and Saturation: Why Arbitrage Fails

00:04 - Audit and Pivot: How a Simple Portfolio Audit Changes Everything

00:05 - Switch to Co-Hosting: Scale with No Capital

00:06 - The Design ROI Pitch: Turn $10K Into $33K Fast

00:09 - Underserved Investor Method: Find Hidden Gems Others Miss

00:12 - $30K Redesign → $211K Revenue: Real Numbers, Real Proof

00:13 - Fire Bad Managers: Care Wins Big

00:14 - Small but Mighty: Profit Without Massive Volume

00:15 - Cohosting Margins: 50%+ With Full Teams

00:16 - Don’t Blame Pricing: Fix Your Offer and Model Instead

00:17 - Raise the Bar: Better Hosts, Better Homes, Better Industry

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

In this episode, she shares how that crushing moment forced her to pivot into midterm rentals, automate with AI, and rebuild a better business that runs with less stress, higher profits, and total platform independence.

What You’ll Learn:

• Why Airbnb banned her (and what you can do to prevent it)
• How midterm rentals (MTR) gave her 90–95% occupancy
• The AI tool she built to automate listings, guest comms & content
• How she balances business with nervous system regulation & wellness
• Her playbook for turning burnout into purpose-driven success

Tools & strategies for STR → MTR pivots, burnout recovery, and branding with integrity.

00:35 - Never Build Your Whole Business on Someone Else’s Platform

06:03 - Building a Strong Real Estate Brand Identity

07:01 - How to Be Known in Your Network to Grow Your Business

13:00 - Choosing the Right Community to Plant Roots for Business & Life

16:17 - Growing from STR to MTR: Changing Ownership Structures

17:33 - Airbnb Kicked Me Off: The Risk of Platform Dependence

19:20 - Switching from Short-Term to Mid-Term Rentals: Why & How

25:00 - Why Midterm Rentals Mean Better Clients & Less Work

26:12 - Using AI and Custom GPTs for Marketing and Operations

30:51 - Becoming a Relocation Specialist: Multiple Income Streams

33:02 - Smart Branding: Pick a Consistent Name & Handle

34:28 - Niche Marketing: Speaking Directly to Your Avatar

39:46 - Sharing Authentic Life Stories to Build Audience Trust

43:53 - First Aid Kit for Burnt Out Hosts: Breathwork, Meditation, Nervous System Health

48:35 - Success Secret: A Never-Quitting Mindset

Guest Bio:

Amanda Williams, widely known as The Traveling Realtor, is a seasoned real estate entrepreneur, eXp Realty agent, and visionary behind Carolina Furnished Rentals (CFR). Founded in 2019, Carolina Furnished Rentals skyrocketed in 2020 as demand for longer stays surged during the pandemic. This pivotal success became a lifeline in 2021 when Amanda was unexpectedly removed from Airbnb through no fault of her own—a common challenge for many hosts relying solely on third-party platforms.

Rather than seeing it as a setback, Amanda turned this challenge into an opportunity to take full control of her business, doubling down on the mid-term rental (MTR) model. She transformed Carolina Furnished Rentals into a thriving enterprise, proving the power of owning your brand and building a business independent of volatile platforms.

Today, Amanda uses her expertise to help Airbnb hosts with 5+ properties transition to the stability and profitability of MTRs. Through her 30-Day MTR Sprint Program, she provides hands-on coaching, automation strategies, and proven systems to help property owners scale smarter, reduce headaches, and create a business they truly own.

Amanda’s mission is simple: empower others to build wealth, freedom, and a brand they’re proud of while navigating the ever-changing rental landscape. From coaching clients to speaking at events, Amanda inspires hosts to take control of their future and achieve financial independence on their own terms.

Guest Link:

https://www.instagram.com/amandathetravelingrealtor/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

...it’s your offer.

In this episode, we walk through how to dominate even when bookings slow down, using frameworks that helped our clients grow from 0 to 100+ properties (without lowering their standards).

Inside, you’ll learn:

• The 2 sales you must make to land AND grow every client
• How to niche down with an offer big managers can’t touch
• Why “boutique” isn’t enough (and what to say instead)
• ChatGPT + Hormozi = your unfair advantage
• The COHOST sales framework that turns owners into clients fast

If you’re tired of feeling stuck in the cohosting middle zone…This is the episode that unlocks your next 10 doors.

Want to generate your Perfect Offer? Just click the link below to get the ChatGPT Prompt:

https://ig.me/m/mike.sjogren?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T018&utm_content=Prompt

00:00 – Stand Out or Stay Stuck: Why Differentiation Is Non-Negotiable

00:12 – The COHOST Framework: A Proven Sales Funnel for STR Growth

00:45 – Survive the Booking Slump: Why Traditional Markets Are Struggling

02:44 – Don’t Panic Price: How to Maximize Occupancy Without Slashing Rates

04:48 – The #1 Mistake: Thinking Being Small Automatically Wins Trust

05:15 – Riches in Niches: Hyper-Focus Your Property Strategy

07:00 – The Plus-One Strategy: Tiny Add-Ons That Win Big Contracts

10:33 – STR Takeover Transformation: Craft an Offer They Can’t Refuse

14:59 – Risk-Reversal Guarantees: The Ultimate Owner Conversion Tactic

21:00 – Make STRs Great Again: Why Boutique Operators Are the Future

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

Not because they don’t want success.

But because they still talk like the person who doesn’t have it yet.

In this solo episode, Mike and E breaks down how internal dialogue shapes your future, and how AI can help you become the version of yourself that already wins.

What you’ll learn:

• How to reprogram your self-talk to unlock growth
• Why “watering down” your vision is killing momentum
• The AI tools Mike uses weekly to review sales calls, write listings, automate ops, and even train his team
• How to use custom GPTs to build an internal consultant that never sleeps

If you’re still running 80% of your business manually…this episode will change that.

03:00 - Audit Your Inner Voice to Align with the Life You Want

07:00 - Step Into Your Vision by Speaking It Out Loud

10:00 - Optimize Sales Calls Using Custom GPT Feedback Loops

12:30 - Write High-Converting Listings and Titles with AI

14:00 - Do Market Research, Regulations, and Pricing with GPT

15:30 - Automate and Personalize Guest Messaging at Scale

17:00 - Generate Social Media and Website Content with ChatGPT

19:00 - Streamline Hiring, SOPs, and Onboarding with AI

22:00 - Analyze Property Performance and Build Offers with GPT

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

In this episode, we break down exactly what’s coming, why this event will never happen again, and how to make the most of it.

What you’ll learn:

• Why this is the last WealthCon hosted by Mike & Bill

• The new format designed for all STR business levels

• Speaker highlights: Cody Sanchez, Pace Morby & more

• The 9 deep-dive masterclasses (creative finance, hotels, scaling)

• Real deals, partners, and freedom stories born from past WealthCons

• VIP & Diamond perks: elite networking, pre-events, premium access

• Mike’s “Generational Wealth Blueprint” sneak peek

Whether you’re coming or just curious, this is the behind-the-scenes breakdown you need.

Learn more about the 2025 STR Wealth Conference

https://na.eventscloud.com/ereg/index.php?eventid=829193&discountcode=MEMBERSONLYCLUB

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

02:58 – Why This Is the Final STR WealthCon

04:50 – Scaling from 15 to 2000+ Attendees in 3 Years

06:45 – Why This Will Be the Most Impactful STR Event Yet

07:17 – Keynote Power: Cody Sanchez, Pace Morby & Business Mastery

12:00 – A Brand-New Generational Wealth Roadmap (Never Shared Before)

15:26 – Networking Blocks: How Deals Worth Millions Begin

17:20 – Raising Industry Standards: How Better Hosts Beat Regulation

20:03 – How to Build a Business That Runs Without You

Buck scaled two.

In this episode, we break down how he went from managing one unseen unit in Nashville to running a 70-property short-term rental operation and a digital marketing agency at the same time.

No fluff, just systems, AI, and strategic growth.

What you’ll learn:

• How he jumped from 5 to 20 units with one key client
• The team structure and cashflow strategy that saved them in winter
• Using AI + Hormozi to craft irresistible offers
• The “$10 / $100 / $1K / $10K” time block system
• Why smart maintenance = higher reviews and retention

If you’re building a real business, this one’s a blueprint.

04:48 – How One STR Outperformed 4X and Sparked a Business

10:55 – Cleaning & Tech Enabled Remote STR Scaling

13:27 – Investor Stepped In During Cash Flow Crisis

15:05 – Zig When Competitors Zag: Break Industry Norms

17:00 – 5-Star Guarantee: No Commission Without Reviews

20:01 – Flat-Fee Maintenance Boosts Property Standards

24:00 – Focus on $1K and $10K Tasks to Scale Faster

Guest Bio:

Buck Cumbo is the owner of www.seamountainvacations.com. He is managing nearly 50 million dollars in assets amongst 60+ properties in the Myrtle Beach area. Buck have also recently been brought on as Brand Director at www.theonehundredcollection.com.

Guest Link:

http://www.instagram.com/captain_buck_

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

It’s called “Services,” and it lets guests book things like chefs, trainers, and masseuses without your approval, while you carry all the liability.

In this episode, I break down:

• Why this new feature is dangerous for pro hosts
• How to opt out in 3 steps
• How to beat Airbnb at its own game by building your own Services page
• Why relying on Airbnb in 2025 is a bigger risk than ever

If you’re serious about building a business (not just listing properties), this is mandatory viewing.

03:04 - The Hidden Risk for Hosts: Guests Can Book Services Without You Knowing

04:45 - Host Liability Risks From Airbnb Services

05:55 - How Bad Service Experiences Can Hurt Host Reviews

07:00 - Why Airbnb Rolled Out Services Without Consulting Hosts

08:15 - The Simple 3-Step Process to Opt Out of Airbnb Services

10:28 - Why Hosts Must Act Now: Collective Opt-Out Pressure Matters

13:00 - How to Add a “Services” Tab to Your Direct Booking Website

16:00 - Partnering With Local Providers Can Lead to Repeat Guest Referrals

19:00 - Will Opting Out of Services Affect Airbnb Search Rankings?

22:00 - Airbnb Is Targeting Hobby Hosts—What It Means for Pros

23:30 - Why You Must Diversify Beyond Airbnb and Build a Real Business

26:05 - STR Secrets Fulfillment Strategy for Different Host Levels

Guest Link:

instagram.com/boostlyuk/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

Diana and Josh, two married architects, were forced to reimagine their future after losing both their fathers in 2021.

What began as a journey to escape the W-2 grind became Terra Palm Springs, the city’s first true wellness boutique hotel.

They reveal how they:

• Pivoted from flips and BRRRRs into commercial real estate

• Used their design and construction edge to underwrite with vision

• Created immersive guest experiences that transcend hospitality

• Built three synergistic businesses to scale with intention

• Took bold action while honoring their deepest personal “why”

This story will move you, inspire you, and give you a real blueprint for building a brand, and a life that matters.

What You’ll Learn:

• How to spot your unfair advantage (and actually use it)

• The key to underwriting without inflating projections

• What makes a boutique hotel truly stand out

• How to transition from short-term rentals to hotel ownership

• Why generosity is the secret weapon in hospitality

00:00 - Action drives clarity

00:35 - Process-proven growth

01:36 - Power couple feature

02:20 - Life-changing loss

05:55 - Strategic shift to scale

07:26 - Expert system builders

09:50 - Value-add obsession

10:56 - Underwrite with confidence

14:30 - Unapologetic branding

16:42 - First-of-its-kind wellness hotel

21:00 - Team-powered execution

25:40 - The real estate awakening

28:00 - Finding purpose through pain

31:30 - Create your unfair advantage

36:00 - Future-built freedom

43:00 - Hospitality secret: give generously

Guest Bio:

Diana and Josh Dobken have 15+ years of experience in the architecture and construction industries. They strategically invest in value-add opportunities where they can use their design expertise to maximize their return on investment. Additionally, Diana and Josh co-host 35+ MTRs and STRs across multiple states for other real estate investors, bringing their hospitality standards and design sensibility to each property we manage.

Beyond property investment, Diana and Josh also manage comprehensive operations teams for hotels, with them overseeing director of operations roles and guest experience management. This hands-on operational experience gives them invaluable insights into how design decisions impact day-to-day functionality and guest satisfaction.

Their most current project involves the Architectural and Interior design of Terra Palm Springs, the first wellness Boutique Hotel in Palm Springs featured in Vogue, Forbes, Hotels Above Par, and selected as part of Travel and Leisure It List of 2025’ 100 Best New Hotels in the World.

Guest Link:

http://www.instagram.com/d.i.fi

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

From custom comps to Airbnb integration, this episode breaks down the new features, how to use them, and what they reveal about the 2025 STR landscape.

What you’ll learn:

• How to use the new Rentalizer confidence score and custom comps
• Why saved projections and expense tracking are game changers
• The truth about 2025 booking trends (and who’s winning)
• What AirDNA’s forecast says about rates, RevPAR, and smart investing

If you’re serious about short-term rentals, you can’t afford to miss this.

Want to get our Latest Deal Analyzer?

Just click the link to our Instagram below and send 'Rentalizer'

https://ig.me/m/mike.sjogren?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T015&utm_content=Rentalizer

02:35 – Why the Update Matters: Major Interface and Logic Changes

05:10 – Data Model Shift: From Historical to Projected Revenue

08:00 – The 3 Core Metrics You MUST Understand in the New Version

11:00 – Updated Filters: Comp Selection and Market Targeting

13:30 – Accuracy Considerations: What AirDNA Gets Wrong (and Right)

16:45 – Real-Time Demo: Using the New Tool to Analyze a Property

20:20 – How to Reverse Engineer a Successful STR Deal with AirDNA

24:00 – Hidden Pitfalls: Common Mistakes People Make Post-Update

28:10 – Strategic Recommendations for Using the New Rentalizer

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

What happened next?

A wild ride through the world of short-term rentals, driven by family, strategy, and a long-term vision few operators ever reach.

In this episode, Fouad breaks down:

• How a personal medical emergency forced him to buy his first Airbnb
• Why most operators price listings wrong—and how he uses math instead
• The real difference between luxury and comfort STRs (and why he runs both)
• His custom tech stack using Go High Level
• And the real reason he’s scaling to $12M/year before exiting

This one’s for the operators who want to scale smart, stay profitable, and build something sellable.

What you’ll learn:

• How to scale with dual verticals (luxury + comfort)
• Why you must reverse-engineer around your exit
• How banking lessons apply directly to STRs
• Why pricing = math, not emotion
• How Fouad thinks about purpose and legacy

Ready to build a business that banks would beg to fund?

Fouad shows you how.

03:30 – Breaking the Golden Handcuffs: Why He Left Corporate

07:00 – First STR Deal: Starting Small With Big Vision

10:00 – Smart Risk: Learning to Bet on Yourself

13:00 – From 1 to 10+ Units: Scaling With Confidence

17:00 – Wealth Mindset: Thinking Like an Owner, Not an Operator

20:00 – Cash Flow vs Time: Redefining Success Metrics

24:00 – Building a Business, Not a Job: Systems and Team Growth

27:00 – Lessons From the Field: What He’d Do Differently

30:00 – Purpose-Driven Investing: Time, Family, and Freedom

Guest Bio:

Fouad Bazzi is a professional in the short-term rental (STR) industry. His activities include owning, managing, and building new build-to-rent properties, as well as consulting and educating others in the STR space. He also owns a pool servicing company that specializes in serving STR properties.

Guest Link:

https://www.instagram.com/fouad_airbnb

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

In this live breakdown, we cover:

• The truth about Airbnb’s new “Services” feature and why it matters

• What this means for photographers, chefs, massage therapists, and YOU

• How Airbnb plans to monetize add-ons (and why you might not see a cut)

• Major liability concerns Airbnb isn’t talking about

• How this could affect your guest experience—and your reviews

• Why this is really a pivot toward becoming the Instagram of Travel

Plus: actionable strategies to get ahead of this change, build local service partnerships, and protect your property.

TLDR? This update means more work for hosts, unless Airbnb starts paying us to help them grow. Watch this now so you’re not caught off guard.

Want to get the summary of Airbnb's Latest Update?

Just click the link to our Instagram below and send 'Update'

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00:00 – Bold Shift: Airbnb’s 2025 Release Redefines the Platform

01:30 – Major Update 1: Cleaning Services Now Offered to Guests

04:00 – Major Update 2: Handy Services and Maintenance on Demand

06:30 – Control at Risk: Services Can Be Scheduled Without Host Approval

08:45 – Host Autonomy Undermined: Who Has Access to Your Property?

10:30 – Guest Experience Prioritized: Host Voice Being Muted

12:00 – Airbnb’s Strategic Shift: From Booking Site to Service Ecosystem

13:30 – Host Action Plan: Communicate, Audit, and Prepare

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

Marcus breaks down:

• Why most entrepreneurs aim too small and why it costs them everything
• The mental and physical toll of building at scale (including 7 years without a dentist visit)
• How he filters “good money” vs “bad money” when raising capital
• The future of short-term rentals in a regulated, AI-powered world
• Practical leadership advice for scaling teams without losing your mission

Plus: his marathon training, travel hacks, and how to avoid becoming a micromanaged founder.

Whether you’re a startup founder, STR operator, or tech junkie—this is a must-listen for anyone who wants to win big without burning out.

Ready to scale? Tap into Marcus’s billion-dollar playbook now.

00:00 – Go Bigger: Why Playing Small Carries the Same Risk but Less Reward

00:39 – Craft Over Hype: The Power of Repetition and Mastery

02:04 – Be There: Why Leading Remotely Doesn’t Win Markets

03:45 – Market Leadership: How Hostaway Beat Older, Bigger Players

05:58 – Hiring Giants: From 50,000 Applicants to the Top 0.1%

08:59 – Cost of Ambition: Health, Relationships, and the Real Price of Building

12:29 – Go for Billionaire Moves: Why Medium Goals Aren’t Worth the Sacrifice

15:31 – Choosing Good Money: Partnering with Investors Who Let You Lead

17:23 – No Kitchen Rules: Keeping Creative Control While Scaling Up

20:27 – Invisible AI: How Hostaway Uses Tech to Deliver Unseen Excellence

23:00 – Review Intelligence: Turning Guest Feedback into Business Strategy

25:30 – Tool Advantage: Hostaway’s Marketplace as a Growth Engine

27:17 – Global Expansion: Owning New Markets One Continent at a Time

29:33 – Regulation Shakeout: Why Strong Rules Are Good for Professionals

32:50 – Reputation Reset: Cleaning Up the Industry with Standards That Matter

Guest Bio:

Marcus Räder is co-founder and CEO of Hostaway, the leading all-in-one vacation rental management software. Originally from Finland, Marcus has lived in many countries around the world including Sweden, Poland, and The Netherlands before settling in Canada. It was this passion for travel, real estate and his dedication to learning about the vacation rental ecosystem that enabled the creation of Hostaway.

The company quickly grew thanks to the deep technological expertise of its founders, with over a decade of tech start-up success between them. Hostaway gives property managers all the tools needed to compete with hotels and other vacation rentals, including sales channel management, dynamic pricing and hospitality services. It now boasts preferred partnerships with Airbnb, Vrbo and Booking.com, in addition to a marketplace of over 100 integrated software partners.

Guest Link:

https://www.linkedin.com/in/marketingmarcus/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

Straight from the STR Boardroom event in Salem, hosts Chris and E break down their biggest takeaways from Dr. Rachel Gainsbrugh’s AI workshop to the emotional breakthroughs in hot seats, to Mark from Minoan’s CEO mindset at 50+ employees.

What you’ll learn:

• The AI stacking method Rachel used to double her sales team’s close rate

• The 5 levels of VA hiring, from cheap help to AI-powered specialists

• Why great team members outgrow companies, and how to lead through it

• The exact moment a founder must pivot from operator to people leader

• How to use the 5 Dysfunctions of a Team framework to build culture that scales

• Why emotional safety is the hidden growth lever most CEOs ignore

• And how to actually implement event takeaways before you lose momentum

This isn’t another tech tips episode.

It’s a tactical and vulnerable deep dive into what it takes to scale, lead, and stay grounded in 2025.

00:00 – Building Confidence: Lessons from Struggle, Sales, and Self-Belief

04:00 – Rewiring Identity: From Overwhelm to Intention

08:00 – Leveraging Chaos: Why Adversity Becomes Your Superpower

12:00 – The Four Levels of Competence: From Unconscious to Mastery

16:00 – Winning in Business: Simplifying Systems, Offers, and Time

20:00 – $20K Days in 5 Hours: Prioritizing High-Leverage Work

24:00 – Clarity Is Power: Why Lack of Decision-Making Kills Momentum

28:00 – Excuse Audit: The Hidden Stories That Keep You Small

32:00 – Emotional Regulation: How to Respond Instead of React

36:00 – Final Challenge: Step Into Power and Choose a New Story

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

…but because they don’t have a system.

In this training, Mike and Chris break down the 3 proven models for hiring virtual assistants.

Agency, recruiter, and self-hire.

Plus the crucial 4R framework you need before bringing anyone on.

Whether you’ve got 5 properties or 100+, this is the training that saves you from wasted money, broken systems, and constant turnover.

What you’ll learn:

• The 3 types of VA hiring models (and when to use each)

• The biggest reason your VA won’t work out (it’s not what you think)

• How to build a talent pipeline that scales with your portfolio

• When to hire for skills vs culture fit

• Bonus: Where to find agency + recruiting referrals we actually trust

_

Want to get the FREE VA Contract and 4R Doc?

Just click the link to our Instagram below and send 'Contract'

https://ig.me/m/mike.sjogren?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T013&utm_content=Contract

00:00 – Hiring Roadmap: Breaking Down the VA Models

02:00 – Agency Model Explained: Training Wheels for Scaling Leaders

05:00 – Recruiting Model: Upfront Investment, Long-Term Efficiency

08:30 – Self-Hiring Secrets: Full Control, High Risk, High Reward

11:00 – Referral Power: Leveraging A-Players to Source Talent

13:30 – Cultural Pitfalls: The Hidden Risk in Team Referrals

16:00 – Specialty Roles: Revenue Management vs. Marketing VAs

19:00 – Creating Execution Frameworks for Social & Brand Marketing

22:00 – Revenue Management Mastery: Metrics, Mindset, and Misconceptions

25:00 – Bonus Resource: Contract Templates & Legal Protections for VA Hiring

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

They’re missing decision.

In this episode, Mike and Emanuele break down the 5 mindset philosophies that transformed their lives...

...from escaping burnout and W2 jobs to building multi-million-dollar businesses and raising families with time freedom.

If you feel like you keep “trying” but never break through, this episode will call you out...

...and pull you forward.

What you’ll learn:

• The most powerful reframe for taking back control of your life
• Why saying “I’ll try” guarantees failure
• How to train your decision-making muscle daily
• The “day one” philosophy that separates top performers from the rest
• A no-fluff breakdown of time vs. money thinking (and how to escape the trap)

Ready to finally commit?

This is your line in the sand.

00:00 - Uncovering Transformational Beliefs that Redefined Success

04:00 - Embracing Radical Ownership: Life Happens *For* You

09:35 - Unlocking Growth Through the Day One Philosophy

14:30 - The 4 Powerful Stages of Skill Development

18:20 - Tactical Time vs Money: Rewriting Productivity Rules

22:00 - Designing a $20K Month in 5 Hours: The Value-Driven Hustle

26:30 - Eliminating Excuses: Breakthrough Decisions that Shape Destiny

31:10 - The Critical Power of Fast Decision-Making

33:00 - Rethinking Reality: Story, Meaning & Inner Peace

35:00 - Final Challenge: Cut the Dirty Yes, Choose Powerfully

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

In this episode, Mike breaks down the 7 most common mistakes that silently ruin guest experiences and the reviews that follow.

These aren’t theories.

They’re field-tested lessons from 1,200+ reviews, across 28 properties, and over 5 years of hosting.

You’ll learn:

• Why nickel-and-diming your guests kills conversion
• The #1 amenity guests expect (but almost no one provides)
• How to stop losing stars from poor messaging and over-automation
• Why Photoshop and misleading listings backfire (fast)
• The deep clean schedule every top host follows
• How to protect margins while leveling up experience
• The review-killer most hosts don’t realize they’re doing

If you’re stuck at 4.8 and can’t crack 4.95+, this is your fix.

05:00 – Algorithm Boost: How Amenities and Photography Drive Ranking

06:00 – Lightning Response: The Profit Power of Immediate Communication

08:00 – Misleading Listings: The Hidden Cost of Photoshop and Fluffed Locations

11:00 – Guest-Friendly Pricing: Stop Nickel-and-Diming for Add-Ons

13:00 – Annual Investment Rule: Keeping Properties Fresh and 5-Star Worthy

15:00 – The Upgrade Clause: Property Improvement Plans That Scale Value

17:00 – The Cleanliness Factor: Deep Cleaning Every Quarter Pays Dividends

19:00 – Messaging Mistakes: Why Over-Communication Kills Guest Experience

21:00 – Final Recap: 7 Things Hosts Do That Secretly Cost Them Reviews

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

AirDNA’s Chief Economist Jamie Lane joins the show to break down what’s actually happening behind the scenes in the short-term rental market...

...and why most hosts are missing the shift.

Inside this episode:

• The real story behind occupancy, rates, and guest demand in 2024
• Why “big box” managers are losing properties fast
• The key numbers top investors are watching (and how to use them)
• How AirDNA’s new tools are reshaping STR deal analysis
• The warning signs for hosts scaling past 50 units and what breaks first
• Why small, well-managed portfolios are quietly outperforming everyone

You’ll also hear how Jamie’s team is using AI and custom comps to bring never-before-seen clarity to STR investing...

...and what you can do to stay ahead.

Listen now to future-proof your portfolio before the data leaves you behind.

03:30 – Supply Shock: Why New STR Listings Are Surging Nationwide

07:00 – Booking Behavior: How Travelers Are Changing Their Habits

10:00 – Revenue Realities: The Decline in ADR and Occupancy Rates

13:30 – Market Saturation: Top Cities Facing Over-Supply Pressures

17:00 – Strategic Advantage: How to Win in Competitive Markets

21:00 – Data-Backed Decisions: Using AirDNA to Stay Ahead

24:00 – The Investor Shift: From Arbitrage to Ownership Models

27:00 – Resilience & Risk: Preparing for Softening Demand Cycles

30:00 – Long-Term Outlook: What Smart Operators Are Doing Next

Guest Bio:

Jamie Lane is Vice President of Research for AirDNA, a short-term rental data & analytics company. He is responsible for data analysis, thought leadership, and leveraging advanced analytical techniques to provide new insights into short-term rental supply, demand, and pricing trends. He has been published in academic and professional journals and regularly speaks at lodging industry forums.

Prior to AirDNA, Jamie spent 10 years as an economist at CBRE, leading research, forecasting and data intelligence teams to support client analysis. Mr. Lane is an active member of the National Association of Business Economists and the Atlanta Economics Club. Jamie holds a B.S. in Economics from the University of Georgia and an M.S. in Business Economics from Georgia State University.

Guest Link:

https://www.linkedin.com/in/jamiehlane

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

Ashley Freeman wasn’t supposed to be here.

Divorced, struggling to make ends meet as a tennis pro.

She took a chance on Airbnb with her farmhouse.

Now she manages over 105 units, leads a team of 25……

and lives a life most people only dream about.

In this powerful episode, Ashley reveals:

• How a side hustle became a 7-figure business
• The mindset shifts that changed everything
• Why systems + a strong team scaled her from 4 to 100+ properties
• How she created a 5-star guest experience that owners can’t stop raving about
• The identity shift required to step into true leadership

Success doesn’t happen overnight.

It happens when you refuse to quit.

Listen now and see how Ashley built an empire…

…one step, one belief, and one property at a time.

03:30 – From Rock Bottom to Rising Entrepreneur: Ashley’s Journey

07:00 – Faith, Grit, and Overcoming Self-Doubt in Business

10:00 – Rebuilding Self-Image: How Belief Rewires Success

13:30 – Tactical Scaling: Systems, Team Building, and Leadership Lessons

17:00 – Secrets to Sustainable Growth: Mindset, Service, and Strategy

20:30 – Life by Design: Building Freedom Through STR Success

24:00 – Living the Dream: Redneck Ranch, Soccer Travels, and Family First

Guest Bio:

Ashley Freeman is a 7-figure short-term rental expert who transformed her life through the power of short-term rentals. Starting with just one property, she scaled her business to 105 properties in under three years, growing from less than $50,000 in her first year to $2 million annually by year three, with the support and mentorship of STR Secrets and Conway Consulting. Passionate about serving others, Ashley is dedicated to helping people find the same freedom and life-changing opportunities that the short-term rental business gave her.

Guest Link:

https://www.instagram.com/velvet_ditch_villas

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

If you collect emails, drop a guidebook link, or offer guests early check-in via Venmo…

You might be in violation of Airbnb’s new policy.

In this episode, Mike Reilly breaks down exactly what Airbnb’s new off-platform & fee transparency rules mean for STR hosts.

And how to stay compliant without losing control of your business.

You’ll learn:

• The exact actions Airbnb will now penalize (even by AI detection)
• Why asking for an email could get you flagged
• How to safely use guidebooks, QR codes, and text marketing
• The only way to charge guests for add-ons (without breaking policy)
• The smart way to collect damage waivers and manage taxes without risk

If 80% of your bookings come from Airbnb, you can’t afford to get this wrong.

02:30 – Dangerous Moves: Why Secret Messaging Will Get You Flagged

05:00 – Booking Extensions & Repeat Guests: What’s Now Off-Limits

07:30 – Is Direct Booking Worth It? Margins vs Platform Protection

10:00 – Hostfully Links, Guidebooks & Legal Loopholes Explained

13:00 – Mandatory Disclosures: HOA Rules, Emails & County Compliance

15:00 – Fee Transparency: Avoiding Suspensions With Clean Listings

18:00 – Payment Violations: Why Airbnb Bans Zelle, Venmo & Side Deals

21:00 – Damage Waivers Over Deposits: How to Protect and Profit

24:00 – Airbnb AI Enforcement: Messaging Triggers and Flagging Risks

27:00 – Contact Info Restrictions: What You Can and Can’t Ask Guests

30:00 – SMS Tactics: Getting Verbal Consent and Staying Compliant

33:00 – Future-Proofing: Will Airbnb Eliminate Direct Contact?

36:00 – Review Removal Struggles: Why AI Appeals Are Failing Hosts

39:00 – Case Study: Retaliatory Reviews & the Fight for Fairness

42:00 – Platform Fatigue: Why Community Knowledge is Your Best Weapon

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

Ron Curtis didn’t quit his job.

He just built a business so efficient that he didn’t have to.

In this episode, Ron breaks down how he:

• Turned a $3,700 house hack into a 50-property portfolio
• Cleared over $10K in credit card debt and now manages $300K in available credit
• Uses his 9–5 income to fuel real estate moves without burnout
• Built systems, VAs, and SOPs to scale without stress
• Teaches financial literacy by living it, not just posting about it

You’ll also learn:

• Why relationships > money in cohosting
• The mindset shift that tripled his capacity
• And how he helped one client buy a $1M building, just from Airbnb cash flow

This episode is proof you don’t need to quit to win.

04:30 – Market Momentum: Flips, Deal Flow, and Fear-Based Opportunity

09:00 – Financial Literacy First: Foundational Principles for Entrepreneurs

13:30 – Zero to Fifty Listings: Scaling with Systems and Strategic Partnerships

18:00 – Designing Teams for Freedom: SOPs, VAs, and the Org Chart Blueprint

22:30 – The Mindset Shift: Working On the Business, Not In It

27:00 – Simplify to Scale: Letting Go of the Noise and Focusing on ROI

31:30 – Buying Back Time: Vertical Integration and Efficiency Hacks

36:00 – Real Client Wins: How STR Cashflow Changed Lives and Bought Freedom

41:00 – House Hacking & Books That Sparked a Million-Dollar Portfolio

Guest Bio:

Ron Curtis is a native Washingtonian and the founder of a short-term and mid-term rental management business based in the Washington, DC area. Ron's journey into short-term rentals started with house hacking—he leveraged first-time homebuyer programs to purchase his first home, a turnkey $423,000 property, for just $3,700 out of pocket. He converted his basement into a studio efficiency and listed it on Airbnb. As Ron traveled, he realized his basement was consistently booked and covering his mortgage. That’s when he fell in love with the concept of Paycations—earning passive income while exploring the world. He built an automated, scalable business model that allows him to manage rentals from anywhere with just WiFi and a reliable cleaning team. Over the last 3.5 years, he has organically grown from managing one property to 50—all while working a full-time 9–5 government job in DC. Ron loves to share his insights on scaling a short-term rental business, automation strategies, and how others can achieve financial freedom through short-term rentals.

Guest Link:

www.instagram.com/wavy_stay

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

Everyone’s complaining about deals not working.

But here’s the truth...

...it’s not the market; it’s your property.

In this episode, we break down:

• Why most STRs fail to hit pro forma in today’s market
• How one $700K Pinehurst property generated $45K in bookings in 5 weeks
• What amenities are actually driving bookings in top markets
• How to design listings that feel different (and rank higher)
• Simple ROI math for cold plunges, saunas, and garage conversions

You’ll also learn how Airbnb is shifting toward experiential stays.

And how to make sure your listing stands out in a sea of sameness.

Don’t wait for the perfect deal. Create it...with the right design and data.

04:00 – Targeting Travel Avatars: Niche Down to Maximize Bookings

06:00 – Real Case Study: How a $700K Property Secured a Celebrity Booking

08:00 – Pre-Launch Tactics That Drove $12K in Bookings Without Photos

10:00 – Benchmarking & Amenity Differentiation in Saturated Markets

12:00 – ROI on Amenities: Saunas, Cold Plunges & Game Rooms

14:00 – Pinehurst Playbook: Amenity Investments That Drive ADR Growth

16:00 – Tailoring Amenities to Market: Golfers, Families & Regional Travel Types

18:00 – Algorithm Hacks & Listing Design That Trigger Emotion and Visibility

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

Emanuele Pani went from mopping floors and fixing leaks…to owning nearly every unit in his building.

But success wasn’t what he expected.

In this episode, you’ll hear:

• How he bought 39 out of 40 units using seller financing & hustle
• What happened when COVID hit, no grace period, no backup plan
• The creative deals that made it all possible (and profitable)
• Why burnout and identity loss followed after the win
• How he rebuilt his purpose with long-term hospitality and legacy in mind

This isn’t a how-to. It’s a how-he-did-it.

From broke to burned out and back to intentional growth.

04:30 – From Cleaning Units to Closing Deals: The Hustle Years Begin

09:00 – Bold First Move: Buying 12 Apartments with No Credit

13:30 – Managing Chaos: Mortgages, Maintenance, and Mentality

18:00 – Refinancing & Reinvesting: How One Refi Fueled the Next Level

22:30 – Rising Too Fast: Distractions, Syndications, and Burnout

27:00 – The Redemption Plan: 18-Unit Acquisition Through Sheer Will

31:30 – Pandemic Pivot: Surviving COVID with Mid-Term Mastery

36:00 – The Final Two: Closing the Hardest Sales with Strategic Leverage

41:00 – Full Circle Wealth: STR Structure, Community, and Long-Term Vision

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

In this episode, Tyler Coon and Mike Reilly dive into what’s really happening across the short-term rental market in 2024...

...and where the smart money is moving.

You’ll learn:

• Why low-end properties are disappearing (and what replaces them)
• How investors are multiplying profits through equity exits
• What upgrades are actually producing 50%+ cash-on-cash returns
• The biggest mistake STR hosts make with property design and amenities
• Why boutique cohosts and local managers are beating big-box operators

The STR industry is consolidating, and only the best will survive.

05:30 – Luxury Dominance: The Future of Short-Term Rentals

08:30 – STR Consolidation: Why Only the Top 10% Will Thrive

11:00 – Strategic Renovation: High ROI From Over-Investing in Design

13:30 – Sleeping 30: Big Groups, Bigger Opportunity

16:00 – Building a Moat: Unique Amenities That Lock In Demand

18:30 – Recession-Proof Strategy: Why Luxury Still Wins in Downturns

20:30 – Equity Moves: Sell or Reinvest for Maximum Return

23:30 – Portfolio Power: Scaling with High-Performing Assets

Get FREE Access to our Community and Weekly Trainings:

group.strsecrets.com

It’s not your strategy.

It’s not your effort.

It’s your identity.

In this episode, mindset coach Adam reveals how shifting his subconscious beliefs helped him triple his income in just 8 months……without changing his work ethic.

You’ll learn:

• Why you attract what you feel, not what you say you want

• How to rewire limiting beliefs using emotional repetition

• Why most goals fail without identity alignment

• The daily 30-minute practice that transforms your vibration

• Why real estate, business, or coaching success starts in the mind

Hard work isn’t enough.

Change your inner world

……and watch your outer world follow.

04:00 – Breaking Point: Transformational Moments that Spark Change

08:00 – Identity Shift: Reprogramming Your Self-Image for Success

12:00 – Unshakable Ownership: Facing Hard Truths to Reclaim Power

16:00 – Debunking Limiting Beliefs: Where They Come From & How to Break Free

20:00 – Emotionalization Mastery: Embodying Beliefs That Attract Results

24:00 – Regulate to Rewire: The Role of Nervous System in Manifestation

28:00 – Vibrational Alignment: How Feelings Shape Reality

32:00 – Real-World Manifestation: From Vision to Deal in 3 Days

36:00 – Integration & Flow: Anchoring the Inner Work into Real-Life Wins

Guest Bio:

Adam Avenus is a mindset and manifestation coach who has spent the last 8 years learning about neuroscience, quantum physics, spirituality and the psychology behind the production of extraordinary results. He found this work first through meeting a coach while he was selling Real Estate, and she helped him triple his income in 8 months. After experiencing what he thought was ‘success’ selling real estate, he started building a company in the software space, came and worked at STR Secrets, and built a small management company, all before going all in on his coaching business. When Adam first found his work, he made $4,000/month and was depressed. Now, he has made over $100,000 last month and have never felt more free or peace in his life. 

Webinar Link:

https://go.avenusconsulting.com/quantumleapmasterclass

Get FREE Access to our Community and Weekly Trainings:

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In this episode, Mike reveals how he sold a 4-unit for $530K and turned one cash-flowing asset into two.

Increasing his annual income by $20K and doubling his return on equity to 42%.

You’ll learn how to:

• Know when it’s smarter to sell or refinance

• Use a simple formula to spot dead money in your portfolio

• Turn today’s high interest rates into tomorrow’s buying advantage

• Upgrade your investor pitch if you’re a property manager or cohost

This is not theory.

This is how smart investors build wealth when others freeze.

Don’t let rising rates or inflated prices scare you.

Use math, not emotion.

03:15 - Interest Rates & Market Dynamics: What’s Really Driving Real Estate Trends

06:38 - Capitalizing on a Potential Market Rebound

08:56 - The Power of Strategic Home Design and Amenities

12:10 - Creative Investing: How to Make High-Priced Homes Pencil Out

15:42 - Personal Property Case Study: Real Numbers, Real Lessons

19:05 - Debt-to-Income Mastery: Unlock Your True Buying Power

24:00 - Cash-Out Refinance: A Wealth-Building Strategy Explained

28:17 - The True Cost of Holding Equity with Low Returns

31:30 - Sell vs. Refinance: Which Path Builds More Wealth?

36:05 - 1031 Exchanges & Strategic Redeployment of Equity

38:40 - Enhancing Returns with Furnishing, Tech & Experience Design

41:25 - Real Estate as an Experiential Platform: Be First in Your Market

44:00 - Simple Math vs. Complex Emotions: Making Rational Investment Decisions

46:45 - Coaching Investors: Ask the Right Questions to Guide Strategy

49:00 - Build Your 5-Year Vision: Align Your Real Estate with Life Goals

Get FREE Access to our Community and Weekly Trainings:

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Jodie Odlin’s first short-term rental was a total mess.

Guest issues, mistakes, zero systems.

Most people would’ve quit.

She didn’t.

Now she runs a growing, profitable STR business with multiple listings and a rock-solid operation.

In this episode, Jodie reveals:

• What went wrong with her first property...and how she fixed it

• The mindset shift that helped her push through the pain

• Systems she uses to scale without burnout

• How she handled bad reviews, tough guests, and surprise expenses.

• Strategies to maximize revenue & run lean operations

If you’re in the struggle phase, this is the roadmap out.

02:15 - Experience Over Property: Why Guests Choose You

07:40 - Set Expectations: Preparing Guests for a Perfect Stay

12:55 - Beyond Checkout: Creating a Lasting Guest Impression

17:30 - Guest-First Mindset: The Key to Hospitality Success

22:10 - Pushing the Limits: Redefining Short-Term Rental Excellence

Guest Bio:

Jodie Odlin is the founder of Hospitable Hosts, a globally recognized movement dedicated to elevating hospitality standards in the short-term rental (STR) and vacation rental industry. This initiative was born when hosts from around the world came together in a collaborative, multi-authored book, sharing their insights, experiences, and passion for creating exceptional guest experiences. Through Hospitable Hosts, Jodie has built a community-driven platform that champions excellence, education, and innovation in the STR space. Her work empowers hosts, property managers, and industry professionals to adopt best practices, embrace responsible hosting, and enhance guest satisfaction—ensuring that STR businesses thrive while upholding the highest hospitality standards. With a deep-rooted commitment to bridging the gap between traditional hospitality and modern vacation rental experiences, Jodie continues to inspire and educate hosts worldwide. Her leadership within Hospitable Hosts has sparked a global conversation about ethical, guest-centric hosting, creating a ripple effect of positive change across the industry. Jodie Odlin’s mission remains clear: to shape a more hospitable world, one stay at a time.

Guest Link:

http://www.instagram.com/hospitablehosts

Get FREE Access to our Community and Weekly Trainings:

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Most hosts wait too long to list their property.

Losing the prime booking window and leaving thousands on the table.

In this episode, we break down:

• How one STR booked $18,000 before the remodel was done
• Why booking windows matter—and how to win them
• The Pre-Stay Checklist that guarantees 5-star reviews
• How economic downturns = once-in-a-decade STR opportunities
• Why boutique STR operators are set to dominate as big players collapse

Bear markets don’t break businesses…they build millionaires.

Now is the time to pre-launch, optimize, and invest smart.

00:00 - Understanding Market Volatility in STR Investing

02:30 - Economic Trends Impacting Short-Term Rentals

05:15 - How Interest Rates Shape STR Profitability

08:40 - Inflation, Tariffs, and Their Effect on Real Estate

12:10 - Strategic Investing During Economic Uncertainty

16:30 - Recession-Proofing Your STR Business

20:00 - Leveraging Financial Cycles for Wealth Creation

24:15 - Building a Sustainable STR Portfolio in Any Market

28:45 - How Government Policies Affect STR Hosts

33:20 - Future-Proofing Your Real Estate Investments

38:10 - The Power of Data-Driven Decision Making

42:30 - Final Advice: Staying Ahead in an Unpredictable Market

Get FREE Access to our Community and Weekly Trainings:

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Jeremy Werden never planned on becoming a short-term rental investor.

After losing his private equity job due to COVID, he had no choice.

His first move?

Boat rentals inspired by the Ozark TV show.

His real breakthrough?

Accidentally discovering cohosting and STR investing.

Now, he runs a 7-figure STR business.

Owns multiple properties, and built BNB Calc, the must-have deal analysis tool for Airbnb investors.

In this episode, Jeremy reveals:

●︎ How he scaled from boat rentals to Airbnb empire

●︎ The 3 business levels that take you from $10K to $100K/month

●︎ How to grow a cohosting business WITHOUT owning property

●︎ Why automation & hiring a team are the keys to STR success

●︎ How he convinced banks to fund his first STR deals (even with no credit history)

04:20 - Mastering Market Trends: Staying Ahead in STR Investments

09:33 - Scaling Smart: Creative Funding and Bank Strategies

10:18 - BNB Calc: The Revolutionary Tool for Investors

14:50 - From Solo Hustle to Scalable Business: Growth Stages

15:21 - Winning Clients: The Art of Persuasive Pitching

19:13 - Optimizing Operations: Streamlining Management for Profit

23:46 - Exceeding Expectations: Raising the Bar in STR Hospitality

25:38 - Process Over People: Fixing Systems for Success

31:53 - Leveraging Media: The Power of Podcasts for STR Growth

35:01 - Property Selection Secrets: Finding the Right Fit

38:13 - Untapped Markets: Atlantic Beach Investment Potential

Guest Bio:

Jeremy Werden is the co-founder of BNBCalc, host of the short-term rental pros podcast, and 7-figure short-term rental co-host and investor.

Guest Link:

https://www.instagram.com/jeremywerden

Get FREE Access to our Community and Weekly Trainings:

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Most Airbnb hosts wait until it’s too late to fix problems.

Leading to bad reviews, lost revenue, and angry guests.

What if you could eliminate guest complaints BEFORE they happen?

In this episode, we break down:

●︎ The EXACT Pre-Stay Checklist that guarantees 5-star reviews

●︎ Why most hosts don’t inspect their properties—and why that’s killing their ratings

●︎ How to create a guest experience that WOWs from check-in to checkout

●︎ The secret to spotting & fixing issues before your guests arrive

●︎ Why small details = more repeat bookings and higher profits

Want to run a STR business that guests rave about?

This checklist is non-negotiable.

02:30 - Using AirDNA to Accurately Analyze STR Deals

05:15 - Avoiding Pricing Mistakes That Kill Your Margins

07:50 - The Power of Pre-Launching Listings for Maximum Bookings

10:00 - The Strategy That Landed a $9,600 Booking Before Going Live

12:15 - Why Professional Photos Aren’t Always Necessary at Launch

14:30 - The Key to Standing Out in a Highly Competitive STR Market

16:45 - Solving the 90-Day Restriction Problem on New Listings

18:20 - The Power of Mood Boards to Secure Bookings Without Final Designs

20:00 - Building a STR Brand That Instantly Attracts Guests

22:30 - Creating an Unforgettable First Impression for Your Guests

25:45 - Implementing a Rock-Solid Pre-Stay Inspection Process

28:15 - The Game-Changing Checklist for Flawless STR Operations

30:10 - Why Pre-Staying at Your Own Property is the Ultimate Quality Control

33:00 - Final Advice: How to Set Your STR Business Up for Long-Term Success

Get FREE Access to our Community and Weekly Trainings:

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Most people think high interest rates and a slow market mean it’s a bad time to invest in short-term rentals.

But what if that’s exactly why now is the BEST time to buy?

In this episode, Avery Carl breaks down:

●︎ Why 2023-2024 is tougher than 2008 for real estate—but still full of opportunity

●︎ How experienced investors are closing deals while everyone else hesitates

●︎ The biggest mistake new investors make when looking at STR properties

●︎ Why overpriced listings sit for months...and how to negotiate massive discounts

●︎ The future of STRs, market regulations, amenities, and the best locations to buy

The best deals don’t go to those who wait.

They go to those who know how to play the game.

07:15 - Guest Introduction: Avery Carl, STR Investment Expert

09:40 - Market Cycles: Why Timing and Strategy Matter

12:50 - The Hidden Costs of Over-Themed STRs

15:45 - How to Win in Today’s High-Interest Market

18:30 - Avoiding the Biggest Mistakes When Pricing STRs

22:10 - Leveraging Data to Find Undervalued Properties

25:55 - STR vs. Long-Term Rentals: Knowing What Works

30:20 - The Future of STR Investing: Where the Market is Headed

34:15 - Final Advice: Making Smart Moves in Any Market

Guest Bio:

Avery Carl is the author of “Short Term Rental, Long Term Wealth,” host of “The Short Term Show” podcast, CEO of The Short Term Shop, and real estate investor with 189 doors.

Guest Link:

https://www.instagram.com/theshorttermshop/

Get FREE Access to our Community and Weekly Trainings:

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Most hosts wait too long before listing their property—losing out on valuable early bookings.

What if you could start earning before your Airbnb is even ready?

In this episode, we reveal:

●︎ The 3-step pre-launch strategy to secure bookings ASAP

●︎ Why you DON’T need professional photos to go live

●︎ How to use “Pre-Launch Rates” to fill your calendar early

●︎ Why Airbnb’s algorithm rewards early bookings & reviews

●︎ How to time your launch to hit peak booking windows

Think you have to wait until your property is perfect? Think again.

01:04 - Setting Clear Monthly Revenue Goals for STR Success

02:30 - Using Data-Driven Pricing to Hit Your Income Targets

04:15 - The Power of Pre-Launch Marketing for STRs

06:00 - Picking the Right Go-Live Date for Maximum Demand

08:20 - Soft Launch Strategies to Secure 5-Star Reviews Early

10:45 - Leveraging Booking Windows to Fill Your Calendar

12:30 - Creating a Standout Airbnb Listing Without Pro Photos

14:05 - Using Mood Boards to Grab Attention and Drive Clicks

16:20 - Writing High-Converting Marketing Copy for Your Listing

18:00 - Strategic Pricing Tactics to Rank Higher on Airbnb

20:15 - The Secret to Getting Your First Bookings Fast

22:30 - How to Use Friends and Family to Boost Your Listing’s Performance

25:00 - Why Boutique STR Management Is the Future of Hosting

27:40 - Mastering Revenue Management for Long-Term Profitability

30:10 - Final Advice: Take Action and Optimize for Success

Get FREE Access to our Community and Weekly Trainings:

group.strsecrets.com

Most people think rental arbitrage is the only way to get into short-term rentals—but they’re dead wrong.

Co-hosting is more profitable, lower risk, and scales faster than traditional STR models. But how do you find properties?

In this episode, we reveal:

●︎ 7 battle-tested ways to find co-hosting deals FAST

●︎ How to earn 20-25% commission on STRs (without owning them!)

●︎ The UI Method—how to steal underperforming Airbnb listings

●︎ How to partner with realtors, landlords, and property managers for leads

●︎ Why most hosts struggle with sales—and how to fix it

Cohosting is the STR goldmine no one is talking about—until now.

Listen now and start building your empire!

02:53 - The Smarter Alternative to Arbitrage

05:02 - Boosting Profit Margins with Expert Property Management

09:55 - Leveraging Real Estate Agents for Steady Leads

15:00 - Building a Bulletproof Client Acquisition System

23:51 - The Hidden Key to 5-Star Reviews and Maximized Revenue

36:51 - Mastering Sales Calls for Explosive Growth

37:47 - The Ultimate Mindset Shift for Long-Term Success

Get FREE Access to our Community and Weekly Trainings:

group.strsecrets.com

Most people dream of quitting their soul-sucking 9-5.

Mark Palmiere actually did it.

From medical sales to short-term rental freedom—but it wasn’t easy.

He lost 5 deals immediately after quitting his job.

Faced financial uncertainty, and had to rebuild from scratch.

Now? He runs 37 high-revenue properties and is scaling to 60+ units.

Inside this episode, Mark reveals:

• Why most STR hosts fail—and how he pivoted from rental arbitrage

•The Underserved Investor (UI) method that doubled revenue from $90K to $212K

• How he chooses only high-end, well-maintained properties

• His exact strategy to scale STR operations with a lean team

• Why quitting his 6-figure job was the BEST decision he ever made

Thinking about leaving your job for STRs? Don’t do it until you hear this.

Listen now and steal the blueprint!

01:00 - Mastering Client Acquisition: The UI Method Explained

03:53 - Guest Introduction: Industry Leader Mike Riley

07:26 - From Arbitrage to Ownership: The Big Shift

10:40 - Scaling Smart: How to Grow Without Overextending

15:38 - The Game-Changing UI Strategy That Landed 17+ Properties

22:58 - Building a Rockstar Team for Operational Freedom

30:45 - The Art of Closing: Mastering High-Impact Sales Calls

33:36 - Diagnosing Listings: The Brutally Honest Approach

34:31 - Locking in Deals: The Follow-Up Formula That Works

36:52 - The Mindset Shift That Separates Amateurs from Experts

39:45 - Key Takeaways: Scaling, Sales, and Strategic Growth

Guest Bio:

Mark Palmiere owns an STR management company in San Diego, CA with 37 properties.

Guest Link:

https://www.instagram.com/mark.palmiere/reels/

Get FREE Access to our Community and Weekly Trainings:

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Most STR hosts jump into co-hosting deals blindly—and lose money before they even start.

In this episode, we break down:

• How to choose the right clients & properties (and avoid nightmare owners)

• The exact deal analysis framework that guarantees profitability

• How to set up a scalable co-hosting business model

• Why your STR niche & branding matter more than you think

• How to use real data (not guesswork) to analyze deals

The difference between profitable STR businesses and failing ones?

The right deals, the right pricing, and the right structure.

Listen now and build a STR business that prints money—not problems.

Join Our Facebook Community where we have live trainings every Wednesday:

group.strsecrets.com

03:16 – Qualifying Clients and Building Rapport

06:07 – Effective Discovery and Diagnosis

09:33 – Understanding Client Goals and Pain Points

12:20 – Solution-Oriented Questions and Presentations

15:12 – Evaluating Client Readiness and Urgency

18:45 – Setting Clear Expectations with Clients

22:10 – Common Mistakes in Sales Calls & How to Avoid Them

26:30 – Handling Objections and Overcoming Resistance

30:55 – Building Long-Term Client Relationships

35:20 – The Role of Pricing & Negotiation in Sales

39:45 – Closing Strategies for High-Conversion Sales

In this episode, Pierre-Camille Hamana, CEO of Hospitable, reveals the untold secrets behind scaling one of the biggest names in short-term rentals.

Hosted by Emanuele Pani and Mike Reilly, this is more than just another STR success story—it’s a blueprint for game-changing growth.

Here's what you'll learn:

- Most hosts settle for 5 stars. Here’s why that’s a failure..

- The mindset shift that turns 5-star reviews into 7-star experiences.

- How Hospitable scales with host feedback—this strategy made them $200M.

- The future of STR tech & direct bookings—what’s coming next.

- Why loyalty to the problem (not the solution) leads to unstoppable growth

Think you’re doing everything right?

You’re probably missing the secret that made Pierre-Camille’s empire possible.

It's time to build a business guests never forget.

01:10 - Guest Introduction: Pierre-Camille Hamana, CEO of Hospitable

02:30 - How Hospitable Grew Into a $200M Company

05:00 - Delivering a 7-Star Guest Experience

07:45 - Scaling a Tech Company with Customer Feedback

10:30 - Building a Fully Remote, High-Performance Team

13:15 - Why Hospitable Prioritizes the Problem Over the Product

16:40 - Mastering Direct Bookings with Fraud Protection

19:55 - Making STR Operations Seamless Through Automation

23:10 - The Future of STR Technology and Marketplaces

26:35 - Raising Capital from Users Instead of Investors

29:50 - Long-Term Vision: Scaling Hospitality with Purpose

32:20 - Final Advice: Staying True to Your Mission and Vision

Guest Bio:

Pierre-Camille Hamana is the founder and CEO of the vacation rental management platform Hospitable. With a software engineering and business management background, Pierre-Camille has dedicated his career to transforming the STR industry - specifically self-managers - through innovative technology solutions. Pierre started Hospitable to rent out his spare bedroom in Brussels in 2016. The company has since grown to help thousands of hosts run their vacation rentals, automating nearly 27 million reservations to date and 16 million messages annually on behalf of hosts.

Guest Link:

pc@hospitable.com

Get FREE Access to our Community and Weekly Trainings:

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• The mindset traps killing your STR growth
• The sales psychology behind a $5M exit
• The hidden framework to scale 29 properties FAST
• Why most STR hosts struggle—and how to avoid it

04:10 - Scaling to 29 Properties with a Clear Vision

06:00 - Mastering the Art of Finding Underperforming Listings

08:45 - Building a High-Performing STR Business Model

10:30 - The Power of Daily Habits and Mindset Shifts

13:00 - Leveraging Virtual Assistants for STR Automation

15:40 - Leadership and Growth: Running a STR Coaching Empire

18:10 - The Blueprint for a $5M Business Exit Strategy

20:25 - Structuring Your STR Business for Maximum Valuation

23:15 - Key Metrics That Attract High-Value Buyers

26:50 - The Role of Systems in Scaling Profitably

29:30 - The Future of STRs: Trends and Opportunities

32:00 - Final Advice: Dream Big, Take Action, Achieve Freedom

Get FREE Access to our Community and Weekly Trainings:

group.strsecrets.com

Learn how to secure cohosting contracts, manage multiple properties efficiently, and turn Airbnb into a full-time business. We’ll cover the key strategies that helped this entrepreneur escape the corporate grind and build a highly profitable short-term rental empire.

If you’re looking for a way to quit your 9-to-5 job, create passive income, or scale your Airbnb management business, this video is a must-watch. Whether you’re just starting in real estate investing or already hosting on Airbnb, these strategies will help you grow faster.

What’s your Airbnb growth goal? Drop your thoughts in the comments! Don’t forget to like, subscribe, and hit the bell for more Airbnb cohosting tips, real estate investing strategies, and passive income ideas!

#AirbnbCohosting #AirbnbHosting #RealEstateInvesting #ShortTerm

Join Our Facebook Community where we have live trainings every Wednesday: https://www.facebook.com/share/jKKgdDt62P7Kj52t/?mibextid=CTbP7E%3Futm_source%3DIG-Bio&utm_medium=strsecretsy

00:00 Elevating Leadership Standards

02:54 The Importance of Partnerships

05:50 Building a Strong Team Culture

09:13 Implementing KPIs for Growth

11:57 Effective Meeting Structures

18:07 One-on-One Engagements

01:26 - From Corporate Job to Real Estate Investor

03:29 - The Breaking Point That Led to Financial Freedom

05:03 - First STR Deal: Taking a Risk That Paid Off

07:57 - Rental Arbitrage vs. Owning: Choosing the Right Path

10:09 - Scaling STRs with Smart Systems and Automation

13:23 - Overcoming Challenges in a Competitive Market

16:00 - The Power of Virtual Assistants in STR Management

19:48 - Turning Co-Hosting Into a Profitable Business Model

22:33 - Mastering Guest Experience for Higher Ratings

26:15 - Building a Long-Term Vision for STR Growth

29:25 - Leveraging Partnerships for Real Estate Success

32:10 - Transitioning from STRs to Boutique Hotels

35:53 - The Importance of Finding the Right Mentors

38:31 - Avoiding Costly Mistakes When Buying STRs

42:00 - The Future of STRs: Where the Market Is Headed

45:10 - Final Advice: Think Bigger, Take Action, Succeed

Shawn Moore's Bio:

From reading real estate books at the public library to cashing his first wholesale check right out of college, Shawn has always been interested in finding the best opportunities in real estate. His desire to learn and achieve the best led him to seek great coaching from mentors and to be a good student. In his 22 years in the industry, Shawn has flipped homes, built a portfolio of long term rentals, attained land development deals, sold high-end luxury resort properties, and now leads the #1 short term rental education company and mastermind group in the world.

Vacation Rental Revolution:

https://www.youtube.com/@VodysseyShawnMoore

Get FREE Access to our Community and Weekly Trainings:

group.strsecrets.com

From mastering Airbnb cohosting to leveraging smart property management strategies, I’ll show you how to turn short-term rentals into a profitable income stream. These money hacks are designed for anyone looking for a career alternative, a side hustle, or a way to scale their Airbnb business to the next level.

Learn how to acquire more properties, secure cohosting contracts, and maximize profits while working fewer hours. If you’re ready to ditch the 9-to-5 grind and build a business on your terms, this video is for you.

What’s your ultimate goal with Airbnb? Share in the comments below! Don’t forget to like, subscribe, and hit the bell for more Airbnb tips, cohosting strategies, and real estate investing insights.

Join Our Facebook Community where we have live trainings every Wednesday: https://www.facebook.com/share/jKKgdDt62P7Kj52t/?mibextid=CTbP7E%3Futm_source%3DIG-Bio&utm_medium=strsecretsy

00:00 Leaving the W-2: A Leap of Faith

02:51 Understanding Your Freedom Number

05:46 Health Insurance: Navigating the Transition

11:58 Investing Your 401k: Making Smart Moves

14:46 Conventional Lending: What You Need to Know

21:49 Budgeting and Taxes: Planning for Success

25:11 Communication and Goal Setting with Your Partner

29:58 Overcoming Fear and Anxiety in Entrepreneurship

#AirbnbCohosting #AirbnbHosting #RealEstateInvesting #ShortTermRentals #FinancialFreedom #Quit9to5 #AirbnbBusiness #PassiveIncome #PropertyManagement #AirbnbTips

03:00 - Elevating Your Business Through Sales Mastery

05:30 - Breaking Limiting Beliefs Around Selling

07:45 - The Emotional Connection That Drives Sales

10:10 - Storytelling as a Game-Changer in Sales

12:20 - Overcoming Fear and Objections with Confidence

14:50 - Servant Leadership: Selling Through Impact

17:05 - The Role of Mindset in Achieving Sales Success

19:40 - The Science Behind Why People Buy

22:10 - How to Build Trust and Authority Instantly

25:30 - Scaling Revenue by Mastering Sales Psychology

28:15 - Transforming Conversations into Long-Term Clients

30:45 - The Biggest Mistakes Entrepreneurs Make in Sales

33:00 - Building a Personal Brand That Sells Itself

36:20 - The Key to Creating a Magnetic Sales Presence

39:00 - Using Social Media to Strengthen Sales Strategies

41:35 - High-Performance Habits for Sales and Leadership

44:00 - Final Advice: Becoming a Sales-Driven Leader

Guest Bio:

Kim Fitzpatrick is an Executive Business, Life + Leadership Coach who aims at maximizing the potential in everyone whose path she crosses. Kim is truly and uniquely one of a kind and her energy is infectious and comes straight from the heart. She has co-founded and built multiple-figure businesses in the online leadership coaching realm, retail, and direct sales space. Her organization was responsible for tens of millions of dollars in retail and digital wellness sales and she and her husband Jamie made history in their affiliated companies in levels of success. She has personally helped multiple women in business scale to multiple six-figure businesses and beyond. Kim is the CEO and Founder of Legacy By Kim, as well as the creator of the “Awaken Her Clarity Mastermind, The Executive Council a deep dive for business entrepreneurs and their ultimate growth, as well as subsequent courses. She also authored her morning habits and routine heart map and Journal “Be Her Now” which has been the backbone of her successful morning and life routine. She is also the Co-Host of the Podcast “Fitzlife Unfiltered” and has keynoted as well as spoken across the world on stages and at conferences to tens of thousands of people sharing her unique energy and knowledge.

Guest Link:

www.instagram.com/kim_m_fitzpatrick

Get FREE Access to our Community and Weekly Trainings:

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You'll learn how to approach property owners, present your cohosting services as a valuable solution, and handle objections to close more deals. I also share tips on building trust, communicating your unique value, and ensuring you're the go-to choice for Airbnb property management.

If you're an Airbnb cohost, real estate investor, or someone looking for an alternative to the traditional 9-5 job, this video will give you the tools to succeed in the short-term rental market. Don't miss these actionable insights to help you grow your income and achieve financial freedom through Airbnb hosting.

Would you tweak your sales process after watching this? Drop your thoughts in the comments! Like, subscribe, and hit the bell for more Airbnb cohosting tips and real estate investing strategies.

#AirbnbCohosting #ShortTermRentals #AirbnbHosting #PropertyManagement #RealEstateInvesting #SalesProcess #PassiveIncome #FinancialFreedom #AirbnbTips #AirbnbBusiness

Book a Call Here:

https://go.oncehub.com/strs-youtube

Join Our Facebook Community where we have live trainings every Wednesday: www.facebook.com/share/jKKgdDt62P7Kj52t/?mibextid=CTbP7E%3Futm_source%3DIG-Bio&utm_medium=strsecretsy

00:22 – Establishing a Sales Process

03:16 – Qualifying Clients and Building Rapport

06:07 – Effective Discovery and Diagnosis

09:33 – Understanding Client Goals and Pain Points

12:20 – Solution-Oriented Questions and Presentations

15:12 – Evaluating Client Readiness and Urgency

In this episode you’ll discover:

● The simple math behind boutique hotels and why they’re an absolute game changer

● The real reason STR investors have a massive leg up with boutique hotels

● How to finally 10x your portfolio and finally unblock scale with boutique hotels.

Register for the Boutique Hotel Training

Link: hotels.strsecrets.com

02:55 - Why Hotels Are a Game-Changer for STR Investors

04:40 - Overcoming Regulation Challenges in STRs

06:10 - Unlocking Economies of Scale in Hotel Investments

08:30 - Forced Appreciation: The Key to Wealth Building

10:00 - Reducing Competition by Targeting the Right Deals

12:00 - Establishing Revenue Thresholds for Hotel Success

14:30 - Avoiding the Trap of Buying a Job

16:20 - Creating Operational Systems for Boutique Hotels

18:00 - Building the Right Team for Hotel Operations

20:15 - Mastering Leadership and Scaling Efficiently

22:00 - Leveraging Partnerships to Expand Quickly

24:45 - Realistic Budgeting and Expense Ratios for Hotels

26:30 - Understanding Renovation Timelines and Costs

28:15 - Are You Ready to Make the Jump to Hotels?

30:40 - Key Lessons for Transitioning from STRs to Hotels

32:10 - The Importance of Experienced Partners

34:00 - Leadership Skills Needed for Larger Hospitality Projects

36:00 - Avoiding Common Pitfalls in Hotel Investments

38:30 - Setting Realistic Expectations for Hotel Operations

40:00 - Final Advice: Embracing Challenges and Achieving Growth

Join the Cause. Win the Fight.

Link: our.strsecrets.com

02:20 - Fighting Human Trafficking Through Awareness and Action

04:30 - How STR Hosts Can Be Part of the Solution

06:45 - Spotting the Signs: Proactive Measures for Hosts

08:30 - The Role of Technology in Combating Trafficking

10:00 - Collaborating with Law Enforcement for Real-Time Action

12:10 - Expanding Rescue Efforts to Global Impact

14:25 - Educating Hosts and Communities to Make a Difference

16:00 - Leveraging Events to Stay Vigilant Against Trafficking

18:30 - Integrating STR Efforts with Broader Rescue Missions

20:15 - Using STR Properties for Survivor Care

22:10 - The Power of Advocacy in Combating Exploitation

24:00 - Building Networks to Strengthen Anti-Trafficking Efforts

26:15 - Empowering Hosts to Be Key Contributors to Change

28:05 - Final Call to Action: Join the Fight Against Trafficking

Guest Bio:

Tammy Lee joins Our Rescue from Xena Therapies, a med tech company specializing in women’s health and orthopedics, focusing on philanthropic support for women. Prior to founding Xena Therapies, she was President & CEO of Recombinetics, a bio-tech company focused on human health, regenerative medicine, and animal welfare. With a background in corporate affairs at Carlson, the University of Minnesota Foundation, Delta Air Lines, and Northwest Airlines, Ms. Lee excels in coalition-building for policy change and spearheading multi-million-dollar fundraising efforts, including for trafficking prevention. She also served on the White House Interagency Task Force to Combat Trafficking in Persons and other national boards, advocating to end trafficking. Recognized as an expert, she frequently speaks on corporate philanthropy and best-in-class programs for anti-trafficking initiatives.

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04:50 - Automating Guest Communication for Seamless Hosting

06:30 - Boosting Efficiency with AI-Driven SOPs and Insights

08:15 - Building AI Systems for Enhanced Guest Experiences

10:40 - Simplifying Operations with Automated Messaging Systems

12:55 - Customizing AI Responses for Better Guest Interactions

15:10 - Unlocking Revenue Potential Through Upselling Features

17:35 - Streamlining Maintenance and Cleaning Coordination with AI

20:00 - Improving Guest Ratings Through AI Communication

22:15 - Boosting Booking Conversion with Chatbots and Widgets

24:50 - Leveraging AI to Maximize Revenue Opportunities

27:30 - Scaling STR Businesses Without Adding Headcount

30:15 - Future-Proofing Your STR Business with AI Innovation

33:10 - Key Takeaways for STR Hosts: Simplify, Scale, and Succeed

35:00 - Final Advice: Harnessing AI for Growth and Profitability

Guest Bio:

In 2021, co-founders Sam Mayes and Jay Ullrich began their journey in the short-term rental (STR) industry by establishing a management company in San Diego. Today, their team manages over 40 units, consistently delivering operational excellence and guest satisfaction. As the business expanded, one challenge became clear to almost every host they encountered: the absence of reliable, affordable, and continuous 24/7 guest support. This gap in the industry was more than just an inconvenience—it was a problem that demanded a solution. Hosts needed something more than a traditional management tool; they needed a revolutionary approach to guest communication that would transform their operations.

Guest Link:

www.hostbuddy.ai/

Use Discount Code: "STRSECRETS"

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02:25 - Scaling to $400 Million with Focused Hospitality

04:29 - Leveraging Partnerships for Rapid Expansion

06:09 - Spotting Hidden Opportunities in Hospitality Markets

08:14 - Creating Systems and Processes for Seamless Scaling

09:03 - Prioritizing Guest Experience for Maximum Impact

10:40 - Redefining Hostels with Design-Driven Concepts

13:09 - Overcoming Challenges with Unstoppable Mindset

15:00 - Understanding Avatar Demographics for Targeted Marketing

17:15 - Building Community-Driven Experiences to Increase Value

18:54 - Designing with Intention: Hiring Experts for Success

20:23 - Scaling Teams with Culture and Leadership Excellence

22:53 - Creating Sustainable Growth Through Team Building

24:09 - Leveraging Systems for Long-Term Scalability

26:36 - Building Trust Through Guest Engagement and Service

28:55 - Unlocking Zoning Strategies for Hospitality Expansion

30:00 - Educating Communities and Overcoming Stigmas

32:15 - Developing Visionary Goals for Massive Growth

34:45 - Building Multi-Million Dollar Portfolios with Hospitality Models

36:10 - Expanding Markets with Guest-Centric Strategies

38:00 - Hiring with Intentionality and Building Winning Teams

40:25 - Designing Hospitality Models Around Market Needs

42:00 - Final Advice: Dream Bigger, Execute Stronger

43:32 - Scaling Teams Through Leadership and Collaboration

44:18 - Building Resilient Mindsets for Long-Term Success

Guest Bio:

Michael Russell and Nathan St Cyr are the founders of Malama Capital and hosts of The Hotel Investor Playbook podcast.

Guest Link:

www.instagram.com/the_hotel_investor_playbook

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00:18 - Celebrating Milestones and Community Success

01:30 - Reflecting on Achievements and Vision Building

02:51 - Turning Dreams into Reality Through Action

04:22 - Setting Bigger Goals for Transformational Growth

06:11 - Breaking Down Barriers with Clear Clarity

08:01 - Defining Financial Freedom with Precision

10:25 - Mastering Self-Image to Unlock Limitless Success

12:43 - Building Habits for Long-Term Achievement

15:12 - Adjusting Plans Without Changing Goals

17:10 - Overcoming Fear and Resistance with Relentless Persistence

19:33 - Creating Accountability for Unstoppable Momentum

21:54 - Winning the Daily Battles with Consistent Habits

23:12 - Implementing Goal Cards for Focused Execution

24:50 - Leveraging Community Support for Growth and Accountability

25:10 - Final Words: Protect Your Goals and Build Lasting Habits

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01:10 - Guest Introduction: Amanda Han's Tax Expertise

02:25 - Maximizing Real Estate Tax Advantages

04:50 - Understanding the Short-Term Rental Tax Loophole

06:30 - Depreciation: A Game-Changer for Real Estate

08:45 - Breaking Down Bonus and Accelerated Depreciation

11:00 - Leveraging Tax Savings for Portfolio Growth

13:15 - Simplifying Material Participation Requirements

15:00 - Strategic Planning for Year-End Tax Benefits

17:25 - Cost Segregation Studies Demystified

19:40 - Tackling Misconceptions About Tax Strategies

21:50 - Educating Syndicators on Tax Optimization

24:10 - Key Questions to Ask When Hiring a CPA

26:30 - Turning Tax Complexity Into Clarity

28:45 - Short-Term Rentals as a Wealth-Building Tool

31:15 - Navigating Tax Planning for High-Earners

33:00 - The Power of Tax Planning for Generational Wealth

35:20 - Implementing Tax-Efficient Investment Strategies

37:45 - Understanding Tax Laws for STR Professionals

40:00 - Strategic Partnerships for Real Estate Growth

42:30 - Overcoming Common Tax Pitfalls

45:00 - Final Advice for STR and Real Estate Entrepreneurs

Guest Bio:

Amanda Han is a CPA and tax strategist who specializes in helping people use real estate to save massive amounts in taxes and keep their hard-earned money. As founder of Keystone CPA, she educates investors on how to maximize tax write-offs, legal entity strategies, tax-efficient ways to access profit, how to use 401 (k) money for real estate, and much more.

She is the author of the highly rated book Tax Strategies for the Savvy Real Estate Investor and has been featured in prominent publications including the Forbes Finance Council, Money Magazine, Talks at Google, CNBC’s Smart Money Talk Radio as well as the BiggerPockets podcasts. Today, Amanda has helped thousands of investors nationwide to save on taxes with proactive tax planning.

Connect with Guest:

https://www.instagram.com/amanda_han_cpa/

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02:10 - Guest Introduction: Danny's Creative Journey

03:30 - From Videographer to Full-Time Content Strategist

04:50 - Building a Personal Brand for STR Success

06:40 - Creating Authentic and Engaging Content

08:30 - Leveraging Social Media to Connect with Guests

10:00 - Balancing Professional and Personal Content

12:15 - Documenting Challenges to Build Trust

14:05 - Turning Vulnerability into a Strength

16:20 - Developing Consistent Content Habits

18:45 - Simplifying Content Creation with Tools

20:30 - Collecting Feedback to Improve Properties

22:50 - Measuring Content Success Through Analytics

25:00 - Scaling Social Media Presence Strategically

27:30 - Actionable Tips for Long-Term Content Success

29:45 - Breaking Through Mental Barriers for Growth

31:30 - Storytelling Techniques to Captivate Audiences

33:10 - Building a Habit of Daily Content Creation

35:20 - Adapting to Trends Without Losing Authenticity

37:00 - Focusing on Value-Driven Posts

38:50 - Strengthening STR Marketing Strategies

40:15 - Staying Resilient Amid Criticism

42:00 - Developing a Growth Mindset for STR Success

43:30 - Encouraging Small Wins to Build Momentum

Guest Bio:

Danny Mabley is a seasoned content creator and social media strategist with over a decade of experience in leveraging digital platforms for personal and professional growth. Starting with a personal weight-loss journey that went viral, Danny mastered the art of storytelling to build a significant online following. Now a vital member of the STR Secrets team, he oversees content production and social media strategies, empowering businesses to optimize their online presence. With a passion for authenticity and innovation, Danny excels in helping brands connect with audiences through engaging, impactful content.

Connect with Guest:

www.instagram.com/dannymabley

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01:15 - Guest Introduction: Chris’s Leadership Journey

03:45 - Building Robust Operational Systems

05:00 - Maintaining Quality Amid Rapid Growth

06:22 - Driving Team Engagement Through Leadership

08:00 - The Art of Delivering Exceptional Guest Experiences

09:35 - Leveraging Reviews to Elevate Standards

11:00 - Innovative Strategies for Sustainable Scaling

12:45 - Nurturing Loyalty and Retention in Teams

14:30 - Mastering Strategic Growth in Competitive Markets

16:20 - Turning Challenges into Long-Term Opportunities

18:05 - Aligning Business Goals with Team Aspirations

20:10 - Setting Boundaries for Work-Life Harmony

21:55 - Innovating Guest Experiences for Higher Returns

23:40 - Staying Ahead with Marketing and Technology

25:20 - Key Advice for Real Estate and STR Leaders

Guest Bio:

Chris Petzy is the co-owner of Seacoast Vacation Rentals, a short term rental company focused on modernizing the vacation rental experience and helping investors earn more while stressing less.

Connect with Guest:

https://www.instagram.com/chris_petzy/

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00:00 - Intro: Embracing Gratitude and Resilience

01:10 - Overcoming Challenges: Turning Pain into Power

02:00 - Mindset Mastery: Life Happens for You

03:00 - Entrepreneurial Growth Through Problem Solving

04:20 - Transformative Systems for Holiday Freedom

06:00 - Seven Steps to Elevating the CEO Role

08:00 - Building Your Perfect Week Blueprint

10:30 - Optimize Time with a Two-Week Study

12:00 - Master Delegation Through the 4R Framework

13:30 - Onboarding Excellence with Strategic Hiring

15:00 - Leadership Evolution: From Managing to Empowering

16:30 - Awareness is the Catalyst for Growth

18:00 - Achieve True Business Freedom

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01:22 - Guest Introduction

02:44 - Starting with Just Two Properties

03:18 - Quality Over Quantity Strategy

04:30 - Mastering Tough Client Conversations

05:03 - The Power of Setting Expectations Early

06:15 - Turning Down Non-Ideal Properties

07:50 - Defining Tangible Standards for Success

08:58 - Effective Direct Booking Marketing

10:30 - Expanding Into New Markets Strategically

11:12 - Managing Unique Historical Properties

12:48 - Weighing Future Opportunities vs. Standards

14:15 - Launching and Growing a Meet-Up Group

15:05 - Networking in a Regulation-Intensive Market

15:32 - The Importance of Leveraging Partnerships

16:20 - Focusing on High-Margin Operations

17:15 - Long-Term Vision: Quality and Sustainability

18:25 - Learning from Challenges and Successes

19:40 - Key Advice for Aspiring Hosts and Managers

Guest Bio

Andrew Rodriguez is the President and Co-Founder of Stay Booked, a full-service short-term rental management business that specializes in maximizing the revenue of large and unique vacation homes. In this role, he oversees all aspects of operations and guest and owner services. Outside of Stay Booked, he is the co-founder of Brews & Deals NYC, one of the largest short-term rental networking events in the country, as well as an active investor in short-term and long-term rentals across the Northeast.

Outside of real estate, Andrew spends as much time as possible in the mountains with his wife and business partner, Lindsey, and their 2-year-old son Riley. Andrew is passionate about skiing, ultrarunning, and helping others change their lives with real estate.

Connect with Guest:

www.instagram.com/andrew.j.rod

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05:42 - Strategic Team Building for Scaling

06:13 - Client Referral System for Rapid Management Growth

07:43 - Building Key Relationships with Investors

08:14 - Exponential Growth from Investor Partnerships

12:49 - Delivering Consistent Returns for Investors

17:21 - Conservative Fund Management

19:44 - Balancing Scale and Quality

22:55 - Reassessing Vision for Growth

25:43 - Choosing Best-in-Class Software

26:00 - Negotiating Vendor Contracts

26:15 - Negotiating Contracts to Optimize Costs

27:47 - Acting Fast to Avoid Operational Breakdowns

29:00 - Handling System Breakdowns Proactively

30:40 - System Optimization for Seamless Operations

31:08 - Prioritizing Functionality Over Trendy Tools

32:35 - Setting Expectations for Support with New Software

33:00 - Choosing Software for 24/7 Operations

33:58 - Importance of Solid Investor Partnerships

34:16 - Assessing Investor Trust and Relationships

34:45 - Critical Advice on Business Partnerships

36:14 - Success Secrets in Short-Term Rentals

36:14 - Honest Communication in Business Partnerships

36:42 - Scaling with Long-Term Vision

38:24 - Mistakes with Property Management Software Choices

Guest Bio

Nate Klatt is a licensed CPA with over 10 years of experience who shifted his focus earlier this year to commit to his short-term rental business fully. Nate started in short-term rentals in 2021 and, along with his partner Dan Mitchen, now owns 9 properties. Dan's real estate journey began in 2015 when he became a licensed real estate agent, quickly excelling and earning recognition as a top agent within his brokerage. Prior to this, Nate and Dan completed approximately 15 flips during 2020 and 2021 before transitioning to a more scalable business model in short-term rentals. Previously, Nate worked at a Y Combinator-backed AI startup, where he helped drive a 10x revenue increase. As co-founders of HomeHop, Nate and Dan have grown their property management portfolio from 1 to over 50 properties in just a year. They raised $2 million to acquire around 25 homes in Cleveland and are preparing to raise another $5 million next year for their second fund. HomeHop’s focus on leveraging technology and optimizing processes has been key to scaling in a competitive short-term rental market.

Connect with Guests:

HomeHopPM.com

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02:27 - Overcoming Overwhelm and Transformation

04:19 - Guest Introduction: Marisa Grover

05:11 - Realizing the Need for Radical Change

08:29 - Taking Bold Steps to Reclaim Balance

09:16 - Game-Changing Documentation for Success

10:00 - Strategic VA Hiring for Freedom

11:01 - Quick, Dramatic Workload Reduction

13:39 - Mastering Delegation for Growth

14:14 - Bulletproof System Documentation

16:14 - Empowering the Team Through Leadership

19:45 - Focusing on High-Impact, Profitable Assets

24:03 - Selecting Ideal, Aligned Clients

27:00 - Building Strong Owner Partnerships

30:13 - Relentless Perseverance for Success

Marisa Grover's Bio

Marisa Grover is originally from Utah and then moved to Texas 4 years ago. She got into Airbnb in 2021 with a small property near the university in her town, and she loved it. What started there, turned into building a family of 9 STRs, and 10 LTRS, and then creating a cohosting company 3 times. Marisa hosted over 1,000 guests and grew from 1-55 properties in 3 years. She is a mom of two boys under 4 among all of this.

Connect with Marisa Grover

www.instagram.com/marisagrover

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05:18 - Guests Sarah and Annette join.

06:00 - Guests introduce their business.

08:37 - How they entered short-term rentals.

17:12 - Tips on choosing a business partner.

20:29 - Adapting communication styles in leadership.

30:41 - Balancing career and personal life.

34:50 - Building a personal brand.

43:43 - Using a “legacy scorecard” for tracking.

48:31 - Overview of “Thanks for Visiting.”

51:34 - Top tip for rental success.

Sarah and Annette's Bio

As short-term rental owners and operators for 10 years and counting, Sarah and Annette founded the Thanks For Visiting podcast and their online educational platform to bring their diverse knowledge to hosts ready to grow their businesses.

Sarah and Annette met at a Columbus, Ohio City Council Meeting fighting for their right to host homes on a short-term rental basis. The two shared a belief that the short-term rental industry needs hosts to be more hospitable. Every resource they’d come across in growing their own businesses was purely profit-driven, and “heads in beds” just wasn’t their style.

Connect with Sarah and Annette

https://www.instagram.com/thanksforvisiting_

Connect with the Hosts

Michael Sjogren: Short Term Rental Secrets Facebook Group | Clubhouse | Instagram | Youtube | Facebook Page | Linkedin

https://linktr.ee/mikesjogren

Emanuele Pani: Clubhouse | Instagram | Facebook | Linkedin

00:00 Introduction

00:29 Meet Isaac Oswalt

01:31 Isaac's Real Estate Journey

02:14 The Spillway Lodges Project

08:24 Development vs. Building

11:34 The Role of a Developer

13:51 Key Relationships in Development

18:36 Navigating Local Government for Development

20:03 Is Money a Barrier to Entry in Development?

21:03 Steps to Secure and Develop Land

22:23 The Importance of Patience and Capital in Development

26:03 Balancing Active and Passive Income

29:08 Introducing Spillway Lodges

32:35 Marketing Strategies for Hospitality Projects

35:41 Final Thoughts and Success Secrets

Isaac Oswalt's Bio

Isaac Oswalt is a real estate developer of boutique resorts and workforce housing. He created a 36-unit boutique resort in Bellaire, Michigan, called Spillway Lodges. He owns a development, construction, and management firm—1983 Company. Based in West Michigan, they execute their business throughout the state and empower other current and future developers to create long-term assets within their own communities.

Connect with Isaac

www.instagram.com/isaacoswalt

isaac@1983company.com

Connect with the Hosts

Michael Sjogren: Short Term Rental Secrets Facebook Group | Clubhouse | Instagram | Youtube | Facebook Page | Linkedin

https://linktr.ee/mikesjogren

Emanuele Pani: Clubhouse | Instagram | Facebook | Linkedin

00:00 Introduction to the Podcast

00:20 Today's Episode Overview

01:39 Guest Introduction: Eric Cabral

02:25 Eric's Journey in Branding and Marketing

04:11 Transition to Real Estate Investing

07:38 Building a Personal Brand

11:57 Practical Tips for Content Creation

18:06 Shiny Object Syndrome: Juggling Multiple Roles

18:26 Finding Your Niche: The Power of Intentional Branding

19:47 Consistency is Key: Building Your Platform

21:04 The Long Game: Podcasting Tips and Strategies

23:59 Outsourcing and Leveraging Your Podcast

27:08 Overcoming Content Creation Fears

31:19 Living in Service: The Ultimate Success Secret

34:08 Final Thoughts and Resources

Erik Cabral's Bio

Erik Cabral is a leading expert in brand development, trusted by Fortune 100 and Inc. 5000 companies to define and deliver their core messages effectively. Having built thousands of brands over his quarter-of-a-century career, Erik has now created a stage that he's shared with powerhouse brands like Shark Tank's Matt Higgins and Kevin Harrington, VaynerMedia, David Meltzer, and Hal Elrod of the Miracle Morning. Erik is known for his expertise in branding, content creation, podcast strategies, and community building. As the founder of On Air Brands, Be Your Brand, PodMAX, and the Mindado Investment Group, Erik is dedicated to helping entrepreneurs develop their personal and corporate brands through podcasting and media strategies. His work has been featured in major publications and has contributed to raising millions in capital for his investor clients.

Connect with Erik

www.erikcabral.co

https://www.instagram.com/erikecabral

https://www.facebook.com/erikecabral

https://www.linkedin.com/in/erikcabral/

https://www.youtube.com/@erikcabralbrand

Connect with the Hosts

Michael Sjogren: Short Term Rental Secrets Facebook Group | Clubhouse | Instagram | Youtube | Facebook Page | Linkedin

https://linktr.ee/mikesjogren

Emanuele Pani: Clubhouse | Instagram | Facebook | Linkedin

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00:00 Introduction and Welcome

00:26 Weather and Gratitude

01:32 Introducing Debbie Todd

02:58 Debbie's Journey into STRs

04:25 The Give Back Initiative

09:46 Expanding the Impact

19:42 Future Vision and Community Involvement

26:00 Final Thoughts and Success Tips

Debbie Todd's Bio

Debbie Todd is a mother of three, physical therapist, and co-founder of The Woodlands at Hocking Hills in Logan, Ohio with her husband Jeff. Together, they remotely manage two multigenerational vacation rentals from Columbus, Ohio. Passionate about giving back, they support 12 charities, sponsor a child through Compassion International, and offer free stays to those in need, all through their vacation rental platform. Since 2021, they’ve contributed nearly $53,000 and volunteered extensively to impact their community. Debbie recently partnered with the Hocking Hills Tourism Association to launch Hocking Hills Gives Back.

Debbie's work goes beyond just hosting and hospitality; she actively involves her children, guests, and the community in efforts to make a greater impact, fostering unique and purposeful connections. Her inspiring story has been featured on podcasts, radio shows, and in various publications, including her chapter in Hospitable Host, Volume 3.

After years of pursuing her vision and seeking to expand her reach, Debbie partnered with Hospitable Hosts to launch the Hospitable Hosts Impact Community. This initiative provides hosts around the world various opportunities to give back through real estate, strengthening the global impact of the short-term rental community.

Connect with Debbie

https://www.instagram.com/hospitablehosts

https://www.instagram.com/debbie.monti.kay

https://www.hospitablehosts.com/give-back

Connect with the Hosts

Michael Sjogren: Short Term Rental Secrets Facebook Group | Clubhouse | Instagram | Youtube | Facebook Page | Linkedin

https://linktr.ee/mikesjogren

Emanuele Pani: Clubhouse | Instagram | Facebook | Linkedin

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00:00 Rebuilding After the Storm: A Global Effort

00:36 Welcome to the Short Term Rental Secrets Podcast

01:09 Storm Preparedness and Response

03:23 Introducing Tyler Coon: Expert Insights

04:56 Tyler's Personal Storm Experience

08:45 Navigating Insurance and Repairs

15:28 Managing Bookings and Misinformation

17:53 Immediate Impact and Response

18:25 Handling Cancellations and Prioritizing First Responders

19:53 Media Perception vs. Reality

22:56 Community Mobilization and Support

24:51 Insurance and Co-Hosting Considerations

27:01 Long-Term Recovery and Preparedness

33:27 Conclusion and Final Thoughts

Tyler Coon's Bio

Tyler Coon is the premier real estate agent of choice when it comes to Short Term Rental acquisitions. As your partner in the process of finding your next investment, Tyler and his Savvy Realty team stand by your side. From purchasing directly with Tyler in the North Carolina mountains to other vacation destinations in the country, a Savvy Agent will always be the best choice for your next investment.

Connect with Tyler

www.calendly.com/TylerCoon

https://www.instagram.com/savvy.realty/

Connect with the Hosts

Michael Sjogren: Short Term Rental Secrets Facebook Group | Clubhouse | Instagram | Youtube | Facebook Page | Linkedin

https://linktr.ee/mikesjogren

Emanuele Pani: Clubhouse | Instagram | Facebook | Linkedin

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00:00 Introduction

01:26 Gambling and Personal Preferences

02:09 Boutique Hotel Con Recap

04:23 Raising Capital and Pitching Deals

07:13 Hotel Operations and Team Building

07:59 Networking and Personal Stories

12:34 Mindset and Decision Making

18:15 Setting Effective Goals

19:02 Building a Dream Facility

20:32 The Importance of Personal Branding

21:09 Launching Group Coaching

21:32 Purpose of Goals: Growth Over Achievement

22:52 Accountability Partners and Goal Setting

24:34 Protecting Your Goals

26:51 Balancing Responsibilities and Ambitions

28:01 Pushing Beyond Comfort Zones

28:55 The Power of Vision and Persistence

34:16 Join the STR Secrets Community

Connect with the Hosts

Michael Sjogren: Short Term Rental Secrets Facebook Group | Clubhouse | Instagram | Youtube | Facebook Page | Linkedin

https://linktr.ee/mikesjogren

Emanuele Pani: Clubhouse | Instagram | Facebook | Linkedin

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00:00 Overcoming the Fear of Learning

00:11 Introducing Kim Herrlein: From STRs to Boutique Hotels

02:00 Kim's Journey into Real Estate

05:12 First STR Project: Transforming a Home for Large Groups

10:21 Mindset and Overcoming Fear in Real Estate

20:17 Scaling Up: From STRs to Boutique Hotels

25:12 Revitalizing the Community

27:30 Designing a Boutique Hotel

28:32 Challenges in Renovation

32:20 Operational Differences: STRs vs. Boutique Hotels

35:19 Tech Stack and Online Presence

43:11 Marketing and Group Buyouts

46:15 Final Thoughts and Success Tips

Kim Herrlein's Bio

Kim Herrlein is the Chief Leisure Officer at Purveyors of Leisure, a boutique vacation rental management company in Greater Palm Springs, Southern California. Kim’s interest in travel began at a young age when she was fortunate enough to spend holidays abroad in Europe, traveling with extended family and friends, temporarily residing at unique vacation rentals; such as a magical poolside villa in the south of France, an enchanting Tuscan castle and vineyard, or an artsy Swiss chalet. Her love of travel, art and architecture, and design was ignited and more poignantly, a simple joy was sparked, gathering with loved ones on vacation was fun!

Connect with Kim

https://linktr.ee/purveyorsofleisure

https://www.faintingcouch.com

https://www.facebook.com/The.FaintingCouchHotel/

https://www.instagram.com/the.faintingcouch/

Connect with the Hosts

Michael Sjogren: Short Term Rental Secrets Facebook Group | Clubhouse | Instagram | Youtube | Facebook Page | Linkedin

https://linktr.ee/mikesjogren

Emanuele Pani: Clubhouse | Instagram | Facebook | Linkedin

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