DJing. Creative work. Academia. Plans to become a professor. Different jobs, different ideas, and a whole lot of hunger to figure out where she belonged.

Looking back, all those side quests were building toward something.

In Episode 2 of OUTWORK, Alex tells the story of how she found real estate media and turned that creative drive into a successful business.

Then we flip the conversation: knowing everything she knows now, what would Alex do if she had to start her real estate media business again from absolute zero?

We get into finding your first clients, what she’d focus on, what she’d ignore, and how she’d approach building the business today.

Part origin story. Part playbook for starting over.

OUTWORK is about building the business — and figuring out the life you actually want it to create.

Supporting Sponsor: HDPhotoHub

New episodes weekly.

Welcome to the first episode of OUTWORK.

Alex Coombs and Oliver Ward have built two very different real estate media businesses. Alex went from shooting everything herself to building a team and an office. Oliver deliberately stayed lean, eventually building businesses in both Canada and Costa Rica around the life he wanted to live.

In this episode, we go back to the beginning.

Why do so many people get into real estate media and quit? How much does being a great photographer actually matter? When should you make your first hire? And how do you build a business without accidentally creating another job you can’t escape?

We talk about our first hires, rejection, customer service, scaling vs. staying small, company culture, AI, the future of real estate video, and some of the mistakes we’d avoid if we were starting again today.

We also get into something bigger: what are you actually building all of this for?

We’ve taken very different paths, but we both believe your business should be designed around the life you want—not the other way around.

If you’re starting a real estate media business, grinding it out as a solo shooter, or already running a team and wondering what’s next, this is where OUTWORK starts.

Build the business. Escape the job.