Is This Working?!What if the most interesting thing about work isn’t what we do—but what it does to us? Is This Working?! dives into meaningful work and the messy humans who do it. As AI reshapes industries and upends old definitions of success, social entrepreneur and Stanford GSB lecturer Connor Diemand-Yauman talks with extraordinary people about both sides of the story: the outer work (what they built, how they pivoted, the tactics that actually worked) and the inner work(the therapy, the doubt, the failure) it took to get there. Because when the world is changing this fast, maybe these stories are the only way to know if any of this is actually working.enWed, 04 Nov 2026 19:29:10 -0000Wed, 04 Nov 2026 19:29:10 -0000https://rss2.flightcast.com/wbxvf8vgyotuwkiuw1711u1r.xmlFlightcast RSS Feed GeneratorIs This Working?!https://files.flightcast.com/workspaces/tv31t1erpjv2lb9jp39i59ra/01KCWAXQJ3EJEHSVQ63PH27KW8/final_square_cover__1_.jpghttps://rss2.flightcast.com/wbxvf8vgyotuwkiuw1711u1r.xmlWhat if the most interesting thing about work isn’t what we do—but what it does to us?

Is This Working?! dives into meaningful work and the messy humans who do it. As AI reshapes industries and upends old definitions of success, social entrepreneur and Stanford GSB lecturer Connor Diemand-Yauman talks with extraordinary people about both sides of the story: the outer work (what they built, how they pivoted, the tactics that actually worked) and the inner work(the therapy, the doubt, the failure) it took to get there.

Because when the world is changing this fast, maybe these stories are the only way to know if any of this is actually working.

]]>episodicConnor Diemand-YaumanConnor Diemand-Yaumanhello@isthisworking.comWhat if the most interesting thing about work isn’t what we do—but what it does to us? Is This Working?! dives into meaningful work and the messy humans who do it. As AI reshapes industries and upends old definitions of success, social entrepreneur and Stanford GSB lecturer Connor Diemand-Yauman talks with extraordinary people about both sides of the story: the outer work (what they built, how they pivoted, the tactics that actually worked) and the inner work(the therapy, the doubt, the failure) it took to get there. Because when the world is changing this fast, maybe these stories are the only way to know if any of this is actually working.What if the most interesting thing about work isn’t what we do—but what it does to us?falsenoIs Everything at Work Really an Emergency? – Former Bomb Tech Devan TrammelDevan Trammel used to walk toward live bombs for a living. Literally. That was his job on a US Air Force bomb squad, which he joined at 19. From there, he helped start a technology incubator at the Pentagon before getting an MBA at Stanford. After all that, he has a very short list of what counts as risk at work: "someone dying, or you're going to bankrupt the entire business, or you're going to really hurt people." Everything else, he says, is "really just management." Connor and Devan get into: the question he asks in front of a live bomb: "What is the worst thing that could absolutely happen in this scenario, and what actions would I have to take to make that happen?" why he hid his mistakes from his team, and the commander whose one story made him call everyone who had ever worked for him to apologize why his team took three minutes to write down what they thought before anyone said a word, so nobody would just agree with the boss the crochet snail he pulled out in the middle of the test that decided whether he'd lead a bomb team the movie soundtrack he listens to on the way to a bomb If everything at work feels like a live bomb, or you've been hiding your mistakes from your team, start here. Chapters 00:00:00 Intro 00:01:33 Why he joined the bomb squad at 19 00:03:59 What the job actually is 00:06:27 The leaking package in England 00:09:15 The 250-pound bomb in Charleston 00:13:50 Staying calm in front of a live bomb 00:15:11 Why he stopped pretending to be perfect 00:20:18 Why the leader talks last 00:22:51 Why attitude is non-negotiable 00:24:16 Humor in the field 00:28:22 Why harder work needs more humor 00:30:35 Volunteering for Thanksgiving week in Appalachia 00:32:20 Treating the food crew like Michelin chefs 00:34:00 Leaving the military 00:37:29 Should leaders think more about death? 00:39:10 Most risk isn't really risk 00:40:53 What he's still working on 00:42:44 The billboardflightcast:01M6H7K456M0G239N9634DAKS5Wed, 04 Nov 2026 19:29:10 -0000Devan Trammel used to walk toward live bombs for a living. Literally. That was his job on a US Air Force bomb squad, which he joined at 19. From there, he helped start a technology incubator at the Pentagon before getting an MBA at Stanford.

After all that, he has a very short list of what counts as risk at work: "someone dying, or you're going to bankrupt the entire business, or you're going to really hurt people."

Everything else, he says, is "really just management."

Connor and Devan get into:

  • the question he asks in front of a live bomb: "What is the worst thing that could absolutely happen in this scenario, and what actions would I have to take to make that happen?"
  • why he hid his mistakes from his team, and the commander whose one story made him call everyone who had ever worked for him to apologize
  • why his team took three minutes to write down what they thought before anyone said a word, so nobody would just agree with the boss
  • the crochet snail he pulled out in the middle of the test that decided whether he'd lead a bomb team
  • the movie soundtrack he listens to on the way to a bomb

If everything at work feels like a live bomb, or you've been hiding your mistakes from your team, start here.

Chapters

  • 00:00:00 Intro
  • 00:01:33 Why he joined the bomb squad at 19
  • 00:03:59 What the job actually is
  • 00:06:27 The leaking package in England
  • 00:09:15 The 250-pound bomb in Charleston
  • 00:13:50 Staying calm in front of a live bomb
  • 00:15:11 Why he stopped pretending to be perfect
  • 00:20:18 Why the leader talks last
  • 00:22:51 Why attitude is non-negotiable
  • 00:24:16 Humor in the field
  • 00:28:22 Why harder work needs more humor
  • 00:30:35 Volunteering for Thanksgiving week in Appalachia
  • 00:32:20 Treating the food crew like Michelin chefs
  • 00:34:00 Leaving the military
  • 00:37:29 Should leaders think more about death?
  • 00:39:10 Most risk isn't really risk
  • 00:40:53 What he's still working on
  • 00:42:44 The billboard

]]>Is Everything at Work Really an Emergency? – Former Bomb Tech Devan Trammelfull2672falseDevan Trammel used to walk toward live bombs for a living. Literally. That was his job on a US Air Force bomb squad, which he joined at 19. From there, he helped start a technology incubator at the Pentagon before getting an MBA at Stanford. After all that, he has a very short list of what counts as risk at work: "someone dying, or you're going to bankrupt the entire business, or you're going to really hurt people." Everything else, he says, is "really just management." Connor and Devan get into: the question he asks in front of a live bomb: "What is the worst thing that could absolutely happen in this scenario, and what actions would I have to take to make that happen?" why he hid his mistakes from his team, and the commander whose one story made him call everyone who had ever worked for him to apologize why his team took three minutes to write down what they thought before anyone said a word, so nobody would just agree with the boss the crochet snail he pulled out in the middle of the test that decided whether he'd lead a bomb team the movie soundtrack he listens to on the way to a bomb If everything at work feels like a live bomb, or you've been hiding your mistakes from your team, start here. Chapters 00:00:00 Intro 00:01:33 Why he joined the bomb squad at 19 00:03:59 What the job actually is 00:06:27 The leaking package in England 00:09:15 The 250-pound bomb in Charleston 00:13:50 Staying calm in front of a live bomb 00:15:11 Why he stopped pretending to be perfect 00:20:18 Why the leader talks last 00:22:51 Why attitude is non-negotiable 00:24:16 Humor in the field 00:28:22 Why harder work needs more humor 00:30:35 Volunteering for Thanksgiving week in Appalachia 00:32:20 Treating the food crew like Michelin chefs 00:34:00 Leaving the military 00:37:29 Should leaders think more about death? 00:39:10 Most risk isn't really risk 00:40:53 What he's still working on 00:42:44 The billboardDevan TrammelShould My Kid Still Go to College? – WGU President Scott PulsipherScott Pulsipher isn't scared of what AI will do to education. Which is strange, given that he runs Western Governors University, the largest university in the country: nonprofit, online, nearly 200,000 students. A lot of other university leaders are scared, and he says they probably should be. He doesn't believe anyone can predict the future of work, so WGU looks 12 to 36 months out at how jobs are actually changing and works backward into what students learn. He'd also like to shrink the four-year degree to one or two years, with the rest earned on the job. So Connor asks him the question everybody actually wants answered: should my kid go to college? They get into: his answer, from the person with the most to lose from saying no why job skills now expire faster than a four-year degree can teach them his "yes and no" on whether college is still the path to the American dream the question he uses to test whether a college remembers who it's for: "what does the world lose if you don't exist?" the week at Amazon when twenty-six of his peers told him to his face how he actually made them feel, and the sentence from his boss that put him back together the three things that have to be true before anyone can change Plus: a rocket scientist uncle who shook satellites until the parts fell off, how he went from twenty years in tech to a university he'd never heard of, and six kids, four grandkids, and a wife who took one look at him that Friday night and asked what happened. If you're trying to work out whether college is still worth it, for your kid or for yourself, start here.flightcast:01M5CBQJ4ZY8ZR6ZK60GR69TEAWed, 21 Oct 2026 19:21:56 -0000Scott Pulsipher isn't scared of what AI will do to education.

Which is strange, given that he runs Western Governors University, the largest university in the country: nonprofit, online, nearly 200,000 students. A lot of other university leaders are scared, and he says they probably should be. He doesn't believe anyone can predict the future of work, so WGU looks 12 to 36 months out at how jobs are actually changing and works backward into what students learn. He'd also like to shrink the four-year degree to one or two years, with the rest earned on the job.

So Connor asks him the question everybody actually wants answered: should my kid go to college?

They get into:

  • his answer, from the person with the most to lose from saying no
  • why job skills now expire faster than a four-year degree can teach them
  • his "yes and no" on whether college is still the path to the American dream
  • the question he uses to test whether a college remembers who it's for: "what does the world lose if you don't exist?"
  • the week at Amazon when twenty-six of his peers told him to his face how he actually made them feel, and the sentence from his boss that put him back together
  • the three things that have to be true before anyone can change

Plus: a rocket scientist uncle who shook satellites until the parts fell off, how he went from twenty years in tech to a university he'd never heard of, and six kids, four grandkids, and a wife who took one look at him that Friday night and asked what happened.

If you're trying to work out whether college is still worth it, for your kid or for yourself, start here.

]]>Should My Kid Still Go to College? – WGU President Scott Pulsipherfull3023trueScott Pulsipher isn't scared of what AI will do to education. Which is strange, given that he runs Western Governors University, the largest university in the country: nonprofit, online, nearly 200,000 students. A lot of other university leaders are scared, and he says they probably should be. He doesn't believe anyone can predict the future of work, so WGU looks 12 to 36 months out at how jobs are actually changing and works backward into what students learn. He'd also like to shrink the four-year degree to one or two years, with the rest earned on the job. So Connor asks him the question everybody actually wants answered: should my kid go to college? They get into: his answer, from the person with the most to lose from saying no why job skills now expire faster than a four-year degree can teach them his "yes and no" on whether college is still the path to the American dream the question he uses to test whether a college remembers who it's for: "what does the world lose if you don't exist?" the week at Amazon when twenty-six of his peers told him to his face how he actually made them feel, and the sentence from his boss that put him back together the three things that have to be true before anyone can change Plus: a rocket scientist uncle who shook satellites until the parts fell off, how he went from twenty years in tech to a university he'd never heard of, and six kids, four grandkids, and a wife who took one look at him that Friday night and asked what happened. If you're trying to work out whether college is still worth it, for your kid or for yourself, start here.Scott PulsipherWho Wins the AI Race? Probably Not Who You Think – Former Bain Capital Executive Mark NunnellyThere are two types of hyper successful people. The ones who have an answer for everything, and the ones you actually want to talk to. Mark Nunnelly is squarely in the second camp. He joined Bain Capital in its early years and became one of the most successful investors in the world. Then, in his late fifties, he went to work for the governor of Massachusetts, where he led 5,000 people and started the state's first cybersecurity department from scratch. And he spent his hour with Connor talking about what he doesn't know. About parenting, which he says he got "spectacularly wrong" in places and calls the best thing he ever did. About capitalism, which he still calls the winning model even though "we have not had the shared prosperity that we need." And about AI, where his read is that "we're looking at the movie in its first minutes," and everyone is already describing the final scene. They get into: why the companies we think are winning AI today probably won't be the ones that win why "follow your passion" needs an asterisk, and the evidence to look at instead what he would do with $100 million to do the most good, and why it starts with medicine thirty years of work on American education, and why it left him less hopeful and more determined the eulogy test, and the two decisions he ranks above everything else he did If you're making big calls right now without knowing how any of this ends, this one is for you. Chapters 00:00:00 Intro 00:01:09 From a preacher's kid to private equity 00:03:46 People can't know how much you know until they know how much you care 00:04:57 Leaving Bain for public service 00:06:43 Luck, and following your passion with an asterisk 00:10:29 Look at the pattern, and get comfortable failing 00:12:04 The eulogy test, marriage and fatherhood 00:15:37 Thirty years of education reform 00:20:45 Choosing possibility over catastrophe on AI 00:29:24 Capitalism and shared prosperity 00:32:11 "Just tell me it's going to be okay" 00:32:45 The $100 million question 00:35:25 Why today's AI winners won't stay the winners 00:38:36 Two handfuls of unelected people 00:39:56 A kid off the turnip truck from Kentucky 00:43:20 A year around the world with a small backpack 00:44:42 Intensely, neurotically calm 00:45:49 The next chapterflightcast:01M4B6NCTQFBC5S54CFKZ4X09QWed, 07 Oct 2026 21:19:47 -0000There are two types of hyper successful people. The ones who have an answer for everything, and the ones you actually want to talk to. Mark Nunnelly is squarely in the second camp.

He joined Bain Capital in its early years and became one of the most successful investors in the world. Then, in his late fifties, he went to work for the governor of Massachusetts, where he led 5,000 people and started the state's first cybersecurity department from scratch.

And he spent his hour with Connor talking about what he doesn't know. About parenting, which he says he got "spectacularly wrong" in places and calls the best thing he ever did. About capitalism, which he still calls the winning model even though "we have not had the shared prosperity that we need." And about AI, where his read is that "we're looking at the movie in its first minutes," and everyone is already describing the final scene.

They get into:

  • why the companies we think are winning AI today probably won't be the ones that win
  • why "follow your passion" needs an asterisk, and the evidence to look at instead
  • what he would do with $100 million to do the most good, and why it starts with medicine
  • thirty years of work on American education, and why it left him less hopeful and more determined
  • the eulogy test, and the two decisions he ranks above everything else he did

If you're making big calls right now without knowing how any of this ends, this one is for you.

Chapters

  • 00:00:00 Intro
  • 00:01:09 From a preacher's kid to private equity
  • 00:03:46 People can't know how much you know until they know how much you care
  • 00:04:57 Leaving Bain for public service
  • 00:06:43 Luck, and following your passion with an asterisk
  • 00:10:29 Look at the pattern, and get comfortable failing
  • 00:12:04 The eulogy test, marriage and fatherhood
  • 00:15:37 Thirty years of education reform
  • 00:20:45 Choosing possibility over catastrophe on AI
  • 00:29:24 Capitalism and shared prosperity
  • 00:32:11 "Just tell me it's going to be okay"
  • 00:32:45 The million question
  • 00:35:25 Why today's AI winners won't stay the winners
  • 00:38:36 Two handfuls of unelected people
  • 00:39:56 A kid off the turnip truck from Kentucky
  • 00:43:20 A year around the world with a small backpack
  • 00:44:42 Intensely, neurotically calm
  • 00:45:49 The next chapter

]]>Who Wins the AI Race? Probably Not Who You Think – Former Bain Capital Executive Mark Nunnellyfull2926trueThere are two types of hyper successful people. The ones who have an answer for everything, and the ones you actually want to talk to. Mark Nunnelly is squarely in the second camp. He joined Bain Capital in its early years and became one of the most successful investors in the world. Then, in his late fifties, he went to work for the governor of Massachusetts, where he led 5,000 people and started the state's first cybersecurity department from scratch. And he spent his hour with Connor talking about what he doesn't know. About parenting, which he says he got "spectacularly wrong" in places and calls the best thing he ever did. About capitalism, which he still calls the winning model even though "we have not had the shared prosperity that we need." And about AI, where his read is that "we're looking at the movie in its first minutes," and everyone is already describing the final scene. They get into: why the companies we think are winning AI today probably won't be the ones that win why "follow your passion" needs an asterisk, and the evidence to look at instead what he would do with $100 million to do the most good, and why it starts with medicine thirty years of work on American education, and why it left him less hopeful and more determined the eulogy test, and the two decisions he ranks above everything else he did If you're making big calls right now without knowing how any of this ends, this one is for you. Chapters 00:00:00 Intro 00:01:09 From a preacher's kid to private equity 00:03:46 People can't know how much you know until they know how much you care 00:04:57 Leaving Bain for public service 00:06:43 Luck, and following your passion with an asterisk 00:10:29 Look at the pattern, and get comfortable failing 00:12:04 The eulogy test, marriage and fatherhood 00:15:37 Thirty years of education reform 00:20:45 Choosing possibility over catastrophe on AI 00:29:24 Capitalism and shared prosperity 00:32:11 "Just tell me it's going to be okay" 00:32:45 The $100 million question 00:35:25 Why today's AI winners won't stay the winners 00:38:36 Two handfuls of unelected people 00:39:56 A kid off the turnip truck from Kentucky 00:43:20 A year around the world with a small backpack 00:44:42 Intensely, neurotically calm 00:45:49 The next chapterMark NunnellyThe Magician's Guide to Blowing Your Colleagues' Minds – Magic Patio Founder Andrew EvansAndrew Evans is a magician, but his real job? Gaining people's trust. Whether he's headlining at The Magic Patio, the SF venue he created that now sells out three months in advance, or working as a design lead at IDEO and Nike, helping clients tackle problems differently, his work is always about one fundamental question: How do I earn the trust of everyone in this room? His answer? Surprise. Take the disaster of a video call he had with a team in Korea. Echo, feedback, nobody able to see anybody. Finally, after fifteen grueling minutes, they get it working, and Andrew clicks through to the agenda slide he'd built a week earlier. First item: 9:00 to 9:15, technical difficulties. Everybody laughed, and then everybody relaxed. "We're not behind on anything. This is right where we're supposed to be." That's the magic trick: let people think one thing, and when they realize it was something else entirely, they know they're in good hands. In this episode, Andrew and Connor get into why he treats a flop as a persona failure and not a personal one, the ten-second question to ask before you design anything for your colleagues, and why making his Zoom setup more professional made people trust him less. If you want your next pitch or offsite to bring some real joy instead of corporate cringe, this episode's for you. Chapters 00:00:00 The mutant magician who infected IDEO's DNA 00:00:53 The BDSM approach to opening a magic show 00:08:22 Technical difficulties: the slide deck joke that built trust 00:11:04 Consider the context: the hack for creating wonder 00:14:39 Casting clients as investors 00:16:13 Snapping people out of Zoom multitasking 00:18:13 The psychology of deception 00:25:34 Adult-like wonder vs childlike wonder 00:30:26 Be creative by standing on the backs of giants 00:36:00 Being liked: the persona vs the person 00:40:41 Purpose is a byproduct, not something you find 00:43:19 From roller coasters to the Magic Patio 00:46:32 Shake up your routines and add randomness 00:49:24 Let's do some magicflightcast:01M36JH5NSAA3SSEJ2NYGY757VWed, 23 Sep 2026 12:29:14 -0000Andrew Evans is a magician, but his real job? Gaining people's trust.

Whether he's headlining at The Magic Patio, the SF venue he created that now sells out three months in advance, or working as a design lead at IDEO and Nike, helping clients tackle problems differently, his work is always about one fundamental question:

How do I earn the trust of everyone in this room?

His answer? Surprise.

Take the disaster of a video call he had with a team in Korea. Echo, feedback, nobody able to see anybody. Finally, after fifteen grueling minutes, they get it working, and Andrew clicks through to the agenda slide he'd built a week earlier. First item:

9:00 to 9:15, technical difficulties.

Everybody laughed, and then everybody relaxed. "We're not behind on anything. This is right where we're supposed to be."

That's the magic trick: let people think one thing, and when they realize it was something else entirely, they know they're in good hands.

In this episode, Andrew and Connor get into why he treats a flop as a persona failure and not a personal one, the ten-second question to ask before you design anything for your colleagues, and why making his Zoom setup more professional made people trust him less.

If you want your next pitch or offsite to bring some real joy instead of corporate cringe, this episode's for you.

Chapters

  • 00:00:00 The mutant magician who infected IDEO's DNA
  • 00:00:53 The BDSM approach to opening a magic show
  • 00:08:22 Technical difficulties: the slide deck joke that built trust
  • 00:11:04 Consider the context: the hack for creating wonder
  • 00:14:39 Casting clients as investors
  • 00:16:13 Snapping people out of Zoom multitasking
  • 00:18:13 The psychology of deception
  • 00:25:34 Adult-like wonder vs childlike wonder
  • 00:30:26 Be creative by standing on the backs of giants
  • 00:36:00 Being liked: the persona vs the person
  • 00:40:41 Purpose is a byproduct, not something you find
  • 00:43:19 From roller coasters to the Magic Patio
  • 00:46:32 Shake up your routines and add randomness
  • 00:49:24 Let's do some magic

]]>The Magician's Guide to Blowing Your Colleagues' Minds – Magic Patio Founder Andrew Evansfull3544falseAndrew Evans is a magician, but his real job? Gaining people's trust. Whether he's headlining at The Magic Patio, the SF venue he created that now sells out three months in advance, or working as a design lead at IDEO and Nike, helping clients tackle problems differently, his work is always about one fundamental question: How do I earn the trust of everyone in this room? His answer? Surprise. Take the disaster of a video call he had with a team in Korea. Echo, feedback, nobody able to see anybody. Finally, after fifteen grueling minutes, they get it working, and Andrew clicks through to the agenda slide he'd built a week earlier. First item: 9:00 to 9:15, technical difficulties. Everybody laughed, and then everybody relaxed. "We're not behind on anything. This is right where we're supposed to be." That's the magic trick: let people think one thing, and when they realize it was something else entirely, they know they're in good hands. In this episode, Andrew and Connor get into why he treats a flop as a persona failure and not a personal one, the ten-second question to ask before you design anything for your colleagues, and why making his Zoom setup more professional made people trust him less. If you want your next pitch or offsite to bring some real joy instead of corporate cringe, this episode's for you. Chapters 00:00:00 The mutant magician who infected IDEO's DNA 00:00:53 The BDSM approach to opening a magic show 00:08:22 Technical difficulties: the slide deck joke that built trust 00:11:04 Consider the context: the hack for creating wonder 00:14:39 Casting clients as investors 00:16:13 Snapping people out of Zoom multitasking 00:18:13 The psychology of deception 00:25:34 Adult-like wonder vs childlike wonder 00:30:26 Be creative by standing on the backs of giants 00:36:00 Being liked: the persona vs the person 00:40:41 Purpose is a byproduct, not something you find 00:43:19 From roller coasters to the Magic Patio 00:46:32 Shake up your routines and add randomness 00:49:24 Let's do some magicThe Hardest Part Isn't Getting Sh*t Done. It's Knowing When to Stop — Dream.org CEO Nisha AnandNisha Anand might be the only person alive who's thrown fake blood on the White House and worked alongside Jared Kushner, Newt Gingrich, the Koch network, and Kim Kardashian to build the coalition behind the First Step Act — the most substantial breakthrough in criminal justice in a generation, according to the New York Times. 53,000 people are home from federal prison because of that one bill. Near the end of this conversation, Connor asks her a simple question: after decades of this work, are you tired? "Yes, I'm very tired, Connor. I'm very tired. And I never experienced burnout before in my life." We recorded this a few months ago. Since then, Nisha has announced she's stepping down from her nearly seven-year tenure as CEO of Dream.org. What you're hearing is a leader thinking out loud, before the decision, about what fighting to the best of her ability looks like at 50, compared to when she was 21 and chained by the neck to six other activists in the center ring of a circus. Along the way, she walks Connor through how she actually gets things done: how she names what she won't trade before anyone else at the table speaks, when working with an opponent is strategy and when it's selling out, and the question she asks her own staff when a deal starts to feel like a betrayal — who are we doing this for? If you've ever wondered whether the work is worth what it's costing you, this one is for you. Chapters 00:00:00 Fake blood, arrests, and the woman who gets sh*t done 00:01:08 Growing up rebellious 00:06:05 Punk rock and straight-edge hardcore 00:08:54 The circus arrest 00:14:11 Myanmar prison and five years of hard labor 00:23:25 The elevator with Marjorie Taylor Greene 00:26:18 Finding common ground without selling out 00:28:32 The First Step Act — 53,000 people home from prison 00:39:18 Would young Nisha think you're a sellout? 00:55:58 Exhausted but optimistic — why she can't stop 00:59:50 The trap of working hard 01:14:41 Power, unlikely allies, and what comes nextflightcast:01M209613MWPGM2GRW1C2Y97CYWed, 09 Sep 2026 12:50:48 -0000Nisha Anand might be the only person alive who's thrown fake blood on the White House and worked alongside Jared Kushner, Newt Gingrich, the Koch network, and Kim Kardashian to build the coalition behind the First Step Act — the most substantial breakthrough in criminal justice in a generation, according to the New York Times.

53,000 people are home from federal prison because of that one bill.

Near the end of this conversation, Connor asks her a simple question: after decades of this work, are you tired?

"Yes, I'm very tired, Connor. I'm very tired. And I never experienced burnout before in my life."

We recorded this a few months ago. Since then, Nisha has announced she's stepping down from her nearly seven-year tenure as CEO of Dream.org. What you're hearing is a leader thinking out loud, before the decision, about what fighting to the best of her ability looks like at 50, compared to when she was 21 and chained by the neck to six other activists in the center ring of a circus.

Along the way, she walks Connor through how she actually gets things done: how she names what she won't trade before anyone else at the table speaks, when working with an opponent is strategy and when it's selling out, and the question she asks her own staff when a deal starts to feel like a betrayal — who are we doing this for?

If you've ever wondered whether the work is worth what it's costing you, this one is for you.


Chapters

  • 00:00:00 Fake blood, arrests, and the woman who gets sh*t done
  • 00:01:08 Growing up rebellious
  • 00:06:05 Punk rock and straight-edge hardcore
  • 00:08:54 The circus arrest
  • 00:14:11 Myanmar prison and five years of hard labor
  • 00:23:25 The elevator with Marjorie Taylor Greene
  • 00:26:18 Finding common ground without selling out
  • 00:28:32 The First Step Act — 53,000 people home from prison
  • 00:39:18 Would young Nisha think you're a sellout?
  • 00:55:58 Exhausted but optimistic — why she can't stop
  • 00:59:50 The trap of working hard
  • 01:14:41 Power, unlikely allies, and what comes next

]]>The Hardest Part Isn't Getting Sh*t Done. It's Knowing When to Stop — Dream.org CEO Nisha Anandfull4614falseNisha Anand might be the only person alive who's thrown fake blood on the White House and worked alongside Jared Kushner, Newt Gingrich, the Koch network, and Kim Kardashian to build the coalition behind the First Step Act — the most substantial breakthrough in criminal justice in a generation, according to the New York Times. 53,000 people are home from federal prison because of that one bill. Near the end of this conversation, Connor asks her a simple question: after decades of this work, are you tired? "Yes, I'm very tired, Connor. I'm very tired. And I never experienced burnout before in my life." We recorded this a few months ago. Since then, Nisha has announced she's stepping down from her nearly seven-year tenure as CEO of Dream.org. What you're hearing is a leader thinking out loud, before the decision, about what fighting to the best of her ability looks like at 50, compared to when she was 21 and chained by the neck to six other activists in the center ring of a circus. Along the way, she walks Connor through how she actually gets things done: how she names what she won't trade before anyone else at the table speaks, when working with an opponent is strategy and when it's selling out, and the question she asks her own staff when a deal starts to feel like a betrayal — who are we doing this for? If you've ever wondered whether the work is worth what it's costing you, this one is for you. Chapters 00:00:00 Fake blood, arrests, and the woman who gets sh*t done 00:01:08 Growing up rebellious 00:06:05 Punk rock and straight-edge hardcore 00:08:54 The circus arrest 00:14:11 Myanmar prison and five years of hard labor 00:23:25 The elevator with Marjorie Taylor Greene 00:26:18 Finding common ground without selling out 00:28:32 The First Step Act — 53,000 people home from prison 00:39:18 Would young Nisha think you're a sellout? 00:55:58 Exhausted but optimistic — why she can't stop 00:59:50 The trap of working hard 01:14:41 Power, unlikely allies, and what comes nextThe Secret to a 50-Year Career Is Being Willing to Lose It – Ohio Governor Mike DeWine"You have to be willing to fail." That's Mike DeWine, the man who's held just about every role in Ohio politics, including US Senator, a job he ran for four times. First, he lost. Then he won. Then he won again. And then he lost. After that second loss, DeWine came home to Ohio where everyone congratulated him on a great end to a great career. Well, almost everyone. His wife Fran, who he met in the first grade and has now been married to for fifty-nine years, said, "you're not done unless you tell yourself you’re done." DeWine wasn't done. Next, he ran for Attorney General of Ohio and won. Then, he became Ohio's Governor, a role he finishes this coming January. So Connor sat him down for an exit interview on topics including: whether the American Dream can survive the AI revolution why the worst thing a leader can be is the smartest person in the room DeWine's thirty-year history of humanitarian work in Haiti his secret to remaining stubbornly optimistic (hint: have eight kids) Plus: the box of chocolates in sixth grade and the line his whole career comes down to: "Work is the price we pay to achieve what we want. No shortcuts." If you're looking for hope from someone who's been in the trenches for the past fifty years driving actual change, this episode is for you. CHAPTERS: Chapters 00:00 The career nobody wins by accident 00:06:53 Learning to lose — The 2006 Senate defeat 00:10:03 Never be the smartest person in the room 00:13:31 59 years — The partnership that started in first grade 00:21:41 Is the American Dream dead? 00:26:55 AI, critical thinking, and muddling through disruption 00:31:48 30 years in Haiti — Why he keeps going back 00:36:47 Springfield and the eating dogs rumor 00:38:30 What's next — Leaving the governor's mansion 00:41:03 Work is the price we pay — Advice for the next generationflightcast:01M0X2PW7VGNEXNBZJNPTGXDKWWed, 26 Aug 2026 16:58:27 -0000"You have to be willing to fail." That's Mike DeWine, the man who's held just about every role in Ohio politics, including US Senator, a job he ran for four times.

First, he lost. Then he won. Then he won again. And then he lost.

After that second loss, DeWine came home to Ohio where everyone congratulated him on a great end to a great career. Well, almost everyone.

His wife Fran, who he met in the first grade and has now been married to for fifty-nine years, said, "you're not done unless you tell yourself you’re done."

DeWine wasn't done.

Next, he ran for Attorney General of Ohio and won.

Then, he became Ohio's Governor, a role he finishes this coming January. So Connor sat him down for an exit interview on topics including:

  • whether the American Dream can survive the AI revolution
  • why the worst thing a leader can be is the smartest person in the room
  • DeWine's thirty-year history of humanitarian work in Haiti
  • his secret to remaining stubbornly optimistic (hint: have eight kids)

Plus: the box of chocolates in sixth grade and the line his whole career comes down to:

"Work is the price we pay to achieve what we want. No shortcuts."

If you're looking for hope from someone who's been in the trenches for the past fifty years driving actual change, this episode is for you.

CHAPTERS:

Chapters

  • 00:00 The career nobody wins by accident
  • 00:06:53 Learning to lose — The 2006 Senate defeat
  • 00:10:03 Never be the smartest person in the room
  • 00:13:31 59 years — The partnership that started in first grade
  • 00:21:41 Is the American Dream dead?
  • 00:26:55 AI, critical thinking, and muddling through disruption
  • 00:31:48 30 years in Haiti — Why he keeps going back
  • 00:36:47 Springfield and the eating dogs rumor
  • 00:38:30 What's next — Leaving the governor's mansion
  • 00:41:03 Work is the price we pay — Advice for the next generation

]]>The Secret to a 50-Year Career Is Being Willing to Lose It – Ohio Governor Mike DeWinefull2816false"You have to be willing to fail." That's Mike DeWine, the man who's held just about every role in Ohio politics, including US Senator, a job he ran for four times. First, he lost. Then he won. Then he won again. And then he lost. After that second loss, DeWine came home to Ohio where everyone congratulated him on a great end to a great career. Well, almost everyone. His wife Fran, who he met in the first grade and has now been married to for fifty-nine years, said, "you're not done unless you tell yourself you’re done." DeWine wasn't done. Next, he ran for Attorney General of Ohio and won. Then, he became Ohio's Governor, a role he finishes this coming January. So Connor sat him down for an exit interview on topics including: whether the American Dream can survive the AI revolution why the worst thing a leader can be is the smartest person in the room DeWine's thirty-year history of humanitarian work in Haiti his secret to remaining stubbornly optimistic (hint: have eight kids) Plus: the box of chocolates in sixth grade and the line his whole career comes down to: "Work is the price we pay to achieve what we want. No shortcuts." If you're looking for hope from someone who's been in the trenches for the past fifty years driving actual change, this episode is for you. CHAPTERS: Chapters 00:00 The career nobody wins by accident 00:06:53 Learning to lose — The 2006 Senate defeat 00:10:03 Never be the smartest person in the room 00:13:31 59 years — The partnership that started in first grade 00:21:41 Is the American Dream dead? 00:26:55 AI, critical thinking, and muddling through disruption 00:31:48 30 years in Haiti — Why he keeps going back 00:36:47 Springfield and the eating dogs rumor 00:38:30 What's next — Leaving the governor's mansion 00:41:03 Work is the price we pay — Advice for the next generationRunning Sesame Street Is Harder Than Working in the White House: Sesame Workshop CEO, Sherrie WestinEveryone loves Sesame Street. Now imagine being in charge of it. That's Sherrie Westin's job. As CEO and President of Sesame Workshop, Westin's day-to-day includes: figuring out how to explain to a four-year-old that a parent is in prison. Deciding whether Elmo wears a mask during the pandemic, knowing half the country will be furious either way. Spending three years with every autism organization in America building a single Muppet. Doing layoffs in the hardest year the place has ever had. And answering the question she can't get away from: how do you stay true to your values and remain a beacon without becoming a lightning rod? She ran a television network before this. She worked in the White House. She says this one is harder than both. "People are like, how hard could it be? You're hanging out with Muppets. Yeah, right." What nobody tells you about Sesame Street is that it's a research operation. They tried a storyline about divorce, tested it, found it was scaring kids, and killed it. When they built Julia, the first autistic Muppet, they got every autism organization in one room, groups that disagreed with each other on almost everything, and found the one thing they all agreed on. A mother wrote in afterward. She'd never been able to find the words to tell her five-year-old she had autism, until her daughter saw the Muppet Julia on Sesame Street. Her daughter's reaction: "So I'm amazing too, right?" Plus: Big Bird's actual age, why she hires for a sense of humor, and what a lot of adults could stand to learn from a show made for three-year-olds. CHAPTERS Chapters 00:00:00 Managing Big Bird is harder than running the White House 00:01:44 The hidden complexity of Sesame Street 00:06:21 Reaching 500 million children — The scope of Sesame's mission 00:10:26 Creating Julia, the first autistic Muppet 00:14:22 "So I'm amazing too, right?" 00:17:28 Staying nonpartisan when everything is political 00:23:06 Big Bird is six years old 00:27:01 The hardest part: downsizing and losing USAID funding 00:30:40 Screen time guiltflightcast:01KZPHYJ70M9BPAQN1RHF9TJSGWed, 12 Aug 2026 09:40:14 -0000Everyone loves Sesame Street. Now imagine being in charge of it.

That's Sherrie Westin's job. As CEO and President of Sesame Workshop, Westin's day-to-day includes: figuring out how to explain to a four-year-old that a parent is in prison. Deciding whether Elmo wears a mask during the pandemic, knowing half the country will be furious either way. Spending three years with every autism organization in America building a single Muppet. Doing layoffs in the hardest year the place has ever had. And answering the question she can't get away from: how do you stay true to your values and remain a beacon without becoming a lightning rod?

She ran a television network before this. She worked in the White House. She says this one is harder than both. "People are like, how hard could it be? You're hanging out with Muppets. Yeah, right."

What nobody tells you about Sesame Street is that it's a research operation. They tried a storyline about divorce, tested it, found it was scaring kids, and killed it. When they built Julia, the first autistic Muppet, they got every autism organization in one room, groups that disagreed with each other on almost everything, and found the one thing they all agreed on. A mother wrote in afterward. She'd never been able to find the words to tell her five-year-old she had autism, until her daughter saw the Muppet Julia on Sesame Street. Her daughter's reaction:

"So I'm amazing too, right?"

Plus: Big Bird's actual age, why she hires for a sense of humor, and what a lot of adults could stand to learn from a show made for three-year-olds.

CHAPTERS

Chapters

  • 00:00:00 Managing Big Bird is harder than running the White House
  • 00:01:44 The hidden complexity of Sesame Street
  • 00:06:21 Reaching 500 million children — The scope of Sesame's mission
  • 00:10:26 Creating Julia, the first autistic Muppet
  • 00:14:22 "So I'm amazing too, right?"
  • 00:17:28 Staying nonpartisan when everything is political
  • 00:23:06 Big Bird is six years old
  • 00:27:01 The hardest part: downsizing and losing USAID funding
  • 00:30:40 Screen time guilt

]]>Running Sesame Street Is Harder Than Working in the White House: Sesame Workshop CEO, Sherrie Westinfull2029falseEveryone loves Sesame Street. Now imagine being in charge of it. That's Sherrie Westin's job. As CEO and President of Sesame Workshop, Westin's day-to-day includes: figuring out how to explain to a four-year-old that a parent is in prison. Deciding whether Elmo wears a mask during the pandemic, knowing half the country will be furious either way. Spending three years with every autism organization in America building a single Muppet. Doing layoffs in the hardest year the place has ever had. And answering the question she can't get away from: how do you stay true to your values and remain a beacon without becoming a lightning rod? She ran a television network before this. She worked in the White House. She says this one is harder than both. "People are like, how hard could it be? You're hanging out with Muppets. Yeah, right." What nobody tells you about Sesame Street is that it's a research operation. They tried a storyline about divorce, tested it, found it was scaring kids, and killed it. When they built Julia, the first autistic Muppet, they got every autism organization in one room, groups that disagreed with each other on almost everything, and found the one thing they all agreed on. A mother wrote in afterward. She'd never been able to find the words to tell her five-year-old she had autism, until her daughter saw the Muppet Julia on Sesame Street. Her daughter's reaction: "So I'm amazing too, right?" Plus: Big Bird's actual age, why she hires for a sense of humor, and what a lot of adults could stand to learn from a show made for three-year-olds. CHAPTERS Chapters 00:00:00 Managing Big Bird is harder than running the White House 00:01:44 The hidden complexity of Sesame Street 00:06:21 Reaching 500 million children — The scope of Sesame's mission 00:10:26 Creating Julia, the first autistic Muppet 00:14:22 "So I'm amazing too, right?" 00:17:28 Staying nonpartisan when everything is political 00:23:06 Big Bird is six years old 00:27:01 The hardest part: downsizing and losing USAID funding 00:30:40 Screen time guiltNo One Knows Katie Couric Like ThisYou think you’ve known Katie Couric your whole life. You have no idea. Yes, the press called her America's Sweetheart. They also called her a diva, an ice queen, and a bitch on wheels (Connor's favorite). The real story starts there: how does a journalist turned national icon become herself without losing the magic that got her there in the first place?   Connor and Katie’s conversation went everywhere: fame and what it does to your head, loss and what actually lasts, getting older, the Sarah Palin interview she still feels "secondhand cringe" about, pickleball, breast milk, how she got completely fooled by AI, and her glorious give-no-fucks era. Katie fills out a report card for Connor at the end too. You'll want to stay for that. CHAPTERS Chapters 00:00:00 How fame f*cks with your head 00:02:51 What most interviewers mess up 00:06:27 The power of boredom and the hippocampus 00:08:05 Addicted to the grind 00:12:18 Going independent before the creator economy existed 00:15:42 The perky problem and clapbacks on Threads 00:18:09 Fighting to be taken seriously 00:27:17 Sarah Palin and the interview heard around the world 00:33:20 AI, income inequality, and the Jevons paradox 00:37:59 Your colon saved a lot of lives 00:41:40 Faith, God, and being a secular humanist 00:45:12 We're all terminal, how do you want to spend your time? 00:47:55 Nothing matters but your friends and your family 00:49:38 The Katie Couric report cardflightcast:01KYPNYPCBQ9J004PVPNZWMQMGWed, 29 Jul 2026 15:15:13 -0000You think you’ve known Katie Couric your whole life. You have no idea.

Yes, the press called her America's Sweetheart. They also called her a diva, an ice queen, and a bitch on wheels (Connor's favorite). The real story starts there: how does a journalist turned national icon become herself without losing the magic that got her there in the first place?  

Connor and Katie’s conversation went everywhere: fame and what it does to your head, loss and what actually lasts, getting older, the Sarah Palin interview she still feels "secondhand cringe" about, pickleball, breast milk, how she got completely fooled by AI, and her glorious give-no-fucks era. Katie fills out a report card for Connor at the end too. You'll want to stay for that.

CHAPTERS

Chapters

  • 00:00:00 How fame f*cks with your head
  • 00:02:51 What most interviewers mess up
  • 00:06:27 The power of boredom and the hippocampus
  • 00:08:05 Addicted to the grind
  • 00:12:18 Going independent before the creator economy existed
  • 00:15:42 The perky problem and clapbacks on Threads
  • 00:18:09 Fighting to be taken seriously
  • 00:27:17 Sarah Palin and the interview heard around the world
  • 00:33:20 AI, income inequality, and the Jevons paradox
  • 00:37:59 Your colon saved a lot of lives
  • 00:41:40 Faith, God, and being a secular humanist
  • 00:45:12 We're all terminal, how do you want to spend your time?
  • 00:47:55 Nothing matters but your friends and your family
  • 00:49:38 The Katie Couric report card

]]>No One Knows Katie Couric Like Thisfull3096falseYou think you’ve known Katie Couric your whole life. You have no idea. Yes, the press called her America's Sweetheart. They also called her a diva, an ice queen, and a bitch on wheels (Connor's favorite). The real story starts there: how does a journalist turned national icon become herself without losing the magic that got her there in the first place?   Connor and Katie’s conversation went everywhere: fame and what it does to your head, loss and what actually lasts, getting older, the Sarah Palin interview she still feels "secondhand cringe" about, pickleball, breast milk, how she got completely fooled by AI, and her glorious give-no-fucks era. Katie fills out a report card for Connor at the end too. You'll want to stay for that. CHAPTERS Chapters 00:00:00 How fame f*cks with your head 00:02:51 What most interviewers mess up 00:06:27 The power of boredom and the hippocampus 00:08:05 Addicted to the grind 00:12:18 Going independent before the creator economy existed 00:15:42 The perky problem and clapbacks on Threads 00:18:09 Fighting to be taken seriously 00:27:17 Sarah Palin and the interview heard around the world 00:33:20 AI, income inequality, and the Jevons paradox 00:37:59 Your colon saved a lot of lives 00:41:40 Faith, God, and being a secular humanist 00:45:12 We're all terminal, how do you want to spend your time? 00:47:55 Nothing matters but your friends and your family 00:49:38 The Katie Couric report cardHow to Make Yourself AI-Proof, According to One of the World's Top VCs - Ann Miura-KoWhen the VC Forbes once called “the most powerful woman in startups” says there's a way to make yourself AI-proof, it's worth listening. Ann Miura-Ko spent the last two decades deciding which founders are worth betting on. She wrote the first check into TaskRabbit, got in early on Lyft, and teaches entrepreneurship at Stanford. There are few people closer to what's actually happening in AI, and her read is a hopeful one: AI is coming for the order takers, but anyone can become an order maker. The order takers, the people whose job is to run down a list and check the boxes, should be nervous. But everyone is opinionated about something — the thing they insist gets done a certain way. Ann's argument is that this is now the whole job: point your expertise at an infinite number of software agents and let them handle the rest. Connor and Ann get into why you can't train AI to have soul, the difference between what AI lets you do and what you should choose *not* to do, and the "Ann brain" she's built so the technology works for her without her ever handing over the keys. The conversation is also, fittingly, a deeply human one: her childhood theory of what it means to be rich, and what it feels like to watch your kids leave home, one by one. CHAPTERS Chapters 00:00:00 Intro — Training AI to have soul 00:01:29 Sneaking into negotiations class 00:04:23 Is that a world-class effort? — Lessons from a rocket scientist dad 00:06:39 The PhD moment — Realizing you're not the best 00:07:58 Designing your life around self-expression 00:09:23 Starting Floodgate — Pregnant, PhD-ing, and investing 00:10:54 From young whippersnapper to wise boomer 00:12:25 Measuring success beyond work metrics 00:18:42 The pink and blue sweater — What it means to be rich 00:21:36 Develop the muscle for giving 00:22:46 Being asked to be a co-conspirator 00:25:05 Why are you in such a hurry? — The Stanford dropout trap 00:27:16 Building a personal AI brain 00:30:43 What's mine, what's yours? — The future of AI and IP 00:32:25 The five levels of AI adoption 00:33:16 You can't train AI to have soul 00:44:18 Order makers vs order takers 00:46:45 Religion, service, and who you're accountable to 00:53:15 Freedom from constraint — Marriage, religion, and the good life 00:54:27 Turning 50 — Shedding and what comes nextflightcast:01KX0MBW5W8PY76C2VFF6KF09SWed, 08 Jul 2026 12:16:10 -0000When the VC Forbes once called “the most powerful woman in startups” says there's a way to make yourself AI-proof, it's worth listening.

Ann Miura-Ko spent the last two decades deciding which founders are worth betting on. She wrote the first check into TaskRabbit, got in early on Lyft, and teaches entrepreneurship at Stanford.

There are few people closer to what's actually happening in AI, and her read is a hopeful one: AI is coming for the order takers, but anyone can become an order maker.

The order takers, the people whose job is to run down a list and check the boxes, should be nervous. But everyone is opinionated about something — the thing they insist gets done a certain way. Ann's argument is that this is now the whole job: point your expertise at an infinite number of software agents and let them handle the rest.

Connor and Ann get into why you can't train AI to have soul, the difference between what AI lets you do and what you should choose *not* to do, and the "Ann brain" she's built so the technology works for her without her ever handing over the keys.

The conversation is also, fittingly, a deeply human one: her childhood theory of what it means to be rich, and what it feels like to watch your kids leave home, one by one.

CHAPTERS

Chapters

  • 00:00:00 Intro — Training AI to have soul
  • 00:01:29 Sneaking into negotiations class
  • 00:04:23 Is that a world-class effort? — Lessons from a rocket scientist dad
  • 00:06:39 The PhD moment — Realizing you're not the best
  • 00:07:58 Designing your life around self-expression
  • 00:09:23 Starting Floodgate — Pregnant, PhD-ing, and investing
  • 00:10:54 From young whippersnapper to wise boomer
  • 00:12:25 Measuring success beyond work metrics
  • 00:18:42 The pink and blue sweater — What it means to be rich
  • 00:21:36 Develop the muscle for giving
  • 00:22:46 Being asked to be a co-conspirator
  • 00:25:05 Why are you in such a hurry? — The Stanford dropout trap
  • 00:27:16 Building a personal AI brain
  • 00:30:43 What's mine, what's yours? — The future of AI and IP
  • 00:32:25 The five levels of AI adoption
  • 00:33:16 You can't train AI to have soul
  • 00:44:18 Order makers vs order takers
  • 00:46:45 Religion, service, and who you're accountable to
  • 00:53:15 Freedom from constraint — Marriage, religion, and the good life
  • 00:54:27 Turning 50 — Shedding and what comes next

]]>How to Make Yourself AI-Proof, According to One of the World's Top VCs - Ann Miura-Kofull3452falseWhen the VC Forbes once called “the most powerful woman in startups” says there's a way to make yourself AI-proof, it's worth listening. Ann Miura-Ko spent the last two decades deciding which founders are worth betting on. She wrote the first check into TaskRabbit, got in early on Lyft, and teaches entrepreneurship at Stanford. There are few people closer to what's actually happening in AI, and her read is a hopeful one: AI is coming for the order takers, but anyone can become an order maker. The order takers, the people whose job is to run down a list and check the boxes, should be nervous. But everyone is opinionated about something — the thing they insist gets done a certain way. Ann's argument is that this is now the whole job: point your expertise at an infinite number of software agents and let them handle the rest. Connor and Ann get into why you can't train AI to have soul, the difference between what AI lets you do and what you should choose *not* to do, and the "Ann brain" she's built so the technology works for her without her ever handing over the keys. The conversation is also, fittingly, a deeply human one: her childhood theory of what it means to be rich, and what it feels like to watch your kids leave home, one by one. CHAPTERS Chapters 00:00:00 Intro — Training AI to have soul 00:01:29 Sneaking into negotiations class 00:04:23 Is that a world-class effort? — Lessons from a rocket scientist dad 00:06:39 The PhD moment — Realizing you're not the best 00:07:58 Designing your life around self-expression 00:09:23 Starting Floodgate — Pregnant, PhD-ing, and investing 00:10:54 From young whippersnapper to wise boomer 00:12:25 Measuring success beyond work metrics 00:18:42 The pink and blue sweater — What it means to be rich 00:21:36 Develop the muscle for giving 00:22:46 Being asked to be a co-conspirator 00:25:05 Why are you in such a hurry? — The Stanford dropout trap 00:27:16 Building a personal AI brain 00:30:43 What's mine, what's yours? — The future of AI and IP 00:32:25 The five levels of AI adoption 00:33:16 You can't train AI to have soul 00:44:18 Order makers vs order takers 00:46:45 Religion, service, and who you're accountable to 00:53:15 Freedom from constraint — Marriage, religion, and the good life 00:54:27 Turning 50 — Shedding and what comes nextHow to Actually Change Your Behavior (No, It's Not Willpower) — Behavioral Scientist Kristen BermanKristen Berman is one of the world's foremost experts on getting people to do what they say they want to do. She also routinely has a hard time following her own advice, which is precisely why she got into the field. Berman was on the founding team for behavioral economics at Google — a practice that now spans 26 teams across the company — and she founded Irrational Labs, a behavioral product design company that helps companies like LinkedIn, Airbnb, and PayPal increase the health, wealth, and happiness of their users. Her work keeps landing on the same uncomfortable truth: the things that actually run your behavior are your environment and your incentives, and you barely notice either one. She learned the incentive half the hard way, when a project quietly turned her into what she calls a predatory lender.  In this episode, she and Connor get practical: Why buying a dog beats relying on willpower. How a “Ulysses contract” binds your future self. Why she built her life around a 20-person Oakland commune called Radish, where everyone eats dinner together at 7:30.  If you've ever known better and done it anyway, or wanted to know how to design an environment that brings out the best in your team, this one’s for you. CHAPTERS Chapters 00:00:00 The chocolate croissant you didn't mean to eat 00:00:55 Why behavioral science lights her up 00:02:16 How choice architecture works 00:05:31 You're always being manipulated by your environment 00:07:08 When good intentions meet bad incentives 00:08:39 The stand-up challenge — Closing the intention-action gap 00:09:53 Buy a dog — The power of one-time decisions 00:15:33 Commitment contracts that actually work 00:17:13 Taking away the joy of work — What leaders get wrong 00:19:51 Small teams, big autonomy — The Irrational Labs approach 00:21:35 Extrinsic vs intrinsic motivation — What actually works 00:26:26 Does confetti actually work? 00:27:30 Work harder — The contrarian take on workplace culture 00:29:04 Difficulty as fuel — The hero's journey at work 00:31:18 Social desirability — Why we're all a little vain 00:32:56 You've never arrived — The learning mindset 00:34:02 Living in a commune — Behavioral science in the wild 00:35:02 Behavioral contagion and seeing your partner perform 00:36:57 Relationships drive happiness — Make them easier 00:37:55 Low willpower, high design — How Kristen lives 00:39:40 The billboard — Compliment someoneflightcast:01KVR6TP0JGD6TE6R91BB4749AWed, 24 Jun 2026 09:55:00 -0000Kristen Berman is one of the world's foremost experts on getting people to do what they say they want to do. She also routinely has a hard time following her own advice, which is precisely why she got into the field.

Berman was on the founding team for behavioral economics at Google — a practice that now spans 26 teams across the company — and she founded Irrational Labs, a behavioral product design company that helps companies like LinkedIn, Airbnb, and PayPal increase the health, wealth, and happiness of their users.

Her work keeps landing on the same uncomfortable truth: the things that actually run your behavior are your environment and your incentives, and you barely notice either one. She learned the incentive half the hard way, when a project quietly turned her into what she calls a predatory lender. 

In this episode, she and Connor get practical: Why buying a dog beats relying on willpower. How a “Ulysses contract” binds your future self. Why she built her life around a 20-person Oakland commune called Radish, where everyone eats dinner together at 7:30. 

If you've ever known better and done it anyway, or wanted to know how to design an environment that brings out the best in your team, this one’s for you.

CHAPTERS

Chapters

  • 00:00:00 The chocolate croissant you didn't mean to eat
  • 00:00:55 Why behavioral science lights her up
  • 00:02:16 How choice architecture works
  • 00:05:31 You're always being manipulated by your environment
  • 00:07:08 When good intentions meet bad incentives
  • 00:08:39 The stand-up challenge — Closing the intention-action gap
  • 00:09:53 Buy a dog — The power of one-time decisions
  • 00:15:33 Commitment contracts that actually work
  • 00:17:13 Taking away the joy of work — What leaders get wrong
  • 00:19:51 Small teams, big autonomy — The Irrational Labs approach
  • 00:21:35 Extrinsic vs intrinsic motivation — What actually works
  • 00:26:26 Does confetti actually work?
  • 00:27:30 Work harder — The contrarian take on workplace culture
  • 00:29:04 Difficulty as fuel — The hero's journey at work
  • 00:31:18 Social desirability — Why we're all a little vain
  • 00:32:56 You've never arrived — The learning mindset
  • 00:34:02 Living in a commune — Behavioral science in the wild
  • 00:35:02 Behavioral contagion and seeing your partner perform
  • 00:36:57 Relationships drive happiness — Make them easier
  • 00:37:55 Low willpower, high design — How Kristen lives
  • 00:39:40 The billboard — Compliment someone

]]>How to Actually Change Your Behavior (No, It's Not Willpower) — Behavioral Scientist Kristen Bermanfull2496falseKristen Berman is one of the world's foremost experts on getting people to do what they say they want to do. She also routinely has a hard time following her own advice, which is precisely why she got into the field. Berman was on the founding team for behavioral economics at Google — a practice that now spans 26 teams across the company — and she founded Irrational Labs, a behavioral product design company that helps companies like LinkedIn, Airbnb, and PayPal increase the health, wealth, and happiness of their users. Her work keeps landing on the same uncomfortable truth: the things that actually run your behavior are your environment and your incentives, and you barely notice either one. She learned the incentive half the hard way, when a project quietly turned her into what she calls a predatory lender.  In this episode, she and Connor get practical: Why buying a dog beats relying on willpower. How a “Ulysses contract” binds your future self. Why she built her life around a 20-person Oakland commune called Radish, where everyone eats dinner together at 7:30.  If you've ever known better and done it anyway, or wanted to know how to design an environment that brings out the best in your team, this one’s for you. CHAPTERS Chapters 00:00:00 The chocolate croissant you didn't mean to eat 00:00:55 Why behavioral science lights her up 00:02:16 How choice architecture works 00:05:31 You're always being manipulated by your environment 00:07:08 When good intentions meet bad incentives 00:08:39 The stand-up challenge — Closing the intention-action gap 00:09:53 Buy a dog — The power of one-time decisions 00:15:33 Commitment contracts that actually work 00:17:13 Taking away the joy of work — What leaders get wrong 00:19:51 Small teams, big autonomy — The Irrational Labs approach 00:21:35 Extrinsic vs intrinsic motivation — What actually works 00:26:26 Does confetti actually work? 00:27:30 Work harder — The contrarian take on workplace culture 00:29:04 Difficulty as fuel — The hero's journey at work 00:31:18 Social desirability — Why we're all a little vain 00:32:56 You've never arrived — The learning mindset 00:34:02 Living in a commune — Behavioral science in the wild 00:35:02 Behavioral contagion and seeing your partner perform 00:36:57 Relationships drive happiness — Make them easier 00:37:55 Low willpower, high design — How Kristen lives 00:39:40 The billboard — Compliment someoneWhy Real Leadership Feels Like Crap — Farmgirl Flowers Founder Christina StembelChristina Stembel started Farmgirl Flowers in 2010 with $49,000 in her bank account, no college degree, and no VC funding. Sixteen years later, it’s a $35-million-a-year company. "We joke at Farmgirl that we're like cockroaches. You can't get rid of us. You just get stomped on, you just keep going." In this conversation, Christina and Connor talk about: the costs of building a company without the credentials the 28-hour test that saved the company during the pandemic why leaders can't always stick to their values why real leadership means feeling like crap most of the time If you're sick of leadership platitudes and hungry for the story of someone doing the hard work, against the odds, this conversation is for you.flightcast:01KSMA5CBPTHK5CDBRQGTK0QC7Wed, 27 May 2026 17:51:00 -0000Christina Stembel started Farmgirl Flowers in 2010 with $49,000 in her bank account, no college degree, and no VC funding. Sixteen years later, it’s a $35-million-a-year company.

"We joke at Farmgirl that we're like cockroaches. You can't get rid of us. You just get stomped on, you just keep going."

In this conversation, Christina and Connor talk about:

  • the costs of building a company without the credentials
  • the 28-hour test that saved the company during the pandemic
  • why leaders can't always stick to their values
  • why real leadership means feeling like crap most of the time

If you're sick of leadership platitudes and hungry for the story of someone doing the hard work, against the odds, this conversation is for you.

]]>Why Real Leadership Feels Like Crap — Farmgirl Flowers Founder Christina Stembelfull2988falseChristina Stembel started Farmgirl Flowers in 2010 with $49,000 in her bank account, no college degree, and no VC funding. Sixteen years later, it’s a $35-million-a-year company. "We joke at Farmgirl that we're like cockroaches. You can't get rid of us. You just get stomped on, you just keep going." In this conversation, Christina and Connor talk about: the costs of building a company without the credentials the 28-hour test that saved the company during the pandemic why leaders can't always stick to their values why real leadership means feeling like crap most of the time If you're sick of leadership platitudes and hungry for the story of someone doing the hard work, against the odds, this conversation is for you.Don’t Follow Your Passion — Do This Instead | Crankstart Foundation's CEO Missy NarulaMost people in philanthropy wouldn't call themselves a "safety-net capitalist." Most people aren't Missy Narula. Missy’s made a career being comfortable in contradictions like “following your passion is overrated”—and she’s got the resume to prove it.  After Yale, Boston Consulting Group, and TPG, Missy walked away from all of it to start a company making phone holders that kept babies entertained during diaper changes. She got a patent. The company failed. She'll tell you those were the best years of her career.  Now she's CEO of Crankstart Foundation. Crankstart's work is mostly about San Francisco: affordable housing, healthcare career ladders, the kind of cross-sector partnerships Missy says the philanthropy field doesn't do enough of. One recent project put $10 million into a 168-unit affordable housing building. Another is a UCSF partnership that builds a career ladder from medical assistant to radiologist. On this episode of Is This Working?!, she tells Connor about the eight years she spent at blue-chip firms specifically to earn herself the option to fail later. About what it took to look herself in the mirror and admit she wasn't good at being an entrepreneur. About why the best career advice she has for a 22-year-old is take a hard job, learn something hard, and trust you'll find what calls your heart later. And then she tells him about her mom, who died when Missy was 19 and her mom was 46. "I thought she had lived a lot," Missy says. "But now that I'm 44, I realize she was just getting started." CHAPTERS Chapters 00:00:00 Being okay with being wrong 00:00:57 McDonald's University and the hardest job ever 00:01:54 Parental expectations and the privilege of freedom 00:03:18 The competitive child 00:04:29 Performance through play — High achievement without pressure 00:07:19 The credibility sprint — Building a bank of signals 00:09:09 Don't follow your passion — Do this instead 00:14:55 The failed entrepreneur who never had more fun 00:21:01 Parenthood as a superpower in the workplace 00:24:30 From bloodthirsty capitalist to foundation leader 00:30:52 Working with Michael Moritz — Excellence teaches excellence 00:34:18 Making philanthropy less transactional 00:42:22 The trust battery and rising tides lift all boats 00:43:54 San Francisco needs grace, patience, and capital 00:45:29 Losing her mom at 19 — Nobody's entitled to tomorrowflightcast:01KRGDWPQ7FC92GV05276A67T0Wed, 13 May 2026 13:57:00 -0000Most people in philanthropy wouldn't call themselves a "safety-net capitalist." Most people aren't Missy Narula.

Missy’s made a career being comfortable in contradictions like “following your passion is overrated”—and she’s got the resume to prove it. 

After Yale, Boston Consulting Group, and TPG, Missy walked away from all of it to start a company making phone holders that kept babies entertained during diaper changes. She got a patent. The company failed. She'll tell you those were the best years of her career. 

Now she's CEO of Crankstart Foundation. Crankstart's work is mostly about San Francisco: affordable housing, healthcare career ladders, the kind of cross-sector partnerships Missy says the philanthropy field doesn't do enough of. One recent project put $10 million into a 168-unit affordable housing building. Another is a UCSF partnership that builds a career ladder from medical assistant to radiologist.

On this episode of Is This Working?!, she tells Connor about the eight years she spent at blue-chip firms specifically to earn herself the option to fail later. About what it took to look herself in the mirror and admit she wasn't good at being an entrepreneur. About why the best career advice she has for a 22-year-old is take a hard job, learn something hard, and trust you'll find what calls your heart later.

And then she tells him about her mom, who died when Missy was 19 and her mom was 46. "I thought she had lived a lot," Missy says. "But now that I'm 44, I realize she was just getting started."

CHAPTERS

Chapters

  • 00:00:00 Being okay with being wrong
  • 00:00:57 McDonald's University and the hardest job ever
  • 00:01:54 Parental expectations and the privilege of freedom
  • 00:03:18 The competitive child
  • 00:04:29 Performance through play — High achievement without pressure
  • 00:07:19 The credibility sprint — Building a bank of signals
  • 00:09:09 Don't follow your passion — Do this instead
  • 00:14:55 The failed entrepreneur who never had more fun
  • 00:21:01 Parenthood as a superpower in the workplace
  • 00:24:30 From bloodthirsty capitalist to foundation leader
  • 00:30:52 Working with Michael Moritz — Excellence teaches excellence
  • 00:34:18 Making philanthropy less transactional
  • 00:42:22 The trust battery and rising tides lift all boats
  • 00:43:54 San Francisco needs grace, patience, and capital
  • 00:45:29 Losing her mom at 19 — Nobody's entitled to tomorrow

]]>Don’t Follow Your Passion — Do This Instead | Crankstart Foundation's CEO Missy Narulafull2959falseMost people in philanthropy wouldn't call themselves a "safety-net capitalist." Most people aren't Missy Narula. Missy’s made a career being comfortable in contradictions like “following your passion is overrated”—and she’s got the resume to prove it.  After Yale, Boston Consulting Group, and TPG, Missy walked away from all of it to start a company making phone holders that kept babies entertained during diaper changes. She got a patent. The company failed. She'll tell you those were the best years of her career.  Now she's CEO of Crankstart Foundation. Crankstart's work is mostly about San Francisco: affordable housing, healthcare career ladders, the kind of cross-sector partnerships Missy says the philanthropy field doesn't do enough of. One recent project put $10 million into a 168-unit affordable housing building. Another is a UCSF partnership that builds a career ladder from medical assistant to radiologist. On this episode of Is This Working?!, she tells Connor about the eight years she spent at blue-chip firms specifically to earn herself the option to fail later. About what it took to look herself in the mirror and admit she wasn't good at being an entrepreneur. About why the best career advice she has for a 22-year-old is take a hard job, learn something hard, and trust you'll find what calls your heart later. And then she tells him about her mom, who died when Missy was 19 and her mom was 46. "I thought she had lived a lot," Missy says. "But now that I'm 44, I realize she was just getting started." CHAPTERS Chapters 00:00:00 Being okay with being wrong 00:00:57 McDonald's University and the hardest job ever 00:01:54 Parental expectations and the privilege of freedom 00:03:18 The competitive child 00:04:29 Performance through play — High achievement without pressure 00:07:19 The credibility sprint — Building a bank of signals 00:09:09 Don't follow your passion — Do this instead 00:14:55 The failed entrepreneur who never had more fun 00:21:01 Parenthood as a superpower in the workplace 00:24:30 From bloodthirsty capitalist to foundation leader 00:30:52 Working with Michael Moritz — Excellence teaches excellence 00:34:18 Making philanthropy less transactional 00:42:22 The trust battery and rising tides lift all boats 00:43:54 San Francisco needs grace, patience, and capital 00:45:29 Losing her mom at 19 — Nobody's entitled to tomorrowWinning AI *Without* Losing The American Dream — Fmr US Commerce Secretary Gina RaimondoAI is here. The layoffs have started. Does anyone have a plan? Gina Raimondo does. Two-term Governor of Rhode Island, former U.S. Commerce Secretary, the person who shepherded the CHIPS Act through Congress and personally negotiated chip exports with Chinese leadership. Harvard, Oxford, Yale Law before any of it. Her plan: a new grand bargain between government and business. Workforce training that's continuous, employer-led, and funded by outcomes. Wage insurance for workers retraining mid-career. Tax incentives that make it more expensive to abandon workers than to retrain them. The same urgency we've poured into chips and models, applied to the tens of millions of American jobs about to change. In this episode, Connor and Gina get into the plan, the warning ("do this wrong and we will have automated our decline"), why UBI is a cop-out, and her honest reply to whether she'd like the job of President in 2028. There's also a phrase she banned in her own cabinet that we can't in good conscience print here. Connor gets her to use it on camera. Stay for that. Chapters 00:00:00 Intro — The woman betting on America's AI future 00:01:16 Finding your Andy — Love, partnership, and non-negotiables 00:05:46 Faith, spirituality, and the work arena 00:08:01 The AI crisis nobody's preparing for 00:10:33 Winning AI without losing America 00:14:34 The grand bargain — Changing incentives for companies 00:17:55 More women in charge would help 00:20:16 The girl in the back seat with the racing stripe 00:22:39 Lightning round — Biden, bathrooms, and power perks 00:30:11 Grin-fucking and the yes-man problem 00:37:32 Presidential ambitions and the right moment 00:41:48 Conquering the self and the Msgina Special 00:48:03 Legacy, love, and what really matters IS THIS WORKING?! What if the most interesting thing about work isn't what we do—but what it does to us? Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway. Next episode dropping soon - subscribe to get notified!flightcast:01KQC8A6PD9ZEEV3ZB3CJ8HDMZWed, 29 Apr 2026 09:41:00 -0000AI is here. The layoffs have started. Does anyone have a plan?

Gina Raimondo does. Two-term Governor of Rhode Island, former U.S. Commerce Secretary, the person who shepherded the CHIPS Act through Congress and personally negotiated chip exports with Chinese leadership. Harvard, Oxford, Yale Law before any of it.

Her plan: a new grand bargain between government and business. Workforce training that's continuous, employer-led, and funded by outcomes. Wage insurance for workers retraining mid-career. Tax incentives that make it more expensive to abandon workers than to retrain them. The same urgency we've poured into chips and models, applied to the tens of millions of American jobs about to change.

In this episode, Connor and Gina get into the plan, the warning ("do this wrong and we will have automated our decline"), why UBI is a cop-out, and her honest reply to whether she'd like the job of President in 2028. There's also a phrase she banned in her own cabinet that we can't in good conscience print here. Connor gets her to use it on camera. Stay for that.

Chapters

  • 00:00:00 Intro — The woman betting on America's AI future
  • 00:01:16 Finding your Andy — Love, partnership, and non-negotiables
  • 00:05:46 Faith, spirituality, and the work arena
  • 00:08:01 The AI crisis nobody's preparing for
  • 00:10:33 Winning AI without losing America
  • 00:14:34 The grand bargain — Changing incentives for companies
  • 00:17:55 More women in charge would help
  • 00:20:16 The girl in the back seat with the racing stripe
  • 00:22:39 Lightning round — Biden, bathrooms, and power perks
  • 00:30:11 Grin-fucking and the yes-man problem
  • 00:37:32 Presidential ambitions and the right moment
  • 00:41:48 Conquering the self and the Msgina Special
  • 00:48:03 Legacy, love, and what really matters

IS THIS WORKING?!

What if the most interesting thing about work isn't what we do—but what it does to us?

Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway.

Next episode dropping soon - subscribe to get notified!

]]>Winning AI *Without* Losing The American Dream — Fmr US Commerce Secretary Gina Raimondofull2983falseAI is here. The layoffs have started. Does anyone have a plan? Gina Raimondo does. Two-term Governor of Rhode Island, former U.S. Commerce Secretary, the person who shepherded the CHIPS Act through Congress and personally negotiated chip exports with Chinese leadership. Harvard, Oxford, Yale Law before any of it. Her plan: a new grand bargain between government and business. Workforce training that's continuous, employer-led, and funded by outcomes. Wage insurance for workers retraining mid-career. Tax incentives that make it more expensive to abandon workers than to retrain them. The same urgency we've poured into chips and models, applied to the tens of millions of American jobs about to change. In this episode, Connor and Gina get into the plan, the warning ("do this wrong and we will have automated our decline"), why UBI is a cop-out, and her honest reply to whether she'd like the job of President in 2028. There's also a phrase she banned in her own cabinet that we can't in good conscience print here. Connor gets her to use it on camera. Stay for that. Chapters 00:00:00 Intro — The woman betting on America's AI future 00:01:16 Finding your Andy — Love, partnership, and non-negotiables 00:05:46 Faith, spirituality, and the work arena 00:08:01 The AI crisis nobody's preparing for 00:10:33 Winning AI without losing America 00:14:34 The grand bargain — Changing incentives for companies 00:17:55 More women in charge would help 00:20:16 The girl in the back seat with the racing stripe 00:22:39 Lightning round — Biden, bathrooms, and power perks 00:30:11 Grin-fucking and the yes-man problem 00:37:32 Presidential ambitions and the right moment 00:41:48 Conquering the self and the Msgina Special 00:48:03 Legacy, love, and what really matters IS THIS WORKING?! What if the most interesting thing about work isn't what we do—but what it does to us? Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway. Next episode dropping soon - subscribe to get notified!The Slowest Career Change In History | Magician David GerardIs there a version of you that feels unattainable? For David Gerard, it was becoming a full-time magician. So he did it slowly. Twelve years slowly. VP at Sequoia-backed startups during the day, performing shows at night, catching 3 AM flights from Kansas back to his job. The double life was the bridge. He built the thing he actually wanted one night at a time while keeping the safe life going, until the gap closed enough to jump. And the magic wasn't the only thing he was keeping hidden. David buried his mental health struggles for decades. When he finally started talking about it, he did the same thing. Told one therapist. Then 20 people. Then 50. Then 100. He calls it "opening the aperture of fear slowly." It became his approach for everything. Not one dramatic leap. Just a longer, quieter path toward his authentic self.  Now, he’s directed the #1 rated show in Las Vegas, has consulted for America's Got Talent for four seasons, performs 100+ nights a year for companies like Google, coaches executives on presence, and runs men's groups. He talks about switching from “gasoline” to “solar” as a fuel source, choosing 1,000 real relationships over hundreds of thousands of followers, and why the secrets you keep are the ones that cost you the most. He also reads Connor's mind at the end. Just stay for that part. Chapters 00:00:00 Intro — Magic as armor, authenticity as freedom 00:01:26 From external validation to internal fuel 00:04:00 The 12-year runway — Marketing by day, magic by night 00:06:34 Breaking the container — The Dunkin' moment 00:07:43 Creating awe for a living — The magician's mindset 00:08:52 Relationships over reach — Building a career without fame 00:10:13 Fear as a compass — Micro-dosing on authenticity 00:12:56 Magic became armor — Pennsylvania in the early 90s 00:15:24 Practice enables presence — The subconscious mind 00:16:06 TGIF at Google — The American Idol of leadership 00:18:30 Red, yellow, green — The simplest coaching tool 00:23:09 The spiritual practice — Meditation and men's work 00:31:18 The career transition — From stage to facilitation 00:34:55 Magical moments keep coming — The Tetris game of life 00:48:56 Assumptions and repositioning — The magician as marketer 00:45:42 Feedback as fuel — Taking notes from people you want to become 00:54:24 Borrowing confidence — Faith from others when you don't have it 00:56:16 Resources for the journey — Books and practices that matter 00:58:08 The magic trick — A coincidence you won't believe IS THIS WORKING?! What if the most interesting thing about work isn't what we do—but what it does to us? Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway. Next episode dropping soon - subscribe to get notified!flightcast:01KNMNZ2DP3Y1TRCQNDRZWMNDRWed, 08 Apr 2026 13:01:00 -0000Is there a version of you that feels unattainable? For David Gerard, it was becoming a full-time magician. So he did it slowly. Twelve years slowly. VP at Sequoia-backed startups during the day, performing shows at night, catching 3 AM flights from Kansas back to his job. The double life was the bridge. He built the thing he actually wanted one night at a time while keeping the safe life going, until the gap closed enough to jump.

And the magic wasn't the only thing he was keeping hidden. David buried his mental health struggles for decades. When he finally started talking about it, he did the same thing. Told one therapist. Then 20 people. Then 50. Then 100. He calls it "opening the aperture of fear slowly." It became his approach for everything. Not one dramatic leap. Just a longer, quieter path toward his authentic self. 

Now, he’s directed the #1 rated show in Las Vegas, has consulted for America's Got Talent for four seasons, performs 100+ nights a year for companies like Google, coaches executives on presence, and runs men's groups. He talks about switching from “gasoline” to “solar” as a fuel source, choosing 1,000 real relationships over hundreds of thousands of followers, and why the secrets you keep are the ones that cost you the most. He also reads Connor's mind at the end. Just stay for that part.

Chapters

  • 00:00:00 Intro — Magic as armor, authenticity as freedom
  • 00:01:26 From external validation to internal fuel
  • 00:04:00 The 12-year runway — Marketing by day, magic by night
  • 00:06:34 Breaking the container — The Dunkin' moment
  • 00:07:43 Creating awe for a living — The magician's mindset
  • 00:08:52 Relationships over reach — Building a career without fame
  • 00:10:13 Fear as a compass — Micro-dosing on authenticity
  • 00:12:56 Magic became armor — Pennsylvania in the early 90s
  • 00:15:24 Practice enables presence — The subconscious mind
  • 00:16:06 TGIF at Google — The American Idol of leadership
  • 00:18:30 Red, yellow, green — The simplest coaching tool
  • 00:23:09 The spiritual practice — Meditation and men's work
  • 00:31:18 The career transition — From stage to facilitation
  • 00:34:55 Magical moments keep coming — The Tetris game of life
  • 00:48:56 Assumptions and repositioning — The magician as marketer
  • 00:45:42 Feedback as fuel — Taking notes from people you want to become
  • 00:54:24 Borrowing confidence — Faith from others when you don't have it
  • 00:56:16 Resources for the journey — Books and practices that matter
  • 00:58:08 The magic trick — A coincidence you won't believe

IS THIS WORKING?!

What if the most interesting thing about work isn't what we do—but what it does to us?

Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway.

Next episode dropping soon - subscribe to get notified!

]]>The Slowest Career Change In History | Magician David Gerardfull4036falseIs there a version of you that feels unattainable? For David Gerard, it was becoming a full-time magician. So he did it slowly. Twelve years slowly. VP at Sequoia-backed startups during the day, performing shows at night, catching 3 AM flights from Kansas back to his job. The double life was the bridge. He built the thing he actually wanted one night at a time while keeping the safe life going, until the gap closed enough to jump. And the magic wasn't the only thing he was keeping hidden. David buried his mental health struggles for decades. When he finally started talking about it, he did the same thing. Told one therapist. Then 20 people. Then 50. Then 100. He calls it "opening the aperture of fear slowly." It became his approach for everything. Not one dramatic leap. Just a longer, quieter path toward his authentic self.  Now, he’s directed the #1 rated show in Las Vegas, has consulted for America's Got Talent for four seasons, performs 100+ nights a year for companies like Google, coaches executives on presence, and runs men's groups. He talks about switching from “gasoline” to “solar” as a fuel source, choosing 1,000 real relationships over hundreds of thousands of followers, and why the secrets you keep are the ones that cost you the most. He also reads Connor's mind at the end. Just stay for that part. Chapters 00:00:00 Intro — Magic as armor, authenticity as freedom 00:01:26 From external validation to internal fuel 00:04:00 The 12-year runway — Marketing by day, magic by night 00:06:34 Breaking the container — The Dunkin' moment 00:07:43 Creating awe for a living — The magician's mindset 00:08:52 Relationships over reach — Building a career without fame 00:10:13 Fear as a compass — Micro-dosing on authenticity 00:12:56 Magic became armor — Pennsylvania in the early 90s 00:15:24 Practice enables presence — The subconscious mind 00:16:06 TGIF at Google — The American Idol of leadership 00:18:30 Red, yellow, green — The simplest coaching tool 00:23:09 The spiritual practice — Meditation and men's work 00:31:18 The career transition — From stage to facilitation 00:34:55 Magical moments keep coming — The Tetris game of life 00:48:56 Assumptions and repositioning — The magician as marketer 00:45:42 Feedback as fuel — Taking notes from people you want to become 00:54:24 Borrowing confidence — Faith from others when you don't have it 00:56:16 Resources for the journey — Books and practices that matter 00:58:08 The magic trick — A coincidence you won't believe IS THIS WORKING?! What if the most interesting thing about work isn't what we do—but what it does to us? Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway. Next episode dropping soon - subscribe to get notified!Why She Took the Hardest CEO Job in America | PG&E's Patti Poppe84 counts of involuntary manslaughter. A worker dying every 90 days. An empty C-suite. That's what Patti Poppe signed up for when she became CEO of PG&E. In this episode, Patti gives a masterclass in crisis leadership — and pulls back the curtain on how she turned things around. She explains how she rebuilt the leadership team from scratch, why she hung up on every executive candidate who called PG&E a "stepping stone," and what it actually looks like to double down on safety and love (yes, love) when your company has killed 84 people. Five years later, PG&E has hit a 946-day safety record, buried 1,000 miles of power lines (a huge deal), and hasn't lost a single structure to equipment fire in 3 years. If you've ever inherited a mess, led a team through something nobody trained you for, or wondered whether the hard path is actually worth taking, this episode is for you. Chapters 00:00:00 Intro — Taking the hardest CEO job in America 00:01:40 From TV broadcaster dreams to utility CEO 00:02:55 Why leave a dream job for a nightmare? 00:08:10 The turnaround playbook — Purpose, lean, and breakthrough thinking 00:10:21 Hiring for service, not stepping stones 00:24:04 The Dixie fire — Six months in and everything's burning 00:30:07 Leading through crisis — Speak up, show up, go to the problem 00:17:32 When a coworker dies every 90 days — The safety transformation 00:36:05 Holding the weight — Grief, resolve, and progress 00:39:41 Ikigai and meaningful work — When your job fuels your life 00:47:48 Wrap-up — You're putting a man on the moonflightcast:01KMJBM6Q7CXNY3Z37SRP9JT6KWed, 25 Mar 2026 11:46:00 -000084 counts of involuntary manslaughter. A worker dying every 90 days. An empty C-suite. That's what Patti Poppe signed up for when she became CEO of PG&E.

In this episode, Patti gives a masterclass in crisis leadership — and pulls back the curtain on how she turned things around.

She explains how she rebuilt the leadership team from scratch, why she hung up on every executive candidate who called PG&E a "stepping stone," and what it actually looks like to double down on safety and love (yes, love) when your company has killed 84 people.

Five years later, PG&E has hit a 946-day safety record, buried 1,000 miles of power lines (a huge deal), and hasn't lost a single structure to equipment fire in 3 years.

If you've ever inherited a mess, led a team through something nobody trained you for, or wondered whether the hard path is actually worth taking, this episode is for you.

Chapters

  • 00:00:00 Intro — Taking the hardest CEO job in America
  • 00:01:40 From TV broadcaster dreams to utility CEO
  • 00:02:55 Why leave a dream job for a nightmare?
  • 00:08:10 The turnaround playbook — Purpose, lean, and breakthrough thinking
  • 00:10:21 Hiring for service, not stepping stones
  • 00:24:04 The Dixie fire — Six months in and everything's burning
  • 00:30:07 Leading through crisis — Speak up, show up, go to the problem
  • 00:17:32 When a coworker dies every 90 days — The safety transformation
  • 00:36:05 Holding the weight — Grief, resolve, and progress
  • 00:39:41 Ikigai and meaningful work — When your job fuels your life
  • 00:47:48 Wrap-up — You're putting a man on the moon

]]>Why She Took the Hardest CEO Job in America | PG&E's Patti Poppefull2877false84 counts of involuntary manslaughter. A worker dying every 90 days. An empty C-suite. That's what Patti Poppe signed up for when she became CEO of PG&E. In this episode, Patti gives a masterclass in crisis leadership — and pulls back the curtain on how she turned things around. She explains how she rebuilt the leadership team from scratch, why she hung up on every executive candidate who called PG&E a "stepping stone," and what it actually looks like to double down on safety and love (yes, love) when your company has killed 84 people. Five years later, PG&E has hit a 946-day safety record, buried 1,000 miles of power lines (a huge deal), and hasn't lost a single structure to equipment fire in 3 years. If you've ever inherited a mess, led a team through something nobody trained you for, or wondered whether the hard path is actually worth taking, this episode is for you. Chapters 00:00:00 Intro — Taking the hardest CEO job in America 00:01:40 From TV broadcaster dreams to utility CEO 00:02:55 Why leave a dream job for a nightmare? 00:08:10 The turnaround playbook — Purpose, lean, and breakthrough thinking 00:10:21 Hiring for service, not stepping stones 00:24:04 The Dixie fire — Six months in and everything's burning 00:30:07 Leading through crisis — Speak up, show up, go to the problem 00:17:32 When a coworker dies every 90 days — The safety transformation 00:36:05 Holding the weight — Grief, resolve, and progress 00:39:41 Ikigai and meaningful work — When your job fuels your life 00:47:48 Wrap-up — You're putting a man on the moonThe Overachiever’s Guide To Effective Communication - Stanford's Matt AbrahamsMatt Abrahams teaches Stanford’s Essentials of Strategic Communication, the university’s most popular communication course. His “Think Fast. Talk Smart” talks and podcast have earned over 80 million views and listens. And the first thing he told us is that the instinct to get it perfect is the exact thing making us worse. Not just at presentations. At everything. Meetings, hard conversations, even arguments with your partner about toothpaste. (He'll explain that one.) This is also a special episode: Connor is joined by his co-founder and co-CEO of Merit America, Rebecca Taber Staehelin. Matt coaches them both live through a high-stakes all-hands that almost went sideways and feedback that made Rebecca rethink how she'd been communicating for years. They also get into what to do when your mind goes completely blank in front of your team, a trick that kills fights with your partner before they start, and why most of the time we think someone didn't listen to us — the real problem is we never checked if they understood. Check out Matt’s podcast and books here: https://www.fastersmarter.io/. Chapters 00:00:00 Intro — Be interested, not interesting 00:07:17 Polished vs. authentic 00:09:59 Being spontaneous is a skill you can practice 00:12:22 Martial arts, breathing, and being present 00:14:40 Repetition, reflection, and feedback — The only way to improve 00:18:06 The toothpaste fight and the zero-to-ten scale 00:23:55 Managing high-stakes anxiety 00:29:30 Why mistakes make you human 00:36:15 Don't assume they'll connect the dots 00:37:57 Wrap-up — Think faster, talk smarterflightcast:01KKCR4VQ4FAK2V0ZMHBWHM7TYWed, 11 Mar 2026 09:27:00 -0000Matt Abrahams teaches Stanford’s Essentials of Strategic Communication, the university’s most popular communication course. His “Think Fast. Talk Smart” talks and podcast have earned over 80 million views and listens. And the first thing he told us is that the instinct to get it perfect is the exact thing making us worse.

Not just at presentations. At everything. Meetings, hard conversations, even arguments with your partner about toothpaste. (He'll explain that one.)

This is also a special episode: Connor is joined by his co-founder and co-CEO of Merit America, Rebecca Taber Staehelin. Matt coaches them both live through a high-stakes all-hands that almost went sideways and feedback that made Rebecca rethink how she'd been communicating for years.

They also get into what to do when your mind goes completely blank in front of your team, a trick that kills fights with your partner before they start, and why most of the time we think someone didn't listen to us — the real problem is we never checked if they understood.

Check out Matt’s podcast and books here: https://www.fastersmarter.io/.

Chapters

  • 00:00:00 Intro — Be interested, not interesting
  • 00:07:17 Polished vs. authentic
  • 00:09:59 Being spontaneous is a skill you can practice
  • 00:12:22 Martial arts, breathing, and being present
  • 00:14:40 Repetition, reflection, and feedback — The only way to improve
  • 00:18:06 The toothpaste fight and the zero-to-ten scale
  • 00:23:55 Managing high-stakes anxiety
  • 00:29:30 Why mistakes make you human
  • 00:36:15 Don't assume they'll connect the dots
  • 00:37:57 Wrap-up — Think faster, talk smarter

]]>The Overachiever’s Guide To Effective Communication - Stanford's Matt Abrahamsfull2390falseMatt Abrahams teaches Stanford’s Essentials of Strategic Communication, the university’s most popular communication course. His “Think Fast. Talk Smart” talks and podcast have earned over 80 million views and listens. And the first thing he told us is that the instinct to get it perfect is the exact thing making us worse. Not just at presentations. At everything. Meetings, hard conversations, even arguments with your partner about toothpaste. (He'll explain that one.) This is also a special episode: Connor is joined by his co-founder and co-CEO of Merit America, Rebecca Taber Staehelin. Matt coaches them both live through a high-stakes all-hands that almost went sideways and feedback that made Rebecca rethink how she'd been communicating for years. They also get into what to do when your mind goes completely blank in front of your team, a trick that kills fights with your partner before they start, and why most of the time we think someone didn't listen to us — the real problem is we never checked if they understood. Check out Matt’s podcast and books here: https://www.fastersmarter.io/. Chapters 00:00:00 Intro — Be interested, not interesting 00:07:17 Polished vs. authentic 00:09:59 Being spontaneous is a skill you can practice 00:12:22 Martial arts, breathing, and being present 00:14:40 Repetition, reflection, and feedback — The only way to improve 00:18:06 The toothpaste fight and the zero-to-ten scale 00:23:55 Managing high-stakes anxiety 00:29:30 Why mistakes make you human 00:36:15 Don't assume they'll connect the dots 00:37:57 Wrap-up — Think faster, talk smarterJin Ha (Hamilton, Only Murders In The Building): Stop Performing and Start Breathing"Are you breathing?" Jin Ha's acting teacher used to interrupt class with that one question. It became a running joke among the students. It also changed how Jin Ha moves through the world. Jin Ha is a Korean American actor currently playing Aaron Burr in Hamilton on Broadway. He's also starred in Apple TV's Pachinko, worked opposite Steve Martin and Martin Short in Only Murders in the Building, with Nick Offerman on Devs, originated a role in one of Stephen Sondheim's final musicals, just wrapped season two of Apple TV's Sugar alongside Colin Farrell, and opens next in the Broadway revival of Proof this spring.  Before all of that, he was at Columbia talking himself out of a banking career after his mom gently asked if he actually wanted to work at a bank. Smart mom. This conversation is packed with ideas that have nothing to do with acting and everything to do with how we work. Jin Ha breaks down why imposter syndrome hits your best people hardest (and what to do about it), shares the "instant expert" mindset his teacher used to unlock fearlessness in impossible situations, and tells a Nick Offerman story that quietly redefines what real leadership looks like. Connor and Jin also go somewhere most work podcasts won't: mortality, ego, and what happens when you stop performing your identity and just show up. Funny, grounded, and full of things you can actually use on Monday morning.flightcast:01KJA6YFY7MFYVRWXW93ZY5W70Wed, 25 Feb 2026 11:05:00 -0000"Are you breathing?"

Jin Ha's acting teacher used to interrupt class with that one question. It became a running joke among the students. It also changed how Jin Ha moves through the world.

Jin Ha is a Korean American actor currently playing Aaron Burr in Hamilton on Broadway. He's also starred in Apple TV's Pachinko, worked opposite Steve Martin and Martin Short in Only Murders in the Building, with Nick Offerman on Devs, originated a role in one of Stephen Sondheim's final musicals, just wrapped season two of Apple TV's Sugar alongside Colin Farrell, and opens next in the Broadway revival of Proof this spring. 

Before all of that, he was at Columbia talking himself out of a banking career after his mom gently asked if he actually wanted to work at a bank. Smart mom.

This conversation is packed with ideas that have nothing to do with acting and everything to do with how we work. Jin Ha breaks down why imposter syndrome hits your best people hardest (and what to do about it), shares the "instant expert" mindset his teacher used to unlock fearlessness in impossible situations, and tells a Nick Offerman story that quietly redefines what real leadership looks like. Connor and Jin also go somewhere most work podcasts won't: mortality, ego, and what happens when you stop performing your identity and just show up.

Funny, grounded, and full of things you can actually use on Monday morning.

]]>Jin Ha (Hamilton, Only Murders In The Building): Stop Performing and Start Breathingfull3017false"Are you breathing?" Jin Ha's acting teacher used to interrupt class with that one question. It became a running joke among the students. It also changed how Jin Ha moves through the world. Jin Ha is a Korean American actor currently playing Aaron Burr in Hamilton on Broadway. He's also starred in Apple TV's Pachinko, worked opposite Steve Martin and Martin Short in Only Murders in the Building, with Nick Offerman on Devs, originated a role in one of Stephen Sondheim's final musicals, just wrapped season two of Apple TV's Sugar alongside Colin Farrell, and opens next in the Broadway revival of Proof this spring.  Before all of that, he was at Columbia talking himself out of a banking career after his mom gently asked if he actually wanted to work at a bank. Smart mom. This conversation is packed with ideas that have nothing to do with acting and everything to do with how we work. Jin Ha breaks down why imposter syndrome hits your best people hardest (and what to do about it), shares the "instant expert" mindset his teacher used to unlock fearlessness in impossible situations, and tells a Nick Offerman story that quietly redefines what real leadership looks like. Connor and Jin also go somewhere most work podcasts won't: mortality, ego, and what happens when you stop performing your identity and just show up. Funny, grounded, and full of things you can actually use on Monday morning.We've Built Cities for 20,000 Years. Why Did We Stop? — California Forever's Jan Sramek"Am I wasting some of the best years of my life?" Jan Sramek asked himself that question for years while working on one of the most audacious development projects in a generation: California Forever.  His plan: build an entirely new city on 100+ square miles of farmland in Solano County.  Not a housing development. Not a campus. A city, with schools, clinics, transit, and tens of thousands of homes in a state that's short 3 million of them. His friends thought he'd lost it. Investors wouldn't return his calls. His wife was the only person who believed in what he was doing. So he did something most founders wouldn't: he spent eight months trying to prove his own idea was wrong. He bought a 1958 government study off eBay, opened it up, and found a city planned for the exact same coordinates. Same location, to the mile. He bet everything he had. In this conversation, Jan and Connor get into what it actually feels like to build something this big when nobody believes in it yet. Jan talks about the difference between fascination and discipline, why knowing yourself matters more than knowing your market, and the moment the project almost broke him. They also cover unexpected ground: why house parties changed more minds than any ad campaign, and what competitive StarCraft taught him about getting things done. CHAPTERS Chapters 00:00:00 Building the next great American city 00:02:52 From Czech village to California visionary 00:04:11 The housing crisis nobody wants to solve 00:06:48 The leap from problem to solution 00:09:54 Proving it's not crazy — The 1958 validation 00:13:25 The inner skeptic and relentless optimism 00:21:17 Betting everything — The moment of no return 00:21:02 Silicon Valley's unique risk appetite 00:23:47 The overnight success that took ten years 00:32:53 Facing the backlash and building trust 00:47:28 House parties over TV ads — The unscalable solution 00:50:13 The big debate California needs to have 00:52:56 Starcraft and clicks per minute — The execution mindset 00:53:50 The future — Building begins IS THIS WORKING?! What if the most interesting thing about work isn't what we do—but what it does to us? Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway. Next episode dropping soon - subscribe to get notified!flightcast:01KH3YR6VC2WP1KBJC86ZYP0GQWed, 11 Feb 2026 11:28:00 -0000"Am I wasting some of the best years of my life?"

Jan Sramek asked himself that question for years while working on one of the most audacious development projects in a generation: California Forever. 

His plan: build an entirely new city on 100+ square miles of farmland in Solano County. 

Not a housing development. Not a campus. A city, with schools, clinics, transit, and tens of thousands of homes in a state that's short 3 million of them.

His friends thought he'd lost it. Investors wouldn't return his calls. His wife was the only person who believed in what he was doing.

So he did something most founders wouldn't: he spent eight months trying to prove his own idea was wrong. He bought a 1958 government study off eBay, opened it up, and found a city planned for the exact same coordinates. Same location, to the mile.

He bet everything he had.

In this conversation, Jan and Connor get into what it actually feels like to build something this big when nobody believes in it yet. Jan talks about the difference between fascination and discipline, why knowing yourself matters more than knowing your market, and the moment the project almost broke him. They also cover unexpected ground: why house parties changed more minds than any ad campaign, and what competitive StarCraft taught him about getting things done.

CHAPTERS

Chapters

  • 00:00:00 Building the next great American city
  • 00:02:52 From Czech village to California visionary
  • 00:04:11 The housing crisis nobody wants to solve
  • 00:06:48 The leap from problem to solution
  • 00:09:54 Proving it's not crazy — The 1958 validation
  • 00:13:25 The inner skeptic and relentless optimism
  • 00:21:17 Betting everything — The moment of no return
  • 00:21:02 Silicon Valley's unique risk appetite
  • 00:23:47 The overnight success that took ten years
  • 00:32:53 Facing the backlash and building trust
  • 00:47:28 House parties over TV ads — The unscalable solution
  • 00:50:13 The big debate California needs to have
  • 00:52:56 Starcraft and clicks per minute — The execution mindset
  • 00:53:50 The future — Building begins

IS THIS WORKING?!

What if the most interesting thing about work isn't what we do—but what it does to us?

Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway.

Next episode dropping soon - subscribe to get notified!

]]>We've Built Cities for 20,000 Years. Why Did We Stop? — California Forever's Jan Sramekfull3360false"Am I wasting some of the best years of my life?" Jan Sramek asked himself that question for years while working on one of the most audacious development projects in a generation: California Forever.  His plan: build an entirely new city on 100+ square miles of farmland in Solano County.  Not a housing development. Not a campus. A city, with schools, clinics, transit, and tens of thousands of homes in a state that's short 3 million of them. His friends thought he'd lost it. Investors wouldn't return his calls. His wife was the only person who believed in what he was doing. So he did something most founders wouldn't: he spent eight months trying to prove his own idea was wrong. He bought a 1958 government study off eBay, opened it up, and found a city planned for the exact same coordinates. Same location, to the mile. He bet everything he had. In this conversation, Jan and Connor get into what it actually feels like to build something this big when nobody believes in it yet. Jan talks about the difference between fascination and discipline, why knowing yourself matters more than knowing your market, and the moment the project almost broke him. They also cover unexpected ground: why house parties changed more minds than any ad campaign, and what competitive StarCraft taught him about getting things done. CHAPTERS Chapters 00:00:00 Building the next great American city 00:02:52 From Czech village to California visionary 00:04:11 The housing crisis nobody wants to solve 00:06:48 The leap from problem to solution 00:09:54 Proving it's not crazy — The 1958 validation 00:13:25 The inner skeptic and relentless optimism 00:21:17 Betting everything — The moment of no return 00:21:02 Silicon Valley's unique risk appetite 00:23:47 The overnight success that took ten years 00:32:53 Facing the backlash and building trust 00:47:28 House parties over TV ads — The unscalable solution 00:50:13 The big debate California needs to have 00:52:56 Starcraft and clicks per minute — The execution mindset 00:53:50 The future — Building begins IS THIS WORKING?! What if the most interesting thing about work isn't what we do—but what it does to us? Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway. Next episode dropping soon - subscribe to get notified!AI Won't Erase Jobs. Here’s Why — Cognizant CEO Ravi KumarRavi Kumar is one of the clearest voices on why AI will create more jobs than it replaces—which is surprising, because he's the CEO of a $35 billion company where machines already write a quarter of the code. He's not guessing. At Cognizant, the bottom 50% of his workers gained 37% productivity from AI. The top 50%? Only 17%. AI isn't replacing the bottom—it's lifting them up faster than anyone else. In this conversation, Ravi and Connor dig into what most AI conversations miss: why entry-level jobs might actually expand, not disappear. Why "problem finders" will matter more than problem solvers. And why the old model of education → work → retire is already broken and in desperate need of disruption. For anyone anxious about AI and the future of work, this is the conversation you didn't know you needed: a leader who sees what's coming and can actually explain where the opportunities are. Chapters 00:00:00 You're not competing with AI, you're competing with people using AI 00:01:27 From worst student to nuclear physicist to CEO 00:03:03 Leading through influence, not control 00:05:47 Betting on unconventional talent and upward mobility 00:08:25 Rethinking education — Learning, working, and earning together 00:11:18 AI as equalizer — The bottom gains more than the top 00:14:05 Jobs won't disappear — They'll multiply 00:15:58 The training crisis and velocity of change 00:18:27 Code generation and the agentic future 00:23:00 Amplify humans, don't replace them — A counter to Turing 00:31:21 Corporate responsibility and the Synapse Initiative 00:34:16 What keeps him up at night — Regulation, inequality, and the race 00:38:55 Corporations as platforms for societal change 00:40:41 Advice for the next generation — Master interdisciplinary thinkingflightcast:01KFX09CZDT6RJDAEKRNC8YMG4Tue, 27 Jan 2026 21:08:00 -0000Ravi Kumar is one of the clearest voices on why AI will create more jobs than it replaces—which is surprising, because he's the CEO of a $35 billion company where machines already write a quarter of the code.

He's not guessing. At Cognizant, the bottom 50% of his workers gained 37% productivity from AI. The top 50%? Only 17%. AI isn't replacing the bottom—it's lifting them up faster than anyone else.

In this conversation, Ravi and Connor dig into what most AI conversations miss: why entry-level jobs might actually expand, not disappear. Why "problem finders" will matter more than problem solvers. And why the old model of education → work → retire is already broken and in desperate need of disruption.

For anyone anxious about AI and the future of work, this is the conversation you didn't know you needed: a leader who sees what's coming and can actually explain where the opportunities are.

Chapters

  • 00:00:00 You're not competing with AI, you're competing with people using AI
  • 00:01:27 From worst student to nuclear physicist to CEO
  • 00:03:03 Leading through influence, not control
  • 00:05:47 Betting on unconventional talent and upward mobility
  • 00:08:25 Rethinking education — Learning, working, and earning together
  • 00:11:18 AI as equalizer — The bottom gains more than the top
  • 00:14:05 Jobs won't disappear — They'll multiply
  • 00:15:58 The training crisis and velocity of change
  • 00:18:27 Code generation and the agentic future
  • 00:23:00 Amplify humans, don't replace them — A counter to Turing
  • 00:31:21 Corporate responsibility and the Synapse Initiative
  • 00:34:16 What keeps him up at night — Regulation, inequality, and the race
  • 00:38:55 Corporations as platforms for societal change
  • 00:40:41 Advice for the next generation — Master interdisciplinary thinking

]]>AI Won't Erase Jobs. Here’s Why — Cognizant CEO Ravi Kumarfull2619falseRavi Kumar is one of the clearest voices on why AI will create more jobs than it replaces—which is surprising, because he's the CEO of a $35 billion company where machines already write a quarter of the code. He's not guessing. At Cognizant, the bottom 50% of his workers gained 37% productivity from AI. The top 50%? Only 17%. AI isn't replacing the bottom—it's lifting them up faster than anyone else. In this conversation, Ravi and Connor dig into what most AI conversations miss: why entry-level jobs might actually expand, not disappear. Why "problem finders" will matter more than problem solvers. And why the old model of education → work → retire is already broken and in desperate need of disruption. For anyone anxious about AI and the future of work, this is the conversation you didn't know you needed: a leader who sees what's coming and can actually explain where the opportunities are. Chapters 00:00:00 You're not competing with AI, you're competing with people using AI 00:01:27 From worst student to nuclear physicist to CEO 00:03:03 Leading through influence, not control 00:05:47 Betting on unconventional talent and upward mobility 00:08:25 Rethinking education — Learning, working, and earning together 00:11:18 AI as equalizer — The bottom gains more than the top 00:14:05 Jobs won't disappear — They'll multiply 00:15:58 The training crisis and velocity of change 00:18:27 Code generation and the agentic future 00:23:00 Amplify humans, don't replace them — A counter to Turing 00:31:21 Corporate responsibility and the Synapse Initiative 00:34:16 What keeps him up at night — Regulation, inequality, and the race 00:38:55 Corporations as platforms for societal change 00:40:41 Advice for the next generation — Master interdisciplinary thinkingYou Can Change a Lot More Than You Think — Somatic Coach Harley FrankHow much can people actually change? According to renowned somatic coach Harley Frank, a whole lot more than you might think. Once a startup executive living with chronic anxiety and depression, Frank now works with leaders around the world using somatic body-based practices to help them reclaim choice, vitality, and presence. In this conversation, Harley and Connor explore why many of the traits we think are “just who we are” in work and life are actually frozen patterns in the nervous system—and how practices like somatics, inner-child work, and embodied awareness can unlock real transformation.  This episode is about leadership, creativity, healing, and what becomes possible when we stop trying to think our way out of pain—and learn to feel our way through it. CHAPTERS Chapters 00:00:00 Intro — You can transform more than you think 00:03:47 From tech executive to somatic coach 00:12:10 What somatics actually is 00:14:59 Why shame runs the show 00:17:19 Inner child work and neural rewiring 00:24:45 Leadership is about embodiment 00:31:08 The first step — Building a daily practice 00:37:40 Feel your part, no more 00:43:05 Pain vs. suffering — The 90-second rule 00:51:53 Shame, technology, and staying present IS THIS WORKING?! What if the most interesting thing about work isn't what we do—but what it does to us? Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway. Next episode dropping soon - subscribe to get notified!flightcast:01KCPDBC26V8A4GDJWPE539P06Wed, 17 Dec 2025 15:49:00 -0000How much can people actually change? According to renowned somatic coach Harley Frank, a whole lot more than you might think.

Once a startup executive living with chronic anxiety and depression, Frank now works with leaders around the world using somatic body-based practices to help them reclaim choice, vitality, and presence.

In this conversation, Harley and Connor explore why many of the traits we think are “just who we are” in work and life are actually frozen patterns in the nervous system—and how practices like somatics, inner-child work, and embodied awareness can unlock real transformation. 

This episode is about leadership, creativity, healing, and what becomes possible when we stop trying to think our way out of pain—and learn to feel our way through it.

CHAPTERS

Chapters

  • 00:00:00 Intro — You can transform more than you think
  • 00:03:47 From tech executive to somatic coach
  • 00:12:10 What somatics actually is
  • 00:14:59 Why shame runs the show
  • 00:17:19 Inner child work and neural rewiring
  • 00:24:45 Leadership is about embodiment
  • 00:31:08 The first step — Building a daily practice
  • 00:37:40 Feel your part, no more
  • 00:43:05 Pain vs. suffering — The 90-second rule
  • 00:51:53 Shame, technology, and staying present

IS THIS WORKING?!

What if the most interesting thing about work isn't what we do—but what it does to us?

Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway.

Next episode dropping soon - subscribe to get notified!

]]>You Can Change a Lot More Than You Think — Somatic Coach Harley Frankfull3657falseHow much can people actually change? According to renowned somatic coach Harley Frank, a whole lot more than you might think. Once a startup executive living with chronic anxiety and depression, Frank now works with leaders around the world using somatic body-based practices to help them reclaim choice, vitality, and presence. In this conversation, Harley and Connor explore why many of the traits we think are “just who we are” in work and life are actually frozen patterns in the nervous system—and how practices like somatics, inner-child work, and embodied awareness can unlock real transformation.  This episode is about leadership, creativity, healing, and what becomes possible when we stop trying to think our way out of pain—and learn to feel our way through it. CHAPTERS Chapters 00:00:00 Intro — You can transform more than you think 00:03:47 From tech executive to somatic coach 00:12:10 What somatics actually is 00:14:59 Why shame runs the show 00:17:19 Inner child work and neural rewiring 00:24:45 Leadership is about embodiment 00:31:08 The first step — Building a daily practice 00:37:40 Feel your part, no more 00:43:05 Pain vs. suffering — The 90-second rule 00:51:53 Shame, technology, and staying present IS THIS WORKING?! What if the most interesting thing about work isn't what we do—but what it does to us? Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway. Next episode dropping soon - subscribe to get notified!Want to Keep Fighting? Stay Optimistic — ACLU's Anthony RomeroAnthony Romero has led the ACLU for nearly a quarter century—through four presidents, constitutional showdowns, and a political landscape that feels more chaotic every day. And yet, when you sit across from him, you don’t feel panic. You feel steadiness. Clarity. A kind of grounded purpose that’s rare in work shaped by crisis. In this conversation, recorded inside ACLU headquarters in New York, Romero and Connor talk about what it means to do work that is forged in conflict while still protecting your humanity. Anthony shares how he stays centered amid tragedy and noise, why “slowing things down” can be a form of progress, and how small daily practices—kindness, discipline, honest self-reflection—are what keep him from burning out. We also zoom out: What does leadership look like when the stakes feel impossibly high? What happens when your work requires you to step into friction again and again? And what responsibility does our generation have for the systems—and the workplace cultures—we’re leaving behind? For anyone who cares about doing meaningful work without losing themselves in the process, this conversation offers a rare mix of realism, agency, and genuine optimism. CHAPTERS Chapters 00:00:00 Intro — Fighting for democracy in a constitutional crisis 00:02:57 Constitutional crisis or opportunity for resistance? 00:04:14 Leading through tragedy and staying centered 00:07:07 Winning by losing — ACLU's litigation strategy 00:10:43 Redefining success and bringing the public along 00:12:20 The but-for test — Would America be worse without the ACLU? 00:16:53 Best case, worst case — America's future scenarios 00:20:48 Looking at the map — Opportunities in every state 00:23:01 The last man standing — Embracing friction 00:27:01 This is a rental car — Legacy and succession 00:29:08 How my generation f*cked it up 00:32:49 Message to young leaders — Keep fighting, it matters IS THIS WORKING?! What if the most interesting thing about work isn’t what we do—but what it does to us? Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway. Next episode dropping soon - subscribe to get notified!flightcast:01KAXE5SKR0H1RW1KKRSGHBFDRWed, 03 Dec 2025 21:57:00 -0000Anthony Romero has led the ACLU for nearly a quarter century—through four presidents, constitutional showdowns, and a political landscape that feels more chaotic every day. And yet, when you sit across from him, you don’t feel panic. You feel steadiness. Clarity. A kind of grounded purpose that’s rare in work shaped by crisis.

In this conversation, recorded inside ACLU headquarters in New York, Romero and Connor talk about what it means to do work that is forged in conflict while still protecting your humanity. Anthony shares how he stays centered amid tragedy and noise, why “slowing things down” can be a form of progress, and how small daily practices—kindness, discipline, honest self-reflection—are what keep him from burning out.

We also zoom out: What does leadership look like when the stakes feel impossibly high? What happens when your work requires you to step into friction again and again? And what responsibility does our generation have for the systems—and the workplace cultures—we’re leaving behind?

For anyone who cares about doing meaningful work without losing themselves in the process, this conversation offers a rare mix of realism, agency, and genuine optimism.

CHAPTERS

Chapters

  • 00:00:00 Intro — Fighting for democracy in a constitutional crisis
  • 00:02:57 Constitutional crisis or opportunity for resistance?
  • 00:04:14 Leading through tragedy and staying centered
  • 00:07:07 Winning by losing — ACLU's litigation strategy
  • 00:10:43 Redefining success and bringing the public along
  • 00:12:20 The but-for test — Would America be worse without the ACLU?
  • 00:16:53 Best case, worst case — America's future scenarios
  • 00:20:48 Looking at the map — Opportunities in every state
  • 00:23:01 The last man standing — Embracing friction
  • 00:27:01 This is a rental car — Legacy and succession
  • 00:29:08 How my generation f*cked it up
  • 00:32:49 Message to young leaders — Keep fighting, it matters

IS THIS WORKING?!

What if the most interesting thing about work isn’t what we do—but what it does to us?

Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway.

Next episode dropping soon - subscribe to get notified!

]]>Want to Keep Fighting? Stay Optimistic — ACLU's Anthony Romerofull2035falseAnthony Romero has led the ACLU for nearly a quarter century—through four presidents, constitutional showdowns, and a political landscape that feels more chaotic every day. And yet, when you sit across from him, you don’t feel panic. You feel steadiness. Clarity. A kind of grounded purpose that’s rare in work shaped by crisis. In this conversation, recorded inside ACLU headquarters in New York, Romero and Connor talk about what it means to do work that is forged in conflict while still protecting your humanity. Anthony shares how he stays centered amid tragedy and noise, why “slowing things down” can be a form of progress, and how small daily practices—kindness, discipline, honest self-reflection—are what keep him from burning out. We also zoom out: What does leadership look like when the stakes feel impossibly high? What happens when your work requires you to step into friction again and again? And what responsibility does our generation have for the systems—and the workplace cultures—we’re leaving behind? For anyone who cares about doing meaningful work without losing themselves in the process, this conversation offers a rare mix of realism, agency, and genuine optimism. CHAPTERS Chapters 00:00:00 Intro — Fighting for democracy in a constitutional crisis 00:02:57 Constitutional crisis or opportunity for resistance? 00:04:14 Leading through tragedy and staying centered 00:07:07 Winning by losing — ACLU's litigation strategy 00:10:43 Redefining success and bringing the public along 00:12:20 The but-for test — Would America be worse without the ACLU? 00:16:53 Best case, worst case — America's future scenarios 00:20:48 Looking at the map — Opportunities in every state 00:23:01 The last man standing — Embracing friction 00:27:01 This is a rental car — Legacy and succession 00:29:08 How my generation f*cked it up 00:32:49 Message to young leaders — Keep fighting, it matters IS THIS WORKING?! What if the most interesting thing about work isn’t what we do—but what it does to us? Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway. Next episode dropping soon - subscribe to get notified!Follow the Laughter, Find the Truth — Comedian Sarah CooperSarah Cooper went viral for lip-syncing Donald Trump on TikTok — and suddenly, the world knew her face. From there came a Netflix special, a memoir, acting alongside Jerry Seinfeld, and guest-hosting Jimmy Kimmel Live. But there was also everything people didn’t see: the disorientation of sudden fame, the pressure to keep performing, and the years of self-doubt that followed. In this conversation, Sarah and Connor go beneath the viral moment and explore how comedy became her way of moving through pain, divorce, and reinvention. They unpack how self-awareness fuels creativity, how intuition beats optimization, and how humor itself reveals the deeper work of resilience and self-leadership. CHAPTERS Chapters 00:00:00 Intro — Sarah Cooper on success, doubt, and meaning 00:01:13 From Google to comedy 00:04:36 Going viral & getting humbled 00:07:22 The hangover after fame 00:11:03 Perfectionism, family, and learning to fail 00:15:43 Rediscovering herself after divorce 00:18:10 Comedy as power & perspective 00:21:24 The human voice in an AI age 00:27:01 Fame, isolation, and honesty 00:32:04 Leaving Google and finding courage 00:38:59 Manifestation gone wrong (the SNL story) 00:45:00 Group therapy & saying what’s real 00:58:25 Legacy — making people feel less alone IS THIS WORKING?! What if the most interesting thing about work isn’t what we do—but what it does to us? Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway. Next episode dropping soon - subscribe to get notified!flightcast:01K9ST5DRXQXS904M5AP184FEPWed, 12 Nov 2025 11:01:00 -0000Is This Working?!Sarah Cooper went viral for lip-syncing Donald Trump on TikTok — and suddenly, the world knew her face. From there came a Netflix special, a memoir, acting alongside Jerry Seinfeld, and guest-hosting Jimmy Kimmel Live.

But there was also everything people didn’t see: the disorientation of sudden fame, the pressure to keep performing, and the years of self-doubt that followed.

In this conversation, Sarah and Connor go beneath the viral moment and explore how comedy became her way of moving through pain, divorce, and reinvention. They unpack how self-awareness fuels creativity, how intuition beats optimization, and how humor itself reveals the deeper work of resilience and self-leadership.

CHAPTERS

Chapters

  • 00:00:00 Intro — Sarah Cooper on success, doubt, and meaning
  • 00:01:13 From Google to comedy
  • 00:04:36 Going viral & getting humbled
  • 00:07:22 The hangover after fame
  • 00:11:03 Perfectionism, family, and learning to fail
  • 00:15:43 Rediscovering herself after divorce
  • 00:18:10 Comedy as power & perspective
  • 00:21:24 The human voice in an AI age
  • 00:27:01 Fame, isolation, and honesty
  • 00:32:04 Leaving Google and finding courage
  • 00:38:59 Manifestation gone wrong (the SNL story)
  • 00:45:00 Group therapy & saying what’s real
  • 00:58:25 Legacy — making people feel less alone

IS THIS WORKING?!

What if the most interesting thing about work isn’t what we do—but what it does to us?

Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway.

Next episode dropping soon - subscribe to get notified!

]]>Follow the Laughter, Find the Truth — Comedian Sarah CooperIs This Working?!full3561falseSarah Cooper went viral for lip-syncing Donald Trump on TikTok — and suddenly, the world knew her face. From there came a Netflix special, a memoir, acting alongside Jerry Seinfeld, and guest-hosting Jimmy Kimmel Live. But there was also everything people didn’t see: the disorientation of sudden fame, the pressure to keep performing, and the years of self-doubt that followed. In this conversation, Sarah and Connor go beneath the viral moment and explore how comedy became her way of moving through pain, divorce, and reinvention. They unpack how self-awareness fuels creativity, how intuition beats optimization, and how humor itself reveals the deeper work of resilience and self-leadership. CHAPTERS Chapters 00:00:00 Intro — Sarah Cooper on success, doubt, and meaning 00:01:13 From Google to comedy 00:04:36 Going viral & getting humbled 00:07:22 The hangover after fame 00:11:03 Perfectionism, family, and learning to fail 00:15:43 Rediscovering herself after divorce 00:18:10 Comedy as power & perspective 00:21:24 The human voice in an AI age 00:27:01 Fame, isolation, and honesty 00:32:04 Leaving Google and finding courage 00:38:59 Manifestation gone wrong (the SNL story) 00:45:00 Group therapy & saying what’s real 00:58:25 Legacy — making people feel less alone IS THIS WORKING?! What if the most interesting thing about work isn’t what we do—but what it does to us? Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway. Next episode dropping soon - subscribe to get notified!