Episodes

Ben Sheppard has built companies, watched them fall apart, and dealt with the mental wreckage that comes with that. In this episode, he gets into what that season of his life looked like and what it taught him, both as someone who lived it and as someone who now sits with other founders in the middle of theirs. We talk about the mental toll of rapid turnarounds, the habit of mentally replaying every bad negotiation, and why so many founders end up suffering in silence when they don't have to....

Dr. Michael Freeman has spent decades studying entrepreneur mental health, and what he found is fascinating. Dr. Freeman is a psychiatrist, a fourth generation serial entrepreneur, and a Clinical Professor of Psychiatry at UC San Francisco School of Medicine. He is also the founder of Econa, the global center of excellence for entrepreneur mental wellness. His research, conducted with colleagues from UC Berkeley and the Gallup Organization and supported by the Kauffman Foundation, has produced ...

Andy Walsh moved from Australia to New York City with a four month old baby, no financial safety net, and a bootstrapped business. He built it for seven years, exited twice, and then crashed. This is what he learned on the other side. In this episode: Andy takes us through the decision to pack up his life and bet on himself in a new country with a newborn, and what that pressure quietly did to his mental health over time. He talks about what depression and anxiety actually looked like while he...

Lisa Mikkelsen: How VCs Can Better Support Founder Mental Health Most investors will tell you they care about their founders, but Lisa Mikkelsen wants to challenge them to do more. Lisa is the Head of Global Human Capital at Flourish Ventures, where she has built programming specifically designed to support founder wellbeing, including CEO retreats, founder peer circles, and individualized coaching. She is one of the few people in venture capital who has moved from caring about this issue to ac...

In the span of four and a half years, Jeff Johnston lost his son Seth to a fentanyl overdose, his wife Prudence to alcohol, and his mother three months after that. Out of that unimaginable grief, he found a mission. And three weeks after Seth died, Seth's daughter and Jeff's granddaughter Brighton was born, the brightest thing to emerge from the darkest season of his life. She gave the platform its name. Most people who lose what Jeff lost don't come back from it. He did, and then he made a pro...

Everyone talks about burning out on the way to the exit, but nobody talks about what happens after. Nick Merich co-founded Songlink, built it to 22 million users, and sold it to Linktree. Then he felt like he jumped off a cliff, and there was no bottom. In this episode: Nick takes us behind the highlight reel. The perfectly crafted LinkedIn posts, the Instagram moments, the version of yourself you put out into the world when you're building something and desperately need it to work. He tal...

Shaler Houser built and sold four companies over three decades. He also lost everything more than once, not just financially, but personally. In this episode, I sit down with Shaler Houser, a 4x exited founder and Partner at Founderville VC, who has spent nearly three decades building companies, losing everything, rebuilding, and using every hard-won lesson to invest in and support the founders coming up behind him. This is the most honest conversation I've had about addiction, identity, and w...

Every founder deals with self-doubt, but most never tell anyone. In the very first episode of The Founder Exhale, I sit down with Grant Winns, an 8-time founder with 4 successful exits, including the globally recognized brand BYLT Basics, and CEO of Yuna Health, an AI-native mental health platform built to fill the gap between crisis care and traditional therapy. Grant gets real about the mental health challenges across two decades of entrepreneurship, what self-doubt actually looks like from ...

Here's why I started this podcast and what you can expect.