Exit Paradox

Most people believe that once you achieve financial freedom, life becomes lighter, calmer, and more fulfilling. But what if wealth quietly destroys your drive, energy, and sense of aliveness? In this private webinar, Anastasia Koroleva, founder of Exit Paradox, reveals a powerful and deeply counterintuitive pattern she has observed in founders and CEOs after major exits — a state she calls post-we...

In this conversation, serial entrepreneur and exited founder Omar Haroun reveals the hidden emotional cost of success, the identity collapse many founders experience post-exit, and why wealth alone often fails to deliver fulfillment. Omar is a multi-exit entrepreneur and investor who has spent years studying the psychological and emotional realities of life after selling a business. He reflects on...

After selling her bootstrapped company in a 9-figure all-cash exit, Anastasia Koroleva expected freedom, joy, and the end of struggle. Instead, she encountered something no one talks about—the Wealth Lag. In this deeply honest and research-backed breakdown, Anastasia reveals the emotional crash that happens after financial freedom: the confusion, cognitive dissonance, identity loss, and the quiet...

On this podcast we've explored many dramatic post exit stories. Tales of existential crisis, addictions to drugs, alcohol, sex and obsessive money chasing, extreme sports, mind blowing adventures and long spiritual journeys to faraway lands. Daniel Kivatinos journey is different and just as important to hear. His pause after selling his company didn't push him into a new path. It gave him clarity...

One of the hardest parts of life after an exit is striking that balance.  On the one hand, enjoying the incredible lifestyle we've earned. On the other, protecting and growing the wealth it took so much to build.  My friend Justin Donald has lived that tension and he wrote a best selling book about it and created a community called Lifestyle Investor to help others walk the same path. It's easy to...

Barak Kaufman, founder of Post‑Exit Founders (PEF), grew a 5,000+ member community in four years by word of mouth.  He shares what he’s learned from their stories: what works after an exit and what does not.   Barak is now partner at VC firm Vine Ventures in New York City and Tel Aviv. Connect with Barak: Linkedin: https://www.linkedin.com/in/barakk/ X: @barak-kaufman PEF: https://pef.xyz/ Vine Ve...

Some exits, they just stop us in our tracks. Not because of the money or the business genius, but because of the radical personal transformation that followed.  Dan Berger's story is one of those. Seven years ago, he sold social tables for around $100 million million dollars. And like so many of us, the exit cracked something open. The wealth, the time, the freedom. It didn't bring peace at first....

Today’s episode is different. My guest isn’t an exited founder but she’s someone we all need. Amy Castoro helps families have honest conversations about wealth—the kind most of us were never taught to have. She shares practical tools from her firm’s 50 years of experience advising some of the wealthiest families in America.  Her work focuses on the emotional side of money—how we build trust, prote...

My friend Jay Radia doesn’t just build businesses—he builds momentum. He’s a three-time tech founder and a prolific angel investor. Since his last exit two years ago, he’s been building Blissgrowth—a venture studio that partners exclusively with exited founders. Why did he choose this path? What has he learnt so far? Was it the right move? For a while, Jay also co-hosted The Joyful Entrepreneur Po...

Linda Abraham is one of the most extraordinary women I’ve ever met. She’s in a class of her own. She’s been navigating the post-exit world for 28 years, ever since her first exit. And what an exit it was: a 5X return to investors in just two years! She went on to lead her second company, comScore, from founding to IPO—building it into a global powerhouse in digital analytics, with offices in 23 co...

My guest today is Adam Rossi. He sold his company, Platinum Solutions, 14 years ago and walked away with life changing wealth. But what hit him first after his exit was regret. We talk about how he came to terms with his new reality, searched for his new purpose, and dealt with losing his found identity. My favorite part of Adam's story is that he built his company with his wife, Leila, and their...

Mike Brown's post-exit journey led him from chaos to clarity, but not right away. He had to go through a painful divorce, a business failure, financial losses and emotional turmoil. Today we are talking about what he's learned and why he decided to dedicate himself to coaching.  🔗 CONNECT WITH MIKE: 🎥 YouTube Channel - ‪@mbrown_co‬ 🐦 X (Twitter) - https://x.com/mbrown_co 📸 Instagram - @mbrown....

VCs notoriously avoid investing in married couples, fearing that personal conflicts could sink the business.  Yet, the Lazerows defied that norm—building not just one, but two successful companies together, culminating in an $800M exit. They didn’t just make it work; they mastered it—and then wrote a book about it. Today, we’ll dive deep into what exactly they did to make it work—and what they wis...

My guest today, Josh Payne, has developed fascinating insights and systems to do just that. Josh sold his company, Stack Commerce, for nearly $100 million 4 years ago.  A huge milestone - but as all exited founders know, the real story starts after the deal is done. Today, he’s building again - but with a completely different approach. Josh isn’t optimizing for another massive exit. He’s after som...

What would you do if you sold your company for 300 million dollars? Retire? Explore the world? Do all these other things you had no time to do while building a business? This is not what my friend Alex Macdonald did when he sold his company Velocity Black two years ago. In fact, Alex made it quite impossible for himself to have any kind of post-exit sabbatical. Why? Well, Alex has seen enough of h...

My guest today is Cory Janssen, co-founder of Investopedia.  Cory sold the business 17 years ago, but what came next was far from the smooth ride he or anyone might have expected. He spent years in painful trial and error, half-heartedly starting new ventures while avoiding real work, experimenting with professional investing and retirement. None of it satisfied his deeper need for the sense of pu...

This interview is a special one for me.  Michael Miller has been a friend for over 15 years and has made a huge difference in my life.  He's a Vedic meditation teacher who taught me to meditate at a time when I was searching for clarity and tranquility following a life-changing exit. Since then, meditation has been my go-to tool for healing, finding peace, processing ideas, and making decisions. ...

My dear friend Sarah Douglass sold her incredibly successful e-commerce business three years ago, achieving the financial freedom she had always dreamed of. But soon after, she found herself grappling with a new challenge: balancing her newfound success with an ever-deepening desire for contentment and a powerful drive to create impact. In today’s conversation, Sarah shares her journey with disarm...

Tim Schumacher is the exited founder and former CEO of Sedo, one of the world's largest domain marketplaces, which he led for over a decade before stepping down 13 years ago. What sets Tim apart is how he mastered the elusive work -life balance while still building his company, something most entrepreneurs only dream of. This balance helped him avoid the emotional rollercoaster that so many of us...

Rick Eigenbrod is a deeply respected thinker in the post-exit world.  A clinical psychologist and co-author of the classic Yale paper What’s Next: The Entrepreneur’s Epilogue, he’s spent years guiding founders through life after the exit as an executive coach.  In this conversation, we get into why Rick believes a “death of who we used to be” and a subsequent "re-birth" are inevitable post-exit, a...

Roy Rubin the visionary founder of Magento, built the open source e-commerce platform from the ground up, leading it to a remarkable exit to eBay in just four years. He then stayed on at eBay for two years, but felt suffocated by corporate walls. That's when it hit him.  He barely knew his family anymore.  So he and his wife pulled their kids out of school, packed up. and set off on an open-ended...

Ten years ago, Brock Weatherup sold his first company, Pet360.com, to PetSmart for $160 million.  It took under five years to build. Since then, he’s had two more successful exits, but two years ago, his journey took an unexpected turn when a life-changing medical diagnosis reshaped his entire outlook.  In this episode, Brock talks about the secrets behind his consistent success, what keeps him op...

Three years ago, Scott Wolfe sold his company, Levelset, for half a billion dollars.  Excited and relieved at first, he soon found himself deeply frustrated with the reality that his vision for the business would now never be realized.  Scott is a natural creative who sees building a business as an artistic endeavor.  It was this intrinsic need to create that sustained him through the grueling jou...

My friend Jonathan has chosen to remain anonymous in exchange for stepping outside his comfort zone — and that he did! Eight years ago, he began a gradual exit from his incredibly successful, bootstrapped company. This strategic approach had an unexpected benefit: it smoothed his post-exit transition, making it more manageable both emotionally and financially. His search for a new purpose—a length...

Jason Kirby. He Sold Liquid Sky software to Walmart six years ago, but became disillusioned when Walmart abruptly scrapped the company's ambitious plans.  Seeking a new direction, Jason joined Generation Esports, rapidly scaled it and exited three years ago. This last exit prompted Jason to reassess his priorities, leading him to focus on family, health and meaningful work.  This shift inspired hi...