PODCAST · business
Exit Paradox
by Anastasia Koroleva
I'm Anastasia Koroleva, a 4x exited founder exploring life after selling a business with some of the most remarkable post-exit entrepreneurs in the world. Together, we rediscover purpose, redefine success, master investing, and build fulfilling lives and families.Having survived a 9-digit exit, I dedicated a decade to researching the deepest challenges faced by entrepreneurs after a business sale. This podcast is the platform to share my and other exited founders' hard-earned wisdom with the world.To join our community, please subscribe and share your thoughts. I’d love to hear from you 🙏.
Episodes
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Why Building Again Can Be Harder After Success | Eric Ries
Building a second company after a successful exit can look easier. You have experience, a network and financial freedom. But one of the forces that carried you through the first company may no longer be there: financial necessity. Eric Ries, author of The Lean Startup and Incorruptible, joins...
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Post-Wealth Expert: How To Re-ignite Drive and Energy After Financial Success
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...
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Omar Haroun: “Outsized Impact is Incredibly Rewarding”
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...
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The Wealth Lag: What Happens AFTER Financial Freedom
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...
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Daniel Kivatinos Post-Exit: Why I Am Building Again
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...
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Justin Donald: The Post‑Wealth Work‑Life Balance
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...
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5,000+ Post-Exit Founders: What Actually Works with Barak Kaufman
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...
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$100M Exit, Sex Addiction, and the Fight to Belong
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…
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Wealth vs Family: An Expert’s View
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...
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Venture Studio as a Post-Exit Path
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…
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2 Exits + 4 Kids = 1 Incredible Woman
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,...
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How to Build, Exit, and Stay Married
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...
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Post-Exit: From Chaos to Clarity
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...
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$800M Exit: “Shoveling Shit” in Business and Marriage
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…
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From $100M Exit to Fulfilment: Josh Payne’s Playbook
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...
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Alex Macdonald. A $300M Exit is No Reason to Retire
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…
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Cory Janssen. 17 Years Post-Exit: Insights from Investopedia’s Founder
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…
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Michael Miller. Meditation: the Ultimate Post-Exit Medicine
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,...
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Sarah Douglass. Post-Wealth Search for Happiness
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…
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Tim Schumacher. Sedo’s Exited Founder on Work-Life Balance
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...
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Rick Eigenbrod. “Post-Exit Death is Inevitable”
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...
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Roy Rubin. Magento’s Exited Founder: Globetrotting and the Search for Purpose
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...
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Brock Weatherup. Secrets of Successful Sequels
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...
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Scott Wolfe. After $500M Exit: “My Vision Is Forever Unfinished"
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...
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Johnathan. 'Life Forced a New Purpose on Me'
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...
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Jason Kirby. From Exit to Ease: Letting Go of the Stress
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…
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Matthew Johnson. Prolific Exited Entrepreneur on Work-Life Balance
Matthew Johnson sold his healthcare software company 11 years ago, after leading it through three rounds of fundraising in just three years. Alongside his twin brother Nathan, he then acquired and transformed TruConnect into a telecom powerhouse. Matthew also co-founded the technology investment...
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Bill Flagg. 5 Exits Later: Pursuit of Inspiration
Bill Flagg spent 20 years building 5 incredibly successful tech businesses, then unexpectedly sold them all. To his own surprise, the thrill of building businesses faded, and he found himself craving a pause, a chance to become a beginner again and enjoy the simple things in life. Two years ago,...
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Tony Kula. Post-Exit Shift: From Workaholic to Ironman
Tony Kula. He has built three businesses, exiting his first in his mid 20-s and spending two decades turning the next into a video distribution powerhouse, which he sold six years ago. His latest venture, MeetYoo, skyrocketed during the pandemic, but faced serious challenges afterward, prompting...
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Shane Neman. Secrets of Post-Exit Happiness
Shane Neman successfully built and exited two iconic businesses: JoonBug, a digital events powerhouse, and EZ Texting, the largest business SMS software platform in the US. Today, he manages a substantial real estate portfolio, invested in over 50 startups, and authored the book called Nightlife...
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Ben White. 'Dark Decade' After $800M Exit: Addiction. Divorce & Financial Losses
Ben White. He's sold three businesses so far for $80M, $88M and $800M. It was the last exit 16 years ago that hit him hard. What followed was a dark decade filled with divorce, addiction and significant financial losses. However, today Ben is the happiest he's ever been. In this episode we…
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Alex Bean. From $2.5B Exit to Fulfillment and Impact.
Alex Bean has recently sold his fintech company Divvi for $2.5 billion. Today, he runs a VC firm called Tandem and has written a book titled The Factory for Good on turning your life into a force for positive impact. In this episode, we explore the emotional complexities of wealth and discuss why...
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CK Kim. Recovering from a $510M Exit.
CK Kim is a serial tech entrepreneur who recently completed his second exit, exceeding $510M. To recover, CK took a year -long sabbatical. During his travels, he reflected on his experiences and distilled his insights into clear and powerful ideas. In this episode, we discussed the importance of...
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Preston Rutherford: Missed Exit
Preston Rutherford. His company was sold in a 9-figure exit 5 years ago. A couple of years later, the combined company had a 10-digit IPO. But Preston wasn't there to experience it. While he regrets exiting too early, he acknowledges that the exit propelled him into an intense personal growth...
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Gil Eyal: How Being a People Person Made Me Successful
Four years ago Gil Eyal sold HYPR - a software business which revolutionized the way big agencies and brands run influencer marketing. Today, Gil runs a venture capital firm which adds value to consumer tech companies by bringing celebrities onboard. In this episode, we discuss overcoming a...
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Craig Follett: Art Is My Post-Exit Purpose & Business
Craig Follett built Universe.com, a social marketplace for events, and sold it to Ticketmaster in 2015. Following the sale, Craig grew the business 30-fold and took the company global before leaving in 2019. He then found his calling in building Peggy.com, a secure marketplace for buying and...
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Dave Hersh: Post-Exit Rebirth: Finding Self, Sovereignty, and Inexhaustible Fuel Sources
Dave Hersh. He sold his company through an IPO 13 years ago, then spent several years with the VC firm Andreessen Horowitz.Today, Dave is more fulfilled and productive than ever.He credits a 10-year existential crisis that led to his “deep reprogramming” and “rebirth.”Today he talks to us about...
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Mike Pollack: My Post-Exit Identity: Student of Life
Mike Pollack sold his third business 6 years ago and has since, through trial and error, crafted a unique formula that balances happiness with a high likelihood of continued business success. In this episode, he shares this formula with us, delving into how to identify your true zone of…
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$100M-Net-Worth Retired Founder: Chasing Energy Instead of Money
Today's guest has chosen to remain anonymous to ensure the utmost authenticity and vulnerability in sharing his story. Four years ago, he fully exited his business and now describes his life as post-economic. He realized he had a money addiction his entire life and took a radical step to address...
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Laurent Vernhes: Quality-Obsessed Exited Founder: "Business is a Form of Art"
Laurent Vernhes spent 20 years shaping Tablet Hotels into a tech and luxury travel icon, culminating in its acquisition by the discerning Michelin Group 4 years ago. Now, Laurent is channeling his expertise and refined taste into launching a wine company committed to delivering the world’s finest...
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Keith Smith: Exited Founder + Single Dad Talks About Mental Health, Purpose & Creator Economy
Keith Smith has spent 2 decades building 5 companies and raising 2 children as a single dad. A deep and original thinker, he chose to confront his post-exit mental health issues head on. In this episode, Keith openly shares his insights, therapy takeaways and how he found his latest mission in...
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Connor Tomkies: Aftermath of an Exit: Healing, Reflecting, and Progressing Forward
Connor Tomkies. He spent 8 years growing and selling SupportNinja, his global talent acquisition firm. Now he focuses on buying great businesses to scale them for exit. This episode delves into Connor’s exit experience, why he prefers to buy a significant portion of a business over angel…
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Sriram Gollapalli: Exited Tech Founder Who Loves Investing
Sriram Gollapalli. After selling his software as a service business 8 years ago, he spent 6 years working with an acquirer before embracing his new found freedom. His calling? Investing and fostering a community of like minded investors. This episode delves into Sriram’s post exit journey....
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Ari Katz. Exited Founder: Why Psychedelics as My New Venture
Ari Katz teamed up with his celebrity doctor wife to create and sell one of the largest dermatology chains in the US. The exit afforded him the time and resources to explore his longstanding obsession with mental health. Ari’s new purpose? To revolutionize mental health care by advancing the...
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Matt Matros: Battling Demons and Building Post-Exit Dreams
Matt Matros. After selling his healthy-food chain 10 years ago, Matt battled depression, anxiety, regret, and alcohol addiction. Yet, he didn't stop. He built and sold two more businesses, started a family, traveled the world, and became a highly respected voice in the business world. How did he...
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Nick Telson-Sillett: Angel Investing, Being Creative and Getting Wiser
Nick Telson-Sillett. He isn't just the famous host of "Pitch Deck," a go-to podcast for angel investing insights; he's a real-deal entrepreneur who, after selling his own company five years ago, decided to give back. Through Horseplay Ventures, he supports up-and-coming startups, and with his new...
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Dan Reich: After 4 Exits, I Have No Desire to Retire!
Dan Reich has sold 4 successful companies so far, but he's far from finished. Retirement isn't in his plans anytime soon. What drives his relentless hunger, creativity and energy? How does he find such clear direction so quickly after each exit? In this episode, Dan offers an insightful look into...
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Boris Berenberg: I Regret Selling My Business
Boris Berenberg. He thought he hit the jackpot selling his bootstrapped cash-rich software business. Two years later, he's filled with bitter regret. In this candid episode, Boris gets real about his exit—what he wishes he knew then and what we can all learn now. LinkedIn Boris:...
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Aaron White: Beyond the Exit: Sustaining the Serial Builder's Drive
Aaron White and Anastasia Koroleva unpack the fascinating interplay of art and obsession within entrepreneurship. They share practical insights about the artistic nature of entrepreneurial ventures, the role of obsession in driving success, and the challenge of maintaining a strong sense of...
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Bill Hudenko: Beyond the Exit: Insights from a Psychologist Turned Exited Founder
Bill Hudenko. A serial exited founder, clinical psychologist, university professor, self-taught programmer, and musician, Bill joins us today to share his personal and professional insights on life after an exit. Each of Bill's businesses, past and present, has been driven by a mission to heal...
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ABOUT THIS SHOW
I'm Anastasia Koroleva, a 4x exited founder exploring life after selling a business with some of the most remarkable post-exit entrepreneurs in the world. Together, we rediscover purpose, redefine success, master investing, and build fulfilling lives and families.Having survived a 9-digit exit, I dedicated a decade to researching the deepest challenges faced by entrepreneurs after a business sale. This podcast is the platform to share my and other exited founders' hard-earned wisdom with the world.To join our community, please subscribe and share your thoughts. I’d love to hear from you 🙏.
HOSTED BY
Anastasia Koroleva
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Frequently Asked Questions
How many episodes does Exit Paradox have?
Exit Paradox currently has 60 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Exit Paradox about?
I'm Anastasia Koroleva, a 4x exited founder exploring life after selling a business with some of the most remarkable post-exit entrepreneurs in the world. Together, we rediscover purpose, redefine success, master investing, and build fulfilling lives and families.Having survived a 9-digit exit, I...
How often does Exit Paradox release new episodes?
Exit Paradox has 60 episodes. Check the episode list to see recent publication dates and frequency.
Where can I listen to Exit Paradox?
You can listen to Exit Paradox on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Exit Paradox?
Exit Paradox is created and hosted by Anastasia Koroleva.
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