Exit Paradox

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 bank Drake Star Partners, leveraging his earlier investment banking experience in NYC.  Balancing life...

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 Tony to reassess his priorities. Now he's an advocate for healthy living, an Ironman athlete and is fin...

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 Lessons: How I Conquered the Business of Partying with Tech. In this episode, Shane reveals the secrets...

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 discuss his hard-earned lessons on happiness, why he started his fourth business now and walked away from run...

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 he envies those still in the rat race, how he earns his sleep, finds purpose and talks to his kids ab...

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 soul search, secrets to post -exit happiness, the impact of the sale on his young family, and the excit...

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 journey.  In this episode, Preston shares how he learned to appreciate what he had, communicate more vul...

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 post-exit identity crisis, building a personal brand, dealing with celebrities and becoming an investor. ...

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 selling investment-grade art.  In this episode, Craig shares how and why he found his post-exit mission in...

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 finding true self, sovereignty, and inexhaustible fuel sources. Connect with Dave: Website: https://w...

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 competence, release control, and master the art of letting go. ________________________________________________...

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 it—he avoids any money-making activities, focusing instead on activities that increase his energy.  In...

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 wines at fair prices.  In this episode, we explore the art of building luxury brands, quality obsessi...

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 empowering creators with his innovative AI tools. _____________________________________________________...

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 investing, and how helping out his extended family members turned out to be the most rewarding use of his exit...

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. Including an introspection retreat, angel investing and the challenges of estate planning. __________________...

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 psychedelic medicine movement. In this inspirational episode, Ari opens up about his journey from business...

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 overcome his struggles? With his signature humor and crystal-clear insight, Matt opens his heart to sha...

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 software company, Trumpet, he's still in the game. Eloquent and open-hearted, Nick's here to share wit...

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 his journey, sharing his practical wisdom in an honest and straightforward manner. ___________________...

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: https://www.linkedin.com/in/borisberenberg/ Blog Boris: https://www.nothingeasyaboutthis.com/i-regret-selling-my-startup...

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 identity even after achieving success. Aaron and Anastasia delve deep into the concept of entrepreneurship b...

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 others, rooted in a deep understanding of the human psyche. He is an incredibly warm, caring, and captiva...

Brett Gelfand. A second-generation exited founder, he has successfully built and sold a company, just like his dad. Now, they're in business together. In this episode, Brett shares with us insights from both his and his father's post-exit experiences, the keys to successful business partnerships, finding love, and thriving as a digital nomad. _____________________________________________________ T...

Timo Armoo is a post-exit prodigy, who sold his first business at the age of 17, then aced an 8-figure exit at 27. He’s a Forbes 30 Under 30 honoree, Huffington Post’s Entrepreneur of The Year, and one of The Times' most influential media figures. Beyond TV and book deals, he’s a magnetic speaker and the incredible friend who pushed me to launch this podcast. Timo’s here to inspire us with his no-...