Exit Paradox

Oct 31 2024 41 ep. 65 mins 6

Exit Paradox Podcast artwork

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 🙏.

Copy RSS

Subscribe on Podcast Addict

Roy Rubin. Magento’s Exited Founder: Globetrotting and the Search for Purpose

Oct 31 2024 83 mins

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

Brock Weatherup. Secrets of Successful Sequels

Oct 22 2024 67 mins

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,

Scott Wolfe. After $500M Exit: “My Vision Is Forever Unfinished"

Oct 15 2024 79 mins

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 t

Johnathan. 'Life Forced a New Purpose on Me'

Oct 08 2024 48 mins

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

Jason Kirby. From Exit to Ease: Letting Go of the Stress

Sep 06 2024 56 mins

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.

Matthew Johnson. Prolific Exited Entrepreneur on Work-Life Balance

Aug 30 2024 69 mins

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

Bill Flagg. 5 Exits Later: Pursuit of Inspiration

Aug 20 2024 32 mins

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, Bill moved with his family from Colorado to Portugal with no plans of returning any

Tony Kula. Post-Exit Shift: From Workaholic to Ironman

Aug 14 2024 36 mins

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 Iro

Shane Neman. Secrets of Post-Exit Happiness

Aug 07 2024 57 mins

Shane Neman. He 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, Sha

Ben White. 'Dark Decade' After $800M Exit: Addiction. Divorce & Financial Losses

Jul 31 2024 67 mins

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 no