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PODCAST

Exit Paradox

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

business entrepreneurship

All Episodes

60:18

Justin Donald: The Post‑Wealth Work‑Life Balance

Exit Paradox ·

2025/10/30

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 dismiss the drive for more financial success once we've already had an exit. But Justin shows us

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80:30

5,000+ Post-Exit Founders: What Actually Works with...

Exit Paradox ·

2025/09/26

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-kaufmanPEF: https://pef.xyz/Vine Ventures: https://vineventures.comConnect with Anastasia: Linkedin:

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64:49

$100M Exit, Sex Addiction, and the Fight to Belong

Exit Paradox ·

2025/07/22

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. It made things worse. Den spiraled into addiction, sex and porn. But he soon realized the

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75:29

Wealth vs Family: An Expert’s View

Exit Paradox ·

2025/05/01

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, protect our closest relationships, speak openly, and prepare the next generation to handle wealth

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80:15

Venture Studio as a Post-Exit Path

Exit Paradox ·

2025/04/24

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 Podcast—a top 10 show about success and happiness.Today, we explore how Jay is designing his venture

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61:19

2 Exits + 4 Kids = 1 Incredible Woman

Exit Paradox ·

2025/04/17

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 countries.Today, Linda runs Crimson Capital, investing her family’s money in early-stage tech

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71:05

How to Build, Exit, and Stay Married

Exit Paradox ·

2025/03/26

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 marriage didn't just survive. Building and selling the business, it actually got stronger

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68:40

Post-Exit: From Chaos to Clarity

Exit Paradox ·

2025/03/18

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. Mike, I'd love you to walk me through step by step, what happened to you in those first few weeks after the exit? How you felt, how you thought?_______________🔗 CONNECT WITH MIKE:🎥 YouTube Channel - ‪@mbrown_co‬ 🐦

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72:34

$800M Exit: “Shoveling Shit” in Business and Marriage

Exit Paradox ·

2025/03/04

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 wish they hadn’t.TIME STAMPS:00:00:01 - Introduction00:00:14 - Learning from Failure vs

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55:17

From $100M Exit to Fulfilment: Josh Payne’s Playbook

Exit Paradox ·

2025/02/28

Welcome to Exit Paradox, where we explore what really happens after a successful business exit. I’m your host, Anastasia Koroleva.At some point post-exit, most of us ask the big question: How do I take care of my health, family, and wealth - without sacrificing my entrepreneurial ambitions? How do I build my next business without burnout?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

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95:00

Alex Macdonald. A $300M Exit is No Reason to Retire

Exit Paradox ·

2025/02/18

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 his post-exit founder friends getting stuck in full-blown existential crisis after they sold their

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100:38

Cory Janssen. 17 Years Post-Exit: Insights from...

Exit Paradox ·

2025/01/07

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 purpose he felt while building Investopedia. Everything changed when Cory went back to building

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108:21

Michael Miller. Meditation: the Ultimate Post-Exit...

Exit Paradox ·

2025/01/06

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. And it's not just me, people like Jack Dorsey, Bill Gates, Arianna Huffington, and Ray Dalio

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57:29

Sarah Douglass. Post-Wealth Search for Happiness

Exit Paradox ·

2024/12/03

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 disarming authenticity, opening up about her deepest struggles. We explore the unexpected void left

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47:15

Tim Schumacher. Sedo’s Exited Founder on Work-Life...

Exit Paradox ·

2024/11/20

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 face after a successful exit. In this episode, Tim shares his thoughts on keeping life

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89:44

Rick Eigenbrod. “Post-Exit Death is Inevitable”

Exit Paradox ·

2024/11/14

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, and how resisting these changes only adds to the struggle. Rick generously shares the tools and

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84:00

Roy Rubin. Magento’s Exited Founder: Globetrotting...

Exit Paradox ·

2024/10/31

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 journey around the world. For 14 months, they traveled without a plan, letting each destination

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67:40

Brock Weatherup. Secrets of Successful Sequels

Exit Paradox ·

2024/10/22

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 optimistic and gives him a sense of purpose, and how he cultivates relationships in both business

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79:58

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

Exit Paradox ·

2024/10/15

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 journey of building his business. Post-exit, he misses being driven by that vision and working

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48:06

Johnathan. 'Life Forced a New Purpose on Me'

Exit Paradox ·

2024/10/08

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 lengthy and confusing path for most—became clear and compelling after his family was hit by a

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57 results

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