Exit Paradox

Anastasia Koroleva
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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, and build fulfilling lives and families. My mission? To inspire exited founders to wield their unique blend of experience, time, wealth, and community power for a profound global impact. 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 🙏.

  1. Dan Berger. $100M Exit, Sex Addiction, and the Fight to Belong

    21 JULY

    Dan Berger. $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 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 pleasure they gave him was too fleeting, too empty. It did nothing to meet his real needs. That's when Den realized that his Exit wasn't just a big win. It was a chance to create something he'd never truly had. Real sense of belonging. Today, years later, he finally has it. He has finally built it. Then is a story of real courage. The courage to confront his darkest demons. Childhood trauma, bipolar disorder, Chronic anxiety. The patience and resilience to get to the root of his pain. This is one story you really don't want to miss. _____________________________________________________ 00:00:00 Intro 00:01:55 Life After Selling Social Tables 00:02:25 Loss of Belonging Post-Exit 00:03:53 Failed Attempts to Recreate Work Identity 00:05:05 Belonging & Addiction 00:06:42 Why He Wasn’t Aware of His Needs 00:09:43 The Crossroads Moment and Reinventing Identity 00:13:23 Dan’s Framework for Belonging 00:18:10 Can Our Belonging Archetype Change? 00:22:43 Dan’s Belonging Tank Today 00:25:02 How Dan Defines Belonging 00:32:01 Sex Addiction and Its Roots in Belonging 00:36:22 Getting Help: 12-Step Recovery 00:37:54 Why No One Talks About Sex Addiction 00:39:44 Loneliness, Belonging & the Male Crisis 00:42:52 Raising Boys and Masculinity Today 00:45:14 Switching Gears: The Financial Impact of Exit 00:48:49 Die With Zero: A New Financial Philosophy 00:53:23 Purpose, Not Just Experience 00:56:00 New Venture: Offsite Retreat Venues 00:57:38 Lessons from Social Tables to New Business 00:59:12 Dan’s Business Archetype: Operator 01:00:12 The Risks of Using Own Money 01:01:19 Writing a Book: Process and Pitfalls 01:03:20 What's Special About Dan's Book 01:04:07 How Dan Wants to Be Remembered

    1h 5m
  2. Amy Castoro. Wealth vs Family: An Expert’s View

    1 MAY

    Amy Castoro. 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 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 well. We talk about raising children with money and how to rethink our own relationship with it after a successful exit. It’s one of the most useful conversations I’ve had. Amy’s views challenged my own. I hope it helps you as much as it helped me.

    1h 15m
  3. Jay Radia. Venture Studio as a Post-Exit Path

    22 APR

    Jay Radia. 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 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 studio not just for financial success—but for joy, purpose, and meaning. And what he’s learned from both his own journey and the many post-exit founders he works with.

    1h 20m
  4. Linda Abraham. 2 Exits + 4 Kids = 1 Incredible Woman

    15 APR

    Linda Abraham. 2 Exits + 4 Kids = 1 Incredible Woman

    Linda 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 companies, and serves on several boards, including Tiger 21. But what blows me away most is that she built all of this while raising four children—and thoughtfully nurturing deep, loving relationships with each of them. This episode is about an extraordinary entrepreneur who managed to do it all—and built a life that’s not just financially successful, but deeply, holistically fulfilling. There is so much we can all learn from her!

    1h 1m
  5. Adam Rossi. How to Build, Exit, and Stay Married

    24 MAR

    Adam Rossi. 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 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 through it. We talk about what Adam would do differently now that he's had 14 years to reflect. Adam's story is fascinating and full of hard won wisdom. I'm so grateful he shared it.

    1h 11m
  6. Mike Brown. Post-Exit: From Chaos to Clarity

    16 MAR

    Mike Brown. 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. 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 🐦 X (Twitter) - ⁠https://x.com/mbrown_co⁠ 📸 Instagram - @mbrown.co 💻 Website - ⁠https://unbreakablewealth.com/⁠ 👥 Linkedin - ⁠  /mikebrownactual  ⁠

    1h 9m
  7. Kass and Michael Lazerow. $800M Exit: “Shoveling Shit” in Business and Marriage

    3 MAR

    Kass and Michael Lazerow. $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 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 - Introduction 00:00:14 - Learning from Failure vs. Success 00:00:27 - Building a Business as a Married Couple 00:01:08 - First Meeting and Early Impressions 00:02:30 - Life After an Exit 00:03:08 - Golf.com: The First Big Exit 00:06:58 - The Struggles of Entrepreneurship 00:09:14 - The Emotional Toll of Entrepreneurship 00:10:35 - Taking a Break After an Exit 00:11:14 - Was Their First Exit Life-Changing? 00:12:54 - Why Start Another Business? 00:14:31 - Entrepreneurship with Three Kids 00:16:47 - Why Entrepreneurs Keep Going 00:19:41 - Becoming Investors 00:23:20 - The Hardships Behind Entrepreneurship 00:28:17 - Coping with Post-Exit Stress 00:31:41 - Entrepreneurs and Mental Health 00:34:55 - Reframing Anxiety & ADHD as Superpowers 00:38:46 - The Dark Side of Entrepreneurship 00:44:01 - Work-Life Balance: Do They Have One? 00:48:01 - Michael’s Attempt at a Painting Career 00:50:12 - Filtering Opportunities 00:52:28 - Navigating Marriage After an Exit 00:55:15 - Raising Kids with Wealth 01:02:11 - Teaching Kids About Money and Responsibility 01:09:04 - The Purpose of Their Book 01:11:20 - Final Question: How Do You Want to Be Remembered? 🔗 CONNECT WITH KASS AND MIKE: 👥 Linkedin KASS - https://www.linkedin.com/in/kasslazerow/ 🐦 X (Twitter) KASS - https://x.com/kasslazerow 👥 Linkedin MIKE - https://www.linkedin.com/in/lazerow/ 🐦 X (Twitter) MIKE - https://x.com/lazerow 💻 Website (personal) - https://www.kassandmike.com/ I📸 Instagram: https://www.instagram.com/kassandmike/ TikTok: https://www.tiktok.com/@UCgLzz0yep6lUaE5i62zMXTw 🎥 YouTube Channel: https://www.youtube.com/@UCgLzz0yep6lUaE5i62zMXTw 🔗 CONNECT WITH ANASTASIA: 🎥 YouTube Channel - https://www.youtube.com/@UCaoC4W9E2Vopnkd-K3dOw7Q t 🐦 X (Twitter) - https://x.com/AnasKoroleva 📸 Instagram - https://www.instagram.com/anastasiashoot 💻 Website - https://www.exitparadox.com 🗞️ Newsletter - https://www.exitparadox.com/blog 👥 Linkedin - https://www.linkedin.com/in/anastasiakoroleva TikTok - https://www.tiktok.com/@anastasia.korolev7

    1h 13m
  8. Josh Payne. From $100M Exit to Fulfillment: Josh Payne’s Playbook

    27 FEB

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

    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 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 something bigger. So let’s see what we can learn from this fascinating man.

    55 min
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Hosts & Guests

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, and build fulfilling lives and families. My mission? To inspire exited founders to wield their unique blend of experience, time, wealth, and community power for a profound global impact. 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 🙏.

Information

  • Creator
    Anastasia Koroleva
  • Years Active
    2023 - 2025
  • Episodes
    55
  • Rating
    Explicit
  • Copyright
    © Anastasia Koroleva
  • Show Website
    Exit Paradox

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