Exit Paradox

Anastasia Koroleva
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Exit Paradox

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. 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
  2. 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
  3. 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
  4. 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
  5. 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?

    1h 9m
  6. 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
  7. 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
  8. Alex Macdonald. A $300M Exit is No Reason to Retire

    18 FEB

    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 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 company. He didn't want that to happen to him. I think honestly, if I had had that void, it probably would have not led to a productive use of my energy. I'm actually very happy that I had something immediately to jump into. And yeah, that's led to me not having to go through that challenging period that I see a lot of my friends go through, questioning their identity and everything. In this episode, we're going to explore why he made this decision, whether two years later he still feels it was the right one, and how he applies the lessons from his first full entrepreneurial cycle to building his new business, appropriately called SQL. 🚀 00:00:00 - Introduction 💼 00:02:25 - The Story of Velocity Black 🏦 00:07:46 - Selling Velocity Black to Capital One 🔥 00:07:05 - Why Alex Started Another Business Before Selling His First One 🧠 00:10:52 - The Founder’s Existential Crisis After an Exit 👷‍♂️ 00:12:45 - The Shortage of Builders, Not Investors 💪 00:14:19 - Work-Life Balance & Health After an Exit 📊 00:16:21 - Lessons from Running a 24/7 Business ⚖️ 00:19:52 - Changing Approach to Work with Sequel 🕵️‍♂️ 00:21:19 - Different Approaches to Post-Exit Businesses 🏛️ 00:24:19 - Sequel: Building a Next-Gen Goldman Sachs 🏁 00:27:26 - Managing Motivation After Financial Success 🔑 00:31:03 - Fulfillment vs. Happiness: What Really Matters? 🩺 00:33:15 - The Biohacking & Longevity Obsession 🤝 00:35:51 - Community & Meaning in Life After an Exit 🙏 00:39:13 - The Idea of Creating a New Religion 📜 00:45:46 - The Role of Structure & Responsibility in Life. 🔓 00:54:08 - The Challenge of Freedom After an Exit 📈 00:57:46 - Angel Investing & How It Led to Sequel 🎯 01:03:42 - Helping Athletes Transition Beyond Their Careers 💰 01:07:37 - Building a Legacy vs. Just Making Money ⚠️ 01:10:52 - Avoiding Mistakes in Early-Stage Investing 📢 01:15:30 - The Power of Influence in Investing 🚀 01:20:05 - Sequel’s Future Plans & Scaling the Model 🏆 01:25:00 - What Drives Long-Term Success? 🛑 01:30:10 - Final Thoughts & Advice for Founders

    1h 35m
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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
    54
  • Rating
    Explicit
  • Copyright
    © Anastasia Koroleva
  • Show Website
    Exit Paradox

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