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. Daniel Kivatinos. Post-Exit: Why I Am Building Again

    NOV 14

    Daniel Kivatinos. Post-Exit: Why I Am Building Again

    On this podcast we've explored many dramatic post exit stories. Tales of existential crisis, addictions to drugs, alcohol, sex and obsessive money chasing, extreme sports, mind blowing adventures and long spiritual journeys to faraway lands. Daniel Kvatinos journey is different and just as important to hear. His pause after selling his company didn't push him into a new path. It gave him clarity that he was already on the right one. Daniel built and sold DrChrono, one of the first mobile medical platforms processing billions in medical billing. His work even took him to the White House to help shape healthcare data policy. Today, Daniel is building JustPaid, an AI powered platform changing how businesses manage accounts receivable. In our conversation, Daniel shows us how he built that conviction about who he is and what he truly wants to do. In his case, to keep building highly impactful tech companies right in the heart Of Silicon Valley. _____________________________________________________ TIME STAMPS: 00:00 – Fulfilment: “Some days I’m a five, some days a six” 00:19 – What would it take to feel like a 10? 00:58 – The illusion of a “perfect place” in life 01:17 – Mountain after mountain: why satisfaction always moves 01:37 – Introducing Daniel Kivatinos & his journey from DrChrono to JustPaid 02:14 – Can a life ever feel fully “satisfied”? 03:11 – Starting the conversation: Daniel joins the show 03:17 – How he discovered the podcast & why it resonated 03:36 – He sold DrChrono… and then started a new company within a year 04:05 – Why founders can’t take long breaks without losing their edge 05:40 – Did one year off give enough space for clarity? (Short answer: no.) 06:21 – Why entrepreneurs struggle with taking real time off 07:57 – The addictive nature of building companies 08:40 – Is the second company easier? (Spoiler: no, just “different hard.”) 10:10 – Is it ever easier the second time? Unrealistic expectations 10:43 – “You can’t hire people to build it for you” 11:40 – Even Steve Jobs struggled with his second company 13:07 – Why second-time founders often fail 14:33 – What Next actually gave Steve Jobs later 15:19 – Connecting the dots only works backward 15:44 – What Daniel did during his year off 16:40 – The Reddit founder told him to move to California 17:22 – Early Y Combinator days & why he never returned to NYC 17:39 – Considering moving away after the exit 18:01 – Missing family and exploring other states 23:15 – “What should I do with a year off?” His advice 23:59 – Driving across the U.S. twice — unstructured freedom 25:05 – The joy of having no plan 26:25 – Driving across the Great Salt Lake (the slightly risky part) 27:11 – Why unstructured time matters after a big exit 27:31 – Realizing he wasn’t “done” with tech or Silicon Valley 27:57 – Three years later: is he happy? 28:07 – Business as a game, not just work 29:32 – Creator vs operator: early-stage founders must be both 33:58 – Modeling meaning and fulfilment for children 36:08 – Why he became an entrepreneur in the first place 36:14 – Graduating into the 2008 crisis 36:40 – Discovering startup life and loving the creative chaos 38:23 – It wasn’t about money — it was about people 40:49 – Two failed startups in a row: learning without financial reward 41:11 – Motivation after exit: still driven by curiosity, not fear or money 42:13 – Curiosity as the true engine behind building companies 43:17 – Why no single motivator is enough to build a company 45:01 – “Stay hungry, stay foolish” — Daniel’s interpretation 46:36 – Work-life balance vs. work-life integration 48:40 – Why remote culture supports family life 49:26 – How much he actually works 49:35 – Comparing work intensity: first company vs second 50:16 – Why he set up the company so co-founders push each other 51:00 – The mountain metaphor: why fulfilment never stays 52:07 – What a “10 day” looks like for Daniel 53:42 – Finding joy in the small things 57:13 – Closing reflections & farewell

    58 min
  2. Justin Donald: The Post‑Wealth Work‑Life Balance

    OCT 30

    Justin Donald: The Post‑Wealth Work‑Life Balance

    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 it doesn't have to be a choice and fulfillment can live side by side. Today he shares his story, his hard earned insights and the way he's chosen to live his own life. _____________________________________________________ TIME STAMPS: 00:00 – The shift from “have to work” to “get to work” 00:20 – Anastasia introduces Justin Donald and the idea of ambition vs fulfilment after exit 01:12 – Why work when you don’t have to? Finding meaning and fulfilment 02:17 – Introduction and greetings 03:10 – Justin’s early beginnings and first entrepreneurial experiences 04:25 – The gift of learning self-reliance 04:44 – From door-to-door sales to early business ventures 07:33 – First exits and lessons from building and selling small companies 09:21 – Transition from trading time for money to investing for freedom 09:31 – Defining financial freedom before becoming a millionaire 13:03 – Writing The Lifestyle Investor — from passion project to bestseller 14:10 – Donating profits to fight human trafficking and the book’s viral success 16:10 – Building the Lifestyle Investor community and its strict values 16:27 – Launching programs for young adults and future investors 16:35 – What financial freedom really means 18:58 – The balance between hard work and fulfilment 19:31 – Justin’s year-long sabbatical — lessons from doing “nothing” 23:17 – The true luxury: working because you want to 23:38 – Building life around values — faith, family, health and business 26:38 – Managing time and boundaries: the schedule that reflects priorities 27:36 – Breaking free from the rat race and the myth of “more money” 30:40 – The power of asking higher quality questions 32:50 – The exited founder’s dilemma: work or retire? 33:40 – Why taking time off after exit is essential 36:05 – Knowing when not to rush into what’s next 37:27 – Retirement vs sabbatical: doing things in the right sequence 38:35 – The fallacy of retirement — why people need purpose 40:00 – Pivoting from “have to work” to “get to work” 41:20 – Reinvention and second acts: From Strength to Strength 42:57 – Learning new skills after success — and why “ikigai” isn’t always right 44:02 – Staying a student: the joy of being a beginner again 45:06 – Teaching as the most fulfilling next chapter 46:20 – The story of Justin’s aptitude test and rediscovering his destiny to teach 50:51 – Purpose and profit: resolving the moral tension 51:14 – Why wealth creation and impact can coexist 54:24 – Giving, purpose, and the meaning of fulfilment 55:11 – Teaching financial wisdom to his daughter 57:33 – Legacy: how Justin wants to be remembered 58:25 – Closing thoughts and invitation to Lifestyle Investor community 59:32 – Where to find Justin online

    1 hr
  3. 5,000+ Post-Exit Founders: What Actually Works with Barak Kaufman

    SEP 25

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

    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.

    1h 20m
  4. Dan Berger. $100M Exit, Sex Addiction, and the Fight to Belong

    JUL 21

    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
  5. Amy Castoro. Wealth vs Family: An Expert’s View

    MAY 1

    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
  6. Jay Radia. Venture Studio as a Post-Exit Path

    APR 22

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

    APR 15

    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
  8. Adam Rossi. How to Build, Exit, and Stay Married

    MAR 24

    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
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Hosts & Guests

4
out of 5
60 Ratings

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
    58
  • Rating
    Explicit
  • Copyright
    © Anastasia Koroleva
  • Show Website
    Exit Paradox

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