Podcast
Exit Paradox
Hosted by Anastasia Koroleva · EN
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 🙏.
10episodes
Episodes
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Post-Wealth Expert: How To Re-ignite Drive and Energy After Financial Success
Feb 1101:12:47Tap to summarizeMost people believe that once you achieve financial freedom, life becomes lighter, calmer, and more fulfilling.But what if wealth quietly destroys your drive, energy, and sense of aliveness?In this private webinar, Anastasia Koroleva, founder of Exit Paradox, reveals a powerful and deeply counterintuitive pattern she has observed in founders and CEOs after major exits — a state she calls post-wealth apathy.After wealth, we optimise our lives for time and energy. We remove discomfort. We avoid stress. We follow what “feels good.”Yet 10–20 years later, many high achievers find themselves living lives that are comfortable - but flat.Low drive. Low energy. Low pull toward anything extraordinary.In this webinar, Anastasia explains why the dominant post-wealth philosophy fails — and introduces the Worthy Challenge Framework, a science-grounded approach used by true post-wealth sages to stay peaceful yet energized, calm yet fully alive, without burning out.This conversation is essential viewing for founders, CEOs, investors, and high performers navigating identity, purpose, and motivation after success.In this episode, you’ll discover:◼️ Why optimising for comfort after wealth leads to low dopamine and chronic apathy◼️ The hidden biochemical reason drive disappears post-exit◼️ Why “following your energy” often keeps you stuck and disengaged◼️ The difference between time & energy optimisation vs worthy challenge living◼️ How post-wealth sages stay deeply fulfilled without sacrificing peace◼️ The framework that reignites sustainable motivation after financial freedom◼️ Why most founders wait too long — and then never re-engage fully with lifeIf this conversation resonates, please share it with someone navigating life after an exit.These ideas can quietly change the trajectory of an entire life.
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Omar Haroun: “Outsized Impact is Incredibly Rewarding”
Jan 801:00:55Tap to summarizeIn this conversation, serial entrepreneur and exited founder Omar Haroun reveals the hidden emotional cost of success, the identity collapse many founders experience post-exit, and why wealth alone often fails to deliver fulfillment.Omar is a multi-exit entrepreneur and investor who has spent years studying the psychological and emotional realities of life after selling a business.He reflects on the philosophy of life after success: how wealth gives safety but not security, why progress is really about trading old questions for better ones, and how many exited founders quietly waste their freedom by staying comfortable.We explore:• The moral responsibility that comes with capability• Why regret is a better compass than ambition• How founders get stuck using old success models in a new life• Why contribution, not accumulation, becomes the real measure
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The Wealth Lag: What Happens AFTER Financial Freedom
Dec 900:14:30Tap to summarizeAfter selling her bootstrapped company in a 9-figure all-cash exit, Anastasia Koroleva expected freedom, joy, and the end of struggle.Instead, she encountered something no one talks about—the Wealth Lag.In this deeply honest and research-backed breakdown, Anastasia reveals the emotional crash that happens after financial freedom: the confusion, cognitive dissonance, identity loss, and the quiet dissatisfaction that haunts even the most successful founders, investors, athletes, and creators.For 15 years she's studied hundreds of post-exit lives, and today he shares the patterns, tools, and stages that determine whether wealth becomes leverage for a deeply fulfilling life… or a trap that slowly suffocates us.This episode is for anyone who has created wealth, is on the path to it, or wants to understand the psychological reality behind “success”.Anastasia explains:◼️ What the Wealth Lag really is — and why it hits every rich founder◼️ Why the brain rebels against sudden wealth (cognitive dissonance explained)◼️ How comfort becomes a silent addiction that drains purpose and identity◼️ The 5 stages people must move through to adapt to wealth◼️ Why most wealthy people stay stuck for decades◼️ The emotional, intellectual, and spiritual work required after an exit◼️ How to build a tribe that accelerates growth instead of stagnation◼️ Why financial freedom does NOT create fulfillment — and what doesThis is the real conversation that elite founders, ex-CEOs, wealth creators, and next-gen inheritors have behind closed doors. Exit Paradox brings it into the light.If this episode helped you, please share it with someone who needs it.TIMESTAMPS00:00 – What Happens After Financial Freedom00:22 – The Hidden Problem No One Warns You About01:01 – The Wealth Honeymoon: Cars, Jets & New Toys01:43 – Why Wealth Eventually Stops Feeling Good02:15 – “Wealth Has Arrived… But I Haven’t”02:58 – The Wealth Lag: Why Your Inner World Falls Behind03:38 – Cognitive Dissonance: Your Brain’s Wealth Alarm System05:00 – Why Most People Never Adapt to Wealth06:39 – The Trap of Comfort (and How It Quietly Destroys Ambition)07:28 – Step 1: Reframing Wealth as Leverage, Not the Goal08:24 – Step 2: Building a Fulfilling Life Strategy Post-Exit09:50 – Step 3: The Skills You Need After You Get Rich10:42 – Step 4: Building a Tribe That Pulls You Forward12:16 – Step 5: The Decision That Changes Everything13:24 – The Real Mission: Clarity, Conviction & A Life Worth Living
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Daniel Kivatinos Post-Exit: Why I Am Building Again
Nov 2100:57:55Tap to summarizeOn 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 Kivatinos 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 life01:17 – Mountain after mountain: why satisfaction always moves01:37 – Introducing Daniel Kivatinos & his journey from DrChrono to JustPaid02:14 – Can a life ever feel fully “satisfied”?03:11 – Starting the conversation: Daniel joins the show03:17 – How he discovered the podcast & why it resonated03:36 – He sold DrChrono… and then started a new company within a year04:05 – Why founders can’t take long breaks without losing their edge05:40 – Did one year off give enough space for clarity? (Short answer: no.)06:21 – Why entrepreneurs struggle with taking real time off07:57 – The addictive nature of building companies08:40 – Is the second company easier? (Spoiler: no, just “different hard.”)10:10 – Is it ever easier the second time? Unrealistic expectations10:43 – “You can’t hire people to build it for you”11:40 – Even Steve Jobs struggled with his second company13:07 – Why second-time founders often fail14:33 – What Next actually gave Steve Jobs later15:19 – Connecting the dots only works backward15:44 – What Daniel did during his year off16:40 – The Reddit founder told him to move to California17:22 – Early Y Combinator days & why he never returned to NYC17:39 – Considering moving away after the exit18:01 – Missing family and exploring other states23:15 – “What should I do with a year off?” His advice23:59 – Driving across the U.S. twice — unstructured freedom25:05 – The joy of having no plan26:25 – Driving across the Great Salt Lake (the slightly risky part)27:11 – Why unstructured time matters after a big exit27:31 – Realizing he wasn’t “done” with tech or Silicon Valley27:57 – Three years later: is he happy?28:07 – Business as a game, not just work29:32 – Creator vs operator: early-stage founders must be both32:41 – Did his son influence the decision to start another company?33:58 – Modeling meaning and fulfilment for children36:08 – Why he became an entrepreneur in the first place36:14 – Graduating into the 2008 crisis36:40 – Discovering startup life and loving the creative chaos38:23 – It wasn’t about money — it was about people40:49 – Two failed startups in a row: learning without financial reward41:11 – Motivation after exit: still driven by curiosity, not fear or money42:13 – Curiosity as the true engine behind building companies43:17 – Why no single motivator is enough to build a company45:01 – “Stay hungry, stay foolish” — Daniel’s interpretation46:36 – Work-life balance vs. work-life integration46:45 – How he designs balance in his second company48:40 – Why remote culture supports family life49:26 – How much he actually works49:35 – Comparing work intensity: first company vs second50:16 – Why he set up the company so co-founders push each other50:22 – Returning to fulfilment: the moving target51:00 – The mountain metaphor: why fulfilment never stays52:07 – What a “10 day” looks like for Daniel53:42 – Finding joy in the small things53:59 – Why the end goal will never create long-term fulfilment54:18 – “How do you want to be remembered?”54:29 – Family, impact, and acceptance56:16 – Graveyards, billionaires, and perspective on legacy57:13 – Closing reflections & farewell
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Justin Donald: The Post‑Wealth Work‑Life Balance
Oct 3001:00:18Tap to summarizeOne 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.
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5,000+ Post-Exit Founders: What Actually Works with Barak Kaufman
Sep 2601:20:30Tap to summarizeBarak 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: https://www.linkedin.com/in/anastasiakorolevaX: @AnasKorolevaNewsletter: https://www.exitparadox.com/blogAbout Anastasia: https://www.exitparadox.com/aboutListen to Exit Paradox Podcast:Apple Podcasts: https://podcasts.apple.com/us/podcast/exit-paradox/id1719806072Spotify: https://open.spotify.com/show/7cC1er82lJBviXe6qjM158
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$100M Exit, Sex Addiction, and the Fight to Belong
Jul 2201:04:49Tap to summarizeSome 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 Intro00:01:55 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
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Wealth vs Family: An Expert’s View
May 1, 202501:15:29Tap to summarizeToday’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.00:01:59 Amy’s Background & Work with the Williams Group00:03:30 Why 70% of Families Fail at Wealth Transition00:05:18 Trust, Communication & Heir Preparedness00:08:18 How Early Should Kids Be Taught About Wealth?00:10:31 Age-Appropriate Conversations About Philanthropy00:13:17 Creating Motivation Without Financial Desperation00:16:23 Responding to Kids Asking About Inheritance00:20:35 Involving Children in Wealth Management Early00:22:33 Teaching Kids to Say “No” & Handle Peer Pressure00:26:44 Skills Young Heirs Often Feel They Miss00:29:09 Should Children Be Encouraged to Be Entrepreneurs?00:32:28 What If the Family Came into Wealth Late?00:36:04 First Family Meeting: What to Discuss00:37:28 Re-engaging the “Unmotivated” Youngest Child00:40:29 Coaching vs. Therapy in Wealth Transition00:41:41 Families with Young Kids: How to Start Early00:44:33 Relationship Skills & Communication Patterns00:47:06 Why the Skills That Build Wealth Won’t Transition It00:48:20 Balancing Entrepreneurship & Parenting Post-Exit00:50:39 Modeling Purposeful Wealth, Not Just Growth00:54:36 What Successful Families Say the Purpose of Wealth Is00:56:49 Defining Family Values Around “Education”00:58:41 Reconciling Different Values in the Family00:59:50 Allowance Strategies in Wealthy Families01:01:38 Knowing When to Shift from Parent to Mentor01:03:28 Creating & Living a Family Mission Statement01:06:06 New Program: Next Gen Leaders01:07:25 Common Mistakes Families Make Around Wealth01:10:34 Should Families Hold Regular Meetings?01:12:37 The #1 Shift Families Must Make for Success01:13:38 Amy’s Recommended Books on Family Wealth01:15:15 Final Thoughts: Preparing the Family for the Assets
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Venture Studio as a Post-Exit Path
Apr 24, 202501:20:15Tap to summarizeMy 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._____________________________________________________00:00:00 - Introduction00:04:23 - Emotional journey post-exit00:06:00 - Experiencing emptiness despite success00:07:15 - Defining the Post-Exit journey (Pause, Reset, New Chapter)00:08:15 - Avoiding the corporate trap post-sale00:09:35 - Discovering he's not a CEO type00:10:15 - Founding Blissgrowth and love for early-stage building00:11:30 - Venture Studio vs Angel Investing and Accelerators00:13:15 - Pros and cons of running a Venture Studio00:15:15 - Team dynamics and focus of Blissgrowth00:16:45 - Common misconceptions about Venture Studios00:17:45 - How his studio compares to others00:19:15 - Angel investing vs Venture Studio involvement00:21:15 - Journey from emptiness to fulfillment00:23:15 - Connecting with intuition through stillness and yoga00:25:15 - Daily practices to cultivate inner clarity00:26:60 - The power of quiet and introspection00:28:15 - Rewiring mindset and deep inner work00:30:00 - Changing his relationship with fear00:31:30 - From fear to freedom and growth00:33:00 - The psychology of purpose and contribution00:34:15 - Observations on other exited founders and finding purpose00:35:45 - Why decoding purpose is a unique journey00:37:15 - Role of spirituality and Indian heritage in self-discovery00:39:45 - Spirituality as a path to love and connection00:41:15 - Overcoming skepticism and redefining success00:43:15 - AI, intellect, and spiritual work00:44:15 - Creating and renaming his podcast: Joyful Entrepreneur00:46:15 - Why he paused podcasting despite success00:47:45 - Lessons learned from podcasting00:49:15 - The power of public self-expression for exited founders00:50:45 - Normalizing post-exit struggles in the founder community00:52:15 - Redefining success after financial freedom00:53:45 - Jay’s 5-pillar framework for purpose00:55:45 - How Blissgrowth aligns with his purpose00:57:15 - Building to scale vs building to exit01:00:15 - Should founders build with an exit in mind?01:01:45 - Jay’s commitment to Blissgrowth long-term
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2 Exits + 4 Kids = 1 Incredible Woman
Apr 17, 202501:01:19Tap to summarizeLinda 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 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!00:00 - Introduction and reflections on Linda’s first business exit03:34 - Selling Peregrine Technologies and emotional response04:36 - Starting the next venture and skills assessment05:55 - Creating comScore and early funding story08:11 - Frugality and surviving the dot-com crash10:30 - Pivot to audience measurement and analytics11:36 - Selling data to financial institutions like Citadel11:59 - IPO and financial outcomes for the team13:00 - Motivations beyond money and public company growth14:01 - Leaving comScore and reflections on career satisfaction15:10 - Post-exit transition and board work17:09 - Realizing need for a break and pulling back from overcommitment18:19 - Shift to board advisory roles and family balance18:49 - Motherhood and managing with four children20:09 - Family-first values and support system21:48 - Daily decision-making and sacrifices24:49 - Health and lifestyle improvements post-exit27:25 - Transitioning from entrepreneur to investor29:01 - Challenges in board work and mindset shifts31:18 - Finding joy and variety in board roles33:42 - Investing in second-time founders and founder motivations38:15 - Raising children with wealth and aligned values40:50 - Reflections on adult children and family discussions43:07 - Delaying wealth conversations and individual approaches46:21 - Continuing involvement in husband’s new startup48:04 - Evolving motivations and contribution style49:42 - Creating balance through mindful time management52:45 - Focus on impact and strategic contribution56:12 - Mentorship, support, and satisfaction in giving back57:60 - Work, family, community: expanded arc of purpose59:58 - How Linda wants to be remembered01:01:14 - Conclusion and farewell
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