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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 world.

To join our community, please subscribe and share your thoughts. I’d love to hear from you 🙏.

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#63
Saturday · 1 hr 9 min
Why Building Again Can Be Harder After Success | Eric Ries
Building a second company after a successful exit can look easier. You have experience, a network and financial freedom. But one of the forces that carried you through the first company may no longer be there: financial necessity. Eric Ries, author of The Lean Startup and Incorruptible, joins Anastasia Koroleva to examine what changes when founders build again after success. They discuss why the motivation that worked the first time can stop working, why experience does not automatically become useful learning, and why founders can leave a difficult exit with a story about what they personally did wrong without changing the structures that allowed it to happen. The conversation also gets into fear of failure, experimentation and first principles in Post-Exit life, what repeat founders fail to preserve from their earlier success, Eric's idea of “financial gravity,” why values eventually need structural protection, and how metrics can become false proxies for what we actually care about. Later, Eric and Anastasia discuss another question that becomes more relevant when work is optional: can we become more content without becoming less ambitious? And how do we distinguish genuine contribution from simply finding another form of status? Eric's book Incorruptible: incorruptible.co 0:00 - Opening 1:54 - How Lean Startup changed Anastasia's second company 4:24 - Eric Ries on what success actually means 8:10 - Selling a company, loss and the urge to build again 13:12 - Did successful founders really start only for money? 15:02 - Shareholder primacy and the builder's intuition 21:30 - Why fear of failure blocks experimentation 27:01 - Why experimentation still needs first principles 28:28 - Applying Lean Startup thinking to Post-Exit life 31:12 - What founders fail to learn from a painful exit 34:25 - Are repeat founders actually better? 37:58 - Saul Price, Costco and protecting what matters 42:56 - Eric's four dimensions of governance 48:45 - Vanity metrics and false proxies 51:33 - Writing and teaching after business success 52:20 - Equanimity without losing urgency 55:29 - Contribution or status farming? 1:01:20 - What actually drives Eric Ries 1:03:19 - The founder as conduit, not the whole system 1:07:48 - Eric's contrarian view on AI and human creativity
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#62
February 11 · 1 hr 12 min
Post-Wealth Expert: How To Re-ignite Drive and Energy After Financial Success
Most 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 life If 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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#61
January 8 · 1 hr
Omar Haroun: “Outsized Impact is Incredibly Rewarding”
In 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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#60
Dec 9, 2025 · 14 min
The Wealth Lag: What Happens AFTER Financial Freedom
After 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 does This 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. TIMESTAMPS 00:00 – What Happens After Financial Freedom 00:22 – The Hidden Problem No One Warns You About 01:01 – The Wealth Honeymoon: Cars, Jets & New Toys 01:43 – Why Wealth Eventually Stops Feeling Good 02:15 – “Wealth Has Arrived… But I Haven’t” 02:58 – The Wealth Lag: Why Your Inner World Falls Behind 03:38 – Cognitive Dissonance: Your Brain’s Wealth Alarm System 05:00 – Why Most People Never Adapt to Wealth 06:39 – The Trap of Comfort (and How It Quietly Destroys Ambition) 07:28 – Step 1: Reframing Wealth as Leverage, Not the Goal 08:24 – Step 2: Building a Fulfilling Life Strategy Post-Exit 09:50 – Step 3: The Skills You Need After You Get Rich 10:42 – Step 4: Building a Tribe That Pulls You Forward 12:16 – Step 5: The Decision That Changes Everything 13:24 – The Real Mission: Clarity, Conviction & A Life Worth Living
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#59
Nov 21, 2025 · 57 min
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 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 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 32:41 – Did his son influence the decision to start another company? 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 46:45 – How he designs balance in his second company 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 50:22 – Returning to fulfilment: the moving target 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 53:59 – Why the end goal will never create long-term fulfilment 54:18 – “How do you want to be remembered?” 54:29 – Family, impact, and acceptance 56:16 – Graveyards, billionaires, and perspective on legacy 57:13 – Closing reflections & farewell
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#58
Oct 30, 2025 · 1 hr
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.
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#57
Sep 26, 2025 · 1 hr 20 min
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. Connect with Barak: Linkedin: https://www.linkedin.com/in/barakk/ X: @barak-kaufman PEF: https://pef.xyz/ Vine Ventures: https://vineventures.com Connect with Anastasia: Linkedin: https://www.linkedin.com/in/anastasiakoroleva X: @AnasKoroleva Newsletter: https://www.exitparadox.com/blog About Anastasia: https://www.exitparadox.com/about Listen to Exit Paradox Podcast: Apple Podcasts: https://podcasts.apple.com/us/podcast/exit-paradox/id1719806072 Spotify: https://open.spotify.com/show/7cC1er82lJBviXe6qjM158
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#56
Jul 22, 2025 · 1 hr 4 min
$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
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#55
May 1, 2025 · 1 hr 15 min
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. 00:01:59 Amy’s Background & Work with the Williams Group 00:03:30 Why 70% of Families Fail at Wealth Transition 00:05:18 Trust, Communication & Heir Preparedness 00:08:18 How Early Should Kids Be Taught About Wealth? 00:10:31 Age-Appropriate Conversations About Philanthropy 00:13:17 Creating Motivation Without Financial Desperation 00:16:23 Responding to Kids Asking About Inheritance 00:20:35 Involving Children in Wealth Management Early 00:22:33 Teaching Kids to Say “No” & Handle Peer Pressure 00:26:44 Skills Young Heirs Often Feel They Miss 00:29:09 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 Discuss 00:37:28 Re-engaging the “Unmotivated” Youngest Child 00:40:29 Coaching vs. Therapy in Wealth Transition 00:41:41 Families with Young Kids: How to Start Early 00:44:33 Relationship Skills & Communication Patterns 00:47:06 Why the Skills That Build Wealth Won’t Transition It 00:48:20 Balancing Entrepreneurship & Parenting Post-Exit 00:50:39 Modeling Purposeful Wealth, Not Just Growth 00:54:36 What Successful Families Say the Purpose of Wealth Is 00:56:49 Defining Family Values Around “Education” 00:58:41 Reconciling Different Values in the Family 00:59:50 Allowance Strategies in Wealthy Families 01:01:38 Knowing When to Shift from Parent to Mentor 01:03:28 Creating & Living a Family Mission Statement 01:06:06 New Program: Next Gen Leaders 01:07:25 Common Mistakes Families Make Around Wealth 01:10:34 Should Families Hold Regular Meetings? 01:12:37 The #1 Shift Families Must Make for Success 01:13:38 Amy’s Recommended Books on Family Wealth 01:15:15 Final Thoughts: Preparing the Family for the Assets
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#54
Apr 24, 2025 · 1 hr 20 min
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. _____________________________________________________ 00:00:00 - Introduction 00:04:23 - Emotional journey post-exit 00:06:00 - Experiencing emptiness despite success 00:07:15 - Defining the Post-Exit journey (Pause, Reset, New Chapter) 00:08:15 - Avoiding the corporate trap post-sale 00:09:35 - Discovering he's not a CEO type 00:10:15 - Founding Blissgrowth and love for early-stage building 00:11:30 - Venture Studio vs Angel Investing and Accelerators 00:13:15 - Pros and cons of running a Venture Studio 00:15:15 - Team dynamics and focus of Blissgrowth 00:16:45 - Common misconceptions about Venture Studios 00:17:45 - How his studio compares to others 00:19:15 - Angel investing vs Venture Studio involvement 00:21:15 - Journey from emptiness to fulfillment 00:23:15 - Connecting with intuition through stillness and yoga 00:25:15 - Daily practices to cultivate inner clarity 00:26:60 - The power of quiet and introspection 00:28:15 - Rewiring mindset and deep inner work 00:30:00 - Changing his relationship with fear 00:31:30 - From fear to freedom and growth 00:33:00 - The psychology of purpose and contribution 00:34:15 - Observations on other exited founders and finding purpose 00:35:45 - Why decoding purpose is a unique journey 00:37:15 - Role of spirituality and Indian heritage in self-discovery 00:39:45 - Spirituality as a path to love and connection 00:41:15 - Overcoming skepticism and redefining success 00:43:15 - AI, intellect, and spiritual work 00:44:15 - Creating and renaming his podcast: Joyful Entrepreneur 00:46:15 - Why he paused podcasting despite success 00:47:45 - Lessons learned from podcasting 00:49:15 - The power of public self-expression for exited founders 00:50:45 - Normalizing post-exit struggles in the founder community 00:52:15 - Redefining success after financial freedom 00:53:45 - Jay’s 5-pillar framework for purpose 00:55:45 - How Blissgrowth aligns with his purpose 00:57:15 - Building to scale vs building to exit 01:00:15 - Should founders build with an exit in mind? 01:01:45 - Jay’s commitment to Blissgrowth long-term
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#53
Apr 17, 2025 · 1 hr 1 min
2 Exits + 4 Kids = 1 Incredible Woman
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 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 exit 03:34 - Selling Peregrine Technologies and emotional response 04:36 - Starting the next venture and skills assessment 05:55 - Creating comScore and early funding story 08:11 - Frugality and surviving the dot-com crash 10:30 - Pivot to audience measurement and analytics 11:36 - Selling data to financial institutions like Citadel 11:59 - IPO and financial outcomes for the team 13:00 - Motivations beyond money and public company growth 14:01 - Leaving comScore and reflections on career satisfaction 15:10 - Post-exit transition and board work 17:09 - Realizing need for a break and pulling back from overcommitment 18:19 - Shift to board advisory roles and family balance 18:49 - Motherhood and managing with four children 20:09 - Family-first values and support system 21:48 - Daily decision-making and sacrifices 24:49 - Health and lifestyle improvements post-exit 27:25 - Transitioning from entrepreneur to investor 29:01 - Challenges in board work and mindset shifts 31:18 - Finding joy and variety in board roles 33:42 - Investing in second-time founders and founder motivations 38:15 - Raising children with wealth and aligned values 40:50 - Reflections on adult children and family discussions 43:07 - Delaying wealth conversations and individual approaches 46:21 - Continuing involvement in husband’s new startup 48:04 - Evolving motivations and contribution style 49:42 - Creating balance through mindful time management 52:45 - Focus on impact and strategic contribution 56:12 - Mentorship, support, and satisfaction in giving back 57:60 - Work, family, community: expanded arc of purpose 59:58 - How Linda wants to be remembered 01:01:14 - Conclusion and farewell
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#52
Mar 26, 2025 · 1 hr 11 min
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. 00:00:00 – Introduction & Adam’s Exit Story 00:01:06 – Why Exited Founders Make Bad Investors 00:05:15 – From Angel Investing to Private Equity 00:09:00 – Why Most Second Companies Fail 00:10:15 – Lessons from a Failed Acquisition 00:12:07 – Buying vs. Building a Business 00:14:34 – Regret After Exit and Finding New Purpose 00:17:27 – Sacrifice, Purpose & The Next Big Thing 00:20:18 – Impact, Meaning & Philanthropy Struggles 00:23:44 – Coaching Entrepreneurs as a Calling 00:25:18 – Why He Hasn’t Jumped into a Big Mission Yet 00:27:00 – Kids, Family, and Timing the Next Move 00:29:00 – Angel Investing: Rise and Decline 00:31:06 – The Illusion of Control in Angel Investing 00:32:35 – Advice for New Angel Investors 00:34:45 – Lifestyle Balance Post-Exit 00:36:00 – The Grind Years: 20-Hour Days and Stress 00:38:00 – Building a Business with His Wife 00:41:30 – Division of Labor and Complementary Skills 00:43:00 – Conflict Resolution in a Husband-Wife Team 00:44:45 – Why They Didn't Start a Second Business Together 00:46:15 – Raising Entrepreneurial Kids with Wealth 00:50:45 – The Only Real Passive Investing Strategy 00:53:26 – Life Rules: Wealth vs. Freedom 00:56:40 – Is Balance Between Mission and Freedom Possible? 00:58:45 – Mental Health After the Exit 01:01:00 – Why He Shares His Story Publicly 01:03:15 – A Book for His Kids and Maybe the World 01:07:17 – Will He Publish It? 01:09:41 – How Adam Wants to Be Remembered 01:10:36 – Closing Thanks & Final Reflections
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#51
Mar 18, 2025 · 1 hr 8 min
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. 🔗 CONNECT WITH MIKE: 🎥 YouTube Channel - ‪@mbrown_co‬ 🐦 X (Twitter) - https://x.com/mbrown_co 📸 Instagram - @mbrown.co 💻 Website - https://unbreakablewealth.com/👥 Linkedin - /mikebrownactual TIME STAMPS: 00:00:00 – Introduction 00:00:37 – The Aftermath of Selling a Business 00:02:07 – Reality Hits: The Post-Exit Crisis 00:03:19 – The Connection Between Entrepreneurship and Divorce 00:05:00 – Chasing Achievement vs. Finding Purpose 00:06:40 – Could He Have Saved His Marriage? 00:08:33 – What’s Next After the Exit? 00:09:59 – Why Coaching and Why It Almost Didn’t Happen 00:10:34 – A Costly Distraction: A Failed Investment 00:12:30 – The Emotional Weight of Money and Investing 00:15:00 – A Brutal Financial Loss: Losing $100K a Month 00:18:00 – The Transition from Founder to Investor 00:20:15 – The Importance of Financial Safety Nets 00:24:15 – Balancing Risk and Stability 00:29:00 – The Concept of Wealth Beyond Money 00:30:06 – Unlimited Freedom vs. Purpose 00:32:03 – Defining Purpose and Service to Others 00:36:00 – The Danger of Retiring Too Early 00:40:00 – Lessons from Childhood: How Early Experiences Shaped His Drive 00:46:00 – Parenting and Entrepreneurship 00:52:25 – Post-Exit Traps to Avoid 00:57:45 – Rebuilding Structure and Identity After an Exit 01:06:00 – Final Lessons: The Power of Stillness 01:07:22 – How Mike Wants to Be Remembered
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#50
Mar 4, 2025 · 1 hr 12 min
$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
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#49
Feb 28, 2025 · 55 min
From $100M Exit to Fulfilment: Josh Payne’s Playbook
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. 00:00:00 Introduction 00:00:45 Selling StackCommerce: Was It a Happy Moment? 00:02:00 The Emotional Impact of Selling a Company 00:03:30 Why Money Didn’t Solve Everything 00:05:15 Prioritizing Family After the Exit 00:06:30 Leaving the Company: A Tough Identity Shift 00:07:45 Taking a Healing Family Trip 00:09:00 Training for an Ironman & Overcoming Mental Barriers 00:12:30 Decoupling Identity from Business 00:14:00 Leadership & Purpose Beyond Business 00:16:00 Sacrifice vs. Suffering in Entrepreneurship 00:18:45 Ironman Training: Lessons in Overcoming Fear 00:22:00 The Challenge of Finding a New Purpose 00:23:45 Why Start Another Business After an Exit? 00:27:00 Learning to Build a Company Without Fear 00:30:00 The Difference Between First and Second Businesses 00:33:00 Finding a Sustainable Way to Build Again 00:35:00 Balancing Business & Personal Life After Exit 00:38:15 Why Many Second Businesses Fail 00:42:00 The Importance of Motivation in a New Startup 00:45:30 Avoiding the Trap of Losing Interest Midway 00:48:00 The Role of Peer Groups Like Tiger 21 00:50:30 How Long Does It Take to Truly Adjust After Exit? 00:53:00 Raising Kids With Wealth: Teaching Responsibility 00:54:00 Closing Thoughts & Future Plans
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#48
Feb 18, 2025 · 1 hr 35 min
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. 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
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#47
Jan 7, 2025 · 1 hr 40 min
Cory Janssen. 17 Years Post-Exit: Insights from Investopedia’s Founder
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 and working. But this time it felt different. His focus shifted toward unselfish, larger impact goals. His new non-monetary motivation gave him powerful drive and a clear sense of direction and alignment. Today, Cory finally feels deeply fulfilled, energised and joyful. There is so much to learn from Cory's story and we are so lucky he agreed to share it openly. It's rare, raw and packed with specific practical insights for anyone navigating the complexities of post-exit life. _____________________________________________________ 00:00:00 Introduction 00:01:40 Guest Introduction: Cory Janssen’s Story 00:04:00 Founding Investopedia: The Early Days 00:10:55 Deciding to Sell Investopedia 00:22:15 Regret After Selling: Financial and Emotional Impact 00:35:10 Working for the Acquirer: Lessons Learned 00:46:50 Negotiating the Sale Process: Tips for Founders 00:56:20 Post-Exit Struggles: Managing Wealth and Purpose 01:07:10 Challenges of Professional Investing 01:15:30 Rediscovering Passion for Building: Transitioning to AI 01:26:15 Balancing Parenthood and Entrepreneurship 01:37:30 Raising Kids with Wealth: Avoiding Entitlement 01:40:00 Closing Reflections and Key Takeaways
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#46
Jan 6, 2025 · 1 hr 48 min
Michael Miller. Meditation: the Ultimate Post-Exit Medicine
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 all credit meditation for helping them on their own post-exit journeys. Before discovering his calling as a meditation teacher, Michael had a successful business career. That experience gives him a unique ability to explain meditation in ways that make sense to us entrepreneurs. If you've tried meditation before, but let it slip, this might just inspire you to pick it back up. _____________________________________________________ 00:00 The Healing Power of Meditation 02:46 Personal Journeys and Transformations 06:10 The Science Behind Meditation 11:54 Meditation as a Decision-Making Tool 17:49 The Ripple Effect of Meditation 24:06 Creating Peace from Within 40:07 The Ripple Effect of Inner Peace 44:51 The Journey of Personal Growth Post-Success 49:52 Addiction as a Spiritual Search 52:15 From Material Success to Fulfillment 59:33 Designing a Toolbox for Holistic Leadership 01:13:30 The Journey of Self-Discovery 01:18:05 Navigating Life Stages and Transitions 01:23:25 Embracing Discomfort for Growth 01:29:35 The Role of Community and Giving Back 01:34:08 Traveling with Purpose 01:39:23 Understanding Consciousness 01:42:34 Defining Purpose and Connection
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#45
Dec 3, 2024 · 57 min
Sarah Douglass. Post-Wealth Search for Happiness
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 by success, the difficulty of resisting the urge to immediately start something new just to feel productive, and her shift from chasing external milestones to embracing intentional living—rediscovering who she is as a whole being, not just as an entrepreneur. _____________________________________________________ 00:00:00: Introduction and greetings 00:01:04: Sarah's business journey beginnings (Music school) 00:01:39: Transition to selling online (Discovery at dinner) 00:02:04: Starting with camping gear (Wise Owl Outfitters) 00:02:56: Challenges and operations (Traveling to China) 00:03:40: Balancing family and business (Moving and kids) 00:04:23: Working with her husband 00:05:21: Husband's role and career shift (Becoming a painter) 00:04:37: Decision to sell the business 00:05:00: Influences and reasons for selling 00:07:01: Financial freedom and exiting strategy 00:08:16: The selling process (Timeline and logistics) 00:09:56: Reflections on the buyer's bankruptcy 00:11:06: Emotional impact of selling 00:12:10: Post-sale challenges and burnout 00:13:23: Realizations and health impact 00:14:40: Personal and existential reflections 00:16:55: Seeking and understanding contentment 00:18:37: Advice on spirituality and life direction 00:19:06: Initial thoughts on spirituality and personal development 00:19:23: Exploring different avenues for growth 00:19:46: Impact of personal coaching and physical health 00:20:36: Reflection on life's purpose post-exit 00:21:32: Evaluating new opportunities and the allure of starting new businesses 00:25:00: Importance of being helpful to others 00:27:18: Finding balance in life and prioritizing oneself 00:27:50: Balancing motherhood and business 00:32:17: Handling wealth and teaching children about money 00:34:42: Shifts in business motivation without the need for money 00:38:17: Importance of having a supportive team 00:39:08: Pursuing new, exciting projects 00:40:02: Balancing current business with new ventures 00:40:26: Benefits of taking extended trips 00:42:04: Discovering oneself through new experiences 00:46:04: Reflections on legacy and impact on others 00:48:02: Interpretation of "Stay hungry, stay foolish" 00:51:03: Struggles of balancing business and family as a woman 00:56:06: Comparison of post-exit life to athletes' career transitions 00:56:38: Feeling lonely during the process 00:56:52: Searching for information online 00:57:15: Conclusion and thank you
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#44
Nov 20, 2024 · 47 min
Tim Schumacher. Sedo’s Exited Founder on Work-Life Balance
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 supernormal, the bootstrapper mindset, being a scaler versus a zero-to-one founder, and finding new purpose in tackling climate change. _____________________________________________________ 00:00:00 - 00:00:39 Introduction 00:00:39 - 00:02:58 Tim Schumacher's Exit and Reflections 00:02:58 - 00:05:58 Transition to New Ventures 00:05:58 - 00:07:28 The Importance of Rest and Work-Life Balance 00:07:28 - 00:09:51. Personal Interests and Climate Change 00:09:51 - 00:11:55. Evolution of Motivation and Values 00:11:55 - 00:16:38. The Bootstrap Mindset 00:16:38 - 00:18:28. Balancing VC and Bootstrap Approaches 00:18:28 - 00:25:30. Scaling vs. Building from Scratch 00:25:30 - 00:29:37. Financial and Purposeful Integration 00:29:37 - 00:31:12 Managing Identity Change Post-Exit 00:31:12 - 00:37:05 Work-life Balance and European Influence 00:37:05 - 00:36:59. Entrepreneurial Legacy and Family 00:36:59 - 00:42:20. Reflecting on Business Strategies and Learnings 00:42:20 - 00:45:26 Revisiting Entrepreneurial Failures 00:45:26 - 00:47:09. Cultural Exposure and Entrepreneurial Growth 00:47:09 - 00:49:29 Purpose and Motivation Beyond Business
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