Exit Paradox

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._____________________________________________________TIME STAMPS:00:00 – Why your exit dollar figure doesn’t define you00:16 – Introduction: Barak Kaufman & Post Exit Founders (PEF)01:08 – Life after selling: discomfort, confusion, recalibration02:11 – Supporting exited founders to make better decisions03:07 – Barak reflects on being interviewed08:18 – Origins of PEF: growth, community DNA, culture of kindness10:02 – Challenges of scale: 5,000+ members and maintaining trust12:50 – Dating, cofounders, and tribes within PEF14:24 – Building “intentional serendipity” in the community16:47 – The importance of in-person connection22:32 – Lack of judgment and welcoming messy post-exit journeys24:58 – Why PEF doesn’t ask about the size of your exit27:10 – The “golden cage” of financial freedom28:25 – Barak’s unusual path: investor → founder → investor35:44 – Barak’s mission: helping exited founders find their purposeafter acquisition37:32 – Early post-exit struggles39:11 – Joining Vine Ventures and rediscovering purpose42:35 – From negative one to zero: finding clarity44:44 – Angel investing regrets & lessons learned46:39 – Fulfillment, family, and life design58:46 – Parenting identity as post-exit mission59:40 – Hiding behind noble roles: parenting, philanthropy, boards01:02:18 – Why many rush into a new venture too quickly01:03:50 – The three typical post-exit paths: messy middle, next mountain, not seeking01:06:52 – The “wasted decade” risk if clarity is delayed01:17:15 – Different founder motivations: curiosity, relationships, efficiency01:18:51 – Closing thoughts & gratitude

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 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

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 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

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-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

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

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 Story00:01:06 – Why Exited Founders Make Bad Investors00:05:15 – From Angel Investing to Private Equity00:09:00 – Why Most Second Companies Fail00:10:15 – Lessons from a Failed Acquisition00:12:07 – Buying vs. Building a Business00:14:34 – Regret After Exit and Finding New Purpose00:17:27 – Sacrifice, Purpose & The Next Big Thing00:20:18 – Impact, Meaning & Philanthropy Struggles00:23:44 – Coaching Entrepreneurs as a Calling00:25:18 – Why He Hasn’t Jumped into a Big Mission Yet00:27:00 – Kids, Family, and Timing the Next Move00:29:00 – Angel Investing: Rise and Decline00:31:06 – The Illusion of Control in Angel Investing00:32:35 – Advice for New Angel Investors00:34:45 – Lifestyle Balance Post-Exit00:36:00 – The Grind Years: 20-Hour Days and Stress00:38:00 – Building a Business with His Wife00:41:30 – Division of Labor and Complementary Skills00:43:00 – Conflict Resolution in a Husband-Wife Team00:44:45 – Why They Didn't Start a Second Business Together00:46:15 – Raising Entrepreneurial Kids with Wealth00:50:45 – The Only Real Passive Investing Strategy00:53:26 – Life Rules: Wealth vs. Freedom00:56:40 – Is Balance Between Mission and Freedom Possible?00:58:45 – Mental Health After the Exit01:01:00 – Why He Shares His Story Publicly01:03:15 – A Book for His Kids and Maybe the World01:07:17 – Will He Publish It?01:09:41 – How Adam Wants to Be Remembered01:10:36 – Closing Thanks & Final Reflections

Mike Brown's post-exit journey led him from chaos to clarity, but not right away. He had to go through a painful divorce, a business failure, financial losses and emotional turmoil.Today we are talking about what he's learned and why he decided to dedicate himself to coaching. Mike, I'd love you to walk me through step by step, what happened to you in those first few weeks after the exit? How you felt, how you thought?_______________🔗 CONNECT WITH MIKE:🎥 YouTube Channel - ‪@mbrown_co‬ 🐦 X (Twitter) - https://x.com/mbrown_co📸 Instagram - @mbrown.co💻 Website - https://unbreakablewealth.com/👥 Linkedin -   /mikebrownactual  _________________TIME STAMPS:00:00:00 – Introduction00:00:37 – The Aftermath of Selling a Business00:02:07 – Reality Hits: The Post-Exit Crisis00:03:19 – The Connection Between Entrepreneurship and Divorce00:05:00 – Chasing Achievement vs. Finding Purpose00:06:40 – 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 Happen00:10:34 – A Costly Distraction: A Failed Investment00:12:30 – The Emotional Weight of Money and Investing00:15:00 – A Brutal Financial Loss: Losing $100K a Month00:18:00 – The Transition from Founder to Investor00:20:15 – The Importance of Financial Safety Nets00:24:15 – Balancing Risk and Stability00:29:00 – The Concept of Wealth Beyond Money00:30:06 – Unlimited Freedom vs. Purpose00:32:03 – Defining Purpose and Service to Others00:36:00 – The Danger of Retiring Too Early00:40:00 – Lessons from Childhood: How Early Experiences Shaped His Drive00:46:00 – Parenting and Entrepreneurship00:52:25 – Post-Exit Traps to Avoid00:57:45 – Rebuilding Structure and Identity After an Exit01:06:00 – Final Lessons: The Power of Stillness01:07:22 – How Mike Wants to Be Remembered

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 - Introduction00:00:14 - Learning from Failure vs. Success00:00:27 - Building a Business as a Married Couple00:01:08 - First Meeting and Early Impressions00:02:30 - Life After an Exit00:03:08 - Golf.com: The First Big Exit00:06:58 - The Struggles of Entrepreneurship00:09:14 - The Emotional Toll of Entrepreneurship00:10:35 - Taking a Break After an Exit00:11:14 - Was Their First Exit Life-Changing?00:12:54 - Why Start Another Business?00:14:31 - Entrepreneurship with Three Kids00:16:47 - Why Entrepreneurs Keep Going00:19:41 - Becoming Investors00:23:20 - The Hardships Behind Entrepreneurship00:28:17 - Coping with Post-Exit Stress00:31:41 - Entrepreneurs and Mental Health00:34:55 - Reframing Anxiety & ADHD as Superpowers00:38:46 - The Dark Side of Entrepreneurship00:44:01 - Work-Life Balance: Do They Have One?00:48:01 - Michael’s Attempt at a Painting Career00:50:12 - Filtering Opportunities00:52:28 - Navigating Marriage After an Exit00:55:15 - Raising Kids with Wealth01:02:11 - Teaching Kids About Money and Responsibility01:09:04 - The Purpose of Their Book01:11:20 - 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/anastasiakorolevaTikTok - https://www.tiktok.com/@anastasia.korolev7

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._____________________________________________________00:00:00 Introduction 00:00:45 Selling StackCommerce: Was It a Happy Moment?00:02:00 The Emotional Impact of Selling a Company00:03:30 Why Money Didn’t Solve Everything00:05:15 Prioritizing Family After the Exit00:06:30 Leaving the Company: A Tough Identity Shift00:07:45 Taking a Healing Family Trip00:09:00 Training for an Ironman & Overcoming Mental Barriers00:12:30 Decoupling Identity from Business00:14:00 Leadership & Purpose Beyond Business00:16:00 Sacrifice vs. Suffering in Entrepreneurship00:18:45 Ironman Training: Lessons in Overcoming Fear00:22:00 The Challenge of Finding a New Purpose00:23:45 Why Start Another Business After an Exit?00:27:00 Learning to Build a Company Without Fear00:30:00 The Difference Between First and Second Businesses00:33:00 Finding a Sustainable Way to Build Again00:35:00 Balancing Business & Personal Life After Exit00:38:15 Why Many Second Businesses Fail00:42:00 The Importance of Motivation in a New Startup00:45:30 Avoiding the Trap of Losing Interest Midway00:48:00 The Role of Peer Groups Like Tiger 2100:50:30 How Long Does It Take to Truly Adjust After Exit?00:53:00 Raising Kids With Wealth: Teaching Responsibility00:54:00 Closing Thoughts & Future Plans

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.

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. _____________________________________________________ TIME STAMPS: 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

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. _____________________________________________________ TIME STAMPS: 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

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. _____________________________________________________ TIME STAMPS: 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

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. _____________________________________________________TIME STAMPS:00:00:00 - 00:00:39 Introduction00:00:39 - 00:02:58 Tim Schumacher's Exit and Reflections00:02:58 - 00:05:58 Transition to New Ventures00:05:58 - 00:07:28 The Importance of Rest and Work-Life Balance00:07:28 - 00:09:51. Personal Interests and Climate Change00:09:51 - 00:11:55. Evolution of Motivation and Values00:11:55 - 00:16:38. The Bootstrap Mindset 00:16:38 - 00:18:28. Balancing VC and Bootstrap Approaches00:18:28 - 00:25:30. Scaling vs. Building from Scratch00:25:30 - 00:29:37. Financial and Purposeful Integration00:29:37 - 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

Rick Eigenbrod is a deeply respected thinker in the post-exit world. A clinical psychologist and co-author of the classic Yale paper What’s Next: The Entrepreneur’s Epilogue, he’s spent years guiding founders through life after the exit as an executive coach. In this conversation, we get into why Rick believes a “death of who we used to be” and a subsequent "re-birth" are inevitable post-exit, and how resisting these changes only adds to the struggle. Rick generously shares the tools and exercises he’s found most effective in navigating this transformative process. We also explore the grip of dopamine addiction, the healing power of legitimizing post-success frustration, simple ways to reconnect with our natural curiosity and playfulness, and the bittersweet reality of leaving some people behind as we experience exponential personal growth. _____________________________________________________ TIME STAMPS: 00:00:00: Introduction 00:00:21: The paradox of success 00:00:43: Rick's background and contributions 00:01:04: Discussion on post-exit rebirth and struggles 00:01:12: Exploring dopamine addiction and post-success frustrations 00:02:30: Exploring the post-exit maze 00:02:45: Rick's background and experience with exited founders 00:04:47: Rick's critical event with Vistage group 00:06:09: The price and prize of money and freedom 00:07:52: Reflections on the dual meaning of success 00:08:53: Grappling with post-exit paradox 00:09:41: The "focusing illusion" and the arrival fallacy 00:11:12: The societal pressure to be happy post-exit 00:12:01: Support groups and legitimating experiences 00:13:08: Initial reactions and reflections on the post-exit reality 00:14:31: The societal issue of ignoring exited founders 00:15:33: The lack of support and self-blame post-exit 00:18:00: Escaping the blank sheet of paper 00:19:07: Dealing with loss of motivation 00:20:38: The challenge of striving without a company 00:22:21: Stories of loss of identity and success paradox 00:23:02: The impact on identity and structure post-exit 00:24:29: Avoiding the inclination to fill the void with the same elements 00:25:32: Closing the first business 00:26:18: Question of true desires and freedom paradox 00:27:19: Attempt to create a model from experiences 00:29:06: Journey from identity to meaning and structure 00:30:02: Revisiting personal development opportunities 00:33:16: Financial dangers post-exit 00:35:30: Paradox of money and its role 00:36:09: Evolution of the meaning of wealth 00:41:03: Refusal of the call and negative transfer of learning 00:44:10: Dopamine addiction as an obstacle 00:47:00: Fear of losing entrepreneurial identity 00:49:00: Navigating the journey of death and rebirth in personal growth 00:51:13: Leaving people behind during personal growth 00:52:29: Real journeys begin where fairy tales end 00:54:08: Redefining retirement and societal expectations 00:56:03: Advising young successful entrepreneurs 00:57:23: Identifying and addressing emotional struggles post-sale 00:58:46: Embracing a Mosaic Life 01:00:00: Communicating personal transitions to others 01:03:07: Returning to business after personal growth 01:05:00: Listening for truth, vitality, and fear in decisions 01:07:32: Distinguishing between legitimate fears and psychological barriers 01:09:08: Discernment of skill-related fears in new ventures 01:10:14: Transitioning from entrepreneur to investor 01:13:20: Rediscovering a sense of purpose post-exit 01:14:00: The search for meaning and what matters now 01:16:22: Two ways of knowing and going: Destination vs Direction 01:17:57: Understanding fulfillment and satisfaction 01:19:20: The importance of savoring moments 01:21:00: Stories about finding fulfillment 01:23:26: Legacy question 01:24:00: Discussion about dynamics of arrival 01:27:00: The role of intention in satisfaction

Roy Rubin the visionary founder of Magento, built the open source e-commerce platform from the ground up, leading it to a remarkable exit to eBay in just four years. He then stayed on at eBay for two years, but felt suffocated by corporate walls. That's when it hit him. He barely knew his family anymore. So he and his wife pulled their kids out of school, packed up. and set off on an open-ended journey around the world. For 14 months, they traveled without a plan, letting each destination choose them and discovered what freedom really meant. When they returned, threw himself into the challenge of cycling and completed an Ironman. He also started an angel investment firm to stay intellectually engaged. He has built a beautiful life, but now 13 years post-exit, he is still looking for a new purpose. Roy is torn between the urge to build something big again and the fear of sacrificing his family and lifestyle. Roy is disarmingly open and witty in this conversation. His ideas on personal growth, leadership and fulfillment are fresh and thought-provoking. _____________________________________________________ TIME STAMPS: 00:00:00: Introduction and greetings 00:01:38: Roy's background and introduction to Magento 00:02:3: The founding and growth of Magento 00:03:36: Why Magento was sold to eBay 00:05:28: Reflections on selling Magento 00:05:53: Period after selling: Working at eBay 00:06:51: Challenges and experiences at eBay 00:10:18: Frustrations and limitations at eBay 00:11:07: Difficulty in leading within eBay 00:13:39: Reflections on regret and learning from the experience 00:15:53: Pain of working at eBay 00:18:04: Changes in the leadership team post-acquisition 00:19:25: Leadership style and inspiration 00:22:07: Transparency and leadership approach 00:25:24: Personal reflections post-exit 00:25:48: Reflecting on leaving Magento in 2013 00:28:03: Deciding to leave eBay after Magento's Imagine conference in 2014 00:29:15: The decision to travel with family for 14 months 00:30:00: The travel route through Central America, South America, Asia, and Europe 00:31:03: The travel experience and its impact on family dynamics 00:36:04: Encouragement to other founders to take time off and travel 00:43:02: Discovering new passions post-travel, specifically Iron Man and cycling 00:45:59: Introduction to Personal Journey 00:46:26: Discovering Passion for Sports 00:46:10: Reinventing Post-eBay Life 00:46:44: Starting the Fund During COVID 00:48:04: Transition to Angel Investing 00:51:27: Managing Wealth Post-Magento Sale 00:54:03: Investment Philosophy and Public Equities 00:56:45: The Non-Financial Rewards of Investing 00:58:17: Search for Purpose Beyond Business 01:01:27: Reflection on Purpose During Magento Years 01:03:33: Balancing Life with Current Ventures 01:06:12: Discussing a life of 24/7 dedication 01:06:47: The search for purpose 01:08:01: Meeting new people 01:10:00: The intense journey with Magento 01:12:56: Coping with the transition post-acquisition 01:16:07: Being a creator versus an operator 01:19:11: Future impact and legacy 01:22:10: The desire for more meaningful work 01:26:21: Closing remarks and goodbyes

Ten years ago, Brock Weatherup sold his first company, Pet360.com, to PetSmart for $160 million. It took under five years to build. Since then, he’s had two more successful exits, but two years ago, his journey took an unexpected turn when a life-changing medical diagnosis reshaped his entire outlook. In this episode, Brock talks about the secrets behind his consistent success, what keeps him optimistic and gives him a sense of purpose, and how he cultivates relationships in both business and private life. _____________________________________________________ TIME STAMPS: 00:00:00: Introduction 00:01:17: Brock's first company exit experience 00:03:02: Transition challenges after the exit 00:03:31: Acquisition by PetSmart and transition experience 00:06:00: Acquisition of PetCoach 00:07:45: Brock's role and relationship with PetCoach team 00:08:59: Insights on being a startup to grown-up stage founder 00:09:41: Brock's involvement in subsequent businesses 00:11:00: Selling Great Pet Care due to MS diagnosis 00:11:56: Diagnosis impact on priorities and motivations 00:13:09: Adjusting to life with MS 00:14:38: Post-exit reflections and personal journey 00:15:41: Engaging with the business community in new ways 00:16:27: Realignment of life and business perspectives 00:21:47: Reflections on Sharing Knowledge and Purpose 00:22:08: Importance of Meaningful Involvement and Family Time in Purpose 00:22:26: Daily Approach to Living Purposefully 00:24:10: Impact of Diagnosis on Relationships and Support System 00:26:07: Friends' Support During a Difficult Time 00:26:54: Tracing the Evolution from First Business to Present 00:27:03: Story of the First Business Failure 00:30:02: Lessons Learned from Business Failures 00:31:15: The Role of Investors and Ethics 00:35:59: Challenges of Transitioning from Owner to Employee Mentality 00:38:24: Celebrating Failures and Learning from Them 00:40:52: Keeping Perspective in Business Ventures 00:41:14: Adapting and Learning in New Environments 00:42:48: Introduction to the CEO’s vision 00:44:09: Staying humble and continuing to learn 00:51:22: Balancing experience and youthful energy 00:52:06: The importance of continuous learning 00:54:01: Past performance vs future success 00:56:15: Building successful teams 00:59:55: The value of the cap table and smart investment decisions 01:02:22: Financial considerations and risk profiles 01:03:27: Final advice for building a new business after an exit 01:02:50: Being intentional in business and personal life 01:03:11: Setting personal intentions and accountability 01:04:25: Specific goals and realistic expectations 01:06:00: Applying business discipline to personal life 01:07:15: Correlation between personal and professional success 01:08:08: Open communication and its importance 01:09:19: Achieving balance and happiness 01:09:22: How to be remembered

Three years ago, Scott Wolfe sold his company, Levelset, for half a billion dollars. Excited and relieved at first, he soon found himself deeply frustrated with the reality that his vision for the business would now never be realized. Scott is a natural creative who sees building a business as an artistic endeavor. It was this intrinsic need to create that sustained him through the grueling journey of building his business. Post-exit, he misses being driven by that vision and working alongside his exceptional, organically built team—one he feels can never be re-created. In this conversation, we explore the pros and cons of starting a sequel, the paradox of purpose, being a true “hedgehog,” the need for authenticity, full-time parenting, and raising entrepreneurial children. _____________________________________________________ TIME STAMPS: 00:00:00: Introduction and welcome to Scott 00:01:11: Reflections on selling the company 00:02:22: Feelings post-sale and personal identity 00:05:01: Comparing business to art 00:06:58: Transition from attorney to entrepreneur 00:08:57: Founding and growing Levelset 00:11:15: Key roles and talents in the company 00:13:21: Starting a new business and family considerations 00:19:00: Debating the reasons to start another business 00:21:02: Seeking purpose and fulfillment 00:23:21: The necessity of creativity and purpose 00:24:06: The challenges of balancing personal and professional life 00:25:01: The paradox of purpose 00:26:31: Rebuilding life and purpose post-exit 00:27:56: Adjustments and surprises after exiting a company 00:29:02: Facing mortality and existential reflections post-exit 00:31:36: Managing personal expectations and regrets 00:34:07: Reflecting on unfinished business and the non-finality of accomplishments 00:38:03: The journey and appetite for creative endeavors 00:40:44: Exploring new experiments and hobbies post-exit 00:42:28: Writing and reflecting on vision after business exit 00:43:32: Building and helping companies after the exit 00:45:08: Structuring the company's vision 00:45:48: Financial exit and its impact 00:47:25: Managing newfound wealth 00:54:58: Becoming a cautious investor 00:56:00: The hedgehog concept 00:58:53: The influence of entrepreneurial family upbringing 01:01:42: Wishing entrepreneurial experiences for children 01:05:32: The importance of self-reliance and vision for entrepreneurs 01:06:22: Strategy Development and Investment Philosophy 01:08:07: Changes in Motivation Over Time 01:10:40: Current Motivation and Challenges 01:13:36: Inspiration and Choosing People to Surround Yourself With 01:14:21: Building a Network Organically 01:16:33: The Importance of Purpose and Motivation 01:17:49: Reflections on Authenticity and Meeting New People 01:18:04: Legacy and How to be Remembered

My friend Jonathan has chosen to remain anonymous in exchange for stepping outside his comfort zone — and that he did! Eight years ago, he began a gradual exit from his incredibly successful, bootstrapped company. This strategic approach had an unexpected benefit: it smoothed his post-exit transition, making it more manageable both emotionally and financially. His search for a new purpose—a lengthy and confusing path for most—became clear and compelling after his family was hit by a mental health issue. In this interview, Jonathan shares raw, unconventional wisdom about the advantages of bootstrapping and exiting in stages, and how painful personal challenges gave him a new purpose and source of fulfillment. _____________________________________________________ TIME STAMPS: 00:00: Introduction 01:00 Transition after selling the company 01:20: Jonathan's unconventional wisdom 02:08: Jonathan's previous careers 03:06: Motivation for starting a new business 03:53: Challenges faced in hierarchical systems 04:44: Importance of money in decisions 05:47: Founding a data business 06:44: Challenges in raising money 08:24: Misconceptions about data 10:03: Advantages of bootstrapping 11:14: Financial challenges and salaries 14:53: Impact of minority exit in 2016 17:02: Reasons for full business exit 18:12: Dividend checks and responsibility 19:04: Working with private equity firms 21:04: Importance of choosing the right partner 22:10: Reflections on Exiting During COVID 23:00: Health Issues and Impact on Business 24:03: Regrets and Decisions on Exiting 25:10: Continuing Involvement Post-Exit 26:14: Merging with a US Company 27:02: Adjusting to Life After Business 28:32: Personal and Family Focus Post-Retirement 30:26: Supporting Academic Research and Mental Health 31:29: Motivation of Wealth Training for Children 35:17: Disinterest in Material Possessions 38:13: Sources of Fulfillment and Life Satisfaction 41:47: Outdoor Activities and Personal Well-being 42:00: Processing Life's Experiences into Wisdom 45:36: Small experiences of delight 46:12: Caring for employees through share options 46:50: Satisfaction from contributing to others' happiness 47:08: Reflection on being remembered 48:04: Conclusion and gratitude

Jason Kirby. He Sold Liquid Sky software to Walmart six years ago, but became disillusioned when Walmart abruptly scrapped the company's ambitious plans. Seeking a new direction, Jason joined Generation Esports, rapidly scaled it and exited three years ago. This last exit prompted Jason to reassess his priorities, leading him to focus on family, health and meaningful work. This shift inspired him to found Thunder, a tech enabled investment bank and launch the fundraising demystified podcast. In this interview, Jason shares his journey from high stress startups to a life centered on fulfillment and purpose. _____________________________________________________ TIME STAMPS: 00:00:00: Overview of Jason’s Expertise 00:01:27: Starting Liquid Sky 00:01:56: Formation and Operational Beginnings of Liquid Sky 00:02:24: The Vision and Mission of Liquid Sky 00:03:11: Partnership and Expansion Efforts 00:03:37: Business Philosophy and Personal Contribution 00:05:15: Diverse Industry Experience 00:06:50: Curious Nature and Learning Process 00:06:53: Liquid Sky’s Rapid Growth and Sale to Samsung 00:08:05: The Failed Acquisition by Samsung 00:10:17: Crisis and Pivot Strategy 00:11:01: Final Attempts for Acquisition and Survival 00:13:28: New Strategy with Walmart 00:15:39: Outcome and Life Post-Acquisition by Walmart 00:19:42: Excitement about Walmart Gaming 00:20:25: Transition to San Diego and New Opportunity 00:20:50: Introduction to Generation Esports 00:21:48: Investing Energy into Generation Esports 00:24:05: Initial Reflection and Momentum 00:25:42: Navigating the COVID-19 Challenges 00:26:28: Series A Funding and Rising Tensions 00:29:06: Decision to Leave Generation Esports 00:31:00: Self-discovery and New Relationships 00:35:19: Learning from Relationship Dynamics 00:36:00: Considering the Next Move 00:36:10: The Idea of Starting Thunder 00:36:42: The seed for Thunder 00:37:18: What Thunder does 00:39:02: Thunder as a tech-enabled investment bank 00:40:21: Introduction to the podcast "Fundraising Demystified" 00:42:00: Origin of "Fundraising Demystified" 00:44:04: The value of understanding venture capital 00:45:11: Advice for post-exit founders considering new ventures 00:52:01: Importance of risk tolerance 00:52:58: Determining the endgame for new businesses 00:53:41: Plans for Thunder 00:54:14: Decision against starting another big business 00:55:04: Balancing career and family priorities 00:55:48: Balancing Family and Ambitions 00:56:07: Introduction to Entrepreneurship in College 00:56:11: Influence of Successful Entrepreneurs 00:56:35: Reflections on Success and Family Time 00:56:39: Closing Remarks