Exit Paradox

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 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.

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

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 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

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 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

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.

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-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

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 - 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

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 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

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. 🔗 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

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 Introduction00:00:45 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. 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 - Introduction00:02:25 - The Story of Velocity Black00:07:46 - Selling Velocity Black to Capital One00:07:05 - Why Alex Started Another Business Before Selling His First One00:10:52 - The Founder’s Existential Crisis After an Exit00:12:45 - The Shortage of Builders, Not Investors00:14:19 - Work-Life Balance & Health After an Exit00:16:21 - Lessons from Running a 24/7 Business00:19:52 - Changing Approach to Work with Sequel00:21:19 - Different Approaches to Post-Exit Businesses00:24:19 - Sequel: Building a Next-Gen Goldman Sachs00:27:26 - Managing Motivation After Financial Success00:31:03 - Fulfillment vs. Happiness: What Really Matters?00:33:15 - The Biohacking & Longevity Obsession00:35:51 - Community & Meaning in Life After an Exit00:39:13 - The Idea of Creating a New Religion00:45:46 - The Role of Structure & Responsibility in Life.00:54:08 - The Challenge of Freedom After an Exit00:57:46 - Angel Investing & How It Led to Sequel01:03:42 - Helping Athletes Transition Beyond Their Careers01:07:37 - Building a Legacy vs. Just Making Money01:10:52 - Avoiding Mistakes in Early-Stage Investing01:15:30 - The Power of Influence in Investing01:20:05 - Sequel’s Future Plans & Scaling the Model01:25:00 - What Drives Long-Term Success?01:30:10 - Final Thoughts & Advice for Founders

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 Introduction00:01:40 Guest Introduction: Cory Janssen’s Story00:04:00 Founding Investopedia: The Early Days00:10:55 Deciding to Sell Investopedia00:22:15 Regret After Selling: Financial and Emotional Impact00:35:10 Working for the Acquirer: Lessons Learned00:46:50 Negotiating the Sale Process: Tips for Founders00:56:20 Post-Exit Struggles: Managing Wealth and Purpose01:07:10 Challenges of Professional Investing01:15:30 Rediscovering Passion for Building: Transitioning to AI01:26:15 Balancing Parenthood and Entrepreneurship01:37:30 Raising Kids with Wealth: Avoiding Entitlement01:40:00 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. _____________________________________________________ 00:00 The Healing Power of Meditation02:46 Personal Journeys and Transformations06:10 The Science Behind Meditation11:54 Meditation as a Decision-Making Tool17:49 The Ripple Effect of Meditation24:06 Creating Peace from Within40:07 The Ripple Effect of Inner Peace44:51 The Journey of Personal Growth Post-Success49:52 Addiction as a Spiritual Search52:15 From Material Success to Fulfillment59:33 Designing a Toolbox for Holistic Leadership01:13:30 The Journey of Self-Discovery01:18:05 Navigating Life Stages and Transitions01:23:25 Embracing Discomfort for Growth01:29:35 The Role of Community and Giving Back01:34:08 Traveling with Purpose01:39:23 Understanding Consciousness01:42:34 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._____________________________________________________ 00:00:00: Introduction and greetings00:01:04: 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 husband00:05:21: Husband's role and career shift (Becoming a painter)00:04:37: Decision to sell the business00:05:00: Influences and reasons for selling00:07:01: Financial freedom and exiting strategy00:08:16: 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._____________________________________________________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 Mindset00:16:38 - 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-Exit00:31:12 - 00:37:05 Work-life Balance and European Influence00:37:05 - 00:36:59. Entrepreneurial Legacy and Family00:36:59 - 00:42:20. Reflecting on Business Strategies and Learnings00:42:20 - 00:45:26 Revisiting Entrepreneurial Failures00:45:26 - 00:47:09. Cultural Exposure and Entrepreneurial Growth00:47:09 - 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._____________________________________________________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. _____________________________________________________00:00:00: Introduction and greetings00:01:38: 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._____________________________________________________ 00:00:00: Introduction00:01:17: Brock's first company exit experience00:03:02: Transition challenges after the exit00:03:31: Acquisition by PetSmart and transition experience00:06:00: Acquisition of PetCoach00:07:45: Brock's role and relationship with PetCoach team00:08:59: Insights on being a startup to grown-up stage founder00:09:41: Brock's involvement in subsequent businesses00:11:00: Selling Great Pet Care due to MS diagnosis00:11:56: Diagnosis impact on priorities and motivations00:13:09: Adjusting to life with MS00:14:38: Post-exit reflections and personal journey00:15:41: Engaging with the business community in new ways00:16:27: Realignment of life and business perspectives00:21:47: Reflections on Sharing Knowledge and Purpose00:22:08: Importance of Meaningful Involvement and Family Time in Purpose00:22:26: Daily Approach to Living Purposefully00:24:10: Impact of Diagnosis on Relationships and Support System00:26:07: Friends' Support During a Difficult Time00:26:54: Tracing the Evolution from First Business to Present00:27:03: Story of the First Business Failure00:30:02: Lessons Learned from Business Failures00:31:15: The Role of Investors and Ethics00:35:59: Challenges of Transitioning from Owner to Employee Mentality00:38:24: Celebrating Failures and Learning from Them00:40:52: Keeping Perspective in Business Ventures00:41:14: Adapting and Learning in New Environments00:42:48: Introduction to the CEO’s vision00:44:09: 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._____________________________________________________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._____________________________________________________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._____________________________________________________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

Matthew Johnson sold his healthcare software company 11 years ago, after leading it through three rounds of fundraising in just three years. Alongside his twin brother Nathan, he then acquired and transformed TruConnect into a telecom powerhouse. Matthew also co-founded the technology investment bank Drake Star Partners, leveraging his earlier investment banking experience in NYC. Balancing life between LA and Switzerland, he also leads a nonprofit providing wheelchairs to disabled children. Let’s dive into his unique post-exit lessons on staying motivated, enjoying life, and raising entrepreneurial children.TIME STAMPS:00:00:00 - 00:02:34 - Introduction and Career Transition00:02:34 - 00:03:23 - The First Startup Experience00:03:23 - 00:06:33 - Building True Connect00:06:33 - 00:07:50 - Financial Discipline and Management Philosophy00:07:50 - 00:12:42 - Transitioning from Finance to Entrepreneurship00:12:42 - 00:15:08 - Balancing Multiple Ventures00:15:08 - 00:19:05 - Considering Exiting True Connect00:19:05 - 00:23:28 - Lessons in Hiring and Management00:23:28 - 00:33:05 - Managing Investments and Personal Fulfilment00:33:05 - 00:37:21 - Impact of Entrepreneurship on Family and Personal Life00:37:21 - 00:41:06 - Raising Entrepreneurial Children00:41:06 - 00:50:02 - Reflecting on Angel Investing00:50:02 - 00:58:59 - Charity Work and Personal Fulfilment00:58:59 - 01:08:21 - Life Philosophy and Future Goals

Bill Flagg spent 20 years building 5 incredibly successful tech businesses, then unexpectedly sold them all. To his own surprise, the thrill of building businesses faded, and he found himself craving a pause, a chance to become a beginner again and enjoy the simple things in life. Two years ago, Bill moved with his family from Colorado to Portugal with no plans of returning anytime soon. Today we discuss this transformation, his craving for inspiration, creativity, simplicity, and soul-nourishing experiences. Connect with Bill Linkedin: https://www.linkedin.com/in/bflagg/_____________________________________________________00:00:00 - 00:03:36 - Introduction and Background 00:03:36 - 00:04:31 - Transition to Sabbatical 00:04:31 - 00:06:24 - Loss of Passion and Creativity 00:06:24 - 00:07:45 - Embracing a Pause for Creativity 00:07:45 - 00:11:11 - Living with Uncertainty 00:11:11 - 00:16:16 - Rediscovering Life in Europe 00:16:16 - 00:19:33 - Letting Go of Past Identities 00:19:33 - 00:26:18 - Challenges with Possessions and Ownership 00:26:18 - 00:29:03 - The Root Cause of Post-Exit Struggles 00:29:03 - 00:31:13 - Embracing Retired Life 00:31:13 - 00:31:38 - Family Perspective and Legacy 00:31:38 - 00:33:22 - Final Thoughts

Tony Kula. He has built three businesses, exiting his first in his mid 20-s and spending two decades turning the next into a video distribution powerhouse, which he sold six years ago. His latest venture, MeetYoo, skyrocketed during the pandemic, but faced serious challenges afterward, prompting Tony to reassess his priorities. Now he's an advocate for healthy living, an Ironman athlete and is finding his new purpose through angel investing and writing. In this episode, we explore his three decades of post-exit lessons and his uniquely European take on work-life balance._____________________________________________________00:00:00 - 00:03:12 - Introduction and Overview of Exits 00:03:12 - 00:06:28 - Building and Selling MVC 00:06:28 - 00:12:52 - Reflections on Investment and Entrepreneurship 00:12:52 - 00:15:54 - The Impact of Personal Transformation and Pandemic 00:15:54 - 00:23:35. Angel Investing and Adapting to New Roles 00:23:35 - 00:32:13 - Personal Growth and Reflection 00:31:13 - 00:35:18 - Ongoing Pursuit of Purpose and Legacy

Shane Neman successfully built and exited two iconic businesses: JoonBug, a digital events powerhouse, and EZ Texting, the largest business SMS software platform in the US. Today, he manages a substantial real estate portfolio, invested in over 50 startups, and authored the book called Nightlife Lessons: How I Conquered the Business of Partying with Tech. In this episode, Shane reveals the secrets behind his transition from the daily stress of running two businesses to achieving contentment and impressive financial success. Connect with Shane: Website: https://www.shaneneman.com/ X: / shaneneman LinkedIn: / shaneneman Instagram: / shaneneman YouTube: / @shaneneman Facebook: / nemanventures_____________________________________________________00:00 - 03:36 Introduction and Background 03:37 - 07:08 Early Entrepreneurship and Challenges 07:09 - 10:12 Growth and Evolution of JoonBug 10:13 - 13:02 Transition to EZTexting and Subsequent Sale 13:03 - 14:51 The Burnout and Decision to Exit EZTexting 14:52 - 21:05 Post-Exit Introspection and New Ventures 21:06 - 28:52 Investment Strategies and Mistakes 28:53 - 35:41 Personal Growth and Health Focus 35:42 - 42:54 Maintaining Balance and Family Life 42:55 - 51:07 Philosophical Insights and Ethical Reflections 51:08 - 57:21 Decision-Making and Lifelong Learning 57:22 - 01:04:51 Final Reflections and Outro

Ben White. He's sold three businesses so far for $80M, $88M and $800M. It was the last exit 16 years ago that hit him hard. What followed was a dark decade filled with divorce, addiction and significant financial losses. However, today Ben is the happiest he's ever been. In this episode we discuss his hard-earned lessons on happiness, why he started his fourth business now and walked away from running his VC firm. _____________________________________________________00:00 - Introduction 01:33 - The impact of the 2008 exit and the dark decade 03:10 - Initial feelings and challenges post-exit 05:32 - Divorce and addiction struggles 07:51 - The sudden change in life without a business to run 09:55 - Coping mechanisms and poor investment decisions 11:57 - The importance of grounding oneself after a major life change 14:02 - Reflections on making poor decisions and facing addiction 16:10 - The importance of dealing with significant life events 18:08 - Advice to the younger self: taking time off and dealing with addictions 19:53 - The impact of personal struggles on family 21:54 - Strategies for being present and engaging with children 24:02 - The role of family in finding happiness 26:02 - Recognizing the importance of real friends and authentic relationships 28:20 - The danger of wealth changing social dynamics 30:25 - The importance of staying grounded and real 32:23 - Transition from VC firm back to entrepreneurship 34:20 - The creation of UP and its vision 36:19 - The importance of having a clear purpose and passion for work 38:21 - Changes in views on wealth and financial freedom 40:35 - The role of money in achieving happiness 42:22 - Learning to appreciate simple pleasures in life 44:12 - Finding happiness in nature and everyday moments 46:26 - Teaching kindness and empathy to children 48:29 - The role of nature in achieving a balanced and happy life 50:25 - The desire to leave a meaningful legacy 52:26 - The importance of helping others and making a positive impact 54:33 - Reflections on how to be remembered 56:29 - Parenting strategies and guiding children towards real values 58:28 - The importance of independence and real-world experiences for children 01:01:04 - Balancing drive and contentment in personal and professional life 01:03:26 - The journey to finding personal happiness 01:05:20 - Combining contentment with entrepreneurial drive 01:07:30 - Final thoughts on balancing life, work, and happiness

Alex Bean has recently sold his fintech company Divvi for $2.5 billion. Today, he runs a VC firm called Tandem and has written a book titled The Factory for Good on turning your life into a force for positive impact. In this episode, we explore the emotional complexities of wealth and discuss why he envies those still in the rat race, how he earns his sleep, finds purpose and talks to his kids about wealth._____________________________________________________00.00 Introduction 01:57 The Post-Exit Emotional Journey: Pride, Excitement, and Unfulfillment 07:03 Transitioning to Venture Capital: Purpose and Fulfillment 13:59 Challenges and Lessons After Selling a Company: Insights for Entrepreneurs 30:31 Purpose, Values, and Success: Building a Meaningful Post-Exit Life 33:00 Legacy and Impact: Creating a Lasting Influence 53:31 Finding Your Superpower: Leveraging Strengths for Post-Exit Success

CK Kim is a serial tech entrepreneur who recently completed his second exit, exceeding $510M. To recover, CK took a year -long sabbatical. During his travels, he reflected on his experiences and distilled his insights into clear and powerful ideas. In this episode, we discussed the importance of soul search, secrets to post -exit happiness, the impact of the sale on his young family, and the excitement of supporting start-up founders. CK Kim's website: https://www.changkim.me/ More about CK's sabbatical leave: https://www.linkedin.com/posts/changkim_on-sabbatical-activity-7195448168396861440-zcvW/?utm_medium=member_desktop&utm_source=share _____________________________________________________00:00 Introduction 00:50 The Journey of Starting and Selling Two Companies 04:55 Transitioning from Founder to Employee 09:15 Life After the Exit: Rest and Recovery 23:00 Long-Term Thinking and Finding the Right Path 29:15 The Importance of Soul Searching and Rest 33:40 The Power of Conversations 40:05 Finding Meaning and Purpose 43:00 Managing Imposter Syndrome 48:45 The Fulfillment of Parenthood 51:30 Creating a Platform for Sharing Wisdom

Preston Rutherford. His company was sold in a 9-figure exit 5 years ago. A couple of years later, the combined company had a 10-digit IPO. But Preston wasn't there to experience it. While he regrets exiting too early, he acknowledges that the exit propelled him into an intense personal growth journey. In this episode, Preston shares how he learned to appreciate what he had, communicate more vulnerably and understand the compounding effect of experience, skills, and relationships. Connect with Preston: LinkedIn: https://www.linkedin.com/in/prestonr/____________________________________________________(00:00:00) Intro (00:01:11) Welcome (00:01:50) Reason behind starting Chubbies (00:02:13) Reasons for leaving Chubbies (00:03:52) Consequences of leaving the business (00:04:42) Contemplations on the decision to leave (00:05:24) Regret on leaving the business (00:06:16) The pursuit of greener pastures (00:07:14) Learning from the decision to leave (00:08:33) Journey back to the zone of genius (00:09:20) Overcoming burnout and healing (00:12:20) Facing personal and professional challenges (00:13:47) Realizations and personal growth (00:14:21) Finding out personal identity (00:17:41) Coming to terms with self worth (00:18:34) Working on personal development (00:21:13) Understanding the definition of success (00:23:14) New definition of success (00:25:09) Search for self-worth (00:26:09) Current definition of success (00:27:25) Professional journey and success (00:28:10) Reflections on personal life (00:29:14) Personal life and family (00:30:06) Juggling work and family life (00:30:21) Joy and personal life reflections (00:33:02) Work and self-identity (00:35:25) Progress since leaving previous company - Chubbies (00:40:01) Relationship with wife amid business challenges (00:44:16) Balancing dreams and practicality in business (00:47:32) Transition period after Chubbies and preparations for new business (00:48:45) How he wants to be remembered

Four years ago Gil Eyal sold HYPR - a software business which revolutionized the way big agencies and brands run influencer marketing. Today, Gil runs a venture capital firm which adds value to consumer tech companies by bringing celebrities onboard. In this episode, we discuss overcoming a post-exit identity crisis, building a personal brand, dealing with celebrities and becoming an investor. Connect with Gil: Linkedin: https://www.linkedin.com/in/gileyal____________________________________________________(00:00:00) Intro (00:01:17) Welcome (00:09:33) The role and impact of Influence Marketing (00:14:41) The struggle and lessons of selling a company (00:16:55) Dealing with separation and moving on after selling (00:19:38) Retaining financial interest and future prospects (00:20:37) Reflections on past experiences as a founder and transition into an investor (00:24:02) Advice for someone selling their company (00:26:37) Building personal brand post-exit (00:28:25) Reflecting on mentorship and investment choices (00:30:06) Balancing relationship with personal life post-exit (00:32:46) The impact of investing on mentorship (00:35:06) The effect of an exit on family (00:37:33) Prospects for children becoming entrepreneurs (00:38:31) Future as an investor (00:39:10) Challenges in the investment industry(00:39:33) The challenges of being an investor(00:41:20) Personal risk in investments (00:43:24) Advice on angel investing (00:45:32) Joining a group and surrounding yourself with experts (00:46:17) What to do after an exit (00:48:02) Changing your lifestyle post-exit

Craig Follett built Universe.com, a social marketplace for events, and sold it to Ticketmaster in 2015. Following the sale, Craig grew the business 30-fold and took the company global before leaving in 2019. He then found his calling in building Peggy.com, a secure marketplace for buying and selling investment-grade art. In this episode, Craig shares how and why he found his post-exit mission in making incredible art affordable to everyone. Discover more about Peggy: https://peggy.com/____________________________________________________(00:00:00) Intro (00:01:11) Welcome (00:03:03) Post-Business Life and Feelings (00:03:46) Sabbatical Experiences and Growth (00:06:12) Creativity and Business Associations (00:07:42) Brainstorming New Business Ideas (00:08:37) Development of New Business Idea (00:09:16) Understanding the Art Industry and Seeing Opportunities (00:13:16) Motivations behind Starting a Business (00:16:54) Desire for Social Impact in Business (00:18:08) Purpose-driven Business Endeavor (00:19:29) Reflections on Money and Wealth (00:20:35) Sharing Success with Loved Ones (00:21:51) Following Motivation for Creativity (00:22:18) Money as a Resource and Scarce Time (22:52) Self Identity and Growth Reflection (23:48) Imposter Syndrome in Entrepreneurs (24:04) Separating Personal Identity from Business (26:03) Investment and Detachment in Business (27:12) Rediscovering Self Identity after Exiting Business (27:58) Moral Acceptability of Pursuing Self-Interest in Business (29:19) Personal Growth and Self-Improvement Plans (30:15) Relationship with Spirituality (32:00) The Transition from Entrepreneur to Employee (34:07) Alternative Investment and Art (34:56) The Impact of Art on Society (36:38) The Role of Suffering in Personal and Business Success (41:33) The Importance of Pleasure and Satisfaction (43:51) Future Plans for Peggy and Disruption in the Art Industry (00:45:41) Definition of Canon and Role of Auction Houses (00:46:39) The Use of Blockchain for Technology (00:47:38) Future Plans and Legacy (00:49:02) Discussion on Mental Health and Childhood

Dave Hersh. He sold his company through an IPO 13 years ago, then spent several years with the VC firm Andreessen Horowitz.Today, Dave is more fulfilled and productive than ever.He credits a 10-year existential crisis that led to his “deep reprogramming” and “rebirth.”Today he talks to us about finding true self, sovereignty, and inexhaustible fuel sources. Connect with Dave: Website: https://www.davehersh.com/ Reignition - Book by Dave Hersh: https://www.amazon.com/Reignition-Transforming-Startups-Breakout-Winners/dp/1639090347 _____________________________________________________(00:00:00) Intro (00:01:21) Welcome (00:01:33) Life After Selling the Company (00:02:05) The Founding of Jive (00:04:24) Changing Trends in Digital Communication (00:05:14) The Challenges of Scaling Up (00:06:02) Life After Leaving the Company (00:08:16) Dealing with Identity Crisis (00:09:12) The Hoffman Process (00:10:46) The Art of Accomplishment (00:13:20) The Long Process of Reinvention (00:15:36) The Need for Inner Work and Transformation (00:16:37) Overcoming Entrepreneurial Struggles (00:18:01) Trying to Reconstruct Past Success (00:19:26) Finding Clarity and Direction (00:21:01) The Process of Transforming Identity (00:23:00) The Liminal Space Between Old and New Self(00:24:43) The Wilderness and Benefits of Being a Ghost in Between Worlds (00:25:20) Transition from Jive to Andreessen Horowitz (00:33:30) The Decision to Leave Venture Capital (00:35:31) Acquiring Businesses and Understanding Their Core (00:38:15) The Art of Identifying and Peeling Away Non-Core Activities (00:42:30) The Transformative Power of Returning to Your Core (00:43:55) Bounce Back Post Acquisitions and Restructures (00:44:12) Experimentation for Growth & Financing (00:45:24) Transforming into Purpose-Driven, Disciplined, and Strong Culture Businesses (00:46:08) Building a business that matters (00:53:00) Personal definition of success (00:54:33) Choosing the right people to surround with (00:57:29) Reimagining the idea of a company (00:58:38) Personal transformation and rebuilding (01:03:28) The trend of the creator economy (01:04:52) Optimism for younger generations (01:05:58) A perfectly fulfilling life (01:06:32) Discussing happiness and joy (01:07:26) Rating personal fulfillment (01:08:33) Advice after selling a company (01:09:16) Importance of inner work (01:09:55) What keeps one up at night (01:10:19) Discussing personal divorce (01:11:33) How one wants to be remembered (01:12:11) Anticipation for upcoming book

Mike Pollack sold his third business 6 years ago and has since, through trial and error, crafted a unique formula that balances happiness with a high likelihood of continued business success. In this episode, he shares this formula with us, delving into how to identify your true zone of competence, release control, and master the art of letting go._____________________________________________________(00:00:00) Intro (00:01:25) Welcome (00:01:41) LinkedIn Profile of Mike (00:02:24) Discussing Mike's identity (00:03:18) Mike's experience after selling his business (00:07:35) Mike's experience on exiting business (00:10:10) Mike's perspective on initiating a startup (00:11:01) Being a part of a startup team (00:13:34) Traumatic experience of building a company (00:18:52) Missing the entrepreneurial experience (00:20:50) Discussions on Mike's new venture (00:21:25) Two types of approaches to problem-solving (00:24:03) Post-idea creation process (00:27:07) Role of passion and motivation in entrepreneurship (00:30:38) Trauma in starting a new venture (00:33:36) Defining success in present day (00:38:16) The journey from chasing status to chasing happiness (00:41:35) Balancing entrepreneurship with parenthood (00:42:22) Starting the M&A Process While Having a Newborn Baby (00:43:34) Balancing Work and Life and Aiming for a Healthy Business Structure (00:44:57) Striving for a Balanced Life while Building a Business (00:47:43) Implementing Business Plan While Being Parents of Young Children (00:49:31) Dealing With Wealth and Financial Success (00:51:57) Utilising Wealth and Managing it With Responsibility (00:53:37) Using Wealth to Accomplish Goals and Support Causes (00:54:44) Experiencing Economic Anxiety and Addressing Guilt (00:56:05) Being True to yourself, Leaving Things Better than Found, and Being a Good Human (00:57:47) Using Means to Empower Others and Improve the World (00:59:10) Integrity as a Core Value (01:00:27) Balancing Parenthood and Founding a Company (01:00:54) Working to Pay it Forward (01:01:04) Entrepreneur's Approach and Zone of Genius (01:01:55) Spirituality and its role (01:04:58) Advice for a business post-sale (01:08:01) The introspective work founders ought to do (01:09:13) Shifting from identifying as a founder to a larger role (01:14:05) The role of tech post-COVID (01:18:34) Level of fulfillment (01:20:09) Legacy and how to be remembered

Today's guest has chosen to remain anonymous to ensure the utmost authenticity and vulnerability in sharing his story. Four years ago, he fully exited his business and now describes his life as post-economic. He realized he had a money addiction his entire life and took a radical step to address it—he avoids any money-making activities, focusing instead on activities that increase his energy. In this episode, we focus on how to know what we truly want and whether we have enough. Beyond The Finish Line: https://btfl.org/ Retired Founder Twitter: https://twitter.com/RetiredFounder_____________________________________________________(00:00:00) Intro (00:02:09) Reasoning behind anonymity (00:03:43) Business selling journey (00:06:15) Post-business selling life (00:08:06) Personal discovery and growth (00:09:50) The struggles in retirement (00:11:10) Unraveling the unhappiness (00:14:00) Breaking bad habits (00:17:35) Further self-discovery and improvement (00:18:56) Reflections on the pursuit of money (00:19:45) The concept of "enough" money(00:20:28) The struggle with money addiction (00:21:08) Forming an anonymous support group (00:21:35) Description of 'Beyond the Finish Line' group (00:22:10) Dealing with loss of work structure after exit (00:25:04) Choosing to separate self from money making endeavors after exit (00:30:00) Emotional connections to the sold business and the importance of being needed (00:35:16) The quest for being useful and finding satisfaction (00:37:03) Setting up for inviting good things into life (00:38:59) Overcoming post-exit blues and the journey to self-enlightenment (00:40:41) The realization that happiness is not equal to money (00:41:43) The comfort zone and yearly expense (00:42:27) Discomfort and societal views on financial pursuit (00:47:07) Potential of finding a new purpose with economic upside (00:51:14) Balancing personal monetary gain with sustainable solutions (00:53:28) Personal hobbies and recreational activities that energize (00:57:59) The struggle with too much freedom (01:00:17) The process of energy management (01:01:57) The sense of purpose and fulfillment through contribution and growth (01:03:16) Art of Disappearing (01:04:15) Views on Legacy (01:05:06) Thoughts on Inheritance (01:07:03) Mental Health Discussion (01:08:11) Silent Retreats and Psychedelics Exploration (01:10:03) Vision of the Four False Gods (01:10:47) Wrap Up and Final Advice

Laurent Vernhes spent 20 years shaping Tablet Hotels into a tech and luxury travel icon, culminating in its acquisition by the discerning Michelin Group 4 years ago. Now, Laurent is channeling his expertise and refined taste into launching a wine company committed to delivering the world’s finest wines at fair prices. In this episode, we explore the art of building luxury brands, quality obsession, and treating business as an artistic endeavor. A deep and independent thinker, Laurent shares his life lessons with us in a beautifully vulnerable way._____________________________________________________(00:00:00) Intro (00:01:18) Introduction and Greeting (00:01:30) About Laurent's Thought Process and Life Experiences (00:01:50) Journey of Building Tablet Hotels (00:02:20) Motivation Behind Starting Tablet Hotels (00:04:12) Importance of Convincing People in Business (00:07:15) Challenge of Funding (00:09:55) Growth and Business Model of Tablet Hotels (00:10:15) Difference in Business Approaches (00:11:04) Brief on LVMH & Bernard Arnaud (00:12:00) Methodology of Growing Businesses (00:14:07) Process of Shift to the Next Business Venture (00:16:18) Process of Looking Inward For Growth (00:19:09) Decision on Regaining Entrepreneurial venture (00:20:46) Intersection of Art and Commerce (00:22:57) Art, Wine, and Commerce (00:23:24) Structure of the Wine Industry (00:24:18) The art of wine making (00:26:04) The drawback of removing alcohol from wine (00:26:26) Scouting wine artisans globally (00:27:58) Mission to help people discover good wine (00:31:30) Learning about the complexity of wine distribution in the US (00:34:38) Money as a means of freedom (00:37:14) Engaging with life through entrepreneurship (00:40:37) On becoming an angel investor (00:42:51) Self-growth and patience (00:45:33) Creating something desirable (00:46:29) Fulfillment and Happiness (00:49:45) Fulfillment as Satisfaction (00:53:30) Personal Growth and Intent (00:57:39) About New Business MV Wine (00:59:41) Engaging with Life When Awake (01:02:06) Dealing with Unfiltered Challenges (01:05:32) Creating a Vehicle to Express Creativity (01:07:31) Perception of Selfishness (01:08:07) Conclusion and Gratitude

Keith Smith has spent 2 decades building 5 companies and raising 2 children as a single dad. A deep and original thinker, he chose to confront his post-exit mental health issues head on. In this episode, Keith openly shares his insights, therapy takeaways and how he found his latest mission in empowering creators with his innovative AI tools._____________________________________________________00:00:00: Intro 00:01:27: Welcome 00:01:50: Discussing Keith's life-changing moment in 00:02:15: Discussing Keith's background 00:03:28: The impact of wealth on Keith's mindset 00:06:09: Developing empathy and changing mindset about wealth 00:06:44: Balancing business and parenthood 00:09:26: Learning to share wealth and outcomes 00:10:17: Adjusting equity in business partnerships 00:12:12: Motivation behind starting the first company 00:13:24: Views on wealth and societal impact 00:14:27: Personal growth and the importance of self-evaluation 00:16:47: Experience as a single parent while building a business 00:19:55: Children's involvement in the business 00:20:54: Insights from business successes and failures00:22:08: Reflection on experiences as a repeat founder 00:24:44: Importance of mental health before and after an exit 00:26:11: The therapeutic journey and self-discovery 00:29:42: Spirituality and mental health in personal development 00:32:10: Addressing mental health stigma, especially among entrepreneurs 00:34:23: Transitioning from ad tech to fintech, and to AI 00:36:14: Building impactful socio-tech solutions 00:39:58: Launching Meforyou.ai and the problem it aims to solve 00:42:07: Addressing the "loneliness epidemic" through AI 00:42:47: Discussing Behavioral Changes Toward Media Consumption 00:43:23: Synthetic relationships for the disconnected and lonely 00:43:57: How AI Personas can potentially be used for Education 00:45:15: Potential Use in Entrepreneurship and Mentorship 00:46:10: Evolution of Company's Features and Starting Point 00:47:21: The Future Use Cases for AI Personas 00:49:04: Personal Impact and Civic Mindedness 00:50:16: Personal Goals and Successful Outcome 00:53:04: Transition after Selling Company, Imposter Syndrome 00:56:02: Recognizing the Imposter Syndrome in Others, Importance of Spreading Opportunities 01:00:02: Systemic Biases in Society 01:01:03: Personal Therapy and Self-Sabotage 01:02:47: Discussing personal life and struggles 01:03:07: Intentions and personal reflections 01:03:37: Choosing the people to have around 01:04:52: Working with a team and personal dynamics 01:06:56: Dealing with breakups and personal life 01:07:10: Dating apps and searching for a partner 01:09:13: Telling a story, finding a fit and blending energies 01:09:21: Sense of purpose and believes 01:10:38: Psychedelics and taking new paths 01:11:06: Level of fulfillment 01:13:14: Raising children and developing relationships 01:16:00: Importance of hobbies and reshaping identity 01:18:16: Hobby of one wheeling 01:19:20: Most important lessons learned since the first life changing exit 01:20:37: Impactful lessons from children 01:22:47: Reflections on parenthood and self-improvement 01:23:06: Desire to make a societal impact 01:24:15: Vision for the future and overcoming age 01:25:17: Closing remarks and farewell

Connor Tomkies. He spent 8 years growing and selling SupportNinja, his global talent acquisition firm. Now he focuses on buying great businesses to scale them for exit. This episode delves into Connor’s exit experience, why he prefers to buy a significant portion of a business over angel investing, and how helping out his extended family members turned out to be the most rewarding use of his exit wealth._____________________________________________________Timestamps: 00:00:00: Intro 00:01:16: Welcome 00:01:26: The sale of Support Ninja 00:02:42: The experience of selling a company 00:03:08: Lessons learned from selling the company 00:09:48: The start of Operator Equity 00:10:10: How Operator Equity works 00:12:01: Explanation of EOS (Entrepreneur Operating System) 00:14:22: Experiences with EOS and why it was chosen 00:17:01: Ambitions for Operator Equity 00:17:15: Why Operator Equity was started 00:18:11: Personal love for inception and growth of a company 00:19:27: Investment in mature companies 00:20:33: Managing the creative impulse with mature companies 00:21:11: Beginning of Operator Equity journey 00:21:26: Looking ahead: The future of Operator Equity 00:22:15: Reflections on the impact of ego in business 00:23:04: The notion of fleeting success and the value of the journey 00:23:43: The struggle of self-identity post exit 00:26:13: The evolution of thoughts about money and wealth 00:28:24: The challenges and fears related to sudden wealth 00:31:06: Caution around extending financial security to others 00:31:45: Uncertainty in defining personal success after exit 00:33:22: The impact of financial success on personal relationship 00:35:45: Thoughts on sense of purpose post business exit 00:37:55: Avoiding guilt through conscious actions in business 00:39:56: Managing imposter syndrome and motivation 00:43:02: Expectations and understanding of success from parents' perspective 00:43:55: Discussion about stepping down and operator equity 00:44:23: Thoughts on raising future children and entrepreneurship 00:45:35: Talks on operator equity and investments 00:47:24: Inquiry over work-life balance 00:48:42: Question on personal legacy 00:49:50: Conclusion and best wishes for future projects

Sriram Gollapalli. After selling his software as a service business 8 years ago, he spent 6 years working with an acquirer before embracing his new found freedom. His calling? Investing and fostering a community of like minded investors. This episode delves into Sriram’s post exit journey. Including an introspection retreat, angel investing and the challenges of estate planning._____________________________________________________Timestamps: 00:00:00: Intro 00:01:10: Welcome 00:01:19: Discussion about the sale of ILab's operation system 00:01:37: Discussion about the treatment of staff post-sale 00:01:46: Discussion about the bootstrapping process 00:01:56: Discussion about life post-exit 00:02:09: Reflection on change post-exit 00:03:01: Discussion about the financial aspects post-exit 00:03:12: Discussion about managing time after selling the business 00:03:57: Discussion about how the exit was structured 00:05:10: Discussion about joining the buyer 00:05:34: Reflection on being an employee post-exit 00:06:28: Discussion about running operations for iLabs 00:07:10: Discussion about being a creative person 00:07:39: Discussion about motivations for starting a new business 00:09:14: Reflection on the entrepreneurial journey 00:09:19: Discussion about the creation of the Longangle community 00:10:31: Discussion about the growth of the Longangle community 00:11:01: Reflection on what Longangle gives to the founder 00:13:00: Discussion on angel investing 00:18:33: Reflection on angel investing as a financial strategy 00:19:46: Reflection on time spent on angel investing 00:20:09: The Balance of Time: Mentoring, Deal Flow Sourcing, and Personal Life 00:20:29: After Exit Stage: Opportunities and Challenges 00:21:46: The Unexpected Time Investment in Startups 00:22:04: The Impact and Limitations of Being an Angel Investor 00:22:25: The Long Game of Angel Investing and the Consequences of Fundraising 00:23:16: Investment Outside of Angel Investing 00:24:37: Diversification of Portfolio: Real Estate and Broad-based Indices 00:25:11: The Desire for Simplification in Investments 00:28:19: Community Involvement: Engaging in the DC Tech Scene 00:28:58: Entrepreneurship Education for the Younger Generation 00:29:20: The Concept of "Ikigai": Defining Purpose and Intention 00:30:48: Aspirations for the Future: The Drive for Building 00:33:04: The Influence of Wealth on Time Allocation 00:34:17: Reflective and Introspective Retreats 00:36:36: The Impact and Responsibility of Wealth 00:38:17: Regrets and Reflections on Selling a Business 00:39:37: Post-Exit Mental Health: The Need for Therapy 00:41:31: Consequences of quitting and firing 00:42:32: Thoughts on Spirituality and Culture 00:44:06: Personal Growth Strategy 00:45:16: Advice for business sellers 00:49:36: Importance of Health 00:50:35: How fulfilled are you? 00:52:43: Surrounding oneself with the right people 00:55:26: Recreational activities and building networks 00:55:57: Legacy and How to be remembered

Ari Katz teamed up with his celebrity doctor wife to create and sell one of the largest dermatology chains in the US. The exit afforded him the time and resources to explore his longstanding obsession with mental health. Ari’s new purpose? To revolutionize mental health care by advancing the psychedelic medicine movement. In this inspirational episode, Ari opens up about his journey from business exit to a life filled with meaning and fulfillment, driven by a powerful new purpose._____________________________________________________ Timestamps: 00:00:00: Intro 00:01:18: Welcome 00:01:49: Ari's previous dermatology business 00:02:34: Partnership and business dynamics with his wife 00:10:37: Selling the business 00:13:56: Post-exit reflections 00:19:05: Mental health 00:21:30: Decision to seek help for mental health 00:21:44: Overcoming Depression and Anxiety 00:24:01: Discovering Natural Alternatives to Conventional Medications 00:24:47: Utilising Financial Freedom for Personal Growth 00:26:26: Facing the Second Mountain - Shifting the Focus from Personal to Community Centric 00:27:13: Launch of the new company, Roar 00:28:11: The Effect of Psychedelics 00:31:30: Pioneering Psychedelics in the Startup Space 00:32:08: Exited Founders and Psychedelics 00:32:28: Taking a Leap into Psychedelics 00:33:10: Recommended Psychedelic for Beginners 00:36:11: Applying Neuroplasticity Through Psychedelic Medicines 00:38:31: Breaking Habits with Neuroplasticity 00:39:01: Ketamine Assisted Therapy and Ego Dissolution 00:40:34: Perspective on Psychedelics 00:41:35: Comparing Ketamine to Other Psychedelics 00:42:50: Concerns About Psychedelic Experiences 00:44:14: Discovering Psychedelic Medicine Through Media 00:45:37: Abuse of Psychedelic Drugs and the War on Drugs 00:49:52: The Impact of Politics and Divisiveness on Mental Health 00:51:26: The Risks and Stigmas Around Psychedelic Medicines 00:53:24: Exploring The Spiritual World with Psychedelic Medicines 00:56:58: Realizing Personal Potential and Striving for Self-Improvement 00:58:07: Re-evaluating the Definition of Success 00:59:10: Personal Success Definition 01:00:04: Business Success and Liquidity Event 01:01:22: Psychedelic Medicine and Personal Growth 01:02:07: New Business Announcement - Betterness 01:03:03: Current Medications and Supplements 01:07:06: Dealing with ADHD 01:13:46: Choosing People to Spend Time With 01:16:28: A Perfectly Fulfilling Life for Ari 01:18:12: Rating Personal Fulfilment 01:20:30: Perception of Wealth & Fulfillment 01:26:41: Perspective on Global Issues 01:28:39: Joy Derived from Family, God and Spirituality 01:32:13: Learning after Selling the Company 01:37:17: Striving for perfection and the role of luck in success 01:37:49: Importance of sharing entrepreneurial stories and overcoming challenges 01:38:14: Gratitude and appreciation for the podcast and its host, Anastasia 01:38:58: Concluding the conversation and future meeting plans

Matt Matros. After selling his healthy-food chain 10 years ago, Matt battled depression, anxiety, regret, and alcohol addiction. Yet, he didn't stop. He built and sold two more businesses, started a family, traveled the world, and became a highly respected voice in the business world. How did he overcome his struggles? With his signature humor and crystal-clear insight, Matt opens his heart to share with us the mental frameworks that propelled him forward._____________________________________________________ Timestamps: 00:00:00: Intro 00:01:24: Welcome 00:01:46: Sharing Personal Experiences and Lessons Learned 00:03:34: Recalling the Business Exit 00:04:10: Dealing with Post-Exit Struggles and Imposter Syndrome 00:09:09: Losing Identity after Selling the Business 00:10:25: Discussing New Opportunities and Future Outlook 00:12:13: The Impact of Selling on Creativity and Control 00:13:41: Reflecting on Regrets and Decisions 00:17:41: Returning to Self-Identity and Recovery 20:27: Discussing insecurities 00:20:49: Starting therapy 00:23:25: Experience with psychedelic drugs 00:28:57: Confronting alcoholism 00:33:03: Discussing life post exit 00:35:02: Sharing experiences on social networks 00:36:40: Discussing Ikigai concept 00:37:24: Using five love languages 00:39:12: Personal Insights and Relationships 00:40:01: The Influence of Family 00:40:18: The Significance of Goal Setting 00:42:11: Valuable Business Frameworks 00:43:31: Thoughts on Masking Authenticity 00:44:39: Level of Fulfillment 00:47:49: Important Business Lessons 00:48:59: Dealing with Depression and Staying Fulfilled 00:51:00: Motivations for Starting Businesses 00:52:42: Learnings from the Beverage Industry 00:55:01: Journey to Sparkling Water Business 00:55:13: Perspective on Wealth and Money 00:56:50: Future Personal Goals 57:06: Discussing family and being remembered 57:25: Wrapping up the interview 57:31: Therapy Thursday discussion 57:39: Appreciation for the podcast platform 57:58: Discussing LinkedIn posts 58:12: Talk of potential extended interview 58:25: Plans for future chats 58:35: Final Thanks and End of Conversation

Nick Telson-Sillett. He isn't just the famous host of "Pitch Deck," a go-to podcast for angel investing insights; he's a real-deal entrepreneur who, after selling his own company five years ago, decided to give back. Through Horseplay Ventures, he supports up-and-coming startups, and with his new software company, Trumpet, he's still in the game. Eloquent and open-hearted, Nick's here to share with us his personal wisdom and the lessons he's picked up from his numerous podcast guests._____________________________________________________ Timestamps: 00:00:00: Intro 00:01:07: Nick's life post business sale 00:01:18: The impact of money on happiness 00:01:27: Future plans for Nick 00:01:45: Thoughts on Angel investing 00:02:06: Lessons learned from business 00:02:53: How Nick wants to be remembered 00:03:05: Reflecting on the moment of selling the company 00:04:07: Personal crisis post-sale 00:05:13: Shift in idea of purpose after business sale 00:06:47: Self-discovery and ideation post-sale 00:07:44: Beginning of angel investing and new approach to stress 00:08:42: Motivations for continuing in business and advisory roles 00:09:14: Continuing desire to succeed and win 00:10:33: Discussion on the motivation for starting the first business 00:12:17: Exercise for financial freedom 00:13:36: Reflection on accomplishment of achieving financial goal 00:16:02: Thoughts on selling the company 00:16:35: Recollections of relief post-sale 00:18:12: Comparing past business motivation with current Trumpet business 00:19:10: Adjusting to new founder's financial objectives 00:20:07: Current motivation - learning and challenging self 00:20:41: Identity crisis post-business sale 00:21:56: Adjusting to new identity as a "startup guy". 00:22:36: Discussion about identity and starting of Podcast 00:23:13: Benefits of raising money from angel investors for early-stage businesses 00:24:06: Different formats for Podcast and its live nature 00:24:43: Purpose of starting the Podcast - Making angel investing less secretive 00:25:13: Success rate of the Podcast 00:26:02: Networking and forming friendships via the Podcast 00:27:32: Relation of Podcast and personal purpose post-business exit 00:28:57: Future plans post-trumpet days 00:29:24: Current Fulfillment rating 00:31:01: Changes in views towards money and wealth after exit 00:33:16: Importance of taking time for joy and presence 00:34:02: Discovering joy in walking 00:35:15: Health restoration post-exit during Covid00:36:38: Thoughts on imposter syndrome 00:39:10: Candidness about making mistakes and continuous learning 00:41:39: Mental health struggle during 'my night' and post-exit realization 00:43:40: Discussions on Purpose and Joy 00:44:51: Thoughts on Growing Up and Impacting the Community 00:46:56: Experience in Angel Investing 00:51:04: Current Position in Angel Investing 00:52:48: Thoughts on Why Founders don't Ask for Help 00:55:10: Reason Why Founders Become Angel Investors 00:59:44: Effect of Exit on Relationships with Friends and Family 01:01:06: Parents' Influence on Becoming an Entrepreneur 01:02:25: Choosing Who to Surround with 01:05:09: Friendship and energy 01:06:10: Thoughts on spirituality 01:09:07: Spirituality and mysticism separation 01:09:33: Contribution and purpose 01:10:42: Resolving the self-interest paradox 01:11:51: Closing remarks

Dan Reich has sold 4 successful companies so far, but he's far from finished. Retirement isn't in his plans anytime soon. What drives his relentless hunger, creativity and energy? How does he find such clear direction so quickly after each exit? In this episode, Dan offers an insightful look into his journey, sharing his practical wisdom in an honest and straightforward manner._____________________________________________________ Timestamps: 00:00:00: Intro 00:01:12: Welcome 00:01:15: Deep dive into money happiness 00:01:31: Exploring the concept of fulfillment 00:03:17: Discussion on the merits of angel investing 00:03:30: Sharing important lessons from a big exit 00:03:59: Advice post selling your company 00:04:37: Importance of introspection and how to stimulate it 00:05:20: Anastasia's method for choosing the people she surrounds herself with 00:06:03: An insight into Anastasia's first business venture and exit 00:07:37: Discussing life changing exits 00:09:57: Identifying the role of competitiveness and love for the game 00:12:01: A discussion on business growth and potential plans for future businesses 00:13:36: Reflecting on Anastasia's childhood and how it influenced her entrepreneurial journey 00:16:06: Anastasia's family background and her deviation from traditional career paths 00:19:39: Investigating patterns between successful entrepreneurs and their backgrounds 00:20:01: Different types of entrepreneurs and Anastasia classifying herself 00:21:15: The effect of Anastasia's first job on her entrepreneurial drive. 00:22:09: Overcoming Challenges 00:22:47: The Importance of Having a Purpose 00:23:17: Post-Exit Reflections 00:24:15: Post-Exit Depression 00:25:13: Realising Money Isn't Everything 00:26:15: Life and Death Situations 00:27:15: Importance of Building Companies with Amazing People 00:29:18: The Excitement of Seeing a Company Grow 00:33:44: Fulfillment from Impacting Lives 00:34:30: Achieving Success By Helping Others 00:37:33: Philanthropy Projects 00:41:13: Valuing Both Global and Individual Impacts 00:41:18: Personal Life and Hobbies 00:42:10: Current Daily Routine 00:42:48: Personal Prioritizations 00:43:38: Discussion on marketplace and venture studio 00:44:30: Discussion on Company Builders 00:45:14: Discussion on "Die with Zero" and living life based on experiences 00:46:25: Perspective on building businesses 00:47:42: Discussing the regret minimization framework 00:48:58: Discussion on societal treadmill and introspective questions 00:50:47: Perspective on being an entrepreneur 00:51:25: Events that shaped the speaker 00:53:12: Closing the interview

Boris Berenberg. He thought he hit the jackpot selling his bootstrapped cash-rich software business. Two years later, he's filled with bitter regret. In this candid episode, Boris gets real about his exit—what he wishes he knew then and what we can all learn now.LinkedIn Boris: https://www.linkedin.com/in/borisberenberg/Blog Boris: https://www.nothingeasyaboutthis.com/i-regret-selling-my-startup/_____________________________________________________ TIME STAMPS: 00:00:00 Intro 00:01:00: Beginning and Introduction 00:03:36: Discussing the Financial Side of Selling a Company 00:04:55: Talking About Financial Expectations and Reality After Selling a Company 00:07:33: Concept of "Dragon Mode" After Selling a Company 00:10:08: Discussing Reaction and Regrets After Selling the Company 00:13:25: Lessons Learnt and What Would Be Done Differently 00:16:03: Understanding Personal Values in the Context of Selling the Company 00:19:58: Mental Health Consequences for Founders Post-Sale 00:20:46: Looking Back - Starting the Business. 00:22:10: Effective team dynamics 00:22:54: Reaching a career apex at a young age 00:23:37: Starting on their own and consulting 00:24:24: Balancing job security with business growth 00:25:20: Shift in customer support ideologies 00:26:45: The motivations behind founding a company 00:27:21: The struggle with job autonomy 00:28:09: Working in an environment with almost complete autonomy 00:29:14: Perspectives on work-life balance and defining 'work' 00:31:26: Losing identity after selling the business 00:31:44: Contemplating next steps 00:34:01: Challenges of life as a digital nomad 00:36:33: Considerations on personal satisfaction vs financial security 00:41:11: Finding a happy place in specific environments. 00:42:15: The importance of networking and exploring future plans 00:44:21: Personal relationships and their effects post-exit 00:46:06: The benefits of the sale and finding a community 00:47:35: The loneliness pre-sale and finding community 00:48:24: Building acquaintanceships and friendships in new communities 00:49:47: Channeling dissatisfaction into motivation 00:50:46: Rating personal fulfillment 00:51:24: Searching for a sense of purpose 00:54:13: Discussing the difference in post-exit crisis for parents and non-parents 00:56:03: Desiring simple remembrance as a good family member 00:56:33: Aspiring to create a 'work playground' 00:57:37: Looking forward to future businesses and potential failures.

Aaron White and Anastasia Koroleva unpack the fascinating interplay of art and obsession within entrepreneurship. They share practical insights about the artistic nature of entrepreneurial ventures, the role of obsession in driving success, and the challenge of maintaining a strong sense of identity even after achieving success.Aaron and Anastasia delve deep into the concept of entrepreneurship being akin to longevity and transition. They unfold the compelling insights about the joys, struggles, and beauty of entrepreneurship, viewed essentially as an infinite game where the primary motivation lies in the joy of creation itself. Tune in and prepare to see entrepreneurship through an entirely new lens._____________________________________________________Timestamps: 00:00:00: Intro 00:01:05: Welcome 00:01:18: Aaron's post exit journey & lessons learned 00:02:30: Challenges faced in previous startup ventures 00:03:24: Discussing the concept of deals 00:03:33: Reflecting on personal motivations and growth mindset 00:06:02: Importance of customer satisfaction in business 00:07:33: Reflecting on personal growth and motivations (continued) 00:09:00: Struggles of identity crisis post exit 00:09:22: Transition to another startup venture 00:11:09: Reflections on successful exits and their impacts 00:13:04: Personal feelings post-successful exit 00:13:53: Strategies to handle identity crisis 00:16:26: Being obsessive about new things and learning 00:18:00: Allowing deep immersion in interests 00:18:48: Exploration of personal and business identity 00:19:00: Supporting growth in team members and building strong culture 00:21:21: Maintaining vision and focus in business 00:21:49: Discussing alignment with family members. 00:22:10: Family influence on entrepreneurship 00:23:05: Wife's support and influence 00:23:49: Lessons from parents 00:25:23: Did parent's expect entrepreneurship? 00:26:33: Entrepreneurship as a form of art 00:28:05: Channeling creativity in entrepreneurship 00:30:25: Advantages of sharing accomplishments 00:33:41: Embracing public storytelling 00:36:22: Why transition to VC? 00:40:28: Challenges with VC 00:40:58: Preference for Team Building 00:41:20: Challenges of being an angel investor 00:42:14: Balancing personal time with investment opportunities 00:42:34: Managing pressures and setting expectations 00:44:11: Overcoming an identity crisis through angel investing 00:46:18: Relationship with financial freedom 00:48:32: The paradox of entrepreneurship and financial focus 00:49:17: Wealth management strategies 00:51:45: Grappling with fulfillment and ambition 00:56:56: Choosing personal relationships intentionally 00:59:27: Overcoming the trauma of past stressful experiences in business 01:01:02: Building Better Teams 01:01:55: Overcoming Business Struggles 01:02:25: Balancing Responsibilities 01:03:46: Maintaining Health During Stressful Times 01:05:29: Increasing Ambition to Reduce Stress 01:09:35: Envisioning a Bright Future with Technology 01:12:01: The Importance of Post-Exit Healing 01:14:55: Sustaining a Healthy Day-to-Day Routine 01:16:38: The Struggle of Rest and Transition 01:19:14: The Challenges of Starting New Ventures After Exits 01:19:50: Preparing For Family Life. 01:20:26: Work-life balance discussion 01:21:45: Next big project criteria 01:24:52: The importance of product building over business model 01:28:35: Expectations for future success 01:29:01: How to be remembered

Bill Hudenko. A serial exited founder, clinical psychologist, university professor, self-taught programmer, and musician, Bill joins us today to share his personal and professional insights on life after an exit. Each of Bill's businesses, past and present, has been driven by a mission to heal others, rooted in a deep understanding of the human psyche. He is an incredibly warm, caring, and captivating individual who inspires and teaches us to become healthier and better people._____________________________________________________Timestamps: 00:00:00: Intro 00:01:13: Welcome 00:01:21: Discussing important lessons from business experiences 00:02:05: The correlation between happiness and money 00:02:39: Discussing worries and concerns 00:03:43: Things that bring joy in life 00:04:31: Self-definition and uniqueness 00:05:32: Future plans and goals 00:06:11: Discussing sense of purpose 00:06:48: Reflecting on personal legacy 00:07:16: Recognition of achievements and experiences 00:08:25: Source of motivation for impact 00:09:31: Importance of striving for positive impact 00:09:56: Discussing the morality of earning whilst serving others 00:10:52: Reflections on childhood and parents' expectations 00:12:23: Connection between entrepreneurship and mental health issues 00:15:37: Addressing mental health issues post-business sale 00:18:01: Relationship between spirituality and mental health 00:19:37: Personal insights into life purpose 00:22:25: Aspects of building personal relationships 00:24:24: Reflection on the role of luck in business and success 00:26:27: Influence of Success on Personal Attributes 00:27:37: Lessons of humility on the Entrepreneur journey 00:30:08: Dealing with guilt related to success 00:30:42: Discussing Impostor Syndrome 00:34:14: Dealing with failure and feelings of responsibility 00:34:47: Regrets related to past business decisions 00:36:33: Learning from business exits and realigning ambitions 00:38:12: Understanding of wealth and its impacts 00:40:29: Effects of business success on personal relationships 00:41:26: Defining personal success and failure 00:43:23: Reflections on undertaking business ventures 00:45:35: Initiation of the business, deep 00:47:53: Evolution of Business ideas and the birth of everpage.com 50:42: Discussion on increasing anxiety post-pandemic 51:06: Introduction of the "deep" app 51:32: Pivot towards mental health and meaningful connections 52:01: Discussion on kindred spirits 53:14: What activities are meaningful in speaker's personal life 54:23: Discussion on compassion, selfishness, and human connection 55:33: Link between hurt and transactional relationships 56:06: Steps towards becoming compassionate 57:01: Philosophical insight on selfishness and fulfillment 58:09: Thoughts on the concept of self, the illusion of independence 59:02: Speaker's mission on this planet.

Brett Gelfand. A second-generation exited founder, he has successfully built and sold a company, just like his dad. Now, they're in business together. In this episode, Brett shares with us insights from both his and his father's post-exit experiences, the keys to successful business partnerships, finding love, and thriving as a digital nomad._____________________________________________________Timestamps: 00:01:00: The early journey into business and entrepreneurship 00:01:22: Entering the cannabis industry 00:01:56: Decision to avoid traditional nine-to-five job 00:02:44: Becoming CEO at age 00:03:26: The drive to solve problems in the industry 00:04:19: Change in motivation after business exit 00:06:12: Shifting from a fear-driven approach to a passion-driven one 00:08:20: Considering other industries and opportunities 00:10:51: Decision to sell first business and focus on another 00:11:25: Feeling after selling first business 00:14:34: Shifting perspective on money and success 00:16:15: Parents' influence on entrepreneurship journey 00:17:26: Starting a business with father 00:19:24: Challenge and benefit of working with a family member in business 00:21:01: Decision to go into business with father and learning through the process 00:22:38: Growing up in a business-oriented family 00:23:21: Impact of business partnership on personal relationships 00:24:58: Parents' reaction to business partnership 00:25:33: Impact of financial freedom on happiness 00:28:14: Experience of travel and luxury after financial security 00:29:11: Reflection on the journey of building and selling a business 00:31:35: Learning lessons from the entrepreneurial cycle 00:35:21: Experience and benefits of globetrotting 00:43:39: The role of therapy in personal growth 00:44:36: Lessons from a Life Coach 00:57:18: Transitioning from Entrepreneur to Family Man 01:02:57: Preparing for Parenthood 01:03:39: How Brett Wants to be Remembered 01:05:23: Entrepreneurship as Freedom 01:06:13: Discussing personal freedoms and lifestyle 01:07:35: Reflecting on retirement and the necessity of growth 01:08:22: The role of financial success in personal growth and risk-taking 01:09:41: Investment philosophy and financial strategy 01:11:39: Closing the discussion and expressing gratitude