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-kaufman
PEF: https://pef.xyz/
Vine Ventures: https://vineventures.com

Connect with Anastasia: 
Linkedin: https://www.linkedin.com/in/anastasiakoroleva
X: @AnasKoroleva
Newsletter: https://www.exitparadox.com/blog
About Anastasia: https://www.exitparadox.com/about

Listen to Exit Paradox Podcast:
Apple Podcasts: https://podcasts.apple.com/us/podcast/exit-paradox/id1719806072
Spotify: https://open.spotify.com/show/7cC1er82lJBviXe6qjM158

Some exits, they just stop us in our tracks. Not because of the money or the business genius, but because of the radical personal transformation that followed. 

Dan Berger's story is one of those. Seven years ago, he sold social tables for around $100 million million dollars. And like so many of us, the exit cracked something open. The wealth, the time, the freedom. It didn't bring peace at first. It made things worse. Den spiraled into addiction, sex and porn. But he soon realized the pleasure they gave him was too fleeting, too empty. It did nothing to meet his real needs. That's when Den realized that his Exit wasn't just a big win. It was a chance to create something he'd never truly had. Real sense of belonging. 

Today, years later, he finally has it. He has finally built it. Then is a story of real courage. The courage to confront his darkest demons. Childhood trauma, bipolar disorder, Chronic anxiety. The patience and resilience to get to the root of his pain. 

This is one story you really don't want to miss.

00:00:00 Intro
00:01:55 Life After Selling Social Tables 
00:02:25 Loss of Belonging Post-Exit 
00:03:53 Failed Attempts to Recreate Work Identity 
00:05:05 Belonging & Addiction 
00:06:42 Why He Wasn’t Aware of His Needs 
00:09:43 The Crossroads Moment and Reinventing Identity 
00:13:23 Dan’s Framework for Belonging 
00:18:10 Can Our Belonging Archetype Change? 
00:22:43 Dan’s Belonging Tank Today 
00:25:02 How Dan Defines Belonging 
00:32:01 Sex Addiction and Its Roots in Belonging 
00:36:22 Getting Help: 12-Step Recovery 
00:37:54 Why No One Talks About Sex Addiction 
00:39:44 Loneliness, Belonging & the Male Crisis 
00:42:52 Raising Boys and Masculinity Today 
00:45:14 Switching Gears: The Financial Impact of Exit 
00:48:49 Die With Zero: A New Financial Philosophy 
00:53:23 Purpose, Not Just Experience 
00:56:00 New Venture: Offsite Retreat Venues 
00:57:38 Lessons from Social Tables to New Business 
00:59:12 Dan’s Business Archetype: Operator 
01:00:12 The Risks of Using Own Money 
01:01:19 Writing a Book: Process and Pitfalls 
01:03:20 What's Special About Dan's Book 
01:04:07 How Dan Wants to Be Remembered

Today’s episode is different. My guest isn’t an exited founder but she’s someone we all need.

Amy Castoro helps families have honest conversations about wealth—the kind most of us were never taught to have.

She shares practical tools from her firm’s 50 years of experience advising some of the wealthiest families in America. 

Her work focuses on the emotional side of money—how we build trust, protect our closest relationships, speak openly, and prepare the next generation to handle wealth well.

We talk about raising children with money and how to rethink our own relationship with it after a successful exit.

It’s one of the most useful conversations I’ve had. Amy’s views challenged my own.I hope it helps you as much as it helped me.

00:01:59 Amy’s Background & Work with the Williams Group

00:03:30 Why 70% of Families Fail at Wealth Transition

00:05:18 Trust, Communication & Heir Preparedness

00:08:18 How Early Should Kids Be Taught About Wealth?

00:10:31 Age-Appropriate Conversations About Philanthropy

00:13:17 Creating Motivation Without Financial Desperation

00:16:23 Responding to Kids Asking About Inheritance

00:20:35 Involving Children in Wealth Management Early

00:22:33 Teaching Kids to Say “No” & Handle Peer Pressure

00:26:44 Skills Young Heirs Often Feel They Miss

00:29:09 Should Children Be Encouraged to Be Entrepreneurs?

00:32:28 What If the Family Came into Wealth Late?

00:36:04 First Family Meeting: What to Discuss

00:37:28 Re-engaging the “Unmotivated” Youngest Child

00:40:29 Coaching vs. Therapy in Wealth Transition

00:41:41 Families with Young Kids: How to Start Early

00:44:33 Relationship Skills & Communication Patterns

00:47:06 Why the Skills That Build Wealth Won’t Transition It

00:48:20 Balancing Entrepreneurship & Parenting Post-Exit

00:50:39 Modeling Purposeful Wealth, Not Just Growth

00:54:36 What Successful Families Say the Purpose of Wealth Is

00:56:49 Defining Family Values Around “Education”

00:58:41 Reconciling Different Values in the Family

00:59:50 Allowance Strategies in Wealthy Families

01:01:38 Knowing When to Shift from Parent to Mentor

01:03:28 Creating & Living a Family Mission Statement

01:06:06 New Program: Next Gen Leaders

01:07:25 Common Mistakes Families Make Around Wealth

01:10:34 Should Families Hold Regular Meetings?

01:12:37 The #1 Shift Families Must Make for Success

01:13:38 Amy’s Recommended Books on Family Wealth

01:15:15 Final Thoughts: Preparing the Family for the Assets

My friend Jay Radia doesn’t just build businesses—he builds momentum.He’s a three-time tech founder and a prolific angel investor.Since his last exit two years ago, he’s been building Blissgrowth—a venture studio that partners exclusively with exited founders.

Why did he choose this path? What has he learnt so far? Was it the right move?

For a while, Jay also co-hosted The Joyful Entrepreneur Podcast—a top 10 show about success and happiness.Today, we explore how Jay is designing his venture studio not just for financial success—but for joy, purpose, and meaning.And what he’s learned from both his own journey and the many post-exit founders he works with.

_____________________________________________________
00:00:00 - Introduction
00:04:23 - Emotional journey post-exit
00:06:00 - Experiencing emptiness despite success
00:07:15 - Defining the Post-Exit journey (Pause, Reset, New Chapter)
00:08:15 - Avoiding the corporate trap post-sale
00:09:35 - Discovering he's not a CEO type
00:10:15 - Founding Blissgrowth and love for early-stage building
00:11:30 - Venture Studio vs Angel Investing and Accelerators
00:13:15 - Pros and cons of running a Venture Studio
00:15:15 - Team dynamics and focus of Blissgrowth
00:16:45 - Common misconceptions about Venture Studios
00:17:45 - How his studio compares to others
00:19:15 - Angel investing vs Venture Studio involvement
00:21:15 - Journey from emptiness to fulfillment
00:23:15 - Connecting with intuition through stillness and yoga
00:25:15 - Daily practices to cultivate inner clarity
00:26:60 - The power of quiet and introspection
00:28:15 - Rewiring mindset and deep inner work
00:30:00 - Changing his relationship with fear
00:31:30 - From fear to freedom and growth
00:33:00 - The psychology of purpose and contribution
00:34:15 - Observations on other exited founders and finding purpose
00:35:45 - Why decoding purpose is a unique journey
00:37:15 - Role of spirituality and Indian heritage in self-discovery
00:39:45 - Spirituality as a path to love and connection
00:41:15 - Overcoming skepticism and redefining success
00:43:15 - AI, intellect, and spiritual work
00:44:15 - Creating and renaming his podcast: Joyful Entrepreneur
00:46:15 - Why he paused podcasting despite success
00:47:45 - Lessons learned from podcasting
00:49:15 - The power of public self-expression for exited founders
00:50:45 - Normalizing post-exit struggles in the founder community
00:52:15 - Redefining success after financial freedom
00:53:45 - Jay’s 5-pillar framework for purpose
00:55:45 - How Blissgrowth aligns with his purpose
00:57:15 - Building to scale vs building to exit
01:00:15 - Should founders build with an exit in mind?
01:01:45 - Jay’s commitment to Blissgrowth long-term

Linda Abraham is one of the most extraordinary women I’ve ever met. She’s in a class of her own.She’s been navigating the post-exit world for 28 years, ever since her first exit.And what an exit it was: a 5X return to investors in just two years!She went on to lead her second company, comScore, from founding to IPO—building it into a global powerhouse in digital analytics, with offices in 23 countries.Today, Linda runs Crimson Capital, investing her family’s money in early-stage tech companies, and serves on several boards, including Tiger 21.But what blows me away most is that she built all of this while raising four children—and thoughtfully nurturing deep, loving relationships with each of them.This episode is about an extraordinary entrepreneur who managed to do it all—and built a life that’s not just financially successful, but deeply, holistically fulfilling.There is so much we can all learn from her!

00:00 - Introduction and reflections on Linda’s first business exit
03:34 - Selling Peregrine Technologies and emotional response
04:36 - Starting the next venture and skills assessment
05:55 - Creating comScore and early funding story
08:11 - Frugality and surviving the dot-com crash
10:30 - Pivot to audience measurement and analytics
11:36 - Selling data to financial institutions like Citadel
11:59 - IPO and financial outcomes for the team
13:00 - Motivations beyond money and public company growth
14:01 - Leaving comScore and reflections on career satisfaction
15:10 - Post-exit transition and board work
17:09 - Realizing need for a break and pulling back from overcommitment
18:19 - Shift to board advisory roles and family balance
18:49 - Motherhood and managing with four children
20:09 - Family-first values and support system
21:48 - Daily decision-making and sacrifices
24:49 - Health and lifestyle improvements post-exit
27:25 - Transitioning from entrepreneur to investor
29:01 - Challenges in board work and mindset shifts
31:18 - Finding joy and variety in board roles
33:42 - Investing in second-time founders and founder motivations
38:15 - Raising children with wealth and aligned values
40:50 - Reflections on adult children and family discussions
43:07 - Delaying wealth conversations and individual approaches
46:21 - Continuing involvement in husband’s new startup
48:04 - Evolving motivations and contribution style
49:42 - Creating balance through mindful time management
52:45 - Focus on impact and strategic contribution
56:12 - Mentorship, support, and satisfaction in giving back
57:60 - Work, family, community: expanded arc of purpose
59:58 - How Linda wants to be remembered
01:01:14 - Conclusion and farewell

My guest today is Adam Rossi. He sold his company, Platinum Solutions, 14 years ago and walked away with life changing wealth. But what hit him first after his exit was regret. We talk about how he came to terms with his new reality, searched for his new purpose, and dealt with losing his found identity. My favorite part of Adam's story is that he built his company with his wife, Leila, and their marriage didn't just survive. Building and selling the business, it actually got stronger through it. We talk about what Adam would do differently now that he's had 14 years to reflect. Adam's story is fascinating and full of hard won wisdom. I'm so grateful he shared it.

00:00:00 – Introduction & Adam’s Exit Story
00:01:06 – Why Exited Founders Make Bad Investors
00:05:15 – From Angel Investing to Private Equity
00:09:00 – Why Most Second Companies Fail
00:10:15 – Lessons from a Failed Acquisition
00:12:07 – Buying vs. Building a Business
00:14:34 – Regret After Exit and Finding New Purpose
00:17:27 – Sacrifice, Purpose & The Next Big Thing
00:20:18 – Impact, Meaning & Philanthropy Struggles
00:23:44 – Coaching Entrepreneurs as a Calling
00:25:18 – Why He Hasn’t Jumped into a Big Mission Yet
00:27:00 – Kids, Family, and Timing the Next Move
00:29:00 – Angel Investing: Rise and Decline
00:31:06 – The Illusion of Control in Angel Investing
00:32:35 – Advice for New Angel Investors
00:34:45 – Lifestyle Balance Post-Exit
00:36:00 – The Grind Years: 20-Hour Days and Stress
00:38:00 – Building a Business with His Wife
00:41:30 – Division of Labor and Complementary Skills
00:43:00 – Conflict Resolution in a Husband-Wife Team
00:44:45 – Why They Didn't Start a Second Business Together
00:46:15 – Raising Entrepreneurial Kids with Wealth
00:50:45 – The Only Real Passive Investing Strategy
00:53:26 – Life Rules: Wealth vs. Freedom
00:56:40 – Is Balance Between Mission and Freedom Possible?
00:58:45 – Mental Health After the Exit
01:01:00 – Why He Shares His Story Publicly
01:03:15 – A Book for His Kids and Maybe the World
01:07:17 – Will He Publish It?
01:09:41 – How Adam Wants to Be Remembered
01:10:36 – Closing Thanks & Final Reflections

Mike Brown's post-exit journey led him from chaos to clarity, but not right away. He had to go through a painful divorce, a business failure, financial losses and emotional turmoil.

Today we are talking about what he's learned and why he decided to dedicate himself to coaching. 

🔗 CONNECT WITH MIKE:
🎥 YouTube Channel - ‪@mbrown_co‬
🐦 X (Twitter) - https://x.com/mbrown_co
📸 Instagram - @mbrown.co
💻 Website - https://unbreakablewealth.com/👥
Linkedin -   /mikebrownactual  

TIME STAMPS:

00:00:00 – Introduction

00:00:37 – The Aftermath of Selling a Business

00:02:07 – Reality Hits: The Post-Exit Crisis

00:03:19 – The Connection Between Entrepreneurship and Divorce

00:05:00 – Chasing Achievement vs. Finding Purpose

00:06:40 – Could He Have Saved His Marriage?

00:08:33 – What’s Next After the Exit?

00:09:59 – Why Coaching and Why It Almost Didn’t Happen

00:10:34 – A Costly Distraction: A Failed Investment

00:12:30 – The Emotional Weight of Money and Investing

00:15:00 – A Brutal Financial Loss: Losing $100K a Month

00:18:00 – The Transition from Founder to Investor

00:20:15 – The Importance of Financial Safety Nets

00:24:15 – Balancing Risk and Stability

00:29:00 – The Concept of Wealth Beyond Money

00:30:06 – Unlimited Freedom vs. Purpose

00:32:03 – Defining Purpose and Service to Others

00:36:00 – The Danger of Retiring Too Early

00:40:00 – Lessons from Childhood: How Early Experiences Shaped His Drive

00:46:00 – Parenting and Entrepreneurship

00:52:25 – Post-Exit Traps to Avoid

00:57:45 – Rebuilding Structure and Identity After an Exit

01:06:00 – Final Lessons: The Power of Stillness

01:07:22 – How Mike Wants to Be Remembered

VCs notoriously avoid investing in married couples, fearing that personal conflicts could sink the business. 

Yet, the Lazerows defied that norm—building not just one, but two successful companies together, culminating in an $800M exit.

They didn’t just make it work; they mastered it—and then wrote a book about it.

Today, we’ll dive deep into what exactly they did to make it work—and what they wish they hadn’t.

TIME STAMPS:

00:00:01 - Introduction

00:00:14 - Learning from Failure vs. Success

00:00:27 - Building a Business as a Married Couple

00:01:08 - First Meeting and Early Impressions

00:02:30 - Life After an Exit

00:03:08 - Golf.com: The First Big Exit

00:06:58 - The Struggles of Entrepreneurship

00:09:14 - The Emotional Toll of Entrepreneurship

00:10:35 - Taking a Break After an Exit

00:11:14 - Was Their First Exit Life-Changing?

00:12:54 - Why Start Another Business?

00:14:31 - Entrepreneurship with Three Kids

00:16:47 - Why Entrepreneurs Keep Going

00:19:41 - Becoming Investors

00:23:20 - The Hardships Behind Entrepreneurship

00:28:17 - Coping with Post-Exit Stress

00:31:41 - Entrepreneurs and Mental Health

00:34:55 - Reframing Anxiety & ADHD as Superpowers

00:38:46 - The Dark Side of Entrepreneurship

00:44:01 - Work-Life Balance: Do They Have One?

00:48:01 - Michael’s Attempt at a Painting Career

00:50:12 - Filtering Opportunities

00:52:28 - Navigating Marriage After an Exit

00:55:15 - Raising Kids with Wealth

01:02:11 - Teaching Kids About Money and Responsibility

01:09:04 - The Purpose of Their Book

01:11:20 - Final Question: How Do You Want to Be Remembered?

🔗 CONNECT WITH KASS AND MIKE:

👥 Linkedin KASS - https://www.linkedin.com/in/kasslazerow/

🐦 X (Twitter) KASS -  https://x.com/kasslazerow

👥 Linkedin MIKE - https://www.linkedin.com/in/lazerow/

🐦 X (Twitter) MIKE -  https://x.com/lazerow

💻 Website (personal) -  https://www.kassandmike.com/

I📸 Instagram: https://www.instagram.com/kassandmike/

TikTok: https://www.tiktok.com/@UCgLzz0yep6lUaE5i62zMXTw 

🎥 YouTube Channel: https://www.youtube.com/@UCgLzz0yep6lUaE5i62zMXTw 

🔗 CONNECT WITH ANASTASIA: 

🎥 YouTube Channel - https://www.youtube.com/@UCaoC4W9E2Vopnkd-K3dOw7Q t

🐦 X (Twitter) -  https://x.com/AnasKoroleva  

📸 Instagram -  https://www.instagram.com/anastasiashoot

💻 Website -  https://www.exitparadox.com

🗞️ Newsletter - https://www.exitparadox.com/blog

👥 Linkedin -  https://www.linkedin.com/in/anastasiakoroleva

TikTok - https://www.tiktok.com/@anastasia.korolev7

My guest today, Josh Payne, has developed fascinating insights and systems to do just that. Josh sold his company, Stack Commerce, for nearly $100 million 4 years ago. 

A huge milestone - but as all exited founders know, the real story starts after the deal is done.Today, he’s building again - but with a completely different approach.

Josh isn’t optimizing for another massive exit. He’s after something bigger. So let’s see what we can learn from this fascinating man.

00:00:00 Introduction
00:00:45 Selling StackCommerce: Was It a Happy Moment?
00:02:00 The Emotional Impact of Selling a Company
00:03:30 Why Money Didn’t Solve Everything
00:05:15 Prioritizing Family After the Exit
00:06:30 Leaving the Company: A Tough Identity Shift
00:07:45 Taking a Healing Family Trip
00:09:00 Training for an Ironman & Overcoming Mental Barriers
00:12:30 Decoupling Identity from Business
00:14:00 Leadership & Purpose Beyond Business
00:16:00 Sacrifice vs. Suffering in Entrepreneurship
00:18:45 Ironman Training: Lessons in Overcoming Fear
00:22:00 The Challenge of Finding a New Purpose
00:23:45 Why Start Another Business After an Exit?
00:27:00 Learning to Build a Company Without Fear
00:30:00 The Difference Between First and Second Businesses
00:33:00 Finding a Sustainable Way to Build Again
00:35:00 Balancing Business & Personal Life After Exit
00:38:15 Why Many Second Businesses Fail
00:42:00 The Importance of Motivation in a New Startup
00:45:30 Avoiding the Trap of Losing Interest Midway
00:48:00 The Role of Peer Groups Like Tiger 21
00:50:30 How Long Does It Take to Truly Adjust After Exit?
00:53:00 Raising Kids With Wealth: Teaching Responsibility
00:54:00 Closing Thoughts & Future Plans