Exit Paradox

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

What would you do if you sold your company for 300 million dollars? Retire? Explore the world? Do all these other things you had no time to do while building a business?

This is not what my friend Alex Macdonald did when he sold his company Velocity Black two years ago. In fact, Alex made it quite impossible for himself to have any kind of post-exit sabbatical. Why?

Well, Alex has seen enough of his post-exit founder friends getting stuck in full-blown existential crisis after they sold their company. He didn't want that to happen to him. 

In this episode, we're going to explore why he made this decision, whether two years later he still feels it was the right one, and how he applies the lessons from his first full entrepreneurial cycle to building his new business, appropriately called SQL.

00:00:00 - Introduction

00:02:25 - The Story of Velocity Black

00:07:46 - Selling Velocity Black to Capital One

00:07:05 - Why Alex Started Another Business Before Selling His First One

00:10:52 - The Founder’s Existential Crisis After an Exit

00:12:45 - The Shortage of Builders, Not Investors

00:14:19 - Work-Life Balance & Health After an Exit

00:16:21 - Lessons from Running a 24/7 Business

00:19:52 - Changing Approach to Work with Sequel

00:21:19 - Different Approaches to Post-Exit Businesses

00:24:19 - Sequel: Building a Next-Gen Goldman Sachs

00:27:26 - Managing Motivation After Financial Success

00:31:03 - Fulfillment vs. Happiness: What Really Matters?
00:33:15 - The Biohacking & Longevity Obsession

00:35:51 - Community & Meaning in Life After an Exit

00:39:13 - The Idea of Creating a New Religion

00:45:46 - The Role of Structure & Responsibility in Life.

00:54:08 - The Challenge of Freedom After an Exit

00:57:46 - Angel Investing & How It Led to Sequel

01:03:42 - Helping Athletes Transition Beyond Their Careers

01:07:37 - Building a Legacy vs. Just Making Money

01:10:52 - Avoiding Mistakes in Early-Stage Investing

01:15:30 - The Power of Influence in Investing

01:20:05 - Sequel’s Future Plans & Scaling the Model

01:25:00 - What Drives Long-Term Success?

01:30:10 - Final Thoughts & Advice for Founders

My guest today is Cory Janssen, co-founder of Investopedia. 

Cory sold the business 17 years ago, but what came next was far from the smooth ride he or anyone might have expected. He spent years in painful trial and error, half-heartedly starting new ventures while avoiding real work, experimenting with professional investing and retirement. None of it satisfied his deeper need for the sense of purpose he felt while building Investopedia. 

Everything changed when Cory went back to building and working. But this time it felt different. 

His focus shifted toward unselfish, larger impact goals. His new non-monetary motivation gave him powerful drive and a clear sense of direction and alignment. 

Today, Cory finally feels deeply fulfilled, energised and joyful. 

There is so much to learn from Cory's story and we are so lucky he agreed to share it openly. It's rare, raw and packed with specific practical insights for anyone navigating the complexities of post-exit life.
 _____________________________________________________ 
00:00:00 Introduction
00:01:40 Guest Introduction: Cory Janssen’s Story
00:04:00 Founding Investopedia: The Early Days
00:10:55 Deciding to Sell Investopedia
00:22:15 Regret After Selling: Financial and Emotional Impact
00:35:10 Working for the Acquirer: Lessons Learned
00:46:50 Negotiating the Sale Process: Tips for Founders
00:56:20 Post-Exit Struggles: Managing Wealth and Purpose
01:07:10 Challenges of Professional Investing
01:15:30 Rediscovering Passion for Building: Transitioning to AI
01:26:15 Balancing Parenthood and Entrepreneurship
01:37:30 Raising Kids with Wealth: Avoiding Entitlement
01:40:00 Closing Reflections and Key Takeaways

This interview is a special one for me. 

Michael Miller has been a friend for over 15 years and has made a huge difference in my life. 

He's a Vedic meditation teacher who taught me to meditate at a time when I was searching for clarity and tranquility following a life-changing exit. Since then, meditation has been my go-to tool for healing, finding peace, processing ideas, and making decisions. 

And it's not just me, people like Jack Dorsey, Bill Gates, Arianna Huffington, and Ray Dalio all credit meditation for helping them on their own post-exit journeys. 

Before discovering his calling as a meditation teacher, Michael had a successful business career. That experience gives him a unique ability to explain meditation in ways that make sense to us entrepreneurs. 

If you've tried meditation before, but let it slip, this might just inspire you to pick it back up.

 _____________________________________________________ 
00:00 The Healing Power of Meditation
02:46 Personal Journeys and Transformations
06:10 The Science Behind Meditation
11:54 Meditation as a Decision-Making Tool
17:49 The Ripple Effect of Meditation
24:06 Creating Peace from Within
40:07 The Ripple Effect of Inner Peace
44:51 The Journey of Personal Growth Post-Success
49:52 Addiction as a Spiritual Search
52:15 From Material Success to Fulfillment
59:33 Designing a Toolbox for Holistic Leadership
01:13:30 The Journey of Self-Discovery
01:18:05 Navigating Life Stages and Transitions
01:23:25 Embracing Discomfort for Growth
01:29:35 The Role of Community and Giving Back
01:34:08 Traveling with Purpose
01:39:23 Understanding Consciousness
01:42:34 Defining Purpose and Connection

My dear friend Sarah Douglass sold her incredibly successful e-commerce business three years ago, achieving the financial freedom she had always dreamed of. But soon after, she found herself grappling with a new challenge: balancing her newfound success with an ever-deepening desire for contentment and a powerful drive to create impact. In today’s conversation, Sarah shares her journey with disarming authenticity, opening up about her deepest struggles. We explore the unexpected void left by success, the difficulty of resisting the urge to immediately start something new just to feel productive, and her shift from chasing external milestones to embracing intentional living—rediscovering who she is as a whole being, not just as an entrepreneur.

_____________________________________________________ 
00:00:00: Introduction and greetings
00:01:04: Sarah's business journey beginnings (Music school)
00:01:39: Transition to selling online (Discovery at dinner)
00:02:04: Starting with camping gear (Wise Owl Outfitters)
00:02:56: Challenges and operations (Traveling to China)
00:03:40: Balancing family and business (Moving and kids)
00:04:23: Working with her husband
00:05:21: Husband's role and career shift (Becoming a painter)
00:04:37: Decision to sell the business
00:05:00: Influences and reasons for selling
00:07:01: Financial freedom and exiting strategy
00:08:16: The selling process (Timeline and logistics) 
00:09:56: Reflections on the buyer's bankruptcy 
00:11:06: Emotional impact of selling 
00:12:10: Post-sale challenges and burnout 
00:13:23: Realizations and health impact 
00:14:40: Personal and existential reflections 
00:16:55: Seeking and understanding contentment 
00:18:37: Advice on spirituality and life direction 
00:19:06: Initial thoughts on spirituality and personal development 
00:19:23: Exploring different avenues for growth 
00:19:46: Impact of personal coaching and physical health 
00:20:36: Reflection on life's purpose post-exit 
00:21:32: Evaluating new opportunities and the allure of starting new businesses 
00:25:00: Importance of being helpful to others 
00:27:18: Finding balance in life and prioritizing oneself 
00:27:50: Balancing motherhood and business 
00:32:17: Handling wealth and teaching children about money 
00:34:42: Shifts in business motivation without the need for money 
00:38:17: Importance of having a supportive team 
00:39:08: Pursuing new, exciting projects 
00:40:02: Balancing current business with new ventures 
00:40:26: Benefits of taking extended trips 
00:42:04: Discovering oneself through new experiences 
00:46:04: Reflections on legacy and impact on others 
00:48:02: Interpretation of "Stay hungry, stay foolish" 
00:51:03: Struggles of balancing business and family as a woman 
00:56:06: Comparison of post-exit life to athletes' career transitions 
00:56:38: Feeling lonely during the process 
00:56:52: Searching for information online 
00:57:15: Conclusion and thank you

Tim Schumacher is the exited founder and former CEO of Sedo, one of the world's largest domain marketplaces, which he led for over a decade before stepping down 13 years ago. What sets Tim apart is how he mastered the elusive work -life balance while still building his company, something most entrepreneurs only dream of. This balance helped him avoid the emotional rollercoaster that so many of us face after a successful exit. In this episode, Tim shares his thoughts on keeping life supernormal, the bootstrapper mindset, being a scaler versus a zero-to-one founder, and finding new purpose in tackling climate change.

_____________________________________________________
00:00:00 - 00:00:39 Introduction
00:00:39 - 00:02:58 Tim Schumacher's Exit and Reflections
00:02:58 - 00:05:58 Transition to New Ventures
00:05:58 - 00:07:28 The Importance of Rest and Work-Life Balance
00:07:28 - 00:09:51. Personal Interests and Climate Change
00:09:51 - 00:11:55. Evolution of Motivation and Values
00:11:55 - 00:16:38. The Bootstrap Mindset
00:16:38 - 00:18:28. Balancing VC and Bootstrap Approaches
00:18:28 - 00:25:30. Scaling vs. Building from Scratch
00:25:30 - 00:29:37. Financial and Purposeful Integration
00:29:37 - 00:31:12 Managing Identity Change Post-Exit
00:31:12 - 00:37:05 Work-life Balance and European Influence
00:37:05 - 00:36:59. Entrepreneurial Legacy and Family
00:36:59 - 00:42:20. Reflecting on Business Strategies and Learnings
00:42:20 - 00:45:26 Revisiting Entrepreneurial Failures
00:45:26 - 00:47:09. Cultural Exposure and Entrepreneurial Growth
00:47:09 - 00:49:29 Purpose and Motivation Beyond Business