Exit Paradox

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.

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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. 

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00:00:00: Introduction and greetings
00:01:38: Roy's background and introduction to Magento 
00:02:3: The founding and growth of Magento 
00:03:36: Why Magento was sold to eBay 
00:05:28: Reflections on selling Magento 
00:05:53: Period after selling: Working at eBay 
00:06:51: Challenges and experiences at eBay 
00:10:18: Frustrations and limitations at eBay 
00:11:07: Difficulty in leading within eBay 
00:13:39: Reflections on regret and learning from the experience 
00:15:53: Pain of working at eBay 
00:18:04: Changes in the leadership team post-acquisition 
00:19:25: Leadership style and inspiration 
00:22:07: Transparency and leadership approach 
00:25:24: Personal reflections post-exit 
00:25:48: Reflecting on leaving Magento in 2013 
00:28:03: Deciding to leave eBay after Magento's Imagine conference in 2014 
00:29:15: The decision to travel with family for 14 months 
00:30:00: The travel route through Central America, South America, Asia, and Europe 
00:31:03: The travel experience and its impact on family dynamics 
00:36:04: Encouragement to other founders to take time off and travel 
00:43:02: Discovering new passions post-travel, specifically Iron Man and cycling 
00:45:59: Introduction to Personal Journey 
00:46:26: Discovering Passion for Sports 
00:46:10: Reinventing Post-eBay Life 
00:46:44: Starting the Fund During COVID 
00:48:04: Transition to Angel Investing 
00:51:27: Managing Wealth Post-Magento Sale 
00:54:03: Investment Philosophy and Public Equities 
00:56:45: The Non-Financial Rewards of Investing 
00:58:17: Search for Purpose Beyond Business 
01:01:27: Reflection on Purpose During Magento Years 
01:03:33: Balancing Life with Current Ventures 
01:06:12: Discussing a life of 24/7 dedication 
01:06:47: The search for purpose 
01:08:01: Meeting new people 
01:10:00: The intense journey with Magento 
01:12:56: Coping with the transition post-acquisition 
01:16:07: Being a creator versus an operator 
01:19:11: Future impact and legacy 
01:22:10: The desire for more meaningful work 
01:26:21: Closing remarks and goodbyes

Ten years ago, Brock Weatherup sold his first company, Pet360.com, to PetSmart for $160 million. 

It took under five years to build. Since then, he’s had two more successful exits, but two years ago, his journey took an unexpected turn when a life-changing medical diagnosis reshaped his entire outlook. 

In this episode, Brock talks about the secrets behind his consistent success, what keeps him optimistic and gives him a sense of purpose, and how he cultivates relationships in both business and private life.

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00:00:00: Introduction
00:01:17: Brock's first company exit experience
00:03:02: Transition challenges after the exit
00:03:31: Acquisition by PetSmart and transition experience
00:06:00: Acquisition of PetCoach
00:07:45: Brock's role and relationship with PetCoach team
00:08:59: Insights on being a startup to grown-up stage founder
00:09:41: Brock's involvement in subsequent businesses
00:11:00: Selling Great Pet Care due to MS diagnosis
00:11:56: Diagnosis impact on priorities and motivations
00:13:09: Adjusting to life with MS
00:14:38: Post-exit reflections and personal journey
00:15:41: Engaging with the business community in new ways
00:16:27: Realignment of life and business perspectives
00:21:47: Reflections on Sharing Knowledge and Purpose
00:22:08: Importance of Meaningful Involvement and Family Time in Purpose
00:22:26: Daily Approach to Living Purposefully
00:24:10: Impact of Diagnosis on Relationships and Support System
00:26:07: Friends' Support During a Difficult Time
00:26:54: Tracing the Evolution from First Business to Present
00:27:03: Story of the First Business Failure
00:30:02: Lessons Learned from Business Failures
00:31:15: The Role of Investors and Ethics
00:35:59: Challenges of Transitioning from Owner to Employee Mentality
00:38:24: Celebrating Failures and Learning from Them
00:40:52: Keeping Perspective in Business Ventures
00:41:14: Adapting and Learning in New Environments
00:42:48: Introduction to the CEO’s vision
00:44:09: Staying humble and continuing to learn 
00:51:22: Balancing experience and youthful energy 
00:52:06: The importance of continuous learning 
00:54:01: Past performance vs future success 
00:56:15: Building successful teams 
00:59:55: The value of the cap table and smart investment decisions 
01:02:22: Financial considerations and risk profiles 
01:03:27: Final advice for building a new business after an exit 
01:02:50: Being intentional in business and personal life 
01:03:11: Setting personal intentions and accountability 
01:04:25: Specific goals and realistic expectations 
01:06:00: Applying business discipline to personal life 
01:07:15: Correlation between personal and professional success 
01:08:08: Open communication and its importance 
01:09:19: Achieving balance and happiness 
01:09:22: How to be remembered

Three years ago, Scott Wolfe sold his company, Levelset, for half a billion dollars. 

Excited and relieved at first, he soon found himself deeply frustrated with the reality that his vision for the business would now never be realized. 

Scott is a natural creative who sees building a business as an artistic endeavor. 

It was this intrinsic need to create that sustained him through the grueling journey of building his business. Post-exit, he misses being driven by that vision and working alongside his exceptional, organically built team—one he feels can never be re-created. 

In this conversation, we explore the pros and cons of starting a sequel, the paradox of purpose, being a true “hedgehog,” the need for authenticity, full-time parenting, and raising entrepreneurial children.

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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.

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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.

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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 Transition

00:02:34 - 00:03:23 - The First Startup Experience

00:03:23 - 00:06:33 - Building True Connect

00:06:33 - 00:07:50 - Financial Discipline and Management Philosophy

00:07:50 - 00:12:42 - Transitioning from Finance to Entrepreneurship

00:12:42 - 00:15:08 - Balancing Multiple Ventures

00:15:08 - 00:19:05 - Considering Exiting True Connect

00:19:05 - 00:23:28 - Lessons in Hiring and Management

00:23:28 - 00:33:05 - Managing Investments and Personal Fulfilment

00:33:05 - 00:37:21 - Impact of Entrepreneurship on Family and Personal Life

00:37:21 - 00:41:06 - Raising Entrepreneurial Children

00:41:06 - 00:50:02 - Reflecting on Angel Investing

00:50:02 - 00:58:59 - Charity Work and Personal Fulfilment

00:58:59 - 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/

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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.

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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

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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