Exit Paradox

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.
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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.

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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 

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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/

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(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

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(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/

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(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.

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(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

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(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.

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(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