Exit Paradox

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, an entrepreneur exploring the art of business, joins Anastasia Koroleva, who navigates identity amidst success. They discuss the obsessive drive that fuels entrepreneurship and the emotional turbulence post-exit. The duo shares insights on maintaining personal identity while achieving professional goals and the joys of creation as the true reward. They address the transformative power of relationships and the importance of self-awareness in the entrepreneurial journey, urging listeners to view their ventures through a lens of creativity and purpose.

Bill Hudenko, a serial exited founder and clinical psychologist, discusses the correlation between happiness and money, worries and concerns, joy in life, self-definition, future plans, sense of purpose, personal legacy, motivation for impact, and importance of positive impact. He also reflects on childhood, entrepreneurship, mental health, spirituality, life purpose, and building relationships.

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

Timo Armoo, a young entrepreneur who impressively sold his first business at 17 and achieved an 8-figure exit by 27, shares his insights on what comes next after such success. He reflects on the emotional challenges of post-exit life and the importance of cultivating meaningful connections. Timo discusses the shift from seeking validation through financial achievements to focusing on purpose and impact. He emphasizes developing an abundance mindset and the significance of true motivation in entrepreneurship, ultimately redefining success beyond money.

After selling his first business 15 years ago, David Goldberg became obsessed with the idea of making it absurdly easy for entrepreneurs to have an outsized social impact. This led to the creation of Founders Pledge, a community of experienced entrepreneurs who have now collectively pledged over $10 billion to charities. In this episode, he guides us on how to think about our post-exit impact in a rational and authentic way. 👤 LinkedIn: https://www.linkedin.com/in/davidjonathangoldberg?utm_source=share&utm_campaign=share_via&utm_content=profile&utm_medium=ios_app 🖥️ Founders Pledge: https://www.founderspledge.com/ _____________________________________________________ Timestamps: 00:01:08: The Purpose of Life and Time 00:03:29: Drive and Work Ethic 00:03:42: David's thoughts on Identity 00:05:16: Secrets to a Successful Romantic Relationship 00:06:00: What keeps David up at night 00:07:56: Waking up Motivation 00:08:30: How David wants to be Remembered 00:08:44: Parent's Expectations 00:10:02: Value of Formal Education and Start of Career 00:13:36: David's First Business 00:17:15: Developing Communication Skills 00:18:20: The moment of Business Exit 00:19:44: Motivation for the First Business 00:20:10: Changes after Business Selling 00:20:40: Upbringing and "winning the life lottery" 00:21:31: Decision to do more than amass wealth 00:22:28: Challenges and obstacles in philanthropy efforts 00:24:07: Journey to discover true purpose 00:24:38: Process and experience of self-growth 00:26:26: Learning to think critically through formal education 00:30:03: Undergoing the cultural shift of studying abroad 00:32:05: Founders Forum group and understanding real poverty 00:33:22: Redefining success after selling first business 00:35:57: Encountering true poverty in Southeast Asia 00:37:09: Using resources effectively for maximum impact 00:37:49: The problem of "poverty tourism" 00:39:09: How compassion plays a role in business success 00:40:31: Introduction to Founders Forum and efforts to help social entrepreneurs 00:41:04: Reasons why the initial idea didn't work. 00:42:08: Evaluating the potential of startups 00:42:27: The challenge of execution in social businesses 00:43:06: Pivoting to support commercial entrepreneurs 00:45:10: Founders Pledge 00:47:23: The relationship with Founders Forum 00:50:31: Aim to give effectively in Founders Pledge 00:52:06: Resolving the problem of global donations 00:55:02: Funding model of Founders Pledge 00:56:56: The reality of Donor Advised Funds 01:00:06: The challenge of raising funds annually 01:02:20: Focus on impact in Founders Pledge 01:03:33: Present commitments and funds injected in Founders Pledge. 01:04:29: Scaling up 01:05:32: Mental health as a neglected area 01:06:17: Introduction of non-profit working on mental health treatment in Africa 01:07:35: Effects on post-exit journey of founders who pledged 01:08:02: Role of philanthropy after exit 01:11:36: Introduction to Founders Pledge 01:15:02: The spiritual journey through Founders Pledge 01:15:43: Introduction to Pledge Ventures 01:18:02: Rules and initial fundraising for Pledge Ventures 01:20:53: Commencement of investment through Pledge Ventures 01:25:05: Introduction to the Foundry program 01:25:54: Bespoke research programs for larger sums of yearly philanthropy. 01:26:03: The Order of Giving and the Importance of Knowledge 01:26:41: The Foundry Program 01:27:26: Partners, not Clients 01:28:07: Improving The Efficiency of Giving 01:29:19: Transparency in Philanthropy 01:30:00: Aligned Incentives with Members and Issues with Charities 01:31:03: The Importance of Community in Philanthropy 01:32:04: Future Impact and Growth of the Organization 01:32:46: Efficiency and Control in Giving 01:33:18: Pledges and Donations: Freedom of Choice 01:34:03: The Organization’s Differentiating Factors 01:35:11: Final Words

Richard Steel, a former business owner who led a public company and advised the White House, shares insights from his transformative journey post-business sale. He discusses the emotional aftermath of exiting Steel Media, including celebrations with employees and IPO experiences. Steel emphasizes creating a 'portfolio of interests' and reflects on his evolution from ad executive to entrepreneur. He also touches on lifelong learning, the importance of family, and his commitment to community and personal growth in an ever-changing landscape.

Michael Sonnenfeldt, founder of TIGER 21 and serial entrepreneur, shares profound insights on life after a liquidity event. He discusses the critical need for introspection post-exit and how such experiences teach humility. The conversation dives into the ‘2% rule’ for spending, the contrast between angel investing and capital preservation, and strategies for finding new purpose after a business sale. Sonnenfeldt emphasizes the importance of patience, gratitude, and giving back, and reveals how creativity can drive financial success.

If you enjoyed this podcast, I recommend you check out my first conversation with Michael Sonnenfeldt, which you can find here My guest today is Adrien Cohen, a remarkable entrepreneur. He built and sold his first business, Lazada, for $3 billion and led the rapid growth of Tractable, a multi-billion-dollar AI company for accident and disaster recovery. In our conversation, Adrien candidly shares his journey to finding his life's purpose, why he quit a lucrative job at Goldman Sachs and prefers venture philanthropy over impact investing, his tips for a happy marriage, and the intriguing story of his parents keeping their wealth a secret until he made his own mark Adrien lived in France, China, Vietnam and the UK. Follow Adrien Cohen on: linkedin.com/in/adrien-cohen-883a1527/

Entrepreneur Mimi Ikonn discusses finding purpose after selling Luxy Hair, focusing on gratitude, self-improvement, and conscious uncoupling. She shares insights on legacy, redefining success, and choosing love as the ultimate purpose.