Moneywise

Vinay Hiremath, co-founder of Loom and now worth nearly $50 million, shares his transformative journey from startup success to personal exploration. He discusses his surprising choice to leave millions on the table and the emotional aftermath of his company’s sale. Vinay reflects on paying off his parents' mortgage and the meaning of wealth beyond money. Now exploring physics and robotics, he reveals the paradox of financial freedom and the search for identity amidst newfound wealth, provoking thought on what it truly means to be free.

Chris Cooke, a former skeptic of capitalism turned millionaire, shares his unique journey post-sale of his company for $30 million. He talks about how he spent most of it within six months on a weed farm, beach house, and comedy club in Thailand, all while embracing his Buddhist principles. Chris candidly discusses the conflicts between his values and financial success, the challenges of managing relationships after sudden wealth, and how he’s now focused on building a sustainable business rather than just chasing growth.

Dan Berger, who sold his company Social Tables for $100 million, shares the surprising truth about his unchanged net worth since then. He dives into his biggest financial blunders, like angel investing and a lavish NYC apartment. Berger reflects on the deeper issues founders face after a big exit, including the quest for belonging and personal identity. He discusses living by the 'Die With Zero' philosophy and how early life challenges shaped his journey. Through his insights, he emphasizes the importance of relationships and community for true fulfillment.

Tommy Mello, billionaire entrepreneur and CEO of the billion-dollar A1 Garage Doors, shares insights from his remarkable journey. He reveals how he transformed a small business into a massive empire by mastering strategic investing and emphasizing relentless competition. Mello discusses the key sacrifices needed for success, his philosophy on building businesses with an exit in mind, and his passion for creating millionaires among his employees. His wealth-building strategies and commitment to mentorship provide a roadmap for aspiring entrepreneurs.

Rob Hoffman, an entrepreneur and member of the Hampton community, made a life-changing move to Colombia, leveraging geo-arbitrage to triple his wealth. He discusses the financial perks of living abroad and how a frugal lifestyle can lead to significant savings and reinvestment opportunities. Rob emphasizes the importance of community involvement and the ethical responsibilities of expatriates. His journey from an anti-capitalist hippie to a successful business owner reveals a transformative approach to wealth and personal freedom.

Rob Walling, a serial entrepreneur and comic book aficionado, discusses his unique investment strategy. He reveals that over 10% of his net worth is tied up in collectibles, blending passion with financial savvy. Rob highlights the emotional fulfillment of comic collecting, linking it to childhood dreams and financial freedom. He warns of the hidden risks involved and differentiates between investing and gambling. With insights on auction strategies and managing valuable items, Rob showcases how personal interests can spice up investment portfolios.

Brothers Chris and David Sinkinson, who co-founded and sold AppArmor for $40 million, share their entrepreneurial journey and the unique bond that kept them grounded. They discuss the isolation many founders face post-exit and how their brotherhood shielded them from reckless decisions. The duo reflects on navigating the identity crisis after the sale and the importance of trust and humor in their partnership. Excited for future ventures, they emphasize valuing relationships over financial gains in their next steps.

Chris Bakke, founder of multiple companies including Lasky, reflects on his remarkable journey from tech mogul to devoted dad. After selling to Elon Musk, he discovered that true success isn't measured in millions but in family time. Bakke discusses leaving behind the relentless hustle in favor of personal fulfillment and smaller ventures. He shares insights on balancing financial ambitions with parenting duties and the trade-offs of working with Musk. His transformation highlights a new, richer perspective on happiness and ambition.

Peter Wokwicz, a serial entrepreneur who built a $500 million fortune through relentless curiosity, discusses how passion drives his success rather than profit. He reveals his philosophy on embracing risk and ‘failing fast’ to thrive in the fast-paced business landscape. Peter shares how curiosity allows him to innovate and avoid burnout, transforming his wealth into a playground for exploration. He believes pursuing joy over financial gain leads to a more fulfilling life, highlighting the importance of maintaining a childlike sense of wonder.

Is checking your portfolio daily ruining your peace? The podcast dives into the contrasting strategies of three ultra-wealthy entrepreneurs. Chuck avoids daily checks, focusing on mental well-being after a $2.5 billion exit. Travis shifted his attention to building new businesses, while Anne thrives on daily oversight, leveraging her research for impressive growth. The discussion highlights the emotional toll of tracking investments and encourages matching your investment strategy to your personality for better financial health.