Moneywise

Many founders reach major milestones yet still feel unfulfilled. The episode explores why traditional definitions of success can lead to dissatisfaction. It delves into the emptiness that follows big achievements. Founders often chase external validation but struggle with internal fulfillment. The conversation emphasizes aligning goals with personal values to foster true satisfaction. By shifting focus from external markers to internal success, founders can enhance both their well-being and external outcomes.

Kevin Bartchlett, founder of a compostable toilet company that sold for $9M but left him with nothing due to a handshake agreement, shares his hard-earned lessons. He reveals the moment he realized his payout had vanished and the costly risks he took on trust alone. Despite the setbacks, Kevin remains optimistic and discusses his exciting new venture: a flying car prototype. His journey emphasizes the importance of getting everything in writing and going all in when you bet on yourself.

Adam White, founder and CEO of Front Office Sports, recounts how he turned a college project into a $20M media brand with NFL partnerships. He shares the pivotal tweet that led to a $750K investment and discusses the significance of brand aura in the media landscape. Adam reveals why he willingly gave away 51% ownership. Learn how he grew a newsletter audience to 800K without focusing on SEO, diversified revenue streams, and his personal journey, including paying off student debt and redefining success as freedom.

Discover the hidden truths of what happens after selling a company. Learn why deal structure often trumps sale price and how earnouts can be a trap. Many founders feel poorer after big payouts due to financial insecurity. Surprisingly, 92% of entrepreneurs return to work instead of retiring. Post-exit identity crises are common, and big purchases often lead to swift regrets. Timing the market usually backfires; satisfaction comes from selling when ready. Lastly, losing control of company culture is a significant frustration for many.

Alex Smereczniak, a dynamic entrepreneur who built a $100M laundry business and is now the mastermind behind Franzy, shares his journey from a college dorm to franchise success. He discusses the personal crises that led him to step down as CEO, the shocking commissions of up to 60% that franchise brokers take, and his mission to democratize franchise ownership. Alex advocates for a transparent, flat-fee model in franchising and believes it can provide opportunities for those displaced by AI, redefining success through impact rather than simply financial gain.

Guy Allen, a dynamic sushi entrepreneur and former real estate tech professional, reveals how he transformed a 12-seat sushi bar into a $3M success. Discover how his sushi photography hobby blossomed into a six-figure uni import business and why he prioritizes high-quality casual dining. He uncovers the vital elements for restaurant success—food, location, and branding—and shares insights on scaling to 40 locations. With transparent financials and innovative strategies, Guy offers a fresh perspective on the restaurant industry's complexities.

Kory Mitchell, a blue-collar entrepreneur who scaled an asbestos abatement business to a $200M sale, shares his rollercoaster journey in business. He discusses the pitfalls of hiring a CEO who mismatched projects with company strengths, leading to steep losses. Kory also reflects on the true cost of company culture and communication during rapid growth. After burnout post-exit, he emphasizes the importance of mentorship and finding off-market deals, alongside valuable lessons on trust and the human element in M&A.

Mike and Kass Lazerow, successful entrepreneurs who co-founded Buddy Media and Golf.com, share their journey of building a $745M company while navigating family life. They dive into the chaos of selling their business, surviving a bankruptcy scare, and how Tiger Woods played a pivotal role. The couple discusses the importance of trust and communication in their partnership, revealing their approach to managing work disagreements and finances. They redefine what 'enough' money means, highlighting experiences over accumulation, and share candid lessons from their entrepreneurial journey.

Jacqueline Johnson, a founder and serial entrepreneur, discusses her $22M exit from Create & Cultivate and her journey back after buying the company back. She shares her experience with burnout and divorce, which led her to take a year off for self-discovery. Jacqueline reveals how she turned $10K into $1.2M through angel investing while enjoying a lavish lifestyle. She talks about the scrutiny female founders face, the difference between wealth and status, and how she finally felt successful. Her insights on building community and future-focused wealth strategies are particularly inspiring.

In this engaging discussion, Jordan Schlipf, a serial founder and CEO of a beauty business, shares his entrepreneurial journey and the lessons learned from choosing fun over profit. He reveals the allure that brought him back from investment banking to startups and the challenges of the Rainmaking model, which prioritizes passion but can lead to costly mistakes. Jordan reflects on his current role, the realities of life in London as a founder, and his evolving definition of wealth, emphasizing support and time over purely financial gains.