Moneywise

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.

Donald Spann, a self-made entrepreneur who built a multi-million dollar call center from scratch, shares his journey from dropping out of college to achieving a remarkable $12M exit. He reveals how he launched a cleaning business inspired by a Reddit comment and gained 65,000 applications on a viral mom blog. Donald discusses the significance of never raising outside capital, living in Mexico on $10K a month, and the unique challenges he faced as a Black entrepreneur in affluent spaces. Now, he's focused on new ventures in cannabis and life sciences.

Rajiv Khaneja is a young entrepreneur and co-founder of Arvita Therapeutics, an innovative biotech company focused on mRNA cancer vaccines. He reflects on building AdButler into an 8-figure business while deliberately avoiding lifestyle inflation. Rajiv shares insights on his frugal choices, such as driving a Prius and living in the same city, showcasing a mindset rooted in his immigrant upbringing. He values attentional freedom over luxury, believes in community support for growth, and now channels his wealth into impactful ventures like cancer research.

Ali Abdaal, a successful YouTuber and entrepreneur, shares his unique journey from medicine to personal branding. He dives into how financial freedom has enhanced his happiness, rather than defined it. Ali recounts a scamming incident that sparked a lucrative business, his reflections on wealth versus well-being, and why a $2M profit goal feels more satisfying than chasing greater sums. He emphasizes the importance of creating personal luxuries and the freedom that comes from redefining success on his own terms.