Episode 390: Tax-Smart Exit Planning with David Flores Wilson

From Olympic sprinter to trusted advisor helping entrepreneurs save millions in taxes, David Flores Wilson shares proven strategies for QSBS planning, equity compensation design, and preparing business owners for successful exits both financially and personally. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with David Flores Wilson, CFA, CFP, Managing Partner at Sinceres, who advises entrepreneurs and business owners in New York City on personal financial planning from formation to exit and beyond. David is a multiple Investopedia Top 100 Financial Advisor whose guidance has appeared in CNBC, Yahoo Finance, the New York Times, US News and World Report, and Investment News. WHAT YOU'LL LEARN: In this episode, you'll discover how QSBS planning can potentially exclude $10 million to $70 million or more in capital gains from taxes when structured correctly, why LLC to C Corp conversion timing creates dramatic differences in tax outcomes, and how QSBS stacking through non-grantor trusts multiplies exclusions. David shares why equity compensation plans often fail to motivate the specific people they target and what questions to ask before choosing a vehicle. You'll also learn about the personal readiness component of exit planning that determines whether entrepreneurs thrive or struggle after selling their businesses. DAVID'S JOURNEY: David's path to financial planning started with entrepreneurial instincts in an unexpected place. Growing up in Guam, he ran a comic book arbitrage business as a kid, discovering price differences between local stores and mainland mail-order catalogs. His father was a CPA with a home office, and despite wanting nothing to do with accounting, David absorbed financial concepts through osmosis that would later prove invaluable. After college at UC Berkeley, David joined Lehman Brothers and worked through the financial crisis. During that time, colleagues started coming to him with financial planning questions, and he realized helping people with their money was his true passion. He sat on that realization for years before eventually transitioning to financial planning. When Covid hit in 2020, David and his partner Dan Ryan launched Sinceres, and the firm has been growing since. OLYMPICS LESSON: David represented Guam in track and field at the 1996 Atlanta Olympics, competing in the 200 and 400 meters. The experience taught him something crucial about career selection. Unlike running, where pushing harder brings diminishing returns and constant injury risk, financial planning offers the opportunity to improve incrementally every single day. That compounding knowledge approach now drives how he serves clients. KEY INSIGHTS: QSBS planning stands out as potentially the most powerful tax planning tool for qualifying entrepreneurs. C Corps meeting holding period and active business requirements can exclude $10 million in gains, or 10 times basis for older shares, with new legislation increasing that to $15 million. The planning becomes even more powerful with LLC conversions where market value at conversion becomes the QSBS basis. The biggest mistake with equity compensation involves choosing vehicles based on what owners like rather than what motivates specific employees. "Equity" can mean participation in profits, upside potential, a seat at the table, or financial disclosure. Different people value these differently, and the best planning starts with understanding objectives before selecting tools. Exit planning involves three components that David implements from the first meeting with business owners. Getting personally ready addresses what provides purpose after selling. Getting financially ready ensures the numbers work. Getting business ready covers everything from customer concentration to management team development. The recent One Big Beautiful Bill Act has changed QSBS holding periods, SALT deductions, and AMT rules. Business owners should review their planning with advisors rather than assuming previous strategies still apply. Perfect for entrepreneurs considering entity structure decisions, business owners thinking about exit planning, and anyone interested in tax-efficient wealth building strategies. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/davidfloreswilson FOR MORE ON DAVID FLORES WILSON: https://www.planningtowealth.com https://www.linkedin.com/in/davidfloreswilson/ FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share ...