Navigating Wealth

Nitun Verma, a Stanford-trained sleep physician who built sleep programs for Apple and Meta, talks about why high-performers underperform from hidden habits. He covers wearables and their limits, how caffeine and alcohol quietly wreck sleep, the real meaning of sleep quality beyond hours, evening routines as the biggest lever, and practical ways to find your true sleep need.

Dave Nemetz, co-founder of Bleacher Report who scaled the site from a hobby to a $200M sale and later founded Inverse, shares his story. He covers rapid growth and the sale to Turner. He talks fundraising choices, a risky content pivot that nearly failed, designing life after an exit, and practical ways founders escape the VC treadmill.

Joey McGuire, Texas Tech head football coach who led the Red Raiders to their first Big 12 title, talks about college athletics' modern chaos with structure. He covers NIL revenue sharing, the transfer portal’s analytics-driven 82% hit rate, preparing 19-year-olds for taxes and investments, and how programs act as wealth-management incubators for players.

Michael Saperstein, former in-house counsel at MLB, Marvel, and Disney, brings insider stories from the rise of MLB Advanced Media to Marvel’s licensing engine. He discusses how the iPad reshaped digital comics, why centralized streaming rights changed valuations, and the looming threat of generative AI to traditional IP licensing. Short, sharp takes on legal strategy, career resilience, and the future of creative ownership.

Tom O'Toole, former CMO of Hyatt and United who led MileagePlus, explains why airline loyalty is a multi-billion dollar business. He unpacks how miles are sold, engineered award availability, and the shift to dynamic pricing. He also shares a roadmap for designing a deliberate post-C-suite portfolio life with boards, advising, and teaching.

Andy Louis-Charles, franchise investor and former Chief Strategy Officer at Custom Ink, champions franchising as a route to scalable ownership. He shares his Inter-Opus philosophy about finding fulfillment in the work, why he pivoted from angel investing to underwriting execution risk, and how to turn strong single-unit concepts into franchisable systems.

Chris Hutchins, host of All The Hacks and serial entrepreneur who helped build companies acquired by Google and Wealthfront. He covers two-card credit strategies and when to apply the 80/20 rule for optimization. He explains using AI to speed personalized research, travel points tactics and award timing, and how to involve kids in money and travel decisions.

Diamond Innabi, Principal at Software Equity Group with ~15 years advising SaaS founders on M&A and exit strategy. She breaks down the 4–6 month sell process and why founders hire investment bankers. Topics include buyer types and valuations, earnouts and rollover equity, AI’s impact on deals and diligence, and practical pre-sale fixes founders should make.

Ilka Gregory, President and CEO of a seventh-generation single family office (founded 1866) with two decades at top firms. She unpacks what a family office is and when to start one. Short takes on managing wealth across generations, involving spouses and stepchildren in governance, preparing heirs without smothering them, tax-driven domicile moves, and how offices source and steward investments.

In this engaging conversation, Eric Wiklendt, Managing Director at Spayside Equity, dives deep into the complexities of selling businesses. He outlines the three main exit strategies for founders and emphasizes the importance of operational improvements in private equity. Eric contrasts private equity with corporate M&A and explains when strategic buyers might offer more value. With insights on the current manufacturing landscape, he discusses the impacts of AI and reshoring, all while highlighting the need for creative talent in an evolving economy.