Ep. 24- Self-Funded Search, Deal Structures & Red Flags: Jacob Hall on Investing in Small Businesses

24/09/2025 34 min

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Episode Synopsis

In this interview, Sean Smith (Managing Partner of Search Fund Ventures & Founder of SMB Investor Network) sits down with Jacob Hall, Founder of Kando Capital, to explore the fundamentals of investing in small businesses through self-funded search and independent sponsor deals.Jacob shares his unique path from Fortune 500 operator to fund manager, his “buy box” criteria, and the red/yellow flags that investors should watch for when evaluating opportunities. The conversation dives deep into:Why operational experience matters more than Wall Street backgroundsHow to define and evolve your investment “buy box”Revenue quality, customer concentration, and key-person riskCreative deal structures: forgivable seller notes, earn-outs, rollover equityHR diligence, culture, and compensation as overlooked risksAligning sellers, buyers, and investors for long-term successThis is a must-watch for anyone interested in search funds, small business acquisitions, or creative capital structuring in the lower middle market.👉 Subscribe for more interviews with SMB investors and operators.👉 Leave your thoughts or experiences in the comments below.Connect with the speakers:🔗 Connect with Jacob Hall: https://www.linkedin.com/in/jacobhall01/🌐 Kando Capital: www.KandoCapital.com🔗 Connect with Sean Smith: https://www.linkedin.com/in/sean-smith-47ab2a70/🌐 SMB Investor Network: https://www.smbinvestornetwork.com/

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