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

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 backgrounds - How to define and evolve your investment “buy box” - Revenue quality, customer concentration, and key-person risk - Creative deal structures: forgivable seller notes, earn-outs, rollover equity - HR diligence, culture, and compensation as overlooked risks - Aligning sellers, buyers, and investors for long-term success This 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**](https://www.kandocapital.com/) 🔗 Connect with Sean Smith: https://www.linkedin.com/in/sean-smith-47ab2a70/ 🌐 SMB Investor Network: https://www.smbinvestornetwork.com/ #SmallBusinessInvesting #SearchFunds #IndependentSponsors #DealStructures #CapitalAllocation #RevenueQuality #EntrepreneurshipThroughAcquisition #PrivateEquity #Investors #SMBEcosystem