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

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The SMB Investor

Nick Bryant

25 episodes

4 days ago

Forget startups. Forget climbing the corporate ladder. The real path to wealth? Owning profitable small businesses. Hosted by Sean Smith and Nick Bryant, The SMB Investor dives into how investors, operators, and dealmakers are building wealth through small business acquisitions, syndicates, and holding companies. We talk to the pros—fund managers, investors, searchers, and service providers—who are making SMB investing the next big asset class. Whether you want to invest, operate, or build your own holding company, this podcast is your playbook.

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Business

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Investing

Business

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

The SMB Investor

34 minutes 18 seconds

1 month ago

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

🔗 Connect with Sean Smith: https://www.linkedin.com/in/sean-smith-47ab2a70/

🌐 SMB Investor Network: https://www.smbinvestornetwork.com/