Interview Recap - Self-Funded Search, Deal Structures & Red Flags

I recently had the chance to sit down with Sean Smith, founder of the SMB Investor Network and Managing Partner at Search Fund Ventures, to talk about what’s really going on in the world of small business investing. If you’re curious about how Kando Capital came to be—and where we’re focused—this is a good place to start.

In our conversation, I share my personal transition from being an operator inside Fortune 500 companies to launching an investment platform for self-funded searchers and independent sponsors. We unpack what it means to invest well in the lower middle market—and what I look for when backing operators at the earliest stages of their journey.

We dig into some of the things I’ve learned the hard way:

• Why operational reps matter more than a Wall Street resume

• How to define (and evolve) your “buy box” without becoming a bottleneck

• The subtle signs of risk: customer concentration, key-person dependence, and culture mismatch

• How to creatively structure deals—especially when aligning seller, buyer, and investor incentives

• And why I believe HR, comp, and post-close integration deserve as much diligence as the P&L

It’s a candid look at how I think about backing small business operators—and why I believe this asset class, in the hands of the right people, is both resilient and radically undercapitalized.

If you’re an investor, a searcher, or just exploring ETA, I hope you’ll give it a listen.