Hardest thing about buying your first SMB? Deciding which biz in your pipeline is “good enough.” There are a million criteria checklists (e.g., HBS Guide) and rules of thumb. But nothing beats experience (and quality advisors/mentors) to help you make the really hard decisions…
Maybe it’s a pesky customer concentration issue, a biz with CapEx needs when you wanted something asset light, a price that’s a half turn too expensive, or a seller that wants to roll a little equity when you want to own 100%. When do you bend your own rules to get a deal done?
There is no perfect biz with a perfect price. Searching for perfection is part of what causes Search to take 2 yrs on avg– I made that mistake. It takes time & reps to know when to bend your rules, get a deal done and get into the driver’s seat (which is where the magic happens).
In SMBs, the operator can absolutely move the needle and make an imperfect deal worth doing. Just be clear and honest about the problems you can fix, the problems you can live with, and the problems you can’t (especially if you are going to be the operator).

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More from @Sam_Rosati

21 Aug 20
Working on buying SMB w/ $1.5M EBITDA. As I work through financing, it’s pretty clear that the $1.5-2M of EBITDA range (give or take) is a sweet spot for SMB buyers b/c it’s an “in between” size for usual buyers. Too big for “job buyers” and too small for other folks (PE, SBIC).
For “job buyers” … after adding $250k deal expenses (SBA fee, lawyer, QofE, etc) and a $250k working capital cushion, the project cost is $6.5M. Subtract $650k seller note and $5M max SBA loan and the deal requires an $850k cash injection.
$850k is doable for some buyers, esp self-funded searchers w/ investors ready to write checks, but certainly not easy for “leave corporate world, buy a job” folks. Plus, SBA is super tight post COVID w/ max size loans ($5M) that have big airballs -> bigger cash injections needed.
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