302 Deals In, Here Are the Red Flags We See Most Often
After seeing 302 business acquisition deals over the last 14 months, there's an area of due diligence we don't think gets nearly enough attention: how the searcher actually makes decisions.
As minority investors, we don't have operational control. We win when the searcher wins - which means everything depends on their judgment. So we watch closely.
The green flags are what you'd expect from someone who will thrive as an operator:
1. They build their models and fundraising decks with genuine human thought rather than outsourcing their thinking to AI.
2. They share their reasoning in detail - not just what they've decided, but why, often in writing.
3. They demonstrate mastery of the details and the logical connections between them. A searcher who notices that Days Sales Outstanding is rising sharply during diligence and immediately knows to adjust the working capital peg from trailing 12 months to trailing 3 is telling us something important about how they think.
The red flags are subtler but just as telling:
1. Making a decision first and then constructing supporting logic - not the other way around.
2. Focusing on what's possible while underweighting what's probable, especially with foreseeable risks.
3. Choosing options that create short-term benefits at the cost of long-term problems - a habit that compounds in the wrong direction once someone is running a business.
We're not just underwriting the deal. We're underwriting the person making decisions about it every day for the next decade.
Plus:
- Great insights from a successful searcher, Tamar Schreiber-Daniel, on one of the toughest parts of a business acquisition: re-earning the trust of customers loyal to the brand.
- Sam Rosati's SMBootcamp - the tactical in-person training that has helped 400+ searchers close 70+ acquisitions - is leaving Tampa for the first time and coming to Denver, with PROX Search Capital's Adam Markley co-hosting. If you're in the Mountain West and want the same practical, no-fluff curriculum searchers have been flying to Florida for, this is worth a look. Register here.
- SBA Administrator Kelly Loeffler is calling for the 7(a) and 504 loan caps to be raised from $5 million to $10 million - and if it happens, it would solve a real problem we see in the market today: businesses with $2 million to $3 million in earnings that fall into a "donut hole" where SBA debt is too small and non-SBA debt isn't readily available. Changes require an act of Congress, but Loeffler believes it could happen as part of a Defense Authorization bill. Full article here.redacted