The Biggest Red Flag I Look For in a Deal? It’s Not in the Docs.

I’ve reviewed thousands of pages of contracts over the years. I’ve run diligence across jurisdictions, industries, and deal types. But my #1 recommendation when evaluating a deal has nothing to do with legal structure.

Spend time with the founders.

Talk to them. Ask questions. Not just about the product or the numbers — but how they think, how they handle pressure, how they treat hard questions.

And then pay attention to one thing above all: Do they want you to understand their business — or do they just want you to write the check?

If a founder is cagey during diligence — even after you’ve signed an NDA and clearly signaled interest — that’s a problem. Transparency in diligence isn’t a favor. It’s a signal. If they’re not forthcoming now, when they need something from you, it only gets worse post-close.

I’ve seen more deals turn sideways because of lack of trust and communication than because of any technical issue. People reveal themselves early — if you’re paying attention.

Yes, we use Aracor to run high-speed, high-quality diligence across hundreds of documents.

But tools only matter if the humans involved are operating in good faith. Founders who want to build something real want you to see it clearly. If they don’t? That’s your answer.

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