Eighteen months into a self-funded search, and I don't trust my own diligence yet.
I've got decent deal flow at this point and a system for filtering the noise. My real problem shows up once a deal actually lands and looks promising. I don't know the right questions to ask a founder to find the rot under the hood. I can't tell yet what a genuinely good business looks like versus one that's merely dressed up well for a sale. I know a good quality of earnings review and legal due diligence catch a lot of this, but I want to build my own eye for it too, not just outsource all my judgment. My biggest fear isn't finding nothing, it's confidently closing on something that's already quietly dying, and not having the pattern recognition to have caught it.
For those of you who've closed a deal, or walked away from one late, what were the signals you learned to spot, and how did you build that judgment. Did it come from a mentor, a bad near-miss, or just doing enough reps.