Am I Too Picky, Or Just Picky Enough?
I'm about 8 months into my search, so this is a genuine question for the community. A few weeks ago I walked away from three deals in one week. There were different reasons each time: a hardware/software business I didn't want to run, a seller who clearly wanted his son to take over rather than selling, and a software business with annual contracts paid up front, where the seller wanted all the cash at close and none of the deferred revenue obligation that came with it. (His 90-minute demo, after he told me his sales process was one demo and one call, didn't help.) Over the last six months, I've walked from about a dozen businesses that fit my buy box, plus a handful more where I met the seller and didn't like the vibe. The one that I can't stop thinking about is the one that almost made it to LOI. We were negotiating terms when a resale partner cancelled their contract and roughly 20% of the revenue disappeared in a few weeks. The seller's investors didn't want to sell at the new number, so we agreed to reconnect in about six months. That wasn't a "no." It was a "not yet, and maybe not ever," which is harder to live with than a clean walk. So I'll ask y'all: when does killing fast stop being discipline and start being indecision?