Three small seats close to where money gets decided — a search fund, a venture firm, and a boutique advisory — plus the little company I ran before any of them. I kept picking rooms that would teach me how businesses like the ones I want to build actually get priced.
A short summer inside a boutique advisory — comps, precedent transactions, and drafts of the documents that go out with a company when it's for sale. Mostly I was learning the difference between a business that's good and a business that's sellable. Not always the same thing.
Sat close to a $5.5M Series A extension — watched a note become ownership on a cap table, wrote memos, and helped source and diligence early-stage B2B software. Mostly I got to see how a small check gets to yes.
My longest stretch, and the one I learned the most from. Sourced and screened 200+ lower-middle-market targets, underwrote things like EBITDA quality, customer concentration, and owner-succession, and wrote screening memos for the IC. Got tired of doing research the slow way and built AI workflows (Claude, ChatGPT) the fund adopted across sourcing — saved about fifteen hours a week.