Calling all Searchers — what’s the hardest part of evaluating a deal?
June 04, 2025
by a professional from University of Toronto in Toronto, ON, Canada
After spending time as a self-funded searcher, I’ve now started building tools to make the process less painful. But before going too far, I want to go back to first principles — and learn from you.
When you're deep in a deal, what’s the part that trips you up the most?
The first-pass model and research — trying to size the prize and pressure test assumptions?
The growth/operating strategy — figuring out what you’d actually do if you bought it?
The investor pitch — getting conviction across the line with your IC or your anchor?
Or is it some other piece entirely?
I’m not selling anything — just trying to learn what really slows people down, so I can build around actual bottlenecks, not imaginary ones.
Open to chat 1:1 or just trade thoughts over email — redacted
Appreciate any insight you’re willing to share.
— Shail