Calling all Searchers — what’s the hardest part of evaluating a deal?

professional profile

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
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