Was talking with a fellow VC the other day who had just decided, after substantial deliberation, not to invest in a startup he was evaluating. “I hope I’m right [to pass],” was his comment, reflecting the uncertainty in his mind.

“Really? I hope you’re wrong,” was my reply.

Not because I’m an asshole (that’s besides the point), but instead it’s so much more fun to root for a team’s success regardless of whether or not you’ve backed them. The number of founders who I truly am excited about as people is so much greater than total investments we make each year (~15) — we leave many pitch meetings honestly hoping they build something meaningful, regardless of whether we’re able to participate in that outcome.

We’re investing our own personal capital in Homebrew IV so when we do commit to a company, it’s as close to literal skin in the game as you can get without being on the org chart. But regardless, false negatives in decision making is definitely part of being in venture. As I’ve found, if you haven’t passed on some billion dollar companies you probably haven’t backed any either. Homebrew has invested in a bunch, passed on an equal or great amount, and even lost several in competitive situations.

I wonder how transparent this is to founders? When they hear a ‘hey, we’re not going to participate in this round’ can they tell whether the investor is still rooting for them or not. Is the offer to ‘help if we can anyways’ sincere or not? How many of us actually ‘root’ from the sidelines versus just say it?