“I try not to ride the emotional wave of startup life like I sometimes did before” and other lessons from a second time founder

Shepherd’s CEO Justin Levine answers Five Questions on how his $6.2m fundraise came about & why it didn’t include me (yet)

I love working with great people and as a venture capitalist, am fortunate the number of founders I’m impressed by far exceeds our investment capacity. Here’s an example of a founder that I’ve known for a while who recently raised a seed round with different firms than ours. In industry terms, I’d call this a “miss/loss,” which VCs tend to not write about for obvious reasons (I’ve got a whole other rant on the fake performative anti-portfolio lists — Bessemer’s aside). But Satya and I post-mortem our miss/losses so I figured, why not do a version of it in public? My friend Alex at TechCrunch covered Shepherd’s seed round last September and here’s some more detail on how it all came about via my Five Questions with their cofounder/CEO Justin Levine.

Hunter Walk: Justin, thanks for agreeing to do this. I really enjoy our conversations and am especially glad you’re up for some candor, because it’ll help provide some insight into the state of the startup and funding market. Ok, first, let’s provide some backstory. You want to tell people how we originally met?

Justin Levine: Sure! Homebrew was on the board of a construction tech startup called…