“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 BuildingConnected, having led their seed financing. BuildingConnected’s first and only acquisition was a company I founded called TradeTapp. Our team joined BC in 2018, and less than 6 months after that BC was acquired by Autodesk, where I continued on for about a year. As I started to explore new ideas, Dustin (DeVan, CEO of BuildingConnected) made sure Hunter was one of the first investors we spoke with.

HW: So then you ‘did your time’ at Autodesk post-BuildingConnected acquisition. What did you learn from the two acquisition experiences, and the whiplash of going from small startup -> bigger startup -> big public company that quickly?

JL: In short, a lot. I was pretty naive going into my first startup, having worked in more “traditional” roles within the construction…