“Any Favorites?” The Worst Question to Ask Me About Homebrew’s Investments

A year into my career as a seed stage investor, I’m starting to get the hang of some standard conversations.

For example, when one VC says to another investor “I’d love to find something to do together,” it means “I’m not going to show you any of my deals but if you invest in something amazing, tell me.”

But there’s one question that I hate being asked: “Which Homebrew investments are your favorite?” or any similar variation. It’s a question that not only won’t I answer, I don’t even know how. We’ve backed 14 teams thus far and there’s no force ranking for how I feel about them. Maybe the expectation is that my “favorite” is the one that’s performing best at the moment or marked up most from our initial investment. Maybe it’s the company getting the most press, or which has tweeted about how great Homebrew is, or has the most celebrity investors. Maybe it’s the one that I actually need to work hardest to push, “Oh yeah, these guys are awesome. You should get into their next round.”

But in actuality none of those conditions could help me identify a favorite. I might highlight different companies for you based on your interests as (a) an investor, (b) reporter, (c) potential employee, and so on, but that’s about what you need, not my own preferences.

We’ve invested in a collection of founders who are working hard every day to inspire their teams, build their products, grow their community. Their nearterm success or failures don’t impact whom I like more or less. Their triumphs or struggles as leaders doesn’t elevate one over another or cause me to write someone off. While my appreciation and fondness for them isn’t unconditional it can’t be allocated proportionately across our companies like reserve capital. So don’t ask me.

sidenote: Earlier teased this post via Twitter by saying I was going to write about the “dumbest” question to ask a VC, but what I really meant was the question I hate being asked. In response to my original characterization, a number of people posited I was going to cover why VCs don’t sign NDAs but Brad Feld has one from 2006 that still holds true. 

2 thoughts on ““Any Favorites?” The Worst Question to Ask Me About Homebrew’s Investments

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