Introducing Initialized Capital

Just wanted to echo the sentiments about having an investor/friend who sticks with you through the thick/thin. I think some investors are all about downside protection and it usually manifests in legal instruments that benefit the investor if anything goes wrong, but more importantly, you can tell by the way you're treated. It's rare that investors don't have the "game" change them. They start to focus on their returns, care only about a few number of winners (when in fact, writing the check is just the beginning to making sure you have an active winning investment). Lots of these investors completely forget why they are VCs in the first place.

When Esper was changing from an AI assistant company to a calendar analytics company, we went through one of these moments. Some investors were immature frantically trying to find an edge, while some others did everything in their power to help us transition. When things get tough, you realize who has grit.

I remember thinking that Garry was uncannily nice with us during this trying time (to be fair, I've known him since we were both founders and consider him one of my best friends in the bay area). He was always solutions oriented, introducing us to people, thinking through problems and just giving more of his and the Initialized team's time than probably we warranted. The reason why he was that way was because he cares about you (the founders and the team) to tackle a problem you care about. He would always say that when he started investing - "I'm just afraid of being a straight vampire" i.e. an investor who is just leeching off a growing beast.

In a weird way, he's the type of investor, similar to how PG describes great companies - they're kind of like non-profits. They just want to solve problems and it'll work out. That's probably the reason why he's done so well.

Anyway, respect him because he sure as hell respects you.

I love the bay area. Worked at startups there off and on for over twenty years. But it's precisely because its the center of the universe that when I start my next company, I'm going to do it somewhere else. I do love it there though.

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