Ben Gilbert: belief

Transcript context

…A lot of my investments I've written about. A lot of investments, frankly, come in because I start writing about Web 3.0. I wrote something like the cooperation economy that unlocks how somebody thinks about something and then they want to start it. I've had that conversation with founders a few times where they're like, we make all of our employees read this because this is what we're trying to do. That helps on the sourcing and winning deal side, but this wasn't planned either. So I think the next iteration of Not Boring or whatever we add on top here, it probably won't be planned and it probably be because it makes sense with what I'm doing, but I could not do this. I didn't plan it, that's why I couldn't do this if I didn't have some sort of skin in the game with what's going on here. I like being honest when I get [...]. Bill.com, my worst call of all time being [...] bill.com. Really, the only time I've ever gotten kind of pessimistic. I like being called out when I'm wrong on stuff. I think to be able to run a venture fund that says, cool, here are the ideas, but then also, I'm putting money behind it. You'll see the results in how well fund one, fund two, fund three did, and whether I'm just fully talking out of my ass or only partially talking out of my ass and got lucky a little bit in the results of how these funds do. It does seem like you're publishing pretty much. I think on Saturday, you send out the email to LPs, and then come Monday you send out a public version, and it's pretty much the same. Obviously, there are some things that the companies don't want you sharing. But other than that, it's a remarkably transparent way of going about venture investing. It's also super different from classic venture capital. Did you lead a single round? Did you write any term sheets? Were you the biggest check in any one of those 91 investments? Never, and that's all part of the strategy. We all love talking about strategy. Strategy isn't doing everything well. It's picking what things you want to do well and taking advantage of those things. Even figuring out how to price the round, figuring out what should go into the term sheet, spending time negotiating that, and then being on a board, God forbid. It actually just doesn't work with my strategy because it is a house of cards already, where you move one thing and the whole thing breaks. If I'm doing the more deeply time-consuming parts of the venture, at least as I'm currently constructed, it doesn't work. But it really works very well when I can talk to a founder and we have this specific area—either internally or externally—where I can be helpful. Not to make fun of that venture pun but—…

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