Brian O’Malley

My colleague Alex and I put a piece out on last summer, which is really how do you leverage some of these AI technologies, but ultimately deliver it in a traditionally human service category, but do so with high technology level gross margins versus much lower service margins.

And so if you look at the intersection of those areas, that's very much what I'm excited about today.

But one of the real pleasures of this job is the ability to sit down with other seed investors, other angels and just say, hey, which founder did you guys back that's been most inspiring to you guys where you're just really excited about what they're building?

And a lot of times that will open the door for us to look at things that we never really even thought of as being exciting.

But we're able to get inspired by that founder's vision.

And it's a lot of fun to be able to go explore things both that I know a lot about, as well as get exposure to things that I very limited knowledge and I need to come up come up to beat quite quickly on.

One of the themes in the market is that the large multistage firms that we talked about, the Sequoias and Andreases, are going down and competing in the sometimes even the pre-seed round, but usually the seed round.

Let's say Doug Leone from Sequoia is pitching against you, not an unviable position.

How do you differentiate yourself and how do you get into that round versus Sequoia?

Doug's going to be a tough one to beat.

So I don't know if I want to go ahead against that one.

But I am happy competing with the best firms in the world because that means I'm barking up the right trees.

So a lot of it really just comes back to first principles where I want to show up for that conversation more prepared, more informed than whoever I'm competing against.

And some of that involves really understanding what is happening recently in terms of new capabilities.

And some of that is having a much more longitudinal background where I know what happened with companies that tried similar things five, 10 plus years ago.

You think about early investors in Instacart, you had an intimate knowledge around what happened with Webvan.

You're going to be much more prepared to be helpful, to give guidance to those new companies.

And so a lot of it is just back to basics.

And then we'll throw in a few unique things along the way.

One of the things we can do as a smaller firm that's harder to do if you're larger, where we don't need to own quite as much of the business, we don't need to write quite as big of a check, we'll do something that I call flash syndicate.