Michael Gilroy

speaker

885 appearances 1 recordings 1 series first heard Jul 2026 last heard 20 Jul

Michael Gilroy’s voice in public audio — every appearance, attributed to the second.

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recordings per month · last 12 months

Recordings per month over the last 12 months — 1 in all, peaking in Jul 2026 with 1.

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How I Invest with David Weisburd · E405: Why AI Has Made Venture Capital Harder (Not Easier) · 20 Jul 2026 podcast

And so if we sat here today and said, Hey, which one of these is Anthopic most likely to disrupt?

I think you'd probably say block before toast, right?

Again, just because of the horizontal nature of it.

So it requires a lot of work and customer calls.

You cannot replicate

knowing the customer without making 10, 20, 50 calls over the course of looking at a trend and decided to make an investment there.

That's exactly right.

And again, we are using AI all throughout our business, but we are really leaning into the human component of it.

We do two to three deals a year.

And this is really why we started the firm, because we want to spend a lot of time prosecuting on an idea and making sure we are prepared.

And that's how we win.

That part of our business is unchanged other than the fact that AI has been phenomenally helpful in finding those companies and founders, right?

AI for us internally, phenomenal top of funnel, phenomenal keeping us on process and organized.

It's taking everything we're doing and saying, hey, we're missing these things or not.

But look, ultimately, it's our job to go out and meet every single company and all of the trends that we care about, spend real time with the founders.

And then you make a risk adjusted decision of, hey, do we feel like this founder and team are differentiated enough in this landscape of 20 or 25 companies again, because there's so many more now.

If we can't make that decision, let's wait for the series A. If we can't make that decision there, let's wait for the series B. The biggest mistake you can make in our business is backing the number two, three or four business in any given market that ends up working.

Because, man, if you're right on the trend and you're right on the market and the rust is there, but you just happen to pick the number two or number three, not only do you lose money, but it's the opportunity cost of putting a lot more money into a business that's going to make money for ourselves and for our investors.

It is at the growth stage where they're playing, right?

At the

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