MH

Matthew Harris

Things Matthew Says on Podcasts

Where to Find Them

Matthew Harris has been a guest on How I Invest with David Weisburd .

Recently: “E447: Anthropic at $2 Trillion? The AI Bubble, and Why the Best Startups Always Look Overvalued” on How I Invest with David Weisburd (October 2026).

What They Said

“Don't answer their questions. Kids ask questions all the time. And as a good parent, you want to be like, oh, my daughter wants to know why the sky is blue or whatever. It is not useful for you to answer their question. They will never remember the answers. Just say, why do you think? What do you think? Why do you think it's blue?” — Matthew Harris, How I Invest with David Weisburd

Harris, a father of six, says almost every parenting belief he had was knocked out by one kid or another. Only two rules survived: send them to a Montessori preschool, and don't answer their questions. He admits his kids find the second one incredibly annoying.

How I Invest with David Weisburd · 2026-10-26 Permalink → Listen →
How I Invest with David Weisburd Around 55:08 into the episode
Matthew Harris

…because I have 18, 15, 13, 9, 9, 7. So I've got kids that are doing stuff. I certainly have kids who have this sort of ineffable quality that people in the valley refer to as agency. And just because it's commonly said doesn't mean it's not important. I find it to be actually the defining. Do you

David Weisburd

get credit for that or were they just born that way?

Matthew Harris

…priors get knocked out by the kid number four. Turns out that rule isn't true, et cetera. In terms of parenting? Correct. In terms of human nature in general, but certainly in terms of parenting. The two rules that actually survive. One is Montessori preschool is just good. Just do that. They're actually very, very consistent. Wherever you live, you can find one, send your kids there. Two is don't answer their questions. Kids ask questions all the time. And as a good parent, you want to be like, oh, my daughter wants to know why the sky is blue or whatever. It is not useful for you to answer their question. They will never remember the answers. Just say, why do you think? What do you think? Why do you think it's blue? And so our kids find it incredibly annoying, particularly as they get older. They just want to know what subway stop to get off. That I would just commend that to you as a new dad. And congratulations, by the way. Just you have no obligation to answer their questions and you're not doing them any favors.

David Weisburd

And that builds in them these processes to answer their own questions. Correct.

Matthew Harris

And it's all about this agency. I mean, this is what the world demands right now: when faced with a blank screen, what are you going to do? And you have the ability of everything at your fingertips to do anything you want. Anything you don't know how to do, you just ask it and it tells you. And so…

David Weisburd

experienced parent, at least.

Speaker names from our own diarization · position estimated from where the line sits in the episode
“The companies that end up being massively valuable are overvalued, quote unquote, at every round. And so if you take a view that you're going to turn down things that are overvalued at the very moment in time they're being valued, you will systematically miss the power law companies on average.” — Matthew Harris, How I Invest with David Weisburd

Harris explains why his firm, Bain Capital Ventures, had good returns but too few huge winners. He says risk-management habits from Bain Capital's private equity and credit businesses crept in, and the firm balked at market prices when they got high. He names Databricks, Stripe and Ramp as companies that always looked expensive.

How I Invest with David Weisburd · 2026-10-26 Permalink → Listen →
How I Invest with David Weisburd Around 03:56 into the episode
Matthew Harris

…surely return multiples of its fund. So plenty of examples where in the future, once they're liquid, we can talk about them. There's not so much what are the returns, particularly in light of the fact that in recent years there have been fund returners just not yet liquid. But the why behind it.

David Weisburd

I imagine this is a pretty big issue. You guys must have discussed it internally. Why do you believe this has happened at Bain Capital?

Matthew Harris

…an outlandish proposition, to be sure. And this is actually the sort of thing we like. But where we struggled historically is sort of paying market price when market price got really high. And I think that that's a fundamental problem, actually, in a power law industry, because price is a signal of a sort. It can obviously be wrong, but the fact is like Databricks and Stripe and Ramp, I mean, the companies that end up being massively valuable are overvalued, quote unquote, at every round. And so if you take a view that you're going to turn down things that are overvalued at the very moment in time they're being valued, you will systematically miss the power law companies on average.

David Weisburd

How would you describe that so many of the winners are quote unquote overvalued?

Matthew Harris

We're talking about semantics here. I mean, in retrospect, they were undervalued, right? But on a multiple basis. They have extraordinary founders. They have extraordinary ambition. Those elements that led to them being these hyperscaled winners were present at the time. And thoughtful investors…

David Weisburd

episode is presented by Juniper Square, the operations partner for private markets. Early Bird from Europe did a study on this. They figured out that this price persistence continues to persist. In other words, like every round is overvalued versus the comps. So another way is that the…

Speaker names from our own diarization · position estimated from where the line sits in the episode

Collections They Appear In

Startups & Venture