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Matthew Prince Wants AI Companies to Pay for Their Sins

by Investor News Today
September 16, 2025
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Matthew Prince Wants AI Companies to Pay for Their Sins
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My proof that we’re onto one thing is we have seen a handful of content material offers, and the corporate that has gotten the very best deal by far is Reddit. We all know from their public filings that final 12 months they bought near $140 million a 12 months from Google and OpenAI.

Hmm.

If you happen to examine that with the same deal that was carried out for The New York Occasions, they bought about $20 million. So Reddit bought seven occasions greater than The New York Occasions. Why? Properly, possibly it is loopy …

I feel I do know the place you are going, and I am gonna agree with you, however [$140 million compared to $20 million is] a wildly completely different quantity.

Yeah. However 20 minutes in the past we each, I feel, agreed that we’re nostalgic for the quirky web …

Oh, I really like Reddit.

… and there is nothing that represents that greater than Reddit. The New York Occasions is wonderful, however if in case you have information from The New York Occasions, The Wall Avenue Journal, The Washington Publish, The Boston Globe, like how a lot actual distinction is there? Mainly the information keep the identical between these, whereas Reddit is that this distinctive content material, and so we have already got some proof that the enterprise mannequin of the AI-driven internet goes to be one which rewards the Reddits of the world extra.

All proper. I gotta determine what gap within the Swiss cheese I am gonna fill.

, the scariest assembly I’ve had within the final little bit was espresso with Anna Wintour. My spouse was like, “It’s important to put on a swimsuit.” And I’m like, “I don’t have something.”

Wait. That is actually essential. What did you put on, Matthew?

It was in New York and it was 100 levels outdoors, 100% humidity. The one swimsuit I had was this gentle blue, fall, comparatively heavy swimsuit. So, I wore the swimsuit.

Oh boy.

Anna in all probability rolled her eyes at this. However I additionally was only a sweaty mess. So I feel it was a fairly embarrassing assembly.

This can be a surprising visible. I am positive she thought it went nice. The factor about my boss is that she’s truly actually, very nice. So there you go.

She was extremely, extremely pretty, and so considerate about the entire content material and media business. So I actually appreciated the chance to get to choose her mind.

That is actually humorous.

Although my sartorial sense is fairly …

Belief me, so is mine. I do know the sensation.

Earlier than we finish, I wanna play a bit sport we got here up with. It is known as Management, Alt, Delete. What piece of tech would you’re keen on to manage? What piece would you alt, so alter or change, and what would you delete? What would you vanquish from the Earth if given the chance?

So, delete. I would in all probability say TikTok. Zero protein, very low-value content material, I feel, is actually harmful and damaging.

Um, management. I really feel tremendous privileged by way of what we do at Cloudflare, so I’d like to have vital affect in considering by means of what the following enterprise mannequin of the online appears like. I do not essentially wanna management it, however I’d like to no less than management ensuring that we’re rewarding filling the holes within the cheese.

Then, alt. I am nonetheless eager for a house automation system that does not suck. As a result of I confirmed up at my home in Austin and the sunshine switches did not work and I could not flip the TV on. , a wise house that was a bit bit smarter.


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