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Can Bill Gross Save The Internet From AI?

7 min readJun 19, 2025

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ProRata feels an awful lot like Overture, the company that taught Google how to make money.

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Bill Gross, boiler of oceans.

Bill Gross has been here before.

Back when the Internet was young, when the dot-com wave broke across the monied shoals of Wall Street opportunism, Gross built a world-changing company, took it public, then sold it for billions.

Google was a fledgling startup with no discernible business model when Gross pioneered a revolutionary approach to Internet advertising now known as “paid search.” It seems obvious today, but in 1998, the notion that advertisers could buy search keywords and only pay if people clicked on their ad — well, that idea was bonkers.

So bonkers, in fact, that when Gross launched Goto.com at TED in February of 1998, the audience booed and hissed while he was on stage. The gall of this man! This bespeckled, wiry, manic guy from Los Angeles of all places — he wanted to ruin the Internet by putting a price tag on search results!(1)

Despite the initial response from the TED crowd, Goto flourished, growing through the dotcom crash that devastated most of the early Internet industry. Knowing he could never catch the portals dominating early Internet traffic, Gross pivoted his company to a syndication model…

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John Battelle
John Battelle

Written by John Battelle

A Founder of DOC, The Recount, NewCo, Federated Media, sovrn Holdings, Web 2 Summit, Wired, Industry Standard; writer on Media, Technology, Culture, Business