Jessica Lessin, founder and CEO of The Information, explains why she had a past falling out with venture capitalist Bill Gurley during reporting on Uber.
“We thought we had Bill Gurley's cell phone. It turned out we had his gatehouse phone. So upon calling it, our reporters in our newsroom were just calling it, and he thought we were hiding in the bushes.”
quote is from the automated transcript, cleaned for reading:
filler sounds and stutters are removed, nothing is rephrased. names can be misheard
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More from Jessica Lessin
AssertionPartly supported
Lessin: Trial revealed Altman paid Brockman $10M from family office
“It was revealed that Altman, because it was a nonprofit back then, was paid Greg ten million dollars out of his, like, own family office and kept it from Elon, and so all these sort of alliances were being formed beneath the surface, and it just seemed like a …”
Jessica LessinMay 8, 2026▶ 41:23Why the Met Gala Hates Tech, Elon vs OpenAI Drama, and the Rise of Chinese AI Models · More or Less Podcast
AssertionSupported
Lessin: Leaked OpenAI memo targeted Anthropic's ARR math and compute investment
“There was a memo that was leaked from OpenAI, an OpenAI memo that was leaked. I think it was in OpenAI's interest for this memo to be out there. I also think it was written in a way where they wanted it to be out there, where they came after Anthropic. Both fo…”
Jessica LessinApr 17, 2026▶ 27:05Allbirds Pivoted to AI Data Centers | SpaceX $1.5T IPO, Anthropic $800B, $175M Seed Rounds
AssertionNot checkable as stated
Lessin: Tech Execs Privately Reject the US-China AI War Narrative
“In Washington tech execs go to Washington to say, we have to be trying to an AI at all costs privately, or even semi privately. The exact same people say, obviously the U S and China are going to both be leaders at AI. They sort of reject that the war narrativ…”
Jessica LessinJul 31, 2026▶ 29:52The Lilian Weng Saga, Mental Health Essay Then OpenAI | Meta's AI Ad, China Cracks DUV
AssertionPartly supported
Jessica Lessin: Stripe is attempting to acquire PayPal
“The Information has a big Stripe financial scoop that is worth discussing because. We have not discussed Stripe in a while and it is trying to buy PayPal.”
Jessica LessinJul 24, 2026▶ 37:45Stripe Is Trying To Buy PayPal For $150b | OpenAI Cyber Incident, Frontier Model Economics, Peptides · More or Less Podcast
AssertionSupported
Lessin: Stripe Is Teaming Up With Advent for PayPal Bid
“So what they're doing for this PayPal takeover offer, which, you know, is, is just that, like, no sign that any deal is done, and I'm sure other bidders will emerge and whatever, but they're teaming up with Advent, which is a private equity firm,”
Jessica LessinJul 24, 2026▶ 43:19Stripe Is Trying To Buy PayPal For $150b | OpenAI Cyber Incident, Frontier Model Economics, Peptides · More or Less Podcast
PredictionOpen · timeframe Sep 2026
Jessica Lessin: Anthropic will go public by September
“Anthropic will go public. I would be shocked if they're not public in September.”
Jessica LessinJul 17, 2026▶ 2:55Open Source AI Wins. Now Labs Are Running to Washington |Thinking Machines, Johnny Ive, Realtime API · More or Less Podcast
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