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JL Jason Lemkin Jason Lemkin Founder of SaaStr, a community and media platform for B2B software founders, and managing director of SaaStr Fund; he previously co-founded EchoSign, acquired b...

“Never has such a successful startup maimed itself so poorly that I can think of as OpenAI. I mean, it would have killed almost any other startup what they went through, right?… Anthropic… owned the playbook for the chessboard for almost 12 months. There was no point in using any other coding solution… They literally letting Dario walk out the door rather than build it in-house and then firing the CEO and bringing him back over the night of long knives… talk about own goals, right?”

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch · Startups & Venture · October 2026

“Never has such a successful startup maimed itself so poorly that I can think of as OpenAI. I mean, it would have killed almost any other startup what they went through, right?… Anthropic… owned the playbook for the chessboard for almost 12 months. There was no point in using any other coding solution… They literally letting Dario walk out the door rather than build it in-house and then firing the CEO and bringing him back over the night of long knives… talk about own goals, right?” — Jason Lemkin, The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Context

Lemkin's reaction to Anthropic's S-1, after Rory O'Driscoll said OpenAI's leadership should be reflecting on decisions that let Anthropic pull ahead. Lemkin lists what he sees as OpenAI's self-inflicted wounds, above all ceding coding for about a year.

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Transcript

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch Around 13:27 into the episode
Harry Stebbings

Fasamultman reading this, thinking about Q1 going out himself, do you think he takes away anything from it, changes anything as a result of it?

Rory O'Driscoll

…away from you and do better. If there's any self-reflection, there should be a ton of that going on. Nothing you can do about it. You just got to get your business together and converge and get out yourself. And in the meantime, obviously compete aggressively on price to try and screw up their Q3.

Jason Lemkin

Never has such a successful startup maimed itself so poorly that I can think of as OpenAI. I mean, it would have killed almost any other startup what they went through, right? With the CO drama, all the other nonprofit to profit drama, the spike startup doing better than them. They basically let Anthropic control part of the market for almost a year, which is like five years or 10 years in AI time, right? There is a certain amount of parity with Astra and the OpenWaits models today, the best, but Anthropic fucking owned the playbook for the chessboard for almost 12 months. There was no point in using any other coding solution. And coding is the killer app, as Rory said 100 times. The math is true. They literally letting Dario walk out the door rather than build it in-house and then firing the CEO and bringing him back over the night of long knives. I mean, my God, I mean, it's all going to be okay. But talk about it, talk about own goals, right? I mean, every startup's full of them. This is just, these are some epic ones.

Harry Stebbings

I had the joy of having Sachinadella on 20 VC earlier this week. Great show. It was a fantastic guest to have on. Warden Orner. Microsoft had some pretty big news. That they were offering voluntary buyouts to 60,000 of its 223,000 employee base. It's an enormous amount of the employee base to get…

Jason Lemkin

First of all, Rory may have observed more of these than I have. Maybe he hasn't. I hope he hasn't. But it's not like all 27% are going to take it. Right. And they've already been through, I already think they already went through a 10% layoff round, right? So they've done, it's some sort of…

Rory O'Driscoll

Yes. I don't know. Whether 7%

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.

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