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Published · transcript-backed

Dan Shipper: evaluation

24 May 2026 Lenny's Podcast The AI paradox: More automation, more humans, more work | Dan Shipper

“I definitely want to be the one to think about what it should say, what it should say, but the actual sentences don't matter that much to me usually.”

— Dan Shipper

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Speaker
Dan Shipper
Attribution
Verified speaker
Claim type
evaluation
Recorded
24 May 2026
Publisher
Lenny's Podcast

Transcript context

…Right. Most people are really bad at writing strategy documents. The bar is low. Yeah. And same thing with email. Most of my email is written by GPT 5.5 in Codex right now. And I honestly would prefer it to say that it's coming from GPT 5.5 and I may change it to do that. But I had this experience the other day where I had to send an email to one of our investors and I asked Codex to go do it. And Codex knows to ask me and it usually does, but this time it didn't and it just sent the email and I didn't look at it at all and I was like, "Fuck." And so I went to my sent and looked at it and I was like, "Oh, this is exactly what I would've sent." And so it's pretty close to that a lot of the time. It can be a little overformal and there's a couple of things that... It's just when you really think about it, most of your email is kind of... It's kind of wrote. It's kind of prosaic. I definitely want to be the one to think about what it should say, what it should say, but the actual sentences don't matter that much to me usually. Sometimes I do a lot and this is coming from a writer. I care a ton about writing. I think that human writing is incredibly important and I expect we only publish human writing. Well, actually we publish a mix of human and AI writing, but we always label it. Sometimes it's nice to have an AI co-author on certain things. I absolutely think that human writing is important and I think that the reaction or the aversion to AI writing is silly. It's such an interesting lens on that because when people think about AI writing, I think about social media and videos and your point is internally, if you're just working on planning and documents and email and things like that, that is much less scary that it's AI written. And to your point, people are already doing this, you almost prefer it a lot of times because people are really bad at doing anyway.…

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