Lenny's Podcast: Product | Career | Growth

The AI paradox: More automation, more humans, more work | Dan Shipper

1h 34mMay 28, 2026URL

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00:00Speaker 01

The last time you're on this podcast, you had this hot take that people were sleeping on Claude code. You were so unbelievably right. The premise of this episode is we're gonna go through what else you predict will happen. The AI jobpocalypse is not really a thing.

00:12Speaker 02

I am super, super bullish on PMs and full stack designers. You guys are hiring double than people in the past year, which is not what people would have expected from a company that is so AI forward. I'm simultaneously extremely AI pilled and very bullish on humans. Automation is a lie. Every agent needs a human. We have so much automation, so much AI, and I also work way more. Creativity. It just feels like it's gonna be more and more valuable to stand out from all the slop that people are shipping and launching constantly. What models do in general is they make yesterday's human competence cheap, and so it becomes commoditized. It's not valuable anymore. What humans do is we go in there, and we're like, yeah. We we have all this frozen human competence from yesterday. How do I use this to, like, make something new and interesting? What are some predictions for how the way we work is gonna change? It's going to in two main ways. One is everyone's gonna have at least one agent that they talk to that they can offload work to. Second is that most of the work that you do is actually going to happen on your computer in an environment like Codex or Cloud Cowork. What you're predicting here is the SaaS tools will run within Codex or Cloud Code. I think the SaaS apocalypse is dumb. I would buy SaaS docs right now. What agents do is increase the number of users of SaaS, not get rid of it. A lot of people are moving to CLI and trying to work from terminal. We speed ran the CLI era. It was nice while it lasted, but I think CLIs are over.

01:33Speaker 01

Today, my guest is Dan Shipper, CEO and founder of Every. Dan and his team are building maybe the most AI forward startup out there, and as a result, are very much living in the future of how work is going to look as AI becomes a bigger and bigger part of our day to day. Everybody at their company, including every nontechnical person, uses Codex and CoWork and Cloud Code to get much of their work done. And this is why way before anybody else, Dan saw the rise of Cloud Code and what is now CoWork, which he predicted almost a year ago when he was on the podcast last time. So I asked Dan to come back on the podcast to share his current biggest predictions for how work is going to change over the coming year for most people. We chat about what work will look like at most companies at the end of this year, how the shape of the work we do will change, and who will do best in this coming future slash what you need to be working on right now. Hint hint, product managers and designers are going to do very well. Dan makes a lot of bold predictions and many quite contrarian takes that I was not expecting him to say, and we are going to revisit this conversation exactly a year from today to see how much he got right. Before we get into it, do not forget to check out lenny'sproductpass.com for a free year of the hottest and most well crafted AI products in the world available exclusively to Lenny's newsletter subscribers. With that, I bring you Dan Shipper. Dan, thank you so much for being here, and welcome back to the podcast. Thanks for having me. Always a pleasure to be with you. The last time you were on this podcast, you had this kind of it was almost like an offhand hot take that people were sleeping on Cloud Code, and in particular, Cloud Code for non engineering work, for just, like, fixing files, sorting your hard drive, just all these things that people hadn't thought about. Nobody was talking about this. This was a year ago. You were so unbelievably right about this. It's just, like, unreal what has happened since then. They built Cowork, which was this whole they built on this very specific idea using Cloud Code for nontechnical work. Codex is getting into this now. I imagine you've been seeing this. They're like leaning into this nontechnical use of basically coding agents. I feel like this has also been a big part of Anthropic success over the past year, just like how do nontechnical people use this stuff. So you were just so ahead on this stuff. I I I even wrote a newsletter post building on this idea. I'm like, hey, this is interesting. I should dig into this. I asked people how to use Cloud Code for non engineering work, and I just had, like, so many examples, and it's like my second most popular posting.

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