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

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

Lenny's Podcast: Product | Career | Growth

May 24, 2026

Dan Shipper is the co-founder and CEO of Every, a media and software company that’s become a living laboratory for the future of work.
Speakers: Lenny Rachitsky, Dan Shipper
**Lenny Rachitsky** (0:00)
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 going to go through what else you predict will happen.

**Dan Shipper** (0:10)
The AI job apocalypse is not really a thing. I am super, super bullish on PMs and full stack designers.

**Lenny Rachitsky** (0:18)
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.

**Dan Shipper** (0:24)
I'm simultaneously extremely AI-pilled and very bullish on humans. Automation is a lot. Every agent needs a human. We have so much automation, so much AI, and I also work way more.

**Lenny Rachitsky** (0:34)
Creativity. It just feels like it's going to be more and more valuable to stand out from all the slop that people are shipping and launching constantly.

**Dan Shipper** (0:40)
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 have all this frozen human competence from yesterday. How do I use this to make something new and interesting?

**Lenny Rachitsky** (0:54)
What are some predictions for how the way we work is going to change?

**Dan Shipper** (0:57)
It's going to bifurcate in two main ways. One is everyone's going to 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 Claude Code work.

**Lenny Rachitsky** (1:12)
What you're predicting here is the SaaS tools will run within Codex or Claude Code.

**Dan Shipper** (1:17)
I think the SaaS apocalypse is dumb. I would buy SaaS stocks right now. What agents do is increase the number of users of SaaS, not get rid of it.

**Lenny Rachitsky** (1:24)
A lot of people are moving to CLI and trying to work from the terminal.

**Dan Shipper** (1:26)
We speed ran the CLI era. It was nice while it lasted, but I think CLIs are over.

**Lenny Rachitsky** (1:33)
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 non-technical person, uses Codex and Co-Work and Claude Code to get much of their work done. And this is why way before anybody else, Dan saw the rise of Claude Code and what is now Co-Work, 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 tried 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 lennysproductpass.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. Welcome back to the podcast.

**Dan Shipper** (3:01)
Thanks for having me. Always a pleasure to be with you.

**Lenny Rachitsky** (3:03)
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 Claude Code, and in particular Claude Code for non-engineering work, for just 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, the build on this very specific idea using Claude Code for non-technical work. A Codex is getting into this now. I imagine you've been seeing this. They're leaning into this non-technical use of basically coding agents. I feel like this has also been a big part of Anthropic Success over the past year, just how do non-technical people use this stuff.

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