The AI paradox: More automation, more humans, more work | Dan Shipper
5/24/20261 hr 34 min
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. Everyone at his company of about 30 people is an AI early adopter; from editors to ops people, they use AI to do much of their work, giving Every a unique lens into where the world is heading. A year ago on this show, Dan predicted that people were sleeping on Claude Code for nontechnical work, which proved to be remarkably prescient. Today he’s back with another set of calls: the SaaS apocalypse is dumb, CLIs are over, the forward deployed engineer is the most valuable new hire, and the only thing you need to do to stay employed is ride the models.
Dan’s predictions:
1. The future of work will happen inside Codex or Claude Code.
2. Every company will have one “super-agent” inside their Slack that every employee talks to regularly.
3. SaaS is not dead—in fact, Dan is bullish on SaaS stocks. His contrarian take: “I would buy SaaS stocks right now.”
4. SaaS economics will shift: users will bring their own AI tokens into apps, which actually improves SaaS margins.
5. PMs will thrive in the AI era.
6. Full-stack designers will become superheroes.
7. The AI job apocalypse is not happening.
8. Forward deployed engineer is the new most essential role.
9. CLIs are over.
10. Automation is a lie.
11. We will read way more AI-generated writing and we will like it.
12. We’ll be building software for humans and agents to use together.
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Episode transcript: https://www.lennysnewsletter.com/p/the-ai-paradox-dan-shipper
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Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
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Where to find Dan Shipper:
• LinkedIn: https://www.linkedin.com/in/danshipper/
• Podcast: https://every.to/podcast
• Website: https://danshipper.com
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction to Dan Shipper
(02:56) Dan’s unique position living in the AI future
(09:17) How the way we work will change in the coming year
(16:39) The case for general agents
(18:08) Codex and Claude Code as the new operating system for work
(25:39) How Cursor fits in
(27:42) How this changes what SaaS companies should build
(31:13) Why CLI is already over
(33:34) Two agents are better than one
(36:22) Why Dan is bullish on SaaS stocks
(39:01) Why automation doesn’t reduce human work
(47:00) The value of human-written code
(48:36) Quick recap
(50:15) How work is changing
(56:17) Why data scientists are drowning in bad analysis
(58:24) Which product/tech roles are least changed by AI
(1:02:17) We will read way more AI-generated writing and we will like it
(1:08:28) Why product managers will dominate the AI era
(1:11:05) Full-stack designers are the other big winners
(1:13:11) The AI job apocalypse won’t happen
(1:16:00) How to “ride the models” to stay relevant
(1:21:02) Final predictions and advice
(1:25:24) Lightning round
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References: https://www.lennysnewsletter.com/p/the-ai-paradox-dan-shipper
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
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Lenny may be an investor in the companies discussed.
To hear more, visit www.lennysnewsletter.com
Clips
Transcript preview
First 90 secondsLenny Rachitsky· Host0:00
The last time you were 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.
Dan Shipper· Guest0:10
The AI jobpocalypse is not really a thing. I am super, super bullish on PMs and full stack designers.
Lenny Rachitsky· Host0:18
You guys are hiring, doubled in people in the past year, which is not what people would've expected from a company that is so AI forward.
Dan Shipper· Guest0:24
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.
Lenny Rachitsky· Host0:34
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.
Dan Shipper· Guest0:40
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, we have all this frozen human competence from yesterday. How do I use this to, like, make something new and interesting?"
Lenny Rachitsky· Host0:54
What are some predictions for how the way we work is gonna change?
Dan Shipper· Guest0:57
It's going to bifurcate 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 Claude Cowork.
Lenny Rachitsky· Host1:12
What you're predicting here is the SaaS tools will run within Codex or Claude Code.
Dan Shipper· Guest1:17
I think the SaaS-pocalypse 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· Host1:24
A lot of people are moving to CLI and trying to work from the terminal.
Dan Shipper· Guest1:26
We speed ran the CLI era. It was nice while it lasted, but