The AI paradox: More automation, more humans, more work

Lenny's Podcast: Product | Career | Growth

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

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

Why most work will happen inside Codex or Claude Code, the CLI era is over, every agent needs a human, and why he’s wildly bullish on PMs and designers

Lenny Rachitsky

May 24, 2026

∙ Paid

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.

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Dan’s predictions:

The future of work will happen inside Codex or Claude Code.
Every company will have one “super-agent” inside their Slack that every employee talks to regularly.
SaaS is not dead—in fact, Dan is bullish on SaaS stocks. His contrarian take: “I would buy SaaS stocks right now.”
SaaS economics will shift: users will bring their own AI tokens into apps, which actually improves SaaS margins.
PMs will thrive in the AI era.
Full-stack designers will become superheroes.
The AI job apocalypse is not happening.
Forward deployed engineer is the new most essential role.
CLIs are over.
Automation is a lie.
We will read way more AI-generated writing and we will like it.
We’ll be building software for humans and agents to use together.

Brought to you by:

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Where to find Dan Shipper:

• X: https://x.com/danshipper

• LinkedIn: https://www.linkedin.com/in/danshipper/

• Podcast: https://every.to/podcast

• Website: https://danshipper.com

Referenced:

• The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder/CEO of Every): https://www.lennysnewsletter.com/p/inside-every-dan-shipper

• Claude Cowork: https://claude.com/product/cowork

• Codex: https://chatgpt.com/codex

• Everyone should be using Claude Code more: https://www.lennysnewsletter.com/p/everyone-should-be-using-claude-code

• Every: https://every.to

• Kieran Klaassen on X: https://x.com/kieranklaassen

• Cora: https://cora.computer

• Kate Lee: https://every.to/@kate_1767

• METR (Model Evaluation and Threat Research): https://metr.org

• OpenClaw: https://openclaw.ai

• Shopify: https://www.shopify.com

• Ramp: https://ramp.com

• Brandon Gell on LinkedIn: linkedin.com/in/brandongell

• Proof: https://every.to/on-every/introducing-proof

• Devin: https://devin.ai

• Cursor: https://cursor.com

• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell

• SpaceX: https://www.spacex.com

• GitHub: https://github.com

• Lenny’s post on X on AI changing job responsibilities: https://x.com/lennysan/status/2054664138039992600

• General Assembly: https://generalassemb.ly

• Marcus Moretti: https://every.to/@marcus_fd8302_1

• Spiral: https://every.to/on-every/introducing-spiral

• Axios: https://www.axios.com

• Hermes: https://hermes-agent.nousresearch.com

• Viktor: https://www.viktor.ai

• The Dark Wizard on HBO: https://www.hbomax.com/shows/dark-wizard/76e78c26-21c9-45b4-b84b-4c3e1f8ff763

• Alex Honnold: https://en.wikipedia.org/wiki/Alex_Honnold

• 100 Foot Wave on HBO Max: https://www.hbomax.com/shows/100-foot-wave/34e489ad-2eca-4078-adb6-6d2b521b407e