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

Every CEO Dan Shipper predicts that the future of work will unfold inside AI coding tools like Codex and Claude Code, with every company eventually running a single “super-agent” in Slack that employees interact with daily. Shipper argues that automation is a lie, SaaS is not dead, and the AI job apocalypse is not happening—instead, forward deployed engineers will become the most essential role, and humans will read and enjoy far more AI-generated writing.

read3 min publishedMay 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. 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.

Listen on YouTube, Spotify, and Apple Podcasts

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:

** WorkOS**—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more

** Vanta**—Automate compliance, manage risk, and accelerate trust with AI

Where to find Dan Shipper:

• LinkedIn: [https://www.linkedin.com/in/danshipper/](https://www.linkedin.com/in/danshipper/)

• Podcast: [https://every.to/podcast](https://every.to/podcast)

• Website: [https://danshipper.com](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](https://claude.com/product/cowork)

• Codex: [https://chatgpt.com/codex](https://chatgpt.com/codex)

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

• Every: [https://every.to](https://every.to)

• Kieran Klaassen on X: [https://x.com/kieranklaassen](https://x.com/kieranklaassen)

• Cora: [https://cora.computer](https://cora.computer)

• Kate Lee: [https://every.to/@kate_1767](https://every.to/@kate_1767)

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

• OpenClaw: [https://openclaw.ai](https://openclaw.ai)

• Shopify: [https://www.shopify.com](https://www.shopify.com)

• Ramp: [https://ramp.com](https://ramp.com)

• Brandon Gell on LinkedIn: [linkedin.com/in/brandongell](http://linkedin.com/in/brandongell)

• Proof: [https://every.to/on-every/introducing-proof](https://every.to/on-every/introducing-proof)

• Devin: [https://devin.ai](https://devin.ai)

• Cursor: [https://cursor.com](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](https://www.spacex.com)

• GitHub: [https://github.com](https://github.com)

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

• General Assembly: [https://generalassemb.ly](https://generalassemb.ly)

• Marcus Moretti: [https://every.to/@marcus_fd8302_1](https://every.to/@marcus_fd8302_1)

• Spiral: [https://every.to/on-every/introducing-spiral](https://every.to/on-every/introducing-spiral)

• Axios: [https://www.axios.com](https://www.axios.com)

• Hermes: [https://hermes-agent.nousresearch.com](https://hermes-agent.nousresearch.com)

• Viktor: [https://www.viktor.ai](https://www.viktor.ai)

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

• Alex Honnold: [https://en.wikipedia.org/wiki/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](https://www.hbomax.com/shows/100-foot-wave/34e489ad-2eca-4078-adb6-6d2b521b407e)

• Rob Burbea talks: [https://www.youtube.com/@boubabuddha/playlists](https://www.youtube.com/@boubabuddha/playlists)

• David Goggins: [https://en.wikipedia.org/wiki/David_Goggins](https://en.wikipedia.org/wiki/David_Goggins)

Recommended books:

• *The Golden Compass*: [https://www.amazon.com/Golden-Compass-His-Dark-Materials/dp/0807204714](https://www.amazon.com/Golden-Compass-His-Dark-Materials/dp/0807204714)

• *The Writing Life*: [https://www.amazon.com/Writing-Life-Annie-Dillard/dp/0060919884](https://www.amazon.com/Writing-Life-Annie-Dillard/dp/0060919884)

• *The Second World War*: [https://www.amazon.com/Second-World-War-Volumes/dp/B005NS30ZG](https://www.amazon.com/Second-World-War-Volumes/dp/B005NS30ZG)

The Rigor of Angels: Borges, Heisenberg, Kant, and the Ultimate Nature of Reality: https://www.amazon.com/Rigor-Angels-Heisenberg-Ultimate-Reality/dp/0593315073

The Power Broker: Robert Moses and the Fall of New York: https://www.amazon.com/Power-Broker-Robert-Moses-Fall/dp/0394720245 Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

Lenny may be an investor in the companies discussed.

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