The AI paradox: More automation, more humans, more work | Dan Shipper
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.
—
Brought to you by:
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny
Vanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny
—
Episode transcript: https://www.lennysnewsletter.com/p/the-ai-paradox-dan-shipper
—
Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
—
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
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
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
—
References: https://www.lennysnewsletter.com/p/the-ai-paradox-dan-shipper
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
—
Lenny may be an investor in the companies discussed.
To hear more, visit www.lennysnewsletter.com
The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder/CEO of Every)
Dan Shipper is the co-founder and CEO of Every. With just 15 people, Every publishes a daily AI newsletter, ships multiple AI products, and operates a million-dollar-a-year consulting arm—all while their engineers write virtually zero code. It’s the most radical example of AI-first operations, and Dan is a prolific writer who has become a leading voice on how AI is transforming the way we build and work.
Learn:
1. Why Dan thinks AI won’t steal jobs en masse—and may actually reshore many jobs to the U.S.
2. The most underrated AI tool for non-programmers
3. An inside look at Every’s AI-first workflow
4. Why every company needs an “AI operations lead”
5. How Dan’s team uses an arsenal of AI agents (Claude, Codex, “Friday,” “Charlie”) in parallel, treating each AI like a specialist with unique strengths
6. Why generalists will thrive in an AI-first world, as rigid job titles blur and everyone becomes a “manager” of AI tools
7. Dan’s playbook for making any company AI-first—from the CEO setting the example, to hosting internal prompt-sharing sessions, to upskilling teams on AI tools
—
Brought to you by:
CodeRabbit—Cut code review time and bugs in half. Instantly: https://coderabbit.link/lenny
DX—A platform for measuring and improving developer productivity: https://getdx.com/lenny
PostHog—How developers build successful products: https://posthog.com/lenny
—
Transcript: https://www.lennysnewsletter.com/p/inside-every-dan-shipper
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/167681269/my-biggest-takeaways-from-this-conversation
—
Where to find Dan Shipper:
• X: https://x.com/danshipper
• LinkedIn: https://www.linkedin.com/in/danshipper/
• Podcast: https://every.to/podcast
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Welcome and introduction
(04:04) Hot takes on AI and job reshoring
(07:06) The power of Claude Code for non-coders
(14:35) The future of AI in business operations
(18:45) AI’s role in enhancing human skills
(22:26) The evolution of AI tools and their applications
(25:40) Building an AI-first company
(29:50) Innovative AI operations and team dynamics
(35:35) Dan's AI stack
(41:26) Compounding engineering
(48:29) The impact of AI on learning and development
(50:10) Accelerating career growth with AI
(51:36) Revolutionizing code review and workflow
(53:07) The importance of coding knowledge
(57:26) Building AI-driven products
(01:02:01) Innovative fundraising strategies
(01:08:45) Consulting and AI adoption in companies
(01:17:01) The allocation economy and future skills
(01:20:12) The value of generalists in the AI age
(01:24:07) Lightning round and final thoughts
—
Referenced:
• Claude Code: https://www.anthropic.com/claude-code
• Gemini CLI: https://blog.google/technology/developers/introducing-gemini-cli-open-source-ai-agent/
• Microsoft Copilot: https://copilot.microsoft.com/
• Cursor: https://www.cursor.com/
• Base44: https://base44.com/
• Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo: https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo
• 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
• Plato’s Argument Against Writing: https://fs.blog/an-old-argument-against-writing/
• From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products | Peter Deng: https://www.lennysnewsletter.com/p/the-quiet-architect-peter-deng
• Granola: https://www.granola.ai/
• Tobi Lutke’s post on X about context engineering: https://x.com/tobi/status/1935533422589399127
• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook
• Every: https://every.to/
• Cora: https://www.cora.computer/
• Sparkle: https://makeitsparkle.co/
• Spiral: https://spiral.computer/
• Lex: https://lex.page/
• Nathan Baschez on LinkedIn: https://www.linkedin.com/in/nbashaw/
• Kate Lee on LinkedIn: https://www.linkedin.com/in/kate-lee-506768/
• Katie Parrott on LinkedIn: https://www.linkedin.com/in/katieparrott/
• Animalz: https://www.animalz.co/
• Rachel Woods on X: https://x.com/rachel_l_woods
• Nityesh Agarwal on LinkedIn: https://www.linkedin.com/in/nityeshaga
• Claude Opus 4: https://www.anthropic.com/claude/opus
• Codex: https://openai.com/index/introducing-codex/
• Superwhisper: https://superwhisper.com/
• Wispr Flow: https://wisprflow.ai/
• Notion: https://www.notion.com/
• Kieran Klaassen on LinkedIn: https://www.linkedin.com/in/kieran-klaassen/
• Friday: https://www.friday.run/
• Charlie: https://www.gocharlie.ai/product/ai-agents/
• Avengers: https://en.wikipedia.org/wiki/Avengers_(Marvel_Cinematic_Universe)
• Alex Duffy on LinkedIn: https://www.linkedin.com/in/alex-d/
• Danny Aziz on LinkedIn: https://www.linkedin.com/in/dannyaziz/
• Dia: https://www.diabrowser.com/
• Reid Hoffman’s website: https://www.reidhoffman.org/
• Starting Line VC: https://www.startingline.vc/
• Walleye Capital: https://walleyecapital.com/
• At This $10 Billion Hedge Fund, Using AI Just Became Mandatory: https://every.to/podcast/at-this-10-billion-hedge-fund-using-ai-just-became-mandatory
• Reflexive AI usage is now a baseline expectation at Shopify: https://x.com/tobi/status/1909251946235437514
• Klarna CEO Sebastian Siemiatkowski on Getting AI to Do the Work of 700 Customer Service Reps: https://www.sequoiacap.com/podcast/training-data-sebastian-siemiatkowski/
• The Pin Factory: https://www.adamsmithworks.org/pin_factory.html
• Deadwood on HBO: https://www.hbo.com/deadwood
• Joel Spolsky on X: https://x.com/spolsky
• Jason Fried’s website: https://world.hey.com/jason
• Jason Fried challenges your thinking on fundraising, goals, growth, and more: https://www.lennysnewsletter.com/p/jason-fried-challenges-your-thinking
• Sam Harris’s website: https://www.samharris.org/
• Bill Simmons on X: https://x.com/billsimmons
—
Recommended books:
• War and Peace: https://www.amazon.com/War-Peace-Vintage-Classics-Tolstoy/dp/1400079985
• Anna Karenina: https://www.amazon.com/Anna-Karenina-Leo-Tolstoy/dp/0143035002
• Playing and Reality: https://www.amazon.com/Playing-Reality-Routledge-Classics-86/dp/0415345464
• The Death of Ivan Ilyich: https://www.amazon.com/Death-Ivan-Ilyich-Leo-Tolstoy/dp/1468014315
• A Swim in a Pond in the Rain: https://www.amazon.com/Swim-Pond-Rain-Russians-Writing/dp/1984856022
• The Master and His Emissary: The Divided Brain and the Making of the Western World: https://www.amazon.com/Master-His-Emissary-Divided-Western/dp/0300245920/
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
Lenny may be an investor in the companies discussed.
To hear more, visit www.lennysnewsletter.com
Using ChatGPT As a Copilot For Your Mind
In this video, Nathan chats to Dan Shipper, CEO and Co-founder of Every, for the series "How I Use Chat-GPT". They discuss Nathan's prompting techniques for creative and cognitive labour, and using GPT in copilot instead of delegation mode. If you need an ecommerce platform, check out our sponsor Shopify: https://shopify.com/cognitive for a $1/month trial period.
Watch the rest of the series, "How I Use ChatGPT", here: https://www.youtube.com/@EveryInc
We're hiring across the board at Turpentine and for Erik's personal team on other projects he's incubating. He's hiring a Chief of Staff, EA, Head of Special Projects, Investment Associate, and more. For a list of JDs, check out: eriktorenberg.com.
SPONSORS:
Shopify is the global commerce platform that helps you sell at every stage of your business. Shopify powers 10% of ALL eCommerce in the US. And Shopify's the global force behind Allbirds, Rothy's, and Brooklinen, and 1,000,000s of other entrepreneurs across 175 countries.From their all-in-one e-commerce platform, to their in-person POS system – wherever and whatever you're selling, Shopify's got you covered. With free Shopify Magic, sell more with less effort by whipping up captivating content that converts – from blog posts to product descriptions using AI. Sign up for $1/month trial period: https://shopify.com/cognitive
Omneky is an omnichannel creative generation platform that lets you launch hundreds of thousands of ad iterations that actually work customized across all platforms, with a click of a button. Omneky combines generative AI and real-time advertising data. Mention "Cog Rev" for 10% off.
NetSuite has 25 years of providing financial software for all your business needs. More than 36,000 businesses have already upgraded to NetSuite by Oracle, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅ head to NetSuite: http://netsuite.com/cognitive and download your own customized KPI checklist.
X/SOCIAL:
@labenz (Nathan)
@danshipper (Dan)
@CogRev_Podcast (Cognitive Revolution)
@Every (Every)
TIMESTAMPS:
(00:00) - Episode Preview
(00:03:57) - Copilot vs delegation mode
(00:11:06) - ChatGPT for coding
(00:14:29) - Building a prompt coach
(00:28:22) - Best practices for using Chat-GPT
(00:43:55) - The “dance” between you and AI
(00:50:16) - Using GPT as a thought partner
(00:52:07) - Using GPT for diagrams
(01:03:18) - Using Perplexity instead of a search engine
(01:12:00) - What's ahead for AI
This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co.
The unexpected key to boosting your productivity | Dan Shipper
Ever wished you could stop procrastinating and just be as efficient as a machine? Since you're a human, that's not going to happen -- but that's OK, says entrepreneur Dan Shipper. Here's how you can use awareness, observation and experimentation to clear your own way to getting more done.
Hosted on Acast. See acast.com/privacy for more information.
(TWTR SPC) Every.to And Mac Studio
We talked to Nathan Baschez and Dan Shipper, the founders of the media startup Every.to. We talked to them about the realities of being two years in as a modern, from the ground up media company, the shifting landscape in the “creator economy” (remember that?) And a lot about Substack and its business model and philosophy. Around the hour mark, Chris and I have a lengthy conversation about the Mac Studio, my purchasing of one, my cancelling of my order for a Studio Display. And also, Chris has a very interesting 8 dimensional chess theory about where Apple is headed as a company.
Learn more about your ad choices. Visit megaphone.fm/adchoices
#219 – How to Make Your Business Model a Win-Win-Win - with Dan Shipper and Nathan Baschez of Every
My guests today have a really exciting business model and strategy that I want to dig into. Dan Shipper (@danshipper) and Nathan Baschez (@nbashaw) are the founders of Every, a bundle of business focused newsletters. By structuring Every as a "collective," the writers are happier, the readers are getting better content, and Every is profitable. I want to find out how they get readers, how they get writers, and how "bundling" can be strategic for indie hackers.
Subscribe to Every: https://every.to/
Follow Nathan on Twitter: https://twitter.com/nbashaw
Follow Dan on Twitter: https://twitter.com/danshipper