AI & I
AI & I

AI & I

Dan Shipper

Overview
Episodes

Details

Learn how the smartest people in the world are using AI to think, create, and relate. Each week I interview founders, filmmakers, writers, investors, and others about how they use AI tools like ChatGPT, Claude, and Midjourney in their work and in their lives. We screen-share through their historical chats and then experiment with AI live on the show. Join us to discover how AI is changing how we think about our world—and ourselves. For more essays, interviews, and experiments at the forefront of AI: https://every.to/chain-of-thought?sort=newest.

Recent Episodes

Why Opus 4.5 Just Became the Most Influential AI Model
DEC 3, 2025
Why Opus 4.5 Just Became the Most Influential AI Model

The world changed last week—Opus 4.5 is the best coding model Dan has ever used.
It can keep coding and coding autonomously without tripping over itself—and it marks a completely new horizon for the craft of programming. The dream is here: You can write English, and make software.
We had Paul Ford on AI & I to talk about it. Ford is the co-founder of Aboard and also a prolific writer. He authored one of Dan’s favorite pieces of technology writing What Is Code?—so he’s the perfect person to unpack this with him.
We talk about the wonder—and genuine unease—that comes with using tools this powerful. We also get into what people who love technology should care about as the ground under us shifts faster than we can imagine.
If you found this episode interesting, please like, subscribe, comment, and share!


Want even more?
Sign up for Every to unlock our ultimate guide to prompting ChatGPT here: ⁠https://every.ck.page/ultimate-guide-to-prompting-chatgpt⁠. It’s usually only for paying subscribers, but you can get it here for free.


To hear more from Dan Shipper:
Subscribe to Every: ⁠https://every.to/subscribe⁠Follow him on X: ⁠https://twitter.com/danshipper⁠


Head to ⁠ai.studio/build⁠ to create your first app
Ready to build a site that looks hand-coded—without hiring a developer? Launch your site for free at ⁠Framer.com⁠, and use code DAN to get your first month of Pro on the house!


Timestamps:
00:00:00 - Start
00:01:57 - Introduction
00:03:28 - How Claude Opus 4.5 made the future feel abruptly close
00:08:12 - The design principles that make Claude Code a powerful coding tool
00:10:57 - How Ford uses Claude Code to build real software
00:20:12 - Why collapsing job titles and roles can feel overwhelming
00:22:56 - Ford’s take on using LLMs to write
00:24:09 - A metaphor for weathering existential moments of change
00:25:45 - What GLP-1s taught Ford about how people adapt to big shifts
00:49:36 - Why you should care what your LLM was trained on
00:52:15 - Ford prompts Claude Code to forecast the future of the consulting industry
00:59:18 - Recognize when an LLM is reflecting your assumptions back to you
01:12:39 - How large enterprises might adopt AI


Links to resources mentioned in the episode:
Paul Ford: ⁠Paul Ford⁠Ford’s company Aboard: ⁠https://aboard.com/⁠The piece Ford wrote for Bloomberg in 2015: ⁠What Is Code?⁠Alan Kay’s concept of a personal computer for children: ⁠https://en.wikipedia.org/wiki/Dynabook⁠

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85 MIN
Best of the Pod: Would You Shut Down Your Most Successful Product? The Arc to Dia Story
NOV 26, 2025
Best of the Pod: Would You Shut Down Your Most Successful Product? The Arc to Dia Story

If you had millions of people using a product you spent years building, would you kill it?

That’s exactly what The Browser Company did with Arc.

Originally recorded in July before The Browser Company’s acquisition by software giant Atlassian earlier this year, we’re republishing this episode because its lessons are truly timeless. Today, the team continues to operate independently under Atlassian’s umbrella.

The internet backlash when the company killed Arc in May 2025 was intense, but cofounders Josh Miller and Hursh Agrawal saw that AI was about to make the web something you talk to, not just click into. The best home for that assistant was the thing that's already between you and the internet—the browser. And they realized they couldn’t just duct-tape it on to Arc.

One year of heads-down work later, the team launched Dia in beta, and people are raving about it. Dia is a sleek, fast, browser with AI at its core—it gets better with every tab you open, becoming more and more helpful with time.

And even though it’s still early, Josh and Hursh’s big pivot looks like one for the ages.

In this episode of AI & I, Josh and Hursh spoke for the first time in a full-length podcast about their pivot from Arc to Dia. We talked through their decision-making process, the very public backlash the company faced, and the grit it took to stay the course.

If you found this episode interesting, please like, subscribe, comment, and share!

Want even more?
Sign up for Every to unlock our ultimate guide to prompting ChatGPT here: https://every.ck.page/ultimate-guide-to-prompting-chatgpt. It’s usually only for paying subscribers, but you can get it here for free.

To hear more from Dan Shipper:
Subscribe to Every: https://every.to/subscribe
Follow him on X: https://twitter.com/danshipper


Timestamps:
00:00:00 - Start
00:00:48 - Introduction
00:02:22 - The story of how Dan might've been the CEO of The Browser Company
00:09:40 - The moment Josh and Hursh knew they had to walk away from Arc
00:16:59 - How to handle the weight of the unknown in a pivot
00:23:24 - The prototype-driven culture that kept The Browser Company alive
00:25:06 - Why having a product loved by millions of users isn't enough
00:32:12 - The architectural decisions underlying how Dia was built
00:46:04 - How Dia almost shipped without its best feature
00:50:45 - The best ways people are using Dia in the wild
01:07:27 - How Josh and Hursh think about competing with incumbents
01:17:13 - How romanticism informs the product decisions behind Dia

Links to resources mentioned in the episode:
Hursh Agrawal: @hursh
Josh Miller: @joshm
More about Dia: https://www.diabrowser.com/
Writer and investor M.G. Siegler’s essay about the AI browser wars: https://spyglass.org/ai-browser-wars/

Note: This episode is a rerun from our archives.

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83 MIN
 Best of the Pod: Claude Code - How Two Engineers Ship Like a Team of 15
NOV 19, 2025
Best of the Pod: Claude Code - How Two Engineers Ship Like a Team of 15

If you’re using AI to just write code, you’re missing out.

Two engineers at Every shipped six features, five bug fixes, and three infrastructure updates in one week—and they did it by designing workflows with AI agents, where each task makes the next one easier, faster, and more reliable.

In this episode of AI & I, Dan Shipper interviewed the pair—Kieran Klaassen, general manager of Cora, our inbox management tool, and Cora engineer Nityesh Agarwal—about how they’re compounding their engineering with AI. They walk Dan through their workflow in Anthropic’s agentic coding tool, Claude Code, and the mental models they’ve developed for making AI agents truly useful. Kieran, our resident AI-agent aficionado, also ranked all the AI coding assistants he’s used.

If you found this episode interesting, please like, subscribe, comment, and share!

Want even more?
Sign up for Every to unlock our ultimate guide to prompting ChatGPT here: https://every.ck.page/ultimate-guide-to-prompting-chatgpt. It’s usually only for paying subscribers, but you can get it here for free.

To hear more from Dan Shipper:
Subscribe to Every: https://every.to/subscribe
Follow him on X: https://twitter.com/danshipper
Head to ai.studio/build to create your first app.

Pitch is the AI presentation platform that helps professionals collaborate on, create, and deliver winning slide decks — all while staying on brand: https://pitch.com/use-cases/ai-presentation-maker/?utm_medium=paid-influencer&utm_campaign=every 

Timestamps:
Episode start: 00:00:00
Introduction: 00:01:16
Why Kieran believes agents are turning a corner: 00:03:18
Why Claude Code stands out from other agents: 00:06:36
What makes agentic coding different from using tools like Cursor: 00:11:58
The Cora team’s workflow to turn tasks into momentum: 00:15:20
How to build a prompt that turns ideas into plans: 00:23:07
The new mental models for this age of software engineering: 00:34:00
Why traditional tests and evals still matter: 00:39:13
Kieran ranks all the AI coding agents he’s used: 00:42:00

Links to resources mentioned in the episode:
Try Cora, our AI email assistant: https://cora.computer/

Kieran Klaassen: @kieranklaassen
Nityesh Agarwal: @nityeshaga
The book that helps Nityesh form mental models to work with AI agents: High Output Management

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53 MIN
Building AI Agents to Launch a Million Businesses
NOV 12, 2025
Building AI Agents to Launch a Million Businesses

Henrik Werdelin wants to launch a million businesses that each make $1M—and he’s doing it with AI.

After helping launch Barkbox and Ro Health through his incubator Prehype, Henrik is distilling everything he knows into Audos, a platform that helps you use AI agents to turn your idea into a profitable, lasting company.


We had him on AI & I to talk about “portfolio entrepreneurship”—a new breed of entrepreneurship shepherded in by AI, where founders build families of products around the same customer, instead of one moonshot idea. It’s a philosophy we hold close to our hearts at Every.

If you found this episode interesting, please like, subscribe, comment, and share!


Want even more?

Sign up for Every to unlock our ultimate guide to prompting ChatGPT here: https://every.ck.page/ultimate-guide-to-prompting-chatgpt. It’s usually only for paying subscribers, but you can get it here for free.

To hear more from Dan Shipper:

Head to ai.studio/build to create your first app.


Ready to build a site that looks hand-coded—without hiring a developer? Launch your site for free at
https://www.framer.com/, and use code DAN to get your first month of Pro on the house!


Pitch is the AI presentation platform that helps professionals collaborate on, create, and deliver winning slide decks — all while staying on brand:
https://pitch.com/use-cases/ai-presentation-maker/?utm_medium=paid-influencer&utm_campaign=every !

Timestamps:

00:01:33 - Introduction

00:02:50 - Dan and Henrik on the new breed of entrepreneurship that AI makes possible

00:11:08 - Why Henrik believes the future belongs to a million $1M companies

00:16:14 - How to build “relationship capital” with your customers

00:21:35 - Why “customer-founder fit” shapes lasting companies

00:23:01 - Everything Henrik learned about himself from a decade of building companies

00:31:44 - How Henrik finds focus and meaning in the daily chaos

00:34:17 - How Henrik is parenting two kids in the age of AI

00:50:33 - The way AI can fix what social media broke

00:56:59 - What happens when AI agents become part of how we tell stories


Links to resources mentioned in the episode:

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65 MIN
What Jason Fried Learned from 26 Years of Building Great Products
NOV 5, 2025
What Jason Fried Learned from 26 Years of Building Great Products

37signals makes tens of millions in profit every year but ⁠Jason Fried⁠ isn’t all that interested in running a business.

Instead, he cares most about making great products—like ⁠Basecamp⁠, ⁠HEY⁠, and ⁠Ruby on Rails⁠—products that are centered around a single, coherent idea. These products are complete wholes, where each piece matters—like a Frank Lloyd Wright house or a vintage car.

But how do you create products like that?

In this conversation, we talk to Jason about what two decades of building 37signals has been like—and how to build products that have soul.

If you found this episode interesting, please like, subscribe, comment, and share!


Want even more?

Sign up for Every to unlock our ultimate guide to prompting ChatGPT here: ⁠https://every.ck.page/ultimate-guide-to-prompting-chatgpt⁠. It’s usually only for paying subscribers, but you can get it here for free.

To hear more from Dan Shipper:

Listen to Working Smarter wherever you get your podcasts, or visit ⁠workingsmarter.ai⁠

Timestamps:

00:00:00 - Start

00:00:32 - Introduction

00:02:06 - What architecture, watches, and cars teach us about software

00:10:54 - How Jason thinks AI plays into product-building

00:20:58 - How developers at 37signals use AI

00:25:47 - Jason’s biggest realization after 26 years of running 37signals

00:29:58 - Where Jason thinks luck shaped his career

00:32:41 - What Jason would do if he were graduated into the AI boom

00:37:22 - Dan asks for advice on running a non-traditional company like Every

00:46:39 - Why staying true to yourself is the only way to build something lasting

00:49:38 - Wholeness as the north star for building products—and companies


Links to resources mentioned in the episode:

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58 MIN