Entrepreneur Andrew Wilkinson used to sleep nine hours a night. Now he wakes up at 4 a.m. and goes straight to work—because he can’t wait to keep building with Anthropic’s latest model, Opus 4.5.

Two years ago, Wilkinson was obsessed with vibe coding on AI software development platform Replit. It was thrilling to describe something in plain English and watch an app appear, less thrilling when the apps were always broken in some way, often full of maddening bugs. So he set his app creation ambitions aside until technology caught up with them.

Then, a few weeks ago, he started playing with Claude Code and Opus 4.5. It felt, he says, like having a “$100,000-a-month payroll of engineers” working for him around the clock.

Wilkinson is the cofounder of Tiny, a company that buys profitable businesses and holds them for the long term. The Tiny portfolio includes the AeroPress coffee maker and Dribbble, a platform where designers can share their work and find jobs. Dan Shipper had him on AI & I to talk about the automations Wilkinson has built for his work and personal life, including an AI relationship counselor, a custom email client, and a system that texts him outfit recommendations each morning. Wilkinson revealed how all of this individual exploration has changed the way he thinks about buying software companies at Tiny.

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

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To hear more from Dan Shipper:

Subscribe to Every: https://every.to/subscribe

Follow him on X: https://twitter.com/danshipper

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

00:01:07 - Introduction

00:02:48 - Why Opus 4.5 feels like the iPhone moment for vibe coding

00:08:31 - Why designers have a unique advantage with AI

00:14:10 - How Wilkinson built a custom email client with Claude Code

00:18:13 - An AI trained on your relationship that predicts your fights

00:30:40 - Using AI meeting notes to make your life better

00:35:11 - Don't inject your opinion into prompts

00:40:21 - Wilkinson’s Claude Code tips and workflows

00:47:59 - Your personal stylist is a prompt away

00:53:17 - How AI is changing the way Wilkinson invests in software

Links to resources mentioned in the episode:

Andrew Wilkinson: Andrew Wilkinson (@awilkinson)

The book Wilkinson references in his prompts, when writing copy with AI: Made to Stick

Every’s compound engineering plugin: https://github.com/EveryInc/compound-engineering-plugi

LLMs have made it absurdly easy to go deep on almost any topic. So why haven’t we all used ChatGPT to earn college degrees we wished we had majored in or pursued a niche interest, like learning how to name the trees in our neighborhood? I know I’m not the only one to feel guilty for well-intentioned attempts at autodidactism that inevitably peter out.

Entrepreneur Nir Zicherman has a reason for this disconnect: LLMs can answer most of your questions, but they won’t notice when you’re lost or pull you back in when your motivation starts to fade.

As the CEO and cofounder of Oboe, a platform that generates personalized courses about everything from the history of snowboarding to JavaScript fundamentals using AI, Zicherman has thought deeply about why the ability to access information does not automatically lead to understanding a concept. In this episode of AI & I, he talks to Dan Shipper about everything he’s learned about learning with LLMs.

They get into Zicherman’s counterintuitive belief that learning is a more passive process than you’d think, the biggest blocker for most people who want to learn something new, and where AI agents currently fall short in providing a meaningful learning experience.

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

00:00:36 - Introduction

00:01:49 - Why you need a dedicated AI learning app

00:04:32 - The process of learning is more passive than you might think

00:10:21 - Live demo of Oboe to create a course about philosopher Ludwig Wittgenstein

00:16:52 - Learning works best when it comes in many formats

00:28:21 - Where AI agents currently fall short in the learning experience

00:34:10 - The importance of making learning feel accessible

00:35:56 - How Zicherman uses Oboe to learn quantum physics

00:40:54 - How embeddings spaces remind Dan of quantum mechanics

Links to resources mentioned in the episode:

Nir Zicherman: @NirZicherman

Learn something new with Oboe: https://oboe.com/

Anthropic just dropped Claude Cowork—essentially Claude Code for everyone, not just engineers—and we got to chat about it with a product engineer at Anthropic who helped build it.

In this live Vibe Check, Dan Shipper and Kieran Klaassen explore the new interface together, testing what works (and what doesn't) in real time. Anthropic’s Felix Rieseberg joins midway through to explain the philosophy behind Cowork's design: why it separates "Tasks" from "Chats," how the queue system lets you send messages while the agent is working, and what "agent-native" architecture means in practice. They also dig into Skills—Claude's prompt system that lets you customize how it works—and the Chrome connector for browser automation.

This is a raw, unfiltered first look at what might be the future of how knowledge workers interact with AI: async workflows instead of turn-by-turn chat.

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

Want even more?

Check out Dan's guide to building agent-native applications: https://every.to/guides/agent-native

To hear more from Dan Shipper:

Subscribe to Every: https://every.to/subscribe

Follow him on X: https://twitter.com/danshipper

00:01:00 - What is Claude Cowork

00:02:36 - First demo: competitor analysis

00:03:33 - Email drafting that sounds like me

00:06:18 - Calendar audit running for an hour

00:07:39 - Book taxonomy demo

00:08:42 - PostHog analytics via Chrome browsing

00:14:36 - Chat vs Code vs Cowork: when to use what

00:31:06 - Felix from Anthropic joins

00:36:39 - Why they built it in a week and a half

00:37:57 - Design decision: why a separate tab

00:43:57 - Skills as the primary hackable surface

00:49:36 - Agent-native architecture principles

00:56:57 - The origin story of skills at Anthropic

01:03:00 - Our final rating

From cofounding LinkedIn to backing OpenAI early, Reid Hoffman is in the habit of being right about the future, so we wanted to know what he saw coming in 2026.

In his third appearance on AI & I, Hoffman lays out his predictions for where AI will go in the 12 months ahead. He talks to Dan Shipper about how agents will break out of coding into other domains and who’s winning the coding agent race. They also get into how Hoffman defines artificial general intelligence, the way he believes enterprises will use AI, and why public debate on AI might turn more negative, even as the technology becomes more empowering for individuals.

Hoffman’s other bets on the future include cofounding AI drug discovery startup Manas AI, investing at venture capital firm Greylock Partners, writing books, and hosting the Masters of Scale podcast. He’s also an investor 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:

• Subscribe to Every: https://every.to/subscribe

• Follow him on X: https://twitter.com/danshipper

Timestamps:

00:00:00 - Start

00:00:52 - Introduction

00:02:20 - The future of work is an entrepreneurial mindset

00:05:22 - Creation is addictive (and that’s okay)

00:09:22 - Why discourse around AI might get uglier this year

00:17:03 - AI agents will break out of coding in 2026

00:24:18 - What makes Anthropic’s Opus 4.5 such a good model

00:28:46 - Who will win the agentic coding race

00:36:13 - Why enterprise AI will finally land this year

00:43:16 - How Hoffman defines AGI

00:55:33 - The most underrated category to watch in AI right now

Links to resources mentioned in the episode:

• Reid Hoffman: Reid Hoffman (@reidhoffman)

The AI drug discovery startup Hoffman cofounded: Manas AI

Tomorrow is the first day of 2026, and to give our listeners a view of the trends that’ll shape the year ahead, Dan Shipper had Every COO Brandon Gell on AI & I to discuss their predictions for what’s next. They discussed how software will be built, who will build it, and what it will take for truly autonomous AI agents to become a reality.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 — Start00:01:05 — Introduction00:01:34 — Reflections on Every’s growth over the past year00:09:38 — What changes when a company grows from 20 to 50 people00:11:55 — How agent-native architecture will change software in 202600:17:13 — Why designers are slated to become power users of AI00:23:24 — The new kind of software engineer who will direct AI agents00:33:42 — Why the next wave of AI training will focus on autonomy

Learn how to use philosophy to run your business more effectively.

Reid Hoffman thinks a masters in philosophy will help you run your business better than an MBA. Reid is a founder, investor, podcaster, and author. But before he did any of these things, he studied philosophy—and it changed the way he thinks. Studying philosophy trains you to think deeply about truth, human nature, and the meaning of life. It helps you see the big picture and reason through complex problems—invaluable skills for founders grappling with existential questions about their business.

I usually bring guests onto my podcast to discuss the actionable ways in which people have incorporated ChatGPT into their lives. But this episode is different. I sat down with Reid to tackle a deeper question: How is AI changing what it means to be human?

It was honestly one of the most meaningful shows I’ve recorded yet. We dive into:

- How philosophy prepares you to be a better founder

- The importance of interdisciplinary thinking

- Essentialism v. nominalism in the context of AI

- How language models are evolving to be more “essentialist”

- The co-evolution of humans and technology

Reid also shares actionable uses of ChatGPT for people who want to think more clearly, like:

- Input your argument and ask ChatGPT for alternative perspectives

- Generate custom explanations of complex ideas

- Leverage ChatGPT as an on-demand research assistant

This episode is a must-watch for anyone curious about some of the bigger questions prompted by the rapid development of AI.

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

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

00:04:35 - Why philosophy will make you a better founder

00:08:22 - The fundamental problem with “trolley problems”

00:14:27 - How AI is changing the essentialism v. nominalism debate

00:29:33 - Why embeddings align with nominalism

00:34:26 - How LLMs are being trained to reason better

00:44:52 - How technology changes the way we see ourselves and the world around us

00:46:24 - Why most psychology literature is wrong

00:52:46 - Why philosophers didn’t come up with AI

00:56:30 - How to use ChatGPT to be more philosophically inclined

Links to resources mentioned in the episode:

Reid Hoffman: https://twitter.com/reidhoffman

The podcasts that Reid hosts: Possible (possible.fm) and Masters of Scale (https://mastersofscale.com/)

Reid’s book: Impromptu https://www.impromptubook.com/

The book Reid recommends if you want to be more philosophically inclined: Gödel, Escher, Bach https://www.amazon.com/G%C3%B6del-Escher-Bach-Eternal-Golden/dp/0465026567

Reid’s article in the Atlantic: "Technology Makes Us More Human" https://www.theatlantic.com/ideas/archive/2023/01/chatgpt-ai-technology-techo-humanism-reid-hoffman/672872/

The book about why psychology literature is wrong: The WEIRDest People in the World by Joseph Henrich https://www.amazon.com/WEIRDest-People-World-Psychologically-Particularly/dp/0374173222

The book about how culture is driving human evolution: The Secrets of Our Success by Joseph Henrich https://press.princeton.edu/books/paperback/9780691178431/the-secret-of-our-success

We recorded someone guide himself into a Jhana live on our podcast. And he narrated the whole process from start to finish.

Jhanas are meditative bliss states and they traditionally require thousands of hours of practice. But Stephen Zerfas and his team at Jhourney are changing that—creating retreats where most participants hit a Jhana in their first week.

Dan Shipper went to one of their retreats earlier this year, and it was by far the best he’s been to. So we had Stephen on AI & I to show us how he gets into a Jhana and what the future of super wellbeing might look like.

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:

Introduction: 00:00:56

A primer on Jhana meditation: 00:01:18

Zerfas guides himself into a Jhana: 00:05:47

Why Jhana is about resting into what already exists: 00:36:04

Approaching meditation with play and curiosity: 00:39:30

The potential pitfalls of Jhana meditation: 00:45:04

How to hack your personality through memory reconsolidation: 00:48:21

Why Jhana won't let you numb yourself to real problems: 00:53:10

How Jhana meditation has changed Zerfas: 00:55:36

How Jhourney is using AI to make Jhanas more accessible: 01:09:41

Links to resources mentioned in the episode:

• Stephen Zerfas: Stephen Zerfas
• Jhourney: https://www.jhourney.io/
• The Donella Meadows book Zerfas refers to: Thinking in Systems: A Primer

Sarah Rose Siskind is incubating two types of intelligence at once: her unborn child, and FetusGPT—an LLM trained on nothing but what she hears and says throughout the day.

This includes Seinfeld episodes, YouTube videos about lemurs, eight hours of snoring per night—and even conversations with me, all condensed into MP3 and text files that are used to train the AI. Since FetusGPT is learning English from such a narrow, idiosyncratic slice of the world, it mostly babbles right now, and if she swears, it picks that up too.

FetusGPT is one zany example of how Siskind uses humor to make a bigger point: AI is what we make of it. It’s an approach that feeds through her comedy writing and work as the founder of science and technology communications agency Hello SciCom.

We had Siskind on AI & I to talk about how she uses AI in her creative process as a comedian, and the unexpected support it's become, both practical and emotional, as she navigates pregnancy.

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
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:

00:00:00 - Start

00:01:54 - Introduction

00:02:03 - How Siskind is running an experiment between her unborn child and an LLM

00:07:34 - A demo of Siskind’s FetusGPT

00:15:16 - Siskind’s pick for the funniest LLM

00:17:12 - How Siskind uses AI in her comedy writing

00:24:41 - Dan and Siskind use ChatGPT to write a joke together live on the show

00:37:21 - Why AI is useful even when you don’t use its output directly

00:44:15 - How Siskind used a ChatGPT project to biohack her energy levels

00:57:09 - A question we fundamentally couldn’t have asked in pre-ChatGPT times

01:05:29 - How ChatGPT is a source of emotional support for Siskind in pregnancy

Links to resources mentioned in the episode:

Sarah Rose Siskind: https://sarahrosesiskind.com/

Siskind’s agency HelloSciCom: https://www.hellosci.com/

Siskind’s book recommendations: I Forced a Bot to Write This Book, The Let Them Theory, Artificial Intelligence: An Illustrated History

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/subscribe
• Follow 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 Ford
• Ford’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

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.

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