AI & I

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.
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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-plugin

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.

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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.
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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 — Start
00:01:05 — Introduction
00:01:34 — Reflections on Every’s growth over the past year
00:09:38 — What changes when a company grows from 20 to 50 people
00:11:55 — How agent-native architecture will change software in 2026
00:17:13 — Why designers are slated to become power users of AI
00:23:24 — The new kind of software engineer who will direct AI agents
00:33:42 — Why the next wave of AI training will focus on autonomy