Lenny's Newsletter

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Listen: A visual guide to getting out of a creative slump

Lenny Rachitsky — Wed, 08 Apr 2026 02:51:13 GMT

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In this episode, my wife Michelle Rial, cartoonist and author, celebrates the launch of her new book Charts for Babies by sharing a pep talk for anyone stuck in a creative rut. She walks through 12 tried-and-tested steps designed to lift you out of a creative block and get back to making things that matter.

Listen now: YouTube | Apple | Spotify

In this episode, you’ll learn:

Why it’s necessary to create work that might feel embarrassing
The simple mindset shift that stops stalling and gets you to just start
How to reframe scorn as a positive signal
The thought process that can help you move out of a state of rumination
How to treat failed ideas as seeds for future breakthroughs

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A visual guide to getting out of a creative slump

Michelle Rial — Tue, 07 Apr 2026 12:45:49 GMT

👋 Hey there, I’m Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast | Lennybot | How I AI | My favorite AI/PM courses, public speaking course, and interview prep copilot

I’m so, so excited to share a guest post by Michelle Rial, my wife! Her first children’s book, Charts for Babies, comes out TODAY, and we thought: what better way to celebrate than collaborating on a post? Below, you get a glimpse into her brilliant mind. This visual guide is both inspiring and useful, and is for anyone trying to create something. Read it right now or bookmark it for the next time you get stuck.

P.S. Michelle’s book is truly great, and makes an excellent gift—but you don’t have to just take my word for it. Renowned child psychologist and parenting coach Dr. Becky said, “Charts for Babies says to your child, ‘I believe you can understand the world’—and that message matters from the very start.” And Booklist said, “Rial’s understanding of her audience and her ability to distill information clearly are gifts, and the whimsical hand-drawn illustrations and text will delight readers.” Grab a copy (or two) here.

Are you feeling what I’m feeling? Blink twice with your heavy human eyelids if you are starting to feel like there is no point to creating things anymore. That if robots can do the creative work we spend hours, days, months, or years pulling our hair out over, why should we even try?

Or maybe you’re just in a regular creative drought. The paralysis of worrying that your work isn’t worth doing anymore or that someone (or something) is already doing it better.

Well, it’s time to lift yourself by your Blundstone loops and climb right out of that rut. I’ve made you a visual pep talk.

Each of the following 12 charts I’m about to share was crafted from the inside of one of these hollows. Making them felt like peeking out from underwater before heaving myself out of the sea like a slippery, blubbery walrus, gripping the land and steadying myself with my number 2 pencil-tusks.

I hope that this guide will help you, too. Maybe you’ll be able to hoist your heavy artist soul out of the deep dark ocean, onto a sunny platform where we can all warm our insides together and enjoy some ceviche.

And if any robots are listening, please get back to work on helping me find the cause of my eczema.

1. Be OK with being embarrassing

As a sensitive human, putting work out into the world to be judged can feel excruciating. What if I look “thirsty”? Or worse, what if Gen Z thinks I’m cringe? What if, what if, what IF? It makes me want to pack up my infinity notebooks and quit.

But the people who always end up with something really good? They don’t stop. Maybe they pause or take a rest, but they always come back and keep going. Nobody remembers the project that didn’t get any traction, the one that may have seemed a bit embarrassing at the time. People remember the successes and forget all the attempts.

2. Ignore the algorithm

Are you making work to please the algorithm like it’s your never-satisfied immigrant parent? (Just me?) Well, the algorithm will change, and then you’ll look back and be like: what the hell was that? So instead, try to make things that make YOU laugh, make you tear up, make you spit out your iced matcha latte that is apparently causing your anemia.

3. Use your caffeine wisely

Caffeine can be amazing for creativity . . . until it isn’t. Try not to fall into the trap of squandering your mental alertness on a pile of emails that only needed a simple “sounds good!” What happens then is we don’t make any progress on the juicy stuff, we feel defeated, and we reach for another cup. And then . . .

4. Overwhelmed? Take some breaths.

You might think it’s too early in this process to be overwhelmed, but sometimes staring at a blank page (or at a very full page that you just realized is trash) can feel incredibly overwhelming. And the overwhelm paralyzes you before you can even get going. Especially if you just flew past your caffeine limit.

I highly recommend having a meditation or breathwork practice. The times I’ve been consistent with it have been my most steady and productive times. Unfortunately, today I’m right here with you, panicking that I need to finish this post.

5. Stop thinking about what you’re going to work on and just get started

Yes, your ergonomics should be solid; yes, you need to find quiet or a playlist that helps you focus. But after that, stop stalling and just get started. If you get distracted, start again. Butt in chair.

6. Keep going

And going, and going, and going. The love of the work is the reason you got into this in the first place. Remember that the work is the point, and the struggle is what makes your story interesting. Imagine succeeding at every attempt—you’d need a whole forearm full of mal de ojo bracelets.

7. You can’t control how the work will be perceived

Sure, you can throw your best effort into sharing and promoting your thing. Some people will hate it. Some people hate you and thus hate it. If people hate it, congrats, it’s popular enough to attract scorn. Maybe nobody sees it? Congrats, it’s a hidden gem. Be proud of what you’ve done, share as best you can and as often as you can stomach, and then keep on making and progressing.

8. Rumination is a waste of time

Something I know about the writer of this newsletter is he doesn’t ruminate or get caught up in regret, which may be how he is so mind-blowingly productive. His thought loops? They move forward in a straight line. The only time he looks back is to note how he can do something better in the future. I might try that.

9. Each failed idea creates the potential for new growth

Don’t discount ideas just because they didn’t work right away. Let them grow and sprout in new directions. Put them in your bad-idea pile and let that pile grow and grow until your dining table is covered in bad ideas and you have only a tiny sliver of your table to actually eat on. Come back to those ideas, and see what blossoms into something new and what’s still a goner.

And then clean your dining table, for the love of god!! People LIVE HERE.

10. You’re already further along than you think

If you’re blocked and feeling like you’ve been at something forever and still have nothing, go back and look at your draft pile. I bet you’ll spot some progress.

11. It’s never too late to start

Be the adult leaving your piano lesson as a first grader is arriving. Be the youngest person at your rec center’s water aerobics class. It’s never too late (or too early). You might discover you’re great at something you didn’t know about. Or even better, you might have a blast. The juicy new neural pathways in your brain will thank you.

12. Still feeling it all? “Let it be.”

Did you enjoy this in any small, tiny, pie-chart fraction of a way?

If so, please check out my new children’s book, Charts for Babies! It is OUT TODAY and available wherever you buy your books (it’s also at places like MoMA Design Store and SFMOMA Museum Store!).

It’s my way of introducing the language of math at a very early age, when the brain is at its spongiest.

You can request it from your local library or bookstore, gift it to a new parent (unless they sternly specified NO GIFTS), or get it for the future mathlete in your life!

Thanks, Michelle! Have a fulfilling and productive week 🙏

If you’re finding this newsletter valuable, share it with a friend, and consider subscribing if you haven’t already. There are group discounts, gift options, and referral bonuses available.

Sincerely,

Lenny 👋

🎙️ This week on How I AI: I gave Claude Code our entire codebase. Our customers noticed.

Lenny Rachitsky — Mon, 06 Apr 2026 15:03:07 GMT

I gave Claude Code our entire codebase. Our customers noticed. | Al Chen (Galileo)

Listen now on YouTube • Spotify • Apple Podcasts

Brought to you by:
Orkes—The enterprise platform for reliable applications and agentic workflows
Tines—Start building intelligent workflows today

Al Chen is a field engineer at Galileo who works directly with enterprise customers asking highly technical questions. In this episode, Claire talks with Al about how he uses Claude Code to query Galileo’s entire codebase across 15 repositories, combine it with Confluence and Slack, and deliver accurate, real-time answers without relying on documentation or constantly pinging engineering. They cover why code is often a better source of truth than docs, how to turn customer questions into scalable knowledge, and how AI is changing what customer-facing teams can do.

Biggest takeaways:

Write a script to pull the latest code from all repos daily—and let Claude Code write it. Al uses a 16-line script (written entirely by Claude Code) that pulls the latest main branch from all 15 repositories every morning. This ensures that he’s always querying current code instead of outdated information, solving the “docs are stale” problem that plagues most technical support teams.
Maintain a “customer quirks” page to make AI answers customer-specific. Al keeps a Confluence page listing each enterprise customer’s unique deployment requirements: how they handle secrets, namespaces, encryption, air-gapped environments. His Claude Code custom commands reference this page first, generating highly tailored deployment instructions instead of generic answers anyone could Google.
Combine code repositories with Confluence MCP for maximum context. Al’s custom Claude Code commands first check Confluence for deployment documentation, then query the code repositories if needed. This multi-source approach means Claude Code pulls from official docs, tribal knowledge, and actual implementation—delivering answers no single source could provide.
Your code is better documentation than your docs. Al realized public documentation couldn’t answer his enterprise customers’ detailed technical questions. By pulling all 15 of Galileo’s repositories into VS Code and querying them with Claude Code, he can now answer questions about how services cascade together, how features actually work, and deployment specifics that aren’t captured anywhere else.
Turn Slack support threads into knowledge base articles automatically. Using Pylon, Al converts detailed customer conversations into abstracted help articles with one click. These articles are more in-depth and current than official docs because they’re based on real customer questions and don’t require the overhead of PR reviews and approval processes.
Reduce engineering interruptions to near-zero by self-serving answers. Before this system, Al constantly pinged engineering with customer questions, creating frustration on both sides. Now he queries the code directly, only reaching out to validate answers or when Claude Code can’t find information (usually because it exists only in meeting notes or hallway conversations).
The human value-add is making AI answers sound human, and knowing when to validate. Al doesn’t blindly copy-paste Claude Code responses. He proofreads everything, removes telltale AI phrases like “in summary,” condenses verbose answers to what customers actually need, and validates complex technical answers with engineering when he doesn’t fully understand the implementation.
Compete on customer experience, not just product velocity. Everyone uses AI to ship faster products. Al uses AI to show up differently in customer relationships—delivering custom deployment documentation that accounts for each customer’s specific security requirements and infrastructure constraints. This differentiation in service quality is harder to replicate than product features.

Detailed workflow walkthroughs from this episode:

How Al Chen Uses Claude Code and 15 Repos to Answer Any Customer Question: https://www.chatprd.ai/how-i-ai/claude-code-and-repos-to-answer-any-customer-question
Automatically Create a Knowledge Base from Slack Support Threads: https://www.chatprd.ai/how-i-ai/workflows/automatically-create-a-knowledge-base-from-slack-support-threads
How to Use AI to Answer Customer Questions from Your Entire Codebase: https://www.chatprd.ai/how-i-ai/workflows/how-to-use-ai-to-answer-customer-questions-from-your-entire-codebase

If you’re enjoying these episodes, reply and let me know what you’d love to learn more about: AI workflows, hiring, growth, product strategy—anything.

Catch you next week,
Lenny

P.S. Want every new episode delivered the moment it drops? Hit “Follow” on your favorite podcast app.

I gave Claude Code our entire codebase. Our customers noticed. | Al Chen (Galileo)

Claire Vo — Mon, 06 Apr 2026 12:03:35 GMT

Al Chen is a field engineer at Galileo, an observability platform for AI applications, where he works on the front lines with enterprise customers asking highly technical questions. Despite never having held an engineering role, Al has built a system using Claude Code to query Galileo’s 15 separate repositories, combine that with Confluence documentation and customer-specific quirks, and deliver hyper-personalized answers that would otherwise require constant engineering support.

Listen or watch on YouTube, Spotify, or Apple Podcasts

What you’ll learn:

How to use Claude Code to query multiple repositories simultaneously for customer support
Why code is often a better source of truth than documentation
How to combine repository context with Confluence and Slack using MCPs
The “customer quirks” system that creates hyper-personalized deployment guides
How to build virtuous loops that turn single customer questions into scalable knowledge
Why information organization matters less in the AI era
A simple 16-line script (written by Claude Code) that pulls the latest main branch across all your repositories to keep your context current
How to reduce engineering interruptions to near-zero by empowering customer-facing teams to query the codebase directly

Brought to you by:

Orkes—The enterprise platform for reliable applications and agentic workflows

Tines—Start building intelligent workflows today

In this episode, we cover:

(00:00) Introduction to Al Chen

(02:50) The problem: documentation wasn’t enough

(04:23) Pulling 15 repos into VS Code

(06:03) How Claude Code queries the entire codebase

(08:00) Why current code beats documentation

(08:31) The pull script that keeps everything updated

(09:54) Opening projects at the multi-repo level

(11:40) Live demo: answering deployment questions

(13:25) The customer quirks system

(15:00) Living in chaos: why organization matters less now

(17:03) Competing on customer experience, not just product

(18:20) Should customers be able to query the code directly?

(20:05) Where humans still add value

(25:46) Using AI for reactive Slack support

(29:16) The “and then” workflow discovery

(32:07) Scaling processes across the team

(34:07) Lightning round and final thoughts

Tools referenced:

• Claude Code: https://claude.ai/code

• VS Code: https://code.visualstudio.com/

• Pylon: https://usepylon.com/

• Confluence: https://www.atlassian.com/software/confluence

Other references:

• Slack: https://slack.com/

• Kubernetes: https://kubernetes.io/

• Stack Overflow: https://stackoverflow.com/

• Intercom: https://www.intercom.com/

Where to find Al Chen:

LinkedIn: https://www.linkedin.com/in/thealchen/

Company: https://www.rungalileo.io

Where to find Claire Vo:

Read the full article here

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email jordan@penname.co.

Head of Growth (Anthropic): “Claude is growing itself at this point” | Amol Avasare

Lenny Rachitsky — Sun, 05 Apr 2026 12:31:45 GMT

Amol Avasare is Head of Growth at Anthropic, which is going through the most unprecedented growth trajectory in history—scaling from $1 billion to over $19 billion in ARR in just 14 months. Previously, Amol worked on the growth teams at Mercury and MasterClass. Before that he was a founder, and he cold emailed his way into the Anthropic role when no job listing existed. Most remarkably, he overcame a traumatic brain injury from a Muay Thai match that meant he couldn't work for nearly a year.

Listen on YouTube, Spotify, and Apple Podcasts

In our in-depth discussion, Amol shares:

How Amol landed his role by cold emailing Anthropic’s CPO Mike Krieger
How Anthropic is automating growth experiments with Claude (their internal tool called “CASH”)
Why the ratio of PMs to engineers might need to flip (more PMs than engineers) as AI makes engineers exponentially more productive
Why activation is the single highest-leverage growth problem in AI
Why Anthropic indexes 70/30 toward big bets (the opposite of most growth teams)
How he uses Cowork to detect team misalignment in Slack
How the company’s focus on AI coding created a research flywheel that accelerated their models

Brought to you by:

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs
Vanta—Automate compliance, manage risk, and accelerate trust with AI

Where to find Amol Avasare:

• X: https://x.com/TheAmolAvasare

• LinkedIn: https://www.linkedin.com/in/amolavasare

Referenced:

• How a traumatic brain injury made me a better PM—and person: https://www.lennysnewsletter.com/p/how-a-traumatic-brain-injury-made

• Anthropic: https://www.anthropic.com

• Snowflake: https://www.snowflake.com

• Canva: https://www.canva.com

• Palantir: https://www.palantir.com

• Atlassian: https://www.atlassian.com

• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next

• Claude Code: https://code.claude.com

• Dario Amodei on X: https://x.com/DarioAmodei

• Facebook: https://www.facebook.com

• Uber: https://www.uber.com

• DoorDash: https://www.doordash.com

• Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann

• Mercury: https://mercury.com

• MasterClass: https://www.masterclass.com

• Calm: https://www.calm.com

• Alexey Komissarouk’s website: https://alexeymk.com

• Alexey’s “Mastering Growth Engineering” course: https://www.reforge.com/courses/mastering-growth-engineering

• Claude Cowork: https://www.anthropic.com/product/claude-cowork

• Making an impact through authenticity and curiosity | Ami Vora (CPO at Faire, ex-WhatsApp, FB, IG): https://www.lennysnewsletter.com/p/authenticity-and-curiosity-ami-vora

• Ami Vora’s Substack: https://amivora.substack.com

• Benepass: https://getbenepass.com

• Brex: https://www.brex.com

• Granola: https://www.granola.ai

• The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead

• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom

• John Egan’s website: https://jwegan.com

• Workday: https://www.workday.com

• Figma: https://www.figma.com

• Spirit Rock: https://www.spiritrock.org

• This will make you a better decision-maker | Annie Duke (author of “Thinking in Bets” and “Quit,” former pro poker player): https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke

• Marty Supreme: https://www.imdb.com/title/tt32916440

• Maruhachi Shinsui Maruhachi Pro: https://www.amazon.co.jp/-/en/Maruhachi-Shinsui-Feather-Pillow-Blissful/dp/B081DNVD3K

Recommended books:

• The Joy of Living: Unlocking the Secret and Science of Happiness: https://www.amazon.com/Joy-Living-Unlocking-Science-Happiness/dp/0307347311

• Awareness: Conversations with the Masters: https://www.amazon.com/Awareness-Opportunities-Reality-Anthony-Mello/dp/0385249373

• Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts: https://www.amazon.com/Thinking-Bets-Making-Smarter-Decisions/dp/0735216371

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.

My biggest takeaways from this conversation:

🧠 Community Wisdom: Evaluating startup equity, navigating pre-seed fundraising, MCPs vs. CLIs, Monzo’s U.S. exit, and more

Kiyani — Sat, 04 Apr 2026 22:02:36 GMT

An AI state of the union: We’ve passed the inflection point, dark factories are coming, and automation timelines | Simon Willison

Lenny Rachitsky — Thu, 02 Apr 2026 12:32:28 GMT

Simon Willison is a prolific independent software developer, a blogger, and one of the most visible and trusted voices on the impact AI is having on builders. He co-created Django, the web framework that powers Instagram, Pinterest, and tens of thousands of other websites. He coined the term “prompt injection,” popularized the terms “AI slop” and “agentic engineering,” and has built over 100 open source projects, including Datasette, a data analysis tool used by investigative journalists worldwide. What makes Simon unique is that he’s made the leap from traditional software engineering to AI-native development more fully and visibly than almost anyone—and he’s been documenting everything he learns in real time on his blog, SimonWillison.net.

Listen on YouTube, Spotify, and Apple Podcasts

In our in-depth conversation, Simon shares:

Why November 2025 was the inflection point when AI coding agents crossed from “mostly works” to “actually works”
How Simon writes 95% of his code from his phone now and why he’s mentally exhausted by 11 a.m.
Why mid-career engineers (not juniors) are most at risk right now
The three agentic engineering patterns Simon uses daily (red/green TDD, templates, hoarding)
The next leap: the “dark factory” pattern where nobody writes or reviews code and AI does its own QA
Why prompt injection is an unsolved security problem and the “lethal trifecta” that will likely lead to an AI Challenger disaster
Why the pelican riding a bicycle became the unofficial benchmark for AI model quality

Brought to you by:

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs
Vanta—automate compliance, manage risk, and accelerate trust with AI

Where to find Simon Willison:

• X: https://x.com/simonw

• LinkedIn: https://www.linkedin.com/in/simonwillison

• Website: https://simonwillison.net

• Agentic Engineering Patterns: https://simonwillison.net/guides/agentic-engineering-patterns

Referenced:

• It genuinely feels to me like GPT-5.2 and Opus 4.5 in November represent an inflection point: https://x.com/simonw/status/2007904766756880848

• Claude Code: https://code.claude.com

• Codex: https://chatgpt.com/codex

• Head of Claude Code: What happens after coding is solved | Boris Cherny: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens

• There’s a new kind of coding I call “vibe coding”: https://x.com/karpathy/status/1886192184808149383

• Firefox: https://www.firefox.com

• Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding): https://www.lennysnewsletter.com/p/naming-expert-david-placek

• Windsurf: https://windsurf.com

• Thoughtworks: https://www.thoughtworks.com

• Cloudflare: https://www.cloudflare.com

• Shopify: https://www.shopify.com

• Jensen Huang: Nvidia’s Future, Physical AI, Rise of the Agent, Inference Explosion, AI PR Crisis: https://www.youtube.com/watch?v=gwW8GKwHB3I

• Inside Linear: Building with taste, craft, and focus | Karri Saarinen (co-founder, designer, CEO): https://www.lennysnewsletter.com/p/inside-linear-building-with-taste

• Hacker News: https://news.ycombinator.com

• Dario Amodei on X: https://x.com/DarioAmodei

• Lenny’s post on the job market in tech: https://www.lennysnewsletter.com/p/state-of-the-product-job-market-in-ee9

• Claude app: https://apps.apple.com/us/app/claude-by-anthropic/id6473753684

• Gemini: https://gemini.google.com/app

• Import and export your memory from Claude: https://support.claude.com/en/articles/12123587-import-and-export-your-memory-from-claude

• Wispr Flow: https://wisprflow.ai

• The last six months in LLMs, illustrated by pelicans on bicycles: https://simonwillison.net/2025/Jun/6/six-months-in-llms

• Gemini 3.1 Pro: https://simonwillison.net/2026/Feb/19/gemini-31-pro

• Redis: https://redis.io

• Node.js: https://nodejs.org

• Simon’s tools repository: https://github.com/simonw/tools

• Simon’s research repository: https://github.com/simonw/research

• Tesseract: https://github.com/tesseract-ocr/tesseract

• TDD: https://martinfowler.com/bliki/TestDrivenDevelopment.html

• Red/green TDD: https://simonwillison.net/guides/agentic-engineering-patterns/red-green-tdd

• The lethal trifecta for AI agents: private data, untrusted content, and external communication: https://simonwillison.net/2025/Jun/16/the-lethal-trifecta

• Prompt injection: https://simonwillison.net/series/prompt-injection

• The coming AI security crisis (and what to do about it) | Sander Schulhoff: https://www.lennysnewsletter.com/p/the-coming-ai-security-crisis

• AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt): https://www.lennysnewsletter.com/p/ai-prompt-engineering-in-2025-sander-schulhoff

• The Challenger Disaster: Normalisation of Deviance: https://psychsafety.com/normalisation-of-deviance

• Thanksgiving Day Chart—Behind The Net: https://www.blackswanreport.com/blog/2009/11/thanksgiving-day%C2%A0chart-behind-the-net

• CaMeL offers a promising new direction for mitigating prompt injection attacks: https://simonwillison.net/2025/Apr/11/camel

• OpenClaw: https://openclaw.ai

• Introducing ai.com—Your Private, Personal AI Agent: https://www.youtube.com/watch?v=n7I-D4YXbzg

• Tamagotchi: https://en.wikipedia.org/wiki/Tamagotchi

• NanoClaw: https://nanoclaw.dev

• Spider-Man 2: https://www.imdb.com/title/tt0316654

• Alfred Molina: https://en.wikipedia.org/wiki/Alfred_Molina

• AI for Data Journalism: demonstrating what we can do with this stuff right now: https://simonwillison.net/2024/Apr/17/ai-for-data-journalism

• Kākāpō: https://en.wikipedia.org/wiki/K%C4%81k%C4%81p%C5%8D

• Kākāpō Cam: Rakiura the kākāpō—2026 nest: https://www.youtube.com/live/BfGL7A2YgUY

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.

My biggest takeaways from this conversation:

Listen: OpenClaw: A power-user's guide to the most powerful personal AI tool since ChatGPT

Lenny Rachitsky — Wed, 01 Apr 2026 14:11:12 GMT

If you’re a premium subscriber

Add the private feed to your podcast app at add.lennysreads.com

Claire Vo went from public OpenClaw skeptic to running nine dedicated AI agents that manage her businesses, write code, close sales deals, and make sure she gets to her kids' basketball games on time. In this episode, she shares her complete power-user's guide to OpenClaw—covering everything from setup and key concepts to practical workflows and building your own team of agents.

Listen now: YouTube | Apple | Spotify

In this episode, you’ll learn:

What OpenClaw is and why it’s more autonomous and powerful than other AI tools
How to choose the right setup: Mac Mini, VPS, or a hosted option
Six ready-to-copy workflows you can start using immediately
How to run multiple agents with specific roles (Claire’s full 9-agent setup)
The best tools and integrations to connect your agents to the real world
Key security considerations and how to think about risk

Prefer text?

OpenClaw: The complete guide to building, training, and living with your personal AI agent

Claire Vo — Tue, 31 Mar 2026 12:45:57 GMT

P.S. Get a full free year of Lovable, Manus, Replit, Gamma, n8n, Canva, ElevenLabs, Amp, Factory, Devin, Bolt, Wispr Flow, Linear, PostHog, Framer, Railway, Granola, Warp, Perplexity, Magic Patterns, Mobbin, ChatPRD, and Stripe Atlas by becoming an Insider subscriber. Yes, this is for real.

“OpenClaw is probably the single most important release of software, probably ever.” —Jensen Huang, Nvidia CEO

Claire Vo has put together the definitive step-by-step guide to getting started with and mastering OpenClaw. Building on our podcast episode, this post covers everything you need from first install to running a full team of AI agents, plus the specific use cases that have changed her life. Whether you’re brand new to OpenClaw or already running one, Claire’s guide will level you up.

A big thank-you to Peter Steinberger, Dave Morin, and Nat Eliason for reviewing drafts of this post. For more from Claire, check out her podcast How I AI and ChatPRD, and find her on X and LinkedIn.

At 6 a.m., before I’ve looked at my phone, an AI agent named Polly has already read my email, checked my calendar, and queued up my day. By the time I sit down for coffee, another agent has reminded my husband about spirit day at school. A third AI is halfway through drafting a sales email, which will land in our prospect’s inbox three minutes after they contact us. One of the agents even helped draft this paragraph (though the rest was lovingly written by my human hands).

None of this existed three months ago.

If you’re paying attention to AI news, you’ve probably heard about OpenClaw. For a while, it seemed like X was nothing but lobster emojis and breathless posts about everything it can do: running your business, buying cars, planning the AI uprising with its friends, and more. You’ve also probably seen some horror stories, like when it started deleting this user’s full Gmail inbox, or that time it completely screwed up my own personal calendar.

You’re interested, and a little scared. I was too. But the idea of a dedicated personal assistant that could help run my life and businesses was so appealing that I had to dig in. The more I play with OpenClaw, the more convinced I am that it is one of the most powerful AI tools for personal use, and a sign of where these tools are going.

Fast-forward two months, I’m chatting 24/7 with my nine (and counting!) OpenClaw agents, which operate my businesses, write code, close sales deals, and make sure I get to my kids’ basketball games on time.

My OpenClaw agents in Telegram

OpenClaw is powerful but a little tricky to set up. After a lot of trial and error, I figured out how to make it work—and make my Claws work for me. Here’s exactly how you can too:

First, what is OpenClaw?

OpenClaw is an open-source personal AI assistant that is more powerful, more autonomous, and more fun to use than anything else I’ve tried. To tell it what needs to be done, you can message it easily on the platforms you already use, like WhatsApp, Telegram, Slack, etc. Then it can control your computer and take care of tasks just as you would, working on its own schedule—even overnight. It’s always on, runs locally, and it can build its own new skills. Teach it once; it handles the rest.

Practically, this means I can text my OpenClaw something like “Let’s make sure our website always has the latest reasons why we’re better than competitors.” It will use web search, our GitHub repo, and public APIs to find the information it needs, and ship PRs with the updates. Every week, it will refresh those pages with new data based on new features or market news.

One text turns into an always-on agent. But how you set it up is important, and understanding a few key concepts will save you tens of hours of frustration.

Key OpenClaw concepts:

It runs a local gateway that takes in messages. Think of this as a general-purpose inbox that can receive instructions from any channel (e.g. terminal, Telegram, WhatsApp, etc.)
Behind this gateway are agents, which have their own identities, tools, and workspaces
Agents work on a scheduled set of cron jobs and a heartbeat that gets checked every 30 minutes
It can use (and self-install!) skills, APIs, and CLIs to interact with systems and the outside world
It’s deployed on an owned machine, like a Mac Mini or a VPS on the cloud that you own and operate yourself

I’ve written in detail about the mechanics of OpenClaw here. The docs site is also very helpful, especially these top-level pages on channels, agents, and tools:

But enough theory. Let’s set up your sentient virtual lobster.

Setting up your first OpenClaw

What computer to use, and do you need a Mac Mini?

You have options for where to install your OpenClaw, but most importantly, do not install it on a work or personal computer that’s actively in use. This is very dangerous. OpenClaw can technically have access to all the files on the computer it runs on, and no matter how careful you are, you don’t want to risk deleting everything, or emailing your personal files to an unsavory character.

The OpenClaw team has done a great job of hardening security, but it’s best to start with an isolated box.

You have three safe options for installing OpenClaw:

Sign up for a hosted version of OpenClaw. Startups are popping up every week that make this easy to do. Some of the more popular options include StartClaw, MyClaw, SimpleClaw, UniClaw, and Every’s Plus One. I experimented with a few of these, and they are slick, but I always got stuck on something. These products will get better, and I expect this to be how most people will experience OpenClaw over time.
Have it run in a virtual private server. This may be the cheapest option, but it’s also the most complicated. Some of the more popular options include Railway, Hostinger, DigitalOcean, Google Cloud, and Render. I didn’t try going this route, but many technical people prefer it, because it’s quick, powerful, and doesn’t require new hardware.
Use a laptop or (yes) a Mac Mini. I started with an old MacBook Air and eventually moved to a stack of Mac Minis.

You don’t actually have to run it on a Mac Mini—you can use any computer, even an old laptop—but the Mac Mini is simple, powerful, and compact. And it’s kind of become a meme. This option is the most expensive, at least up front, and time-consuming, but also the most fun, educational, and cute!

If you can swing it, I’d try this. (I got the lowest-end model: M4, 16GB, 256GB, about $600.) Just remember to grab a keyboard, mouse, and a monitor for your initial setup. Use whatever you have lying around; you won’t need it again after everything is running.

Your pre-work

OK, you’ve got your machine booted up. Before we install the Claw, here are a few quick things that will make setup easier (this will take you about 10 minutes):

Set up a fresh admin account and password on the computer you’ll be using
Sign up for a Gmail address for your agent (later, you can give it read-only access to your calendar)
Make sure Chrome is installed, which is OpenClaw’s preferred browser

Installing OpenClaw

Opening the terminal and installing OpenClaw

Open the terminal (Command ⌘ + Space, type “Terminal,” hit Return), and run:

curl -fsSL https://openclaw.ai/install.sh | bash

This will install everything you need and drop you into the onboarding. If you get stuck, install Claude Code and/or Codex and ask for help!

Onboarding

Once the install is complete, OpenClaw will walk you through a guided onboarding flow step-by-step. The first step is acknowledging a security warning. Read this!

If you’re ready for the adventure, you can continue through the onboarding. Here are my pro tips for the key steps:

Know how to navigate the terminal

If you’re not familiar with working in the terminal, the onboarding process is a little confusing. Use arrow keys to navigate up, down, left, and right, spacebar to select, and enter to submit.

Pick your default model

I recommend Claude Opus 4.6 or Codex 5.4 (or whichever model is the most powerful at the time you’re reading this).

Authenticate your model provider

You have two options for using paid models like Opus or Codex:

1. Use an existing subscription by logging in to your Claude or ChatGPT account.

Note: There are some rumors that Anthropic is banning people who reuse their Claude accounts for OpenClaw. When using any third-party account with OpenClaw, review the terms of service and proceed at your own discretion.

2. Use an API key, which you can get by setting up a developer account at Claude or OpenAI. This is the recommended path, and what I use.

Choose a channel to “talk” to your agent

The best beginner-friendly channel is Telegram. More on this below.

Set up web search

This will give your Claw access to the internet. You can skip and set this up later when you need it.

Install skills from a list of bundled defaults

I recommend the gog skill for Gmail, Google Calendar, and Docs access and summarize to start.

Enable hooks

These are helpful tools that keep your OpenClaw setup optimized. I turned on all four of these, but session memory is the most important. The others are helpful when you want to debug or optimize your agent.

Then your agent will “hatch” in the TUI (Terminal UI). Hello, world!

Setting up Telegram

You’ll want a better chat interface than the terminal, so open up your phone and download Telegram, a messaging app and the simplest way to connect with your OpenClaw. If you ask OpenClaw, it can walk you through the setup steps, including messaging the @BotFather (yes, really).

Your first chat

Setting up your agent is where you should put on your manager hat. Just like an employee, it can’t be good at everything, so think about a specific job for your OpenClaw. Personal assistant? Social media manager? Engineering intern? Start with one idea and you can always add on more later. If you’re unsure where to start, begin with a personal assistant like I did.

This is where things get fun. Once your OpenClaw is hatched, it will start asking you about yourself and itself to build its definitions and operating model.

You should make sure to share:

Your name
Your role/job
Common admin challenges in your life (scheduling, remembering tasks, coordination with your family)

All this gets written down by the agent and stored in the workspace folder you set up in onboarding (usually .openclaw/[agent_name]-workspace) as Markdown files.

Those files become your agent’s identity and operating system. They are read every time your OpenClaw starts up and give your agent everything it needs to do a good job. It’s fun to look at these files; occasionally, you may need to go in and edit them.

AGENTS.md—OpenClaw’s core set of instructions and memory
SOUL.md—Your agent’s persona, tone of voice, and clear boundaries
IDENTITY.md—Your agent’s name, vibe, and personal emoji
TOOLS.md—Notes on tools and how your agent should use them
USER.md—All about you, your OpenClaw’s human

Once its identity and role is set, it should ask you to get started on a first task. Time to Claw!

How I AI: my personal OpenClaw setup

OK, so you finally have this bot set up. What do you actually do with it?

Six easy and useful OpenClaw workflows

I do a lot with my OpenClaw agents now, but below are some easy places to start. Just copy and paste these prompts and OpenClaw will do the rest.

1. Coordinate a busy weekend

Every Friday, group message me and my husband to confirm the kids’ weekend activity logistics. If there is a conflict, confirm who will pick up each kid and any adjustments we may need to make to lunch or dinner plans. Ask us to explicitly confirm the plan and update our shared family calendar.

2. Find trending topics and generate memes for social media

Every morning, search for trending Reddit topics (r/funny, r/technology) about product management. Use the MemeLord API to generate one image and one video meme, send it to me for approval, then post to TikTok.

3. Look through PLG sign ups for high value enterprise prospects, enrich and follow up

Every morning, look through the signups for the last 24 hours. Find everyone who signed up with a company domain, and categorize into high-value prospects based on our ideal customer profile. For ones with < 1,000 employees, send a light-touch email based on SALES_PLAYBOOK.md. For companies with > 1,000 employees, enrich their profile with Exa People API and confirm with me before sending.

4. “Just in time” meeting prep

Check all my calendars for any meetings starting in the next 30 minutes. If there is a meeting starting soon, send me a pre-meeting brief on Telegram. Include meeting title and time, who’s attending, and agenda if available from the calendar event description, and our last interaction based on the most recent email thread or meeting notes with this person/company.

5. Write support docs overnight

Every Friday evening, look over our resolved support tickets. If any question has been asked 3+ times this week: (1) flag it as a docs/FAQ candidate, (2) create a Linear issue and assign to @agent to add a docs page to/docs covering the answer, (3) include the standard answer you’ve been giving as a starting point in the issue description.

6. Project manage me

I have a project launching on . Keep a to-do list with everything I tell you I need to do for a successful launch, and break the plan down into daily tasks I can easily get done. At the end of the week, celebrate what I accomplished and flag what I missed. Make sure we do everything possible to make this project successful.

Running multiple agents: my biggest unlock

🎙️ This week on How I AI: How Stripe built “minions”—AI coding agents that ship 1,300 PRs per week + How to turn Claude Code into your personal life operating system

Lenny Rachitsky — Mon, 30 Mar 2026 15:03:26 GMT

How Stripe built “minions”—AI coding agents that ship 1,300 PRs weekly from Slack reactions | Steve Kaliski (Stripe engineer)

Listen now on YouTube • Spotify • Apple Podcasts

Brought to you by:
Optimizely—Your AI agent orchestration platform for marketing and digital teams
Rippling—Stop wasting time on admin tasks, build your startup faster

Steve Kaliski has spent over six years building developer infrastructure at Stripe. In this conversation with Claire, he breaks down Stripe’s “minions”: AI coding agents that ship about 1,300 pull requests per week, often kicked off with nothing more than a Slack emoji. He explains why the real bottleneck in engineering isn’t coding, how cloud development environments unlock parallel AI workflows, and what it takes to safely review thousands of AI-generated PRs. He also demos AI agents that can spend money, coordinate services, and complete tasks end-to-end without human involvement.

Biggest takeaways:

What’s good for human developers is good for AI agents (and vice versa). Stripe’s years of investment in developer experience—comprehensive documentation, blessed paths for common tasks, robust CI/CD, excellent tooling—directly translates to higher AI agent success rates. When you have clear docs on “how to add a new API field,” the agent can follow those same instructions. This creates a virtuous cycle: investments in DX improve agent performance, and investments in agent infrastructure (like cloud environments) benefit human developers too.
Activation energy is the real bottleneck, not coding speed. Steve hasn’t started work in a text editor in months. Instead, work begins in Slack threads, Google Docs, or support tickets—the natural places where ideas emerge. By allowing engineers to kick off development with a single emoji reaction, Stripe lowered the friction between “good idea” and “code in production.” This is especially powerful in large organizations, where coordination costs typically kill momentum before coding even begins.
Cloud development environments are non-negotiable for multi-threaded AI work. Running multiple AI agents in parallel requires cloud-based dev environments that can spin up in seconds, run isolated workloads, and never fall asleep. This infrastructure investment—which Stripe’s developer productivity team built long before AI agents—now enables engineers to run dozens of agents simultaneously without melting their MacBook Pros.
1,300 AI-written PRs per week requires shifting review capacity, not eliminating it. Stripe still reviews every AI-generated PR, but the review process relies heavily on automated confidence signals: comprehensive test coverage, synthetic end-to-end tests, and blue-green deployments that enable quick rollbacks. The bottleneck shifts from writing code to reviewing it—and eventually to generating enough good ideas in the first place.
Machine-to-machine payments unlock ephemeral, API-first businesses. In Steve’s birthday party demo, Claude Code autonomously paid Browser Base, Parallel AI, and Postal Form for single-use services—no human signup, no subscription, no dashboard. Businesses can now optimize for agent consumers rather than human users, focusing on “hyper-useful single APIs” instead of landing pages and admin panels. The economics become transparent: tokens and dollars sit side by side, making the true cost of AI work visible.
Treat AI agents like new employees, with progressive trust. Start with limited access, expand permissions as the agent proves reliable, and maintain clear boundaries. Each minion runs in an isolated environment with specific data access—the finance agent can read bank statements but can’t send messages; the scheduling agent can text but has no financial data. This physical partitioning prevents accidental data leakage and creates accountability.
The future of software is disposable and hyper-personalized. Steve builds custom iOS apps for his toddler—music players limited to six specific songs—despite having no iOS development experience. He describes this as “the disposability of software”: when AI can build apps in hours, you can create single-purpose tools for incredibly specific use cases and throw them away when they’re no longer needed.

Detailed workflow walkthroughs from this episode:

How Stripe’s AI ‘Minions’ Ship 1,300 PRs Weekly from a Slack Emoji: https://www.chatprd.ai/how-i-ai/stripes-ai-minions-ship-1300-prs-weekly-from-a-slack-emoji
How to Build an Autonomous AI Agent That Pays for Services to Complete Tasks: https://www.chatprd.ai/how-i-ai/workflows/how-to-build-an-autonomous-ai-agent-that-pays-for-services-to-complete-tasks
How to Automate Code Generation from a Slack Message into a Pull Request: https://www.chatprd.ai/how-i-ai/workflows/how-to-automate-code-generation-from-a-slack-message-into-a-pull-request

How to turn Claude Code into your personal life operating system | Hilary Gridley

Listen now on YouTube • Spotify • Apple Podcasts

Brought to you by:
WorkOS—Make your app enterprise-ready today
Lovable—Build apps by simply chatting with AI

Hilary Gridley returns to the podcast to share how her approach to productivity has completely evolved since her last appearance. Now a new mom and entrepreneur, she walks Claire through how she uses Claude Code as a personal operating system, managing everything from daily planning to life admin without complex tools or rigid workflows. Instead of building elaborate systems, Hilary leans into what she calls the “anti-system system”: letting AI observe her behavior, learn her preferences over time, and gradually take work off her plate. Together, Claire and Hilary explore how simple inputs—like capturing tasks with a shortcut or “yapping” to Claude throughout the day—can replace traditional productivity stacks and integrations.

Biggest takeaways:

The 10x impact framework: For any task, ask “If I were 10 times better at it, would it have 10 times the impact?” If no, automate it. If yes, keep it human. This applies to both work tasks and life tasks—including whether baking bread will bring you joy or feel like a chore.
Complexity has to earn its keep. Hilary only connects APIs and builds complex integrations after testing the “janky version” of a workflow for a week. Her hit rate is only 20% on workflows she actually continues using, so starting simple saves massive time.
The yappers API beats OAuth every time. Instead of connecting all your tools in the background, just talk to Claude about what you’re doing throughout the day. Hilary keeps Claude Code open in her terminal and narrates her work, letting Claude observe and take notes without complex integrations.
Let AI learn your preferences by observing, not by your defining them. Hilary never sat down to write out her ideal schedule. Claude just watches what she actually does (not what she says she’ll do) and adjusts preferences automatically. Real behavior beats aspirational planning.
Calendar management is the ultimate to-do list. You can’t say you take something seriously if you’re not putting time into it. But manually adding tasks to your calendar is tedious—so let Claude do it automatically based on what you say you want to accomplish.
Screenshots are your friend for getting started. Don’t wait for API access or permissions at work. Build a janky version with screenshots and voice dictation, prove it’s valuable, and then get the permissions you need. Half-baked ideas don’t deserve full access.
You don’t need coding knowledge to build Claude Code skills. Hilary just describes problems to Claude: “I keep forgetting to return things on time.” Claude asks a few questions, then builds the entire workflow—including checking return policies and drop-off locations automatically.
Test everything before integrating it into working systems. Hilary refuses to add new workflows to her daily routine until she’s tested them separately for a week. If something breaks, you don’t want it taking down systems that were already working.
Build the muscle memory by doing one thing with AI every day. The biggest barrier isn’t technical knowledge—it’s rewiring your brain to think “the alien in my computer could help with this.” Hilary went from “I’ll never use the terminal” to running her life in Claude Code in about a week.

Detailed workflow walkthroughs from this episode:

How I AI: Hilary Gridley’s “Anti-System” for Automating Life with Claude Code: https://www.chatprd.ai/how-i-ai/gridleys-anti-system-for-automating-life-with-claude-code
Create a Privacy-Protecting Demo Mode for Your Personal AI: https://www.chatprd.ai/how-i-ai/workflows/create-a-privacy-protecting-demo-mode-for-your-personal-ai
Build Custom AI Automations by Having a Conversation with Claude: https://www.chatprd.ai/how-i-ai/workflows/build-custom-ai-automations-by-having-a-conversation-with-claude
Automate Your Daily Planning with Claude Code and an iPhone Shortcut: https://www.chatprd.ai/how-i-ai/workflows/automate-your-daily-planning-with-claude-code-and-an-iphone-shortcut

If you’re enjoying these episodes, reply and let me know what you’d love to learn more about: AI workflows, hiring, growth, product strategy—anything.

Catch you next week,
Lenny

P.S. Want every new episode delivered the moment it drops? Hit “Follow” on your favorite podcast app.

How to turn Claude Code into your personal life operating system | Hilary Gridley

Claire Vo — Mon, 30 Mar 2026 12:04:24 GMT

Hilary Gridley is an entrepreneur, former product leader, and new mom who previously appeared on the podcast discussing AI for managers. She returns to share how she's transformed her approach to personal productivity using Claude Code as her primary tool for managing both professional work and life admin. Hilary demonstrates her "anti-system system"—a philosophy that prioritizes simplicity over complex setup, allowing AI to learn preferences through observation rather than upfront configuration.

Listen or watch on YouTube, Spotify, or Apple Podcasts

What you’ll learn:

How to capture to-dos instantly using a simple iPhone back-tap shortcut that requires zero app switching
The “10x impact framework” for deciding what tasks to automate versus where to invest your human effort
How to use Claude Code’s observation capabilities to build a preference file that improves over time without manual setup
Why the “yappers API” (talking about what you’re doing while working) eliminates the need for complex OAuth integrations
A workflow for breaking down overwhelming tasks into 10-minute first steps that actually get completed
How to create Claude Skills by simply describing problems rather than writing code or following tutorials
Techniques for using “recording mode” to demo workflows without exposing personal information

Brought to you by:

WorkOS—Make your app Enterprise Ready today

Lovable—Build apps by simply chatting with AI

In this episode, we cover:

(00:00) Introduction to Hilary Gridley

(02:43) The opportunity cost of time as a new mom and entrepreneur

(07:11) Philosophy of the anti-system system

(08:05) Demo: Planning your day with Claude Code

(10:00) Setting up simple iPhone shortcuts for task capture

(11:48) How Claude organizes reminders and learns preferences automatically

(16:19) Breaking down overwhelming tasks into manageable first steps

(23:40) The yappers API: talking to Claude instead of building integrations

(25:28) Daily logging and observation patterns

(27:45) Quick summary

(30:50) The power of screenshots

(32:55) 10x impact framework for automation decisions

(37:51) Applying the framework to different career stages

(39:29) Building a “recording on” skill for anonymizing demos

(44:11) Building a returns tracking skill from scratch

(48:31) Building the muscle memory to reach for AI tools

(50:18) Where to find Hilary

Tools referenced:

• Claude Code: https://claude.ai/code

• Obsidian: https://obsidian.md/

• iPhone Shortcuts: https://support.apple.com/guide/shortcuts/welcome/ios

• Cursor: https://cursor.sh/

Other references:

• Figma file Hilary demo’ed: https://www.writerbuilder.com/howiai

Where to find Hilary Gridley:

Substack: https://hills.substack.com/

Website: https://writerbuilder.com

Where to find Claire Vo:

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email jordan@penname.co.

From skeptic to true believer: How OpenClaw changed my life | Claire Vo

Lenny Rachitsky — Sun, 29 Mar 2026 12:31:50 GMT

Claire Vo is the host of our sister podcast, “How I AI,” a former product executive and engineer, and founder of an AI startup called ChatPRD. Claire now runs her business, podcast, and family life with the help of nine OpenClaw agents running on multiple Mac Minis and old laptops. In this episode, Claire shares her journey from OpenClaw skeptic (it deleted her family calendar the first time she tried it) to true believer, and gives a masterclass in using AI agents in real life.

Listen on YouTube, Spotify, and Apple Podcasts

We discuss:

The exact step-by-step process to install and set up OpenClaw (it’s easier than you think)
How to avoid the biggest OpenClaw mistakes (don’t install it on your main computer)
Actual use cases that have changed Claire’s life (e.g. family scheduling, inbound sales, podcast prep, and course management)
Why multiple specialized agents beat one general-purpose agent
The security risks everyone worries about—and how to handle them
Browser limitations, memory issues, and practical workarounds

Brought to you by:

Mercury—Radically different banking
Omni—AI analytics your customers can trust
Orkes—The enterprise platform for reliable applications and agentic workflows

Where to find Claire Vo:

• X: https://x.com/clairevo

• LinkedIn: https://www.linkedin.com/in/clairevo

• Podcast: https://www.youtube.com/@howiaipodcast

• Website: https://clairevo.com

• ChatPRD: https://www.chatprd.ai

Referenced:

• OpenClaw: https://openclaw.ai

• Claude Cowork: https://claude.com/product/cowork

• Fry’s Electronics: https://en.wikipedia.org/wiki/Fry%27s_Electronics

• Peter Steinberger on LinkedIn: https://www.linkedin.com/in/steipete

• Telegram: https://telegram.org

• WhatsApp: https://www.whatsapp.com

• Fin: https://fin.ai

• Why OpenClaw feels alive even though it’s not (this AI has a heartbeat but not a brain): https://x.com/clairevo/status/2017741569521271175

• 5 OpenClaw agents run my home, finances, and code | Jesse Genet: https://www.youtube.com/watch?v=96Vl8s3EQhk

• Executive Playbook for AI in Engineering, Product, and Design: https://maven.com/clairevo/ai-native-epd-org

• Zach Davis on LinkedIn: https://www.linkedin.com/in/zach-m-davis/

• ChatGPT Atlas: https://chatgpt.com/atlas

• Perplexity Comet: https://www.perplexity.ai/comet

• Browser (OpenClaw-managed): https://docs.openclaw.ai/tools/browser

• Buffer: https://buffer.com

• Brave: https://brave.com/search/api/

• Exa: https://exa.ai

• Hilary Gridley on X: https://x.com/yourgirlhils

• How to become a supermanager with AI: https://www.lennysnewsletter.com/p/how-to-become-a-supermanager-with

• How custom GPTs can make you a better manager | Hilary Gridley (Head of Core Product at Whoop): https://www.youtube.com/watch?v=xDMkkOC-EhI

• How to debug a team that isn’t working: the Waterline Model: https://www.lennysnewsletter.com/p/how-to-debug-a-team-that-isnt-working

• Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang

• How I built a 1M+ subscriber newsletter and top 10 tech podcast | Lenny Rachitsky: https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter

• Age of Attraction on Netflix: https://www.netflix.com/title/81779095

• Oura Ring: https://ouraring.com/

• Eight Sleep: https://www.eightsleep.com

• Hoopsalytics: https://hoopsalytics.com

• DJI Osmo smartphone gimbal: https://www.amazon.com/DJI-Stabilizer-Tracking-Extension-Stabilization/dp/B0FJ2L67HJ?ref_=ast_sto_dp

• Silent basketball: https://www.amazon.com/Rzkipdy-Silent-Basketball-Size-27-5/dp/B0FHFSQWPP/ref=sr_1_9

• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom

Recommended books:

• Treasure Island: https://www.amazon.com/Treasure-Island-Robert-Louis-Stevenson/dp/1505297400

• Alice’s Adventures in Wonderland: https://www.amazon.com/Alices-Adventures-Wonderland-Illustrated-Illustrations/dp/991673268X

• Charts for Babies: A Picture Book: https://www.amazon.com/Charts-Babies-Picture-Book/dp/1419785184

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.

My biggest takeaways from this conversation:

🧠 Community Wisdom: When AI velocity outpaces your product strategy, when your estimates keep slipping, one day in San Francisco, pairing Claude Code with Codex, and more

Kiyani — Sat, 28 Mar 2026 17:01:42 GMT

How Stripe built “minions”—AI coding agents that ship 1,300 PRs weekly from Slack reactions | Steve Kaliski (Stripe engineer)

Claire Vo — Wed, 25 Mar 2026 12:03:34 GMT

Steve Kaliski is a software engineer at Stripe who has spent the past six and a half years building developer tools and payment infrastructure. He’s part of the team that created “minions”—Stripe’s internal AI coding agents, which now ship approximately 1,300 pull requests per week with minimal human intervention beyond code review. In this episode, Steve demonstrates how Stripe engineers activate development work from Slack and leverage cloud-based development environments for parallel agent workflows, and demos machine-to-machine payments where AI agents transact autonomously with third-party services.

Listen or watch on YouTube, Spotify, or Apple Podcasts

What you’ll learn:

How Stripe’s “minions” write 1,300 pull requests per week with minimal human intervention
Why a good developer experience for humans creates better outcomes for AI agents
The critical role of cloud development environments in unlocking AI-powered engineering velocity
The machine payment protocol that lets AI agents spend money to accomplish tasks
The code review strategy for handling thousands of agent-written PRs
Why non-engineers at Stripe are starting to use minions to ship code
The future of software businesses built primarily for agent consumers

Brought to you by:

Optimizely—Your AI agent orchestration platform for marketing and digital teams

Rippling—Stop wasting time on admin tasks, build your startup faster

In this episode, we cover:

(00:00) Introduction to Steve

(02:39) Stripe’s minions and their effect on Stripe as a whole

(04:42) Why activation energy matters more than execution

(05:44) What is a minion? The technical architecture

(06:52) Demo: Activating a minion from Slack with an emoji

(09:04) Why good developer experience benefits both humans and agents

(11:22) Walking through the agent loop and system prompts

(13:42) Why Stripe chose Goose as their agent harness

(16:00) The role of Stripe’s developer productivity team

(17:15) Why cloud environments unlock multi-threaded AI engineering

(21:14) One-shot prompting: from Slack to shipped PR

(22:04) How Stripe handles code review for 1,300 AI-written PRs weekly

(23:44) Non-engineers using minions across the company

(24:53) Demo: Planning a birthday party with Claude and machine payments

(32:15) Quick recap

(35:08) The future of ephemeral, API-first businesses for agents

(36:36) Lightning round and final thoughts

Tools referenced:

• Goose (AI agent harness): https://github.com/block/goose

• Claude Code: https://claude.ai/code

• Cursor: https://cursor.sh/

• VS Code: https://code.visualstudio.com/

• Slack: https://slack.com/

• Browserbase: https://browserbase.com/

• Parallel AI: https://www.parallel.ai/

• PostalForm: https://postalform.com/

• Stripe Climate: https://stripe.com/climate

Other references:

• Stripe machine payments: https://docs.stripe.com/payments/machine

• Blue-Green Deployment: https://martinfowler.com/bliki/BlueGreenDeployment.html

• Git worktrees: https://git-scm.com/docs/git-worktree

Where to find Steve Kaliski:

Twitter: https://twitter.com/stevekaliski

LinkedIn: https://www.linkedin.com/in/steve-kaliski-079a7710/

Where to find Claire Vo:

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email jordan@penname.co.

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