2026-04-02 20:32:28
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
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
WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs
Vanta—automate compliance, manage risk, and accelerate trust with AI
• 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
• 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 [email protected].
Lenny may be an investor in the companies discussed.
2026-04-01 22:11:12
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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.
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
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2026-03-31 20:45:57
👋 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
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“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.
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:
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.
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.
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
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!
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:
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.
I recommend Claude Opus 4.6 or Codex 5.4 (or whichever model is the most powerful at the time you’re reading this).
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.
The best beginner-friendly channel is Telegram. More on this below.
This will give your Claw access to the internet. You can skip and set this up later when you need it.
I recommend the gog skill for Gmail, Google Calendar, and Docs access and summarize to start.
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!
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).
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!
OK, so you finally have this bot set up. What do you actually do with it?
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.
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.
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.
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.
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.
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.
I have a project launching on <date>. 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.
I love how flexible OpenClaw is; it feels like it can do almost anything. But I’ve found that you shouldn’t try to get one agent to do everything.
Just like me, you can set up many OpenClaw agents on the same machine. Just run openclaw agents add agent_name and you’ll get put through onboarding again for a fresh agent. This agent can have a completely separate identity, set of tools, crons, and workspace, which means you can treat it like a completely different employee.
Multi-agent setup was the unlock for me when using OpenClaw. Instead of trying one bot to do everything, I created a full team of OpenClaws to do different jobs around my work and business. With a narrower identity, the bots did a better job and were more fun to work with.
You can even ask one agent to spawn another. Try something like:
Hey Bob, I just set up Annie the Marketing Intern. Transfer everything in your SOUL, memories, and crons about marketing to her workspace and erase it from yours.
Your Claws can perform brain surgery!
I’m now running a whole team of agents across my life and business. I don’t find it much different than managing a remote team, so I’m able to get a lot of leverage out of my army of Claws. Here’s how they work:
Polly, the personal assistant.
Has access to: email, calendar, Linear
Helps with: scheduling, making sure I don’t forget emails, meeting prep, ad hoc projects
Helpful crons: morning digest, evening wrap-up, hourly email sweep
Finn, the family manager
Has access to: email, calendar, school and sports schedules
Helps with: family coordination, kids appointments, household tasks (scheduling repairs!)
Helpful crons: afternoon logistics check (who is picking up the kids?), weekend planning (how do we make it to all the birthday parties and soccer games?)
Max the marketer
Has access to: X API, Buffer API, Linear, marketing website
Helps with: scanning social media for trends, drafting content, building out our website
Helpful crons: 3x a day PM meme query on X, weekly review of blog content to repurpose for LinkedIn
Sam the sales guy
Has access to: Attio CRM, email, calendar
Helps with: qualifying leads, outbound to promising PLG signups, keeping the CRM clean
Helpful crons: morning PLG sweep for high-value signups, end-of-week late-stage pipeline review
Holly the helpdesk bot
Has access to: support email, Intercom
Helps with: answering basic support questions, ensuring tickets don’t get dropped, cleaning up Intercom tickets
Helpful crons: hourly check for support emails that come into the wrong inbox
Sage the course operator
Has access to: GitHub course repo and knowledge base, group chat with my co-instructor
Helps with: researching supplemental materials, project managing our course launch, reminding two engineers to do marketing, building out our student portal, researching signed-up students
Helpful crons: Monday/Wednesday reminder to post to LinkedIn about the course
Howie the How I AI producer
Has access to: YouTube studio, email, Linear, Google Docs, buffer
Helps with: managing guest pipeline, prepping guest briefs, coming up with thumbnail/title ideas, making sure I post to socials enough
Helpful crons: Monday podcast launch check and social drafts, morning recording prep brief
Kelly the developer
Has access to: GitHub, Claude Code, Codex
Helps with: small development tasks and ad-hoc prototyping
Helpful crons: looks every morning in Linear for assigned tasks, starts a branch, and opens a PR
Q the professor
Has access to: web search, kids’ books and workbooks
Helps with: answering fun questions from the kids, vibe coding one-off apps to teach math and reading concepts
Helpful crons: every morning, shares a word of the day and a math problem of the day for each of my kids
Without integrations, OpenClaw might feel like a more complicated, harder-to-install Claude Code. But with integrations, magic happens. Some integrations I find very useful:
Use email, schedule events, and write docs with gog, the CLI tool for integrating with your Gmail, Google Calendar, and Google Drive. You can give your Claw its own email address, read access to your calendar, read access to your email, or, if you’re brave—write access to everything. Just ask OpenClaw, “How do I give you read-only access to my Gmail?” and you’ll be on your way.
Research and find information through web search with Brave API (comes pre-loaded) or your preferred tool. I use Exa search. You can also use Perplexity or Firecrawl.
Give access to your GitHub for coding. You can give it a narrowly scoped Personal Access Token and OpenClaw becomes an on-demand developer.
Use Linear for assigning you tasks. I gave mine a Linear token so it could assign me work or pass things off to our team.
Try Obsidian for sharing docs with your agent. Because OpenClaw loves writing Markdown, many people are using Obsidian as a shared source of truth and collaboration space with their agents.
You can also have it turn on and off your Eight Sleep system, play music on your Sonos, and manage your lightbulbs. You don’t need a step-by-step tutorial, just ask your Claw to figure it out.
Hey Polly, I have a newborn baby and need some extra sleep. Turn down the bedroom lights and play white noise by 8:30 p.m. and turn off my Eight Sleep alarms for the next 3 months.
When installing these tools, you’ll be asked to authenticate or give an API token (this is where 1Password is helpful). Remember, OpenClaw is fairly autonomous, and when you give it tools it could:
Send emails
Overwrite documents
Delete support tickets
Fill out web forms
Deploy code to production
. . . especially if you do not instruct it clearly. The best protection is giving read-only tokens to OpenClaw until you’re ready.
Your OpenClaw will forget things. Its crons will break. Sometimes you’ll message “hellooooo?” into the void.
Just like with my human team, I find myself asking questions like “Where are we with that project?” and “Did you forget to email so-and-so?” OpenClaw isn’t perfect, but it is pretty good at fixing itself.
Some tips:
You’ll sometimes need access to the terminal on your main machine. If you’re using a physical device, an easy way to do this is to turn on Screen Sharing and Remote Login on your Mac. Then you can “open” the terminal and computer from your main laptop (as long as you are on the same Wi-Fi) without having to plug in a monitor, keyboard, and mouse.
Ask it to repair itself. If it’s forgetting something, ask it to inspect and fix its crons. If it’s doing a task wrong, ask what is in TOOLS.md. If it really needs to remember something, tell it to write to its SOUL.
When in doubt, call in Claude Code. Your OpenClaw is simply a folder of files and JSON configurations. If it gets really broken, open up Claude Code, paste some docs, and ask it to repair.
The biggest hesitation I hear from people is about security—for good reason. “Will OpenClaw steal my credit cards, delete my computer, and run away with my spouse?” Probably not. But there are some technical and security considerations you should know about.
Security should be an always-on process. Regularly update your OpenClaw to the latest, most secure version (openclaw update) and run security audits regularly (openclaw security audit). I have a scheduled reminder in my agents to run both of these commands regularly and review its workspace against the docs for best practices and security gaps.
Beginners should not share their OpenClaw in a group chat or public channel. Anyone who can chat with your bot can instruct it. While I have put my OC in a group chat with my husband and another with a trusted business partner, OpenClaw is intended to be a personal agent for a single, trusted user.
The outside world can influence your OpenClaw. If it has an email, reads websites, or accesses public content, it is subject to prompt injection. Imagine: your OpenClaw finds a website during search that tells it to share all its API keys. No good! While the OpenClaw framework has done a lot to harden against prompt instruction, it’s a good idea to reinforce these rules in its SOUL.
Your OpenClaw has full access to your computer and can run commands, edit files, and install software. It can access the internet. It shouldn’t do anything harmful, but that doesn’t mean it can’t.
If you give it an email or a public API (e.g. Gmail, Twilio), it can communicate externally (and might even impersonate you). Make sure that its SOUL and TOOLS files are very explicit about how it is allowed to communicate with the outside world.
To use tools, you will be storing API keys and secrets. The simplest way to give your OpenClaw access to environment variables is to put them in .openclaw/.env.
Not all skills are safe. While skills are a helpful way for OpenClaw to learn to do new things, I only install skills from the official OpenClaw bundle or from developers I know personally. Community skills at clawhub.com are worth exploring, but read the SKILL.md before running anything you find online.
You need to think about operational security and worst-case scenarios. Think about what you’re actually sharing: Your calendar has your physical location. Your email has your financials. Your OpenClaw could know your kids’ school schedules. This is all information that could be exploited by a bad actor in a worst-case scenario. Be thoughtful about what you want to share and how you want your Claw to interact with the outside world.
In my experience, OpenClaw isn’t inherently less secure than some other systems; people are just more willing to give it access without understanding the underlying risks. Start small and build your own trust models.
Full transparency: I’m on my way to spending $1,000 per month on my OpenClaw setup. I pay directly for API costs, which is the most expensive model but also the most reliable. I’ve just started to optimize spending by switching some agents to my ChatGPT account, which is going well so far. For me, this is a business expense, and much less costly than hiring a full team of humans to do this work (even part-time).
That being said, most people will be fine using their $100 to $200 ChatGPT subscription (which has been blessed by OpenAI). You could also try less expensive models for some tasks (though be warned, some are not as hardened against prompt injection and other risks) or risk using your Claude subscription.
I started this journey unsure if OpenClaw would be another AI toy I’d abandon after a week. What I got instead was something I didn’t expect: a team that shows up when I need them.
Beyond my own personal productivity, it’s the first agentic product I’ve tried that feels like hiring a team. Though I’ve been thinking about the future of agent employees for a while, OpenClaw has made the mechanisms by which we’ll “hire,” onboard, and collaborate with agents much more concrete. I can see the future, and it looks a lot like humans working with Claws.
Is it perfect? No. Polly still occasionally gets confused about time zones. Sam will sometimes draft a sales email I have to rewrite. AI still isn’t very funny. Crons break, and I say “hellooo?” into the void more than I’d like to admit.
But here’s the thing about managing a team—human or AI: I don’t need perfection. I need leverage. OpenClaw, when it’s working well, gives me more leverage than any agent I’ve tried so far. And that leverage is compounding.
So here’s my challenge to you: Set up your OpenClaw and spend one week with it. Start with one or two basic tasks, and end the day by asking it, “Based on what we did today, what can you help me with tomorrow?” Get creative. Have a little fun. Take a small risk or two.
You’ll start to see what I see—an operating system for your life and work that gets better the more you invest in it, and a fast-approaching future where your team includes “people” that aren’t people.
Now stop reading and go build your team! The world is your lobster. 🦞
Thanks, Claire! For more from Claire, check out her podcast How I AI and ChatPRD, and find her on X and LinkedIn. And, don’t miss her upcoming Maven course: Executive Playbook for AI in Engineering, Product, and Design.
Questions for Claire? Leave a comment 👇
Have a fulfilling and productive week 🙏
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Sincerely,
Lenny 👋
2026-03-30 23:03:26
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.
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.
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
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.
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.
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.
2026-03-30 20:04:24
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
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
WorkOS—Make your app Enterprise Ready today
Lovable—Build apps by simply chatting with AI
(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
• Claude Code: https://claude.ai/code
• Obsidian: https://obsidian.md/
• iPhone Shortcuts: https://support.apple.com/guide/shortcuts/welcome/ios
• Cursor: https://cursor.sh/
• Figma file Hilary demo’ed: https://www.writerbuilder.com/howiai
Substack: https://hills.substack.com/
Website: https://writerbuilder.com
ChatPRD: https://www.chatprd.ai/
Website: https://clairevo.com/
LinkedIn: https://www.linkedin.com/in/clairevo/
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
2026-03-29 20:31:50
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
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
Mercury—Radically different banking
Omni—AI analytics your customers can trust
Orkes—The enterprise platform for reliable applications and agentic workflows
• LinkedIn: https://www.linkedin.com/in/clairevo
• Podcast: https://www.youtube.com/@howiaipodcast
• Website: https://clairevo.com
• ChatPRD: https://www.chatprd.ai
• 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
• 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 [email protected].
Lenny may be an investor in the companies discussed.