Software Engineer from 🏴󠁧󠁢󠁳󠁣󠁴󠁿 Engineering Manager at @stripe. Co-founder & CTO @lemonsqueezy 🍋

Joined April 2008
615 Photos and videos
A great articulation of how I feel about my own work with AI atm 👌 Plus some great advice on how to counter it.
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Yikes 😬
Introducing Ferrari Luce, the first electric Ferrari designed by LoveFrom.
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Managed Payments is now GA 🎉
Apr 29
Stripe Managed Payments is now generally available. Sell digital products in 195 markets with our merchant of record solution for tax, fraud, disputes, and support.
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Excellent write up on what it takes to build a production-quality agent.
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Got the R8 out for a spring clean this morning 👌
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This is huge! JR is one of the highest calibre people I know when it comes to getting the right stuff done at scale. Some of the sharpest founder-mode instinct that exists. Congrats man 🙌
Big personal update. My role @stripe is evolving, and I couldn't be more excited. 💜 Most of my career, I’ve been focused on helping founders get paid on the internet. Now I’m shifting to what happens after. I’m leading Financial Accounts at Stripe, and I'll be focused on how businesses store, move, and spend money. Imagine being able to spend your Stripe balance immediately. No waiting a week for your funds to arrive in your bank account. It just works the way you'd expect money to work. Still early, with plenty to build. Exactly the kind of problem I love.
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Meanwhile, in Ireland 😂
AGI has been achieved in Ireland. Artificial Guinness Intelligence. Engineer Matt Cortland built an AI voice agent named Rachel, gave her a Northern Irish accent, and pointed her at every pub in the country. Over St. Paddy's weekend, she rang 3,000 of them to ask one question: how much for a pint of Guinness? How he built it: ElevenLabs for the voice, Twilio and an old Irish SIM to place the calls, Google Places API to map 5,200 pubs across all 32 counties, and Claude to parse the transcripts for prices. 2,052 picked up. Barely any even realized she was AI. The whole operation ran him about €200. The result is a live price index he's calling the Guinndex. Ireland's statistics office used to track pint prices, but stopped in 2011. An engineer with a weekend and a voice agent just picked up where they left off.
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Is there something that has the agentic accessibility of markdown files combined with the cloud-based, human collaboration features of Google Docs? I feel like this needs to exist.
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Been waiting for this. Does this make RAG obsolete?
Mar 13
1 million context window: Now generally available for Claude Opus 4.6 and Claude Sonnet 4.6.
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Gilbert Pellegrom retweeted
Mar 10
OpenCode’s rules for fighting slop: - don’t ship features just because you can - leave the code better than you found it - fixing features & process > new features so well reasoned
Mar 10
sent this to the team today everything great comes from being able to delay gratification for as long as possible and it feels like we're collectively losing our ability to do that
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Gilbert Pellegrom retweeted
Today we're announcing Polyscope - the free agent orchestration tool of my dreams. Run dozens of AI agents at the same time, blazing fast copy on write clones, a built-in preview browser you can use to visually prompt your agents, and much more. getpolyscope.com
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Gilbert Pellegrom retweeted
Really great articulation around startup moats and defensibility. #recommend
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And so it begins…
Feb 26
we're making @blocks smaller today. here's my note to the company. #### today we're making one of the hardest decisions in the history of our company: we're reducing our organization by nearly half, from over 10,000 people to just under 6,000. that means over 4,000 of you are being asked to leave or entering into consultation. i'll be straight about what's happening, why, and what it means for everyone. first off, if you're one of the people affected, you'll receive your salary for 20 weeks 1 week per year of tenure, equity vested through the end of may, 6 months of health care, your corporate devices, and $5,000 to put toward whatever you need to help you in this transition (if you’re outside the U.S. you’ll receive similar support but exact details are going to vary based on local requirements). i want you to know that before anything else. everyone will be notified today, whether you're being asked to leave, entering consultation, or asked to stay. we're not making this decision because we're in trouble. our business is strong. gross profit continues to grow, we continue to serve more and more customers, and profitability is improving. but something has changed. we're already seeing that the intelligence tools we’re creating and using, paired with smaller and flatter teams, are enabling a new way of working which fundamentally changes what it means to build and run a company. and that's accelerating rapidly. i had two options: cut gradually over months or years as this shift plays out, or be honest about where we are and act on it now. i chose the latter. repeated rounds of cuts are destructive to morale, to focus, and to the trust that customers and shareholders place in our ability to lead. i'd rather take a hard, clear action now and build from a position we believe in than manage a slow reduction of people toward the same outcome. a smaller company also gives us the space to grow our business the right way, on our own terms, instead of constantly reacting to market pressures. a decision at this scale carries risk. but so does standing still. we've done a full review to determine the roles and people we require to reliably grow the business from here, and we've pressure-tested those decisions from multiple angles. i accept that we may have gotten some of them wrong, and we've built in flexibility to account for that, and do the right thing for our customers. we're not going to just disappear people from slack and email and pretend they were never here. communication channels will stay open through thursday evening (pacific) so everyone can say goodbye properly, and share whatever you wish. i'll also be hosting a live video session to thank everyone at 3:35pm pacific. i know doing it this way might feel awkward. i'd rather it feel awkward and human than efficient and cold. to those of you leaving…i’m grateful for you, and i’m sorry to put you through this. you built what this company is today. that's a fact that i'll honor forever. this decision is not a reflection of what you contributed. you will be a great contributor to any organization going forward. to those staying…i made this decision, and i'll own it. what i'm asking of you is to build with me. we're going to build this company with intelligence at the core of everything we do. how we work, how we create, how we serve our customers. our customers will feel this shift too, and we're going to help them navigate it: towards a future where they can build their own features directly, composed of our capabilities and served through our interfaces. that's what i'm focused on now. expect a note from me tomorrow. jack
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I want something like this.
what's the current best approach on an AI that can help me handle my email inbox? seems like a big opportunity for folks playing with openclaw. For all of us who are drowning in email, this seems like a tier one problem that would be amazing to solve. (And I think I would pay $150k/year to have this product? I bet I'm not the only one) what I want is: - watch my inbox and process emails as they come in - score each message to see if it seems important (look at the sender, the topic/body, if its addressed to me or a big list, if I've ever replied to the sender before, etc etc) - read the email and reference a vast DB of knowledge that's been assembled already (based on my work, meeting notes, what I've replied on, etc), and decide what to do - reply with a draft note. For now, don't send, so that I can review the email -- but in the future maybe there's a YOLO option (but it would probably disclose that it's my assistant writing) - if less important, label it and file away. Eventually gather summaries for all of these less important emails and send me a summary of all of them with links to get back to it - or archive if it seems unimportant - or unsubscribe / mark spam / block if random marketing - if critical send me a notification right away so I can take a look I've played around with a bunch of the current AI tools and nothing quite works like this. There's a lot of blockers: - first, it needs 1000x more context about each problem, which it could get by crawling all my projects/notes/emails/slides/meetings/etc - This system should be designed to take action rather than simply just prioritizing messages. We've had prioritized inboxes for a long time but they're fine, not great - then someone has to put this entire UX together to be cohesive. In the future, we may not even really have an email inbox, but instead an interaction that feels more like I'm talking to an assistant who has a few questions for me. But otherwise just wants to provide a few quick updates and get some yes/nos. And otherwise filter all the noise -- just give me the most important messages It feels like we're very, very close to being able to do this, with the latest models from Anthropic and Open AI, we have the technology already. Someone just needs to package it all together in a way where it's able to index all of your emails and notes and calendars and contacts and sort of create a second brain that knows almost everything that you know so that I actually do things that are intelligent. It seems like with the excitement of OpenClaw we have the architecture to integrate a lot of different data sources and to take actions across multiple different channels. And it's built with one sort of monolithic memory and context, so that you're able to interact with it in such a way where it feels like it can try to replicate your actions more closely than the relatively stateless and memoryless LLM chats that we've gotten accustomed to. If someone is working on this, please point them to me. I would be both a customer and an investor!
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Stripe MoR is finally here 🎉
Feb 12
Today we're launching a public preview of our new merchant of record solution: @stripe Managed Payments. Everyone can try it.
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This is how we’re working with agents at Stripe.
At Stripe we have a tool called "minions" -- it lets us kick off async agents built right in our dev environment to one-shot bugs, features, and more e2e. I have team, project, and personal channels dedicated just to working with minions. I like to think of it as a new type of pair programming -- "pair prompting." Read more --> stripe.dev/blog/minions-stri…
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Best list of actually useful @openclaw use-cases I’ve seen.
a lot of the conversation around @openclaw has been extreme (and hilarious), but it's turned a lot of regular people off. don't return your mac mini yet! jotted down some real use cases (only possible on mac mini): brandon.wang/2026/clawdbot
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This is probably the best metaphor for what PMF feels like I’ve ever seen 😂
Finding product market fit as a solo founder.
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What a time to be alive!
so just to recap this week (so far) - musk industries is real (spacex, tesla, xai merger) - clawdbot explosion leading to a bankrun on mac minis but then anthropic released their own version - tesla dropped the bomb they’re halting production on model s and x to scale 1M optimus humanoid robots this year instead - china dropped the mother of all open source models kimi k2.5 that turn video into production-ready apps but then google dropped a gemini update ON THE SAME DAY that does the same thing gg - google said fuck it and also launched the worlds greatest world model genie and switched on gemini for 3.8B chrome browser users AND released alpha genome model that one-shots 1M dna base pairs for 3000 researchers across 160 countries AND teased new veo model - microsoft crushed earnings, launched a new ai chip but stock still tanked 10% because they *only* grew rev 39% - anthropic round 2X oversubbed raised to 20B 🏌️ - openai raising another $100B, 750B val 🏌️ - intel leaked they’re gonna help produce nvidias next gen feynman gpus - hello americas tsmc - a robot (built by figure) washed the dishes with zero human interaction - apple acquired stealth startup for $2B that can lip read - integrating their tech for new ai consumer airpods with cameras and mics - demis confirms google glass 2.0 coming this summer fckin hell
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