Founder & Engineer | Previously EM at @stripe, Co-founder & CTO @lemonsqueezy 🍋
Elgin, Scotland
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After two years as an Engineering Manager at Stripe, I've decided it's time to get back to startups. Some reflections on the journey so far, what I've learned, and what comes next.
gilbitron.me/blog/leaving-st…
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For more context, I'm working on a production agentic workflow that contains multiple branches with LLM powered decision making (slow + expensive).
With Jev @typesafeai, our evals show the flow is ~55% more accurate and ~25% faster 👀
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Anyone else using @SparkMailApp find it incredibly slow on iOS recently?
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While on vacation I was car shopping, and thought it would be cool to have a car-check app but with an AI spin. You don't just get data in a big report, you get advice on what to do with it.
So I built it! 🎉 If you're buying used cars in the UK, check it out! motorverdict.co.uk
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A lot of this resonates with my own experiences. I quit a stable full time job with a young family to go and build Lemon Squeezy. Rewards don’t come without the risks.
No one alerted me at 40. So I'm alerting you.
(Bookmark, take notes, tell your friends)
1. When you turn 40 you'll see the difference between those who took risks and those who didn't.
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Snagged myself a proper icon the other day. Short of an R34, this is *the* defining car of the Fast & Furious era. I’ve wanted one of these since I was a teenager 👌
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Supercar ownership has been much more rewarding than I expected. Sure the driving experience is a tonne of fun. But the joy it brings other people is what has surprised me most. Random conversations in car parks with like minded folks has been an unexpected upside of owning a car like this 👌
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Now this is a novel use for AI 👌
i'm obsessed with AI DIY projects
my favorite one right now is this guy who built an AI system that listens for birds outside his apartment, figures out what species they are, and paints them on his wall.
here's how the whole thing works:
1. a cheap usb mic on his balcony listens for birdsong 24/7
2. BirdNET, Cornell's AI model trained on 6,000+ species, names each bird species from the sound alone (no camera needed)
3. every time it hears one, Gemini 2.5 Flash Image paints that exact bird in the style of an Edo-period japanese woodblock print
4. the new painting drops into a live collage of everything that's been singing outside in the last 24 hours
5. and it all shows up on a framed e-ink display on his wall that reads "heard today" like a little museum placard for his neighborhood
knowing which birds visit you used to take a field guide, a trained ear, plus years of patient practice.
teddy just glances at the frame on his wall and sees the cardinal came back this morning
honestly i'm highly tempted to build one myself haha
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Gilbert Pellegrom retweeted
[recruiting experiment!] if you and your friend are engineers and you want to lead a zero-to-one thing at @stripe, we want to hire both of you.
email jweinstein@stripe.com about yourselves and one idea of what to build to help people start and run a prosperous internet business.
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