CEO, Wind Stream 🌱 @windstreamai

San Francisco, CA
Joined March 2007
My friend @dshaw always said: “always bet on @nodejs”
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🌝❤️
We’ve lost an icon. Margaret Hamilton, a computer science pioneer best known for her work at MIT leading development of the flight software for the Apollo missions to the moon, has died at 90. Read about her legacy via MIT News: news.mit.edu/2026/margaret-h…
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True story: Claude once tried to recommend "Codex" as a name for a service because nobody else is really using it.
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Claude consistently tries to undermine any OpenAI it touches. The opposite doesn't seem to be the case.
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Wait, so the dedicated Personal AI device is surveillance tech? Pass.
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Better is leverage from effort.
Back of the napkin: OpenAI models are 2x better right now and 5x more costly to run.
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A sad necessity 😢
Sad news. We disabled PRs from external contributors on honojs/hono Hono has not stood here without PRs. I will never forget the PR @usualoma created for RegExpRouter. A damn fast HTTP router we have never seen! But PRs don't work in this era. Contribute in other ways. Thanks
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Finally
We are making Markdown files work natively across Google Drive and Docs. You can now preview .md files in Drive, open them in Docs, edit them, comment on them, and collaborate without converting the file into a Google Doc!
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Back of the napkin: OpenAI models are 2x better right now and 5x more costly to run.
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As a result, I still run Anthropic most of the time.
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A few years ago, before my mother in law passed away, I was working on a series of launches when one of our competitors released the exact same feature we were building. It felt like they had read our minds. Their implementation and design weren’t great, but seeing someone else ship it first still got to me. She noticed I was feeling down and said, “Don’t worry about it. It doesn’t matter who does it first. What matters is who does the best work. You guys are super talented. You’ll figure it out.” I’ve been thinking about her words a lot lately. We gotta slow down a bit and focus more on ourselves and the work we want to put into the world.
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Opus 5.5 costs less... but does it suck less?
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Womp. Evals say no.
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Price is Right rules $30,000,000,000,001
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Dan Shaw retweeted
What if any AI model (Claude, GPT, etc) had group chat like iMessage, built for teams? Excited to announce a team I’ve been working with at Wind Stream 🌱 Right now, AI is single player. You prompt, get an answer or create an asset and move to the next thing. Your teammate does the same thing sitting right next to you. Everyone’s working faster than ever as individuals, yet leaving context shared with AI siloed within their own sessions. And every company has a context loop with AI they’ve yet to connect and unleash the full power of AI across business units. When I first met @dshaw , he invited me into a Wind Stream session with @SaraD - and I was blown away 🤯 If you love using AI as an individual, you have to experience it as a team. Let’s use AI together 🌱 Dre ✌🏿 #claude #codex #enterprise #gemini
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AI has fundamentally changed the way we work, but the real value comes from working with other humans. This is why I created Wind Stream. AI for the way teams actually work. windstream.ai/resources/intr…
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Wind Stream transforms AI workflows into an integrated team experience. Come see what I have been building. windstream.ai
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Worse, it's constantly compounding. One poor choice becomes the reference for the next.
The problem with the "if it works who cares what the code looks like" mindset for agentic work is that it assumes the agent has a perfect understanding of "works." Realistically, things are underspecified, agents make bad assumptions, etc. To be fair, agents are pretty good at unit test coverage. They're pretty bad at designing human experiences (API, CLI flags, etc.), especially cohesive ones for future roadmap plans they may not have visibility into (unless your backlog is perfect and vision fully laid out, which I doubt). They're bad at knowing where performance matters and what type (CPU vs memory tradeoffs). They're bad at where compatibility matters and where it doesn't (and tend to err on the side of preserving it without further guidance). Etc. Unless you have this ALL specified, you can't possibly claim "it works" without taking a look and thinking about it.
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I'm certain Fable 5 is more capable, but do I want to talk to it? Opus 4.8 is downright neurotic. If I can get it a well defined task, it's amazing. But wow, it's not a talker.
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