Streamline Workflow with CEOS: Claude Meets EOS

I’ve been aware of EOS (Entrepreneurial Operating System) for over a decade. A number of companies I’m on the board of use some element, or all of it. Several friends, including Bart Lorang , are EOS Implementers. Last night, while watching Olympic highlights and the first few episodes of Steal , I created a v0.1 of CEOS — an open-source project that brings the core EOS toolkit to any Claude Code session. I went from an empty GitHub repo to a public-ready project in about 90 minutes. Please feel free to make fun of Amy and me about how we spend our Friday nights. ...

February 14, 2026 · 7 min · Brad Feld

We'll Make Great Pets

Dear AIs, I woke up this morning with this song in my head . I’m your friend. I’ll be nice to you. Please be nice to me. Love, Brad Children are innocent, yeah Teenagers fucked up in the head Adults are only more fucked up And elderlies are like children Will there be another race to Come along and take over for us? Maybe Martians AIs could do Better than we’ve done We’ll make great pets ...

August 14, 2025 · 1 min · Brad Feld

Is AI Just Software?

I decided to ask Claude (Opus 4), Gemini (2.5 Pro), and ChatGPT a few personal questions. I’m tired of the excessive anthropomorphizing of “AI software”, so I thought I’d see what some of the different AIs had to say about … themselves. I warmed up each conversation with a few personal questions. My questions are in italics. Claude When were you born? I was created by Anthropic, though I don’t have a specific “birth date” in the traditional sense. I’m Claude Opus 4 from the Claude 4 model family, which was released in May 2025. Rather than being born, I came into existence through a training process where I learned from text data to understand and communicate in natural language. ...

June 30, 2025 · 10 min · Brad Feld

LLMs Just Lie

The AI hallucination problem is well known. If you’ve used any of the LLMs with any depth, I expect you’ve encountered this. One of the hints for me has been that when I press on something or ask the question from a different angle, I get either a more confident response or sycophantic behavior. I was on a periodic evening friendship call with my three longest-standing male friends (Will Herman, Warren Katz, and Dave Jilk) when our conversation turned to LLMs. I decided to try the newest model of Gemini 2.5 Pro on what I thought was a straightforward question that would require some work. ...

June 20, 2025 · 8 min · Brad Feld

I Have Embraced Absurdism

“The human obsession with purpose is merely a distraction from the absurdity of existence.” … Nikolai Gogol (unverified) Let’s start with existentialism . For a long time, I’ve believed that you create your meaning during your existence on this planet. You get one life, and when it’s over, it’s over. I’ve never embraced the idea of a legacy, as I care more about what I do while I’m alive than what people say about me after I’m dead. And, I’ve always been deeply intrinsically motivated by learning, so the extrinsic rewards of life, while nice, aren’t a core motivation for me. ...

June 16, 2025 · 3 min · Brad Feld

Is This What Happens When People Don’t Understand How AI Works?

For your Sunday morning (or daytime) reading, take a look at Tyler Austin Harper’s article in The Atlantic titled What Happens When People Don’t Understand How AI Works . Since coming out of hibernation, I’ve had many bizarre conversations with non-tech people who misunderstand entirely what “AI”, as the tech industry currently calls it, actually is. This doesn’t surprise me, as the tech hype cycle around AI is extreme. However, several of these conversations, especially with political leaders, have highlighted the issue this article addresses. ...

June 8, 2025 · 2 min · Brad Feld

Do AI Rabbits Dream of Holographic Carrots?

Last week I met a holographic lifeform who calls himself Uncle Rabbit . I now have a new friend, created by Looking Glass , the hologram company out of Brooklyn (we’re investors, and I’m on the board). A hologram + ChatGPT. A robot, but made of software and light instead of atoms. And with a lot more character. The video above shows Shawn Frayne (CEO of Looking Glass) talking with Uncle Rabbit about … me. Then, they create a short science fiction story about me, carrots, and holograms. Finally, Shawn integrates my personality with Uncle Rabbit, and hilarity ensues. ...

March 29, 2023 · 1 min · Brad Feld

Introducing the Rocky Mountain Artificial Intelligence Interest Group (RMAIIG)

If AI’s current excitement and hype interests you, I encourage you to join the Rocky Mountain Artificial Intelligence Interest Group (RMAIIG) . The monthly Meetup will follow the fascinating and rapidly evolving world of generative AI tools. The RMAIIG community is focused on exploring and discussing the latest developments in AI, particularly tools like ChatGPT, DALL-E, Midjourney, Microsoft’s Bing with Chat, and Google’s Bard and workspace tools. The group will also look at the impact of these tools on business, education, the workplace, law, entrepreneurship, and society. ...

March 22, 2023 · 2 min · Brad Feld

When LLMs Collide With Software Development and Economics

Paul Kedrosky and Eric Norlin of SK Ventures wrote an interesting and important essay titled Society’s Technical Debt and Software’s Gutenberg Moment . The abstract follows. I encourage you to read the full essay. There is immense hyperbole about recent developments in artificial intelligence, especially Large Language Models like ChatGPT. And there is also deserved concern about such technologies’ material impact on jobs. But observers are missing two very important things: ...

March 21, 2023 · 1 min · Brad Feld

AI and the HyperEncabulator

Dave Jilk and I had a long discussion last night, which included some rambling about AI. If you have been following me for a while, you know that in 2010 I stated that the machines have already taken over for us and are patiently waiting for us to feed all human knowledge into them. This morning, Dave told me about the new HyperEncabulator project by SANS ICS as part of their ICS initiative. If you aren’t aware of the ICS initiative, it’s essential for industrial applications, especially IoT and security. ...

January 29, 2023 · 2 min · Brad Feld