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Wisdom
Leadership, scale, and the inner work of becoming — field notes from a 3x founder and executive coach.
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Founder CoS v3: Portable, Mobile, Interactive
In Twin Peaks, FBI Special Agent Dale Cooper investigates a murder in a strange town with a handheld tape recorder and an assistant named Diane. You never see Diane. Cooper just raises the recorder mid-stride, says "Diane," and starts talking: observations, hunches, the weather, the trees, what he ate for breakfast. He dictates the thought as it happens, from wherever he is, and trusts it lands with someone who will hold the context. It dawned on me as I started using Wispr Flow to talk to my u
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A Founder Talks to Her Shopify Store Like a Dev Team
A Shopify rebuild, a live revenue surface, and the safety system that made Codex useful A DTC beauty founder came to Superculture needing her Shopify store rebuilt. We used Codex. But the first thing we built wasn't a page. It was a safety system. That sounds backwards, because the public story of AI is speed: point the model at the thing, describe what you want, watch it go. But a live ecommerce store isn't a sandbox. There's a cart. Checkout. Product data. Admin. Redirects. Discount terms. A
Read moreOne Kubrick, Two models
When the govt shut down Fable this past weekend, some of us wondered if we'd grown too dependent on a single model. A single model is a single point of failure. To be clear: I was loving Fable, and I can't wait to use it again. But I've been using Codex to build a DTC company's agentic operating system, it's been impressing me, and when Fable went down it hit me that I could just point Codex at the same repo and (maybe?) get similar results. I'd planned to play with Hermes this week but this se
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What I've Learned Building a No-Code Chief of Staff in Cowork
Six weeks ago I gave Claude a folder of markdown files and a name for my new agent: Kubrick 1000. The idea came from a friend's challenge. He'd hacked together his own chief of staff on a Mac mini and the command line. Could you build a no-code version in Cowork that runs off your own laptop? We weren't sure it would have the fidelity necessary, but it seemed like a worthwhile pursuit. There'd be a much larger audience for something that required less coding skill and worked with a graphical us
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Help-Shaped AI
We had planned to take our five-year-old to the free Darth Vader skate down at the waterfront but the weather was not cooperating. It's the kind of pop-up event we find buried in our group chats or newsletters: a free outdoor sakting event in Brooklyn Bridge Park, costumes encouraged, and, since our son had just discovered Star Wars, the kind of thing that makes you feel like you're winning at parenting if you actually make it there. We had the bag packed. Our son had his lightsaber... But....
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AI Time
I've been programming since elementary school. I lived through the PC revolution, the web, social, cloud, mobile. I've never seen anything like this. We used to call it "internet time." The dizzying pace where technology, society, and human life accelerate together. AI Time makes internet time look quaint. Over the past two weeks I've talked with friends at every frontier model company. Every conversation circles the same two ideas: we've never seen change move this fast, and nobody has a map
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CoS v2 - Cloudy Visions
v2 of building an AI chief of staff in public. Herein lies twelve scenes from cutting loose from the desktop and learning what running it from Anthropic's cloud actually entails. In this episode I explore moving my second brain to git and my scheduled tasks to routines in Anthropic's cloud. NGL all of this was far more complicated than I had intended or anticipated – tread lightly, dear reader. TL;DR — the v2 upgrades * Brain in cloud: my "second brain" (all MD files) live in a private GitHu
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Chief of Staff (CoS) in a Box
v1 (Cowork edition) Quickstart. Open Cowork. Create a new project, name it whatever you'd call your CoS (mine's Kubrick). Connect Gmail, Google Calendar, Slack, and Docs (built-in connectors, no code). Drop v1-desktop.md into the workspace folder. In Cowork, say: "Read v1-desktop.md and help me build my chief of staff." It walks you through everything. ~2-3 hours to a working CoS. I used my new chief of staff to draft this post. I shared a dozen samples of my writing with it and told it to go
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The 7 Ways to Build an AI Chief of Staff (And How to Pick the Right One for You)
What the smartest people do on the weekend is what everyone else will do during the week in ten years. The smartest folks I know are building an AI Chief of Staff for themselves.
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The Slow Startup Movement
What if, instead of speeding everything up, AI let us build intentional businesses? We're all so busy arguing about whether AI will replace programmers, kill creative jobs, or consolidate power into fewer and fewer companies. I think there might be a quieter possibility nobody's talking about, one far more radical and less dystopian than any of those arguments. I had a conversation with a former client, and fantastic CTO who, after some initial skepticism, has fully drunk the AI Koolaid. We
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The rise of agentic capital
VC runs on relationships, conviction, and speed, and yet until recently still moved at the pace of lawyers, signature blocks, and filing cabinets. In a world where deals get oversubscribed in a day and AI changes by the week, that's increasingly absurd. This week Fred Wilson announced that Spencer Y. spent the past six months building an agentic AI system to track and execute deals for USV. And Vic Singh recently launched Originalis AI, an ambitious new operating system for VC - looks like the
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The Strange Fatigue of Infinite Leverage
This isn't burnout. It's something else. The strange fatigue of having more capability than time. The exhaustion I'm feeling isn't from the work, it's from the gap between what's suddenly possible and the hours I don't have to explore it.
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The examined life is what makes you dangerous
"The unexamined startup is not worth founding" — Socrates (sort of) I had a client, a brilliant VC, who was terrified of being an "NPC." To him it meant being a lemming, falling victim to crowdthink, being predictable, not just being a coward but being unaware of your inconsequence. More recently, I was introduced to a VC with 10-figures under management. Surprisingly, he felt he lacked gravitas and wanted to learn it from someone who already had it. That's not how gravitas works. In both ca
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The best coaches do one thing most coaches don't even know is possible.
Smart money listens, challenges, and supports. It doesn't dictate. Great coaches aren't different. We listen deeply. We ask hard questions. We confront and push to unearth what's already inside and then hold founders accountable to their genius.
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Doomscrolling won’t save you. Here’s what will.
This past weekend, I joined 150 friends in a Zoom and we wrote letters to voters in swing states… Wildfires, police killings, an incurable virus, disinformation and propaganda, racism, blatant disregard for the constitution and even democracy itself… It’s pretty easy to get real hopeless, real fast these days. But complacency plays into the hands of the incompetent administration. They need you to lose confidence in democratic processes. Screw that. Here are 3 things I’m doing that are giving m
Read moreITP at 40: Red Burns Created a Program You’ve Probably Never Heard of to Save Technology’s Soul
NYU’s Interactive Telecommunications Program turned 40 this past weekend. I graduated from ITP right before the dot com bust. I was a kid… Red’s old roost. She was bold, opinionated and tough as nails. Visiting here was both terrifying and inspiring. NYU’s Interactive Telecommunications Program turned 40 this past weekend. I graduated from ITP right before the dot com bust. I was a kid, but we worked, played and created so hard, it feels like yesterday. ITP just moved to a great new space in B
Read moreThe best CEO playbook is the one you write
Spoiler alert: There’s no playbook. But Jerry Colonna’s new book, “Reboot: Leadership and the Art of Growing Up,” comes close. In it, he… Spoiler alert: There’s no playbook. But Jerry Colonna’s new book, “Reboot: Leadership and the Art of Growing Up,” comes close. In it, he invites founders to cut through the BS and connect with the person behind the persona. The book proposes that self-inquiry and personal responsibility will create a meaningful foundation and give founders their best shot at
Read moreOne week in…
Last week, I wrote that I’m hopeful about America’s future because my friends, family and regular folks are more engaged than I’ve seen… Last week, I wrote that I’m hopeful about America’s future because my friends, family and regular folks are more engaged than I’ve seen them in my adult life. I still am, here’s a nice example of what I mean, from a friend in an email group: Now, I’m aware it’s not all sweetness and light right now. We’ve started barring refugees and requiring religious tests
Read moreBack to the Future
History doesn’t repeat itself but it often rhymes As crazy as our new president and our time feels today, as high as the stakes are, I have hope. I have hope because Americans are more engaged and more informed than I’ve seen them in two decades. 16 years ago, on January 20th, 2001, I joined artists, activists and citizen journalists on a rainy day in DC to protest the inauguration of George W. Bush. At best, it appeared to us that our country had “jumped the shark,” at worst, some felt we had
Read moreI promise to be embarrassed today
When I sat down last week to write out my goals for the year, the most audacious goals I could think of weren’t career accomplishments… When I sat down last week to write out my goals for the year, the most audacious goals I could think of weren’t career accomplishments. Instead, they were all related to personal growth. The scariest metric I could think of to track them was embarrassment. Fear has long been a compass for me. I learned the hard way, too many times, that running away is more pa
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