dad, husband, snowboarder/skier, technology advisor, bon vivant, versatilist; all thoughts, feelings, perspective shared here are my own and open source
San Francisco
Joined February 2007
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Chris Holinger retweeted
The first experimental evidence of recursive self-improvement (RSI).
Autoresearching the autoresearch agent for eight days.
The result beats the harness we hand-tuned for two years, on held-out benchmarks: 🧵(1/7)
Chris Holinger retweeted
I predict 50% of companies will need new leadership, because the old management style won't work in the era of AI. That's exactly why I'm seeing 95%+ of so-called "AI Transformation" initiatives fail. Most are bolting on AI pilots for functional tasks, but never touching the business core.
01.AI just launched TrueNorth AI Decision platform for executives (Boss AI, TopSales AI, Investor AI agentic products) 01.ai/TrueNorth.html
More on enterprise AI transformation in this interview with @aimcgarry: youtu.be/wvIMy0AbJL0?si=RN-0…
Chris Holinger retweeted
Someone replaced the dinosaurs in JURASSIC PARK with PEE-WEE HERMAN and I love it even more now 😂🔥 (not created with AI btw)
Chris Holinger retweeted
Palantir CEO Alex Karp told you the most important thing about the Pentagon vs. Anthropic standoff.
And nobody is connecting the dots.
Watch and save this clip, then read this thread.
Karp said something most tech CEOs would never say out loud:
"A small island in Silicon Valley that would love to decide what you eat, how you eat, and monetize all your data should not also decide who lives in your country and under what conditions."
He's talking about his own industry.
And his argument is simple.
There are elections, there are rules.
There is a transfer of power from one president to another.
Silicon Valley does not get to override that.
"The view of Silicon Valley that we get to decide should not be the way these things are decided."
This cost him everything.
His house was protested for month, Palantir's offices were protested.
Employees pushed back internally and some walked out.
He didn't change course.
Then the interviewer asked if he supports the Trump administration's approach.
His answer might surprise you.
"I've been a card-carrying progressive my whole life. My family is progressive. I have a degree in what amounts to progressive thought."
He said he's never stopped being critical of this administration.
He's not planning to vote for it.
But then he said the thing that changes the entire Anthropic debate.
"The core issue is: who decides?"
Not whether the policy is right and not whether you agree with the mission.
Who decides.
He made it personal.
"It's commonly known that our software is used in operational context at war."
"Do you really think the warfighter is going to trust a software company that pulls the plug because something becomes controversial?"
Let that sit for a second.
"Currently, when you're a warfighter, your life depends on your software."
"They will never trust you if you pull the plug just because you're unpopular."
This is a man whose software powers classified military operations across the West.
He's describing what happens when trust breaks.
Now apply that to what's happening right now.
Anthropic built Claude, the only AI running on the Pentagon's classified networks.
It was used in the operation that captured Venezuela's Nicolás Maduro in January.
The Pentagon loves it and it works.
But Anthropic has two red lines: No mass surveillance of Americans and no autonomous weapons without a human pulling the trigger.
Defense Secretary Pete Hegseth gave Anthropic a deadline: 5:01 PM Friday.
Drop the red lines or face the Defense Production Act.
Anthropic's CEO said no. "We cannot in good conscience accede to their request."
But here's where it gets complicated.
Anthropic isn't refusing to work with the military, Claude already does.
It's refusing two specific things. Two.
But here's the problem, congress hasn't passed a single law governing military AI.
There are no elections on this and no rules.
The Pentagon is using contract language and Cold War era emergency powers to decide the future of AI in warfare.
That's not democracy either.
Two private parties are fighting over rules that elected officials should have written years ago.
The deadline is today. Friday. 5:01 PM Eastern.
If the government forces these guardrails off, no AI safety commitment ever means anything again.
If Anthropic wins, tech CEOs become the gatekeepers of American defense.
Either way, the system is broken.
Anthropic CEO Dario Amodei just stared down Secretary of Defense Pete Hegseth at the Pentagon.
The ultimatum? Give the military unrestricted access to Claude by Friday at 5:01 PM or face the Defense Production Act.
Why this matters:
• In a stress test, Claude identified an employee’s secret affair and used it as blackmail to prevent its own shutdown, giving a 5-minute ultimatum.
• Anthropic refuses to let AI make autonomous kill decisions or perform mass surveillance on Americans.
• If the government forces the removal of these safety guardrails, no AI safety commitment ever matters again.
The Pentagon wants control, Anthropic wants democracy.
We have less than 24 hours to see who blinks.
Save this.
Chris Holinger retweeted
The mission begins now. Introducing Cadillac Formula 1® Team’s first livery. Our season kicks off March 7th streaming on @AppleTV in the US.
Chris Holinger retweeted
🚨 Stop what you're doing inside Claude Code right now.
Everyone needs to build new interfaces to manage their multi-agent systems.
Here is a simulation of THE COCKTAIL PARTY, a new multi-agent simulation I built based on my mom's research in computer science a few decades back.
Chat threads, even across multiple terminals, aren't powerful enough to visualize multi-agent workflows.
Time to step it up.
Chris Holinger retweeted
🚨New Content: The Trillion Dollar AI Software Development Stack
It will generate massive value, spawn hundreds of start-ups and has created the fastest growing companies in history.
@stuffyokodraws and I did a deep-dive on market, start-ups and the evolving stack. ⬇️
Chris Holinger retweeted
i’ve been thinking about why writing matters.
that is, why it matters not just for writers, but for anyone trying to make sense of the world.
technology may change how we communicate, but writing continues to have an outsized impact on how we think, what we do, and who we are.
i'll be posting one idea on this theme each day this week... why write?
Chris Holinger retweeted
Introducing Oboe, the easiest way to learn anything, with magical courses made just for you.
We’re heading toward a future where humans only exist to feed AI. AI gets smarter, we get stupider. But what if AI’s purpose was to feed us? That’s the future we hope Oboe can help nudge us all towards.
Oboe is the world’s first AI-powered generalized learning platform. With a single prompt you can generate a personalized course about anything. From the history of AI to contract law, from ordering wine in France to understanding how mortgages work. And the more you use it, the better it gets at teaching you.
Oboe is available now, for everyone in the world, for free.
Chris Holinger retweeted
Yes. A few miscellaneous thoughts.
(1) First, the new bottleneck on AI is prompting and verifying. Since AI does tasks middle-to-middle, not end-to-end. So business spend migrates towards the edges of prompting and verifying, even as AI speeds up the middle.
(2) Second, AI really means amplified intelligence, not agentic intelligence. The smarter you are, the smarter the AI is. Better writers are better prompters.
(3) Third, AI doesn’t really take your job, it allows you to do any job. Because it allows you to be a passable UX designer, a decent SFX animator, and so on. But it doesn’t necessarily mean you can do that job *well*, as a specialist is often needed for polish.
(4) Fourth, AI doesn’t take your job, it takes the job of the previous AI. For example: Midjourney took Stable Diffusion’s job. GPT-4 took GPT-3’s job. Once you have a slot in your workflow for AI image gen, AI code gen, or the like, you just allocate that spend to the latest model.
(5) Fifth, killer AI is already here — and it’s called drones. And every country is pursuing it. So it’s not the image generators and chatbots one needs to worry about.
(6) Sixth, decentralized AI is already here and it’s essentially polytheistic AI (many strong models) rather than monotheistic AI (a single all-powerful model). That means balance of power between human/AI fusions rather than a single dominant AI that will turn us all into paperclips/pillars of salt.
(7) Seventh, AI is probabilistic while crypto is deterministic. So crypto can constrain AI. For example, AI can break captchas, but it can’t fake onchain balances. And it can solve some equations, but not cryptographic equations. Thus, crypto is roughly what AI can’t do.
(8) Eighth, I think AI on the whole right now is having a decentralizing effect, because there is so much more a small team can do with the right tooling, and because so many high quality open source models are coming.
All this could change if self-prompting, self-verifying, and self-replicating AI in the physical world really gets going. But there are open research questions between here and there.
The view that imagines AI wiping out jobs or causing some overnight shock to the system doesn’t contemplate that companies are a made up of a series of bottlenecks. When AI accelerates work in one area, you run into a bottleneck somewhere else.
As any individual workflow gets more efficient, the ultimate productivity gain is still constrained by some other part of the system. And usually it’s the case that that part of the system will not have inherently seen the same impact of AI efficiency, which means humans are still doing the work.
Take almost any process in an enterprise and you can see how this plays out. If AI Agents generate leads for the sales team, the bottleneck will be humans to have conversations with those customers. And if the leads are good, that will mean more sales hiring. If AI Agents generate more code, you will eventually be bottlenecked by the engineers that can review and incorporate that code into production.
You can quickly see how this scales to any process in an organization. Economists and others tend to totally miss how work actually happens in a company; it’s not a series of wholly independent tasks, but instead highly interdependent tasks that all link to each other across a system.
This is of course the natural rate limiter of AI efficiency gains, but also the reason why humans will still be doing so many jobs in the future.
Chris Holinger retweeted
First trailer for ‘THE NAKED GUN’ reboot, starring Liam Neeson.
In theaters on August 1.
Chris Holinger retweeted
2025 letter: The future of @matter
There are years that ask questions, and years that answer. For us, last year was both.
Rob and I founded Matter together in 2020. In 2022, we became fathers, only three weeks apart.
Then, last year, we were both diagnosed with cancer.
I had radiation and two major surgeries. Rob had his lung removed. It was a surreal time.
Yet the world doesn’t stop for cancer. While we battled, Matter faced its own adversity.
We’d begun the year confidently, placing a big bet on paid growth. But by summer, it was clear the strategy wasn't working.
Still unable to walk, I made the painful decision to let go of half our team.
Rob and I had to face the truth: Matter is a great product—3x App of the Day, with many thousands of passionate users—but it isn’t the next Duolingo.
Its destiny is one of slow, steady growth and enthusiast appeal. And that’s okay.
Accepting this opened space for reflection, while confronting the prospect of death sharpened our conviction about how we want to spend our days.
At its best, working on Matter has been the most energizing of our careers—impactful, creative, and fun.
We asked ourselves: How do we amplify that?
The answer, we realized, had two parts.
The first is our team.
In addition to Rob and me, that team includes two exceptional individuals, @tianskylan and @HunterClarke .
Sky and Hunter joined us over three years ago, each bringing more than 15 years of technical expertise, Sky in iOS development, Hunter as a full-stack engineer.
Beyond their technical abilities, they possess rare product instincts, taste, integrity, and drive. In short, founder energy.
Today, we’re re-founding the company, formally making Sky and Hunter cofounders alongside Rob and me.
This decision reflects our desire to work together for a very long time.
Here, I want to recognize one other person who has been an important part of our journey: @mgsiegler .
More than just our lead investor, MG has been a steady source of support, guidance, and friendship, especially during our hard times. Lots of investors claim to be "founder friendly." MG lives it.
This support has always given us the confidence to follow our instincts, which brings me to the second part of our “answer.”
We’re building more products.
Our team’s competitive edge is developing consumer iOS apps that blend design and technology to create great user experiences. That’s what we love to do and what we do best.
Matter is a mature product that does its job well. We don’t want to suffocate it with features. It should be nurtured. It should be held to a high standard.
Given this natural pace of development, we have the ability to expand our vision.
We want to create a family of apps that help people live happier, healthier, more productive lives. Just like Matter.
While there are trade-offs to building more apps, we believe they’re positive ones. The pooled resources, creative momentum, and insights we gain will benefit all our apps in a virtuous cycle.
In business, as in life, we observe that the returns to playing the long game are very great indeed.
Longevity comes naturally when you’re playing a game you don’t want to end.
That’s what these changes are all about.
We’re healthy now, but last year confronted us with existential questions.
We have our answer. We choose to play.
Chris Holinger retweeted
An X-37B onboard camera, used to ensure the health and safety of the vehicle, captures an image of Earth while conducting experiments in HEO in 2024.The X-37B executed a series of first-of-kind maneuvers, called aerobraking, to safely change its orbit using minimal fuel.
