A few weeks ago, we watched HBO’s new movie Mountainhead. If you haven’t seen it, I won’t spoil it, but imagine a cinematic smash-up of the All-In Podcast and peak tech-bro delusion. It’s satire. It’s messy. It’s a great Saturday evening watch.
But one line stuck out:
“The whole of history operates on the ‘Fuck! What? Cool!’ principle.”
That line is the cleanest description of product adoption I’ve ever heard. Better than any S-curve diagram, diffusion of innovation chart, or MBA case study.
And once I saw it, I couldn’t unsee it.
Every Great Startup Has a “Fuck!” Moment
You know the feeling.
The pitch is confusing.
The founder sounds slightly unhinged.
Your brain short-circuits trying to decide if what the founder is building is brilliant or dangerous.
That’s the “Fuck!” stage.
It’s the moment a new idea collides with your existing model of the world. And breaks it. And that moment is where the best companies often start. Before there's data. Before there's proof. Just energy. Vision. Maybe delusion.
This is the point where most people step back.
Then Comes “What?”
Once the panic fades, curiosity sets in.
You start asking better questions.
You see early adopters doing surprising things with the product.
Communities form. Not just customers, but believers.
Now there’s something to pattern match against.
It’s not obvious yet, but it’s no longer crazy. You’re in the messy middle. Trying to connect the dots while the product evolves in real time. It doesn’t fit cleanly in a category. But it’s working. Kind of. Sometimes.
It’s the stage where smart people start saying, “Okay… what is this really?”
And Eventually, It’s Just… “Cool.”
By the time a product hits “Cool,” it’s probably already a verb.
You don’t question whether to use it. You just do.
The UI gets copied. The pricing model becomes a standard.
Investors are circling. Analysts are writing trend reports.
Your mom brings it up at brunch.
And by then?
The alpha’s gone.
It’s safe. But it’s done. The early weirdness, the beautiful, risky part, is long past.
What This Looks Like Right Now, With AI
Today, I think we’re watching all three stages happen at once, just in different layers.
ChatGPT, Claude, Gemini - firmly in “Cool.” These are everywhere now. Parents use them to plan trips, kids are writing book reports, and they’re quietly embedded in half the tools we use daily. They’ve crossed into infrastructure.
Vertical copilots (legal, ag, healthcare) - squarely in “What?” People are testing, poking, trying to figure out what’s real. There’s traction, but also trust issues, UX weirdness, and lots of duct tape holding it together.
Autonomous agents, decision loops, AI that acts without asking - 100% “Fuck!” territory. Systems that act on their own—no clicks, no prompts, no approvals.
Bots rebalancing your portfolio, routing trucks, negotiating contracts.
Or eventually: driving your kids to school, managing your calendar, running your irrigation schedule without permission.
This is the part that freaks people out. It challenges assumptions. It forces the question: Who’s really in control here?
And like always, the most misunderstood layer is probably the one with the most upside.
As Investors, Where Are We Willing to Sit?
Everyone says they want to invest at the earliest stage. That they want to find things before they’re obvious. That they want “alpha.” That’s what we’re chasing because that’s where the most upside is.
But when we’re faced with a true “Fuck!” moment, when the founder has no metrics, the product has no market, and the risk feels existential, it’s really easy to pass.
Because that stage isn’t comfortable. It requires conviction, not consensus. Belief, not a benchmark.
To underwrite chaos. To bet on the person when the product barely exists.
So How Do You Get Comfortable at “Fuck!”?
Here’s the thing: I don’t think you can. That’s not the goal.
“Fuck!” stage investing isn’t about certainty. It’s about curiosity and conviction. The trick is learning to navigate uncertainty without letting it paralyze you.
But there are a few things I think as investors we can do to help separate signal from chaos:
1. Founder Obsession
I’m not looking for polish. I’m listening for internal logic. I often tell founders it doesn't matter if your pitch deck is pretty.
Can this person walk me through the market, the product, the friction, in a way that reflects deep thought, not just pitch deck rehearse?
Do they see something others don’t?
2. Velocity of Learning
I think it’s less vital what they’ve built, and more about how quickly they’re improving it.
Do they test fast? Are they adjusting based on real feedback from potential customers not theoretical plans?
Are they learning faster than their competition is scaling?
3. Strange Gravity
There’s often a kind of pull around early-stage outliers.
Weirdly talented hires. Ability to get their foot in the door where others can't. Pilots with skeptical customers who shouldn't say yes, but do.
Are people showing up early because they feel this might actually be something?
4. Industry Calls & Gut Checks
This part is simple but powerful: It’s critical to talk to people who would know.
Not always customers. Sometimes engineers, operators, ex-founders, researchers.
I ask: “If this works, is it meaningful?” And then: “Why wouldn’t it work?”
If their answer is a vague “I don’t know, it just feels unlikely,” and they can’t name a real technical or structural reason it will fail…That’s often enough cause to lean in. Experts are often so used to doing things a certain way, it’s sometimes hard to think outside the box.
When smart people can’t explain why it won’t work, that’s interesting.
You don’t need unanimous belief. You just need a few credible voices who don’t dismiss it outright, and can’t give you a good reason to.
You can’t be looking for clean answers in the “Fuck!” stage. They don’t exist.
But, momentum. Curiosity. Founder obsession.
And enough smart people who, when pressed, say: “…honestly, if they pull it off, it’s game over.”
That’s usually something worth betting on.
So Here's My Point
If your product doesn’t start with a “Fuck!” …it probably won’t end with a “Cool.”
That’s where the interesting stuff lives. And it always has.
I love this so much!