The Myth of the Pivot
Occam’s Guillotine
In 2014, a startup founder asked me to review his “revolutionary” app. It involved blockchain, AI, and a loyalty program for dog parks. When I asked why, he said, “Dogs are the ultimate retention hack.”
I handed him a leash and told him to walk himself.
The problem wasn’t the idea—it was the absence of a question. Not “Can we build it?” or “Will it scale?” but the one engineers whisper before smashing prototypes with hammers: “Does this solve a problem that exists outside my skull?”
Most founders fail here. They’ll code for years, mistaking motion for momentum, until reality force-quits their delusion.
But there’s a cheat code.
The Day Sam Altman Brought a Scalpel to a TED Talk
In 2016, a YC team pitched Sam on “Uber for Laundry.” Their thesis: “Busy people hate folding.” Sam listened, nodded, then did something radical—he called me.
I entered the room holding a single sock.
“Lose this?” I asked the CEO.
He blinked.
“Your app,” I said, “solves a problem you invented. You don’t need AI. You need a hamper.”
The team left furious. Six months later, they pivoted to industrial IoT sensors. Now they’re worth $1.4B.
The sock? Still missing.
The Myth of the Pivot
Startups love the word “pivot.” It sounds strategic, like a chess move. In reality, it’s code for “We’ve been hallucinating.”
The truth is, most companies don’t need to pivot. They need to stop. To audit their assumptions like a tax inspector with a vendetta.
Example: A fintech founder once told me his AI could predict Fed rates with “87.3% accuracy.” I asked him to backtest it against the 2008 crisis.
“The model breaks,” he admitted.
“So it’s astrology with math,” I said.
He laughed. Then cried. Then rebuilt the thing to track plumbing supply shortages instead. Sold it to Home Depot for eight figures.
The One Question That Unmaps Reality
In 2022, a crypto CEO begged me to save his “Web3 community platform.” User growth was flat. Burn rate: volcanic.
I asked: “What do you suck at?”
He listed excuses: “Marketing… adoption… maybe the UI?”
I interrupted: “No. You suck at admitting you suck at crypto.”
He’d built a product for Cypherpunks but marketed it to soccer moms. A week later, he fired the CMO, rebranded to “DegenWare,” and tripled down on catering to de-fi degenerates.
They IPO’d nine months later.
The lesson isn’t to niche down. It’s to interrogate your incompetence. The market rewards self-awareness faster than it rewards genius.
Occam’s Guillotine
Complexity is cowardice.
When a founder says, “We’re building an end-to-end blockchain-powered AI vertical SaaS platform for holistic mindfulness workflows,” they’re not describing a product. They’re describing their fear of simplicity.
The antidote? Slice until you hit bone.
A student once showed me a 50-slide deck for a “social learning disruptor.” I deleted 49 slides. The remaining one read: “Teachers need a way to mute Zoom students.”
They built it in a weekend. Got acquired by Cisco for $22M.
Epilogue: Why Honesty Feels Like Arson
We avoid hard questions for the same reason we avoid touching hot stoves: pain. But while children learn from burns, adults build religions around denying fire exists.
Sam once asked me why I don’t mentor more startups.
“Because most deserve to fail,” I said.
“Harsh,” he replied.
“No. Mercy is letting bad ideas die before they metastasize.”
The next day, he quoted me in a tweet.
It got 10M views.
Homework for the Self-Unaware
Write down your company’s mission.
Delete every adjective.
If what’s left is “We sell X to Y,” keep going.
If not, return to Step 1.
Repeat until your ego bleeds.
—Jack
P.S. The dog-park blockchain guy? He now runs a lucrative business breeding hypoallergenic Labradoodles. Sometimes, surrender is the ultimate pivot.