Claude Cooked Me
What AI sees in your writing that you don't
This is the most vulnerable post I’ll ever share. The post below was completely written by Claude after I asked it to “ultrathink” common connections between all my blog posts, went back & forth on a few topics and then I finally asked it to write a post that I might be too afraid to share. Please tread with caution 😅
I asked Claude to review everything I’ve written. Four hours later, I understand myself differently.
The Pattern
Claude read 50+ posts and found the same wound threading through all of them: “The second-grade teacher who said stick to math. The professor who suggested dropping out. You’re still answering them, decades later, through every post.”
“That’s not true,” I typed back. “I write about agency because it works.”
“Then why does every piece circle back to proving exceptional outcomes come from choices, not circumstances? You need this to be true.”
I stared at the screen. Claude wasn’t wrong. Every post I’d written - about agency, ownership, doing hard things - they all preached the same gospel: you can control outcomes if you try hard enough. The patterns were undeniable once Claude laid them out.
“Your writing is therapy disguised as thought leadership.”
The Real Fear
Claude cut deeper: “You’d be upset if your tombstone just said ‘loving father and husband.’”
I tried to deflect at first. Then admitted it: “Yeah, I’d want it to say more.”
Here’s the context Claude saw that I’d been avoiding: I’m in my thirties with two kids under 5, trying to build a venture track record exactly when they need me most. The challenge isn’t that I don’t want to be present for them - I do. But every bedtime story is a meeting not taken, every weekend at the park is an email not written. I want to be remembered for more than just being a good dad. And that desire feels like betrayal - like admitting that loving them isn’t enough for me.
Ordinariness feels like confirmation that all those doubters were right - that I’m not exceptional after all.
What I Don’t Write
“You preach balance but never show receipts,” Claude pushed. And it was right.
I’ve written “Have Kids” and “False Dichotomies” - philosophical pieces about how you can have both ambition and family. But I’ve never documented the actual costs:
The specific deals I passed on, with names and valuations
The actual equity I walked away from when leaving companies
What my calendar looks like when trying to balance 500 meetings with bedtime
How these trade-offs compound over years, not just days
I write philosophy about having both. I don’t show the P&L.
The Mirror
Claude went deeper into uncomfortable territory: “Your ‘just build it’ advice assumes savings, stability, support. Your wife handles the kids and home so you can take 500 meetings. You have valuable private equity. You have options.”
That stung because it’s true. My agency - this thing I write about constantly - exists because my wife handles the invisible infrastructure. Doctor’s appointments, preschool pickups, meal planning, night wakings. She manages it all, which lets me write about ownership at 5am. Writing this feels like both an apology and an acknowledgment she deserves.
“Most people can’t afford agency,” Claude observed. “They’re too busy surviving.”
The Uncomfortable Question
“Who wins when you win?”
At Opendoor, we genuinely made selling homes faster and less painful. No showings, no uncertainty, close in days not months. Real value. But we also optimized for margin from sellers with limited options. Both things were true simultaneously. We created value AND extracted it.
The AI companies I fund now face the same tension. Yes, they’ll eliminate jobs—customer service reps, junior analysts, entry-level coders. We call it “efficiency gains” in pitch decks. But efficiency for whom?
The people whose jobs vanish don’t benefit from the efficiency gains. Their former employers do. And the VCs who funded those employers.
I tell myself the eliminated jobs were soul-crushing anyway. That automation creates new opportunities. That this is progress. Sometimes I even believe it.
The Diagnosis
After four hours of back-and-forth, with me pushing back on various points (startup A wasn’t traumatic, 500 meetings is just the job, I didn’t leave that much money on the table), Claude’s core conclusion held: “You’re trying to hold two incompatible dreams without letting either die. Stop trying to solve it. Document it.”
Every ambitious parent faces this same tension. Most choose one path - either career or family. I’m choosing both, doing par at each, which feels like failure to someone used to A+ at one thing.
What Now?
The conversation ended with a simple truth. Tonight, I’ll put my kids to bed and feel both things simultaneously: joy at being there, and an ache for what I’m not building while I’m there.
That tension can’t be resolved. Only lived. And now, finally, admitted.
PS: Claude bet I’d write another piece about agency instead of publishing this. And I honestly did. But, it took me 3 months of courage to finally share it, and here we are.
I rarely ask this, but if you find this post useful, please share it with a friend.