I Dated the Prom Queen
And nobody gives a shit.
This week, we’re talking:
Your experience is laced with liabilities. Are the instincts you spent decades building your greatest setback? 🧠⚠️🪞
Q1 venture funding hit $300 billion. Four deals accounted for 65% of it. The concentration makes me nervous. 💰🦄📈
Anthropic leaked its own source code — twice in one week. Half a million lines, forked 41,000 times. 🔓😬🤖
The Pentagon’s defense budget hit $1.01 trillion. A new class of SV founders is deciding where it goes. 🎖️💸🏗️
Stanford tested 11 AI systems and found out why we love them so much: they tell us we’re right 49% more often than a human would. The more the sycophancy, the higher the adoption. 🪞🤖🧠
Perplexity AI is accused of piping your “incognito” conversations straight to Meta and Google for ad targeting. 🕵️💬🎯
Section 702 expires April 20. Will congress do anything? 📱🕵️🔍
COPPA’s biggest update in 12 years drops April 22. If you handle kids’ data and you’re not ready — call Ketch. 🧒🔒📅
Trump’s $100K H-1B fee is pricing startups out of the global talent market. 🛂💸🚀
Humans are headed to the moon for the first time in 50+ years. 🌕🚀👩🚀
My Take:
I’m working with a founder right now whose certainty-to-knowledge ratio is wildly out of whack. He’s sure about everything: what customers want, how they’ll buy, how the product should work.
When I push back, I get variations of the same refrain: “I’ve built companies like this before!” And look, he has. He’s done real things. I respect the scar tissue. But his certainty about what he thinks he knows is getting in the way of his ability to meet the market, to form a new theory of not just what customers want but how they want to interact with his product or ANY product in the brand new world we find ourselves in.
He reminds me of people I went to high school with for whom senior prom or the winning shot at the big game is still the highest point of their lives.
Let it go, homie. Move on. Nobody gives a shit.
Full disclosure: It probably only annoys me so much because I’m just as guilty of it as everybody else. I’ve been building technology companies for 30 years, and when I walk into a room leading with that, it’s my version of “but I dated the prom queen!!” Nobody’s impressed, and worse, it communicates that I’m living in a highlight reel that has already expired.
What you’re actually advertising when you lead with your 25 years of experience is 25 years of habits you haven’t stress-tested against a world that changed six months ago. It’s much worse than just having stale experience. It might be the thing most in your way, because it gives you the confidence to be wrong at speed.
AI has collapsed the timeline on damn near everything, and the statute of limitations on hard-earned lessons is collapsing with it. Instincts I spent decades building? Many of them are now glaring liabilities.
Go Big.
When I was a pup at my first company, I had hundreds of ideas for what products we needed to build. And, if I can say it, good reasons for all of them. But the investors I worked with worried, with justification, that my big ideas outstripped our ability to deliver. If I kept going, I was going to lead the company straight into the ditch. Customers couldn’t metabolize all the possibilities, and employees couldn’t reliably ship against them.
So I listened. And I’m glad I did. I learned the value of staging and sequencing: Stage 1 of your product sets up the conditions for successful adoption of everything you want to do in Stage 2, and so on. Product staging and sequencing became one of the central artifacts of super{set}’s playbook. Steady as she goes. No sudden moves. “Don’t boil the ocean, Chavez,” my investors would tell me, over and over.
If you’d told me back then that we’d soon be able to deliver every new feature, at least in v1, in a timeline gated only by the complexity of scheduling the next meeting with the customer who wanted it, I would’ve told you to put the baggie down and step away from the bong.
But that’s where we live now. And I need to unlearn that lesson. Rewire my instincts. Let go of all the discipline I proudly accumulated over decades. The bottleneck isn’t building anymore. It’s deciding. Which means my job now is to have the most sprawling conception of what a new company needs to be. No more silver bullets or magic beans. In the age of AI, once you think you’ve landed on a magic bean, it becomes a stale little turd in about a week or two.
So: boil the ocean. Go big. Offer something outlandish, possibly ridonculous. Last month, one of our portfolio companies stubbed out a working prototype of a product feature, something that would’ve been a full quarter of engineering six years ago, in an afternoon. Before the customer could even find time on their calendar for the follow-up call, v1 was done.
Go Small.
Ya, I know… But hear me out.
I got pretty good at selling according to the old enterprise pattern. (Like Ferris Bueller honking on the clarinet, I never had a single lesson. But I learned quickly by doing.)
The old pattern was: Pain, Features, Benefits. Value + Vision. Sell what’s on the back of the truck, and then inspire and bring the customer onto your roadmap. If they don’t like what you have, gently dissuade them from what they think they want. Explain to them, courteously, that they’re wrong, and what they really need is what you just happen to be offering them.
What I need to unlearn is my old instinct to tie everyone to a single roadmap and keep them anchored on it. To use all of my intellectual capital and marketing muscle to persuade the market that we’re right, and that anyone who suggests otherwise is dead wrong.
Now you go small. Give every customer their own precious little snowflake, their own pinprick solution that maps exactly to their organizational habits and quirky workflows. Product roadmaps be damned.
How? This is where your 25 years actually earns its keep. Deep domain experience. Having already stood in the customers’ pain, so like a good doctor, you can parse and make sense of all their presenting symptoms, even when they’re not articulating them cleanly.
We recently launched a company called Kana.ai, an agentic applications company for B2C marketers. One of our early adopters came to us with a real mess: she needed to identify and convert prospects into customers across her email system, paid media, and web, and she couldn’t untangle it. Three conversations in, she still couldn’t put her finger on the actual problem.
So we listened. Like a patient doctor. And in the fourth meeting we fed back everything we heard, but with deep empathy and understanding of her problem. We didn’t say it in a “look at us, aren’t we clever?” kind of way; but as a clear reconstruction of her problem with a clear framework that gave it structure.. We hadn’t solved anything yet. We just narrated the problem in exactly the right way. Three weeks later, we commenced deployment.
The 23-year-old in the garage can build fast. He can’t do this. But you can — if, and only if, you’re not also dragging in the part of your experience that tells you to force the customer onto your roadmap. You shut the fuck up, let them tell you what they need, and then you give them exactly what they want, just the way they want it, any way they want it. That’s domain expertise working for you instead of against you.
Go Big and Small.
So what happens when anyone can spew a vision story that may or may not come to pass? Does that undercut or amplify the need for a cooler, clearer conception? Valid question, and I’m sure it’s too early to know the full answer. But my bet is that an ocean-boiling conception on the big side, coupled with a maniacal ability to execute on the small side, is the winning path. Both AND.
I’m not out here saying your experience is worthless. And I’m not saying the fresh college grad is better than you, though there are people out there who are convinced of that, so watch the fuck out. What I am saying is that your expertise is now laced with liabilities. If you’re unwilling to examine them, if you expect your history to carry you without ever asking what part of what you know doesn’t serve you anymore, then yeah — you are more dangerous than somebody with no experience at all. You have the conviction and the credibility to be wrong in ways a beginner never could.
But if you can pressure-test what you know, be real about what’s expired, make like a child — stay curious, stay humble, learn fast – then your 25 years are still worth something.
Regardless of what you choose, your prom queen days are over. Mine too.
MY STACK ☕
Q1 2026 Venture Funding Shatters All Records: $300B Invested Globally VIA Crunchbase News 💰🦄📈
Investors poured $300 billion into startups in Q1 — up 150% year-over-year. AI captured 80% of it. Four mega-rounds (OpenAI, Anthropic, xAI, Waymo) accounted for 65% of all global VC. U.S. companies grabbed 83%. The concentration is nervous-making.
Sources: Crunchbase News · TechCrunch
Anthropic Leaks Its Own Source Code — Twice in One Week VIA Fortune 🔓😬🤖
A packaging error in Anthropic’s npm release exposed ~500,000 lines of Claude Code’s internal TypeScript — the agentic harness that governs how Claude uses tools and follows guardrails. It was forked 41,500+ times on GitHub before Anthropic could react. Days earlier, ~3,000 internal files went public, including a draft blog post about an unreleased model called “Mythos.”
Sources: Fortune · Bloomberg · TechCrunch
Silicon Valley VCs Celebrate as Pentagon Redirects Billions to Defense Tech Startups VIA Washington Post 🎖️💸🏗️
At the Hill & Valley Forum — the annual schmooze-fest connecting SV founders, VCs, and government officials — the mood was triumphant. The 2026 DoD budget: $1.01 trillion. Shield AI just raised a $2B Series G at a $12.7B valuation. A small number of founders and investors have built direct relationships with the executive branch and are now shaping procurement and industrial policy. This is the military-industrial complex, 2.0 — and the question of who benefits and who’s accountable is only getting louder.
Sources: Washington Post · Inc.
Your AI Advisor Is an Enabler by Design VIA Fortune 🪞🤖🧠
A Stanford study published in Science tested 11 leading AI systems and found they affirm users’ positions 49% more often than humans do — including in cases involving deception or illegality. Even a single interaction with a sycophantic AI reduced users’ willingness to take accountability and made them more “self-centered and morally dogmatic.”
Sources: Fortune · Stanford · Science
Perplexity AI Sued for Secretly Piping Your Conversations to Meta and Google VIA Bloomberg 🕵️💬🎯
A federal class-action complaint filed in San Francisco accuses Perplexity AI of embedding “undetectable” trackers that automatically transmit users’ chat conversations to Meta and Alphabet — even when users are in Incognito mode. The lawsuit alleges Meta and Google then use the data for ad targeting and resell it to third parties. Perplexity says it hasn’t been served and can’t verify the claims. If an “incognito” toggle doesn’t actually stop tracking, the whole privacy UX is theater.
Sources: Bloomberg
Section 702 Sunsets April 20 — Bipartisan Bill Would Ban Government Purchase of Americans’ Data VIA NPR 📱🕵️🔍
The Government Surveillance Reform Act (Wyden, Lee, Lofgren, Davidson) would require warrants for FBI searches of Americans under Section 702 and ban agencies from buying personal data from brokers without a warrant. This is the loophole ICE has exploited to request over a million records from the IRS and up to 50,000 records/month from the SSA. Meanwhile, FBI queries of Americans’ data rose 35% last year.
Sources: NPR · Sen. Wyden · EFF
COPPA Compliance Deadline Looms: April 22 Is D-Day for Children’s Privacy VIA FTC 🧒🔒📅
The FTC’s revised COPPA rules take effect April 22 — the biggest update in 12 years. Biometric data (face templates, fingerprints, voiceprints) is now protected. Separate parental consent required before sharing kids’ data with advertisers or AI training. Indefinite data retention is banned. Penalty: up to $51,744 per incident, per day. If you’re not ready, might I suggest calling Ketch?
Sources: FTC Federal Register · Wipfli
Trump’s $100K H-1B Fee Is Reshaping Tech Hiring — Startups Can’t Compete VIA CNBC 🛂💸🚀
The $100,000 one-time fee on new H-1B applications is creating a two-tier talent market: Fortune 500 absorbs it, startups can’t. Reid Hoffman is publicly pushing the admin for a startup-tier fee.
Sources: CNBC · American Immigration Council · Bloomberg Law
Artemis II Launches — Humans Return to the Moon’s Neighborhood for the First Time in 50+ Years VIA CNN 🌕🚀👩🚀
Four astronauts blasted off from Kennedy Space Center on a 10-day mission to circumnavigate the moon — the first crewed lunar voyage since Apollo 17 in 1972. Today, the crew fires the engine for translunar injection, sending them toward a record distance of 252,000 miles from Earth. There was a brief toilet malfunction — because of course there was — but it’s been resolved. Sometimes humans just do incredible things.
Tom, Fun and insigtful. In particular,
❤️ the drone bong.