Stretch Four Insights

There’s a race to the bottom happening with AI models. The frontier ones are still expensive, but more and more it’s the application layer — the applied AI sitting on top — that’s becoming the thing worth paying for, not the models underneath. Take Rogo AI. It’s now valued at over $2 billion (a fresh $175M round), and it’s used by the banking and financial-services teams at Goldman, JPM, BofA, Wells, and Barclays — 35,000 users and growing.

Conceptually, I was supposed to be a professional basketball player. My career hit a snag on the first day of practice in college. The coach — who had just spent nine months recruiting me to my alma mater James Madison University — yelled, “Never take THAT shot again in this gym in your life.” I can’t even remember if it went in. It didn’t matter. It was a corner three off a kickout, and I was wide open. First practice. It felt like a good shot. In 2026 it would be an afterthought.

Happy Tuesday. Little bit of a hiatus — a lot happening with the companies I'm running. Sometimes content takes a back seat. But today, that's not the case. This might be the biggest single news day in a while. The news cycle is insane right now in tech, especially as it pertains to first, second, and third order effects for founders. Let's get into it. The Anthropic-Pentagon story just escalated to a new level.

Playback speed × Share post Share post at current time Share from 0:00 0:00 / 0:00 Transcript $110 Billion for OpenAI, 4,000 Jobs Gone at Block, and the $1.7 Billion Medicaid Fraud That Business Identity Could Have Caught Four Insights — Episode 005 | Saturday, February 29, 2026 Weeks are months. Months are years. Years are decades. That’s what it feels like right now in tech. The pendulum is swinging harder in both directions—and relevancy is lasting shorter and shorter amounts of time.

Playback speed × Share post Share post at current time Share from 0:00 0:00 / 0:00 Transcript Nvidia's $68 Billion Quarter, the $109 Million AI Lobbying War, and the Fintech Infrastructure Company You've Never Heard Of Four Insights — Episode 004 | February 28, 2026 Three stories dominated business this week. Each one, on its own, is worth tracking. Together, they tell you where the leverage points are in the economy right now—and who's positioning to control them.

Playback speed × Share post Share post at current time Share from 0:00 0:00 / 0:00 Transcript Stripe Could Buy PayPal for Less Than a Quarter of Its Own Valuation Workday funds the AI pivot, Stripe circles PayPal, and two engineers built what the DOJ said was impossible. Day three of the daily show.

Playback speed × Share post Share post at current time Share from 0:00 0:00 / 0:00 Transcript FIS Earnings, Anthropic vs. The Pentagon, and Why Stablecoins Are a B2B Story FIS reports $2.7B in Q4 revenue, Anthropic faces Pentagon policy friction, and stablecoins keep eating B2B payment margins. Today I've got three things: FIS earnings, Anthropic (of course) and the Pentagon, and why stablecoins are a B2B story.

Welcome to the Four Insights weekly data breakdown. Each week I’m tracking the companies, trends, and signals that matter across the ecosystems I operate in — fintech infrastructure, merchant services, lending, and AI. This is Week 9 of 2026. Let’s get into it. Four companies reporting this week that I’m watching closely, each for different reasons. FIS reports Q4 earnings tomorrow. FIS has been a pretty flat stock, but that’s not why I care about them.

I set out to read 50 books this year and made it through 23—not quite the goal, but each one left its mark. I was reviewing my highlights from the books I read this year and thought I would throw my 2025 reflections post in your timeline. Here are the key themes that emerged: The most profound insight came from : relationships aren’t passive—they atrophy without exercise. We assume friendships will always be there, waiting for us when work slows down or the kids get older or over the holidays.

I got to see one of the, if not greatest hip-hop artist of my time last night with the wife and some friends. He performed the first half of the show with the SF Symphony as Nas took over Bill Graham Auditorium — what an amazing performer that I had not seen before and also a pretty exceptional venture capitalist. He hit PillPack (Sold to Amazon for $1 billion), Ring (Sold to Amazon for $1B), Dropbox, Coinbase, and Rohinhood in what I believe was only a few funds that started around 2013.