Built & sold a 9-figure SaaS company. Operator turned investor. Finding alpha through talent & culture.

Omaha, NE USA
Joined March 2009
Anthropic filed its S-1 this morning. Everyone's reading the revenue line and the $80.7B H1 loss. I'm reading it as an operator. This is a talent document. 🧵
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4/ Their argument for why it works: broad employee stock ownership. People are codifying their own jobs into Claude, and they get a stake in the upside for doing it. That bargain is great when the stock goes up and painful when it doesn't.
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5/ So my diligence question isn't "can they grow revenue." It's what keeps the top 200 people around after the lockup, once they're wealthy and the agents do half their old job. Mission? Equity refresh? Culture?
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When was the last time we heard the word “integrity” in a political campaign? Have we given up on the idea that integrity matters?
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Greg Harris retweeted
He came back for these moments 🙌
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Greg Harris retweeted
“AI is going to make dumb people dumber and smart people smarter.” - @thedankoe
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Greg Harris retweeted
AI agents are now more than twice as accurate at medical diagnosis than average human doctors
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Here’s a thought as I reflect on two uncomfortable current events—turbulence in stock prices and a mid term election. We’re watching some of the wealthiest companies in history spend hundreds of billions of dollars building the infrastructure for artificial intelligence. In some cases, they’re committing all their free cash flow to the effort. Wall Street understandably worries about the returns on that investment. For decades, we’ve debated whether big corporations and their wealthy shareholders contribute enough to society. And half the country seems to raise a fist demanding the wealthy pay more. What if we viewed this massive AI infrastructure buildout as this exact kind of societal contribution? These companies are financing the infrastructure that is democratizing intelligence. Anyone with an internet connection can access capabilities that were once reserved for people who could afford lawyers, consultants, tutors, researchers, and personal assistants. Think about the implications for a student, a small-business owner, a job seeker, or someone trying to navigate a complicated legal question. The societal value being created is extraordinary, and much of it will never appear on the financial statements of the companies funding it. But there’s something remarkable about private companies taking enormous financial risks to build infrastructure that benefit billions of people. History is full of infrastructure revolutions where society ultimately captured more value than the original investors. AI will be another. So as the market punishes these companies for spending too aggressively, here’s one consolation: Wealthy companies and investors are taking on a buildout that would look staggering even for large governments—and humanity will emerge immeasurably richer.
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Am I a bad person if I get annoyed and want to correct someone for pronouncing “euro” like “giro”?
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Greg Harris retweeted
Emotional moment at a Pennsylvania high school yesterday after a student crowned Homecoming King surprised everyone by passing the honor to the runner-up.
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How much did the Iran war cost your investment portfolio today?
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Anxiety is part of being alive, especially when you're doing things that are difficult, unfamiliar, or important to you. The goal isn't to get rid of anxiety altogether. It's to learn how to accept it, understand what's causing it, and approach the things that make you anxious as opportunities for adventure rather than something to avoid. As Kierkegaard put it, anxiety is “the dizziness of freedom.” Freedom comes with uncertainty, and that's a price worth paying for a life fully lived.
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Cavemen Issues Dire Warning That The Wheel Is Going To Eliminate Countless Jobs
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Given today’s release of Anthropic numbers, this post from September is more interesting.
What if Anthropic’s slowing down of the frontier and OpenAI statement that they aren’t doing IPO this year are actually a response to decelerating growth rates in Q3?
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I don’t think Gillis haters understand how social media algos work. All the SNL reaction has his clips being viewed orders of magnitude more than normal weeks. You took the bait.
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The US stock market has never been this fragmented: The 52-week correlation between the equal-weighted S&P 500 and the S&P 500 index is down to 0.67, its lowest level on record. This measures how closely the performance of the equal-weighted S&P 500 tracks the cap-weighted index, with a lower reading indicating a growing gap between the broader market and mega-cap stocks. The correlation has declined -0.25 points since August 2025. By comparison, before the 2020 pandemic, this figure remained between 0.95 and 0.99 for nearly 15 years. To put this into perspective, during the 2000 Dot-Com Bubble, this metric never declined below 0.85. The S&P 500 is more concentrated than ever.
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This is me with ALL beer.
Mark Zuckerberg pretending to enjoy Guinness is my new favourite thing.
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