Built & sold a 9-figure SaaS company. Operator turned investor. Finding alpha through talent & culture.
Omaha, NE USA
Joined March 2009
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I had a salty discussion this week with 7 business leaders in Nebraska. It centered on ballot initiatives 440 and 441 which legalizes sports betting in the state and sets the parameters with which it will be managed. I'm opposed. But it was clear in that room that I'm in the minority. A🧵
A 2026 study from the New York Fed found that legalization increased online sportsbook spending roughly 10x and was associated with measurable deterioration in consumer credit--with disproportionate effect among younger borrowers.
But what about tax relief that comes from the state's rake? The financial model for 440 and 441 only estimates $166M in property tax relief over the next 10 years. That's only 0.3% of the property tax burden. And legalization would be transferring that $166M mostly from our 18-25 year old boys. I'd rather have that demographic buying houses and becoming property tax payers.
This is still the best thing about Halloween.
The couple isn’t scared of the pumpkin guy. They’re just deeply, personally offended that he exists and that the ride went all-in on him for 73 floors.
He’s not a ghost, not a killer, not from a commercial, not from anything. He’s “his own thing,” the skeletons are “part of it,” and every time they try to figure out the deal he just does the little dance and hits them with “any questions?” like he’s wrapping a PowerPoint. The actual scare at the end almost feels secondary to the real horror of having to sit there while your brain tries to solve a riddle with no solution.
Still the cleanest “why is this funny” sketch SNL has ever done. The longer you stare at it the dumber and better it gets
Greg Harris retweeted
Cliff Sosin on the limits of intelligence:
"Superintelligence arrived. You probably didn't notice, because it turned out to be kind of incremental.
I think we overrated intelligence, or misread what it is.
We hold a thin scatter of facts about the world, and intelligence or reasoning is whatever fills the space between them.
Where the space between the facts behaves well, this is close to godlike. Most of what matters doesn't behave like that.
The universe is mostly the emergent behavior of complex systems. Stir cream into coffee. Watch a storm build out of nothing but atmospheric temperature differences and water vapor.
You have to run the thing.
The takeoff story assumed the limit was thinking. It isn't. The limit is contact with reality.
A smarter reasoner fills the gaps between known facts in simple areas faster and better, but it doesn’t produce new facts.
An AI will hand you a genuinely clever design for a jet turbine blade. It might be far more likely to work than anything your engineers came up with.
It'll still probably fail, because that’s the base rate at the edge of what anyone knows. The only way to find out is to build the blade and try to break it.
That's the real limit on learning, and it doesn't care how smart you are. Coming up with ideas was never the hard part. The hard part is how fast reality answers them.
Most problems can't be worked out at a desk by thinking. Those stay bound by how fast we can build the thing and see if it holds, and that clock barely moves."
From his essay "Maybe Intelligence Ain't All That." He walks through it here.
Cliff Sosin (@CliffordSosin) is one of my favorite people to call, ask some big questions, and then shut up and listen.
This conversation is a version of one of those calls.
We discuss:
- The limits of intelligence
- Owning the complements to it
- Meta, the frontier labs, and the AI build-out
- Capital markets
- Why he's comfortable with 80% of his portfolio in Carvana.
TIMESTAMPS
0:00 Intro
10:41 The Limits of Intelligence
18:03 Investing Beyond Cheap Intelligence
24:03 Will AI Become Commoditized?
35:10 Who Profits From AI?
43:00 AI Agents Reshape Competition
52:06 America's Capital Markets
58:04 Transforming Companies With AI
68:19 AI and Portfolio Concentration
73:16 Education in the AI Era
I'm mesmerized by this $ANT S-1. It's the governance nuances and the talent playbook that has me captured. Is anyone talking about this Class F share that holds the 7 founders to a voting majority but vanishes if fewer than 3 remain?
🤖 Made with AI
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. 🧵
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.
When was the last time we heard the word “integrity” in a political campaign? Have we given up on the idea that integrity matters?
Greg Harris retweeted
“AI is going to make dumb people dumber and smart people smarter.”
- @thedankoe
Greg Harris retweeted
AI agents are now more than twice as accurate at medical diagnosis than average human doctors
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.