
Jay Sebben
5K posts

Jay Sebben
@jaysebben
CEO of L Street Corp, a growing Chicago based evergreen and diversified holding company. Buy-Build-Invest. 25+ yrs of entrepreneurial finance & SMB strategy.


Hang on… Chicago wants to attract more tourists. It has created a marketing campaign to do that; and, in order to fund it, the city is… making it more expensive to stay in Chicago by raising taxes on hotel rooms? Do I have that right?

"OpenClaw is the new computer." — Jensen Huang This is the early PC era all over again. A few power users see it. Everyone else hasn't even started. "It's the most popular open source project in the history of humanity, and it did so in just a few weeks. It exceeded what Linux did in 30 years." A solo founder with OpenClaw can now build what used to take a 50-person team. The leverage is absurd.

$11.3 billion on war for Iran, but tell me again how we don’t have enough money for health care.

100 years of Democratic governance leads Crains to seriously propose the City of Chicago consider going into bankruptcy. This would mean pension cuts, labor cuts, and millions in private contracts torn up. It would be another low point for a great City.



Section 6001 of the Affordable Care Act banned the construction and expansion of physician-owned hospitals. The American Hospital Association lobbied for it. Physician-owned hospitals consistently rank among the highest quality facilities in the country. They have lower prices. They have better outcomes. Patient satisfaction scores are higher. Medicare and Medicaid (CMS) data confirms this every year. The ban has nothing to do with quality. It has everything to do with competition. Large hospital systems couldn’t outperform physician-owned hospitals, so they made them illegal. There is no polite way to say this: Congress banned the best option to protect the worst operators in the market.


Chicago has a public school with space for 912 kids, yet only 28 students are enrolled. The school is 97% empty. It spends $93,787 per student. It's staff to student ratio is 1:1. ZERO of the kids are proficient in reading.

A company with $24 billion in revenue and 24% gross profit growth just cut 4,000 people while raising 2026 guidance to $12.2 billion in gross profit. Stock ripped 20% after hours. The market added roughly $6 billion in market cap. That's ~$1.5 million in enterprise value created per eliminated role. Block is the canary in the coal mine. And they're not alone. ASML cut 1,700 jobs last month while reporting record orders and said they were "choosing to make these changes at a moment of strength." Salesforce cut 5,000 after AI agents started handling 50% of customer interactions. Amazon cut 16,000 in January on top of 14,000 in October. Every one of these companies was growing when they did it. Dorsey said the quiet part out loud: intelligence tools paired with smaller teams have already changed what it means to run a company. He chose one massive cut over repeated rounds because, his words, gradual cuts destroy morale and trust. The restructuring charges are $450-500 million. At the operating income Block is guiding, that pays for itself in two quarters. After that, pure margin expansion. That's why Wall Street rewarded it instantly. Here's what's coming. Goldman estimates AI is already responsible for 5,000 to 10,000 net monthly job losses in exposed U.S. industries. Citigroup is planning 20,000 cuts. Dow just slashed 4,500. 40% of employers surveyed say they expect to reduce headcount because of AI. 30,700 tech jobs gone in the first six weeks of 2026 alone. Block went from 10,000 to 6,000 while growing revenue and raising guidance. Every CEO running a company with more than a few thousand employees is doing this math tonight. The canary just stopped singing.

This is a great summary of the "sucker's paradox." Honesty is not a winning strategy. We see this in healthcare, where dense rulemaking combines with means-tested exceptions, discretionary enforcement, and leniency for hardship. Each of those elements is defensible on its own. We want standardized payments so hospitals cannot charge wildly different amounts for similar care. We want adjustments for sicker patients so institutions are not penalized for taking on complex cases. We want compassion in enforcement because real lives are affected. Yet when these components are layered together, they create a predictable outcome: the honest actor is penalized relative to the strategic actor. Just look at the massive amount of Medicaid fraud being uncovered. These programs are meant to help those who have hardship. Yet, we are seeing that any system that relies on intricate rules, targeted benefits, and discretionary enforcement will tend to reward those who master classification. We did not set out to build dishonest institutions. The intent was to design systems that were fair, standardized, and resistant to abuse. Yet when payment depends on ever more granular distinctions, and when enforcement can never be perfect, behavior adapts. See more in my latest below:

Sens Josh Hawley and Elizabeth Warren Introduce “Break Up Big Medicine Act” to Force Separation of Insurers, PBMs and Providers open.substack.com/pub/healthcare…










