Jay Sebben

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Jay Sebben

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.

Chicago, IL Katılım Aralık 2011
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Jay Sebben
Jay Sebben@jaysebben·
"Entrepreneurship is the pursuit of opportunity beyond resources controlled." ~ Prof. Howard Stevenson, HBS entrepreneurial studies godfather This is by far and away my favorite definition of entrepreneurship. Why? Out of the gate it implies motion. The verb "pursuit" is deliberate and is the opposite of sitting and waiting for just the right moment. But by far the most important piece of that short phrase is "beyond resources controlled." This is pure gold. You won't see this as deliberately and succinctly applied in any other definition. What he is basically saying is - you need to go and do things without knowing how you are going to get there or where you are going to get the money/resources/talent/knowledge. Too many people wait for the perfect moment. Or complain they don't have the capital. That is not entrepreneurship. That's just day dreaming.
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Anvisha
Anvisha@anvisha·
We raised $7.5M to kill AI slop. Introducing Moda: the world's first design agent with taste. RT+ comment “Moda” and we’ll design your brand for FREE.
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Jordan Ross
Jordan Ross@jordan_ross_8F·
The founders who figure out OpenClaw in the next 90 days are going to look like geniuses in 2027. The problem is most agency owners don't have time to figure out the install, the security risks, where to start, or what to actually hand it first. So my team built a 48-page beginner's guide that does it for you. Inside: — The exact prompts to hand it on day one — Plain English setup for Mac and Windows — How to secure it so it doesn't burn your business down — 42 copy-paste workflows across sales, marketing, ops, and finance Your competitors are sleeping on this. Comment OPENCLAW and I'll send it.
The Startup Ideas Podcast (SIP) 🧃@startupideaspod

"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.

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Anthony DiGiorgio, DO, MHA
Anthony DiGiorgio, DO, MHA@DrDiGiorgio·
Congresswoman, We spend 20% of our GDP on healthcare. Nobody is saying we don’t have enough money for healthcare. We already spend too much on healthcare. The problem is that the money goes to administrators, third parties, fraudsters, and monopoly corporations acting as “non profits.” More money isn’t the answer. That will just continue putting us into debt so favored interest groups and scammers can keep extracting wealth from hard working americans. If you truly cared about healthcare, you’d be working to reverse the policies got us here in the first place.
Rep. Pramila Jayapal@RepJayapal

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

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Alexander Lacherbauer
Alexander Lacherbauer@lacherbauer·
Bankruptcy is the only path forward for Chicago. There is no credible way to "outgrow" the city's present situation. Step 1: Springfield pass law to allow city to file Ch. 9 bankruptcy. Step 2: City engages with unions and pension funds in good faith renegotiation of benefits and terms w/ bankruptcy now a real threat. Step 3: If negotiations fail, proceed with bankruptcy and let federal court resolve what creditors owed.
DuPage GOP@DuPageCountyGOP

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.

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Dutch Rojas
Dutch Rojas@DutchRojas·
You pay for healthcare seven times. Once through your premium. Once through your deductible. Once through Medicare payroll taxes. Once through Medicaid via state income taxes. Once through local hospital district levies. Once through charity care baked into every negotiated rate. And once through your employer’s “contribution,” which is your compensation, redirected before you see it. After all seven payments, 30 cents of every dollar still goes to administration. Other developed nations average 12%. The money isn’t missing. It’s just going somewhere else.
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John LeFevre
John LeFevre@JohnLeFevre·
The majority of kids in college right now will end up underemployed, taking jobs that do not require a college degree - unable to service student loans. Even the winners face massive headwinds in terms of long term job security. Now imagine 3+ years from now. What do you tell kids in high school today? - AI is doing school work. - AI is doing college applications. - Colleges are using AI to assess applications. - College kids are using AI to do school work, resumes, and job search. - Employers are using AI to assess applications. - Employers are using AI to reduce entry level positions. And how do you educate younger kids? It seems like the only viable path forward is teaching kids to become AI wizards and maestros, with an entrepreneurial mindset, whereby they can be a one-person company, or sell their skillset to the millions of boomer/gen x small businesses that don't have these skills.
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Darren Bailey
Darren Bailey@DarrenBaileyIL·
WOW... JB Pritzker's blind trust bought Centene stock. Then Centene got $20 BILLION in Illinois Medicaid contracts. Then Pritzker met personally with Centene executives. Then he claimed he knew nothing. The most expensive coincidence in Illinois history.
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Jay Sebben
Jay Sebben@jaysebben·
Where I grew up in Iowa, and I know this is the case across much of rural America, small town schools were often consolidated to neighboring towns as demand and populations shifted. It was both common sense and very difficult for the communities who lost their schools. Rural America accepted the changes. In the cities, the same pragmatic decisions need to be made but are not. Ultimately, to the degree Federal money is ever used to bail out these cities, rural America will pay again.
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Daniel Friedman
Daniel Friedman@DanFriedman81·
Chicago’s schools are so bad, almost nobody will send their kids to them. Despite this, the bankrupt city maintains full staffing for empty schools with lavish benefits. At a school with 27 full-time employees and 28 enrolled students, the principal is paid $171,173 per year. The per-student spending is $93k annually. Despite a 1 to 1 ratio of students to full-time staff, none of the 28 students enrolled at this school are proficient in reading. It is time to shut the Chicago public schools down.
Corey A. DeAngelis, school choice evangelist@DeAngelisCorey

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.

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SMB Attorney
SMB Attorney@SMB_Attorney·
Call me old fashioned but unless blocks was wildly inefficient with a bloated workforce doing very little (possible), I don’t think moves like this will age well. I honestly don’t think AI tools are there yet. This feels like over-exuberance that will get walked back with time.
Aakash Gupta@aakashgupta

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.

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Jay Sebben
Jay Sebben@jaysebben·
Exactly. This is the case in everything that lacks transparency and adds complexity. The same in the IRS tax code, costs of education, government licensing, etc. This is why market simplicity is a better outcome than central planning. It’s the natural undesired outcomes of bureaucracy + human fallibility.
Anthony DiGiorgio, DO, MHA@DrDiGiorgio

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:

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Jay Sebben
Jay Sebben@jaysebben·
@LarryDJonesJr This is insanity… goes fully against the concept of property rights and the notion of a Republic. You want people to stay, make it attractive for them to stay.
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🇺🇸 Larry 🇺🇸
🇺🇸 Larry 🇺🇸@LarryDJonesJr·
NYC’s socialist mayor, Zohran Mamdani, is doubling down on his previous statement that if a company leaves NY, find them and tax them anyway. Now he is saying: "We should take businesses from owners who want to leave due to the tax increases and run them for the city ourselves.” “We should actually make it illegal for them to leave. Fine them to hell." I wonder if New Yorkers are still happy with their decision. What are your thoughts?
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Codie Sanchez
Codie Sanchez@Codie_Sanchez·
how do i explain I’m the party of… I don’t trust fed agents w/ masks. I want to jail billionaires who mess w/ kids. I don’t think kids should make irreversible medical decisions. I’m pro-choice but not pro abortion. And yes, I want to keep my guns.
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Jay Sebben
Jay Sebben@jaysebben·
This has been an opportunity on the buy side for a while. We call it “zombie hunting.” Trick is getting a perhaps broad swath of owners across a messy cap table to agree to a deal. Some businesses that could survive as very normal & respectable small businesses get shut down because they wait too long to formally pursue an exit. Or the VCs and founders give up on caring, employees and customers be damned.
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Rohit Mittal
Rohit Mittal@rohitdotmittal·
some of the best founders i know are stuck running businesses they can't exit. they build a company that was in the wrong vertical, or their heart wasn't 100% in it but they still made it work, somewhat they built to $2M ARR with the promise to get to $100M ARR. the margins couldn't get to where it made sense, the growth needed for the next round just wasn't there. their customers are happy, but the company is not growing fast. and it's not just them, there's a gap between "good business" and "venture-scale business" where ~$10B in revenue is trapped. these founders are good operators and builders - the best next step is to start fresh (they can also join fast growth AI companies and have a better personal outcome) they should be opportunity maximizing and the best path to move in that direction is exit their company investors who backed the wrong market size get partial returns instead of total loss. teams get to work for companies with realistic goals and real equity value. we need more infrastructure around restructuring and small exits. this is the best way to reallocate talent and capital. the founder who built to $2M ARR might build to $50M ARR next time, with better market selection. let them try again instead of grinding it out with the wrong cap table. good founders being stuck doesn't help anyone. not even the investors.
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Jay Sebben
Jay Sebben@jaysebben·
This 👇
Ian Miles Cheong@ianmiles

Marc Andreessen: AI coding doesn’t eliminate programmers — it redefines them. The job is no longer typing code line by line, it’s orchestrating 10 coding bots in parallel, arguing with them, debugging their output, changing the spec, and pushing them toward the right result. But here’s the catch: if you don’t understand how to write code yourself, you can’t evaluate what the AI gives you. The next layer of programming isn’t writing scripts — it’s supervising AI that writes them. Today’s best programmers spend their day jumping between terminals, managing multiple coding bots, fixing mistakes, and refining instructions. The irony? You still need deep fundamentals, because without them, you won’t know when the AI is wrong. The job of the programmer has changed. Now it’s about arguing with coding bots, debugging AI-generated code, and understanding why something doesn’t work or isn’t fast enough. AI abstracts the work — but only people who truly understand code can tell if the abstraction is doing the right thing. Programmers aren’t going away — they’re becoming 10x, 100x, even 1,000x more productive. Tasks are changing, the job is changing, but humans are still overseeing the process, evaluating results, fixing errors, and making judgment calls. AI changes how we code, not who is responsible. The future programmer isn’t replaced by AI — they’re upgraded by it. You still need to learn how to write and understand code, because when the AI gets it wrong, humans are the ones who have to know why. That up-leveling of capability is the real revolution.

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Jay Sebben
Jay Sebben@jaysebben·
@BojanRadojici10 Hey well done. I’d love to see it and learn more about how you executed it.
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Bojan Radojicic
Bojan Radojicic@BojanRadojici10·
After 20 years in Excel, I finally watched an AI agent build a full model for me — end-to-end. I used Genspark and the result was insane: structure, schedules, cash flow, scenario switches… all generated, then refined with my assumptions. The biggest shift? I’m no longer stitching 20 sheets at 2 a.m. — I’m 𝗿𝗲𝘃𝗶𝗲𝘄𝗶𝗻𝗴, 𝘀𝘁𝗿𝗲𝘀𝘀-𝘁𝗲𝘀𝘁𝗶𝗻𝗴, 𝗮𝗻𝗱 𝗶𝗺𝗽𝗿𝗼𝘃𝗶𝗻𝗴 the model instead. If you want faster board-ready models: Start with a clear spec (drivers, outputs, constraints) Let AI draft the skeleton (P&L, BS, CF, links) You do the QA: tie-outs, edge cases, sensitivities Lock a repeatable prompt + data schema for next time If you want this Prompt,just drop a comment and I’ll send it to you. (Important: follow me so I can DM you!)
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