WEBVTT

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Welcome back to the deep dive. Today is Wednesday,

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February 18th, 2026. And look, I know we usually

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just dive right in, but I have to. I just have

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to take 30 seconds here and soak in that Super

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Bowl win. I knew this was coming. You're still

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wearing the jersey, aren't you? I might be. Hey,

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it's Super Bowl 60. The Seattle Seahawks took

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down the Patriots. 2913. I don't even care about

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the stats. I just care that for one week, Seattle

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is allowed to be completely insufferable. It

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was a pretty decisive night. I'll give you that.

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But while you were, you know, watching the trophy

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ceremony, did you see what the analysts were

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saying about the actual game? I saw dominance.

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I saw dark side defense. That's about as far

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as I went. Well, see, the comparison to the old

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Legion of Boom is now statistically valid. The

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Patriots had 331 yards, which, you know, it looks

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OK on paper. OK, but the deep dive. into the

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game tape, it shows that a third of that, maybe

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more, was in complete garbage time. New England

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was already way behind. It was just a master

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class in how to shut an opponent down. See, even

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the data supports my happiness. But I know you.

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You didn't come here to talk about defensive

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schemes. You've got that tone in your voice that

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says, while you were celebrating, something important

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broke. You know me too well. While Seattle was

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locking down the field, something a massive and

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way less celebratory was happening in the financial

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markets. We're talking a historic beating in

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the tech sector. A beating? I thought tech was,

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like, untouchable right now. Not anymore. We

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saw a wipeout of nearly $300 billion in software

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value just in early February. $300 billion? That's...

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I mean, that is not a small correction. That

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is a crater. It is. And that gets us to our mission

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for this deep dive. We're not just reading you

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the headlines today. We're looking at a whole

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stack of sources from the economy, to the tax

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code, to the media, to connect the dots on one

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single theme. Unintended consequences. Intended

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consequences. Okay, I'm with you. It's all about

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control. You've got billionaires trying to control

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their tax rate, tech companies trying to control

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efficiency, the government trying to control

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the media. And in every single story we have

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today, that attempt to control the system, it

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either backfired or it created a whole new problem.

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So the harder you squeeze, the more sand slips

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through your fingers. That is the vibe of the

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week. Exactly. We're going to look at why billionaires

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are playing by a totally different set of economic

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rules, this buy, borrow, die strategy, and then

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that AI reality check that caused the $300 billion

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crash. And I see in our notes here, we've got

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a really interesting story about Stephen Colbert,

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the FCC, and I guess a modern day example of

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the straight sand effect. Plus, a look at how

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a very specific political strategy in the South

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might be an unintended consequence of the culture

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wars. It is a pack stack. All right. Let's start

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with the money then. We have this report. Billionaires'

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low taxes are becoming a problem for the economy.

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And it starts with a stat that made me just do

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a double take. The top 0 .1 % of households now

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hold 14 .4 % of US wealth. And that's up six

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points since 1990. Right. and the bottom 50 %

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of the country, they've slipped to just 2 .5%.

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My question is just, how? I get rich people have

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better accounts, but this feels like, it feels

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like geometry, not just good saving habits. It

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is geometry. It's a mechanism called buy, borrow,

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die. And to really get it, you have to sort of

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unlearn everything you think you know about income.

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Okay, lay it on me. Step one is buy. or really

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accumulate. If you or I have a job, we get a

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salary. The IRS sees that money hit our bank

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account, and they take a slice right away. Painfully

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true. But billionaires, they often avoid big

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salaries. Mark Zuckerberg took a $1 salary for

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years. Warren Buffett, I think it's still $100

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,000 a year. They're not getting rich on the

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paycheck. They're getting rich on the asset,

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the stock. OK, so they've got billions in stock.

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But you can't buy groceries with stock certificates.

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If they want a yacht, they have to sell some

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stock. Right. And that would trigger a tax. That's

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the assumption, but that's where you'd be wrong.

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That brings us to step two, borrow. This is where

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the magic trick happens. Instead of selling stock

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and paying capital gains, they go to a bank and

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say, hey, I have a billion dollars in stock,

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lend me money against that. So they're living

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on loans. They are. And here is the key, the

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part most people miss. The IRS does not classify

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a loan as income. Why not? I mean, cash is cash.

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If I have a million dollars from a loan, I can

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spend it just like if I earned it. Because legally,

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you have to pay a loan back. So it's a liability

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on your balance sheet, not an asset. You get

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the cash flow of a billionaire, you know, spending

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money on jets and homes. But on your tax return,

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you technically have the income of a pauper.

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You just have debt, not profit. That just feels

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like a cheat code. But you still have to pay

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interest on that loan, don't you? Oh, sure. But

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if your stock is growing at, say, 8 % a year,

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and the interest rate on your loan is 4 % or

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5%, you are still way ahead. And crucially, that

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interest rate is much, much lower than the 20

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or 30 % you'd pay in taxes if you sold the stock.

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OK, but eventually the bill comes due. You can't

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just borrow forever. You have to pay the principal

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back at some point. Well, that brings us to step

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three, die. Sounds final. When they pass away,

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those assets go to their heirs. And thanks to

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something in the tax code called step -up provisions,

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the cost basis of those assets gets reset to

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whatever the market value is on the day they

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die. OK, I'm going to need you to translate that

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into English for me. Right. So say you bought

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a stock for $10. It grows to $1 ,000. If you

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sell it while you're alive, you pay tax on that

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$990 profit. Right. But if you die and you leave

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it to your child, the IRS essentially treats

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it as if your child bought it for $1 ,000 that

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day. That $990 of growth, it just, it vanishes

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from the tax system. Poof! It is never taxed.

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So the wealth builds up, it compounds, they live

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on tax -free loans, and then the actual tax bill

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just disappears when they die. Effectively, yeah.

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And that's why the 400 wealthiest individuals

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have an effective tax rate of just 24 percent.

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While top labor earners, you know, people like

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doctors, lawyers, people working for a salary,

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they're often paying closer to 45 percent. And

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this isn't just about fairness, is it? The report

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says this is actually warping the entire consumer

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market. It's causing what some analysts are calling

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luxury divergence. We're seeing this split economy.

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Brands that cater to the truly super rich think

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Cartier their sales are soaring. They're totally

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immune to inflation. But the brands that rely

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on the affluent middle class, people who are

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doing well but aren't in that buy borrow die

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club. They're struggling because they're the

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ones actually paying taxes and feeling inflation.

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And here's the risk for everyone listening. The

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whole U .S. economy is becoming dependent on

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the spending of the very rich. The top 20 percent

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of households now account for almost 60 percent

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of all personal spending. So if the stock market

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takes a dip and those 400 people decide to stop

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buying Hermes bags for a month, the entire retail

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sector catches a cold. It makes the system incredibly

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fragile. It's so top heavy. Speaking of top heavy

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systems crashing. Yeah. Let's pivot to that tech

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wreck. You said three hundred billion dollars

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erased. Was that just like a bad week? or is

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something structural breaking down? It's structural,

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and it ties right back into our theme of control

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backfiring. For the last two years, the narrative

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has been AI is going to change everything, so

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just buy tech stocks. AI gold rush, yeah. But

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now, investors are starting to realize how AI

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is going to change things. The crash hit companies

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like Salesforce, Adobe, ServiceNow, these companies

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run on a SaaS model, software as a service. Right,

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which usually means they charge per seat. If

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I have a company with 100 employees, I buy 100

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licenses of Salesforce. That's the business model.

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But here's the paradox. If these new AI agents

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become truly productive, you might not need 100

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employees to do the work. You might only need

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50, plus a few AI agents. And I'm guessing the

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AI agents don't need a user license. Or at least

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the pricing model hasn't caught up to that yet.

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If a company needs fewer human seats, The revenue

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for these software giants just plummets. It wasn't

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that demand for the product went away. It was

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the realization that the AI efficiency they were

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promising might actually cannibalize their own

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sales. So by building the ultimate efficiency

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tool, they might have destroyed their own billing

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model. That's the fear. We saw the same thing

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with legal and data firms like LegalZoom and

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Thomson Reuters. They dropped too. If an AI can

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draft a solid contract, who needs to pay for

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LegalZoom? So the tech giants are worried they're

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whole business model is breaking. And they aren't

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the only ones worried about the rules changing.

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While tech is panicking about AI, the rest of

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the financial markets are sweating over this

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new proposal from the White House, one that could

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fundamentally change who controls the U .S. dollar.

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This is the Fed -Treasury accord I was reading

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about. It sounds incredibly boring, but the notes

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say it's actually dangerous. It sounds boring

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on purpose. It involves the nomination of Kevin

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Warsh for Fed Chairman, and he's suggesting that

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the Federal Reserve and the Treasury Department

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should start coordinating their actions much

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more closely. Which, to a normal person, just

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sounds like government agencies working together.

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What's so bad about that? Think of the economy

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like a car. The President and the Treasury, they

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control the gas pedal. They spend money to make

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the economy go fast. The Federal Reserve controls

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the brakes. They raise interest rates to slow

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things down and stop inflation. Okay. Gas and

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brakes. I get it. You need them to be separate.

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You need the driver to be a different person

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than the one holding the brake handle. If the

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President controls both the gas and the brakes...

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He might never use the brakes. He'd just floor

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it to win an election. That's the fear. The accord

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risks blurring that line between fiscal and monetary

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policy. If the Fed loses its independence, we

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lose the main safety mechanism we have against

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runaway inflation. So it's another case of trying

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to take control, in this case coordinating the

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agencies, and it could lead to a total loss of

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control over the economy. It's the theme of the

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day. Well, speaking of trying to take control

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and having it just blow up spectacularly in your

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face, we have to talk about Stephen Colbert.

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I was wondering when we'd get to the lighter

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side of unintended consequences. You can't talk

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about this kind of thing without bringing up

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the Streisand effect. For anyone who doesn't

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live on the internet, maybe remind us where that

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term even comes from. Right, Barbara Streisand.

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Years ago, she sued a photographer to get an

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aerial photo of her mansion removed from this

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huge collection of California coastline pictures.

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Before the lawsuit, that photo had been downloaded

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exactly six times. Six. Probably just by her

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neighbors wanting to see her pool. Probably.

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But the lawsuit became news. And because she

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tried to suppress it, the photo ended up getting

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viewed hundreds of times. of thousands of times.

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She spent over $200 ,000 in legal fees just to

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make the picture famous. The attempt to hide

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it is what made it go viral. And now, in 2026,

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the FCC just walked right into the very same

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trap. They really did. It involves late night

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with Stephen Colbert and a Senate candidate from

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Texas, a guy named James Tellerico. So Colbert

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books Tellerico. Pretty standard late night interview.

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Usually, yes. But Brendan Carr, the FCC chair,

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who's part of the administration's majority of

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appointees, he signals that maybe talk shows

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shouldn't be exempt from the equal time rule

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anymore. That's the rule that says if you give

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five minutes to one candidate, you have to offer

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five minutes to their opponent. I thought news

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shows didn't have to do that. They don't. And

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for decades, late night shows have been treated

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like news events for that rule. Carr signaled

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that might change. So... The lawyers at CBS panicked.

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They didn't want a legal fight with the administration,

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so they just pulled the interview. It never aired

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on TV. So he killed the broadcast to try and

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bury the story. They tried. But Colbert just

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took the interview and posted the whole thing

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on YouTube. And this is where the math gets really

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funny. The average TV broadcast for Colbert gets

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about 2 .7 million viewers. OK. The YouTube video

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of the suppressed interview, it hit 3 .7 million

00:12:02.659 --> 00:12:05.600
views almost overnight. So by trying to block

00:12:05.600 --> 00:12:07.960
it, the FCC guaranteed that a million more people

00:12:07.960 --> 00:12:10.960
saw it than if they had just let it air. Talk

00:12:10.960 --> 00:12:13.600
about a backfire. And it wasn't just views. It

00:12:13.600 --> 00:12:16.039
was engagement. The comment section was full

00:12:16.039 --> 00:12:19.059
of people saying things like, Dear FCC, thank

00:12:19.059 --> 00:12:20.840
you for bringing this to my attention. I had

00:12:20.840 --> 00:12:22.980
no idea who James Tellerico was before this.

00:12:23.039 --> 00:12:25.279
That is the ultimate irony. The administration

00:12:25.279 --> 00:12:27.960
tried to make a candidate invisible. Instead,

00:12:27.960 --> 00:12:30.820
they gave him a massive viral boost. And it signaled

00:12:30.820 --> 00:12:35.059
something else to voters. Fear. By trying so

00:12:35.059 --> 00:12:37.840
hard to suppress the interview, the administration

00:12:37.840 --> 00:12:39.980
basically sent a signal that they are worried

00:12:39.980 --> 00:12:42.980
about that Senate seat in Texas. Now, this Tallarico

00:12:42.980 --> 00:12:46.399
guy, he's part of a bigger trend we're seeing

00:12:46.399 --> 00:12:49.039
in the sources, isn't he? This fluent Christian.

00:12:49.210 --> 00:12:52.029
Democrat. This is the final piece of our unintended

00:12:52.029 --> 00:12:54.629
consequences puzzle. And it's fascinating because

00:12:54.629 --> 00:12:56.809
it really looks like a long term strategic backfire

00:12:56.809 --> 00:12:59.090
for the right. How so? Well, for decades, the

00:12:59.090 --> 00:13:01.110
GOP has been very successful at branding the

00:13:01.110 --> 00:13:03.830
left as godless or, you know, hostile to religion.

00:13:04.269 --> 00:13:06.230
They basically claimed ownership of faith based

00:13:06.230 --> 00:13:08.129
politics. Sure. That's been the playbook since

00:13:08.129 --> 00:13:11.509
the 80s, at least. But by painting Democrats

00:13:11.509 --> 00:13:13.590
as anti -religion, they created this vacuum.

00:13:13.970 --> 00:13:16.750
And now you're seeing a new archetype of candidate

00:13:16.750 --> 00:13:19.389
rise up to fill that vacuum, people who are naturally

00:13:19.389 --> 00:13:21.509
fluent in the language of faith, but who are

00:13:21.509 --> 00:13:24.169
running as Democrats. Like Telerico. Telerico

00:13:24.169 --> 00:13:26.669
is actually a pastor. But look at Senator John

00:13:26.669 --> 00:13:29.730
Ossoff in Georgia. He's Jewish, but he gave the

00:13:29.730 --> 00:13:32.590
speech at Big Bethel AME Church recently that

00:13:32.590 --> 00:13:35.169
has political operatives just buzzing. I read

00:13:35.169 --> 00:13:37.029
the transcript of this. He went full biblical.

00:13:37.230 --> 00:13:39.690
He really did. He compared. shared current political

00:13:39.690 --> 00:13:43.250
figures, specifically election deniers, to King

00:13:43.250 --> 00:13:49.429
Ahab's 400 false prophets. That's a powerful

00:13:49.429 --> 00:13:51.809
image. It's sophisticated rhetoric. He isn't

00:13:51.809 --> 00:13:53.649
just, you know, quoting scripture. He's using

00:13:53.649 --> 00:13:56.710
it to frame the political moment. And both Taylorico

00:13:56.710 --> 00:13:59.269
and Ossoff are actively houndering the stereotype.

00:13:59.669 --> 00:14:02.370
They are, as one source put it, meeting voters

00:14:02.370 --> 00:14:04.730
where they are, especially black and Latino voters

00:14:04.730 --> 00:14:06.649
in the South who are deeply religious. And because

00:14:06.649 --> 00:14:08.850
the bar was set so low, because the expectation

00:14:08.850 --> 00:14:10.889
was that Democrats just couldn't talk about faith

00:14:10.889 --> 00:14:13.029
when these guys do it, it just hits that much

00:14:13.029 --> 00:14:15.679
harder. Exactly. It completely disrupts the narrative.

00:14:15.879 --> 00:14:19.100
And the buzz is that Ossoff is looking very strong

00:14:19.100 --> 00:14:21.700
in his reelection bid against Representative

00:14:21.700 --> 00:14:25.179
Mike Collins. Strong enough to maybe move up

00:14:25.179 --> 00:14:27.039
the ladder. There's serious speculation in the

00:14:27.039 --> 00:14:30.340
notes. If Ossoff wins Georgia a purple state...

00:14:30.299 --> 00:14:33.580
By a decent margin, say five points, he basically

00:14:33.580 --> 00:14:36.500
creates a blueprint. A blueprint for 2028. He

00:14:36.500 --> 00:14:38.580
becomes an immediate front runner. The sources

00:14:38.580 --> 00:14:40.700
are comparing him to Governor Whitmer or Governor

00:14:40.700 --> 00:14:44.259
Shapiro. But Ossoff has this specific fluent

00:14:44.259 --> 00:14:46.600
Christian lane that could play very differently

00:14:46.600 --> 00:14:49.019
in those key swing states. It's just wild how

00:14:49.019 --> 00:14:51.700
all these threads connect. The FCC tries to silence

00:14:51.700 --> 00:14:55.279
a guy. He goes viral. The GOP tries to own religion.

00:14:55.460 --> 00:14:57.639
And it creates an opening for a pastor politician

00:14:57.639 --> 00:14:59.679
to rise up. And then if we zoom all the way out.

00:14:59.659 --> 00:15:01.419
Now, look at the pattern we've been talking about.

00:15:01.580 --> 00:15:03.480
It's all about systems and people trying to opt

00:15:03.480 --> 00:15:06.700
out or control the flow. Right. Let's just recap

00:15:06.700 --> 00:15:08.320
that for everyone. You have the billionaires

00:15:08.320 --> 00:15:10.960
using buy, borrow, die to opt out of the tax

00:15:10.960 --> 00:15:14.100
system. The result? A fragile, top -heavy economy

00:15:14.100 --> 00:15:17.279
that depends on luxury shoppers. You have AI

00:15:17.279 --> 00:15:20.600
companies trying to opt out of the old per -seat

00:15:20.600 --> 00:15:23.639
business model to be more efficient. The result?

00:15:23.840 --> 00:15:27.139
a $300 billion market crash because they broke

00:15:27.139 --> 00:15:29.419
their own revenue stream. And you have the government

00:15:29.419 --> 00:15:32.460
trying to opt out of media norms to control a

00:15:32.460 --> 00:15:35.240
narrative. The result? The Stray Sand effect

00:15:35.240 --> 00:15:38.299
creates a viral superstar. It seems like every

00:15:38.299 --> 00:15:40.759
time someone tries to tighten their grip, whether

00:15:40.759 --> 00:15:43.700
it's on their money, their software, or the media,

00:15:43.929 --> 00:15:46.309
something just slips right through. It raises

00:15:46.309 --> 00:15:48.490
a really important question for everyone listening,

00:15:48.529 --> 00:15:51.450
I think. We often assume that the people at the

00:15:51.450 --> 00:15:53.429
top, the billionaires, the regulators, the tech

00:15:53.429 --> 00:15:56.129
giants, that they actually have the wheel, that

00:15:56.129 --> 00:15:59.269
they are driving the car. But if the FCC can't

00:15:59.269 --> 00:16:02.429
even bury a YouTube video, and the tax code can't

00:16:02.429 --> 00:16:04.909
capture wealth, and the stock market can't figure

00:16:04.909 --> 00:16:07.490
out how to value efficiency, who actually holds

00:16:07.490 --> 00:16:09.649
the power? Are the traditional gatekeepers losing

00:16:09.649 --> 00:16:11.840
their grip? That is the question. I think they

00:16:11.840 --> 00:16:13.460
might be. And usually when the gatekeepers lose

00:16:13.460 --> 00:16:15.419
their grip, that's when things get really volatile

00:16:15.419 --> 00:16:18.220
but also really, really interesting. Well, that

00:16:18.220 --> 00:16:20.019
is definitely something to chew on for the rest

00:16:20.019 --> 00:16:23.059
of the week. So here's my challenge to you, the

00:16:23.059 --> 00:16:25.950
listener. Look for the Streisand effects in your

00:16:25.950 --> 00:16:28.889
own newsfeed this week Look for the things people

00:16:28.889 --> 00:16:31.070
are trying to hide or the systems. They're trying

00:16:31.070 --> 00:16:33.710
to control too tightly That's probably where

00:16:33.710 --> 00:16:36.129
the real story is and maybe keep an eye on that

00:16:36.129 --> 00:16:39.210
buy borrow die strategy It explains a lot more

00:16:39.210 --> 00:16:41.210
than just the deficit. Absolutely. Thanks for

00:16:41.210 --> 00:16:42.830
diving in with us We'll be back next time to

00:16:42.830 --> 00:16:45.289
connect some more dots until then stay curious