Welcome back to the deep dive. Today is Wednesday,
February 18th, 2026. And look, I know we usually
just dive right in, but I have to. I just have
to take 30 seconds here and soak in that Super
Bowl win. I knew this was coming. You're still
wearing the jersey, aren't you? I might be. Hey,
it's Super Bowl 60. The Seattle Seahawks took
down the Patriots. 2913. I don't even care about
the stats. I just care that for one week, Seattle
is allowed to be completely insufferable. It
was a pretty decisive night. I'll give you that.
But while you were, you know, watching the trophy
ceremony, did you see what the analysts were
saying about the actual game? I saw dominance.
I saw dark side defense. That's about as far
as I went. Well, see, the comparison to the old
Legion of Boom is now statistically valid. The
Patriots had 331 yards, which, you know, it looks
OK on paper. OK, but the deep dive. into the
game tape, it shows that a third of that, maybe
more, was in complete garbage time. New England
was already way behind. It was just a master
class in how to shut an opponent down. See, even
the data supports my happiness. But I know you.
You didn't come here to talk about defensive
schemes. You've got that tone in your voice that
says, while you were celebrating, something important
broke. You know me too well. While Seattle was
locking down the field, something a massive and
way less celebratory was happening in the financial
markets. We're talking a historic beating in
the tech sector. A beating? I thought tech was,
like, untouchable right now. Not anymore. We
saw a wipeout of nearly $300 billion in software
value just in early February. $300 billion? That's...
I mean, that is not a small correction. That
is a crater. It is. And that gets us to our mission
for this deep dive. We're not just reading you
the headlines today. We're looking at a whole
stack of sources from the economy, to the tax
code, to the media, to connect the dots on one
single theme. Unintended consequences. Intended
consequences. Okay, I'm with you. It's all about
control. You've got billionaires trying to control
their tax rate, tech companies trying to control
efficiency, the government trying to control
the media. And in every single story we have
today, that attempt to control the system, it
either backfired or it created a whole new problem.
So the harder you squeeze, the more sand slips
through your fingers. That is the vibe of the
week. Exactly. We're going to look at why billionaires
are playing by a totally different set of economic
rules, this buy, borrow, die strategy, and then
that AI reality check that caused the $300 billion
crash. And I see in our notes here, we've got
a really interesting story about Stephen Colbert,
the FCC, and I guess a modern day example of
the straight sand effect. Plus, a look at how
a very specific political strategy in the South
might be an unintended consequence of the culture
wars. It is a pack stack. All right. Let's start
with the money then. We have this report. Billionaires'
low taxes are becoming a problem for the economy.
And it starts with a stat that made me just do
a double take. The top 0 .1 % of households now
hold 14 .4 % of US wealth. And that's up six
points since 1990. Right. and the bottom 50 %
of the country, they've slipped to just 2 .5%.
My question is just, how? I get rich people have
better accounts, but this feels like, it feels
like geometry, not just good saving habits. It
is geometry. It's a mechanism called buy, borrow,
die. And to really get it, you have to sort of
unlearn everything you think you know about income.
Okay, lay it on me. Step one is buy. or really
accumulate. If you or I have a job, we get a
salary. The IRS sees that money hit our bank
account, and they take a slice right away. Painfully
true. But billionaires, they often avoid big
salaries. Mark Zuckerberg took a $1 salary for
years. Warren Buffett, I think it's still $100
,000 a year. They're not getting rich on the
paycheck. They're getting rich on the asset,
the stock. OK, so they've got billions in stock.
But you can't buy groceries with stock certificates.
If they want a yacht, they have to sell some
stock. Right. And that would trigger a tax. That's
the assumption, but that's where you'd be wrong.
That brings us to step two, borrow. This is where
the magic trick happens. Instead of selling stock
and paying capital gains, they go to a bank and
say, hey, I have a billion dollars in stock,
lend me money against that. So they're living
on loans. They are. And here is the key, the
part most people miss. The IRS does not classify
a loan as income. Why not? I mean, cash is cash.
If I have a million dollars from a loan, I can
spend it just like if I earned it. Because legally,
you have to pay a loan back. So it's a liability
on your balance sheet, not an asset. You get
the cash flow of a billionaire, you know, spending
money on jets and homes. But on your tax return,
you technically have the income of a pauper.
You just have debt, not profit. That just feels
like a cheat code. But you still have to pay
interest on that loan, don't you? Oh, sure. But
if your stock is growing at, say, 8 % a year,
and the interest rate on your loan is 4 % or
5%, you are still way ahead. And crucially, that
interest rate is much, much lower than the 20
or 30 % you'd pay in taxes if you sold the stock.
OK, but eventually the bill comes due. You can't
just borrow forever. You have to pay the principal
back at some point. Well, that brings us to step
three, die. Sounds final. When they pass away,
those assets go to their heirs. And thanks to
something in the tax code called step -up provisions,
the cost basis of those assets gets reset to
whatever the market value is on the day they
die. OK, I'm going to need you to translate that
into English for me. Right. So say you bought
a stock for $10. It grows to $1 ,000. If you
sell it while you're alive, you pay tax on that
$990 profit. Right. But if you die and you leave
it to your child, the IRS essentially treats
it as if your child bought it for $1 ,000 that
day. That $990 of growth, it just, it vanishes
from the tax system. Poof! It is never taxed.
So the wealth builds up, it compounds, they live
on tax -free loans, and then the actual tax bill
just disappears when they die. Effectively, yeah.
And that's why the 400 wealthiest individuals
have an effective tax rate of just 24 percent.
While top labor earners, you know, people like
doctors, lawyers, people working for a salary,
they're often paying closer to 45 percent. And
this isn't just about fairness, is it? The report
says this is actually warping the entire consumer
market. It's causing what some analysts are calling
luxury divergence. We're seeing this split economy.
Brands that cater to the truly super rich think
Cartier their sales are soaring. They're totally
immune to inflation. But the brands that rely
on the affluent middle class, people who are
doing well but aren't in that buy borrow die
club. They're struggling because they're the
ones actually paying taxes and feeling inflation.
And here's the risk for everyone listening. The
whole U .S. economy is becoming dependent on
the spending of the very rich. The top 20 percent
of households now account for almost 60 percent
of all personal spending. So if the stock market
takes a dip and those 400 people decide to stop
buying Hermes bags for a month, the entire retail
sector catches a cold. It makes the system incredibly
fragile. It's so top heavy. Speaking of top heavy
systems crashing. Yeah. Let's pivot to that tech
wreck. You said three hundred billion dollars
erased. Was that just like a bad week? or is
something structural breaking down? It's structural,
and it ties right back into our theme of control
backfiring. For the last two years, the narrative
has been AI is going to change everything, so
just buy tech stocks. AI gold rush, yeah. But
now, investors are starting to realize how AI
is going to change things. The crash hit companies
like Salesforce, Adobe, ServiceNow, these companies
run on a SaaS model, software as a service. Right,
which usually means they charge per seat. If
I have a company with 100 employees, I buy 100
licenses of Salesforce. That's the business model.
But here's the paradox. If these new AI agents
become truly productive, you might not need 100
employees to do the work. You might only need
50, plus a few AI agents. And I'm guessing the
AI agents don't need a user license. Or at least
the pricing model hasn't caught up to that yet.
If a company needs fewer human seats, The revenue
for these software giants just plummets. It wasn't
that demand for the product went away. It was
the realization that the AI efficiency they were
promising might actually cannibalize their own
sales. So by building the ultimate efficiency
tool, they might have destroyed their own billing
model. That's the fear. We saw the same thing
with legal and data firms like LegalZoom and
Thomson Reuters. They dropped too. If an AI can
draft a solid contract, who needs to pay for
LegalZoom? So the tech giants are worried they're
whole business model is breaking. And they aren't
the only ones worried about the rules changing.
While tech is panicking about AI, the rest of
the financial markets are sweating over this
new proposal from the White House, one that could
fundamentally change who controls the U .S. dollar.
This is the Fed -Treasury accord I was reading
about. It sounds incredibly boring, but the notes
say it's actually dangerous. It sounds boring
on purpose. It involves the nomination of Kevin
Warsh for Fed Chairman, and he's suggesting that
the Federal Reserve and the Treasury Department
should start coordinating their actions much
more closely. Which, to a normal person, just
sounds like government agencies working together.
What's so bad about that? Think of the economy
like a car. The President and the Treasury, they
control the gas pedal. They spend money to make
the economy go fast. The Federal Reserve controls
the brakes. They raise interest rates to slow
things down and stop inflation. Okay. Gas and
brakes. I get it. You need them to be separate.
You need the driver to be a different person
than the one holding the brake handle. If the
President controls both the gas and the brakes...
He might never use the brakes. He'd just floor
it to win an election. That's the fear. The accord
risks blurring that line between fiscal and monetary
policy. If the Fed loses its independence, we
lose the main safety mechanism we have against
runaway inflation. So it's another case of trying
to take control, in this case coordinating the
agencies, and it could lead to a total loss of
control over the economy. It's the theme of the
day. Well, speaking of trying to take control
and having it just blow up spectacularly in your
face, we have to talk about Stephen Colbert.
I was wondering when we'd get to the lighter
side of unintended consequences. You can't talk
about this kind of thing without bringing up
the Streisand effect. For anyone who doesn't
live on the internet, maybe remind us where that
term even comes from. Right, Barbara Streisand.
Years ago, she sued a photographer to get an
aerial photo of her mansion removed from this
huge collection of California coastline pictures.
Before the lawsuit, that photo had been downloaded
exactly six times. Six. Probably just by her
neighbors wanting to see her pool. Probably.
But the lawsuit became news. And because she
tried to suppress it, the photo ended up getting
viewed hundreds of times. of thousands of times.
She spent over $200 ,000 in legal fees just to
make the picture famous. The attempt to hide
it is what made it go viral. And now, in 2026,
the FCC just walked right into the very same
trap. They really did. It involves late night
with Stephen Colbert and a Senate candidate from
Texas, a guy named James Tellerico. So Colbert
books Tellerico. Pretty standard late night interview.
Usually, yes. But Brendan Carr, the FCC chair,
who's part of the administration's majority of
appointees, he signals that maybe talk shows
shouldn't be exempt from the equal time rule
anymore. That's the rule that says if you give
five minutes to one candidate, you have to offer
five minutes to their opponent. I thought news
shows didn't have to do that. They don't. And
for decades, late night shows have been treated
like news events for that rule. Carr signaled
that might change. So... The lawyers at CBS panicked.
They didn't want a legal fight with the administration,
so they just pulled the interview. It never aired
on TV. So he killed the broadcast to try and
bury the story. They tried. But Colbert just
took the interview and posted the whole thing
on YouTube. And this is where the math gets really
funny. The average TV broadcast for Colbert gets
about 2 .7 million viewers. OK. The YouTube video
of the suppressed interview, it hit 3 .7 million
views almost overnight. So by trying to block
it, the FCC guaranteed that a million more people
saw it than if they had just let it air. Talk
about a backfire. And it wasn't just views. It
was engagement. The comment section was full
of people saying things like, Dear FCC, thank
you for bringing this to my attention. I had
no idea who James Tellerico was before this.
That is the ultimate irony. The administration
tried to make a candidate invisible. Instead,
they gave him a massive viral boost. And it signaled
something else to voters. Fear. By trying so
hard to suppress the interview, the administration
basically sent a signal that they are worried
about that Senate seat in Texas. Now, this Tallarico
guy, he's part of a bigger trend we're seeing
in the sources, isn't he? This fluent Christian.
Democrat. This is the final piece of our unintended
consequences puzzle. And it's fascinating because
it really looks like a long term strategic backfire
for the right. How so? Well, for decades, the
GOP has been very successful at branding the
left as godless or, you know, hostile to religion.
They basically claimed ownership of faith based
politics. Sure. That's been the playbook since
the 80s, at least. But by painting Democrats
as anti -religion, they created this vacuum.
And now you're seeing a new archetype of candidate
rise up to fill that vacuum, people who are naturally
fluent in the language of faith, but who are
running as Democrats. Like Telerico. Telerico
is actually a pastor. But look at Senator John
Ossoff in Georgia. He's Jewish, but he gave the
speech at Big Bethel AME Church recently that
has political operatives just buzzing. I read
the transcript of this. He went full biblical.
He really did. He compared. shared current political
figures, specifically election deniers, to King
Ahab's 400 false prophets. That's a powerful
image. It's sophisticated rhetoric. He isn't
just, you know, quoting scripture. He's using
it to frame the political moment. And both Taylorico
and Ossoff are actively houndering the stereotype.
They are, as one source put it, meeting voters
where they are, especially black and Latino voters
in the South who are deeply religious. And because
the bar was set so low, because the expectation
was that Democrats just couldn't talk about faith
when these guys do it, it just hits that much
harder. Exactly. It completely disrupts the narrative.
And the buzz is that Ossoff is looking very strong
in his reelection bid against Representative
Mike Collins. Strong enough to maybe move up
the ladder. There's serious speculation in the
notes. If Ossoff wins Georgia a purple state...
By a decent margin, say five points, he basically
creates a blueprint. A blueprint for 2028. He
becomes an immediate front runner. The sources
are comparing him to Governor Whitmer or Governor
Shapiro. But Ossoff has this specific fluent
Christian lane that could play very differently
in those key swing states. It's just wild how
all these threads connect. The FCC tries to silence
a guy. He goes viral. The GOP tries to own religion.
And it creates an opening for a pastor politician
to rise up. And then if we zoom all the way out.
Now, look at the pattern we've been talking about.
It's all about systems and people trying to opt
out or control the flow. Right. Let's just recap
that for everyone. You have the billionaires
using buy, borrow, die to opt out of the tax
system. The result? A fragile, top -heavy economy
that depends on luxury shoppers. You have AI
companies trying to opt out of the old per -seat
business model to be more efficient. The result?
a $300 billion market crash because they broke
their own revenue stream. And you have the government
trying to opt out of media norms to control a
narrative. The result? The Stray Sand effect
creates a viral superstar. It seems like every
time someone tries to tighten their grip, whether
it's on their money, their software, or the media,
something just slips right through. It raises
a really important question for everyone listening,
I think. We often assume that the people at the
top, the billionaires, the regulators, the tech
giants, that they actually have the wheel, that
they are driving the car. But if the FCC can't
even bury a YouTube video, and the tax code can't
capture wealth, and the stock market can't figure
out how to value efficiency, who actually holds
the power? Are the traditional gatekeepers losing
their grip? That is the question. I think they
might be. And usually when the gatekeepers lose
their grip, that's when things get really volatile
but also really, really interesting. Well, that
is definitely something to chew on for the rest
of the week. So here's my challenge to you, the
listener. Look for the Streisand effects in your
own newsfeed this week Look for the things people
are trying to hide or the systems. They're trying
to control too tightly That's probably where
the real story is and maybe keep an eye on that
buy borrow die strategy It explains a lot more
than just the deficit. Absolutely. Thanks for
diving in with us We'll be back next time to
connect some more dots until then stay curious