WEBVTT

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Imagine for just a second that you are working

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this truly exhausting, high stress, 80 hour a

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week job. Oh, sounds brutal. Right. You're making

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these massive decisions, managing thousands of

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people, literally bearing the weight of an entire

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organization on your shoulders. Yeah. And then

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finally, payday rolls around. You open that envelope

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and your paycheck is for exactly one single dollar.

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I mean, it completely shatters the normal expectations

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of you know, how effort and reward are supposed

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to work. Exactly. Most people would probably

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frame a check like that or maybe just laugh.

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I mean, considering it wouldn't even cover a

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cup of coffee. But as we're going to see today,

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that single dollar bill has a shockingly rich

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history. Welcome to The Deep Dive. Glad to be

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here. Today we have this fascinating stack of

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source material, mainly centered around a comprehensive

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Wikipedia article on the concept of the $1 salary.

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It's a really deep rabbit hole. It is. And our

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mission today is to unpack the historical origins,

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the very strange legal quirks, and the hidden

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economic loopholes that explain exactly why billionaires

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tech CEOs and world leaders deliberately choose

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to be paid the equivalent of a candy bar. Right.

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Because it's never just about the dollar. Never.

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And look, as we dig into this, we are going to

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mention some highly polarizing political figures

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who have used this tactic. Oh, yeah. People spanning

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the entire political spectrum. Yeah. From JFK

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to Donald Trump. But to be totally clear to you

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listening, We aren't here to endorse or critique

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their politics today. We are just acting as your

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guides to the factual history of this fascinating

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financial maneuver. Yeah, our focus is entirely

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on the mechanics of the one dollar salary itself.

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Right. We are looking at how this practice started

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as this wartime necessity and then morphed into

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a corporate tax strategy and eventually became

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this like highly calculated political flex. OK,

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let's unpack this. We really have to start at

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the very beginning because the most obvious question

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you have to ask when you hear about someone taking

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a one dollar salary is, well, why a dollar? Right.

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If you are going to be incredibly wealthy and

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generous, and you genuinely want to work for

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the public good, Why not just volunteer for zero

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dollars? I mean, it's a fair question. And the

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answer is actually rooted in federal law. Really?

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Yeah. Specifically, a piece of legislation known

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as 31 U .S. Code Section 1342. OK, sounds very

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bureaucratic. It is. It's part of the broader

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Anti -Deficiency Act. And with very few exceptions,

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it strictly forbids the United States government

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from accepting the services of unpaid volunteers.

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Wait, which? Which sounds completely counterintuitive

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on the surface. Why would a government ever turn

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down free labor? It comes down to liability and

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legal accountability. Oh, OK. Right. Because

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in a functioning democracy, you cannot have random

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unaccountable citizens just acting on behalf

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of the government. Right. Wielding state power.

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Exactly. Or making massive logistical decisions

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without a formal legally binding chain of command.

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A government absolutely needs its workers to

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be classified as legal employees. So they can

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actually be fired or prosecuted if they mess

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up. Exactly. So they are subject to strict oversight.

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ethical regulations, you know, the law. That

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makes sense. And to establish that formal employer

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-employee relationship under contract law, there

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must be an exchange of value. Right, right. There

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has to be what legal scholars call consideration.

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Oh, I get it. It's like... It's like when you

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sell a junker car to a family member for a single

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dollar. Yes. Perfect example. You aren't actually

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trying to make a profit off your cousin. You

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just need to generate a legally binding receipt

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so you can officially transfer the title. Right.

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To prove a valid transaction occurred. Yeah.

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The dollar is just a placeholder for a legal

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handshake. That is the perfect way to look at

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it. Generates a paper trail. And this bureaucratic

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placeholder became absolutely crucial in the

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early to mid 20th century. Right. Birthing a

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whole generation of what were called dollar -a

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-year men. Yeah. The first recorded instance

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was actually Gifford Pinchot, who worked under

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President Theodore Roosevelt. Oh, wow. So it

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goes back a ways. It does. But the concept didn't

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truly explode until the logistical nightmares

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of World War I and World War II. Because suddenly,

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the government is facing these massive global

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crises, right? And they desperately need to mobilize

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American industry overnight. They need supply

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chains, manufacturing, raw material logistics.

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And the people who know how to build those systems

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aren't career bureaucrats. They are private sector

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executives. Right. But government pay scales

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were rigidly fixed by Congress. You couldn't

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just slot a titan of industry into a standard

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government salary. Because they were used to

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making millions. Exactly. So during World War

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I, about 1 ,000 executives were brought in to

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help the United States manage this massive industrial

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pivot. Wow, 1 ,000. Yeah, people like Bernard

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Baruch, who helped staff the Advisory Commission

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to the Council of National Defense. So the government

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essentially realizes they need these massive

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industrial brains. But. Democratic laws required

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legal accountability and federal budgets couldn't

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match their corporate rates. Right. So their

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home companies just continued paying their normal

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corporate salaries and the U .S. government paid

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them exactly one dollar to make them official

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accountable government employees. That is wild.

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And the sources show this continued straight

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into World War II with some really memorable

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examples. Oh yeah, totally. Like you had Paul

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G. Blazer, the founder of Ashland Oil, serving

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as chairman of district refining for the petroleum

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administration. You had Herman Wouk, the famous

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author, working in Washington as a dollar a year

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man writing radio scripts for the U .S. Treasury's

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defense bond campaign. Yeah, and even socialite

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Doris Duke worked in a canteen for U .S. sailors

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in Egypt for a one dollar salary. That is so

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fascinating. And it wasn't just the U .S. either,

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right? No, Canada heavily utilized this model

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as well. They had C .D. Howe, who was famously

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known as Canada's Minister of Everything. Minister

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of Everything. That's a great title. Right. He

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created a massive rearmament program using dollar

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a year men. He needed people who knew how to

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build factories and scale production instantly.

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So he just bypassed traditional bureaucratic

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hiring entirely. Exactly. He brought in private

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sector publishers and industrialists. What's

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fascinating here is how beautifully this illustrates

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the tension between crisis and democracy. Yeah,

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how so? Well, in times of existential threat,

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the government desperately needed private sector

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efficiency. But the bedrock laws of a democratic

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society required legal accountability. Right.

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The one dollar salary brilliantly bridged that

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gap. It was a bureaucratic hack that literally

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helped win world wars. So the government proves

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this bureaucratic hack works perfectly for wartime

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survival. But, you know, a legal loophole this

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effective doesn't stay a secret for long. Definitely

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not. Once the wars ended, corporate accountants

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realized this exact same, quote unquote, patriotic

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structure could be weaponized for profit. Yeah,

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the script gets flipped. Right. Fast forward

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to the late 1990s and the early 2000s, and this

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concept gets completely hijacked by the corporate

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world. specifically in Silicon Valley. The context

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shifts entirely from government service to corporate

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maneuvering. We start seeing it incredibly often

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with struggling companies trying to conserve

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cash runway. Or booming tech startups, right?

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Exactly. Where the founders are heavily invested

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in the equity rather than needing a biweekly

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paycheck. And the roster of people who adopted

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this playbook is basically a Mount Rushmore of

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modern billionaires. Oh, it really is. According

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to the source, we're talking about Steve Jobs

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at Apple, Elon Musk at Tesla and SpaceX. Mark

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Zuckerberg at Facebook, Meg Whitman at Hewlett

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-Packard, Jack Dorsey at Twitter. I mean, the

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list goes on. It's basically an industry standard

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at a certain level. But hold on, I have to step

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in here and challenge this on behalf of the listener.

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If we look at this purely through the lens of

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a cash salary, wait a minute. If these CEOs are

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only making a dollar, how are they affording

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private jets? A single dollar doesn't buy a mega

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yacht. What is the actual mechanism keeping these

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executives unimaginably rich if their paycheck

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is $1? Well, we really have to separate the concept

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of salary from compensation. Okay, great idea.

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The reality of the modern corporate $1 salary

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is that it is almost never their only source

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of income. While their base cash salary is a

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single dollar, they receive millions, sometimes

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billions in other forms of compensation. Like

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what? This usually comes in the form of stock

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options, restricted stock units, or massive performance

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bonuses. Right. The sources give a staggering,

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highly specific example of this. In the 2010

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to 2011 fiscal year, Larry Ellison The founder

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of Oracle famously took a $1 salary. Yes, he

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did. But when you look at the SEC filings, he

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earned over $77 million in other forms of compensation.

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Yep. $77 million. I mean, that is a far cry from

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the patriotic dollar -a -year mend of World War

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I. The scale is entirely different, yeah. Now,

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to understand why corporate boards actually approve

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this, we have to look at the pro -business argument.

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OK, what do they claim the benefit is? Executives

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argue that taking stock instead of a massive

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cash salary ties the management's performance

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directly to their financial benefits. Skin in

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the game. Exactly. The logic is that if the stock

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price reflects the actual health and value of

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a company, then a CEO who is paid in equity only

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gets rich if the shareholders also win. Right.

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It's an engineered alignment of incentives. If

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the company tanks, The CEO's compensation tanks

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with it. That's the theory. Yeah. And on paper,

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that sounds great. I only win if you win. But

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here's where it gets really interesting. Oh,

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yeah. Because tying compensation to stock isn't

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just about this beautiful corporate synergy and

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aligning incentives. It leads directly to a much

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darker hidden motive. The tax. Exactly. Yeah.

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It is fundamentally about outsmarting the tax

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man. It's like... Taking compensation in stock

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rather than cash is like getting paid in lottery

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tickets where you control the odds, entirely

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bypassing the specific toll booth that pays for

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the highway you drive on. That is the exact mechanism

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at play. We really need to break down the specific

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tax loopholes detailed in the source. Yeah. How

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does the math actually work? So in the United

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States, when an executive is granted stock and

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options, those are eventually subject to capital

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gains taxes when they are realized, you know,

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when the stock is finally sold. Right. But by

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reducing their official cash salary to one dollar,

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they legally avoid paying into something very

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specific. payroll taxes. Which are the taxes

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that are automatically deducted from every standard

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W -2 employee's paycheck? Exactly. We are talking

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about the roughly 7 .65 % tax rate that is specifically

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earmarked to fund the social safety net like

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Medicare and Social Security. Wow. And every

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typical salaried worker pays this on their income.

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Right. But because executives structure their

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massive windfalls as capital gains rather than

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traditional salaried income, they legally shield

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the bulk of their true earnings from those specific

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payroll taxes entirely. That is just wild. And

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it gets deeper. Furthermore, many of these executives

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utilize a strategy often called buy, borrow,

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die. Buy, borrow, die. Sounds ominous. It is

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a bit. Instead of ever selling their stock and

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triggering that capital gains tax we talked about,

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they simply use their billions in stock as collateral

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to take out low interest bank loans. Oh, to fund

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their lavish lifestyles. Yep. And borrowed money

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isn't treated as taxable income. So they completely

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bypass the system. They dodge the payroll tax

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toll booth entirely. Pretty much. And this brings

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up a massive counter argument from the detractors

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mentioned in the text, because Aside from the

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tax avoidance, paying executives almost entirely

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in stock fundamentally changes how a company

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is run. It really does. It strongly incentivizes

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dangerous short -term planning over long -term

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stability. Because if your entire net worth is

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tied to the stock price hitting a specific metric

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by the end of the next quarter, you are highly

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motivated to artificially pump that stock up

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today. You see this constantly. A CEO incentivized

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by short term stock bumps might slash the research

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and development budget or execute massive layoffs

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to reduce operating costs or initiate massive

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corporate stock buybacks. And those actions will

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absolutely make the stock price spike in the

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short term, allowing the executive to invest

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their options and cash out. Exactly. But those

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exact same actions will completely hollow out

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the company's innovation and stability five or

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10 years down the line. And this is exactly why

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you listening to this should care about this.

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Yeah. This isn't just abstract. billionaire math

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happening in a vacuum. No, it has real -world

00:12:48.580 --> 00:12:51.200
consequences. Right. If you happen to be an employee

00:12:51.200 --> 00:12:54.220
or even just a retail investor with a 401k tied

00:12:54.220 --> 00:12:57.659
up in one of these companies, a CEO who is chasing

00:12:57.659 --> 00:13:00.580
short -term stock bumps to trigger their compensation

00:13:00.580 --> 00:13:03.379
packages can severely affect your livelihood.

00:13:03.600 --> 00:13:05.620
Yeah, they get the golden parachute. And the

00:13:05.620 --> 00:13:07.740
retail investors and the everyday workers are

00:13:07.740 --> 00:13:09.879
left holding the bag of a hollowed out company.

00:13:10.090 --> 00:13:13.190
The decisions made to maximize those alternative

00:13:13.190 --> 00:13:16.029
compensation packages send ripple effects through

00:13:16.029 --> 00:13:19.490
the entire economy. Absolutely. And what is perhaps

00:13:19.490 --> 00:13:22.149
most intriguing is how this concept hasn't just

00:13:22.149 --> 00:13:24.529
stayed isolated in the corporate boardroom. Oh,

00:13:24.529 --> 00:13:26.629
right. It comes full circle. It has recently

00:13:26.629 --> 00:13:29.289
made its way back to where it started, the government.

00:13:29.889 --> 00:13:32.429
But the underlying motive has changed drastically

00:13:32.429 --> 00:13:35.149
since the days of the World War One industrial

00:13:35.149 --> 00:13:38.029
mobilization. Yeah, because the corporate world

00:13:38.029 --> 00:13:41.240
figured out that taking a one dollar salary makes

00:13:41.240 --> 00:13:44.580
you look incredibly selfless to the public. Right.

00:13:44.759 --> 00:13:46.659
Even if you're making millions on the back end.

00:13:46.840 --> 00:13:50.080
The PR value is huge. It is. It's fascinating

00:13:50.080 --> 00:13:52.980
how this has become the ultimate political flex.

00:13:53.820 --> 00:13:57.740
You see wealthy leaders using this exact playbook,

00:13:57.899 --> 00:14:00.460
weaponizing their wealth. to look like ultimate

00:14:00.460 --> 00:14:03.440
public servants. Yeah. The sources list several

00:14:03.440 --> 00:14:06.019
prominent modern political figures who have utilized

00:14:06.019 --> 00:14:08.340
the strategy. You have Arnold Schwarzenegger

00:14:08.340 --> 00:14:10.480
when he was the governor of California, Mitt

00:14:10.480 --> 00:14:12.419
Romney as the governor of Massachusetts, and

00:14:12.419 --> 00:14:14.740
Michael Bloomberg as the mayor of New York City.

00:14:14.759 --> 00:14:16.860
And even going further back, right? Yeah. Presidents

00:14:16.860 --> 00:14:19.220
like Herbert Hoover and John F. Kennedy utilize

00:14:19.220 --> 00:14:21.759
similar concepts, either taking no salary or

00:14:21.759 --> 00:14:24.279
donating it, given their immense family wealth.

00:14:24.460 --> 00:14:26.740
And the text also details how Donald Trump utilized

00:14:26.740 --> 00:14:30.159
this. As promised during his campaign, he stated

00:14:30.159 --> 00:14:33.379
he would take a $1 salary. The sources note that

00:14:33.379 --> 00:14:36.279
during his first term, he donated his first three

00:14:36.279 --> 00:14:38.320
months of salary to the National Park Service

00:14:38.320 --> 00:14:41.039
and then subsequently donated quarters to various

00:14:41.039 --> 00:14:43.840
other federal departments. It perfectly illustrates

00:14:43.840 --> 00:14:46.759
how high profile this maneuver is in the political

00:14:46.759 --> 00:14:49.340
arena. It really does. It generates massive headlines.

00:14:49.580 --> 00:14:52.379
Because it's an incredibly potent piece of political

00:14:52.379 --> 00:14:55.460
theater. In fact, the source shares a highly

00:14:55.460 --> 00:14:58.039
viral anecdote that proves just how deeply this

00:14:58.039 --> 00:15:00.460
idea has embedded itself in the public imagination

00:15:00.460 --> 00:15:05.639
globally. Yes. In 2015, a 15 -year -old boy named

00:15:05.639 --> 00:15:08.700
Corbin Duncan started a petition demanding that

00:15:08.700 --> 00:15:11.460
the Australian Prime Minister, Malcolm Turnbull,

00:15:12.120 --> 00:15:15.440
reduce his salary to exactly one dollar. A 15

00:15:15.440 --> 00:15:17.500
-year -old high schooler in Australia is tapping

00:15:17.500 --> 00:15:19.899
into a century -old American legal loophole.

00:15:20.139 --> 00:15:22.840
That is wild. It really is. Now, the petition

00:15:22.840 --> 00:15:25.940
ultimately failed, but it gained massive international

00:15:25.940 --> 00:15:28.440
media coverage. Because it hits a nerve. Exactly.

00:15:28.600 --> 00:15:30.919
It proves that the public intuitively understands

00:15:30.919 --> 00:15:33.980
the symbolism of the $1 salary. It communicates

00:15:33.980 --> 00:15:36.799
sacrifice and solidarity. Which raises an important

00:15:36.799 --> 00:15:39.779
question. What does it actually mean when our

00:15:39.779 --> 00:15:42.159
public servants do this today? What do you mean?

00:15:42.429 --> 00:15:46.129
Well, the $1 government salary started as a highly

00:15:46.129 --> 00:15:49.769
specific, necessary legal mechanism to employ

00:15:49.769 --> 00:15:52.710
private citizens during a global wartime crisis.

00:15:52.750 --> 00:15:55.809
Right. But today, it almost exclusively acts

00:15:55.809 --> 00:15:58.330
as a public relations maneuver that just highlights

00:15:58.330 --> 00:16:01.149
a politician's immense pre -existing wealth.

00:16:01.549 --> 00:16:03.129
Right. And there's a flip side to this quote

00:16:03.129 --> 00:16:07.080
unquote selfless PR stunt. If we normalize the

00:16:07.080 --> 00:16:09.120
idea that public servants shouldn't take a salary,

00:16:09.539 --> 00:16:11.720
aren't we just pricing the working class out

00:16:11.720 --> 00:16:14.059
of politics entirely? That is the danger, yeah.

00:16:14.200 --> 00:16:16.659
I mean, the salary for a governor, a mayor, or

00:16:16.659 --> 00:16:19.620
a president exists precisely so that a person

00:16:19.620 --> 00:16:21.600
who isn't independently wealthy can afford to

00:16:21.600 --> 00:16:23.299
step away from their private career and actually

00:16:23.299 --> 00:16:26.200
do the job. If the new baseline for being a good

00:16:26.200 --> 00:16:29.120
politician is working for a single dollar, it

00:16:29.120 --> 00:16:31.960
silently implies to the voting public that only

00:16:31.960 --> 00:16:34.320
the ultra wealthy are truly suited for public

00:16:34.320 --> 00:16:36.149
office. because they're the only ones who can

00:16:36.149 --> 00:16:39.350
afford to serve. Exactly. By celebrating the

00:16:39.350 --> 00:16:42.610
$1 political salary, we risk creating a system

00:16:42.610 --> 00:16:45.450
where high office is exclusively reserved for

00:16:45.450 --> 00:16:48.029
those with massive pre -existing stock portfolios.

00:16:48.029 --> 00:16:51.149
Yeah, yeah. It turns public service from a paid

00:16:51.149 --> 00:16:54.509
civic duty into like a philanthropic hobby for

00:16:54.509 --> 00:16:56.929
the ultra -witch. That is a really sobering way

00:16:56.929 --> 00:16:58.870
to look at it. So what does this all mean? We've

00:16:58.870 --> 00:17:00.370
gone on quite the journey with these sources

00:17:00.370 --> 00:17:02.389
today. I really have. We started with a quirky

00:17:02.389 --> 00:17:05.230
federal law from the early 1900s, the Anti -Deficiency

00:17:05.230 --> 00:17:09.119
Act, that required legal and birthed the patriotic

00:17:09.119 --> 00:17:11.400
dollar -a -year men who helped win world wars.

00:17:11.500 --> 00:17:14.279
Yep. Then we watched that noble legal workaround

00:17:14.279 --> 00:17:16.839
get completely reshaped by Silicon Valley into

00:17:16.839 --> 00:17:19.759
a mechanism to dodge payroll taxes while still

00:17:19.759 --> 00:17:22.420
raking in millions through complex stock options

00:17:22.420 --> 00:17:25.400
and borrowing strategies. The buy, borrow, die

00:17:25.400 --> 00:17:28.250
strategy. Right. And finally, we saw it come

00:17:28.250 --> 00:17:30.390
right back to the political stage as a modern

00:17:30.390 --> 00:17:33.349
PR stunt for wealthy politicians. It really means

00:17:33.349 --> 00:17:35.269
that whenever you see a price tag of exactly

00:17:35.269 --> 00:17:38.390
$1, whether it's on a tech CEO's SEC filing or

00:17:38.390 --> 00:17:41.049
a politician's campaign promise, it is rarely

00:17:41.049 --> 00:17:43.680
an act of pure, simple charity. Almost never.

00:17:43.900 --> 00:17:47.440
There is almost always a deeply complex legal

00:17:47.440 --> 00:17:50.579
financial or political mechanism hiding right

00:17:50.579 --> 00:17:52.700
beneath the surface. Yeah. In the intersecting

00:17:52.700 --> 00:17:55.019
worlds of law and finance, the most symbolic

00:17:55.019 --> 00:17:57.660
gestures are almost always the most highly engineered.

00:17:57.980 --> 00:18:01.039
The dollar is never just a dollar. It is a lever

00:18:01.039 --> 00:18:03.480
moving something much larger behind the scenes.

00:18:04.240 --> 00:18:06.299
Absolutely. And before we go, I want to leave

00:18:06.299 --> 00:18:08.559
you with one final thought experiment to mull

00:18:08.559 --> 00:18:11.240
over, something that really builds on this strange

00:18:11.240 --> 00:18:14.019
intersection of law and value. Oh, I like thought

00:18:14.019 --> 00:18:17.140
experiments. Deep in the Wikipedia source material,

00:18:17.539 --> 00:18:20.519
there is a see -also link to a centuries -old

00:18:20.519 --> 00:18:23.839
legal concept called a peppercorn. A peppercorn?

00:18:24.099 --> 00:18:26.680
Like the spice? Literally a peppercorn. It originated

00:18:26.680 --> 00:18:29.460
in English common law, often involving land leases.

00:18:30.000 --> 00:18:32.519
It's a metaphor for a ridiculously small payment,

00:18:32.920 --> 00:18:35.119
literally a single peppercorn, used merely to

00:18:35.119 --> 00:18:37.259
satisfy the strict requirements for a legal contract.

00:18:37.539 --> 00:18:39.880
Just like the one dollar. Exactly. The one dollar

00:18:39.880 --> 00:18:41.740
salary we've been talking about today is basically

00:18:41.740 --> 00:18:44.099
the modern American peppercorn. That makes perfect

00:18:44.099 --> 00:18:47.539
sense. But think about where we are heading as

00:18:47.539 --> 00:18:50.079
we move into a future dominated by decentralized

00:18:50.079 --> 00:18:53.579
digital economies, cryptocurrency or gig work

00:18:53.579 --> 00:18:57.500
increasingly managed and assigned by AI. Will

00:18:57.500 --> 00:19:00.420
the traditional concept of a salary disappear

00:19:00.420 --> 00:19:03.519
entirely? It's very possible. Right. If literal

00:19:03.519 --> 00:19:06.160
cash money isn't the primary mechanism that legally

00:19:06.160 --> 00:19:09.240
binds us to our work anymore, what is going to

00:19:09.240 --> 00:19:12.380
become the new $1 of the future? What will be

00:19:12.380 --> 00:19:15.119
the new peppercorn that tethers us to our labor?

00:19:15.369 --> 00:19:17.990
I mean, the medium of exchange might evolve from

00:19:17.990 --> 00:19:22.269
dollars to data or fiat to crypto, but the fundamental

00:19:22.269 --> 00:19:24.730
legal need for consideration, that foundational

00:19:24.730 --> 00:19:27.190
handshake, it never really disappears. It really

00:19:27.190 --> 00:19:29.109
makes you wonder what your next employment contract

00:19:29.109 --> 00:19:31.150
is actually going to look like. Thank you so

00:19:31.150 --> 00:19:32.730
much for joining us on this deep dive. It was

00:19:32.730 --> 00:19:35.009
a pleasure. Keep questioning the headlines. Keep

00:19:35.009 --> 00:19:37.789
looking for the loopholes. And remember, the

00:19:37.789 --> 00:19:39.710
next time you picture that envelope with a single

00:19:39.710 --> 00:19:42.650
dollar bill inside, you'll know exactly how much

00:19:42.650 --> 00:19:43.430
it's really worth.
