WEBVTT

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Let's start with a headache. A very specific,

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very expensive headache. I want you to picture

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someone. Let's call her Sarah. Sarah is smart.

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Back in, say, 2010, right when the market was

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on the floor, she scraped together a down payment

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and bought a duplex. Good timing. In Austin,

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Texas. Oh, yeah. Great timing. Buying at the

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bottom. I mean, that is the dream. Absolutely.

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And she's been a good landlord. You know, she

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fixed the toilets. She dealt with the tenants,

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paid the mortgage. And now, almost 15 years later,

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that duplex has like quadrupled in value. She

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is sitting on a mountain of equity. She wants

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to sell it, maybe buy a small apartment complex,

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you know, level up her game. Makes sense. She

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feels like a genius. Until she calls her accountant.

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Exactly. She calls her CPA all excited and says,

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I'm going to sell. for a million dollars. And

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the CPA goes click clack on the calculator and

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says, great, Sarah, just be prepared to write

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a check to the government for about 150 grand,

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maybe more. Oof. The silent partner emerges.

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And Sarah is floored. She's thinking, wait, that's

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my money. I took the risk. I fixed the roof.

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But the government says, congrats on the win.

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We'll take our cut now. It feels like a penalty

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for success. It feels like friction. It does.

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And that friction is exactly why so many investors

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get stuck. They call it lock -in. You have this

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asset. It's done its job. It's appreciated. But

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you are terrified to sell it because the transaction

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cost, specifically the capital gains tax and

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depreciation recapture, it just decimates your

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buying power. Right. You literally cannot afford

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to sell and buy the next thing because you lose

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too much of your stack in the transfer. But what

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if you didn't have to? What if Sarah could sell

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that duplex, take the full million dollars and

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roll it into that apartment complex without paying

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Uncle Sam a single dime? I'm not talking about

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evading taxes, you know, briefcases of cash in

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the Caymans or anything. I'm talking about legally

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pausing the bill. Then you were talking about

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Section 131 of the Internal Revenue Code. The

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wealth shortcut. That's what they call it. Yeah.

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That is what we are unpacking today. The 1031

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exchange. And look. I know tax code sounds like

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the cure for insomnia. It usually is. Yeah. But

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this isn't a lecture on filing forms. This is

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a deep dive into. Maybe the single most powerful

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wealth compounding tool in the United States.

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We are going to talk about how the richest real

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estate moguls play a different game than the

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rest of us. It is a different game. It's a game

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of velocity. It's about keeping your capital

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moving and growing without stopping to pay a

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toll every few years. But I have to be the skeptic

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here for a second. Please do. The IRS isn't exactly

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known for its generosity. So if they're letting

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Sarah keep her money, there has to be a catch.

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Is this actually a gift or is it just a golden

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pair of handcuffs that... keeps you stuck in

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the real estate market forever. That is the right

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question to ask. And no, it's not a gift. It's

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a trade -off. You get to keep your money working

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for you. But in exchange, you have to follow

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a set of rules so rigid that one wrong step,

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I mean, literally one day late or $1 out of place,

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and the whole thing just blows up. So today,

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we are going to map out that minefield. We're

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going to walk through the death zone of deadlines,

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the trap of something called boot. Which is a

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hilarious term. It is a hilarious term we will

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get to. And the myths about swapping your vacation

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home. We'll also talk about the tired landlord

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who wants out of the toilet fixing business but

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doesn't want to pay the taxes. Because there

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are solutions for them too. Okay, let's start

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at the foundation. What exactly is this thing?

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When we say Section 131, what are we actually

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defining? At its most basic level... A Section

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1031 exchange or, you know, a like -kind exchange

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allows an investor to sell a property held for

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business or investment and reinvest the proceeds

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into a new property of like -kind. And by doing

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that, they defer the capital gains tax. I want

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to stop you on one word there. Defer. Yes. Because

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people hear tax -free exchange and they think

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of the tax just poof, vanishes. It definitely

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does not vanish. Think of it like an interest

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-free loan from the government. Normally, when

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you sell, you know the tax. With a 1031, the

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IRS says, okay, keep that tax money, use it to

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buy the next building, but... We are keeping

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a tab. We know you owe us. You're just kicking

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the can down the road. You are kicking the can

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down the road. You can kick that can for a really

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long time. You can kick it for decades. You could

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swap from property A to property B, hold B for

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10 years, swap to property C, and you just keep

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rolling that tax bill forward, never actually

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paying it. And as we'll see later, there is a

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very specific way to make that bill disappear

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entirely, but that involves... Well, dying. The

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ultimate deadline. Yes. OK, so the concept is

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swapping. But I assume I can't just call up a

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buddy who has a warehouse and say, hey, I'll

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trade you my duplex for your warehouse. And we

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just like swap keys. You actually could. I mean,

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that is how the law was originally written, a

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simultaneous swap. But how often does that really

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happen? It's almost impossible to find two people

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who want each other's specific properties at

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the exact same time with the exact same values.

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So how does it work in the real world then? Sarah

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sells her duplex to some guy, Bob. Bob doesn't

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have a building to trade. He just has cash. This

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is where the modern delayed exchange comes in.

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And this is actually a fascinating bit of legal

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history. It wasn't always allowed. It took a

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guy named T .J. Starker to fight the government

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to make this happen. Starker. Right. I hear people

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call these Starker exchanges. So who was he?

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TJ Starker was a timber investor in Oregon back

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in the 60s. He made a deal with a big timber

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corporation. He gave them his land. I mean, premium

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timberland. OK. But they didn't have the land

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he wanted in return right at that moment. So

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they basically gave him an IOU. They said, we

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will die you suitable replacement property over

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the next few years until we match the value.

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So he transferred his title, but he didn't get

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cash. He got a credit. Correct. A credit on their

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books. And the IRS looked at this and went ballistic.

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He said, no, no, no. You sold your land. You

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accepted a promise to pay. That is a sale. You

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owe us the tax right now. And Starker sued them.

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He fought them all the way to the Ninth Circuit

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Court of Appeals. And in 1979, the court ruled

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in his favor. They said, essentially, that as

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long as he didn't touch the cash, the intent

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was an exchange, even if there was a delay. Wow.

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That case, Starker v. United States, it revolutionized

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real estate. It created the industry we have

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today. So thanks to Mr. Starker, Sarah doesn't

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need a simultaneous swap. She can sell her duplex

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on Monday, put the money in a special account,

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and buy her new apartment complex months later.

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Yes. But, and this is a massive but, after the

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sugar case, the IRS said, fine, you can delay,

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but we are not giving you forever. They imposed

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strictly rigid timelines. Okay, let's get into

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the rules. The first hurdle is this concept of

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like -kind. This feels like the gatekeeper. You

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know, if the properties aren't like -kind, you

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can't even play the game. But what does that

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actually mean? If Sarah sells a residential duplex,

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does she have to buy another residential duplex?

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This is the single biggest misconception I see.

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People stress out thinking they have to match

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the asset exactly. They think, I sold a condo,

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I must buy a condo. Right. Or, I sold a warehouse,

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I need another industrial building. Totally wrong.

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For real estate, the definition of like -kind

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is incredibly broad. The code says properties

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must be of the same nature or character, but

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they do not have to be of the same grade or quality.

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Unpack that for me. Nature versus grade. So in

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the eyes of the IRS, dirt is dirt. A plot of

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raw, undeveloped land in Nevada is like -kind

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to a skyscraper in Manhattan. Seriously? Yes.

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A strip mall is like -kind to a dairy farm. A

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rental house is like kind to a doctor's office.

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They are all considered real property held for

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investment. That is wild flexibility. So Sarah

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isn't stuck in residential rentals. She could

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sell the duplex and buy, I don't know, a gas

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station. If she buys the land in the building,

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yes, absolutely. She could pivot her entire portfolio.

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She could move from high maintenance residential

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rentals to... you know, commercial industrial

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warehouses. She can move from a cold climate

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to a warm one. Speaking of moving, are there

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geographical limits? Can she sell the Austin

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duplex and buy a villa in Tuscany? She would

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love that, I'm sure. But no, the code is very

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specific here. Real property located within the

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United States is not like kinds to property located

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outside the United States. So it's domestic only?

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Generally, yeah. The 50 states and D .C., there

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are some nuances with the U .S. Virgin Islands

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and Guam, but for the most part, you cannot cross

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international borders. You sell in the U .S.,

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you buy in the U .S. Okay. So what about the

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stuff inside the building? Let's say Sarah is

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selling a furnished vacation rental. She's selling

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the house, sure, but she's also selling the sofas,

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the beds, the appliances. Does that count? Ah,

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this brings us to a major change in the law.

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We have to talk about the Tax Cuts and Jobs Act

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of 2017. TCJA. Before 2017, you could do a 1031

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exchange on personal property. Personal property?

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Like heady machinery. Kelty Airlines could swap

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an old Boeing 747 for a new one and defer the

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tax. A construction company could swap a fleet

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of bulldozers. You could even do it with thoroughbred

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racehorses or patents. Wait, really? You could

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1031 exchange a racehorse. You could, but the

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2017 act killed all of that. As of January 1st,

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2018, Section 131 is restricted strictly to real

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property, real estate only. So if you own a construction

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company today and you trade in your old excavator

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for a new one, that's a taxable event. Correct.

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No more deferral for equipment. And that applies

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to the furniture in Sarah's rental, too. The

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house qualifies. The used sofa inside it. Technically,

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that is personal property. It does not qualify.

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That feels like a trap. I mean, if I sell a hotel,

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half the value is the furniture and fixtures.

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It creates a complication for sure. We'll talk

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about how to handle that later. But strictly

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speaking, personal property is out. Oh, and here's

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a fun fact about the old rules. Just to show

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you how granular the IRS gets. Oh. when you could

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exchange animals. Section 1031E explicitly stated

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that livestock of different sexes are not like

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kind. You are joking. I am not. You could not

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swap a bull for a cow. So the IRS was basically

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running a gender reveal party on cattle farms.

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Sorry, it's a boy. Pay your taxes. Essentially,

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yes. I think their logic was that they serve

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different functions in the business. Breeding

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versus dairy, for example. It's moot now because

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livestock isn't real estate, but it just shows

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you Do not assume logic applies here. Only the

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code applies. Only the code. Okay, noted. Don't

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swap cows. And I assume stocks and crypto are

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out too. explicitly out. You cannot swap Apple

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stock for Microsoft stock. You cannot swap Bitcoin

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for Ethereum. Section 1031 is the last great

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tax shelter, and it is reserved almost exclusively

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for real estate investors. Okay, let's go back

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to Sarah. She knows she can sell her duplex.

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She knows she wants an apartment complex. She

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knows she can't catch the cash. Walk us through

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the death zone, the timeline. This is where most

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people fail. The moment Sarah closes the sale

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of her duplex, the minute that deed is recorded,

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a stopwatch starts. Yeah. And this stopwatch

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has no pause button. Day one. Day one. She now

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has two deadlines running concurrently. The first

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one is the 45 -day identification period. 45

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days to buy the new places? No, no, not to buy.

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45 days to simply tell the IRS via her intermediary

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what she might buy. She has to identify potential

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replacement properties in writing. 45 days seems

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like plenty of time. You would think so. But

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let's play this out. Sarah sells on May 1st.

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She spends the first week just celebrating and

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waiting for funds to clear. Okay, now it's May

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8th. She calls a broker. I find me an apartment

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complex. Broker takes a week to send her some

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listings. Now it's May 15th. She tours three

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of them. Tour garbage. One is good. She makes

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an offer. Okay, so she's making progress. But

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the seller of that good property is traveling.

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They don't respond for four days. Then they counteroffer.

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Sarah counters back. Suddenly it's June. She's

00:11:57.460 --> 00:12:00.320
30 days in. If this deal falls apart during inspection,

00:12:00.659 --> 00:12:03.559
she has 15 days left to find a backup. And if

00:12:03.559 --> 00:12:06.440
she doesn't? If midnight on the 45th day strikes

00:12:06.440 --> 00:12:08.799
and she hasn't locked in a list of properties,

00:12:09.039 --> 00:12:12.980
the exchange is dead. Game over. Pay the taxes.

00:12:13.220 --> 00:12:15.000
Can she get an extension? What if she gets the

00:12:15.000 --> 00:12:18.389
flu? What if the 45th day is a Sunday? No. No

00:12:18.389 --> 00:12:21.470
and no. The IRS is brutal. If the deadline falls

00:12:21.470 --> 00:12:23.870
on a Sunday, you better act by Friday. If you

00:12:23.870 --> 00:12:27.350
get sick, too bad. The only exception is a presidentially

00:12:27.350 --> 00:12:29.549
declared disaster like a hurricane or massive

00:12:29.549 --> 00:12:32.250
wildfire that literally destroys the area. That

00:12:32.250 --> 00:12:35.110
is just high pressure. So she has to submit this

00:12:35.110 --> 00:12:37.450
list. Can she just list every property for sale

00:12:37.450 --> 00:12:40.070
in Austin just to be safe? No, you can't just

00:12:40.070 --> 00:12:41.830
copy the phone book. There are three specific

00:12:41.830 --> 00:12:44.269
rules for identification and you have to pick

00:12:44.269 --> 00:12:47.230
one lane. OK, lane number one. The three property

00:12:47.230 --> 00:12:49.809
rule. This is the most common one. You can identify

00:12:49.809 --> 00:12:52.610
up to three specific properties. It doesn't matter

00:12:52.610 --> 00:12:54.909
what they're worth. Sarah sold for a million

00:12:54.909 --> 00:12:58.009
dollars. She could identify three skyscrapers

00:12:58.009 --> 00:13:00.870
worth $50 million each. As long as it's three

00:13:00.870 --> 00:13:04.049
or fewer, she is safe. Simple enough. Pick your

00:13:04.049 --> 00:13:06.230
top three favorites. But what if she wants to

00:13:06.230 --> 00:13:08.929
buy a portfolio? What if she's selling the big

00:13:08.929 --> 00:13:12.450
duplex to buy 10 little rental houses in a cheaper

00:13:12.450 --> 00:13:15.269
market? Then she uses lane number two. The 200

00:13:15.269 --> 00:13:17.789
% rule. She can identify as many properties as

00:13:17.789 --> 00:13:21.610
she wants, 4, 10, 20, as long as the total value

00:13:21.610 --> 00:13:23.870
of everything on the list is not more than 200

00:13:23.870 --> 00:13:25.990
% of what she sold. Okay. So she sold for $1

00:13:25.990 --> 00:13:28.970
million. She can list 20 houses as long as the

00:13:28.970 --> 00:13:30.970
total value of those 20 houses isn't more than

00:13:30.970 --> 00:13:33.610
$2 million. Correct. But if she lists 20 houses

00:13:33.610 --> 00:13:36.490
and they're worth $2 .1 million, she has violated

00:13:36.490 --> 00:13:38.909
the rule. And now she falls into lane number

00:13:38.909 --> 00:13:41.389
three, which I call the suicide mission. That

00:13:41.389 --> 00:13:44.429
sounds promising. The 95 % rule. If you violate

00:13:44.429 --> 00:13:46.669
the first two rules, so you list more than three

00:13:46.669 --> 00:13:50.529
properties, and their value is huge, you can

00:13:50.529 --> 00:13:53.269
still save the exchange. But only if you actually

00:13:53.269 --> 00:13:56.169
acquire 95 % of the total value you identified.

00:13:56.490 --> 00:13:58.990
So if I list 10 properties worth $10 million.

00:13:59.350 --> 00:14:01.789
You have to buy $9 .5 million worth of them.

00:14:01.990 --> 00:14:03.909
You basically have to buy everything on your

00:14:03.909 --> 00:14:07.480
list. If one seller backs out, you fail. Almost

00:14:07.480 --> 00:14:09.799
nobody uses this rule intentionally. So stick

00:14:09.799 --> 00:14:12.399
to the rule of three. It is the safest. But remember,

00:14:12.539 --> 00:14:16.259
once that 45th day passes, you cannot change

00:14:16.259 --> 00:14:19.279
your list. If Sarah identifies property A, B,

00:14:19.360 --> 00:14:23.159
and C, and on day 46 she sees property D, which

00:14:23.159 --> 00:14:27.179
is the deal of the century, she cannot buy property

00:14:27.179 --> 00:14:29.820
D tax -free. She is handcuffed to her list. Completely.

00:14:29.860 --> 00:14:32.360
That is the stress of the 45 days. But then there's

00:14:32.360 --> 00:14:35.019
the second deadline. The 180 days. Right. She

00:14:35.019 --> 00:14:37.179
has 180 days from the initial sale to actually

00:14:37.179 --> 00:14:39.259
close on the new property. It feels like six

00:14:39.259 --> 00:14:41.899
months. It feels doable. Usually it is. Yeah.

00:14:41.960 --> 00:14:44.399
But there is a hidden trap here, too. The rule

00:14:44.399 --> 00:14:47.940
says 180 days or are the due date of your tax

00:14:47.940 --> 00:14:50.200
return for that year, whichever is earlier. Oh,

00:14:50.279 --> 00:14:54.179
that is sneaky. It's so sneaky. Imagine Sarah

00:14:54.179 --> 00:14:57.240
sells her property on December 31st. Her tax

00:14:57.240 --> 00:15:00.340
return is due April 15th. That is only about

00:15:00.340 --> 00:15:04.220
105 days away. If she doesn't know the rule and

00:15:04.220 --> 00:15:07.080
she schedules her closing for May 1st. She blows

00:15:07.080 --> 00:15:09.159
the deadline. She blows the deadline because

00:15:09.159 --> 00:15:12.139
the tax return deadline came first. So she has

00:15:12.139 --> 00:15:14.679
to file an extension for her taxes just to get

00:15:14.679 --> 00:15:18.080
the full 180 days. It's a paperwork trap that

00:15:18.080 --> 00:15:20.580
catches people every single year. OK, so we have

00:15:20.580 --> 00:15:23.019
the timeline. Sarah is sweating, but she's moving.

00:15:23.120 --> 00:15:25.320
Now let's talk about the money. Because you said

00:15:25.320 --> 00:15:27.299
earlier she can't touch it. Correct. This is

00:15:27.299 --> 00:15:29.100
called constructive receipt. If Sarah has the

00:15:29.100 --> 00:15:31.500
right to access the funds, the IRS considers

00:15:31.500 --> 00:15:34.340
them paid. The exchange is over. So at the closing

00:15:34.340 --> 00:15:36.960
table, when the buyer hands over the check. Sarah

00:15:36.960 --> 00:15:39.659
cannot touch it. She cannot even see it. She

00:15:39.659 --> 00:15:42.600
needs a qualified intermediary or a QI. Who is

00:15:42.600 --> 00:15:45.299
this person? Is it her lawyer? Her accountant?

00:15:45.519 --> 00:15:48.419
It generally cannot be her lawyer or her accountant.

00:15:48.779 --> 00:15:51.399
It has to be an independent third party whose

00:15:51.399 --> 00:15:54.860
business is facilitating exchanges. If she uses

00:15:54.860 --> 00:15:57.399
her brother or her employee, they're considered

00:15:57.399 --> 00:16:00.080
agents of hers, and the exchange is disqualified.

00:16:00.340 --> 00:16:03.620
So she has to hire a pro. Yes, and she has to

00:16:03.620 --> 00:16:06.539
hire them before the sale closes. This is crucial.

00:16:06.659 --> 00:16:09.120
I've seen people close the deal, get the wire

00:16:09.120 --> 00:16:11.799
into their bank account, and then call me asking,

00:16:12.019 --> 00:16:15.340
hey, can I send this to a QI now? Too late. No,

00:16:15.399 --> 00:16:17.500
it is too late. The toast is burnt. So the money

00:16:17.500 --> 00:16:20.039
goes from the title company to the QI. The QI

00:16:20.039 --> 00:16:22.379
holds it in a vault, basically. And then when

00:16:22.379 --> 00:16:25.740
Sarah buys the apartment complex, the QI wires

00:16:25.740 --> 00:16:28.360
the money to that seller. Exactly. The QI is

00:16:28.360 --> 00:16:30.679
the gatekeeper of the funds. Now let's talk about

00:16:30.679 --> 00:16:32.559
boot. I mean, you mentioned this is the trap.

00:16:32.720 --> 00:16:35.220
So Sarah sells for a million dollars. She finds

00:16:35.220 --> 00:16:37.620
a great apartment complex for $900 ,000. She

00:16:37.620 --> 00:16:40.720
thinks, great, I saved $100 ,000. And the IRS

00:16:40.720 --> 00:16:43.259
thinks, great, that $100 ,000 is profit you took

00:16:43.259 --> 00:16:46.240
off the table. That is cash boot. So she pays

00:16:46.240 --> 00:16:49.340
tax on the difference. Yes. If she keeps $100

00:16:49.340 --> 00:16:53.120
,000 cash, she pays capital gains tax on that

00:16:53.120 --> 00:16:56.320
$100 ,000. The rest is deferred, but she writes

00:16:56.320 --> 00:16:58.559
a check for that portion. That makes sense. I

00:16:58.559 --> 00:17:01.240
get the cash. I pay the tax. But there's a version

00:17:01.240 --> 00:17:06.519
of boot that feels unfair. Mortgage boot. This

00:17:06.519 --> 00:17:09.500
is the silent killer. To defer all tax, you have

00:17:09.500 --> 00:17:12.660
to do two things. Buy equal or greater value

00:17:12.660 --> 00:17:15.210
and replace your debt. Replace your debt. Explain

00:17:15.210 --> 00:17:17.829
that. Let's say Sarah's duplex was sold for a

00:17:17.829 --> 00:17:20.329
million, but she had a $400 ,000 mortgage on

00:17:20.329 --> 00:17:24.710
it. When she sells, the bank gets paid off. Now

00:17:24.710 --> 00:17:26.529
she buys the new place for a million dollars.

00:17:27.130 --> 00:17:29.150
But she decides, you know what, I don't want

00:17:29.150 --> 00:17:30.789
a big mortgage. I'm just going to get a $300

00:17:30.789 --> 00:17:33.069
,000 loan. She's being financially responsible,

00:17:33.470 --> 00:17:36.009
deleveraging. The IRS doesn't see it that way.

00:17:36.250 --> 00:17:38.589
They see that her debt dropped from $400K to

00:17:38.589 --> 00:17:41.910
$300K. That $100 ,000 difference is debt relief.

00:17:42.410 --> 00:17:45.549
The IRS treats debt relief exactly the same as

00:17:45.549 --> 00:17:47.509
receiving cash. Wait, hold on. So she didn't

00:17:47.509 --> 00:17:49.750
get a check. She just owes less money to the

00:17:49.750 --> 00:17:52.470
bank and she has to pay taxes on that $100 ,000.

00:17:52.950 --> 00:17:56.470
Yes, unless she puts in $100 ,000 of her own

00:17:56.470 --> 00:17:59.329
extra cash to offset it. But if she just drops

00:17:59.329 --> 00:18:02.289
the mortgage amount without adding cash, she

00:18:02.289 --> 00:18:04.670
has mortgage moot. It's taxable income. That

00:18:04.670 --> 00:18:07.190
is baffling to the average person. I borrowed

00:18:07.190 --> 00:18:09.730
less money, so now I owe taxes. That goes back

00:18:09.730 --> 00:18:11.869
to the theory of the exchange. You are supposed

00:18:11.869 --> 00:18:15.190
to be continuing your investment position. If

00:18:15.190 --> 00:18:17.410
you reduce your liability, you have effectively

00:18:17.410 --> 00:18:20.450
cashed out part of your obligation. So the golden

00:18:20.450 --> 00:18:23.630
rule for Sarah is buy equal or up in price and

00:18:23.630 --> 00:18:27.069
carry equal or up in debt. Precisely. Or bring

00:18:27.069 --> 00:18:29.250
cash to the table to fill the gap. Let's pivot

00:18:29.250 --> 00:18:31.809
to the fun stuff. The scenarios everyone asks

00:18:31.809 --> 00:18:34.170
about at dinner parties. Can I swap my rental

00:18:34.170 --> 00:18:37.519
for a beach house? Ah, the vacation home. Everyone

00:18:37.519 --> 00:18:39.720
wants to do this. It's an investment, I swear.

00:18:39.839 --> 00:18:41.839
I just happen to test the quality of the sand

00:18:41.839 --> 00:18:45.000
personally for two months a year. Right. I'm

00:18:45.000 --> 00:18:46.559
holding a board meeting with my family and a

00:18:46.559 --> 00:18:49.200
cooler of margaritas. The IRS wasn't born yesterday.

00:18:49.420 --> 00:18:51.779
They know this game. For years, this was a battleground.

00:18:51.940 --> 00:18:55.000
But in 2008, they issued a safe harbor. It's

00:18:55.000 --> 00:18:57.779
called Revenue Procedure 2008 -16. What does

00:18:57.779 --> 00:19:02.150
a safe harbor say? It says... Okay, we will believe

00:19:02.150 --> 00:19:04.490
it is an investment property if you follow these

00:19:04.490 --> 00:19:07.450
rules. First, you must own the property for at

00:19:07.450 --> 00:19:10.089
least 24 months. This applies to the one you're

00:19:10.089 --> 00:19:11.710
selling and the one you're buying. Okay, two

00:19:11.710 --> 00:19:14.849
years, end. During each of those two years, you

00:19:14.849 --> 00:19:17.670
must rent it out to a stranger, not your cousin,

00:19:17.750 --> 00:19:20.690
not your mom, at fair market value for at least

00:19:20.690 --> 00:19:23.089
14 days per year. So it has to be a real rental.

00:19:23.089 --> 00:19:25.869
It has to generate real income. Yes, and here

00:19:25.869 --> 00:19:29.220
is the kicker. Your personal use cannot exceed

00:19:29.220 --> 00:19:33.000
14 days per year or 10 % of the days it is rented,

00:19:33.119 --> 00:19:36.059
whichever is greater. So if Sarah buys a beach

00:19:36.059 --> 00:19:39.099
house in Florida with a 1031 exchange and she

00:19:39.099 --> 00:19:42.339
rents it out for 300 days a year. She can use

00:19:42.339 --> 00:19:45.279
it for 30 days, 10%. But if she only rents it

00:19:45.279 --> 00:19:46.799
out for two weeks. I can only use it for two

00:19:46.799 --> 00:19:49.140
weeks, 14 days. If she stays for three weeks,

00:19:49.259 --> 00:19:52.019
she violates the safe harbor. It becomes a residence,

00:19:52.119 --> 00:19:55.440
not an investment. And the 1031 is disallowed.

00:19:55.640 --> 00:19:57.880
That is strict. So you can't just buy a retirement

00:19:57.880 --> 00:20:01.880
home and leave it empty. No. However, peep do

00:20:01.880 --> 00:20:04.500
play the long game. This is the moving in strategy.

00:20:04.740 --> 00:20:07.440
Explain that. Sarah buys the house in Florida.

00:20:07.680 --> 00:20:10.400
She follows the rules. She rents it out for two

00:20:10.400 --> 00:20:13.980
years. She limits her visits. Then, after two

00:20:13.980 --> 00:20:17.579
years, her intent changes. She decides to move

00:20:17.579 --> 00:20:20.380
in. She makes it her primary residence. Is that

00:20:20.380 --> 00:20:24.180
legal? Yes. You can convert a rental to a residence.

00:20:25.640 --> 00:20:28.279
And listen closely, if she wants to sell it later

00:20:28.279 --> 00:20:31.099
and claim the primary residence tax exclusion.

00:20:31.559 --> 00:20:34.799
That's the Section 121 exclusion. If you live

00:20:34.799 --> 00:20:36.519
in a house for two of the last five years, you

00:20:36.519 --> 00:20:39.859
get $250 ,000 off profit tax -free. Right, or

00:20:39.859 --> 00:20:42.579
$500 ,000 if you're married. But if you acquired

00:20:42.579 --> 00:20:45.299
that house through a 1031 exchange, the rules

00:20:45.299 --> 00:20:47.579
are much tighter. First, you have to hold it

00:20:47.579 --> 00:20:49.859
for fully five years before you can sell, not

00:20:49.859 --> 00:20:52.420
two. Okay, five years. And second, you cannot

00:20:52.420 --> 00:20:54.809
wipe out the depreciation you took. And third,

00:20:54.990 --> 00:20:57.109
under new rules, you have to prorate the gain.

00:20:57.490 --> 00:21:00.029
You can't just say, oh, it's my home now. All

00:21:00.029 --> 00:21:02.670
the tax from the last 20 years is gone. No, the

00:21:02.670 --> 00:21:04.730
IRS will allocate the gain between the rental

00:21:04.730 --> 00:21:06.430
years and the residence years. So there's not

00:21:06.430 --> 00:21:08.950
a magic eraser. Used to be, but they closed that

00:21:08.950 --> 00:21:11.490
loophole. It's still a good strategy, but it's

00:21:11.490 --> 00:21:12.869
not a get -out -of -jail -free card anymore.

00:21:13.190 --> 00:21:15.609
What about the reverse? Sarah finds the dream

00:21:15.609 --> 00:21:18.210
apartment complex, but her duplex hasn't sold

00:21:18.210 --> 00:21:20.900
yet. In a hot market, sellers won't wait for

00:21:20.900 --> 00:21:23.519
you to sell your old junk. She has to buy N and

00:21:23.519 --> 00:21:27.220
now W. That is a reverse 1031. How does that

00:21:27.220 --> 00:21:29.799
even work? You can't exchange something you haven't

00:21:29.799 --> 00:21:32.519
sold. You can, but it is complex. You cannot

00:21:32.519 --> 00:21:34.700
hold title to both properties at the same time.

00:21:34.900 --> 00:21:37.680
So Sarah hires an exchange accommodation title

00:21:37.680 --> 00:21:41.859
holder, or EAT. An EAT. The EAT basically steps

00:21:41.859 --> 00:21:44.640
in and buys the new property for her. They hold

00:21:44.640 --> 00:21:47.000
the title in a special LLC. They park it. So

00:21:47.000 --> 00:21:50.099
the ET owns the apartment complex? Yes. While

00:21:50.099 --> 00:21:52.920
Sarah frantically tries to sell her duplex, once

00:21:52.920 --> 00:21:55.059
she sells the duplex, the money goes to the QI,

00:21:55.200 --> 00:21:58.019
and the ET then transfers the apartment complex

00:21:58.019 --> 00:22:00.599
to Sarah. It sounds expensive. It is. The fees

00:22:00.599 --> 00:22:03.519
are higher. The legal work is denser. But if

00:22:03.519 --> 00:22:06.059
you're trying to save $200 ,000 in taxes, paying

00:22:06.059 --> 00:22:08.220
$5 ,000 or $10 ,000 in extra fees is worth it.

00:22:08.339 --> 00:22:11.740
But remember, the 180 -day clock still applies.

00:22:12.299 --> 00:22:15.380
The ETT can only hold that property for 180 days

00:22:15.380 --> 00:22:17.940
if Sarah can't sell her duplex in six months.

00:22:18.099 --> 00:22:20.640
The deal unwinds. The whole thing unwinds. Now,

00:22:20.700 --> 00:22:23.059
I want to address a specific listener. Let's

00:22:23.059 --> 00:22:25.559
call him Tired Tom. Tom has been doing this for

00:22:25.559 --> 00:22:29.059
30 years. He owns 10 rental houses. He is sick

00:22:29.059 --> 00:22:32.500
of calls about broken furnaces at 2 a .m. He

00:22:32.500 --> 00:22:35.440
wants to sell, but his basis is so low. I mean,

00:22:35.440 --> 00:22:37.779
he bought these houses in the 90s that his tax

00:22:37.779 --> 00:22:40.660
bill would be millions. He feels trapped. He

00:22:40.660 --> 00:22:42.839
wants a 1031, but he doesn't want another property

00:22:42.839 --> 00:22:45.779
to manage. Tom is the perfect candidate for a

00:22:45.779 --> 00:22:49.460
DST, a Delaware Statutory Trust. We touched on

00:22:49.460 --> 00:22:51.440
this in the intro, but let's go deep. What is

00:22:51.440 --> 00:22:54.440
a DST? Imagine a massive institutional -grade

00:22:54.440 --> 00:22:57.240
property, a $100 million apartment community

00:22:57.240 --> 00:23:00.339
in Dallas, or an Amazon distribution center,

00:23:00.460 --> 00:23:02.460
or a portfolio of medical offices. Obviously,

00:23:02.480 --> 00:23:05.299
Tom can't buy that himself. But a sponsor, a

00:23:05.299 --> 00:23:07.599
big real estate company, buys it and places it

00:23:07.599 --> 00:23:10.119
into a trust. They then slice that trust into

00:23:10.119 --> 00:23:12.700
hundreds of little pieces. Tom can sell his rental

00:23:12.700 --> 00:23:14.779
houses and buy a beneficial interest in that

00:23:14.779 --> 00:23:17.440
trust. And the IRS accepts a piece of a trust

00:23:17.440 --> 00:23:20.180
as real estate. Yes, that was the breakthrough.

00:23:20.420 --> 00:23:23.920
Revenue ruling, 2004 -86. The IRS confirmed that

00:23:23.920 --> 00:23:26.359
owning a slice of a DST is like -kind to owning

00:23:26.359 --> 00:23:29.440
a rental house. So Tom moves his money from his

00:23:29.440 --> 00:23:32.019
headaches into this giant, professionally managed

00:23:32.019 --> 00:23:34.609
building. What does he have to do? Nothing. He

00:23:34.609 --> 00:23:36.710
checks his mailbox. He gets a distribution check

00:23:36.710 --> 00:23:39.289
every month. No tenants, no toilets, no trash.

00:23:39.509 --> 00:23:42.170
It is purely passive. That sounds too good to

00:23:42.170 --> 00:23:44.390
be true. Give me the skepticism. What's the catch?

00:23:44.650 --> 00:23:47.890
The catch is control. Tom used to be the king

00:23:47.890 --> 00:23:49.650
of his rental houses. If he wanted to paint them

00:23:49.650 --> 00:23:52.170
blue, he painted them blue. If he wanted to raise

00:23:52.170 --> 00:23:55.950
rents, he raised rents. In a DST, he is a silent

00:23:55.950 --> 00:23:58.890
passenger. He has zero vote. If the manager does

00:23:58.890 --> 00:24:02.430
a bad job, Tom can't fire him. And fees. I imagine

00:24:02.430 --> 00:24:04.539
there are fees. The fees can be heavy. Upturned

00:24:04.539 --> 00:24:07.380
loads, management fees. You are paying for the

00:24:07.380 --> 00:24:09.960
convenience. Also, it's illiquid. You can't just

00:24:09.960 --> 00:24:12.480
sell your share on a Tuesday like a stock. You're

00:24:12.480 --> 00:24:14.759
usually locked in for five to ten years until

00:24:14.759 --> 00:24:16.839
the sponsor sells the property. So if Tom needs

00:24:16.839 --> 00:24:19.759
emergency cash, he's stuck. He is stuck. But

00:24:19.759 --> 00:24:22.440
for someone whose primary goal is deferred taxes

00:24:22.440 --> 00:24:25.500
and stop working, it is a lifesaver. It's also

00:24:25.500 --> 00:24:27.740
great for spare change. What do you mean by that?

00:24:27.920 --> 00:24:30.819
Let's say Sarah does her exchange. She sells

00:24:30.819 --> 00:24:33.789
for a million, buys for $900 ,000. She has that

00:24:33.789 --> 00:24:36.569
$100 ,000 of potential cash boot left over. She

00:24:36.569 --> 00:24:38.369
doesn't want to pay tax on it. She can put that

00:24:38.369 --> 00:24:41.950
leftover $100 ,000 into a DST. Oh, so you can

00:24:41.950 --> 00:24:44.490
mix and match. Exactly. It's a great filler to

00:24:44.490 --> 00:24:46.809
soak up excess equity so you don't pay tax on

00:24:46.809 --> 00:24:49.009
the scraps. We've covered the how, the what,

00:24:49.109 --> 00:24:51.230
and the traps. Now let's talk about the why.

00:24:51.869 --> 00:24:54.009
Why go through all this torture? Why not just

00:24:54.009 --> 00:24:57.230
pay the tax and be free? The math has to be compelling.

00:24:57.490 --> 00:25:00.259
It is the math of compounding. Let's do a simple

00:25:00.259 --> 00:25:04.740
comparison. Sarah has a $500 ,000 gain. If she

00:25:04.740 --> 00:25:07.079
pays the tax, let's say 20 % federal capital

00:25:07.079 --> 00:25:12.180
gains, 3 .8 % NII tax, maybe state tax, plus

00:25:12.180 --> 00:25:15.440
depreciation recapture, she might lose 30 % of

00:25:15.440 --> 00:25:19.400
that gain. So $150 ,000. $150 ,000. Gone. Poof.

00:25:19.539 --> 00:25:22.819
So she only has $350 ,000 of equity to reinvest.

00:25:23.539 --> 00:25:27.740
If that grows at 7 % for 20 years, she ends up

00:25:27.740 --> 00:25:30.400
with a certain number. But if she keeps the full

00:25:30.400 --> 00:25:33.960
$500 ,000 working, that extra $150 ,000 is also

00:25:33.960 --> 00:25:38.019
growing at 7 % for 20 years. The difference isn't

00:25:38.019 --> 00:25:40.599
just the tax saved. It's the growth on the tax

00:25:40.599 --> 00:25:43.140
saved. It's the snowball effect. Exactly. Over

00:25:43.140 --> 00:25:45.180
a lifetime, the difference can be millions of

00:25:45.180 --> 00:25:47.440
dollars. It's the difference between being comfortable

00:25:47.440 --> 00:25:50.819
and being wealthy. But eventually... The tax

00:25:50.819 --> 00:25:54.180
man comes, right? If Sarah sells that final apartment

00:25:54.180 --> 00:25:56.859
complex when she's 80, she owes all the back

00:25:56.859 --> 00:25:59.220
taxes from every single exchange she ever did.

00:25:59.400 --> 00:26:02.059
If she sells, yes. But if she doesn't sell? Here

00:26:02.059 --> 00:26:04.480
it is. The swap till you drop strategy. It's

00:26:04.480 --> 00:26:07.599
the ultimate loophole. Under current law, when

00:26:07.599 --> 00:26:10.400
you die, the cost basis of your assets gets stepped

00:26:10.400 --> 00:26:12.880
up to the fair market value at the date of your

00:26:12.880 --> 00:26:15.359
death. Explain basis one more time for the non

00:26:15.359 --> 00:26:17.799
-accountants. Basis is basically what you paid

00:26:17.799 --> 00:26:20.940
for the property. If you bought for $100K, your

00:26:20.940 --> 00:26:23.519
basis is $100K. If it's worth a million, your

00:26:23.519 --> 00:26:27.079
taxable profit is $900 ,000. Okay, got it. So

00:26:27.079 --> 00:26:30.299
Sarah has been swapping for 40 years. Her basis

00:26:30.299 --> 00:26:32.400
is incredibly low because she kept carrying it

00:26:32.400 --> 00:26:35.099
forward. She might have a property worth $10

00:26:35.099 --> 00:26:38.539
million with a basis of $500 ,000. If she sold

00:26:38.539 --> 00:26:40.640
the day before she died, she would owe millions

00:26:40.640 --> 00:26:44.299
in tax. Right. But she dies. Her heirs inherit

00:26:44.299 --> 00:26:47.190
the property. The law says, OK, the new basis

00:26:47.190 --> 00:26:50.029
for the heirs is $10 million. The current value.

00:26:50.190 --> 00:26:52.549
The current value. So if the heirs sell it the

00:26:52.549 --> 00:26:55.730
next day for $10 million, $10 million sale price

00:26:55.730 --> 00:26:59.430
minus $10 million basis equals zero gain, zero

00:26:59.430 --> 00:27:02.750
tax. So all that deferred tax decades of it just

00:27:02.750 --> 00:27:05.710
evaporates. Gone. Wiped clean. The heirs get

00:27:05.710 --> 00:27:08.839
the full value tax -free. That is staggering.

00:27:09.079 --> 00:27:11.500
It effectively means capital gains tax is voluntary

00:27:11.500 --> 00:27:13.819
for real estate investors as long as they never

00:27:13.819 --> 00:27:16.059
cash out during their life. Correct. It is a

00:27:16.059 --> 00:27:18.559
massive incentive to hold property forever. And

00:27:18.559 --> 00:27:19.980
that leads to the provocative thought I want

00:27:19.980 --> 00:27:21.900
to end on. We've talked about how great this

00:27:21.900 --> 00:27:24.500
is for Sarah, for our investor. But what does

00:27:24.500 --> 00:27:27.180
this do to the rest of the world? If every investor

00:27:27.180 --> 00:27:30.039
is incentivized to swap till they drop, to never

00:27:30.039 --> 00:27:32.920
actually exit the market, it freezes the market.

00:27:33.470 --> 00:27:36.410
Think about it. In a normal market, prices go

00:27:36.410 --> 00:27:38.809
up, people sell, they take their cash, they buy

00:27:38.809 --> 00:27:41.710
a boat, and new inventory opens up for young

00:27:41.710 --> 00:27:44.910
families or new investors. But Section 1031 encourages

00:27:44.910 --> 00:27:47.750
hoarding. It does. It encourages the old guard

00:27:47.750 --> 00:27:50.710
to keep circulating properties amongst themselves.

00:27:51.109 --> 00:27:53.910
I sell my apartment to you, you sell your strip

00:27:53.910 --> 00:27:58.049
mall to me. We both defer taxes, but neither

00:27:58.049 --> 00:28:00.990
of us releases the asset to the open market in

00:28:00.990 --> 00:28:03.049
a way that creates liquidity for a newcomer.

00:28:03.259 --> 00:28:04.920
So when you drive through your city and you see

00:28:04.920 --> 00:28:07.079
those same families owning the same blocks for

00:28:07.079 --> 00:28:10.160
50 years. It's not just sentimental. It's tax

00:28:10.160 --> 00:28:12.640
strategy. Section 1031 is a brilliant wealth

00:28:12.640 --> 00:28:15.160
builder. But it might also be a contributor to

00:28:15.160 --> 00:28:17.240
the inventory shortage we see in housing. That

00:28:17.240 --> 00:28:19.819
is a heavy thought. It's a tool, but tools have

00:28:19.819 --> 00:28:21.839
consequences. They do. But for the listener,

00:28:21.920 --> 00:28:24.819
for Sarah, for Tom, the tool is there. And if

00:28:24.819 --> 00:28:26.940
you don't use it, you are voluntarily giving

00:28:26.940 --> 00:28:29.079
away 30 % of your wealth every time you trade

00:28:29.079 --> 00:28:32.779
up. So the lesson is, use the tool. But respect

00:28:32.779 --> 00:28:35.720
the tool. Get a QI. Watch the calendar. Don't

00:28:35.720 --> 00:28:39.240
touch the cash. And maybe, just maybe, don't

00:28:39.240 --> 00:28:41.140
try to claim your beach house as a business trip

00:28:41.140 --> 00:28:43.700
unless you really like auditing. And please leave

00:28:43.700 --> 00:28:45.279
the cows out of it. Leave the cows out of it.

00:28:45.339 --> 00:28:46.740
Thanks for diving in with us. We'll see you on

00:28:46.740 --> 00:28:47.119
the next one.
