I Need Cash — But I Refuse to Sell My Stocks

In March of 2027, I have a balloon payment coming due on an oceanfront villa. And I'm not selling a single share of stock to pay it.

There's a strategy the internet loves to be angry about: Buy, Borrow, Die. The pitch is always the same — this is how billionaires never pay taxes, the system's rigged, look how unfair it all is. Here's my problem with that framing: nobody making that video is actually doing it.

I'm not a billionaire. I'm a guy with a deadline. And I'm about to use that exact strategy for a completely boring reason. So let me show you the real thing — what it is, why I picked it over two other options I had sitting right there, and the part that genuinely keeps me up at night, because this has a risk nobody making those angry videos ever mentions.

The Strategy the Internet Loves to Hate

Forget billionaires for a second, because the concept is something you already understand.

You know what a HELOC is. Home equity line of credit. You own a house, the house is worth something, and instead of selling it to get at that value, a bank gives you a line of credit against it. You keep the house. You keep living in it. If it goes up in value while you're borrowing, that's still yours. You just pay interest on whatever you actually draw.

That's it. That's the whole idea.

Now swap the collateral. Instead of the house, it's your brokerage account. Same structure — you pledge the securities, the lender gives you a line of credit against them, you keep owning the shares, you keep collecting the dividends, and you pay interest only on what you actually pull.

That's called a securities-backed line of credit. And the "buy, borrow" part of Buy, Borrow, Die is really just this. It's a HELOC where the house is your portfolio.

The reason billionaires get accused of gaming the system with it is that borrowed money isn't income. You didn't sell anything, so there's no sale to tax. That's not a loophole somebody snuck in — that's just what a loan is. When you take a HELOC on your house, nobody calls that tax evasion.

My Actual Situation

Here's my real situation, and I'll be specific, because the specifics are the whole point.

I own a piece of an oceanfront villa in the Dominican Republic with a business partner. I've had it for about four and a half years. It runs as a short-term rental, and it does well.

Here's the part most Americans don't know. When you buy real estate down there, a lot of it is owner-financed — the seller carries the paper. A really common structure, and the one I have, is a five-year loan amortized over twenty years.

Read that again, because that's the trap. Your payment is calculated like it's a twenty-year loan, so it feels comfortable, feels affordable. But the loan itself is only five years. Which means at the end of year five, everything that's left comes due at once. That's a balloon.

Mine hits March of 2027.

Here's the thing about a balloon — it's not a surprise. I've known this date since the day I signed. The mistake people make isn't taking the loan. It's showing up at year four and eleven months with no plan. A balloon payment is a problem you solve in advance, or it solves you. I started working on this over a year ago.

Why Not Just Refinance?

First question everybody's already thinking: Mikey, you own other real estate, why not just refinance?

Start with the villa itself, because that one isn't even on the table. Banking in the Dominican Republic doesn't work the way it works here. There aren't many traditional US banks operating down there, and being a US citizen makes conventional mortgage financing on that property difficult and expensive in a way most Americans don't expect. That's exactly why so much real estate down there gets sold with owner financing in the first place — the seller carries the paper because the bank isn't going to.

Okay, so what about here at home? I own a condo that's almost paid off, with serious equity in it. On paper, that's the obvious move: pull a HELOC or refinance, use that money, done. And honestly, that's still my Plan B.

But it's not my Plan A, and here's why. A refinance is a whole process — appraisal, underwriting, income documentation. I'm self-employed with multiple businesses, which means my paperwork isn't the clean two-pay-stubs version a bank wants. Closing costs, weeks of back and forth, a stack of documents at the end.

A line against the portfolio is set up once, and then it just sits there. It's revolving — I draw what I need when I need it, pay interest only on what I actually drew, and can pay it down and draw again. No appraisal on a property. No underwriter deciding how they feel about a guy who owns six businesses. When you've got a hard date in March, the thing that can move fast is worth something.

Why Not Just Sell the Stock?

Second question: just sell some stock, Mikey. You've got the shares. Sell them, pay the villa off, no debt, no drama.

I thought about it seriously. Three reasons I didn't.

One — taxes. If I sell appreciated shares, I trigger a taxable gain that year. That's real money leaving to solve a problem that doesn't require it. I want to be careful here — I'm not a tax pro, the rules depend on your situation, talk to somebody licensed. But the general shape is simple: selling creates a tax event; borrowing doesn't.

Two — compounding. Those shares have been working for years. The second I sell them, that engine stops for that chunk of money, permanently. I don't get to un-sell it later at the price I sold it at.

Three, and this is the one that actually decides it for me: selling shares to solve this problem ends the income stream to fix something temporary. The balloon is a one-time event. The dividends are forever. Trading forever for one-time is a bad trade, and it's the exact opposite of everything I've built this portfolio to do.

I want to say this plainly, because it's the honest core of the whole decision. The peace of mind is worth more to me than a few percentage points. Somebody's going to run the math in the comments and show me a spreadsheet where selling wins by some margin. They might even be right. I don't care. This property is real wealth; it's a long-term asset, and securing it matters more to me than optimizing the last couple percent.

The Third Word

So that's buy, and that's borrow. What about die? That's the word that makes everybody mad.

Quick and plain. Under current tax law, when your heirs inherit your appreciated assets, the government basically hits the reset button on the gains you built up over your whole life. Your kids don't inherit your tax bill along with the shares. That's called a step-up in basis.

So wealthy families borrow against assets instead of selling them, and then never unwind the loan. They hold to the end.

That's the real strategy, and it's not why I'm doing this — I've got a payment due in March of 2027, and I plan to pay this off, not carry it to my grave. But I'd be skipping something if I explained the first two words and ignored the third. Tax law changes. I'm not a tax professional. Talk to one.

The Risk Nobody Mentions

Now, I know how that sounds. It sounds like a cheat code. And it is — right up until the market drops. Because this thing has a kill switch, and almost nobody explaining the strategy ever mentions it. If you take one thing out of this post, take this.

I've spent months telling you that the whole point of dividends, for me, is that I never get forced to sell. Market tanks, I don't care; the checks still come. I'm not liquidating at the bottom to pay a bill.

Borrowing against that same portfolio brings that exact risk right back in the door.

Here's how. The lender doesn't lend you the full value of your account — they lend against a portion of it. Every security has its own lendable value, and it's less than what it's worth. If the market drops far enough, the value of what you pledged falls below what's needed to support the loan, and you get what's called a maintenance call.

A maintenance call is not a friendly email. Typically you have something like two to three business days to fix it. You either put more collateral in or pay the balance down. If you don't do it in time, the lender can sell your securities to cover it — and in a lot of these agreements, you don't get to choose which securities they sell. They'll generally try to notify you, but they're often not required to.

Sit with that. A market drop, a deadline measured in days, and somebody else deciding which of my shares go. That's the exact forced sale, at the exact worst moment, that I built this entire portfolio to avoid. The strategy that protects me from being forced out can, if used wrong, be the thing that forces me out.

How I'm Handling It

I'm not going to pretend that risk away. Here's how I'm managing it.

First, I'm not borrowing anywhere near the maximum they'd give me. The single biggest thing you control is how much cushion sits between what you borrowed and where the call gets triggered. Borrowing the max means a normal correction becomes an emergency.

Second, the loan is serviced by my businesses, not by the collateral. My business income pays this down. The dividends are the backup, not the plan. That distinction is everything.

Third, I have a Plan B, and it's the condo. If March 2027 shows up in the middle of an ugly market and the portfolio's down, I refinance or take a HELOC on the condo instead. It's slower and more paperwork, which is exactly why it isn't Plan A. But it's real, it exists today, and it doesn't care what the S&P did that quarter.

Fourth, I'm spending the next six months trying to make as much as I possibly can, because cash on hand is the thing that makes every version of this easier.

And one more personal note: I lost a business once, partly because of a currency move I didn't see coming. Different situation, different decade, but it taught me to look at what my money's actually exposed to and not just the headline deal. So I checked — this note is in US dollars. I'm not sitting on a currency mismatch I haven't thought about.

Who Should Not Do This

Let me be blunt about who should not do this, because I don't want a clip of this floating around convincing somebody to blow up their account.

Suppose you're thinking about borrowing against your portfolio to buy more stock — don't. That's leverage on leverage. Market drops, your collateral falls, and the thing you bought with the money falls at the same time. That's how people get wiped out, and it's a completely different activity than what I'm describing.

If you don't have income coming from somewhere outside that portfolio — don't. This only works because my businesses pay the interest. If the only thing servicing the loan is the same account backing the loan, you've built a circle, and a bad market breaks the circle in both places at once.

If a maintenance call would end you — don't. Be honest with yourself. If the market drops hard and you get three days to come up with money, do you have it? If the answer is no, this isn't a tool; it's a fuse.

And if you're early — just don't. If you're still building the position, borrowing against it is solving a problem you don't have yet. Build the thing first.

This is a tool for a specific job. It's not a shortcut, and it's not free money. It's debt. It's just debt with better collateral.

Where This Leaves Me

So that's the plan. Balloon payment in March of 2027. Line of credit against the portfolio, well under the max, businesses paying it down, condo as the backup, and every share I own still sitting there paying me the whole time.

Am I certain it goes perfectly? No. This is my first time doing this, and plenty could go sideways. That's why I'd rather show it to you now, with the risk on the table, than come back next year with a clean story about how smart I was.

Here's what I actually think. Buy, Borrow, Die isn't a billionaire cheat code. It's a tool. And like every tool, it's only safe when the person holding it doesn't need it to work. The reason I can do this is that my income doesn't come from the collateral. If it did, I wouldn't touch it.

Real estate is a long game. I've had this property for four and a half years, and in my experience, real estate starts really paying somewhere around that five-year mark, because your payment doesn't go up, but rents generally do. Once this thing is paid off, it's a cash cow. That's the whole reason I'm protecting it instead of selling the engine that's going to help me pay for it.

The engine feeds the vault. The vault never feeds the engine.

Watch the full video above, or on YouTube: https://youtu.be/Rr5ZkdAS2ds