Author: Shayan Hamad

When people sell a home, they obsess over the wrong things. They repaint walls that didn’t need repainting, haggle endlessly with agents over listing price, or lie awake at night fretting about whether a buyer will notice that weird crack in the driveway.

But the biggest threat to their profit? It usually goes completely unnoticed.

Taxes.

Yes, the IRS. That faceless entity everyone dreads. And yet, right under your nose, there’s a rule designed to protect homeowners from losing thousands — sometimes hundreds of thousands — to capital gains tax. read more

Most new investors walk into the market with a portfolio and a perfectly reasonable belief:

“I only pay taxes when I sell.”

It makes sense. You buy stocks. You let them grow. You sell later. Taxes happen at the end. Clean. Logical. Comforting. Like a self-checkout lane that actually works.

And then one day, without selling a single share, you open your mail—or inbox—and find a tax form politely informing you that you owe money. No trades. No clicks. No mistakes you can remember.

Just… taxes. read more

Inheriting property is one of those strange moments in life where grief, gratitude, and spreadsheets all collide at once.

On one hand, you’re dealing with the emotional weight of losing someone. On the other, you’re suddenly holding a house, land, or investment that comes with paperwork thick enough to qualify as a workout. Somewhere in the middle, a quiet but persistent thought creeps in:

“How much of this is the IRS going to take?”

Here’s the comforting truth most people never hear upfront:
Inherited property is usually far more tax-friendly than people expect. read more

You’ve poured years into your business — long nights, early mornings, questionable coffee choices, and a diet that was “temporarily” 80% takeout pizza.

You skipped vacations. You reinvested profits instead of upgrading your car. You told friends, “Next year will be easier.”
(It wasn’t.)

Then one day, it finally happens.

Someone wants to buy your company. For real money. Not “exposure.” Not equity in a mysterious startup. Actual dollars with commas in them.

The deal closes. You celebrate. You update LinkedIn with a tasteful but dramatic “On to new horizons 🌅.”
Life is good. read more

After years of grinding—growing a business, managing rental properties, or holding onto an asset that finally did the thing—selling feels like a win. A big one. Champagne energy. Relief. Validation.

Then capital gains tax walks into the room like an uninvited relative who eats first and talks loud.

Suddenly that victory lap feels… shorter.

Smart entrepreneurs learn early that wealth isn’t just about making money. It’s about what you keep, how long you keep it, and what you let it do before taxes take a bite. That’s where capital gains deferral comes in—not as a loophole, not as a trick, but as a strategy rooted in time, reinvestment, and compounding. read more

You feel inflation every day, even if you don’t use the word for it.

Your grocery bill creeps up.
Fuel prices refuse to behave.
Rent laughs at your budget spreadsheet.

Inflation is that slow leak in the tire of your financial life — never dramatic, always annoying, and somehow expensive.

But there’s a sneakier place inflation hits that most investors don’t realize until it’s too late: your capital gains tax.

Here’s the uncomfortable truth:
You can pay taxes on profits that don’t actually exist in real purchasing power. read more

You finally decide to sell a family heirloom.

Maybe it’s a painting that’s been hanging in the living room since before you were born. Maybe it’s your grandfather’s watch collection, a box of rare coins, or a piece of jewelry that only comes out during weddings and holidays.

You’re not thinking about taxes. You’re thinking about value. Cash value, emotional value, maybe even relief. Then, a few weeks after the sale, reality taps you on the shoulder wearing an IRS badge.

Yes, even sentimental items can trigger capital gains tax. And for a lot of people, that realization arrives late, loud, and expensive. read more

You don’t need a hedge fund, a trust fund, or a yacht named after a Greek god to run into capital gains tax.

You just need to sell something that went up in value.

Sell your house.
Unload a rental property.
Cash out stocks after a good run.
Flip crypto at the wrong time.

And suddenly the IRS appears like that one friend who never replies to texts—but always knows when money is involved.

Here’s the part most people never get told, but we will, in the Guide: capital gains tax is one of the most controllable taxes you’ll ever pay. Not because of loopholes or sketchy tactics, but because the tax code intentionally rewards certain behaviors—holding assets longer, reinvesting profits, owning property, and thinking ahead before you sell. read more

Marriage changes a lot of things.

Suddenly, you’re coordinating calendars. Negotiating thermostat settings like diplomats. Accidentally eating your spouse’s leftovers and pretending you thought they were “community property.”

But one of the quietest—and most financially powerful—changes marriage brings has nothing to do with romance or routine.

It’s taxes.

Specifically, capital gains taxes.

Most couples never realize this, but the U.S. tax code treats married households very differently from single individuals. When you sell a house, cash out stocks, or unload an investment property, marriage isn’t just a relationship status. read more

Most people think owning rental property is simple math.

Rent comes in.
Expenses go out.
What’s left is profit.

That’s the visible layer — the part you see on a spreadsheet or a bank statement.

The real magic, the kind that quietly builds long-term wealth, lives somewhere far less exciting but infinitely more powerful: the tax code.

Rental property isn’t just an income-producing asset. It’s one of the most tax-advantaged investments available to regular people. It allows you to earn money while legally reducing taxable income, deferring taxes for years, and in some situations eliminating them entirely. read more