Confessions of a MicroStrategy Investor

A letter no one asked for, but everyone should read before handing their Bitcoin dreams to a man in an orange tie.

—

Dear Fellow Bag-Holders, Future Therapists, and Anyone Still Pretending This Was “Strategic,”

I write to you today not as a proud MicroStrategy shareholder, but as a man who has stared directly into the mirror and whispered the words:

“Bro… what have you done?”

Look—I’m not embarrassed that I invested in Bitcoin. Magical internet money is fine. It’s pure. It’s incorruptible. It’s literally math wrapped in electricity. Beautiful.

I am, however, deeply embarrassed that I gave a company with salaries, leases, marketing teams, HR reps, and a snack budget my money… so they could buy that same magical internet money at a premium, wrap it in a corporate costume, and then somehow—somehow—turn it into something that trades at a discount.

A discount.

On Bitcoin.

In a Bitcoin bull market.

Amazing. Inspirational, even. If there were an Olympic event for turning alpha into coupons, MicroStrategy would sweep the podium.

Do you know how helpless you feel when your investment thesis boils down to:

“I believe in Bitcoin so much I outsourced it to a business with overhead.”

That’s like loving organic vegetables so much you hire a Fortune 500 company to grow them for you under fluorescent lights, at 4× the cost, while their interns eat half the crop.

And yes, yes, I get it—leverage, strategy, blah blah blah. But when your CEO has to juggle debt payments, stock issuance, Twitter theatrics, and a line item called “orange tie dry-cleaning,” you start to wonder:

Was I investing in Bitcoin… or in the world’s most complicated meme account?

At this point, even my Bitcoin-hating uncle respects me more than my financial advisor does. At least the uncle says he bought gold once because “it was shiny.” My excuse? I thought buying a corporate wrapper around Bitcoin was “efficient.” Efficient at what? Converting sats into operating expenses?

If I wanted discounted Bitcoin, I should’ve just bought Bitcoin.

If I wanted chaos, I could’ve bought a shitcoin.

Instead, I bought a stock that somehow blended both worlds. A schrödinger’s tradfi-wrapped-Bitcoin derivative that lives in a simultaneous state of premium and embarrassment.

So here I stand—an MSTR shareholder.

A man who believed.

A man who delegated.

A man who now understands that true self-sovereignty means never relying on a corporate board to stack for you.

Godspeed to us all.

And please—next board meeting—cut the marketing budget before the coupons.

Sincerely,

A Recovering MicroStrategy Apologist

P.S. If anyone needs me, I’ll be buying the underlying asset directly like a grown adult.