7 Things We Learned From Michael Saylor’s Forbes Feature

Michael Saylor has appeared on the front cover of Forbes — with a write-up describing MicroStrategy as a “revolution in corporate finance.”

You can’t help but draw parallels to the fawning feature devoted to Sam Bankman-Fried back in October 2021, when the magazine’s journalists drooled over “the richest twenty-something in the world.”

Look how all of that turned out.

The Forbes piece documenting Saylor’s ascendancy begins on New Year’s Eve — and describes an extravagant party at his Miami Beach estate, with plenty more revellers aboard a 154ft superyacht on the water.

“Here, Bitcoin is God — and Saylor is the prophet,” author Nina Bambysheva writes.

To be fair, this Bitcoin billionaire isn’t given an entirely free pass in this article. Space is devoted to critics who claim MicroStrategy is exploiting an “infinite money glitch” that will collapse if BTC prices crumble.

Here are seven things we learned.

1. The 21/21 Plan is Working

This relates to MicroStrategy’s plan, unveiled last October, to raise $42 billion over three years to buy as much Bitcoin as possible — 50% through equity, and 50% through debt. According to Forbes, the company acquired 200,000 BTC at a cost of $18 billion in the final two months of 2024 alone.

2. MicroStrategy Should Survive a Bear Market

Given the staggering levels of borrowing that MSTR has engaged in since it began aggressively adding Bitcoin to its balance sheet in August 2020, skeptics have long wondered whether the company would be able to survive a punishing crypto winter without dumping its reserves.

But Forbes says that — “unless it’s a true apocalypse” — the business intelligence firm would only find itself in hot water if BTC plunged below $20,000 and remained there for a two-year period. That’s unlikely given the very worst of crypto bear markets don’t tend to last this long.

It’s also worth noting that MicroStrategy has weathered storms like this before. Saylor was unwavering when Bitcoin prices tumbled in 2022 and 2023 in the wake of Terra, Celsius and FTX going under. At one point, the company’s paper losses amounted to billions.

3. Forced Liquidations Are Also Unlikely

Bitwise analyst Jeff Park told the magazine that, in his view, it’s unlikely that MicroStrategy would find itself in a position where it needs to dump vast amounts of BTC on the market.

Not only does Park believe that the company actually has very little debt on its balance sheet — with MicroStrategy’s current share price meaning about $4 billion is “in the money” — but argues that institutional bondholders “have high tolerance for refinancings” anyway.

4. Other Firms Are Trying (and Failing) to Copy MSTR

Forbes notes that other major companies are attempting to take a leaf out of MicroStrategy’s book — about 90 by some estimates — but all lack Saylor’s first-mover advantage, not to mention the sheer scale of Bitcoin holdings.

The latest figures suggest MSTR now holds 471,107 BTC — that’s 2.243% of the 21 million that will ever exist. Mining company MARA Holdings is in a distant second with 44,893 BTC, which isn’t even 10% of Saylor’s warchest.

5. Saylor Isn’t Interested in What Critics Have to Say

The feature attempts to put some of the concerns raised by skeptics to Saylor directly — to which the billionaire simply states that the conventional wisdom of volatility being a bad thing is wrong. “They’re living in flatland, a pre-Copernican world,” he shrugs.

An interesting bit of color at this point in the article: he has three parrots called HODL, Satoshi and Max.

6. He’s Lived Through Boom and Bust Before

The latter end of the piece rewinds to early 2000, when MicroStrategy’s share price ballooned to $313 before crashing to $72, adding:

“Within two years its stock price had fallen below $1. Saylor’s $13 billion fortune evaporated.”

It’s interesting to see the 59-year-old genuinely show remorse here — and he’s quoted as saying:

“It was the darkest part of my life. When people lose money because they believe in you, that’s pretty much the worst.”

Never sell your Bitcoin.

— Michael Saylor⚡️ (@saylor) February 2, 2025

7. Bitcoin is a ‘Lesson in Humility’

It’s also interesting to see Saylor show a little vulnerability perhaps — with the entrepreneur noting that 20 things he invented didn’t change the world, but a digital asset created by someone else did.

“That, ironically, has made me more successful than me trying to commercialize every one of my own ideas.”

Saylor concludes by saying that MicroStrategy’s Bitcoin journey began out of “frustration and desperation” — before evolving from an opportunity, to a strategy, to an identity, and finally, a mission.

Now in the role of executive chairman, giving him more time to evangelize on the benefits of Bitcoin — including in front of Microsoft’s board of directors late last year — the next two years will be hugely consequential for Michael Saylor… one way or another.