Is Michael Saylor Overdoing the Bitcoin Buying? Strategy Is Back at It Again…

Michael Saylor isn’t slowing down. His company, Strategy (MSTR), has quadrupled a previously planned $250 million capital raise, announcing a new $1 billion preferred stock offering to keep feeding its Bitcoin habit. The stock, dubbed Series A Perpetual Stride Preferred, will pay a juicy 10% dividend — but that comes with strings.

Why? Because unlike past raises via common stock or convertible bonds, this is a special kind of financing aimed at professionals and institutions. The structure gives Strategy money now without diluting common equity right away — but locks the company into hefty dividend payouts to high-powered investors.

The stated purpose? Buying more Bitcoin, of course. At current prices (~$104K per BTC), this raise could fund up to 9,600 more coins — more than 13x the size of Saylor’s last $75 million buy earlier this week.

What’s Really Driving This — Vision or Leverage Addiction?

On paper, it’s a daring, high-conviction bet. But under the hood, it looks more like a doubling down with increasing leverage. Saylor already holds more Bitcoin than any other public company on Earth — over 226,000 BTC, worth nearly $24 billion. So why raise nearly a billion more to buy at these levels?

There are two likely answers:

1. He thinks Bitcoin isn’t even close to topping.
2. He’s so far in, he can’t afford to stop.

This is where it starts to resemble a feedback loop. The more Bitcoin Strategy owns, the more committed it is to propping up sentiment. If Bitcoin dips, Strategy’s equity sinks — and future raises get harder. If it climbs, well… rinse and repeat.

But there’s risk in betting the house this late in the cycle. With Bitcoin already more than 35% off April lows, it’s no longer cheap. And a $1B purchase at these levels is hardly early-mover magic — it’s chasing momentum. That’s not a problem, unless momentum breaks.

Clever Finance, But Not Without Cost

Here’s what makes this deal different. Preferred shares like these sit above common equity in the capital structure. They’re not debt, but they behave a lot like it — offering a fixed 10% dividend and no voting rights.

This allows Saylor to raise capital without further diluting common shareholders (yet), but it locks him into a non-cancellable 10% payment stream to institutional buyers. That’s great if BTC goes to $200K+. But if it stalls, Strategy is paying steep interest on a bet that doesn’t deliver — and those costs don’t go away.

It’s risky game. Either Bitcoin keeps ripping, or Strategy’s balance sheet starts to strain under its own ambition.

Will This Make Bitcoin Holders Rich, or Just Help Saylor Save Face?

Strategy’s move has broader implications for the Bitcoin market. If you’re a retail holder, this seems bullish — another giant scoop of institutional demand hitting the market. And sure, 9,600 BTC is no joke.

But here’s the rub: this isn’t new money flooding into the space. It’s the same buyer leveraging more capital to defend their thesis. It creates a floor — for now. But it also creates fragility. If Strategy ever has to unwind part of this position (to pay dividends, for instance), it could trigger serious downside.

This is no longer just a play for upside. It’s defense of a legacy. Saylor has become synonymous with Bitcoin’s institutional narrative, and if it falters, so does his empire.

Saylor’s belief in Bitcoin is unmatched. But the size, timing, and structure of this new $1B bet raise real questions about sustainability. It’s no longer about early conviction. It’s about how far one man is willing to go to be proven right.

Is MicroStrategy a Buy Right Now?

MicroStrategy, now rebranded as Strategy, has drawn strong support from Wall Street analysts. According to TipRanks, the stock holds a Strong Buy rating. 12 out of 13 analysts currently call it a Buy, with just one lone Sell and zero Hold ratings. The average 12-month MSTR price target sits at $524.92—implying a 42.3% upside from the recent close.

See more MSTR analyst ratings