Michael Saylor’s Bitcoin Strategy Faces New Competition
Michael Saylor has never been shy about his approach to stacking bitcoin. Through bonds, stock sales, and other financial moves, he’s built MicroStrategy into a kind of bitcoin-holding machine. The idea, at least for shareholders, is that even if their ownership gets diluted a bit, the company ends up with more bitcoin per share over time. It’s a tricky balance—some call it financial alchemy—but so far, it’s worked.
The problem? Others are catching on. In the last six months alone, over 130 new companies have popped up, listing shares on global exchanges with the same goal: growing a bitcoin treasury without wrecking shareholder value. Some are copying Saylor’s playbook. Others are trying entirely different tactics.
The Original Playbook: Selling Shares at a Premium
MicroStrategy—sometimes just called “Strategy” in finance circles—was the first to really push this method. By selling shares when their stock price was high compared to the value of their bitcoin holdings, they could buy more BTC without overly hurting shareholders. Over time, Saylor expanded beyond just stock sales, issuing dividend-paying preferred shares and other securities.
The theory is that demand from traders and retail investors keeps the prices of these securities high enough to make the math work. But now, with more companies jumping in, that demand isn’t guaranteed.
New Twists on an Old Idea
Some firms are getting creative. Instead of just selling shares, they’re selling options—contracts that give buyers the right to purchase bitcoin (or company stock) at a set price later. It’s a way to collect cash upfront, though it caps potential gains if bitcoin skyrockets. MetaPlanet, for example, has leaned into this approach, and others are following.
Then there’s the old-fashioned way: using actual profits. Companies like Tesla and Marathon Digital have bought bitcoin with cash from operations, avoiding dilution altogether. Even Tether, the stablecoin giant, has funneled some of its massive profits into BTC.
Riskier Moves: Insurance and Sale-Leasebacks
A few companies are venturing into even less conventional territory. Some insurers, like MassMutual, have started putting a slice of their premium reserves into bitcoin. Others are doing sale-leaseback deals—selling assets like real estate or equipment, then leasing them back immediately. It’s a quick way to free up cash for bitcoin, but it locks in long-term costs.
The big question now is whether Saylor’s early lead will hold. With so many competitors trying their own versions of “accretive dilution,” the game is getting crowded. And as more players enter, the strategies—and the risks—keep evolving.
