Billionaire who made $15B using ChatGPT reveals one rule to find your 'magic opportunity'
We've pitched the idea before, but what would you do with a time-traveling DeLorean? Back to the Future II's villainous Biff Tannen uses a Grays Sports Almanac to go back in time and bet on major sporting events to make his fortune, but if you had a time machine in real life, you'd be wise to go back and bet big on the likes of Facebook, Apple, or Nvidia.
This was even a plotline in Forrest Gump, showing that his Apple shares would be worth a not-so-small fortune these days. More recently, there's been the Bitcoin boom, with the popular cryptocurrency taking off. This is why the search for Bitcoin founder Satoshi Nakamoto constantly goes viral, with his reported 968,452 BTC being worth $61,988,733,723 (at the time of writing).
One man who knows all about Bitcoin is billionaire Michael Saylor, who's seen his wealth soar since his software company, Strategy, pivoted to a Bitcoin accumulator in 2020. This means Saylor's wealth swings with the price of Bitcoin, and considering the currency is down around 30% from the start of 2026, that's not great news for his bank balance. It's not just the crypto pie that Saylor has his hand in, with Forbes reporting he's jumped on the AI bandwagon and amassed a jaw-dropping $15 billion through ChatGPT.
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As for what gives Saylor this apparent Midas touch, he says you need to look for your 'magic opportunity'. Speaking to Steven Barlett's Diary of a CEO podcast, Saylor referred to how Mark Zuckerberg got in with Facebook just at the right point of the internet and explained: "What you want to do, if you want to create these incredible success things, is you want to locate the magic opportunity right at the right point on the S-curve where it just now became commercially viable to do it."
Referring to it as a zero-to-one moment, Saylor continued: "You want to be the first person that applies that technology to this new idea. What did our company do to go from nothing to $60 billion, or from $1 billion to $60 billion?
"We were the first company to take digital capital Bitcoin and put it together with digital credit and a digital treasury model. So we created a credit instrument, a security that you could never have created before."
Singing Strategy's praises, Saylor says he needed $10 to $20 billion in capital to build it into a multi-billion dollar company that became resonant. Still, there was an elusive window of between 12 and 24 months: "You go through that window, and you create something that might be a hundred-billion-dollar thing because you go through. If you went through it 36 months early, you smack into a wall, and you fail."
He also warned you can't wait either, saying that his company is 20 times bigger than the next biggest one, 50 times bigger than another doing something similar. Saylor concluded that they didn't plan it but simply created this 'extraordinary' thing: "We committed to it with all of our heart and soul, and we declared we were going to make it work come hell or high water...
"We got punched in the face a hundred times, and every single time we ran into a problem, we stopped, we recalibrated, we went a different direction...
"So if you can figure out how to give people this thing they want with a new technology that was impossible, that did not exist five years or three years earlier, then you resonate in society."
Elsewhere in the podcast, Saylor told Bartlett how he made $15 billion thanks to ChatGPT in 2025 and sold some Bitcoin to 'inoculate' the market while funding its debt and dividend commitments.
With Strategy's common stock plunging alongside the price of Bitcoin and losing around 80% of its value, Saylor has pivoted.
Taking to X, Bill Barhydt, the chief executive of bitcoin and crypto wealth platform Abra, wrote: "History will show this as absolutely brilliant financial engineering in a major late-stage U.S. debt cycle."
By the looks of it, Saylor will continue to ride the various tech booms looking for his 'magic opportunity'.