In A Slightly Alternate Reality, Bill Gates Would Have Become The World's First Trillionaire Two Years Ago

As you may have heard, on the afternoon of Thursday, June 11, 2026, Elon Musk became the world's first trillionaire.

That is an absolutely stunning sentence to write. For most of modern history, the idea of a private citizen reaching a 13-digit net worth felt like pure science fiction. A trillion dollars is not merely "a lot of money." It is a number so large that it barely makes sense in human terms. It is 1,000 billions. It is more than the annual GDP of most countries. It is a level of personal wealth that would have been unimaginable even to the Rockefellers, Carnegies, Vanderbilts, and Astors of previous eras. Elon's $1 trillion net worth makes him the richest human being of all time by a mile, even after adjusting for inflation.

An incredible achievement. A mind-bending milestone. A genuine first in the history of private wealth.

But there's a catch…

In a slightly different reality, the world would have seen its first trillionaire two and a half years ago, in January 2024.

That person was not Elon Musk.

It was Bill Gates.

Or at least, it would have been Bill Gates had he ignored some absolutely terrible financial advice from Warren Buffett…

Bill Gates and Phoebe Gates (Photo by Dimitrios Kambouris/Getty Images for TIME)

Going Back In Time

Microsoft went public on March 13, 1986. On the day of the IPO, Bill Gates owned 45% of the company's equity. At the end of its first day as a public company, Microsoft's market cap was $780 million. Therefore, Bill ended the first day of trading with a paper net worth of $350 million.

Funnily enough, Bill was vacationing in Australia on the day of the public offering, arguably the most important financial day of his life. When he returned, his big splurge as a newly-minuted hundred millionaire was to pay off the mortgage on his Seattle house. Roughly a year after going public, Bill became a billionaire for the first time as Microsoft's share price continued to flourish. He was 31.

A Chance Meeting

Today, Bill Gates and Warren Buffett seem like they have been friends forever. But that's not the case. The two billionaires met for the first time in 1991 at a Fourth of July barbecue held at Bill's parents' house in Seattle. Warren happened to be in Seattle to meet with a friend, and that friend happened to know Bill's parents. She offered to make an introduction and literally drove Warren over to Bill's parents' house so the two moguls could shake hands in person.

Bill was wary about meeting Warren. As he would later explain:

"I didn't even want to meet Warren because I thought, 'Hey, this guy buys and sells things, and so he found imperfections in terms of markets — that's not value added to society, that's a zero-sum game that is almost parasitic."

His attitude quickly changed after Warren peppered him with "amazingly good questions that nobody had ever asked." They hit it off, and a lifelong friendship and future mutual devotion to philanthropy was born.

Considering Warren's business philosophies, it's very likely that one of those "amazingly good questions" he posed to Bill was something along the lines of "how are you planning to diversify your net worth?"

Warren Buffett became a billionaire thanks to his diversified investment holding company, Berkshire Hathaway. Berkshire Hathaway has a market cap today of $800 billion. In addition to owning the majority of dozens of companies like GEICO, Fruit of the Loom, and See's Candy, Berkshire also owns large stakes in hundreds of publicly traded and private companies. This diversified strategy has led to a 19% average annual compound gain for Berkshire's shareholders since 1965. Diversification is a foolproof strategy against risk. Or, to quote the Oracle of Omaha directly, "Diversification is protection against ignorance."

In July 1991, Bill Gates' net worth would have been around $2.5 billion. Nearly 100% of his net worth came from his stake in Microsoft.

Following Warren's advice, Bill began to diversify. He established his own private investment firm, Cascade Investments, and funded it with billions of dollars generated by the sale of his Microsoft shares. By 2000, when he retired as CEO, Bill Gates' stake in Microsoft had shrunk to 14%.

Today, Bill Gates is believed to own roughly 103 million Microsoft shares, equal to a little less than 1.4% of the company. That figure comes from his last major public disclosure before he stepped down from Microsoft's board, and his exact current personal stake is no longer regularly disclosed. He is not Microsoft's largest individual shareholder. That honor belongs to his successor, Steve Ballmer, who owns around 4% of the company.

The remainder of Bill's fortune comes thanks to his diversified investments controlled by Cascade. Through Cascade, Bill owns hundreds (potentially thousands) of significant stakes in public and private companies. He is also the majority owner of the Four Seasons Hotel and Resorts chain and is the largest private owner of farmland in the United States.

One could argue that following Warren Buffett's diversification advice was very wise for Bill Gates. Microsoft has had many ups and downs over the decades, but his diversified fortune allowed him to stay the richest person in the world pretty much uninterrupted between 1997 and 2008.

But what if he had ignored Warren's advice?

World's First Trillionaire

As we stated earlier, on the day Microsoft went public, March 13, 1986, Bill Gates owned 45% of the company's equity. It's only natural that he would have sold off some of that equity over time. Perhaps with share sales to give himself some liquid wealth, he would have reduced his stake to 40% or 35%. Let's use 35%. If Bill Gates still owned 35% of Microsoft, in January 2024, when Microsoft first reached a market cap of $2.887 trillion, that stake would have been worth:

$1.01 trillion

And if that's not mind-blowing enough, if he still owned 35% of Microsoft, thanks to the company's $3-per-share dividend, every year Bill would receive around $9 billion every year in dividend payments.

I can hear the skeptics now: "There's no way Bill Gates would have ever maintained such a huge ownership stake in Microsoft…" To those skeptics, I offer the following counterpoint: Larry Ellison

Larry Ellison is the founder and CEO of Oracle. Oracle went public on March 12, 1986. That's one day before Microsoft's IPO. On the day of the IPO, Larry owned 39% of Oracle's equity. After various share buybacks and personal purchases over the decades, today Larry owns… 42% of Oracle.

Oracle's current market cap is $530 billion. Larry's 42% stake equates to $223 billion in paper wealth. Larry has at least $10 billion worth of his shares pledged as collateral. Larry also owns 1.4% of Tesla. That stake is worth around $9 billion. Taking into account various other assets and debts, today Larry Ellison's net worth is $214 billion. And depending on how you slice it, pretty close to 99% of his fortune comes from his Oracle stake. So, if Oracle's market cap were to grow to $2.381 trillion, Larry would be a trillionaire.

By the way. One of the assets Larry Ellison acquired through his wealth is the Hawaiian island of Lanai. Larry bought Lanai in 2012 for $300 million. With the purchase, he also acquired the island's primary attraction, the Four Seasons Resort Lanai (he has since built a second Four Seasons on the island). If you'll recall, Bill Gates owns the majority of the Four Seasons corporation. How does that work? Four Seasons doesn't actually own any of its hotels; it operates them on behalf of owners such as Larry. So Larry and Bill are partners in a way. And in a fun twist, when Bill married his now ex-wife, Melinda Gates, in 1994, they rented out the entire Manele Bay Hotel… which in 2005 was renamed… the Four Seasons Resort Lanai! One final fun fact: To prevent helicopter paparazzi from ruining his wedding, Bill rented all the helicopters on both Lanai AND Maui for his entire wedding weekend 🙂

Could Steve Jobs Have Become A Trillionaire?

With Apple sitting at a still-impressive (but second-place) $2.874 trillion, would Steve Jobs be a trillionaire today if he were alive? The short answer is no. Not by a long shot.

At the time of his death, Steve Jobs' net worth was $10.2 billion. Counterintuitively, 80% of his net worth came from Disney stock he received from the sale of Pixar. Thanks to some twisting and turning circumstances, Apple stock only represented around $2 billion of his fortune.

When Apple went public in December 1980, Steve Jobs owned 20% of the company's equity. Steve was ousted in an infamous boardroom coup in 1985. In anger, he immediately sold all but a single share in the company, earning a pre-tax windfall of $100 million. He kept a single share so he could continue receiving annual reports and attend shareholder meetings, if he had the desire. When he was brought back as CEO in 1997, Steve owned essentially zero shares of the company he founded. To motivate and attract him, he was richly rewarded with many Apple shares and options. At the time of his death in 2011, he owned 5.5 million shares of Apple, less than 1% of the total outstanding shares.

If Steve kept his 20% stake, it would have been worth $400 billion in August 2020 when the company first crossed the $2 trillion market cap mark. Apple's market cap has been above $3 trillion on several occasions, as recently as last month. A 20% stake of $3 trillion would be worth $600 billion. For this hypothetical Steve Jobs to become a trillionaire, Apple's market cap would need to be $5 trillion.