On July 21, 1980, three IBM executives in suits flew from Boca Raton to Seattle. Their "Project Chess" needed to ship the IBM PC within a year, and they had no operating system. Gates was 24, his company had about 30 people. He first sent IBM to Gary Kildall at Digital Research — whose CP/M was the de facto 8-bit PC operating system standard. The day IBM came calling, Kildall was out flying his plane (he was a pilot) and left his wife Dorothy McEwen to host them. McEwen refused to sign IBM's NDA. IBM flew back to Seattle.
Gates and Paul Allen did not own an operating system either. They made a decision: pay $50,000 to Tim Paterson at Seattle Computer Products for QDOS — the "Quick and Dirty Operating System" — rename it MS-DOS, and pivot. Then, in negotiations that November, Gates held the line on a single, seemingly minor clause: IBM could license MS-DOS without volume limit (at a low per-PC fee), but Microsoft retained the copyright, and Microsoft kept the right to license the same OS to any other PC maker.
IBM's lawyers did not object. Inside IBM, software was considered an accessory to the hardware; the moat for the PC business was assumed to be the IBM brand, the IBM sales force, and IBM service. Then, in 1982, Compaq lawfully reverse-engineered an IBM-compatible PC, and every clone maker that followed — Dell, HP, Gateway, Acer, Lenovo — shipped MS-DOS on every machine. The single clause IBM did not bother to fight gave Microsoft the first true platform monopoly in the software industry.
The lesson is not "the genius saw the future." Gates himself admits in Source Code (2025) that he did not foresee the scale of the clone market. His real motive for keeping the copyright was simpler: from the first day he dropped out of Harvard, he believed software was a product worth paying for. In 1976 he wrote the famous "An Open Letter to Hobbyists" to the Homebrew Computer Club, scolding amateurs for pirating his Altari BASIC. He was not arguing law. He was educating the market, again and again, that software has value. That conviction is what made him push for one extra clause in a room in 1980.
Sources: James Wallace & Jim Erickson, Hard Drive: Bill Gates and the Making of the Microsoft Empire (1992), Ch. 9; Stephen Manes & Paul Andrews, Gates (1993), Ch. 15; Paul Allen, Idea Man (2011), Ch. 8; Bill Gates, Source Code (2025); Walter Isaacson, The Innovators (2014), Ch. 9.On May 18, 1998, the U.S. Department of Justice and 20 state attorneys general sued Microsoft under the Sherman Antitrust Act. The core charge: using the Windows operating-system monopoly to bundle Internet Explorer and strangle Netscape Navigator. The presiding judge was Thomas Penfield Jackson; Microsoft's opposing counsel was David Boies — the same lawyer who, three years later, would represent Al Gore in Bush v. Gore.
On August 27, 1998, Gates sat for a twenty-hour videotaped deposition at Microsoft's Redmond headquarters. Ken Auletta, in World War 3.0 (2001), records it in detail: Gates rocked back and forth in his chair (a habit from childhood) and parsed nearly every question down to the verb — "What do you mean by 'concerned'?" "It depends on what you mean by 'compete'." When Boies produced an email Gates himself had sent saying flatly, "We are going to cut off Netscape's air supply," Gates replied, "I don't recall writing that." Auletta writes: "Everyone in the room watched him pretend not to recognize his own signature on an email he had written three years earlier."
On November 5, 1999, Judge Jackson issued his Findings of Fact, declaring Microsoft a monopolist that had abused its monopoly. On June 7, 2000, Jackson ordered the company broken into two — an OS company and an applications company. Microsoft stock fell 14% that day. On June 28, 2001, the appeals court overturned the breakup order (while upholding the monopoly finding), partly because Jackson, during the trial, had given off-the-record interviews to reporters with critical remarks about Gates that compromised his objectivity. In November 2001 Microsoft settled: no breakup, but the company had to open Windows APIs and allow PC manufacturers to preinstall non-Microsoft software.
The real turning point was not legal. It was personal. On January 13, 2000 — before Jackson even ordered the breakup — Gates resigned as CEO. His college roommate Steve Ballmer took over, and Gates moved into the role of "Chief Software Architect." He left day-to-day operations entirely in 2008. In Source Code he concedes that the deposition tape, replayed on every nightly news, turned him in the public mind from "American genius" to "arrogant monopolist" — a label that has weighed on every one of the twenty-five years of philanthropic work since.
Sources: Ken Auletta, World War 3.0: Microsoft and Its Enemies (2001); United States v. Microsoft Corporation, 253 F.3d 34 (D.C. Cir. 2001); DOJ Findings of Fact, November 5, 1999; Bill Gates, Source Code (2025), afterword.Beginning in 1995, twice a year, Gates retreated alone for a week to a family cabin on Hood Canal — no visitors, no family, no phone, just one caretaker bringing meals on schedule (his classic order: tomato soup and Diet Orange Crush). He brought 100 to 150 internal Microsoft white papers and outside research articles, paced himself at 15–20 minutes per paper, and wrote longhand annotations in the margins. This is the famous "Think Week." One Think Week in 1995 produced the memo The Internet Tidal Wave, in which he forcibly rotated Microsoft's strategic center to the Internet inside twenty-four hours. Robert Guth's 2005 Wall Street Journal feature reported that a single Think Week typically generated more than 100 new product decisions.
Reading is his longer-running habit. Since childhood, roughly 50 books a year (his mother Mary used pocket money to reward him for reading as a boy). Each year he publishes a "Summer Reading List" and a "Year-End Reading List" — not for PR; he writes his own reviews on the GatesNotes blog. He gravitates to biography, science, and public-health works. His method, he says, is to "finish the book, wait 24 hours, then take notes, forcing myself to recall the points" — a discipline from his Harvard days.
But the young Gates was extraordinarily hard to be around. Wallace's Hard Drive records the meeting-room culture of early-1980s Microsoft: he would shout at subordinates, "That's the stupidest fucking thing I've ever heard." He liked to nitpick and would argue until his opponent gave up. Former Microsoft executive Brad Silverberg said in an interview, "You had to be able to defend yourself in front of Bill for thirty minutes, or your project was dead." Paul Allen, in Idea Man, devotes pages to the 1982 fight that nearly ended their partnership — Allen was in chemotherapy for Hodgkin's lymphoma when he overheard Gates and Ballmer in the next room discussing how to dilute his equity. Allen wrote: "That was the moment I decided to leave Microsoft."
One less-noted habit: Gates is among the few mega-billionaires who does not play golf, collect supercars, or throw private-jet parties. His one indulgence is "Xanadu 2.0," his Hood Canal estate — but inside it sits a library, a lap pool, and LCD frames you can program with any painting in the world. He has said, "If at seventy you look back at your life, you'll find what you're proudest of is connected to what you thought about, not what you owned." There is a Munger-Buffett cadence to that line, and it is not accidental.
Sources: Robert Guth, "In Secret Hideaway, Bill Gates Ponders Microsoft's Future" — Wall Street Journal, March 28, 2005; James Wallace, Hard Drive, Ch. 16; Paul Allen, Idea Man, Ch. 10; Bill Gates, Source Code (2025).Four shadows that journalists have excavated repeatedly and that any honest reading must hold — each one quieter than Musk's headline-grade controversies, and each one heavier.
First, the Jeffrey Epstein meetings (2011–2014). Epstein had been convicted in 2008 of sex with a minor, but Gates met him at least six times between 2011 and 2014, including overnights at Epstein's Manhattan townhouse on East 71st Street. Gates's public explanation was "to discuss philanthropy" — Epstein was claiming he could help convene a Nobel-style global health prize. A May 2023 Wall Street Journal investigation revealed that Epstein knew of Gates's extramarital contact with a Russian bridge player named Mila Antonova and used it as leverage. In a March 2022 CBS interview, Melinda said plainly, "I did not like that he had meetings with Jeffrey Epstein. I made it clear how I felt and I think that's pretty much all I need to say about that."
Second, the 2021 divorce from Melinda. They met in 1987 at Microsoft (Melinda was an employee), married in 1994, and announced their divorce on May 3, 2021. In a later Fortune interview, Melinda said the 2019 Epstein revelations were "one of the reasons I ultimately decided." She remained co-chair of the Gates Foundation until her formal departure in 2024, taking $12.5 billion to capitalize her own Pivotal Ventures. It is among the most high-profile "power couple" divorces in three decades of American life.
Third, Microsoft workplace allegations. In 2019 the New York Times and Wall Street Journal simultaneously reported that the Microsoft board had, in 2020, investigated Gates's "intimate relationship" with a female employee that began in the early 2000s. Before the investigation concluded, Gates voluntarily resigned from the Microsoft board in March 2020. His spokesperson denied any impropriety, calling it "a consensual relationship that ended twenty years ago." The complication is that the official reason for his 2020 resignation — "to focus on philanthropy" — was, at minimum, only partly true.
Fourth, the "unaccountable power" critique of the Gates Foundation. The foundation is the largest private philanthropy in the world (about $75 billion in net assets; in 2024 it committed to spending $200 billion and winding down by 2045). Its influence over global public health and education exceeds that of many states. Critics — Anand Giridharadas in Winners Take All (2018), Tim Schwab in The Bill Gates Problem (2023) — make a single sharp argument: by what right does an unelected private individual, accountable to no one, decide which African diseases are prioritized or which American schools adopt Common Core? Schwab documents that Gates Foundation grants to mainstream outlets, including NPR, the Guardian, and PBS, have correlated with quieter critical coverage. Vandana Shiva and others argue that the foundation's high-yield seed programs in India have hurt smallholder farmers.
Hold those four together. What Gates faces at 70 is not a technology problem; it is the ethical question of whether one person has the right to remake the world alone. His donations have saved at least ten million lives, mostly through malaria, measles, and polio vaccines (WHO estimate). That is a fact. He alone decided where that money went. That is also a fact. The discipline of reading Gates is to never equate "philanthropy" with "morality" — philanthropy is an act; morality is a process.
Sources: Emily Glazer & Khadeeja Safdar, "Bill Gates Met With Jeffrey Epstein Many Times" — WSJ, May 21, 2023; Melinda Gates, interview with Gayle King, CBS Mornings, March 3, 2022; Emily Flitter & Matthew Goldstein, "Long Before Divorce, Bill Gates Had Reputation for Questionable Behavior" — NYT, May 16, 2021; Tim Schwab, The Bill Gates Problem (2023); Anand Giridharadas, Winners Take All (2018).It is August 27, 1998. You sit in front of a video camera; across from you is one of the strongest antitrust litigators in American history. You know every sentence over the next twenty hours will be replayed on national television, and you know every sharp email you wrote in your twenties will be produced one envelope at a time. You have three options. (A) Cooperate. Admit plainly, "Yes, we were trying to bury Netscape — that is competition." (B) Parse. Take every verb apart for thirty minutes. (C) Refuse to appear, let your CEO take the punishment. Gates chose B and paid 25 years of public-image cost. The deeper question: when "winning the case" and "winning the public" cannot both be won, which do you choose? Gates has spent the last 25 years using philanthropy to atone for the verbs he picked apart that day. Is there a moment in your own life where you won a fight and lost a generation of trust?
Bill Gates is the rare founder whose second act may eventually outweigh his first. The first act — Microsoft from 1975 to 2000 — built the software industry as we know it, secured on a single clause in the 1980 IBM contract that preserved Microsoft's right to license MS-DOS to any clone maker. The second act — the Gates Foundation since 2000 — has funded the rollback of malaria, polio, and measles across the Global South, saving by WHO estimates over ten million lives.
But neither act is clean. The 1998 DOJ deposition exposed a man who would parse "compete" for thirty minutes rather than admit a competitive intent everyone already knew. The Epstein meetings, the workplace investigation that preceded his 2020 board exit, the divorce, and the rising critique of unaccountable mega-philanthropy form a sober ledger. Gates remains the cleanest case study of a founder who outlived his founding mythology and was forced to reinvent himself, twice. Take the discipline of Think Week. Take the reading list. But also take the harder lesson — winning is not the same as being right.