The History of Windows: The 15 Best (and Funniest) Stories by Bill Gates

Brad Jones 05-12-2017

Here are 15 true stories and quotes about Bill Gates and the rise of Microsoft Windows.


Bill Gates became internationally recognized over the 1980s and 1990s thanks to his part in making personal computers a hugely important component of modern life. His exploits have been collected in books, movies, and countless interviews.

Here are some of the most illuminating looks at a major figure in the history of computing The History of the Windows Start Menu For all the pomp and ceremony surrounding the release of Windows 10, one of the most well-received features of the operating system is the return of an old friend—the Start Menu. Read More . Gates has clearly changed a lot over the last thirty years, and some of these stories show just how different today’s philanthropist is from yesterday’s ruthless businessman.

1. Bill Is Pretty Frugal for a Billionaire

Windows made Bill Gates the wealthiest man in the world, but you wouldn’t know it if you saw how he spends his money 10 More Spreadsheet Templates to Manage Your Money Templates can make challenging tasks easier. Managing your money is one of them. Use these spreadsheet templates to get started and customize them to your needs. Read More .

Responding to a Quora thread in 2014, Brad Silverberg (who was SVP at Microsoft throughout the 1990s) recalled an interaction with Gates just after the launch of Windows 3.0. The company was riding high at the time, but its head honcho wasn’t exactly living the jet-set lifestyle:

“Company policy was that everyone flew coach. And there was Bill, sitting in coach, in a middle seat. It didn’t matter to him; he spent the whole flight reading. He wasn’t as universally recognized then so it wasn’t such an issue for him to fly commercial.”

While Gates pours much of his money into philanthropic efforts, he has upped his game when it comes to air travel. A personal plane is one of his personal luxuries, these days.


2. Bill Once Claimed Windows Was Basically Bug-Free

If you’re a Windows 10 user, you might have spotted a few bugs Microsoft Will Pay You to Find Bugs in Windows 10 Microsoft has launched a new bounty program aimed at encouraging Windows users to find bugs in its products. And doing so could bag you up to $250,000. Read More or other issues with the operating system. However, back in 1995, Gates claimed that Windows had such a minimal amount of bugs that customers wouldn’t purchase new software if fixes were all that was being offered up.

In an interview with Focus Magazine, Bill Gates said:

“There are no significant bugs in our released software that any significant number of users want fixed. I’m saying we don’t do a new version to fix bugs. We don’t. Not enough people would buy it.”

3. Bill Could Be Rather Foul-Mouthed

Joel Spolsky is the CEO of Stack Overflow, but in the early 1990s he worked as a program manager on the Microsoft Excel team. It was during this time that he had to report on the group’s progress to Gates himself.

In a blog post published in 2006, Spolsky wrote:


“In my BillG review meeting, the whole reporting hierarchy was there, along with their cousins, sisters, and aunts, and a person who came along from my team whose whole job during the meeting was to keep an accurate count of how many times Bill said the F-word. The lower the f*** count, the better.”

He did pretty well, only racking up four curse words. “Bill is getting mellow in his old age,” observed his colleague who had been assigned the job of counting the swears.

4. Bill Would Remain in His Office for Days on End

Developing an operating system like Windows is not easy. Gates was forced to stay in his office for days while working on particularly challenging or time-consuming tasks. He now blames this kind of behavior on his youthful energy and naivety.

When asked about his workaholic past on Reddit, Bill Gates reflected:

“Now hopefully I am a bit more mellow but with a little extra wisdom.”

5. Bill Was a Difficult Man to Reach

The workaholic side of Gates’s personality Are You a Workaholic? Reclaim Your Work-Life Balance Read More was certainly a key part of Microsoft’s success. On the other hand, his tendency to avoid direct contact was something of a frustration for others trying to work with the company.


A 1981 edition of InfoWorld Magazine states that Gates was already “notorious” for not answering the phone, and not returning calls. Once Windows hit its stride, good luck getting any face time with the CEO.

6. Bill’s First Windows Pitch Was a Cold Call to IBM and DEC

Thanks to Windows, it makes complete sense that separate companies would develop computer hardware and the operating system that runs on it. However, this wasn’t the case thirty years ago, and convincing the major players in the industry wasn’t easy, especially as a teenager.

“The companies that built the computers — IBM and DEC — they did all the software,” Gates remembered in a speech to the Economic Club of Detroit delivered in 1997. And when we called them up and said, “We would like to do an operating system,” they said, “Who are you?” to which we said, “We’re high-school students.” That was, uh — that was the end of that conversation.

7. Bill’s Backup Plan Was Artificial Intelligence

Most would agree that Gates has had a pretty successful career. However, if Microsoft hadn’t have panned out, he would probably have ended up working in artificial intelligence 5 Best Google AI Experiments to Explore Artificial Intelligence Google has several AI experiments that you can go and play with, right now. Thanks to machine learning, they can change tomorrow's world with your help. Read More .


When asked about other paths he might have taken in a Reddit AMA in 2015, Gates replied:

“I would probably be a researcher on AI. When I started Microsoft I was worried I would miss the chance to do basic work in that field.”

8. Bill Is a Fan of Pirates of Silicon Valley

Pirates of Silicon Valley is a 1999 movie based on the book Fire in the Valley: The Making of the Personal Computer. It focuses on the relationship between Bill Gates, Steve Jobs, and some of the other major players in the early days of personal computing.

Director Martyn Burke opted not to interview the subjects of the movie, hoping this would add to its realism. Still, it seems that Gates thinks that he did a fairly good job of capturing the dynamic. “That portrayal was reasonably accurate,” he said when asked about the film in a Reddit AMA in 2013.

9. Bill Admits That Windows Had a Shaky Start

The rivalry between OS/2 and Windows had a huge impact on the development of personal computers as a whole. Looking back on it now, Gates describes it as the “battle of the weaklings.”

“Until 1990 neither product sold at all,” he said in an interview with the National Museum of American History. “And in 1990, Windows took off.”

10. Bill Regrets Not Releasing WinFS

Over the years, there have been various different components of Windows that never made it to market. WinFS, a potentially revolutionary upgrade to the operating system that would have allowed files to be augmented with nuggets of information to allow for easy searching and categorization, is Gates’s white whale.

“We had a rich database as the client/cloud store that was part of a Windows release that was before its time,” Gates wrote in a Reddit AMA in 2013. At that time, he predicted that the concept would re-emerge in the future.

11. Bill Wasn’t Too Worried About Piracy Back in the Day

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In 1998 he told CNET:

“About 3 million computers get sold every year in China, but people don’t pay for the software. Someday they will, though. As long as they are going to steal it, we want them to steal ours. They’ll get sort of addicted, and then we’ll somehow figure out how to collect some time in the next decade.”

12. Bill Was Fiercely Competitive

By all accounts, Gates has softened in recent years, especially since becoming a father. However, there is no shortage of stories about his competitive nature during his younger days.

Fred Thorlin was the director of the Atari Program Exchange between 1982 and 1984. Being in the computing industry at this time, he and Gates crossed paths. Speaking in 2000, he claimed that they were on first-name terms in an interview that can be read on the Atari Archives:

“I showed him a simple game which you could play in well under a minute. I beat him about 35 out of 37 efforts. I came back a month later, he won or tied every game. He had studied the game until he solved it. That is a competitor.”

13. Bill Liked to Drive Fast

When Windows was on the rise, Gates became well known to traffic cops who would patrol the area around Microsoft headquarters. In fact, he had to hire the best traffic attorney in Washington State to ensure that he didn’t end up in serious trouble, according to a report from Business Insider.

One day, Gates borrowed a friend’s Porsche 928 and took it for a spin. Let’s just say the drive didn’t end well — the repairs apparently took almost a year.

14. Bill Thinks Control-Alt-Delete Was a Mistake

Before Windows 10, Ctrl-Alt-Del was the button combination Windows Keyboard Shortcuts 101: The Ultimate Guide Keyboard shortcuts can save you hours of time. Master the universal Windows keyboard shortcuts, keyboard tricks for specific programs, and a few other tips to speed up your work. Read More Windows users would have to input every time they wanted to log into their system.

Gates has since admitted that there could have been a more elegant solution.

“It was a mistake,” Gates said during a Harvard fundraising event, transcribed by The Verge. “We could have had a single button, but the guy who did the IBM keyboard design didn’t wanna give us our single button.”

15. Bill Was Pretty Good at Minesweeper

Everyone remembers the games that have been bundled with Windows over the years, from the downhill action of SkiFree to the perplexing puzzles of Chip’s Challenge. Gates had a particular affection for Minesweeper.

“I forget the exact time but I think I had a time below 10 when it was just right,” he said when asked about his high score in a Reddit AMA held in 2016. He cited a lucky configuration as the reason behind his success.

Do you have more stories or quotes about Bill Gates and Windows? Why not share them with other readers in the comments section below?

Related topics: History, Microsoft, Nostalgia.

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  1. Eric Straub
    December 6, 2017 at 7:32 pm

    I believe the article should say 1977 (not 1997) for #6.

  2. "Barry James" Folsom
    December 6, 2017 at 6:58 pm

    Just to set the record straight, DEC absolutely partnered with Bill Gates and Microsoft to bring Windows to market on the DEC Rainbow. I had the honor of representing DEC, along with 23 other companies, at the announcement of Windows that took place at Windows_on_the_World a top of the North Tower of the World Trade Center, NYC, in November, 1983.