When you think of Bill Gates, you think of Microsoft, Windows, and a guy who basically rewrote the rules of modern technology. But behind every mega-success is a pile of not-so-mega-successes. That’s just how the game works—even for one of the richest, smartest, and most influential people in the world.
You see, Gates didn’t just wake up one day, wave a magic wand, and create a tech empire. Along the way, he dabbled in plenty of ideas that didn’t stick, startups that flopped, and products that made people scratch their heads. But here’s the thing: failure didn’t stop him. In fact, it’s probably part of what made him so great.
10 Times Bill Gates Took a Big Swing (and Missed): Why Even Geniuses Have “Oops” Moments
So, let’s dive into 10 startup ideas or projects by Bill Gates that didn’t exactly make it to the hall of fame—and the lessons they teach us about dreaming big and bouncing back.
1. Microsoft Bob: Your Clingy Computer Friend
Back in 1995, Gates and his team thought computers needed to feel more “human.” Enter Microsoft Bob, a quirky, cartoonish interface that turned your desktop into a cheerful little house. Instead of icons, you’d click on things like a virtual desk or lamp. Cute idea, right? Nope. Users found it clunky, childish, and downright annoying. Poor Bob didn’t even last a year.
Lesson: Sometimes, people just want their tech to do its job—not to feel like they’re stuck in a Saturday morning cartoon.
2. Microsoft Encarta: When Wikipedia Wasn’t a Thing Yet
Before the internet became our one-stop shop for answers, Encarta was the real deal. A digital encyclopedia on CD-ROM, it brought knowledge right to your computer. For a while, it was great—until Wikipedia showed up, offering the same thing for free and constantly updated. Encarta couldn’t keep up and was shut down in 2009.
Lesson: If your business model can’t compete with “free,” it’s time to rethink the game plan.
3. WebTV: Surfing the Internet on Your TV, the Slow Way
In the late ‘90s, Microsoft dreamed of combining the internet and TV with WebTV. The idea was solid—browse the web from the comfort of your couch. But back then, internet speeds were painfully slow, and the interface left a lot to be desired. Fast forward to today, and smart TVs and streaming devices like Roku and Firestick are thriving. WebTV? Not so much.
Lesson: A good idea launched too early is like planting seeds in winter—it won’t grow. Timing is everything.
4. Bing: The Underdog That Couldn’t Topple Google
When Microsoft introduced Bing in 2009, it was their big move to challenge Google’s search engine dominance. They poured billions into it, even adding flashy features like image search and rewards for users. But Google had already become the search engine, and Bing never managed to shake its “always second best” reputation. While it still exists, it’s hardly a Google-killer.
Lesson: It’s tough to unseat a king once they’re on the throne—even if you’re throwing money at the problem.
5. Tablet PC: A Brilliant Idea That Needed More Time
Picture this: It’s the early 2000s, and Microsoft unveils the Tablet PC, a sleek (for the time) touchscreen device that could replace your laptop. Sounds amazing, right? Except it was expensive, bulky, and not very user-friendly. People shrugged, and the product faded into obscurity. Then, years later, Apple dropped the iPad, and suddenly, the whole world wanted a tablet.
Lesson: Being first doesn’t mean you’ll be the best. Execution matters as much as innovation.
6. Microsoft Zune: The iPod Wannabe
Microsoft thought they could dethrone Apple’s iPod with the Zune, their own version of a portable music player. While Zune had some neat features, it didn’t have the sleek design, user-friendly interface, or cool factor of the iPod. Apple was already miles ahead, and the Zune just couldn’t catch up. By 2012, it was discontinued.
Lesson: If you’re joining a crowded market, you need to bring something that blows the competition out of the water. “Pretty good” won’t cut it.
7. Windows Mobile: The Smartphone That Didn’t Get the Memo
Microsoft’s attempt to break into the smartphone world with Windows Mobile and Windows Phone was… well, awkward. Android and iOS were already dominating the market, and Microsoft couldn’t convince developers to build apps for their platform. Without apps, users weren’t interested. By 2017, they threw in the towel.
Lesson: If you’re not giving people what they really need, they’ll go somewhere else—fast.
8. Microsoft Groove: A Collaboration Tool That Didn’t Groove
Groove was meant to be a cool, peer-to-peer file-sharing and collaboration tool. It sounded promising, but it never found its audience. Microsoft eventually folded its features into OneDrive and SharePoint, and Groove itself was retired in 2017.
Lesson: Sometimes, it’s okay to admit your idea works better as part of something bigger.
9. MSN Messenger: The Cool Kid That Got Left Behind
Ah, MSN Messenger. If you were online in the early 2000s, you probably used it to chat with friends and crushes. But as platforms like WhatsApp, Snapchat, and Facebook Messenger rolled in with better features and mobile-first designs, MSN Messenger couldn’t keep up. By 2013, it was gone for good.
Lesson: Staying relevant means staying adaptable—and not getting too comfortable.
10. HoloLens (for Consumers): A Future Too Far Off
The HoloLens is Microsoft’s augmented reality headset, and it’s seriously cool. But with a price tag in the thousands and limited consumer-friendly applications, regular folks just weren’t buying it. Microsoft has since pivoted to marketing HoloLens to businesses, where it’s finding its stride.
Lesson: Not every product needs to be for everyone. Sometimes, focusing on a niche audience is the better move.
Failing Forward: Why Bill Gates is Still Winning
So, what’s the moral of the story? Even the smartest people in the world don’t always hit the bullseye. Gates’ “oops” moments didn’t stop him from becoming one of the greatest innovators of all time—they taught him valuable lessons that he applied to future successes.
If there’s one thing we can learn from Bill Gates, it’s this: Don’t be afraid to take big swings. Sure, you might miss, but every failure brings you closer to the home run. Or, as Gates himself might put it, “It’s fine to celebrate success, but it is more important to heed the lessons of failure.”
