Plan B Billionaires: The Founders Who Accidentally Built Empires While Failing at Something Else

There's a version of the startup story that gets told over and over: the visionary founder, the garage, the eureka moment, the straight line from idea to IPO. It's a great story. It's also, more often than not, complete fiction.

The messier truth is that a remarkable number of America's most consequential companies were built by people who were trying to do something else entirely — and failed at it, sometimes spectacularly, before stumbling into the thing that actually worked. What follows is a tour through some of the most improbable pivots in American business history.

Stewart Butterfield: The Man Who Failed at Games, Twice, and Won Anyway

Stewart Butterfield wanted to make video games. That's where the story starts. In 2002, he and a small team built a massively multiplayer online game called Game Neverending. It flopped. But while building it, they'd developed a photo-sharing tool on the side — almost as an afterthought. That tool became Flickr, which Yahoo acquired in 2005 for a reported $22–25 million.

You'd think that would be enough. It wasn't.

Butterfield tried again. In 2009, he launched another gaming company, Glitch. It was ambitious, beautifully designed, and deeply weird. It also failed. In 2012, with the company on life support, Butterfield and his team looked at the internal communication tool they'd built to keep themselves coordinated during development. It was, they realized, genuinely useful. More useful than the game.

They shut down Glitch and rebuilt the tool. They called it Slack.

Slack went public in 2019. Salesforce acquired it in 2021 for $27.7 billion. Butterfield failed at games twice. He accidentally built two of the most important communication platforms of his era.

Howard Schultz: The Man Who Went to Italy and Came Back Changed

When Howard Schultz first encountered Starbucks in 1981, it was a small Seattle retailer selling coffee beans and equipment — not beverages. Schultz was a housewares salesman at the time, curious about why this obscure little store was ordering so many of his drip coffee machines.

He joined the company. Then, on a buying trip to Milan in 1983, he walked into an Italian espresso bar and had what he later described as an almost religious experience. He came back convinced that America needed this — the ritual, the community, the standing-at-the-counter-with-strangers energy of the Italian café.

The Starbucks founders disagreed. They weren't interested in the beverage business. Schultz left, tried to raise money for his own coffee bar concept, got rejected by more than 200 investors, and finally scraped together enough to open a place called Il Giornale.

It worked. In 1987, he bought Starbucks from its original founders for $3.8 million. The rest is in every strip mall in America.

He wasn't trying to build a global chain. He was trying to recreate a feeling he'd had in Milan. The empire was incidental.

Walt Disney: Fired, Broke, and About to Change Everything

Before Mickey Mouse, before Disneyland, before any of it, Walt Disney was a failed commercial artist who couldn't keep a job. He was let go from the Kansas City Star in 1919 — the editor reportedly told him he lacked imagination. (Let that one sit for a moment.)

He started a series of animation ventures that collapsed. His first studio went bankrupt. He moved to Hollywood with forty dollars and a cardboard suitcase. He got swindled out of his first successful character — Oswald the Lucky Rabbit — by a distributor who owned the rights.

Out of that loss came desperation, and out of desperation came a mouse.

Disney later said that losing Oswald was one of the best things that ever happened to him. He had to create something he owned completely, something nobody could take. What he created instead became the foundation of a company now worth over $200 billion.

Failed artist. Fired employee. Fraud victim. Accidental legend.

Wrigley's Gum: A Freebie That Took Over

William Wrigley Jr. arrived in Chicago in 1891 selling soap. To move product, he threw in free baking powder with every purchase. The baking powder turned out to be more popular than the soap, so he switched — now he was a baking powder salesman. To move that product, he threw in free chewing gum.

You can see where this is going.

The gum was more popular than the baking powder. Wrigley pivoted again, this time for good. By the time he died in 1932, the Wrigley Company was one of the largest confectionery businesses in the world, and Wrigley Field — which he'd purchased and renamed — had become one of the most beloved ballparks in America.

He never set out to sell gum. He was trying to sell soap.

Instagram: A Check-In App That Couldn't Check In

Kevin Systrom and Mike Krieger spent months building Burbn, a location-based check-in app meant to compete with Foursquare. It was complicated, clunky, and going nowhere fast. Users weren't engaging with the check-in features.

But they were using one small piece of it — a photo-sharing function that had been almost an afterthought.

Systrom and Krieger stripped everything else away. They rebuilt around the photos, added filters, and launched in October 2010. Within 24 hours, 25,000 people had signed up. Within 18 months, Facebook acquired Instagram for approximately $1 billion.

The app nobody wanted spawned the app that changed visual culture. All they had to do was throw away everything they'd originally built.

The Pattern Hiding in Plain Sight

Look at these stories long enough and something becomes clear: the pivot isn't the failure. The pivot is the strategy, even when nobody planned it that way.

Each of these founders shared a few things. They were paying attention — not just to what they'd built, but to what people were actually using and why. They were willing to abandon sunk costs, to let go of the thing they'd been working on when something more promising appeared. And critically, they'd already been through enough failure that they'd lost their fear of it.

That last part might be the most important. The person who's never failed at anything is often the most paralyzed by the possibility. The person who's already failed — who's already survived the embarrassment and the empty bank account and the investors who didn't call back — has a different relationship with risk. They know what the bottom feels like. They know they can climb back up.

Plan A, in most of these cases, wasn't a mistake. It was tuition.

The empire was always going to be Plan B.