If there’s one word to describe what it’s like being an entrepreneur, “trying” fits in almost all sense of the meaning. While you’re trying this and that to make your business a success, it may be trying on your patience–but most successful entrepreneurs know that it’s all this trying that eventually gets them somewhere! So next time you’re being hard on yourself for spending an extra $100 on something your business didn’t end up needing, you can remember these 5 wildly successful entrepreneurs who have “tried” and failed–a lot.

Elon Musk

The man, the myth, the legend–and the richest man in the world–isn’t immune to the difficult aspects of business ownership, in fact, he has been very open about his financial struggles with Tesla and SpaceX.

“To be frank, in the early days, I thought there was >90% chance that both SpaceX & Tesla would be worth $0. The press & aerospace / automotive industry at the time (correctly) agreed with me,” he Tweeted in 2020.

Nearly two decades later and Teslas can’t seem to fly off the shelves fast enough (I’m looking at you, car vending machines), especially in light of the recent gas price surges.

However, Musk continues to deal with the very real possibility of his businesses, particularly SpaceX, going bankrupt. After surviving nearly going under in 2013 with three failed launches and 100m spent in personal losses, SpaceX finally seemed to be on the up and up. But it was only in November of last year that he stated that there’s still a very real possibility that his space endeavors could dry up depending on the economy.

The lesson to learn here from Musk is that endeavoring to persevere is a key aspect to overcoming business hiccups–no matter how crazy it may seem to other people.

Bill Gates

Previous wealthiest man titleholder and visionary behind the programming of your computer (at very least, your parent’s old computer from the 1990s) Microsoft visionary Bill Gates has “failed” at numerous things–including college.

I’m sure you have seen the meme or perhaps heard someone say that Gates was a college dropout, and yes, he was. However, it usually fails to mention that he dropped out of Havard. By no means was Gates an uneducated man, but he decided the standard scholarly route wasn’t what interested him. What’s more, around that same time he closed his failing business that you probably never heard of, Traf-O-Data.

And that’s only scratching the tip of Gates’ “whoops” iceberg.

Though he had seemingly every opportunity to make it happen, he infamously let Google become the world’s leading search engine, and while we’re on the subject of rival companies, he helped bail the software competitor, Apple, out of bankruptcy in what was later dubbed one of the worst business deals ever.

He doesn’t let that bother him though, and I mean, why should he? He’s still one of the wealthiest humans alive today–and again, he’s human. He makes mistakes too.

Steve Jobs

On the topic of Apple and bankruptcy, let’s talk about how Steve Jobs was forced to resign from the company in 1985, less than a decade after he founded it and it wasn’t until about 12 years and many business endeavors later when he would be able to return.

The thought of being fired from their own company is perhaps enough to make any entrepreneur gag–but for Jobs, it “was the best thing that could have ever happened.”

He used the downtime to work on an array of other projects including becoming a chairman and executive producer of, you wouldn’t have guessed it, Pixar’s Toy Story.

And like a phoenix rising up from the ashes, he came back to Apple better than ever after his hiatus, leading it to become one of the world’s most valued companies.

Jeff Bezos 

When the world makes fun of you for creating a rocket that looks oddly similar to…something else… you leave the world–that’s Jeff Bezos’s motto, right?

Kidding (please don’t sue me, Jeff.)

Anyways, despite being the focal point of the internet’s countless memes, with a business strategy of “experiment and take risks,” Bezos is no stranger to overcoming hardships and taking responsibility for failings.

From the recent antitrust issues aimed at Amazon to his costly Amazon Fire Phone launch in 2014, and a host of many other company blips, the businessman has seen his share of nonsuccessful implications. Though, I must say, if there’s one secret to his success it has to be his ability to solve problems.