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How These 6 Entrepreneurs Failed but Then Found Success


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Every entrepreneur setting out on the long trek towards accomplishment will face setbacks. It doesn’t matter how flawlessly they approach matters, how remarkable their talent is, or how hard they try to skirt the usual rigamarole — they’ll inevitably suffer myriad failures ranging from minor to major. It’s simply a part of life.

But there’s really nothing wrong with failure. In fact, it can turn you into someone great. As the great (albeit fictional) boxer Rocky Balboa famously said, life ain’t about how hard you hit — it’s about how hard you can get hit and keep moving forward. Every time you endure a blow that would knock someone else out, you set yourself apart.

Don’t take my word for it, though. Just look at the countless successful entrepreneurs out there who’ve failed to varying degrees before making it. To save you some time, I’ve picked out 6 that I’m familiar with, so let’s see what we can make of their stories:

James Dyson

Today, Dyson is a name synonymous with vacuum cleaners, but he didn’t rocket to fame in a heartbeat. He didn’t even lead off with a compelling product. In fact, he only really had an idea and an ambition — it took a long time, and 5,126 failed prototypes, for that ambition to be realized. And even then, he struggled. Getting nowhere in his homeland, he tried his luck in Japan, and only then did he find success.

With that foothold established, he was able to invest his profits from the Japanese market into expanding and developing his business back in England. Of course, we know now what happened: his bag-free technology caught fire with shoppers, selling in huge numbers both there and (soon enough) across the world. It even earned Dyson a knighthood.

In an interview with Fast Company magazine, Dyson had this to say on the matter: “I made 5,127 prototypes of my vacuum before I got it right. There were 5,126 failures. But I learned from each one. That’s how I came up with a solution. So I don’t mind failure. I’ve always thought that schoolchildren should be marked by the number of failures they’ve had. The child who tries strange things and experiences lots of failures to get there is probably more creative.

Now, does this mean that failure is a sure sign that you’re on the right track? No, of course not, just as the adage that encountering resistance means you should keep going (so popular in the social media age) doesn’t stand up to scrutiny. But it does mean two things: failing doesn’t mean you’re not right overall, and what’s important is to learn from failure so you do better later.

Jayson Gaignard

MastermindTalks is an exclusive summit for entrepreneurs. To attend, you need to be invited, and it now attracts some of the world’s leading successes (particularly when it comes to networking). The founder, Jayson Gaignard, knows and works with some very influential figures — but he had to work hard to make it.

Starting his entrepreneurial journey by providing a concierge service, Gaignard eventually hit trouble, finding himself in debt to the tune of $250k and having no clear path ahead of him. After being inspired by a talk he attended, though, he decided to go all-in on the professional connection game: serving as the link between high-value professionals, and helping rising entrepreneurs find suitable mentors.

He started setting up exclusive dinners for those willing to pay for entry, with the appeal being the opportunity to spend time with notable figures. Today, tickets to MastermindTalks events are selling swiftly and easily, and Gaignard has fully turned things around. He also hosts a podcast called Community Made, titled after the perspective he clearly embraces: “The speed in which I’ve turned my life around is thanks to one thing, and one thing only… My relationships. The rarely spoken about truth when it comes to success is that nobody does it alone.

One of the most tempting parts about becoming an entrepreneur is that it grants you absolute control over where your time goes. If you don’t want to do a particular piece of work or take on a given client, you can simply opt out of it. But this doesn’t mean working alone. What Gaignard knows (to his advantage) is that exerting your agency as part of a collective bound not by contracts but by community gives you the best of both worlds: the limitless direction of running a one-person operation, and the reach of being part of a team.

Larry Ellison

Computer technology company Oracle is one of the largest software developers in the world, only falling short of Microsoft and Alphabet (Google’s parent company), and founder Larry Ellison is one of the wealthiest people in the world. But Oracle hasn’t always been in such a lofty position. Just four years after going public, the company was on the brink of collapse: major layoffs were needed, with the sales team having exaggerated its revenues.

Larry Ellison

It took a lot of work and commitment to redeem the company. Ellison made huge changes to the managerial structure, recognizing that the existing team wasn’t up to the task, and charted a course through the inevitable lawsuits that followed the inflated revenue claims. Soon enough, the skies cleared up, and the company started moving in the right direction again.

The lesson from this? Of Ellison’s many business-related quotes, I’d say this is the most applicable: “All you can do is every day, try to solve a problem and make your company better. You can’t worry about it, you can’t panic when you look at the stock market’s decline. You get frozen like a deer in the headlights. All you can do is all you can do.

When Oracle was in deep trouble, he could have sold his piece of the company, found another job (or founded another company) and left it to rot. The problems didn’t arise from his personal failure, after all. But he didn’t. He maintained his focus on the development of the company, kept a cool head, and steadily worked through the issues. So when you encounter difficulties, consider things rationally — can you overcome them? If so, do it. There’s no need for panic.

Nick Woodman

Even if you’ve never used a GoPro, you’ve certainly heard of it. As YouTube entered adolescence, GoPro footage was a huge part of pushing the content ahead, and it’s difficult to say how different today’s digital video content would be had Nick Woodman never founded the company. But it didn’t have a typical origin, and nor did Woodman.

Graduating with a degree in visual arts, he didn’t have a background in business when he entered the entrepreneurial world, and it clearly showed. He launched one business, got nowhere, launched another business, achieved comparable results, and ventured off on a surfing tour to clear his head. While looking to record surfing footage, he hit upon the idea of the GoPro, and the rest is history.

Of course, it hasn’t all been smooth sailing (or smooth surfing) since then. The company hit some rocky times following its huge success, and an effort to move to using drones ultimately went nowhere and had to be scrapped. Only when the company went back to its roots and came out with a much-improved model did its fortunes turn around.

Woodman had this to say on the matter: “When we went public, we tried to make GoPro as broadly relevant and appealing as possible, and tried to reach everybody, arguably at the expense of our best customers,” he said. “Not everybody in the world needs a GoPro. We recognize that [now].” The right idea at the right time made GoPro a hit, but it took another failure (overlooking customer research) to set the company on the right long-term path.

The big takeaway from Woodman’s journey is that things are rarely as simple as failing enough times to reach a point of non-stop success. You can fail ten times, succeed ten times, then fail again. What he’s able to do is carry on and not let the failure discourage him. Learn something every time you fall, then get back up.

Tim Ferriss

Tim Ferriss is well-established in the business world, with his book The Four-Hour Workweek being commonly cited as one of the most influential works behind the modern-day push for flexible business operations — but the establishment took some time. Indeed, the manuscript for The Four-Hour Workweek was rejected 25 times before it was accepted.

Tim Ferris

When a publisher did accept it at last, it wasn’t because it had different taste from those that rejected it. It was because it believed in Ferriss: believed in his determination to make it a hit. And make it a hit he did. His ideas on automation and workflow efficiency became firmly entrenched in the business mainstream, and his own podcast is now one of the top-ranked in the business world.

He elaborates on his approach in his appearance on SEO guru Stephan Spencer’s Get Yourself Optimized podcast, saying “If you can take time-consuming tasks, unpleasant tasks, or simply boring tasks both in your professional and personal life, consider delegating them to someone else.” One rule that protects him from risk is outsourcing to services, not individuals: “I don’t like single points of failure so if someone gets sick or disgruntled or gets fired or quits, I don’t want to have a project fall through because of that.

What this means for anyone with startup ambitions is that keeping a tight grip on every aspect of an operation only creates a single point of failure. One person can make the same mistake over and over again, or get distracted, or lose interest in a project. By spreading the workload, you can minimize the damage of any point of failure: something minor going wrong isn’t the portent of anything else going wrong.

Evan Williams

The story of Evan Williams is one of success, failure, and even greater success. Back in 2003, when he was working for Google (after it acquired his company), he was named as one of the world’s top 100 innovators under 35. But just one year later, he decided to leave Google to co-found Odeo, a podcast company that came along at the worst possible time — not long before iTunes launched and immediately assumed dominance.

Odeo was clearly doomed, so Williams didn’t fight it: instead, he gathered members of the board to spend a day brainstorming alternative ideas. One of the ideas floated? The seed that would grow into Twitter. Williams served as co-founder, and later CEO. Though he stepped down as CEO in 2010, he remained involved in the company, and his stake in the growing business led to his personal wealth growing enormously.

What does Williams have to say about his failures? “Luck comes in many forms—and often looks bad at first. I always look back on the deals that we didn’t do and the things that didn’t work out, and realize what seemed like a bummer at the time was really lucky. …if you have some plan and it doesn’t go that way, roll with it. There’s no way to know if it’s good or bad until later, if ever.

Armed with no way of knowing for sure whether it was worth battling to save Odeo, he simply rolled with the concept that stemmed from that brainstorming session. As it happened, it was the right move, but Twitter might never have existed had he not been willing to try it without any guarantee that it would pay off.


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