How 7 Successful People Bounced Back From Failure

James Dyson failed 5,126 times before he found a version of his Dual Cyclone vacuum cleaner that worked. To many, this would make him a loser, yet today he is worth $4.2 billion.

After interviewing 200-plus people, I’ve realized the most successful individuals I know were, at some stage along their journey, a big loser. They failed. They made giant mistakes. They lost a lot of money, and watched as their business went under. Yet, they managed to overcome such adversity and build success on the back of these business-threatening mistakes.

arianna huffington
Arianna Huffington.Richard Drew/AP

Which begs the question, how do they do it?

Mistakes happen; this you cannot avoid. The journey you’re on isn’t a simple one, and at some point you may hit rock bottom. This is okay, as you can rise from the ashes like these seven losers did.View As: One PageSlides

1. Scott Oldford

1. Scott Oldford


Founder of Infinitus, Leadcraft and Bots for Business

In 2013, Oldford racked up $726,000 in debt. At the ripe age of 22, he faced a bleak future. It’s a mountain of debt many people wouldn’t escape from.

Yet, in less than three years, Oldford not only recovered, but built a multi-million-dollar company by overcoming his own toxic ego, and replacing it with a deep focus on relationships, mentorship and personal growth.

From big loser to bigger success, Oldford today demonstrates a zest for life that has led to successful launches, new ventures and an ever-growing level of authority.

Related: He’s Human After All: 5 Times Elon Musk Completely Failed

2. Caprice Bourret

2. Caprice Bourret

Loose Women/Youtube

Founder of By Caprice

With millions of dollars of product en route, Caprice Bourret celebrated her new partnership with a South African department store. With By Caprice Lingerie still in its infancy, this was a big deal with even bigger potential.

Then the phone rang, leaving Bourret’s world turned upside-down, as she learned the buyer only wanted half of what she had sent — and because the stock was in South African sizes, she couldn’t sell it elsewhere.

A successful and celebrated supermodel, but a now failed entrepreneur with a business on the brink. Yet, Bourret not only bounced back from the setbacks, but redefined her business model by leveraging her strengths (a strong personal brand) to license her name to foreign parties. Not only did this lower costs, but created an abundance of opportunities that redefined her business.

3. Jayson Gaignard

3. Jayson Gaignard


Founder of Mastermind Talks

Despite building a multi-million-dollar business, Jayson Gaignard found himself in over $250,000 of debt. Gaignard suddenly had the bank threaten to take his house, car and possessions. He had failed. He had let his family down. He had no Plan B.

Yet, he held firm to his belief that relationships are everything, and so he continued to splash out on unique dinners for high-worth individuals, plunging further into debt, but strengthening his connections as he did. Before long, these dinners transformed into one of the planet’s most sought-after conferences, featuring the likes of Tim Ferriss, Ryan Holiday and AJ Jacobs. 

4. Ari Meisel

4. Ari Meisel

Biohacker Summit/Youtube

Founder of Get Leverage

After years of hustling, Ari Meisel developed Crohn’s disease, a chronic, usually incurable illness, in 2007. Yet, within a matter of months, Meisel did the impossible and beat the disease, regaining control of his life after years of abusing it.

Although his business wasn’t the sole cause of his disease, his fast-paced lifestyle did play a fundamental role. He damaged his health and wellbeing to the point of no return, but it’s also this period that helped him realize what he wanted from life.

This led to his latest company, where Meisel and his team work with busy entrepreneurs to ensure they don’t suffer the same (near irreversible) fate he did.

5. Arianna Huffington

5. Arianna Huffington

Flickr/C2 Montréal

Founder of The Huffington Post and Thrive Global

Back in 2007, Arianna Huffington sat at home on the phone, when all of a sudden she collapsed. When she woke up, she lay in a pool of her own blood, and had what she would later discover, a broken cheekbone.

It wasn’t cancer. It wasn’t a disease. Huffington was, of course, exhausted. However, she later described this terrifying period as the “wake up call that changed my life.”

Not only did this lead her to create Thrive Global, but also author bestselling books like Thrive and The Sleep Revolution. Though Huffington had already achieved great acclaim with her eponymous news site, it was this setback that pushed her to follow her passion and also achieve success in her personal life. 

6. Mike McDermott

6. Mike McDermott


Founder of Freshbooks

When Mike McDermott and the Freshbooks team invested $1.5 million in a new piece of software, they hoped it would take their ever-growing cloud accountancy company to the next level.

It did not. They faced problem after problem, eventually scrapping the project and building their own version of the software instead.

This expensive failure that threatened the business, but because McDermott was no stranger to adversity, he was able to to turn this mistake into opportunity. Today, Freshbooks has helped more than 10 million small businesses keep their finances in check, passing on valuable lessons so their customers don’t make the same mistakes they did.

7. Noah Kagan

7. Noah Kagan

Silicon Prairie News/Flickr

Founder of Sumo

Noah Kagan was employee No. 30 at Facebook, which, had he stayed, would have made him over $100 million. However, Facebook fired him after eight months, which sent him into a spiral of depression.

Kagan overcome this (and the title of “the guy who got fired by Facebook and lost $100-plus million”), and has since built numerous successful businesses.

These seven business owners were once losers, yet far from it today.

None of this makes failure any easier, but you should take inspiration from the fact that those you admire once hit their own version of rock bottom. This ride you’re on isn’t easy, but you can make it easier by learning from those who have been there and done it.

These seven losers are all worth following in 2017 (and beyond), as they continue to push the boundaries and innovate. You can sit by and be a passenger, or dissect each mistake and failure you make, always asking yourself: What can I learn from this?

This is what the most successful entrepreneurs on the planet do, and you can, too.

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