Ups and downs are a natural part of starting a business. Yet some entrepreneurs have endured such great lows that there really was no chance of falling any further. The fear of these bad times motivates some, but also stops others taking the risks often necessary to make a company a success.

So, what can we learn from those who have been there? Here are four highly successful people who hit the lowest of lows before making it big.

1. Chris Gardner

Back in 1987, Chris founded Garner Rich, which went on to become a highly successful brokerage firm with offices in Chicago, New York and San Francisco. It wasn’t this that made him famous, though. As he explains in detail in his bestselling memoir, The Pursuit of Happyness, before becoming a broker, Chris spent a year of his life living rough on the streets. It’s difficult to imagine how things could be worse but he had his toddler son with him too.

The book was later made into a film starring Will Smith, and anyone who has seen it will know that there was one true moment that changed the course of his life – the decision to approach stockbroker Bob Bridges to find out what he did to be so rich.  Even though, he ended up homeless after this, his perseverance to fight his way out of the situation really is the stuff of movies.

What does Chris’ story teach us?



Be resilient. No matter how great your idea or how well you start out, no one can avoid pitfalls forever. Most entrepreneurs credit their success to their failures because of what they learnt.

But this is always one of those pieces of advice that is easier to say than believe in the moment. When it’s your company or life that is spiralling out of control, it takes resilience to power through and come out successful on the other side. It’s a key trait for any budding entrepreneur.

 2. Moustafa Mahmoud

Moustafa Mahmoud is the founder of Cognitev, a company that uses artificial intelligence to power marketing and advertising. Before this he was involved in setting up ShopShopMe.com, the UAE’s first price comparison site.

Yet things haven’t always been this rosy. Moustafa’s first business, an online jewellery and fashion store called Xeswar, failed to keep pace with competitors. It went bust, leaving him with nothing. He didn’t give up, though, instead he began another company, ShuGeek, but this rapidly followed a similar fate.

He started to see that his problem wasn’t his product or price, but that customers weren’t finding him. That’s where ShopShopMe.com was born, the idea that gave him his first true success.

What does Moustafa’s story teach us?

Try, try and try again. Are we born entrepreneurs or are we crafted into them? Research from Stanford University certainly seems to back up the idea that it’s the latter.

The Stanford researchers looked at measures of success from 2.3 million retail businesses. They found that the average business was only open 40 months. However, it turned out that serial entrepreneurs – those that try, try and try again – had the best chance of success. In other words, prior business experience increases the longevity of the next business opened.  This is exactly what we see with Moustafa.

 3. Christina Wallace

As well as being a highly successful entrepreneur who started BridgeUp: Stem in the USA, Christina co-hosts a podcast and is a senior lecturer at Harvard Business School. But to really understand her story you need to know that she’s 6 feet tall.

It was her height that provided the inspiration for her first startup fashion company Quincy Apparel. She realised that there were plenty of women who felt that most standard sizes didn’t really fit them. So, with her co-founder, she set out to make clothes using a new sizing structure.

After 18 months of hard graft, they had a $1 million in investments. The brand was resonating, the market seemed to be huge, but the company started to collapse. The operational process was just too complex and expensive. As things fell apart, the failure of Quincy plastered across the press, Christina fell into a dark place and didn’t leave bed for 3 weeks.

What does Christina’s story teach us?

Look after your health. Your mental health in particular can take a huge hit while you’re mourning the end of a company.

Research from the University of San Francisco shows that 72% of entrepreneurs report a mental health concern. They’re also twice as likely to report depression compared with the general population.  So, if a low moment in your journey leaves you struggling, be sure to reach out and accept all the help you need.

4. Nick Woodman

Nick is best known as founder of GoPro, the all-action camera company with a net worth of over USD 1 billion. Yet before Nick made it big, things were pretty bumpy.

His first two companies bombed. The second one particular left him scared. In 1999, he started Funbug, a gaming website, where users could earn prizes. He raised USD 3.9 million in capital but a year later the business was dead, killed off by a low number of users and the bursting dot-com bubble.

Reeling from heavy losses he took time off from the start-up game altogether. A big surfer, he concentrated on this. While riding the waves, he realised there was no camera on the market that could truly capture action shots. The rest is history.

What does Nick’s story teach us?

Take a moment to breath. Sometimes, pride means we feel the need to try to bounce back straight away. This isn’t always the most sensible decision. A moment away from everything can clear the mind. It can open new doors and bring new innovative ideas. As Nick shows, they can come from anywhere.

Wear failures with pride

You’re going to fail. It’s highly likely. But as these stories have shown, those failures are part of the process to building a successful company. Learn from them, use them as motivation, because you never know, one day they could be making a movie about you too.