6 Business Leaders You Didn’t Know Failed Before Succeeding

Starting a business isn’t an easy task. In fact, developing your idea and encouraging growth can be a journey filled with adversity.

Even today, building a business is difficult. While businesses can access an array of tools such as B2B Buy Now Pay Later (BNPL) platforms to extend cash flows, social media to make connections, and the internet to access information that supercharges product development, there are still challenges to appreciate.

Of course, these challenges are not new. Even some of the biggest and best in the business world have experienced their own setbacks. By understanding the setbacks of other business leaders, we can recognise how they were overcome.

Playter investigates some of the biggest names in business, their failures before success, and the lessons we can learn when building our own business.

1. Jeff Bezos

You know him as the Amazon founder, owner, and second-richest man in the world. But did you know that the road to success for the American entrepreneur wasn’t as straightforward as his one-click, next-day-delivery business model?

Amazon started as an online bookstore, with Bezos only giving the venture a 30 per cent chance of succeeding. But while the model expanded and evolved to cover a multitude of sectors, other best-laid plans by the commercial astronaut failed to take off.

In 1999, Bezos expanded his e-commerce offerings, launching zShops, a platform that enabled any business to sell online. While the idea doesn’t appear too far from today’s Amazon model, the project failed so miserably that Bezos joked that only his parents and he had ever visited a zShop.

But the failure allowed Amazon to perfect its e-commerce offering, eventually delivering a marketplace model that would act as an intermediary between businesses and sellers, alongside Amazon’s own products.

Other outdone opportunities included investments into Pets.com and Groupon’s rival LivingSocial. Both sites failed, having been closed and absorbed by other businesses.

Within Amazon, products and services such as the Amazon Fire smartphone, Amazon Destinations travel reservations, and video game ‘Crucible’, all failed to gain necessary traction. ‘Crucible’ is estimated to have cost up to $80 million to develop.

Ultimately, these setbacks haven’t deterred Bezos and Amazon from their continued success and growth. Bezos was the first person to obtain a net worth surpassing $200 billion, according to Forbes.

The lesson to learn from Jeff Bezos: perseverance is key. In Amazon’s case, its success was moulded by a combination of its best failures. This comes from recognising the gold in bad ideas and using that to perfect your model.

2. Milton Hershey

Business wasn’t always sweet for Milton Hershey, the chocolatier whose brand would dominate the American confectionery industry. In fact, success eluded the candyman for years before he made his mark.

Hershey showed interest in candy making early. At the age of 14, he began as an apprentice to a master confectioner in Lancaster, Pennsylvania. Four years later, Hershey borrowed $150 from his aunt to set up his own candy shop in the heart of the state. But even after five years of hard work, the accomplishments of his talent were yet to be seen.

What happened next was a transformation. Closing his shop, Hershey headed west to Denver. Working as a confectioner, he discovered caramel and how fresh milk could be used to make it.

But the businessman inside Hershey wasn’t satisfied. Yet again, he attempted to launch his own business in Chicago and New York. Yet again, his ventures failed.

It was only when returning to Lancaster and founding the Lancaster Caramel Company that Hershey found success. The business thrived.

A new fascination with milk chocolate led Hershey to sell the Lancaster Caramel Company for $1 million in 1900. Three years later, Milton Hershey built a huge chocolate factory and an entire town to go with it. Finally opening in 1905, the town of Hershey, Pennsylvania redefined both chocolate production and the candy industry. The rest, as they say, is history.

Milton Hershey teaches us a few lessons about the road to success. Firstly, it takes time to build a business and perfect your products; Hershey moved from confectionary to caramel to chocolate before establishing the brand we know and love today. Secondly, your audience is key and could spell your success. Perhaps the people in Lancaster had a sweeter tooth than those in Chicago and New York. These are both aspects you should consider when building a brand.

3. Richard Branson

Media, hotels, flights, wine, fitness, and even space travel; there doesn’t appear to be much that Richard Branson’s Virgin can’t do. But, while the man and brand have seen success in numerous industries, there have been some failures along the way.

Virgin Airlines are a go-to choice for many holidaymakers, but did you know that the business almost crashed before it started? During the initial test flight of Virgin’s only plane, a flock of birds flew into the engine, causing damage. Without a working plane, the airline could not get certified to carry passengers. Without certification, Virgin couldn’t get the money to repair the plane.

Staying positive, Branson quickly restructured his companies, pulled money from other ventures, and got the plane repaired. Virgin Airlines quickly became the success we know today.

Virgin Airlines is not the only near-miss for Branson. Other ventures have seen failure; his cola company fizzled out, his car sales website stalled, and his wedding dress business was left at the altar.

Branson has had his fair share of failures, but his successes outweigh them ten-fold. The important lesson to learn from Branson: sometimes you can be unlucky. You may hit your own flock of birds (metaphorically, at least), but decisive action and quick thinking can often help you get out of those difficult situations.

4. Colonel Sanders

Your mouth may water as soon as you think of the finger-licking flavour of KFC. But Colonel Sanders is the one to give us a taste of business acumen and perseverance. The Colonel proves that there’s no age limit for chasing your dreams and that they can come true at any point. 

The late growth of Sanders’ business means that he became a billionaire when he was 88 years old.

In his 40s, Sanders started a café on a major highway. However, customers disappeared when a new highway was built, along with his business. Fired from numerous other jobs, he was penniless by 65. It’s then that he took his chicken recipe on the road.

Cooking his chicken on the spot, convincing restaurant owners to sell his food, it’s unbelievable now to learn that he was rejected 1,009 times. Today, KFC has 18,000 venues around the world.

The lesson to learn here is simple: your age doesn’t matter. And when you have a good idea, it may take time before you see it pick up. Just keep going and show your strength and resilience.

5. Vera Wang

Vera Wang aspired to be a figure skater competing at the Olympics. However, the to-be fashion figurehead changed direction after the 1968 U.S. Figure Skating Championships, where she placed fifth.

Wang found herself drawn to fashion when studying in Paris. It was on her return to the USA that the ambitious woman secured a sales position at Yves Saint Laurent. There, she met Frances Stein, who, at the time, was the fashion editor of Vogue. Wang was so impressive that she was hired at Vogue and promoted to senior fashion editor within a year. She was only 23.

However, after 17 years at Vogue, she missed out on the position of Editor-in-Chief. At 40, Wang took on a role as a design director for Ralph Lauren.

In 1989, Wang was engaged, but frustrated by the lack of bridalwear, she designed her own gown. This later led to the opening of her own bridal boutique on Madison Avenue in New York. Today, Wang is considered one of the most iconic wedding dress designers in the world.

Vera Wang can teach us many lessons about taking life in the right direction. Find what you’re passionate about, work hard, and make your own opportunities.

6. Steve Jobs

Steve Jobs is synonymous with the success of Apple. A visionary of personal computing and mobile phone technology, it seems surprising that this entrepreneur briefly lost out on a slice of the Apple pie. However, it can be argued that Jobs’ failure was Apple’s saving grace.

Steve Jobs, Steve Wozniak, and Ronald Wayne founded Apple in 1976, finding success with personal computers in the next decade. You may remember the watershed ‘1984’ advertisement that hailed the launch of the first Macintosh.

However, just one year on, Jobs’ perceived inexperience found him ousted from the business by the board. Jobs was forced to resign when CEO Jon Sculley felt Apple needed to reorganise and shift gears. It was a famous exit.

Jobs continued with his vision, focusing on user-friendly products and technology. He went on to found NeXT, a company that would design and build high-end workstations for use in academia. The platform is the same that Tim Berners-Lee developed the World Wide Web on.

As Apple failed to make sales with overpriced and overcomplicated technology, Jobs returned, ensuring its survival and his legacy. Despite NeXT not achieving the same sales as Apple, it proved his dedication and technological ambition.

The fall and rise of Steve Jobs demonstrate that understanding your audience and your potential is key. When life gave Steve lemons, he made lemonade. When he was given Apple, he made the most valuable company in the world.

Most businesses are not born great, they take time, care, and the odd failure before rising above their challenges. Profiling these titans of business shows us that growing your business can be difficult, but with spirit, perseverance, and belief, scaling your business is more than achievable. Use the tools that you have at your disposal to succeed. Just remember: Everyone fails. But the people who fail most, succeed.