The Seemingly Unbearable Failures of some of the World’s Billionaires

Doesn’t it seem unfair whenever we experience mistakes and failures in our career or business? The feeling makes it even more unbearable when a friend reads us a positive quote on failure and how we must embrace failures and learn from it. Yeah, right. It’s easier said that done.

But what if it’s all fair, after all? All of us experience mistakes and failures at some point in our productive lives, it just all depends on how we react to it. Either we pick up from where we were, learn a huge deal from it, and push ourselves some more, or, dwell on our mistakes and regret our past for the rest of our lives.

Nobody is immune from failure. Here are some of the failures of the world’s wealthiest billionaires:

  1. The many failures of Sir Richard Branson

He is the ultimate success-after-so-many-failures story. We all know Sir Richard Branson as an eccentric, down to earth billionaire who owns Virgin Atlantic, Virgin Galactic (the world’s first commercial spaceline), and Virgin Records. Of course his success is a product of the back to back failures of 15 or so of his business ventures.

As Mr. Branson himself mentioned in his blog, “Whether it is launching companies like Virgin Brides and Virgin Cola that fell flat on their face, making the wrong call on investments, or simply forgetting to return a call or send an email, I have made hundreds of mistakes. I’m sure I’ll make many more this year, and learn valuable lessons from every error. Anybody who tells you they don’t make mistakes has just made one.”

Virgin Cola is the most famous and the proudest failure of his business life. As a result of this widely publicized failure, he learned from it and said: “That business taught me not to underestimate the power of the world’s leading soft drink makers. I’ll never again make the mistake of thinking that all large, dominant companies are sleepy!”

His Virgin Brides (no pun intended) venture which opened its doors in all of England in 1996 had a short-lived future. It ceased in 1997, due to the intensely competitive market for bridal gowns. It was so competitive, he had to shave his beard and wear a wedding gown as part of its marketing stint. Don’t believe it? Here’s proof.

Sir Richard Branson, Commissioner, Global Commission on Drugs Policy; Founder, Virgin Group

Sir Richard Branson, via Chatham House

2. Bill Gates, whose company Microsoft missed out on improving its search engine, the biggest thing that happened to the internet

Who would’ve though that someone so big can still fail to see a billion-dollar opportunity? Microsoft’s MSN search and Google were both born in the year 1998. At the time Microsoft already had a booming tech business, and had a lot of business ventures on its plate. MSN search was just an ordinary search tool that fairly did its job, but Google founders Larry Page and Sergey Brin were on to something better – something that provided a better experience for the end-user. Google focused on the algorithm and near-perfect usability of its search engine, and introduced a one-of-a-kind search tool early users of the internet never thought they needed.

“Google kicked our butts.”, admits former Microsoft CEO Bill Gates.

Bill Gates @ the University of Waterloo

Bill Gates @ the University of Waterloo. Source: Mohammad Jangda

3. Oprah Winfrey, on prematurely launching her own TV network

Announced in 2014 by Forbes as the successful woman who remains the only African-American billionaire, Oprah Winfrey was also susceptible to failure. At the time of the launch of the Oprah Winfrey Network (OWN) in January 2011, Oprah was not yet done with her duties on the ‘Oprah Winfrey Show’, which ended May 2011.

Oprah told CBS News: “It’s like, having the wedding when you know you’re not ready. And you’re walking down the aisle and you’re saying, ‘Oh, I don’t know if we should be walking down the aisle. Maybe we should have postponed this. … I would have probably waited until I actually finished ‘The Oprah Show’.”

Although she has millions of fans and following, her TV channel still failed to gain traction 15 months after and had to lay off a few workers. It’s a good thing that the OWN managed to survive this tough period and is thriving as of writing.


Oprah Winfrey receives 2013 Presidential Medal of Freedom. An official White House photo [Public Domain]

4. Google’s Larry Page and Sergey Brin missing out on developing their own Social Media product early on

Bill Gates failed to see the hidden opportunity in search engines, but the Googlers who ‘kicked the butts’ of the guys at Microsoft also failed at something else that is equally huge.

When Google offered the now gaming website Friendster a whopping $30,000,000 back in 2003, Friendster didn’t sell. They could’ve taken that as an opportunity to develop their own and make it better, but instead, they waited seven years before creating Google Buzz and then Google Plus a year after, which up to this day is still struggling to achieve a sizable share of users.

Eric Schmidt, Sergey Brin and Larry Page

Eric Schmidt, Sergey Brin and Larry Page. Source: Joi Ito

Now, on to some more examples that our closer to our shores (the Philippines, that is)…

5. Tony Tan Caktiong, founder of Jollibee Foods Corporation, spent so much time and money on a product he though was bankable.

Mr. Caktiong said in an interview with Rappler: “We thought that (barbeque chicken product) was our best product. We did a lot of work on it. But it didn’t do very well. Do I call it a major mistake? Maybe not a major mistake but it’s a failure we have in our history.”

And it’s not only barbecued chicken that they spent so much of their resources on, only for it to fail. The list include Copenhagen ice cream and Mary’s Chicken. “Failing is just an experience or a learning. If you can pick up some learning’s then it’s worth it. It’s like paying tuition fee,” Mr. Caktiong said.

6. Andrew L. Tan of Megaworld, Emperador Distillers, and McDonald’s Philippines experienced failure early on as a young entrepreneur

He acquired his first major business venture in 1979 when he bought a liquor factory and later on realized how tough it was to compete as a small player with the major players in the Philippine liquor industry. In an interview with Yahoo!, he mentioned “But as I soon found out for myself, success does not come the easy way. My first attempts to produce gin and then rum both came to naught. I even lost money because I was on a head-on collision against liquor giants that had lorded it over the business for ages. Despite all these challenges, I never gave up.”

Stay rich,

Have you experienced the ultimate failure yourself? How did you get up from there? Feel free to Share Your Story, comment, share your tips, or ask a question. Please also like me on Facebook and Twitter! Thank you!