Five business giants who failed first time around

It's very rare that entrepreneurs hit the nail on the head first time; so here we look at five of the biggest names in business history and their less than auspicious beginnings.

Rejection is, we’re told, something that entrepreneurs have to deal with throughout their careers. For every successful funding round there is a door that is closed firmly in their faces.

But sometimes it’s not just others who fail to see the money-making potential of their ideas. More often that not the first ideas people have simply aren’t that good. Hopefully giving encouragement to anyone out there who is still yet to have that killer innovation, we have a look at ridiculously successful businessmen who didn’t quite hit the mark first time. If this lot were once this bad, surely there’s hope for us all…

Bill Gates – Traf-O-Data

This goes to show that even having the right team isn’t always enough. Gates and Microsoft co-founder Paul Allen founded the horribly-named Traf-O-Data back in 1972.

The idea was to automate the process of collating data from passing traffic. Hardly a thrilling idea by modern standards, but at the time it did address the issue of how many man hours it took to perform this task.

Despite this, the idea never really took off and the company was would up only a few short years later. However, it did provide Allen and Gates with crucial experience when setting up Microsoft shortly afterwards.

Arianna Huffington – Frustrated author

Nowadays anyone with a laptop knows the name Huffington from the hugely successful media juggernaut The Huffington Post. Launched in 2005, it has grown into one of the biggest names in online news and commentary. But Arianna was well into her 50s by the time all of this happened, and not all of her previous efforts were quite so successful.

In the 1970s she was a budding author looking for her big break. One book that did make it, The Female Woman, was widely attacked for its regressive views on feminism. With claims such as women’s liberation only being likely to help “women with strong lesbian tendencies”, it’s not hard to see why.

>See also: Six sportsmen who went into business

But Huffington has transformed herself as a largely-liberal media mogul over the years, proving that reinvention and redemption are truly achievable goals.

Jack Dorsey – Twitter before Twitter

Back in 2000 Twitter founder Jack Dorsey was working on his first passion – taxi and ambulance dispatch technology. Believe it or not it was not following this particular path that was to make Dorsey his fortune.

But it was while working on this technology that the innovative tech entrepreneur first had the idea for a platform in which users could track their friends’ activities. But sadly the technology, and the world, was not quite ready for this kind of media yet. It wasn’t until he tried again in 2006 that others finally caught up with his vision.

Even after this though things haven’t been plain sailing for Dorsey. He was effectively ousted as Twitter CEO in 2008 amid allegations of poor management – a salutatory warning that being a great innovator doesn’t always make you a great leader. 

Henry Ford – Detroit Automobile Company

Today Henry Ford is rightly hailed as the greatest American industrialist of the 20th Century. But before his eponymous success there were a few stalled motors along the way.

In 1899 Ford founded the Detroit Automobile Company through investment from the town’s mayor and two other wealthy benefactors. Sadly the cars cost far too much to make are were widely considered to be terrible. 

But in 1901 the company was effectively dissolved and the Ford Motor Company was born. Whether it was having his name attached to it or his chastening experience of failure, something spurred him on to make a much better fist of it the second time around.

Mark Cuban – Pretty much every job he did

Mark Cuban sold his company to Yahoo! in 1999, pocketing a fairly handy $5.7 billion in the process. He has since gone on to run more companies than you could shake a stick at, as well as a few major US sports franchises.

But back before any of this he seemed incapable of doing anything properly. Failed stints as a cook, barman (where he purportedly couldn’t de-cork a bottle of wine) and a carpenter were just some of the mis-steps he suffered on the road to success.

His personal fortune is now estimated to be somewhere around $3 billion, so it just goes to show some people are brilliant at launching and maintaining hugely profitable businesses but terrible at pretty much anything else. I’m assuming someone else opens his wine these days.

Further reading on innovators: The secrets behind Europe’s top investors and entrepreneurs

Praseeda Nair

Praseeda Nair

Praseeda was Editor for from 2016 to 2018.

Related Topics

Female founders