dreamstime_xs_33071167 (2)The second episode in the Hobbit trilogy is set to swamp our cinema screens this month and there are more than a few similarities between the journey Bilbo Baggins takes on Middle Earth and the journeys of some of our most successful entrepreneurs here on Planet Earth (and I’m not just talking hairy feet here).

Risky Business

At the beginning of our hobbit’s journey, Bilbo leaves the security of his home in the Shire to go on a seemingly unattainable quest for dragon’s treasure with a bunch of dwarves – a risky and foolish move – and comparable with the beginning of the business journey taken by Britain’s own Sir Alan Sugar. (Ok, so none of his business partners are as vertically challenged but there is something distinctly hobbity about Sir Sugar – that curly hair perhaps?)

Sir Alan took the risk of dropping out of school at 16 and then took another one by leaving a safe civil service job as a statistician at the government’s Education Ministry to start his own quest for wealth by selling car aerials out of a van. Since starting his Amstrad electrical goods empire, he has now amassed a fortune of around 800 million, and regularly ranks in the top 100 Sunday Times Rich List.

Despite Sir Alan’s fortune being in pounds sterling and not in the usual dragon’s hoard of jewels and gold cups (although being the ex-owner of Spurs Football Club he’s been close to one a few times), he shares more than a few personality traits with old Bilbo, as he explains in his own words: “What you need is sheer determination. Passion and great personal belief. And a slice of good luck.”

Lucky Charms

Good luck is something Bilbo had in spades – finding Gollum’s precious invisibility ring at just the right time; the eagles coming to the rescue when all hope seemed lost – and that ‘right place, right time’ type of luck is a theme that runs through the lives of most of our famous entrepreneurs, or at least knowing how to use luck to their advantage.

With Bill Gates the luck came early on. When he was 13, his school raised funds in a rummage sale but instead of using the money in the usual way and buying books, it opted to buy a Teletype Terminal 33 ASR. This was how the computer genius first learned to programme. Later on, when he got banned by Computer Center Corporation (CCC) for exploiting bugs in their operating system, he converted that piece of bad luck by offering to find bugs in CCC’s software in exchange for computer time which in turn led to him being hired by Sciences Inc. to write a payroll program. He went on to receive royalties on the program which gave him the capital to start his empire.

But the path of many entrepreneurs has not been as smooth and obstacle free as young Bill’s but more like Bilbo’s rocky road to the Misty Mountains.

Obstacle Course

In the case of the grande-dame of female entrepreneurs Oprah Winfrey, her journey was so fraught with obstacles that it’s a wonder she made it through at all. Brought up in dire poverty, she fled her Milwaukee mother’s home at the age of 13 after suffering years of alleged sexual abuse by family members. She was picked up by the authorities and sent to a juvenile detention center but it was so overcrowded she was denied admission. Oprah ended up living with her estranged father in Nashville – a strict disciplinarian who insisted she read a book and write a report each week. (No doubt the seeds of Oprah’s Book Club were sewn right there.)

By taking her father’s advice of concentrating on her education as well as using the positive influence of her grandmother, Oprah rose above her difficult circumstances and went onto become one of the richest and most influential business women in the world.

A Tangled Web We Weave

Oprah is famed for her honesty and it’s one trait that elevates her above the usual wheeling and dealing attitude in some business corners. But for one entrepreneur it was the lies that got him noticed in the first place.

PT Barnum, the 19th century businessman and founder of the hugely successful Barnum circus & museum, will always be remembered for promoting hoaxes such as the Feejee Mermaid and General Tom Thumb – a four-year-old boy claiming to be an dwarf-like 11 year-old. (I knew I could crowbar a dwarf in here somewhere).

But just like Bilbo, who managed to extricate himself from the sticky webs of the monster spiders in Mirkwood, Barnum got out a tangled mess of bad investments leading to years of litigation and public humiliation, simply by keeping a calm head. With a bit of help from his dwarf mate Tom Thumb, he set off on a European lecture tour which after four years allowed him to emerge from debt and buy back his museum of curiosities.

Patience, patience!

Barnum showed enormous patience during those lean years but one entrepreneur who had to learn the lesson of patience the hard way was stockmarket millionaire Warren Buffet.  Just as Bilbo thought he could make a quick profit by nicking off with one of the gold trophies on his first visit to the dragon’s den, the precocious 11-year-old Buffet thought he could make a quick buck when he bought three $38 dollar shares in Cities Service. But when the stock fell to just $27 per share, plucky Warren held on until his shares bounced up to $40. But he didn’t hold on for long enough – a decision he would soon come to regret when Cities Service shot up to $200. The experience taught him his first basic lesson of investing: patience is a virtue.

The Long & Winding Road

So there you have it. When it seems like your path to riches is riddled with goblins who want to bring you down or trolls who revel in your failure, just remember Bilbo’s journey, steel yourself with a little courage and be thankful you don’t have to earn your living by bagging your swag from under a dragon’s belly.