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It may appear a strange link to make; what could teenagers spending hours a day on a skateboard and a successful entrepreneur of a multi-million rand empire possibly have in common?

What do you see when watching a skateboarder throw themselves down a set of stairs five, six or twenty-four times before they stick some sort of flip-spin-trick down those same stairs, which they have been trying to do for the last hour?  To most, these “rebellious” skateboarders don’t have much ambition or drive in life, right? It couldn’t be further from the truth.

One usually associates the entrepreneur with words such as: dedicated, resilient, creative and determined. Coincidently, the above mentioned traits can be used to describe most skateboarders that throw themselves down stairs.

Both types (entrepreneurs and skateboarders) of people have the common trait of defying convention; of course one takes place in a business environment while the other takes place on the street – both extremely testing environments where one has to be able to think on one’s feet (no pun intended) and sometimes are forced to make or break decisions.

Tony Hawk

Tony Hawk – Skateboarder/Entrepreneur.

One of the most iconic and successful entrepreneurs born from skateboarding is Tony Hawk, with an estimated total net worth of $120 million (yes, US dollars!).

Hawk, turned his profession into an empire by starting his own skateboard company Bird House Skateboards, Hawk Footwear and being the vision behind the hugely popular series of video games, oh no fewer than twenty-one variations.

“My definition of success is doing what you love. I feel many people do things because they feel they have to, and am hesitant to risk following their passion. And obviously, yeah, it’s hard right now. But maybe there’s a chance that if you get laid off, maybe that’s your saving grace, your chance to restart.” – Tony Hawk

Many see the skateboarding lifestyle as a dead-end activity; however, would those many still feel the same way knowing the fact about Jason Lee from the NBC series’  My Name Is Earlwhom was a fully-fledged sponsored skateboarder making a living from doing what? Skateboarding only, until his acting career blossomed.

The important characteristic straits shared among most skateboarders are extremely valuable for the entrepreneur:


The only constant is change;  when everything within the environment is changing, the floor is never going to be perfect and smooth on the landing of those twelve stairs so you improvise – take along some wood for the landing, go full DIY and concrete the landing yourself. Skate-boarders look at everything differently; a pavement with a lifted tile isn’t an inconvenience which you need to avoid but something you embrace: “How could I turn this obstacle into something to my advantage?” Similarly with business and the corporate world, when technology throws a curve ball at you, outdated systems require new approaches, a different way of thinking: “How can I make what’s in front of me work to my advantage and possibly turn into something financially fulfilling?”

A great example of something used purely out of opportunity and necessity was taken by the mainstream and has found its way into fashion by none other than the conventional: shoe lace belts. Shoe lace belts are being marketed by popular denim brands as, “Fresh and Hip” – something those skateboarders have used for years due to not having an actual ‘conventional’ belt:

Shoe Lace Belts:

Shoe Lace Belts

The Shoe Lace Belt


This is probably the most essential trait an entrepreneur aspires to: to make or break your business venture, to stand out from the crowd – the immensely competitive business world.

When there is only a skateboarder with a skateboard he or she is completely responsible for one’s actions, with no one else to blame but you. This is something the entrepreneur values – a strong sense of self, and self-reliance goes a long way in the business realm.

Individualism creates innovation; skateboarders with their eccentric style, use of colours have the ability to “stand out” among a crowd; within certain job markets such individuals are sort after: fashion, all types of design and architecture are just a few industries where a keen eye for detail and degrees of individualism makes a significant difference.


Rebelliousness goes hand in hand with skateboarding; individuals defying the norms of society, taking a fresh view on things, an unique approach to the same situations, seeking to get the most out of something and make it their own. There are many negativities such as, “You cannot… make a living doing that” often faced by the skateboarder, and guess what?

The starting entrepreneur will hear the exact same things, and both take these “You cannot…” and use them as motivation to succeed – adding fuel to the flame, being able to overcome and do precisely what they set out to do.

The entrepreneur seeks to make things happen where there is a gap, an opportunity to defy the norm, takes charge and takes that leap of ‘believe’.


“The Rebel”


At times the skateboarder will try the exact same trick for years before they eventually get it right, then they’ll never stop doing it and with time that impossible trick gets easier – taking into account previous failures, a skateboarder will change their approach, adapt and eventually work out the formula of how to perform that switch-front-side-nose-grind-down-a-ten-stair-handrail.

The entrepreneur may not succeed on the first venture, it may crash and burn but do they give up? An innovative entrepreneur returns to the drawing board and evaluates what went wrong and how they can make small (or large) adjustments and changes to ensure on the next approach things succeed.

Both groups of individuals strongly value determination – one will not succeed in anything without taking determination to levels beyond all levels.


Determined, Until Something Gives.

Embracing the rebellious, creative, determination and individualism of skateboarders could pave the way for establishing more entrepreneurs within the work place.



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One Response to Skateboarders As Entrepreneurs – Who Would Have Thought?

  1. Nicola Beykirch says:

    What an inspiring piece, Tyrone! My eyes have been opened further, popping almost. Skate-boarders and entrepreneurs in the same breath – absolutely, who would have thought!

    My mind is now torn; do I take up skateboarding or ‘entrepreneuring’? If skateboarding shall lead me to becoming an entrepreneur then my mind no longer needs to be dealing with such a tear.

    You must have tips on where to purchase a top ‘board’ from.

    Oh and I think the Hawk needs to be interviewed – a follow up blog piece, perhaps? I do not doubt you are with ability to make it happen. If you cannot make the date with the Hawk, I shall reschedule my diary and fill your skating boots.

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