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3 Reasons Skateboarders Make Great Entrepreneurs

Article by: Josh Steimle & Katie Roof


On a brilliant summer's day, skateboarders might seem the last set to be considered entrepreneurs in the making. After all, these teenage kids bear strange clothing and rebellious attitudes and might have offbeat tastes in music.

But look a little closer and it's possible to see the makings of the next Mark Zuckerberg, Richard Branson or Steve Jobs. Skaters' controversial traits are precisely the things that let them defy convention. They may be just the folks to do things other people won’t when they transition from the world of skateboarding to the business scene. 


While there are tens of millions of skateboard owners worldwide, a smaller subset consider the sport not merely a mode of transportation but a lifestyle. They study The Skateboard Mag, Thrasher and Transworld magazines, watch videos at The Berrics site and would rather meet skateboarder Andrew Reynolds than Barack Obama.


Skaters might spend hours every day learning how to switch hard flip down six stairs or land a nollie overcrook down a handrail. You might think they're dedicated or addicted, but in reality they've learned how to make something difficult something so much fun it doesn't feel like work. Entrepreneurs might be able to relate. 

These kids know the industry. They know which companies sponsor which professionals and amateurs. They know that movie director Spike Jonze, who won an Oscar for Her, is a part-owner of Girl Skateboards and that the best skateboards are made of seven-ply Canadian maple. They know about shoe manufacturing, analyze clothing materials and patterns  and can tell if the cut of a particular pair of jeans is just a centimeter off. Instead of listening during algebra class, they’re drawing skateboard designs on graph paper and trying to decide whether Swiss precision bearings are worth the cost.


When these kids grow older, they may not skate three to six hours a day, but they’ll never forget what it felt like to try a trick 200 times for six days before landing it once, and then trying another 100 times to land it a second time. They’ll never stop noticing stairs and handrails and looking to spot a gap or crack in the cement right where a skater could crouch down and prepare to ollie into a trick. 


Here are three reasons a 14-year-old skateboarding son, who can't be nudged to do his homework, might end up as the CEO of a successful tech startup some day.


1. Individualism. 

Skateboarding is inherently individualistic. If a skater can’t land a trick, he or she can’t blame anyone else. Only he (or she) is responsible for the success or failure. While some skaters may have more fun practicing in a group socially, others might have a good time in a driveway or schoolyard alone.


This sense of individualism and personal responsibility translates well to the entrepreneurial world. Successful entrepreneurs don’t blame others for their failings. When they fall down, they get up and try again. They may encourage one another, but they recognize that each individual must pull his or her own weight.

2. Creativity. 

Skateboarding never stops evolving. Twenty years ago, every trick had already been done, I thought. And yet within the past week I’ve seen several tricks on skateboard videos that I've never seen before. Skaters are always looking for new tricks to invent or fresh ways to do old ones.


Whereas most people look at the stone, metal or concrete terrain of a city as a place to work or eat lunch, a skater sees it as a canvas for creating a masterpiece. He sees the connection between a tree root that has grown under a sidewalk, creating a bump, and the nearby cement ledge. The combination of the two presents an opportunity no one else would notice. This ability to see relationships between physical objects in ways others don’t might help skaters see opportunities between two types of business units or how to connect two sets of code to create a more elegant application.


The skateboarding industry has a strong design component. After all, there is little difference between one skateboard deck and another. A shoe manufactured by Lakai isn’t all that different from one made by Emerica, except for its design and the associated brand.


This commoditization of the skateboard industry has produced a rich and vivid assortment of styles and strong brands. Skaters have a heightened sense of color and design, an asset for jobs involving web design, app development, architecture and fashion.

3. Rebelliousness. 

To be a skater is to be a rebel. Skaters must contend with disapproving parents and teachers, power-hungry security guards and skeptical peers. One cannot be a skater without confronting someone who says it’s time to stop playing with these useless toys and grow up. But skaters ignore this and keep on doing what they want.


The entrepreneur is a rebel by definition. He does things most people won't. He starts businesses nobody else thinks of starting. He sees opportunities nobody else does. He takes risks others aren’t willing to take.


Rebels offer hope -- that life is not subject merely to destiny but that humans can be in control and their future is a matter of choice. The next time a skater kid passes by, look past the sloppy clothes and rebellious attitude. That kid might be giving you a job a few years from now.

Tony Hawk, Rob Dyrdeck Tell Us Why Skateboarders Make Good Start Up Investors


Skateboarders make great startup investors, according to Rob Dyrdek and Tony Hawk. The legendary skaters spoke to us about a mindset that helps them be on the lookout for the next big thing.


“The skater mentality is you’re always looking at what’s next,” said Dyrdek. He also spoke of the “NBD” or “never been done” philosophy when it comes to inventing new skateboarding tricks and believes that also applies to looking for startups.


Hawk believes that “being a skateboarder, you have to deal with so much failure and being able to navigate that and accept it, to persevere and push through,” so “that is definitely the key to our successes in other places.”

But it’s not just talk. Tony Hawk has already had some successful exits, crediting his “gut feeling.” He was an investor in Nest, the company that sold to Google for $3.2 billion. He also counts Docusign and Blue Bottle Coffee amongst his active portfolio of investments.


Dyrdek is about to launch an NBC TV Show with Tyra Banks about startup investing. The “Shark Tank”-like business competition show will also highlight the work that Dyrdek does with his “venture studio,” Dyrdek Machine.


In addition to skateboarding, Dyrdek credits his entrepreneurial past in helping him make informed decisions.  “In order to fully understand opportunities,” you have to “see the trials and tribulations of them starting up.”

Hawk and Dyrdek are not the only athletes to get their feet wet in startup investing. Carmelo Anthony has his Melo 7 tech fund and Shaq is a big tech enthusiast.


Many other celebrities have also turned to tech, hoping to reap some of the financial gains that Silicon Valley titans have achieved in recent years. Ashton Kutcher is one of the more noteworthy Hollywood investors, backing things like Uber, Airbnb and Spotify.


There’s no question that being well-known can help them get access to some of the best deals.


“For both myself and Tony Hawk, it’s more the access that you get once you get to sort of an elevated cultural level,” said Dyrdek. High-profile individuals can also use their clout to help spread the word about their consumer-facing investments.


Article by: Josh Steimle & Katie Roof

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