Shut Up and Skate

Growing up in Midcoast Maine, my favorite pastime was spending endless hours at the skate park grinding down rails, learning new tricks and getting a little better each day. I still grab my board now and again to let loose, but as a grown up, my favorite pastime (and my vocation) is building products. Skateboarding to some probably conjures up images of pot smoking, booze-addled teenagers, but much of what I learned trying to land a frontside 360 has lent itself to a career as a developer and entrepreneur.

To me, the clearest parallel between skateboarding and building a startup or a product is that success in either depends largely on self-motivation. There’s no coach screaming at you to try harder, and investors and customers won’t be lining up to encourage you to make something good.

Unfortunately, tech startup culture (not unlike skateboard culture) is full of posers. We all know that guy: talking up a big game, dropping words like “pivot” and “Andreessen” (he doesn’t know either). But when it comes to actually building a product, or even demonstrating demand for an idea, he’s got nothing to say. At the skate park, these were the guys with the impeccable Vans, trying so hard to get sponsored, but not very interested in learning how to skate.

Serious skateboarders learn a single trick at a time and perhaps more importantly, learn to value progress instead of instant gratification.

Mastering the Basics

When you first step on a skateboard, it can be a little intimidating finding your center of gravity and learning the basics. But eventually, you’ll land your first ollie, then a kickflip and over time you can experiment with ways to combine & chain the moves into a new one. But first you must nail the components individually. Building a business follows similar mechanics.

Say you’re trying to launch and monetize a new platform for digital media. There’s a million ways to do it and indeed, it’s been done a million different ways. But that shouldn’t discourage you. Finding success will be a matter of studying the basics behind what makes similar ventures work in the first place. All you need to do is bring one or two original twists to the project, as well as the monetization model. Maybe all you need to do is provide content for free that would otherwise live behind a pay wall, and then monetize through ads. Maybe it’s the opposite.

Figure out what works, and then make it work for you.

Leveraging Past Success

You can’t land a 180-kickflip without mastering both a regular kickflip and a front-side 180 first. After you have that down, maybe you’ll want to chain together a few moves and finish off with a rail grind. The point is, you start off small, with basic tricks and before long, you’ll be turning heads like Tony Hawk.

Developing new products reflects similar dynamics. Your first few endeavors can be painstaking because you’ll spend a lot of time on basics, like cold-calling potential customers. Eventually though, these things become background processes and you’ll be able to devote more of yourself to the bigger picture — chaining together your basic proficiencies into new, complex and hopefully very lucrative projects.

Learning to Enjoy (and Trust) Process

Perhaps the most useful wisdom I’ve been able to apply to business from skateboarding is the ability to find satisfaction in even the smallest victories — and the importance of trusting consistent execution toward a strategy.

Do the initial research. Commit to a process. But keep self-aware & learn from feedback.

Success will ultimately come down to your mentality. Are you in the game to learn how to skate, or to get sponsored? Would you skate anyway even if you weren’t sponsored?

You can’t fake passion, whether in the boardroom or at the park. So just shut up and skate, or go home.