8 Reasons Why Startup Founders Think Like Skateboarders

Thought I should try to document the hours of time and multiple bruises associated with learning a basic skateboard sequence of dropping in and then executing a rock-to-fakie.

Posted by Jeff Yasuda on Sunday, September 22, 2019

As the age-old saying goes, practice makes perfect, right? In basketball, you might practice shooting hoops again and again with the dream of becoming Steph Curry, hitting three-pointers from any range. In golf, hours at the driving range will hopefully improve your inside-out swing, groove muscle-memory and lower your handicap. Mainstream sports are engulfed in the idea of refining and perfecting these fundamentals. 

However, all of this is quite different in the newest sport (or perhaps anti-sport) added to the Olympics: Skateboarding. Skateboarders (aka skaters) need not only have the fundamentals: leg strength, sense of timing, coordination, stamina and incredible balance, but they also need a repertoire of tricks and most importantly, the perseverance to execute.

Skateboard pros aren’t pros just because they can flawlessly execute fundamentals. They aren’t just really good at doing one thing like a 3-pointer. They are pros because they’re learning more movements or tricks, trying them out and, eventually, executing them seamlessly, often in sequence. Skateboarders not only have this constant need to keep redefining their style, but also a drive to learn something new. They need to learn something bigger, faster and more technical to stay at the top. In many cases, the more difficult or scarier, the better. It is a drive to try new things in order to get better… all of the time.

It’s a process of continuous improvement.

It takes a combination of preparation and trial error. You have to prepare yourself well by creating goals, researching, seeking guidance, and envisioning yourself accomplishing this trick. Finally, you just try it and see what happens.  

It’s extremely rare that you nail a trick the first time. Usually, you make several attempts, fail multiple times, learn, try again and sometimes you injure yourself forcing you to take a break from the entire process.. But that’s the cycle: you fail, you learn, you fail again, until you get better, and most importantly, you stay persistent. It’s all trial and error until there’s a small break-through, that bit of learning that gets you to the next step. Watch this amazing video of how this skater tried and tried and tried to land this crazy trick.

For startup entrepreneurs, this cycle probably sounds familiar. I’ve realized that this slow, gradual and often painful process of learning a new trick is a lot like running a young company. It’s all about failing, getting back up, brushing yourself off, and continuing to try until you execute. As someone who has been skateboarding since I was a kid, I believe the parallels are incredibly similar. Let’s get into the mind of a skater and perhaps it can help us become better entrepreneurs.

Stage One: Creating Goals

Set a goal for yourself. It can be daunting to reach that goal. It puts you out of your comfort zone, knowing that hard work, injury, and failure all lie ahead. For me, in skateboarding, my most recent goal was a rock-to-fakie. I shared my video earlier in this post

Brainstorm a plan for this goal and something to work on every day. Your goal’s practice should be a “non-negotiable” part of your day. Diligence and perseverance become your greatest allies. Breaking it down into small steps can help make the goal less daunting.

Stage Two: Research

It’s always important to learn more about your craft and the goal you’re trying to reach. Sisters often watch and learn from other skaters to see what they did and get inspired. Read about what other people have done and how you can play off of their strengths and weaknesses. Learn about the difficulty level and the risks that you would be taking. It’s important to expose yourself to examples of the skills you’re trying to accomplish. Questions are just as important in order to become proficient in a skill. 

Stage Three: Seek Help

If you can get someone to help you, do it. The skate culture is very much about helping learn a new trick and supporting them in the process. You can always benefit from the skillset of someone else. It’ll help accelerate the learning process. An article in the Harvard Business Review suggests finding someone who would be able to notice changes in your progress and give you candid feedback can drastically speed up learning. You need to be humble enough to know when you are beat and need help, but also confident enough to know when your own ideas may be better. Entrepreneurs often can benefit from a founder group or formal advisors who can help provide guidance. An important part of skate culture is to sit around and cheer your fellow skaters on when they are trying to nail a trick. No self-respecting skater would ever admit openly admit this, but yes, it’s a bit like a support group and it works.

Stage Four: Visualize Success

I would often watch other skaters over again and try to imagine myself landing the trick. Where would I place my feet? Where would I land? Pro skater Killian Martin from Spain often discusses visualizing executing a trick like a film in his mind. Check out this CNN Interview.

But the science goes deeper.

Saurabh Vyas, a bioengineering graduate student from Stanford, conducted a study on the motor cortex using monkeys. The monkeys mentally practiced moving a cursor across a screen not physically. The researchers changed the biometric so that brain signals used to move the cursor up now moved it in a different direction. Vyas found that the monkeys adapted successfully. When it came time for the monkeys to execute their tasks physically, they were again successful even when obstacles were presented.

Vyas elaborates saying that when you think about an action you’re about to execute, your neurons are already operating before you even make that first move. Practicing a skill in your mind may help increase the success of your results when you actually come to execute. Vyas believes you still have to physically practice, but setting yourself up mentally by running through what you’re attempting to do may really benefit you. From Tony Hawk to Rodney Mullen, visualization has been important as skaters try increasingly difficult tricks.

Stage Five: Execute

You’ve got to just try the trick and see if you can do it. “No language was ever learned without speaking. No success was ever built without risk and the willingness to fail.” You aren’t going to wake up one day and automatically have a skill down pat. It takes practice, time, and the bravery to put yourself out there. The concept of a developing a MVP is precisely analogous. The product is not going to be perfect, but at some point, every good entrepreneur and skater needs to get beyond just the research and theoretical stage and actually execute the vision. And yes, it can be scary.

Stage Six: Fail and Try Again

After you try it, you’re probably going to fail. I can’t tell you how many times I fell while practicing various tricks. But your focus shouldn’t be on the fact that you failed, it should be on what you learned from failing. If I had given up over every scraped knee and elbow, sprained ankle and broken tailbone, I would have never landed the trick.  

19 out of 20 startups fail. So, to succeed, you need to try something at least 20 times. All it takes is one win, to get to the next stage in your company’s development. If I had given up after a customer loss, investor rejection, or any of the myriad of “no’s” that form the basis of my entrepreneurial existence, I would not have been able to build our business.

Stage Seven: Practice makes Progress

Then it’s all about repetition and trying out new things. Practice. Try out different approaches. Find the method that works best for you so you can accomplish your goal. There’s an idea of a form of practice called “deliberate practice.” It means that you’re not just practicing to practice. You’re practicing with some sort of objective in mind. You should have a goal for each time you go out for a session. Often times, the goal of practicing or trying different approaches is to gain a small insight that would increase your chances of success the next time. The goal is progress, not perfection.

Here’s a great (and long) video done at the VMWare Conference featuring two of the greatest skaters of all time that I mentioned earler: Rodney Mullen and Tony Hawk that reviews many of the concepts that I review in the post…

Stage Eight: Success

Finally, you get that first win. You land the tick for the first time. Congratulations! You should be proud of yourself. However, can you repeat it? How can you still improve? How do you execute this in a way that you have a repeatable process?   

I remember the first time, we thought we had achieved product market fit. We found our first paying customer and landed our first annual contract. It was a celebration. However, it was short-lived as we went out to try to repeat that win with other customers in the sector. We found tremendous difficulty and ended up, as you can imagine, trying a different approach. I’m glad to say that after several trial-and-error processes, we eventually did find product market fit and scale our business.

These eight stages of learning a skateboard trick are analogous to being an entrepreneur. With any skater, or entrepreneur for that matter, a mix of perseverance, smarts, practice, and execution can lead to success. You may not be able to successfully create a business on your first shot, but if you repeat the process and learn from your mistakes, you can win. Congrats, you landed your first “trick” and even better, you may have created a repeatable business.

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