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A few days ago I was watching a couple of skateboarders out front of my house. For some reason, skateboarders have decided that my little block of west end family living is a pretty damn good place to skateboard. Unlike some of my elders in the community, I really don’t mind. In fact, they often provide entertainment for my son and daughter who enjoy watching them glide along and also are fascinated by the occasional tumble. Those of you who have read my stuff before know that I tend to connect a lot of things that don’t seem immediately related or connected. And so it is that I came to realize that entrepreneurs can learn a lot from skaters and the best startups go through a process pretty similar to learning to board.

Minimum Viable Product

MVPAlmost anybody will tell you that close enough is often more perfect than perfect is and that when you’re in the initial stages of getting your product to market, perfection is not the goal. The goal is to ship. The goal is to put a product out there that customers have an interest in. Perfecting features and interface can be a long, grueling process and for a lot of startups, their runway runs out long before they lift off. But the very best have learned that you don’t have to be the very best to launch. You just have to have a great idea and a functional example. Nobody understands that better than a boarder.

Every skater just wants to land it. It doesn’t matter if it’s pretty. It doesn’t matter if it was exactly how the pros did it. It doesn’t matter if they can’t necessarily duplicate it. Every skater just wants to land it. They don’t hide out in a basement practicing moves until they can nail it. They get out there and they show people what they have. It attracts like-minded individuals and suddenly they’ve got a partner that they skate with. And neither of them are interested in absolute perfection. Landing it is landing it. End of story.


oneWhile it might be true that they’re perfectly happy with just landing it, that’s not the end game for most skaters. They don’t hit it once and walk away. They’re constantly striving to improve. They add their own flair. They do things just a little bit differently each time, just enough that they’re mixing it up. But what they don’t do is stop working at it. You don’t see guys sitting around say “naw, it’s cool. I’ve already done an ollie off that so I’m good. I’ll just sit here and hang out.

Most skaters love skating as much as you love your idea. In fact, probably more. But they understand that the idea, the focus, the move, is the beginning of the story, not the end. They’ll grow and change, discard movements and add new ones, continuously trying to do something better and different. This is how the best startups work. When they’ve blown up, they don’t just sit back. They pour everything they have into making that thing better. Or they find another thing. But the reason you don’t find a lot of fat skateboarders and out of “work” startup people is one in the same; they’re too busy doing things to slow down or stop.


bikeWhen I was younger, I was friends with a kid named Freddie who was really into trick biking and skateboarding. I was really excited to impress Freddie who was older and seemed exponentially cooler than me. So I’d try to figure out new ways to do something interesting on a bike or on a skateboard. One particular incident stands out above all the rest when it comes to the pain that comes from striving to impress. I was sitting on a long board, trying to make it down a relatively winding pathway when suddenly I hit a bump. My hands slipped off the side of the board and I rolled over every single finger on both hands with the skateboard wheels. Despite not breaking anything, it was agony for several days with the simplest of tasks become downright impossible.

That was not the last time I was ever on a skateboard. The fact of the matter is that anything worth doing is worth doing despite pain. I’ve yet to hear from a startup that just says, “yeah, we had an idea and everything worked out. It was really easy and painless.” Maybe that happens. I’m sure it HAS happened. But not often. Unfortunately, launching something, from ideation to consumption is a process with fraught with peril. But like skateboarding, the end result is so fantastic that you don’t really care about what it looks like or feels like along the way. You just want to get there, no matter how many of your fingers you run over.

That’s A Shitty Deck

deckWhen it comes to skateboarding, like almost anything really, there’s a market for overpriced crap that doesn’t help you any more than the cheap stuff does. Most skaters don’t have the money to go out and buy brand new, “top of the line decks” all willy nilly whenever they feel like it and those “top of the line decks” are basically just really pretty versions of the same stuff you can get for a fraction of the cost. So the question becomes, how useful are your tools?

I watched a guy just shred the top of his board the other day. Just ran it across a bar like he was trying to whittle something. It took a huge sliver out of his board and left it looking like it had seen better days. But here’s the thing; it still worked. Perfectly. The fact is that most tools, especially the ones with really pretty front ends or some sort of gimmick, are just garbage. There are a hundred apps to help you make a list on an iPhone. Some of them are paid apps and do the exact same thing that reminders or calendar do, though often without simple integration.

Use tools that work. Don’t use tools because that’s what everybody else is using or you heard one guy, one time, talk about how great it worked. Use tools that work. It doesn’t matter if they’re pretty. There’s a free alternative to almost any tool out there, from project management tools to visual design tools. Just today, someone asked me how I personally would respond to a client who suggested that they could do what I do because I’m using some sort of free template builder. If you think you can do it better, then go do it better. If you want to use the same tools I’m using, feel free. But don’t think that your startup is going t blow up because you’ve bought expensive software.

launchIt’s gruelling. It’s incredibly difficult and the better you get, the harder the degree of difficulty in your trick. This means increased chances you’re going to hurt yourself and if you do, increased chances you’ll hurt yourself badly. And then there’s skateboarding. The fact is, a huge proportion of startups fail for a very simple reason; some people just don’t know how hard the work is going to be and they’re not equipped to get it done. Not being able to successfully launch a startup is not a condemnation of you as a person. Some of the best minds I know would be shit entrepreneurs. It’s a skill set thing. The next time you see someone skateboarding, think about whether or not you could put yourself through what they put themselves through. If the answer is no, don’t launch a startup.