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Everything I Need to Know About Bootstrapping, I Learned from My Waveboard

6/365 Haikus: Inline

I bought a Wave board on a whim yesterday (also known as Swingboards or Shockwave D-boards or Ripstick in other countries), after seeing some very excited looking children using them at one of our parks. (If you don’t know what a waveboard is, any of the video links above should give you an idea of how it works. Suffice to say that it is to skateboards as inline skates are to rollerskates.)

After purchasing the board, my friends and I brought it to a relatively empty space in the middle of Eastwood, where I proceeded to stumble, stagger and curse loudly for the rest of the afternoon. (Minor disclaimer: my past experiences relating to skating of any kind are as follows: one afternoon in the late 90s at a skating park, and 45 minutes at an ice skating rink two years ago. In other words: none.) It occurred to me afterwards – or more accurately, after I had taken my umpteenth tumble – how the whole experience was roughly analogous to bootstrapping a business, something which I’ve been in the process of doing for 4 years now. Specifically:

1. Theoreticals are overrated. There is only so much you can learn from following Guy Kawasaki, or subscribing to Seth Godin, or watching RailsConf videos, or reading a badly translated scrap of paper explaining how to “launch forward with new board.” At most, these veterans and experts are making broad generalizations that will hopefully make sense to the largest section of their respective audiences as possible. The specifics though are completely up to you, and from what I’ve learned thus far, it’s these minute details that can really kill you. The other danger in relying on your references is that you may delude yourself into believing that you actually know this stuff just because you’ve read every single book and blog entry on the subject. Brother, unless you’ve actually tried it, you don’t.

2. Embarrassing yourself thoroughly is part of the process. The only people who don’t make mistakes on their first ventures are those that lied on their resumes. A lot of key business decisions are counter-intuitive, just as trying to learn how to balance while standing still is the worst way to learn how to waveboard. Office space, external funding and picking your team are all areas I’ve totally screwed up on in the past, and it’s only now that I realize how silly those early, amusingly naive judgement calls really were. You will make mistakes, and people will make fun of you for it. You may as well accept that now. Too many people are so paralyzingly afraid of being laughed at or ridiculed that it prevents them from even giving it a try, and this goes for both waveboarding and bootstrapping.

3. Sometimes you just have to let go and hope. There is a veritable boatload of things that you cannot control. These include imperfections on the road surface, presence of small children and animals, lack of railings separating solid and liquid sections of the park, and (later) partial insobriety. These things threaten your progress but there is very little you can do to mitigate them, except perhaps for the last example. Either that or you leave the park and go somewhere else. You can do as many SWOT analyses as you want – those external factors will still be outside of your sphere of influence at close of business. Accept that they’re there, and just move on.

4. Not everything can be evaluated and analyzed. Some things work even when we don’t understand how they work, and indeed had nothing to do with making them happen. To properly ride a waveboard, you get your left foot on the front platform, push off hard with your right foot and somehow, the skater gods imbue the board with enough stability for you to balance for a second or two with only one foot on it. Then you rest your right foot on the back platform, and start making twisting motions with your feet to keep the momentum up. If you do this properly, you can keep going forever. Similar things happen in the business realm, and the example I like most has to do with the people you work with. You don’t necessarily know what their motivations (beyond the economic) are, and your visibility into their lives outside of the office is limited at best. And yet even with shitty startup pay and crappy working conditions, sometimes you get real superstars working with you. People who work their asses off for you, just because. There’s an intangibility there that you’re not supposed to measure, just acknowledge.

5. Keep at it. I woke up this morning and noticed the parking lot at my building was unusually quiet. So I took the board out and rode around the lot a few times without taking a spill. (A first!) By the end of my second round I was getting pretty happy with myself, so I decided to up the ante a little and pick up speed. Knees bent, arms at my sides, I was gonna break some barriers today. Turns out though I didn’t really know how to do that properly yet. The board flew out from under me and I ended up sprawled on the pavement. No broken bones, but I don’t think my right knee really enjoyed the impact. I picked myself up, dusted myself off, and proceeded to do one more (slightly more cautious) round before putting the board away.

There’s no trick to bootstrapping a business, just as there’s no trick to learning to waveboard. If you keep at it long enough, you’ll just get it.

The Blur

(Photo by Marco The Site Guy)

Reader Comments (7)


As I sat in the hospital on Christmas morning the only other people in there were a family with a girl who got a waveboard for xmas. First time she stepped on it, lost balance, fell, broke her wrist and off they went to hospital. Lesson? Fail early? (questionable in this case if it will become fail often.. parents don't really help the startup cause ;)

January 12, 2009 | Unregistered CommenterHunter Nield

Ouch. I'm glad you're getting the hang of it, though. :D

January 12, 2009 | Unregistered CommenterLizz

Hey Luis,

Congratulations on trying something new.

"If you keep at it long enough, you’ll just get it." is also sound advice.

January 12, 2009 | Unregistered Commentermikey316

What I actually don't like about the waveboard things is that it reminds me that I don't believe there is a strong trick system that exists for it. That and I'd rather have the instantly-recognizable skateboard over one that is plastic and has some wierd decals on it.

On that note, all the things you need to successfully waveboard is also the same things you need to learn how to skate.

Found this blog by googling about skateboarding plurkers... I guess thats technically what I found.

Also, the post about plurks and twitter's numbers are quite telling. Maybe I should get a twitter and use your Mechanical Plurk instead.

January 14, 2009 | Unregistered CommenterPuff


You're correct in that the tricks system on a waveboard is a lot less deep than with a skateboard. However, I imagine I belong to a large section of the skating population that are not athletic enough for that to matter.

Glad you're thinking of giving Mechanical Plurk a try, btw.

January 14, 2009 | Unregistered Commenterluis

Hehe, I always believe that if you have the patience to learn the board then there's always the same patience to try and start jumping on it.

I've yet to learn ollies myself, but I've did a few on the grass before. Haven't had time to practice in a while.

Give us updates on how the waveboarding goes... those things can go up hills without getting off - that's actually something skateboards can't do.

January 14, 2009 | Unregistered CommenterPuff

Interesting analogy. Though if it were me, I'd probably equate it with learning to swim without a life vest... and nearly drowning :D ('twas probably one of the worse experiences of my life hehehe)

BTW what happened to your Mechanical Plurk whale? Looks less violent now :P

January 17, 2009 | Unregistered CommenterGail

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