Most Americans want to own their own businesses. The only problem they see, though, is just how much money (capital) it takes to get one up and going. And so they save (or not!) and wait for the opportunity to have enough cash to start their dream business.

But as anyone who’s ever started their own business knows, the best time to start a business is last year. So it’s better to get started now on a small scale, and ignore the need for infinite capital and perfect situations. I’ll give an example of how I started my current guerrilla business.

Right now I have a few websites that generate a decent amount of money. The problem is, they require a lot of time and effort, the majority of which is spent in front of a computer. I don’t enjoy time spent in front of a computer as much as I used to, and would much rather spend my time pursuing the things that really interest me.

And the thing that really interests me right now is skateboarding. I love how much of a positive influence it is on kids, and how much it helps kids become self confident and starts them thinking for themselves. There are no coaches in skateboarding, and there’s no real competition. Each person has their own way of skating, and each way of skating is an expression of their own personality. There’s no right or wrong way to do it.

So I started devoting my time to starting a skateboard company. I don’t have nearly the savings necessary to buy a few hundred skateboard decks and shirts, but I do have the time to think of innovative ideas for t-shirts and skateboards, and what kind of a company I would build.

I don’t have a computer set up for digital graphics, but I have friends who do. Rather than spend the money for a complete graphics set up, I used their Apple to do a few first couple of graphics. I don’t have the money for a complete silkscreen setup, so I collaborated with another one of my friends who was doing a few homemade screens. We spent in total about $30 setting up 3 screens.

I had t-shirts laying around, so I made my first few t-shirts, and started wearing them around. The first day I wore one, I had 8 people ask me for one. That’s when you know you’ve got a good idea.

Stay small. There is no reason to acquire capital before you’ve got an idea you know works.

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Sarasota is pretty fun, but Tampa is the definition of awesome, so I left early the next morning. And 41 was awesome the entire ride up.

For some reason, there is a huge (almost an entire other lane!) median from Sarasota to Tampa. I could really relax as cars flew by at 55+ mph. So I kinda looked around a bit on the ride up and took it all in.

When I pulled into the Skatepark of Tampa later that day kids couldn’t believe that I had ridden there from Naples. It just made no sense to one kid, who wanted to know why I just didn’t take a bus. Good question, really.

After peddalling a good 50 miles, I had just about the best skate session anyone could ask for. The Skatepark of Tampa has by far the coolest scene of people who hang out and skate. Every day it’s going off, and no one is really into that whole “gotta go pro” scene. Just fun.

I was exhausted by 9:00, though, and I got on my bike and made the last 10 miles to my friend Billy’s house in the dark. Then slept.

I ended up staying a week in Tampa. Everyone was so nice and hospitable that I just couldn’t leave right away.

On the day before I left, though, there was a best trick competition for two plane tickets to Barcelona at the Skatepark. I didn’t really think I had a chance against the SPOT locals, but I gave it a shot anyways.

I came out and tried a 360 shuv-it and would have landed it first try. But someone had fallen just below the stairs and I couldn’t stay on. Boneless frontside fingerflip over a stair set was the first trick I landed. Not bad. It got me into the round to do the big gap to bank…

Where I proceded to fall apart. I had landed a bluntslide to fakie earlier that day on it, and figured I could pull it again. No such luck. Oh well, guess I won’t be flying to Barcelona anytime soon.

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