I made my first skateboard when I was probably in 6th grade. I cut the wheels from my sister's old roller skates off and mounted them on a piece of plywood that I cut into a rough skateboard shape. I painted it black and bright yellow and it was bad-ass.
Later I got a "real" skateboard at K-Mart and it kinda sucked cuz the wheels were hard rubber. Then another one that actually rode like a skateboard and I had that one for a few years.
When I was 23, I rode a REAL skateboard across Hoover Dam, back and forth for a total of 50 miles for a radio stunt.
I still longboard occasionally but not often cuz falling off at my age doesn't appeal to me at all.
About 3 years ago I got a powered skateboard and I love it. I hadn't ridden it all summer because you know how time gets away. But I took it out Sunday and loved it.
They're not cheap but they're awesome. And no, I'm not getting paid or given free stuff for mentioning them. Here's their website.
And a video.