Caswell was super open in his interview with SkateMore, and discusses facing down vertigo, the IRS, and dildo attacks from Ed Templeton. That and what it was like being in the middle of a tornado.

Caswell has been around for so long, that we sometimes forget how good he is. Then you throw on one of his video parts and get excellent trick selection and all-terrain skillz so good we have to spell "skills" with a "z." Since his first coverage (skating a halfpipe no less) in the late 90s to today, Caswell has been steady shredding.

How old were you when you started skateboarding, and how did you start?

I started skating back in the old days!!! Hahahah. I started roughly when I was 8 years old in 1990 or '91. A few years before that I got a Nash style board that had a "T" bar set of handlebars that connected to the top side, where the front truck was bolted in and it had a ninja for a graphic. I didn't like the handlebars, so those were the first things to go. A couple of friends had gotten the same board and after seeing that I had my mom take off the handlebars. Not too long after that, my board got stolen and that sealed the deal. I didn't end up skating for a few years after that until my mom met a guy named "Red", who would eventually end up becoming my step-dad for some years. He got me a Santa Cruz dot and cut it down to the size of a freestyle board, made a launch ramp, and had a few N.S.A. bowl and freestyle contest and Bones Brigade videos. The rest is history!

You rode for Powell the same time as Danny Wainwright and Javier Sarmiento. As an international team with riders all over the globe, was there much camaraderie?

When I rode for Powell there were two different sects, there was Powell and then there was Bones Brigade. Trips usually were with Powell and whoever rode for them during that time. I traveled a bunch with Rodney Jones, Silas Baxter Neil, Tony Manfre, Ryan Chadwick, Ryan Smith, Paul Macnau and some others. I did actually go on two Bones Brigade trips though. One was with Jon Comer to Venezuela and the other was to Japan with Javier Sarmiento and Danny Wainright. Before that, I had never met those dudes, although I am glad to have. So most of the camaraderie was with the Powell dudes.

And from Powell you went to Toy Machine- any good Templeton stories from those days?

Ed Templeton stories??? Well, maybe a few anecdotes.... He really liked shooting photos of me smoking cigarettes. Which by the way, he was one the few people that I was proud to share that I quit smoking with. One time he was showing me his garage/art studio and there was a piece that he had been working on in which Deanna (his wife) was naked. Just as I was admiring the piece, she walked in to do some laundry or something and caught me staring at it. She didn't even bat an eye!!!

Going on tour with him was always a treat. He introduced me to making travel journals, which I still keep up.

On a cross country U.S. tour he purchased a dildo with a grip on it. It looked similar to a bicycle hand grip. He would wield it like a sword and use it to beat the team in the van and people at the signings and demos.

Ed & Deanna Templeton

"One time he was showing me his garage/art studio and there was a piece that he had been working on in which Deanna was naked. Just as I was admiring the piece, she walked in to do some laundry or something and caught me staring at it."

How do you stay productive now that you no longer drink 6-8 Redbulls a day?

My life without 6-8 Redbulls a day is probably better. I got to the point where I could drink one at bedtime and not be affected. These days if I am feeling slow I will get a coffee. During my recovery from vertigo I had cut out all caffeine which included Redbull and started to drink caffeine free Coca-Cola. Once I was better I got into drinking those Starbucks double shots in a can. I eventually got up to drinking 4 of those a day; two in the morning and two in the afternoon. Those things are strong and made my anxiety ramp up like crazy, so I had to chill out on those. That's when I downgraded to regular old coffee. I obviously have a problem with regulating my consumption of certain things. Lately I've been drinking coffee from time to time and Coca-Cola on a regular basis, and that is what keeps me going.

You own a home in San Jose. Now that you have gone through the process, would you recommend home ownership?

Yeah, I own a home in San Jose and it's a dream come true!!! I never thought I would own a home!! Would I recommend home ownership? Hell yeah!! There are things that suck about it, but that is just like everything else. It has its ups and downs. I wouldn't recommend it to the terribly lazy folk though. There is always something that can be done around the house. Don't get me confused though, I can be pretty lazy with certain things. One thing I like to do is get out and do yard work though. Recently, I have been dealing with dying grass. I think I might have over-fertilized it. Everything is a learning process with owning a house. I just really wish I had real construction skills. There are tons of things I would love to do with my pad, but don't have the know-how to do. I would hate to ruin my house and make a wall fall down or something, you know? I almost blew myself up changing a water heater, but that is another story!

You have also mentioned having some difficulties with the IRS in the past. Any lessons learned coming out of that?

Yeah, one thing I have learned is pay your fucking taxes!!! You cannot be lazy about it and think that it will sort itself out eventually. You HAVE to go out of your way to pay the IRS or they will swoop in with the hand of doom. They will make your life harder than it needs to be by placing levies on your bank account, rendering your account bone dry. I've learned my lesson and I’m a good boy, paying my taxes on a quarterly basis.

What’s your favorite skate spot within 1 mile of your house?

My favorite spot within a mile of my house is the red curbs at the hospital. Freshly painted curbs frontside and backside. You can't really session them though. It's kinda like a one hit wonder. You can cruise through and slappy a few and continue on your way. If I want to actually work up a sweat or try and work on a trick, I'll go to the city college and shred the cement benches. I just recently Salba Sauced them up. There is a few in a row and a nice manual pad which is slightly downhill.

Front Blunt Kickflip Transfer | Wesley Tonascia Photo

"I am the type of dude that puts unneeded pressure on myself. So, in this day and age of media over-saturation the pressure is even worse!"

As an established vet in an era of media saturation, do you feel more or less pressure now than you used to?

I am the type of dude that puts unneeded pressure on myself. So, in this day and age of media over-saturation the pressure is even worse! I am trying to learn it is what it is and to just film absolutely everything. It's almost like you need to install a web cam in your house to film you while you cook dinner and take shits!!! I really miss the vhs and dvd days when you worked on projects as a whole team instead of a single person video that goes on the internet and gets lost in the shuffle.

Does the process of hucking yourself down gaps and rails change as you become a grown-ass man?

The process of jumping down gaps or onto rails has changed a little as I grow older, but I think the real game changer is an injury. That can really put a damper on jumping down things. Getting older also allowed me to start using my brain more often and realizing that there is more to skateboarding than just jumping down things as well. There are other ways to skate and actually have fun. Skating with a diverse group of individuals that all skate different things helped too. So, getting older doesn't necessarily affect carcass tossing unless you want it to.

Is there a trick from one of your previous video parts that stands out as being really hard to get?

I can't really recall a specific trick from a video offhand where I had to go back more than a few times to get it. I'm sure there were a few over the years. I can tell you that there is a spot that seems to be bad luck. There is this steep bank to wall ride here in San Jose. The first time i had gone there I tried a trick for an hour and walked away empty handed and the next day I came down with a bad case of vertigo. I didn't skate for about 6 months.

The second time I went there I was just messing around wall riding it and got caught on the way into the bank from the wall. I fell 5 or 6 feet straight to flat and knocked the wind out of myself. It was the kind of bail where you make unholy demon noises while trying to catch your breath!The last time I went there I once again didn't get my trick. I got close, but no cigar as they say. On my way out of the spot I got in a fender bender.

Click Watch Caswell's Part | 9th Annual TWS "Skate Video Of The Year"

"Getting older also allowed me to start using my brain more often and realizing there is more to skateboarding than just jumping down things... There are other ways to skate and actually have fun."

How’s your vertigo these days, and did that experience inspire you to be more health conscious?

The vertigo is crazy man. It's something that will always be with me. It's like the friend that I never wanted that follows me around where ever I go. Last year I had another bout with it. It was minor compared to the initial blow, but enough to cause me grief. It just makes me feel a bit off balance and feel a bit crazy. The vertigo has definitely made me more conscious about my health. I try to eat healthier when I can and take vitamins and supplements. I will visit an acupuncturist when needed, and a chiropractor on a regular basis. It's also helped me start to make decisions to better myself in other ways, like by quitting smoking.

As a successful pro, do you feel much pressure to give back to your family now?

Supporting the family has always been a big thing for me. It didn't just start when I became "successful" at skateboarding, but It's gotten easier. While looking at houses one of the mandatory things to have was house in the backyard that my mom could live in. I wouldn't call it pressure to help support the family. It's just normal to want to give back.

Most underrated Tiltmoder?

Every Tiltmoder is underrated at one thing or another. We are a group of talented sonsabitches. Some are good at construction. Others are good at woodworking or......drinking!!!!!!!!!!!

What’s the gnarliest Louie trick you've seen go down?

I've seen Louie do some really fucked up things over the years. He has done some gnarly frontside krooked grinds to fakie and 180 fakie 5-0's on some ridiculous tranny. I still want to say one of the most retarded things he's done is the hand manual that was in the Man Down video. I didn't see that go down in person, but that doesn't change a damn thing. He is a magician on a board!

Click To Watch Louie's Bonus Footage

"I still want to say one of the most retarded things he's done is the hand manual that was in the Man Down video. I didn't see that go down in person, but that doesn't change a damn thing. He is a magician on a board!"

Favorite Osiris shoe?

My favorite Osiris shoe is obviously gonna be my own!!!! I really liked my first shoe. Before you pass judgement and laugh at me let me give you a reason- Any shoe that I actually spent time on and helped design is obviously going to my choice for my favorite shoe.

Caswell's Favorite Shoe- His Own!

What happens in a typical Enjoi meeting?

A typical enjoi meeting usually involves pizza and some beer. Possibly a ramp session depending on where we are at. Just a bunch of grown ups acting like children discussing some important things and lots of pointless crap that will make you laugh!!!

With Matt Evs no longer at Enjoi, do you think it will be a challenge to preserve the character of the company?

With Evs not in the picture anymore things will be different, but I don't think it will be hard to help preserve the character though. If you can recall, enjoi went through something similar when MJ (Marc Johnson) left to go to Chocolate. At that time Evs stepped up and took over the brand manager role. As long as you can trust the person who steps into that role and who can listen to what the team has to say than you're good.

You have seen a lot of the world. What’s the sketchiest thing you’ve seen while traveling?

My brain is broken right now and I don't feel like scouring through my travel journals, so I will just say what is coming to my mind right now. When I was a kid my family would go to Minnesota in the summer time for a month or so and stay at a resort on a lake. One year we stayed in a small camper and there was a bad storm. I remember waking up to the loudest thunder and brightest lightning I have ever experienced. I tried to fall back asleep, but no luck. Out of nowhere the camper seemed like it got hit with by a wave. All i could see was gray swirls and it seemed like i was sticking my head out of a window of a moving car. My mom and step dad were holding on to my sisters arm while she was flapping in the wind like a sheet. I got hit with a tv in my back. Before I knew it, the whole thing was over. It was a damn tornado!!! In the morning we were checking out all of the damage. There was a tree that had fallen that was just a few feet from smashing the camper, an anchor from a boat stuck in a cabin wall, and the gnarliest thing was a speedboat stuck up in a tree!!!!

We figure there's no way to possibly top that story, so that's it. Thanks Caswell!