Interview With the Freestyler


Mike Osterman is a professional, freestyle skateboarder. He’s also a recent college graduate with a degree in biology who has now entered the work force. He maintains strong friendships and, in general, uses his time wisely. Given his popularity and respect within the freestyle skateboard community, Mike was due for a little explaining about himself, which brings him here.

In going over some background with him for this interview, I tried to get a more accurate picture of his status in the freestyle skateboard world. He casually mentioned to me winning last year’s World Cup. I had to remind him that he was voted runner up for best freestyler of 2014 . He had forgotten and didn’t remember who won. Mike did, however, recall encouraging others who wanted to vote for him to instead vote for the eventual winner.

He views what he does through a modest lens that is incompatible with the competitive ego often associated with excelling at one’s sport. He’s never lost the sense of fun that skating is meant to be about, and isn’t the type of skater to get pissed off over missing tricks. That’s just the kind of guy Mike is. He keeps things in perspective, and, in doing so, reminds me of how it is the simple things in life that make it work.



September 25/26, 2015
Mike Osterman Interview



Nominay: When did you start skating, and why?

Mike: I started skating regularly in the fall of 2005. I had received a skateboard 3 or 4 years before then, but that’s when I really got hooked. At the time, my friend Kenny and I were playing the Tony Hawk Under Ground video games a lot. One day I beat one of the games and decided to grab my board and skate for real.

I think I was drawn to skating because everything else seemed boring or overly competitive in comparison. I was an indoor kid for the longest time and skateboarding was something that all of my friends were suddenly discovering. We all found it at once and were equally terrible at it. There was never a sense of competition. It was all relaxed and fun.

N: How did you first learn about Rodney Mullen?

M: I always played as him in the Tony Hawk Pro Skater games because he started his run with a rail flip. I associated the name with “weird tricks”.

That same friend from the last question, Kenny, had Mullen’s autobiography and lent it to me when he was done reading it. That was my first exposure to him as an actual person. Reading the book also introduced me to freestyle. It put a label on the weird tricks that I liked doing and gave me a keyword to search on Youtube and Google.

N: I first noticed you on youtube in the pre-facebook days. How important was yt for you in terms of skating back then?

M: Youtube was HUGE before the Facebook days. I think most of the guys in my generation used YouTube to figure out what freestyle really was. There was (and still is) so much footage from 1980’s contests on there. That was the starting point for me when it came to learning tricks and emulating people’s styles.

There were forums and random other web pages that existed back then which also played a HUGE role in developing the freestyle community. Bob Loftin had a trick tips page that contained step-by-step instructions for every trick that I wanted to learn. The WFSA forum and F!forum were good places to read about new freestyle products and talk shit to other ex-indoor kids. Witter Cheng had “the crypt” which was the largest online collection of freestyle skateboards that I’d ever seen.

I could go on and on about the 2005-2010 era.

N: Who were your influences in skating then? What experiences inspired you?

M: Back then I watched a ton of Tommy Harward’s footage. There was a site where he hosted a ton of his clips. tonybailey.com … not sure if that still exists.

The Casper Video was a big deal. Tommy, Terry Synnott, and Darryl Grogan had phenomenal parts in that video and they were major influences on my style. Also Masahiro and Toshiaki Fujii. As for “old school” guys, I was obviously into Rodney. As time went on I started watching Kevin Harris and Don Brown a lot too. Those two just looked more casual on their boards. I’d love to watch Rodney skate in person but I think I’d be more stoked to session WITH Kevin and Don.

Going to Tommy’s park in 2008 was a really big deal to me. I was there for the U.S. championships and met Gunter, Tommy, Connor, Sean, and Jeremy Elder for the first time. I got to see how small the community was and how important those DIY events were to maintaining a scene.

Speaking of DIY, Jeremy Elder’s brand — the small school cooperation — had a HUGE influence on my skating and attitude back then. These stories go on and on.

N: Who comes to mind as your peers in freestyle right now, and what can you say about their skating?

M: Ohhhh man, I’m gonna forget someone…

Connor Burke is amazing. He’s always had a really smooth, streetish style to his skating. He skates fast and he seems to flip his 8.25″ deck with more ease than most people flip their 7.25″ freestyle twigs.

Jesse Whalen trips me out. He skates an 8.5″ as well and has this neat bouncy style when he skates. I feel like he’s always developing in a new direction and it’s always so exciting to hear the new trick ideas that he’s coming up with.

Sean Burke is a brute on his board. He has an uber technical approach to skating and focuses a lot on truck transfers. I’ll get a text from him describing a new idea for a pogo trick and then 30 minutes later I’ll see a video of the exact trick. Sean gets it done.

Two other guys are Pete Betti and Derek Elliot. Those two are annoyingly good.

N: Have you ever had an interest in skating street or vert?

M: I get the itch to skate street almost every summer. I’ll set up a board, go skate a curb for 20 minutes, and then head back to the tennis courts. I’m not very good and it takes too much patience for me to get in line, wait, skate an obstacle, get back in line, wait, etc.

There isn’t much vert around me either. Some parks in my state have transition or maybe a bowl with some vert, but even that’s rare.

N: While attending college full time you also skated full time. Now, while working full time you still skate full time. How do you prioritize skating with the type of schedule you maintain?

M: Haha I probably sacrifice my social life to some degree to do that.

N: Tell us a little about staying with Kevin Harris for a month. For those still reading who don’t know much about skateboarding, Kevin Harris is one of our top, all time, freestyle legends.

M: Yeah! Kevin’s the man. He and Audrey were really nice to let me stay at their place. I helped out around the house wherever I could, weeded a little, etc. Rene Shigetto and I actually built a horse stable while we were there too. That was fun.

BC is awesome. People are friendly, there’s so much to do out in nature, and there’s really good Asian food everywhere. Plus, they have coffee crisp! It’s this coffee flavored wafer bar that I ate every day for a month. Audrey was nice enough to send me home with a Costco box full of them. 😀

Should I go on? haha

N: What are your future plans?

M: I’m gonna try to visit more freestyle events, film more, get tattoos, try to be an adult. What are adults supposed to do? I’m still not sure. I’ve always wanted to skate in the Paderborn event. That’s my next big goal.