Why did you choose freestyle?
I grew up in the middle of the country, about an hour outside of Chicago, and didn’t have easy access to any parks or decent skate spots. I also played a lot of Tony Hawk’s Pro Skater, so I was exposed to freestyle tricks that way. I think the combination of no parks and exposure to freestyle tricks led me to learn that stuff. Then I read Rodney’s book and discovered that it all had a name, competitions, forums, etc. Luckily the forums and grainy online videos in 2006 didn’t scare me away.
Did you ever do any transition or street skating?
I did a tiny bit of street skating. Mostly curbs and manual pads. I’m terrible at that stuff.
Same with transitions. I used to work at Jeric’s Skate Shop in Plainfield, Illinois. They had a two-foot mini ramp in the shop and I could barely ride it, despite spending most of my time there, haha.
How long have you been skating for?
I started skating in 2005 so I guess that makes twenty years now. And now I feel very old.
How much time does running Waltz Skateboarding leave you to skate for yourself?
Zero time units. Seriously though, I try to have at least one session per week. We meet with the Long Beach freestyle crew every Sunday so that keeps me on my board. I’m grateful for that. I’ll sneak off for a lunchbreak session now and then as well. That’s always nice.
When did you start Waltz?
Daniel Trujillo and I officially started Waltz in April of 2018. We made a few t-shirts before that, but 2018 is when we made the leap and made it legit.
What inspires you to keep Waltz running?
Jamie Wong makes me keep it all running. The goal of Waltz has been to grow the community and make decent gear for them. A lot of people really love being part of a freestyle scene—online or in their towns. That’s been a huge motivator. The US Open was a really emotional experience for that reason—seeing so many people come together to support our local scene and each other was surreal. I just want to do more of that.
What’s the hardest part of your job of running a freestyle company?
I think the hardest part of running Waltz right now is finding a way to make all of the things that we want to. Freestyle gear is hard to make. Period. Most factories, especially those in the USA, have dialled in their processes to churn out standard skateboard shapes (both wheels and decks) SUPER efficiently. That’s how they stay competitive. I’m SUPER grateful to work with a handful of smaller factories that are down to get weird—pressing with custom moulds, accepting relatively low order minimums, developing custom wheel moulds, etc.
Still, with the broad range of sizes and shapes that folks ride, it’s extremely difficult to make a board to serve every person’s preferences. There’s always that one guy who wants a 7.51255″ instead of a 7.4″ or a 7.75″. And the wheelbase is never right. Still, I do my best to stock a couple shapes in each of our concave families. Making the ‘best freestyle board’ means serving a wide range of freestylers.
That same challenge applies to every other part of Waltz’s work. Media, events, even our community forums like our Discord. Waltz can’t make everything. We can’t be everything for everyone, so I spend a lot of time trying to temper my enthusiasm. 😀 Someone else can make the Freestyle Brazil Tour Video.
What do you have planned for Waltz in the future?
Ugh, hopefully more nap time. Two new pro models dropping in 2026 if we can get our act together. 😄 More trick tips. We’re discontinuing Waltz Wheels (cue sad music) and maybe a new collab with an old friend? Is that cryptic enough?
What does Mike Osterman do when he’s not skating and making boards?
I’m pretty boring. I love going on walks around Long Beach. Maria and I spent a lot of time in Japan just walking. When I’m injured, I usually end up playing a lot of video games—playing a lot of UFO 50 lately.
Connect: Mike Osterman is the co-founder of Waltz Skateboarding, organiser of the US Open of Freestyle Skateboarding, and captain of the Long Beach freestyle crew (Instagram: @lbcfreestyle). Basically he wears many hats, which is why his pro board has a bunch of hats on it. Follow him on Instagram (@mike_osterman) and YouTube (@mike_osterman1). If you want a Mike Osterman board and or other Waltz Skateboarding models, you’ll find them stocked at Aikenheads (Perth, WA).