OUR TEAM
Inspiring the Next Generation of Skaters
WILL STEPHAN
Q: How long have you been skating?
A: I have been skating for 17 years.
Where is your favorite place to skate in the city? Park and street spot.
A: My favorite skatepark in the city is Wilson Skatepark in Uptown. It is filled with great features and has two really fun bowls! My favorite place to street skate is at a DIY barrier spot in Pilsen.
Q: What's on your go-to skate session soundtrack?
A: It really depends on the mood of the session, but you can never go wrong with Lynyrd Skynyrd or Waylon Jennings.
Will is the Owner and Program Director of Chicago Skate School, as well as the founder of Sapient Skateboards, a Chicago-based brand and independent skateboard manufacturer. With over 15 years of experience across multiple facets of the industry, Will is a fierce proponent of all things skateboarding and the many invaluable life lessons it provides.
Q: What has skateboarding taught you?
A: Skateboarding has taught me to find joy within the learning process, no matter how difficult it may be. If you remain patient with yourself and learn to love the process, you can accomplish whatever it is you set your mind to.
Q: What advice would you give to someone just starting out?
A: Focus on the fundamentals. Every bit of progression in skating stems from your ability to feel comfortable on your board. Take your time, always get back up, celebrate the small wins, and have some fun with it!
ZACK RUPP
Zack has been skating for 20+ years, sometimes for tricks and other times to just get around town. He previously taught special education at a Noble Charter School for five years, where he led a skateboard program for 3 of those years. He currently substitutes for CPS and is earning his endorsement in physical education.
Q: How long have you been skating?
A: Since I was about 5 years old. I remember scraping my knees on an old penny board!
Where is your favorite place to skate in the city? Park and street spot.
A: I'm biased, but I would say my favorite park is Marshfield Courts & my favorite street spot is at 31st St Beach Pier. Fun ledges to grind and cubes to wallie. Tired? Go for a dip!
Q: What's on your go-to skate session soundtrack?
A: No particular track - just vibes. 70's punk, 80's new wave, 90's hip-hop. 2000's dad rock. Just depends on the session
Q: What has skateboarding taught you?
A: Skateboarding is so much more than pushing around a wooden toy. It builds relationships, creates challenges to overcome, and uncovers new passions.
Q: What advice would you give to someone just starting out?
A: Take your time & HAVE FUN! Skateboarding is difficult no matter how much experience you have, but enjoying the process can be just as rewarding as the result.
BELLA GARCIA
Hey y'all, my name is Bella! I have been skateboarding for 5 years. I started skating in 2020 during the pandemic. I first became a skate instructor in 2023 and have been gladly teaching ever since! I love teaching because it pushes me to think outside the box and come up with creative obstacles and courses that help kids grow their skills and build confidence.
Q: How long have you been skating?
A: I’ve been skateboarding for 5 years now.
Where is your favorite place to skate in the city? Park and street spot.
A: My favorite spot to skate is Laramie Skatepark in Cicero, that’s actually where I first learned how to skateboard!
Q: What's on your go-to skate session soundtrack?
A: Lately, my go-to skate soundtrack is a mix of Midwest emo, alternative indie, and anything upbeat that keeps the energy high.
Q: What has skateboarding taught you?
A: Skateboarding has taught me a lot, especially patience. It’s shown me that anything is possible if you’re willing to put in the work and keep showing up.
Q: What advice would you give to someone just starting out?
A: If you’re just getting started, my biggest piece of advice is this: skateboarding is all about consistency and repetition. The more you practice and stick with it, the more fun and the easier it gets!
HARRY MASTER
Heyyyooo, I'm Harry! I've been on a skateboard for over 20 years, growing up in skateparks and loving all things transition. I've spent time skating at legendary spots like Camp Woodward and exploring the best parks in Michigan and Southern California. My background as a graphic designer fuels my creativity on and off the board, and I love practicing all kinds of quirky tricks. I'm stoked to help you find your footing and have a blast on your board!
Q: How long have you been skating?
A: 20 years
Where is your favorite place to skate in the city? Park and street spot.
A: I like Evanston Skate Park for the park vibes, and hit up Clemente for DIY street spots.
Q: What's on your go-to skate session soundtrack?
A: I like all things Funk & Soul Hop
Q: What has skateboarding taught you?
A: Skateboarding's taught me resilience, the art of creative problem-solving, and the amazing feeling of community.
Q: What advice would you give to someone just starting out?
A: My advice? Embrace the falls, have fun, and be patient. Find your crew, wear your helmet, and just keep pushing.
Satomi Rabottini
Hi everyone! My name is Satomi, and I've been skating for 4 years. I have been teaching for over 10 years, in language, dance, and now skating. Skating has shown me patience, discipline, and that no one size fits all - the way we learn tricks evolves with us as individuals. I'm passionate about helping new skaters find a process in skateboarding that they can trust and love!
Q: How long have you been skating?
A: 4 years
Where is your favorite place to skate in the city? Park and street spot.
A: My favorite park is LV2 (La Villita Park), my favorite DIY is Marshfield Courts, and my favorite street spot is the Wilson curbs. (RIP)
Q: What's on your go-to skate session soundtrack?
A: A good classical music setlist always gets me in the right mindset. Recently, it's been The Planets, Op. 32 by composer Gustav Holst.
Q: What has skateboarding taught you?
A: Skateboarding has taught me the value of pursuing something for yourself. We often overlook the importance of dedicating time for you and only you, somewhere you can battle your thoughts and take a moment away from the pressures and difficulties of life. The reward can be a new trick, or even just the fact that you were able to clear your mind through movement and expression. Skateboarding indiscriminately provides everyone a space to be themselves and better themselves.
Q: What advice would you give to someone just starting out?
A: Entering the skatepark or trying to skate a spot on the street that you found can be such an intimidating task for the first time. The local park skaters may notice you're the new kid, and the occasional "do a kickflip" yell as a few pedestrians watch you skate can really set off your nerves. That's when it's important to remember that this is also, in a sense, a part of skateboarding. Everyone started somewhere as the new kid, even the best of the pro skaters, and it's important to remember that everyone (regardless of race, ethnicity, gender, social class, age) deserves to take up space, as long as you're respectful to the spot and the other skaters. You'll also be pleasantly surprised at how many people are happy to help beginner skaters find their feet!
Caden Slovacek
Yo, I’m Caden! I’m an engineer, artist, and a passionate skateboarder above all else. Skating has shaped who I am over the past decade, and I’m always stoked to share the lessons, creativity, and community it’s given me with the next generation of shredders. I strive to create a fun, supportive environment where kids can grow both on and off the board.
Q: How long have you been skating?
A: I have been skating for 12 years.
Where is your favorite place to skate in the city? Park and street spot.
A: My favorite park is Wilson and my favorite street spot is the UIC Student Center East Alley.
Q: What's on your go-to skate session soundtrack?
A: Canned Heat – Going up the Country
Q: What has skateboarding taught you?
A: Skateboarding has given me a determined mindset, teaching me the importance of patience and persistence in all my endeavors. It is an extremely difficult skill to develop, which has inspired me with confidence that I can accomplish anything I set my mind to.
Q: What advice would you give to someone just starting out?
A: Try to skate every day, even if you are not practicing any tricks. The more natural it feels to ride the skateboard, the easier everything else will come.