Next up in our 21 Questions editorial series, we’re hanging out with Lucy Osinski, the CEO powerhouse behind GRLSWIRL. If you’re into skating, surfing, or just building rad communities, you’ve probably heard of her women-founded skate collective that inspires people of all backgrounds to show up as they are and be part of an empowering and supportive community. We caught up with Osinski to talk about her journey as a surfer, skater, and founder, and to find out what’s keeping her stoked these days.
Surfing wasn’t Lucy Osinski’s first love. Surprisingly, as the co-founder of one of the biggest women-founded skate collectives in the world, neither was skateboarding. What’s always fueled Osinski, above all else, is community. Skating—and later, surfing—became the vehicles for that sense of connection, confidence, and pure joy that being a part of a community can add to your life.
Before launching GRLSWIRL in early 2018, Osinski, born and raised in Upstate New York, was about a year into her new life on the West Coast. She’d just swapped life as an organic farmer in France for a career in film production in Venice, California—and before that as a professional ballerina. Living in the birthplace of modern skateboarding, she decided to give skating a shot, and it changed everything.
“Skating always fascinated me,” she says, “but I never really saw women or non-traditional skaters represented in that space. The culture felt intimidating—so many people wanted to try, but there was this fear of judgment, of not being ‘good enough.” That realization led her to co-found GRLSWIRL alongside eight other women who had made her learning journey in this male-dominated sport so much less intimidating.
Picking up skating the way she did—alongside that supportive crew of women—showed her how freeing it is to be okay with just being okay at something. That mindset became GRLSWIRL’s unofficial motto and the heartbeat of everything the community stands for today. As Osinski reiterates, “there’s joy in just showing up and doing it for the love of it.”
That ethos has sparked a massive women-led skate movement that’s transcending barriers and bringing more women to the sport on a daily basis. Today, GRLSWIRL is a global community with eight thriving chapters around the world and an online community of hundreds of thousands of skaters who consistently hype each other up, meet for group skates, and give back to their communities through GRLSWIRL’s social initiatives, including reforestation projects, skate mentorships with local youth, and ocean conservation initiatives.
When we asked Osinski what the surf world could learn from her community, she said: “I’d love to see more softness, more encouragement, and more willingness to teach in the surf community. In skating—especially in GRLSWIRL—we celebrate every small win. We hype each other up for just trying. Surfing can sometimes feel more exclusive, more competitive—like you have to prove yourself to be worthy of a wave. I want to see more of that GRLSWIRL energy in the water. It’s not just about the skating [or surfing for that matter]—it’s about building friendships, finding confidence, and breaking down the barriers that keep people from trying new things.”
1. Coffee or tea?
Coffee
2. What’s the first thing you do in the morning?
Play w my dogs
3. Favorite snack after a skate or surf session?
Burrito
4. Go-to skate trick that always makes you smile?
Bert slide
5. Three words your friends would use to describe you?
Golden retriever puppy
6. Surfing or skating: if you had to pick one for the rest of your life?
Skating
7. Favorite skate spot of all time?
The Cove in Santa Monica
8. Favorite surf spot of all time?
San O
9. Dream surf destination you’ve never been to?
Morocco
10. When did you first pick up a skateboard?
8 years ago
11. Where did you catch your first wave?
El Porto, CA
12. What’s your favorite surfboard setup right now?
5’8 Quad
13. Who’s a skater or surfer who’s been a big inspiration to you?
Mikey Feb
14. Where do you go when you need a boost of inspiration?
TIKTOK lol
15. Who’s someone in your life you look up to, and why?
My biz partner Kelsey. She is so patient with everyone around her—her kids, employees, friends, family. She’s just so calm and centered.
16. Favorite piece of gear or style staple that’s always with you?
OCA low CARIUMA sneakers. Always white
17. If you could collaborate with anyone on a GRLSWIRL project, who would it be?
Beyonce, obviously
18. What’s the best part about leading GRLSWIRL?
Having something I’d do if I were paid or not
19. One lesson you’ve learned from building your GRLSWIRL community?
Lead with authenticity and vulnerability
20. One lesson surfing has taught you that you bring to your skating and your life?
Knowing when to charge and when to sit back and flow
21. If GRLSWIRL were a song, what would it be?
“California” by Joni Mitchell
If you’re feeling inspired to skate, connect, or just follow along with Osinski and the GRLSWIRL community, follow @grlswirl and @lucyjean333 on Instagram. Head to grlswirl.com for news about upcoming events, more information about the online community GRLSWIRL ONLINE, and to shop boards and gear (which helps fund their social initiatives).
