Who Gets to Decide?

A handful of years ago, I was sitting in a meeting at the skateboard company I worked for when someone showed me a DM. It was from a 13-year-old girl. And a few days earlier, she had just won the first ever Olympic gold medal in women's street skateboarding. And I don't know what you were doing at 13. I was certainly not winning Olympic gold medals. She had written to us in English that had clearly been translated. To say that it was her dream to ride for one of our brands. Her favorite brand. For about a minute, the room was genuinely excited.

Flattered, even.

And then, almost as quickly as that excitement happened, the conversation changed. There were concerns that she was too young, that she might not even be interested in skateboarding in a few years.

Which, sure, maybe it's a phase.

Maybe winning an Olympic gold medal at 13 was just something she was trying out. And to be fair, I should give you a little context here.

This was the very first Olympics for skateboarding.

And the thing is, skateboarding itself wasn't entirely sure how it felt about being there. And you guys remember, right? Skateboarding is not a crime. To all of a sudden wearing a uniform representing your country. It was a strange adjustment. And there were legitimate questions.

What does Olympic success actually mean in skateboarding? Do we care?

And just because you won a big contest, that's never automatically meant you're the right fit for a brand. That's not really how skateboarding works. It's all about the relationships, your personality, your style, the identity of a brand. It's a whole collection of things that don't simply equate to, cool, you won, welcome to the team. I understand all of that.

I spent years working inside that system. But what stayed with me about that meeting wasn't really the decision. It was how quickly the possibility seemed to be dismissed, how certain people were about what she might or might not become. And for all the time we spent in those meetings talking about the future of skateboarding, I feel like a lot of the times The rooms seem pretty committed to the past. And look, I understand the attachment. I, too, have a deeply unreasonable emotional connection to certain eras of skateboarding.

The ones that defined me. The videos, the skaters, the music. And recently, of all the people. the Canadian Prime Minister, Mark Carney, gave me a pretty good way of putting my finger on the problem. He was speaking at the World Economic Forum in Davos.

Not my usual source of skateboarding industry guidance.

He was talking about international geopolitics, suggesting that the world had changed and perhaps America might want to consider moving into that future. Basically, he was telling us off in the most politely Canadian way possible. And he said something that stuck with me.

We know the.

Old order is not coming back.

We shouldn't mourn it.

Nostalgia is not a strategy.

I realize international geopolitics and the skateboard industry aren't exactly equivalent. Although both worlds have managed to keep many of the same men in power for years and years. So you can take that as an interesting coincidence. Anyways, nostalgia is not a strategy. I've been turning that sentence over and over in my head because skateboarding is having some really difficult conversations right now. About declining sales, shops closing, an aging customer base and where the next generation is going to come from. And yet so much of the industry's imagination remains devoted to recreating the world it remembers.

The good old days. Thing is, nostalgia has a.

Way of turning our personal experiences into a one-size-fits-all standard. We remember how something made us feel. And eventually, we start believing that's how it should make everyone feel. The past is a wonderful place to visit. It just becomes way more complicated when we insist that everyone else live there.

And that meeting about that rider, it wasn't that unusual. I'd sat through plenty of conversations like that. I'd forward a skateboarder's Instagram over, and then the assessment would happen. It was always some variation of, they're just a contest skater. Not enough viable street footage. Too much park footage. Nobody wants to see this. Not really the right fit. Some objections considerably less flattering that I won't repeat here. And just like that, the possibility of that person would disappear.

I remember another skater, different meeting, same outcome. She was already a dominant force on the contest scene. She wasn't asking for money, she was willing to ride the wheels for free.

Still, a pass.

And after years of working inside this system, I'd developed my own kind of tactics. It was always the obvious ones. Make it their idea. Let them connect the dots. Sometimes I'd have to relentlessly bring up the riders during any opening. I'd set internal mandates for support within the brands. For every three ads, one would feature a woman or gender expansive skateboarder. Or I'd build a marketing run on the back end. pick up the phone and connect with anyone who could link one opportunity to the next so that rider was suddenly showing up everywhere in the right places.

A carefully orchestrated coincidence. But on a silver platter.

Hoping that someone would recognize the hype and see the potential. Or at the very least just get curious.

Enough to pay attention.

And my other favorite was when someone internally would come back from a trip where that same skater had been, who didn't have all the right footage, and suddenly, they were so cool.

Such a vibe.

The only thing that had changed was that they had actually met. And they weren't just a name on a screen anymore. And again, I'm not suggesting every brand needs to sponsor every talented skateboarder. But what interests me isn't that someone made the wrong call. Or that these are terrible people. That's not the case here. In business, people make the wrong calls all the time. It's the framework that made those calls seem so obvious. Silently declaring what's valuable and what isn't. There's a type in this industry who's always protecting the brand. And sometimes what they're really protecting is their own idea of what the brand is supposed to be. And because you have to remember, for years, women and gender expansive skateboarders have had very limited access

to the traditional pathways into professional skateboarding. And I realize saying traditional pathways into professional skateboarding is such a weird sentence. Especially for a place that's famously known for not being big on rules. Somewhere along the lines, we developed an impressive number of them. And the undercurrent rules, I feel like they were pretty easy to rewrite. Someone would come along who didn't quite meet the criteria, but everyone liked them.

Suddenly, the gate opened right up. Funny how that can work.

So a lot of these skaters found other ways in. Contests were one of the few places that you could just enter in on your own. And you were able to skate and make some money to pay for the rest of the job of being a skateboarder. And you'd build an audience along the way. Haisa Leal built an audience of 8.2 million people following along and fanning out to see what she would do next. For comparison, Thrasher Magazine, skateboarding's official bible, only has 6.4 million followers.

As the collective voice of skateboarding.

So it's a pretty remarkable thing to give someone very little access to your world and then question their legitimacy when they find another way in. And another layer to all of this, we give so much authority to lived experience in skateboarding. Often the pipeline goes, you're a former pro and then you moved into a brand. You understand the culture from the inside. You helped create it. You know all the people, the language. You can get anyone on the phone when you need to. It's all the subtleties that don't translate into the business world.

That is valuable. I know this.

That's how I got here too. But lived experience is also, by definition, limited. You could spend forever in skateboarding and still have a very little understanding of what it's like to be a 13-year-old girl navigating skateboarding today. Having a daughter doesn't automatically mean you understand women's skateboarding.

But congratulations on the daughter, though.

The problem isn't that you don't understand. The problem is when you assume you do. And lately, I've been thinking about all of those conversations again. Because have you been watching what's happening in the WNBA?

It's unreal.

And I think skateboarding might want to take a few notes. All right, everyone, we'll be right back. And I promise this basketball detour has something to tell us about the future of skateboarding.

Good Luck With That is an iHeartWomen sports production in partnership with Deep Blue Sports and Entertainment.

Hey, everyone.

I'm Ashley Rayfeld, and this is Good Luck With That. If you've been listening to the past episodes, you know I ride for my she's, gays, and they's with the Valkyries. I'm a skateboarder first, but I love women's sports. I love watching people who are extraordinarily good at doing something that I could never do. And we're finally getting to know these athletes as people, not just what happens during the game. We get to see the personalities, the behind the scenes, and the media coverage has been hitting so hard, largely in part because of who's telling those stories. And then there's all those little bonus things that are really fun to follow too. The wags who sit courtside, the increasingly elaborate L word chart of who's dated who. All

of this is an essential component to any serious sports analysis.

Obviously. And skaters, stay with me here.

Because the more you learn about the people playing a sport, the more you start to understand the world around it. The labor struggles, the women's movement, civil rights, LGBTQ plus history, all because someone was exceptionally good at putting a ball through a hoop. Which when you think about it, is pretty much how skateboarding has always worked. First, you see the part. Then you want to dress like them. Then you find out about the band that made the song in the video. Then you want to visit the spots.

And suddenly you're standing in front of a granite ledge in another city and you're genuinely moved.

And before you know it, you're learning.

About the architect who designed it, the materials that were used in that plaza. You came for the skate spot and you left with so much more. It's one of the many great pleasures of skateboarding. The activity is just the beginning. And lately, I found myself going down a very similar rabbit hole with women's basketball.

A sport that I've never actually played. Unless you count horse. Or knockout. I want to give you two numbers. And don't worry, it's not a math equation. $ 1. 3 million.

And then $ 1. 9 million. They're not terribly far apart. Until you find out what they represent.

$ 1. 3 million is.

What the entire Golden State Valkyries team made in 2025. All of their salaries combined. The second number, $ 1. 9 million, is what one player named Quentin Post did who sat at the end of the bench for the Golden State Warriors made that same year. He hardly stepped on the court that season. So one guy made more than the entire women's team combined. With the same ownership. In the same building. This is such a crazy illustration of the problem that it almost feels made up. especially when you take all that has happened in such a short period of time. The Valkyries have sold out every regular.

Home season game.

They became the first women's sports franchise to bring in $ 100 million in annual revenue. All within two years, they're now estimated to be worth a billion dollars.

Billion with a B.

Which is a remarkable amount of money for something we've spent decades being told nobody wants to watch. Because wasn't that always the argument, right? Nobody cares about women's sports? It's such a wild conclusion to draw about something that you've made almost impossible to find. The broadcasts were always scattered across different platforms. One game was on one provider and then the next required a different subscription. And even then, I've been here, you might discover it was blacked out in your area and you're like, wait, I thought I paid for the right one for this game. And sometimes when you finally found the game, the production quality was so bad that it looked like someone had set up

a camera in the high stands and gone home for the night.

And then there was the media coverage. Minimal at best, and when you would find it, it would be so dismissive.

And when the audience numbers were disappointing, we used those numbers to explain why the sport didn't deserve more investment. You don't invest because nobody's watching. Nobody's watching because you don't invest. And around we go. And that's only half the story. We'll be right back after this quick ad break.

And if you think we've figured this out by now, I'd like to introduce you to the current state of the WNBA finals. The Golden State Valkyries are playing the Atlanta Dream, and this finals have been so incredibly fun to watch. The viewership has been at an all-time high, shattering new records. The games have been sold out at 18,000 paid tickets over and over again, And now Game 6, which could decide the championship, is scheduled for Thursday at 12.30 p.m. in the afternoon, or 9.30 a.m. for those on the West Coast, largely when most of the country is unavailable to watch sports. And I think about all those kids who are going to be at school who have been watching this entire season, and their favorite player

is Angel Reese or Gabby Williams, and they might not be able to experience a potential historic moment, Somebody could win a WNBA championship over your morning coffee. Skeptics have always pointed to the numbers. But this kind of scheduling decision is what manufactures terrible numbers and bad outcomes. And I'm pretty sure even if you're not a sports fan, you remember what happened when the Knicks won the championship.

New York completely erupted and went on hold for the night. Everyone got to the streets, celebrating with their neighbors. It was unbelievable. It was one of those things that was just bigger than sports, bringing people together for that historic moment. And here we are, making history for the WNBA during your workday. And here's a fun fact. The Hawks haven't made the NBA Finals since 1961, when they were still in St.

Louis. This isn't a scheduling issue. This could be worked out.

At a certain point, it just becomes embarrassingly obvious what's happening here. It's a fascinating business model. You have the supply. There's clearly the demand. People are practically begging to give you their money. I'm pretty sure capitalism loves this part of the story. And skateboarding, of course, has had its own rich history of exactly this. There's a market, just not many in charge could recognize and deem of any value.

So the money was just left sitting on the table, flashing under a neon sign that said more money here. And the thing is, for years, it wasn't just the fans who paid the price for this kind of thinking. The players did too. Some of the best basketball players in the world spent their off-seasons playing overseas. And when I say overseas, I'm not talking about a charming semester abroad.

I'm talking about months away from your families, your life effectively on hold. Sometimes, playing in countries where being openly gay could be dangerous, or where a government's record on war crimes and human rights wasn't exactly a selling point.

Oh, the irony.

Countries that don't value women's rights were paying these women more than our own country. That's just where the money was. Playing professionally at home often wasn't enough to make a living. So we called playing overseas an opportunity. And there's something so terribly strange about being one of the best people in the world at your profession and needing a second job to afford your first one. So the more I learned about these players and the league, the more I started to recognize a story that I already knew. because I had spent years watching a version of this unfold in skateboarding.

Remember that billion-dollar valuation?

What I find so interesting about that number is how much of the potential had simply gone unrecognized. The fans who hadn't found a way in, the kids who hadn't yet imagined themselves playing. None of that shows up on a balance sheet. Not at first. Because you can't really measure the value of an opportunity people haven't given you yet.

Someone has to create it. Ohema Nyanen, Millie Yee, Natalie Nakase were all put together by Jess Smith. Four visionary women who helped build a WNBA finals team from scratch in under two years.

And I just want to point out the obvious.

Not every skateboard company is sitting on a billion-dollar franchise it hasn't discovered yet. But you do have to wonder, what else are we overlooking? That's the conversation I opened up with. That 13-year-old girl who wrote to us, she did end up writing for the brand, eventually.

It just took time.

And a lot of dragging it back into the room, fighting for her and whoever came next. And the skater who couldn't get on the wheel brand, even for free, She's one of the more talked about skateboarders reaching fans far outside the traditional industry. And she's moving the bar of progression for women's skateboarding on what feels like a weekly basis.

It is wild to see if you've been watching.

I think about both of them and so many others when I hear people ask where skateboarding's next generation is going to come from.

Because they're already here. they've been here.

So how many more futures are we going to dismiss because they don't look enough like the past? All right, everyone, join us next episode.

Alex White is back on the mic with us.

Fresh from the World Skate Championships in Paraguay, with all the stories of the podiums, the 10-hour rain delays, and some pretty terrifying slams. We're also going to get into Chloe Cavell taking Street League Paris, and we're officially on the road to LA 28. And we've been blessed with no shortage of excellent skate videos that we're also going to get into. We've got the new Real and Crooked Good Company video, and then we'll take a little visual vacation over to Europe with Pocket Skate Mag, Daisy and Madelainey, poetic collective featuring moa zander and helen along the spots are what dreams are made of so is the free health care and then we'll head back to san francisco to check out great bubble gum with local rippers to

lula and cl and did you hear dvs is back so after that conversation about nostalgia i can only help but think is this the industry's most renewable resource and naturally my first question is who's going to be the token woman or gender expansive skater on the team And could we.

Possibly have more than one this time?

Plus, we have Amelia Brodka joining us to talk exposure coming up this November 6th through 8th in Encinitas, California. It's the great annual migration for women and gender-expansive skateboarders, outside of Wheels of Fortune, of course.

All this to say, it's a packed episode. Come hang out with us.

Good Luck With That is an iHeartWomen sports production in partnership with Deep Blue Sports and Entertainments.

We are your hosts, Ashley Rayfeld, Nora Vasconcellos, Alex White, and Mimi New. Our executive producer is Jesse Katz. Supervising producer, Tari Harrison. Video producer, Daniel Goodman. And video production by School of Humans. This podcast was created by Ashley Rayfeld. Listen to Good Luck With That, a skateboarding podcast, on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

Who Gets to Decide?

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