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May 4, 2026 18 mins

On the ground at the Deep Blue Sports & Entertainment Business of Women’s Sports Conference: what skateboarding looks like next to mainstream sports. WNBA Draft watch party and a full-circle moment with Sheryl Swoopes. Plus, talk on the growth of women’s sports and what skateboarding can learn from it.

We also recap:

Asian Skateboarding Championships Podium

Tampa Pro highlights

New Olympic pathway: 2026 U.S. Open video qualifier

Wheels of Fortune preview

See omnystudio.com/listener for privacy information.

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:03):
Good Luck with That is an iHeart women's sports production
in partnership with Deep Blue Sports and Entertainment.

Speaker 2 (00:12):
Hey, everyone, welcome to the red Pill Room, I mean
where everything's a simulation. I'm Ashley Rayfeld and this is
good Luck with That. Joining me today is Alex Whye,
Mimi Noop and Nora of Asking Sale. Those welcome. As
we got the game back together.

Speaker 1 (00:28):
We did something.

Speaker 2 (00:29):
Yeah, we're all here in New York.

Speaker 3 (00:31):
We're all in a very red room.

Speaker 1 (00:34):
Lights are on us. Okay, are rolling red rum red rum?
We uh yeah, We've been here for a few days,
attended some conferences. You guys already have filmed a podcast here,
but we're in it and it isn't like this is
what dreams are made of as a as a who

(00:55):
said that?

Speaker 2 (00:55):
Lidie Maguire, I.

Speaker 1 (00:56):
Don't know, but you did four pull ups last night.
I know on the street. We were like walking back
from dinner, pretty pretty loose, and ran into a group
of men just cheering each other on too, like a
push up pull up bar contest.

Speaker 2 (01:12):
That's right. It's like nine thirty elis.

Speaker 1 (01:16):
Felt like one am, and we just went to town.

Speaker 2 (01:19):
Most fun I've had all year, i'd say, I'm still
upset that you won. I try to step up to
it as well.

Speaker 1 (01:24):
Have you seen these shoulders.

Speaker 2 (01:25):
I have.

Speaker 1 (01:27):
The way to the world. I have the weight of
the world on my shoulders. So it turns out I'm
pretty strong.

Speaker 2 (01:32):
The way to women's skateboarding. That's right.

Speaker 1 (01:34):
I know not to try. The second you went up
to the pull up bar, I was like, this is over.

Speaker 3 (01:37):
Alex like fell off, like, yeah, well, I was just
trying to make your rails look good.

Speaker 2 (01:42):
Yeah, thanks for that. Well, we needed that skaters out there.
I gotta admit we have not skated the Brooklyn Banks.
It's on the agenda, it's it's the newly minted banks.
They're back, baby. Thank you Steve Rodriguez, Earl Hunter.

Speaker 1 (01:55):
Foundation, Thank you.

Speaker 2 (01:56):
Skate Park Project, New York City, unbelievable. Last time I
was there was two thousand and nine. I was there
for Skate Like a Girl with Christin Ebling. We caught
to skate the banks like literally right before it closed,
maybe the month before. It was like not going to
happen again for who knows how long or potentially ever.
And Jen Soto, little tiny Jen Sodo, her dad like

(02:17):
drove her on the session. I'm sure she was like
twelve or thirteen at the time. Ponytail, quiet as can
be comes to the first ever skate like a Girl
event and I just remember seeing her do it like
a pristine, perfect kickflip, and I knew something was special.
And fast forward now she's like one of the most
prolific female skateboarders out there on the streets. So so
cool to see the history there. Hopefully we'll get some

(02:37):
clips that we can be brave and post hard. You brave,
post hard.

Speaker 3 (02:40):
Well, we got to get a clip at the Brooklyn
Banks and apparently today is the day.

Speaker 1 (02:43):
So I think today is the day. Let's go one
hundred percent.

Speaker 2 (02:45):
Yeah, yeah, I'm down.

Speaker 1 (02:47):
We're going.

Speaker 3 (02:48):
Have you skated before?

Speaker 2 (02:49):
No? Have you? No?

Speaker 4 (02:50):
I don't think I've ever been there.

Speaker 1 (02:52):
I started skating like two thousand and six or seven.

Speaker 2 (02:54):
No, you're new to this.

Speaker 1 (02:55):
Yeah, So I'm just going.

Speaker 2 (02:56):
Maybe Steve Rodriguez met us that day at the banks
and then he made us push over the Brooklyn Bridge
and I just remember trying to like push as fast
as I could for dear life. And if anyone knows
Steve Erdriguez, that is the one ask that you deliver
on but we'll put you through the ringer today. So yeah,
stay tuned. We'll get some clips online. We should get
into the world women's skate news of it all.

Speaker 5 (03:16):
Outside of New York. They're actually is skateboarding going on too.
The Asian Skateboarding Championships just went off. I thought this
was really cool. The Chinese girls swept the park podium
and I'm gonna try to read their names coming in
third Zeng how How from China coming in second, Zao
Mink and winning women's park is ling Yang men who.

Speaker 3 (03:37):
We've actually seen at exposure before.

Speaker 5 (03:40):
In the women's street category from Thailand, Barrier Raya Suka
Sim got third place, Wang Yong ling Zoo from China
got second, and Geoshen got first.

Speaker 2 (03:51):
From Korea.

Speaker 5 (03:51):
Ge Oshen is crushing it in women's street and the
Korean team is coming up strong. And yeah, look like
a very very highly competitive event.

Speaker 2 (04:01):
Highly competitive is right, only knows the competition. Also in
the competitive scene of things, Tampa Pro just went down.
Nicole Haas shout out your massive fronts air over the
channel during the bowl session. So cool to see. Loved it. Also,
good luck with that pot cast guest.

Speaker 1 (04:23):
Yeah, ani al niy diy.

Speaker 2 (04:27):
That's right.

Speaker 1 (04:28):
If there's one thing she's doing right in Florida, it's
a jumping in that bowl. Yeah, she did an insane
invert to I don't I've never skated that set up there,
the bowl that they have outside outside Skate Park of Tampa,
but it looks it doesn't look like super easy, and
I feel like with that group of the Tampa Pro
energy is something that seems just a lot terrifying, terrifying,

(04:50):
which is why you opted out this year.

Speaker 2 (04:51):
Yeah.

Speaker 1 (04:52):
I was like Tampa Pro or New York with my
batty bitches.

Speaker 2 (04:57):
Hard hard call, really hard and moving into the video
competition scene at all. Me me, I think you have
some news to share.

Speaker 4 (05:05):
Yeah, we just launched on Monday, the twenty twenty six
online US Open is what we're calling it, and it's
basically a video submission contest for all US skaters that
meet the age requirements for the LA Olympics to create
a new pathway for kids to get into the qualifying system,
which will be in Rome in June.

Speaker 2 (05:24):
What's the age?

Speaker 1 (05:26):
I think you have to be fourteen by the LA Olympics.

Speaker 2 (05:29):
Okay, so you could submit as like a twelve year
old right now?

Speaker 1 (05:31):
Yes? Wow, think you have to be at least twelve
right now.

Speaker 2 (05:34):
Yeah.

Speaker 4 (05:34):
All the rules and eligibility information is on the Team
USA website. So if anyone's listening to this and wants
to enter, you have until April twenty seventh. Go to
the website, read about it, and send your video in.

Speaker 1 (05:46):
Sadie, I turned fifteen in like two months.

Speaker 4 (05:50):
You are eligible and eligible, you are eligible, you can
send us in your video.

Speaker 2 (05:55):
Vanessa Torus is also a judge on this, right.

Speaker 4 (05:57):
Yeah, so we have a world skate judging panel for
Street and Park and we are very very lucky to
have Vanessa on both panels for Street and Park to
you know, make sure it's all done very legitimate, legitimately.

Speaker 2 (06:11):
So yeah, thanks Vanessa. Okay, very cool. And then where
do they signd the video one more time?

Speaker 4 (06:16):
Go to the tmusa dot com slash skateboarding url.

Speaker 2 (06:21):
Okay, all right, you guys heard the orders. Also another
competition on the horizon coming in May.

Speaker 1 (06:27):
Oh, Wheels of Fortune.

Speaker 2 (06:29):
Guys.

Speaker 5 (06:29):
You guys are all coming right, you know, yes, May
fifteen through seventeenth, Seattle, Washington, the thirteenth annual Wheels of
Fortune The theme is retro. It's like four on one
video magazine late nineties, early two thousand's theme. We're gonna
have a bunch of pros out there. We're gonna have
a bunch of parties. Our welcome party is in a
punk rock flea flea market indoor. It's like an old

(06:53):
converted grocery store, and we're putting a bunch of like
crazy It's gonna be so fun anyway, crazy obstacles, crazy,
good time.

Speaker 2 (07:00):
Yeah, bring your for Dora, your skinny jeans, v neck
I have that.

Speaker 1 (07:05):
I'll bring.

Speaker 2 (07:05):
That's two thousands.

Speaker 1 (07:06):
I would say. I was gonna say.

Speaker 2 (07:12):
It's a cusp.

Speaker 5 (07:12):
It's like, you know, it's like whatever the kids can
kind of like think of for that era. That's what
it's gonna be. Yeah, and we're on a runway. Might
get some famous skateboard impersonators on this runway.

Speaker 2 (07:24):
It'll be it'll be pretty good. I'm very excited. I
can't wait for you guys to come and see it.

Speaker 1 (07:28):
I'm really excited. Yeah, because it's what been two years
since the last one. Yeah, we do them every two
years now, Yeah, which I like, I think it's a
way to do it. I think the calendar year is
pretty busy for everybody. And keep it fresh, keep it fresh,
keep it new. Yeah, we have a contest too, that's
trick and all that too. I'm not doing the witch hunt.
I'm sorry, but people should. People should do the witch hunt.

Speaker 5 (07:48):
Which hunt is like this giant scavenger hunt all over
Seattle the day before the contest for anybody that doesn't know,
and we put in challenges.

Speaker 3 (07:54):
We're gonna do it a little bit differently.

Speaker 5 (07:55):
This year, so we're gonna plant skaters like NPCs, like
like member an toniok pro skater when you come across
somebody and yeah, like and it's like it's it's you know,
Nora of askn Solos is at the vert ramp right now,
drop in an air over.

Speaker 3 (08:07):
No, you know, It's like we're gonna have challenges like that,
so you don't have to do any I like that.

Speaker 2 (08:11):
You could just be there.

Speaker 3 (08:12):
I would like that, wait for people to talk to you,
and then you can float around.

Speaker 1 (08:16):
No, I'm so down. I'm so so down.

Speaker 2 (08:19):
And speaking of you floating around, I saw you on
the internet doing the most unhinged hot sauce eating questions.

Speaker 1 (08:27):
Satan's right now, Yeah, just Satan draining. That was great.
That was really fun. Uh, buddy of mine, we got
bob lesel and Uh Robert Blasic interviewed me for that
and it was very fun. We ate six hot wings.
If you know me, I do not eat spice no
ever for good reason. Yeah, and then we were followed

(08:47):
up with eating like a fresh hobb and arrow. But
the questions I felt like they nailed it. I thought
it was so fun, got a little loose and just
went for it.

Speaker 2 (08:57):
Listeners, get your phones on Instagram. There's one clip that
I think I watched on loop. It's insane. Anyone I've
showed it to.

Speaker 1 (09:06):
We just don't talk about it enough. Skating with boobs sucks.

Speaker 2 (09:11):
I think you what was the quote? Was the direct quote?

Speaker 1 (09:13):
What did you say?

Speaker 2 (09:16):
Well, you have Portuguese boobs that are in your armpits?

Speaker 1 (09:19):
Yeah, just village feeders.

Speaker 3 (09:21):
Village feeders.

Speaker 1 (09:22):
It's really it's just like not getting easier, Like it's
like this weird thing of like you hit an age.
I'm thirty three, and I've hit this age where it's
like there's no coming back. They're getting bigger, they're moving
around to different areas and it's just like I can't
find a bra that word. So if anybody out there
wants to get home, this this a new market, I'm

(09:44):
saying skate bras.

Speaker 2 (09:46):
I think we just started a company. Also, I really
appreciated Robert Blasic being so lovely to actually be like, wow,
I hadn't thought of that. No, Robert's the shit, He's
the best.

Speaker 1 (09:55):
Yeah. Yeah, I've known Robert since like Woodward Days, so
probably like twelve years, and yeah, I think he is
just a really funny and authentic guy. But his questions
were perfect. Hey, good luck with datters. We'll be right
back after this quick ad break.

Speaker 3 (10:22):
What we're all here gathered here today for folks is
that Deep Blue Sports and Entertainment, in partnership with iHeart
Women's Sports, presented the business of women's.

Speaker 5 (10:31):
Sports some women five more times women women women. This
was I mean, honestly, the women in these rooms were
women were they were?

Speaker 1 (10:42):
They were so.

Speaker 5 (10:42):
Intimidating and dressed cool, and like I'm like wow, Like
I there's a whole spectrum of sports casual wear, and
then there's like sports businesswear, and then there's like sports
at leisure afterwhere, and like I'm learning so much.

Speaker 2 (10:55):
And then there's Sports Style magazine where and then they
let the skateboarders in and I just want to hear
I've gone to this conference of your time. I think
it's amazing because you learn so much about what's going
on in these bigger sports spaces. It was such an
honor to be here during the first ever WNBA draft
with this new CBA agreement and really seeing women get
paid what they deserve. We were at the watch party

(11:18):
and the one moment that was just kind of insane
to me was Cheryl Swoops is there, which she is
the first person drafted to the WNBA in nineteen ninety seven.
I mean, she's just the greatest female basketball basketball player
of all time. She gets on the mic and talks
about that experience of what that was like to be
drafted then and what she was getting paid at that point,

(11:40):
to see how far the bar has been moved to
now and talking about it and watching her actually like
shedded tear during that moment.

Speaker 3 (11:47):
It was incredible to be in the room. It was
like all rise for Cheryl Swoops.

Speaker 2 (11:50):
So that was such an honor to just be mixed
in with these icons and also just to celebrate skateboarding
within this space because people often don't think of it
as a sport, and I know we talk about that
a lot on this podcast, but we are entering this
new world of sportified skateboarding and so we got to
be there.

Speaker 1 (12:10):
Yeah, And I think so many of us have taken
inspiration from other female athletes. I know, like I was
obsessed with soccer as a kid, then surfing, and those
women were paving away and making a living and they
had these careers, and I think as a skater it
was like, how do we adopt this? But also we

(12:30):
come from an industry that's fueling everything, whether it's like fashion, music, art, streetwear,
Like they're taking from us as well. So I think
it's really cool to be able to be in a
room where we're getting to yeah, be involved, you know,
sitting at the cool kids table.

Speaker 2 (12:47):
Also, I think every athlete has a little bit of
street skateboarder in them, Like at the end of the day,
like what they're doing is like still has all physical
like body risk to it.

Speaker 1 (12:57):
Yeah.

Speaker 4 (12:58):
I felt like it was really interesting listening to some
of the panels just saying the parallel challenges in mainstream
sports compared to you know, the challenges we deal with
in skateboarding action sports. So yeah, what I took away
from it is if someone at the top can see
the vision of what's there to invest in and they
do it. And yeah, it was cool to kind of

(13:19):
see people you know that are doing that in some
of these stick and ball sports as we call them.

Speaker 2 (13:25):
Yeah.

Speaker 3 (13:26):
I really liked Shane Jones from Grow Basketball.

Speaker 5 (13:29):
So she's doing free girls basketball summer camps and free
after school basketball program which is so much like skate
like a girl for us too, and she's like, kids
just got to go play. She's a kindergarten teacher too,
and that was my absolute fair person and the one
I came up to right after too. I'm like, oh,
we speak the same language, we're doing the same thing.
We're trying to like get kids.

Speaker 2 (13:46):
Active and having fun. I loved her.

Speaker 1 (13:48):
I think that was like yeah, yeah, and I think
skateboarding too, it's just such an accessible starting point. Yeah,
compared to the sports and the like kids these days,
you're seven years old and if you want to join
a league, it's like highly competitive and they are trying
to like create these elite It's like you're a kid,
You're just trying to create community. You're trying to learn

(14:08):
a sport, you're trying to challenge yourself and have fun,
and I think a lot of that gets left behind.
But skateboarding and skate like a Girl really shows that
every age and anybody can have like a chance to
learn to skate and it is in as long as
you have a paved driveway, as long as you have
a space to roll around just a little bit. It's

(14:30):
it's there and like affordable. So yeah, and I loved
all the big personalities.

Speaker 5 (14:35):
Seeing Sarah Spain in real life stand up comedy or this,
it was like one of the two for her. She's
so funny and god like they're like Renee stubs, like
Ashlyn Harris, like all these like really big hilarious people,
like big personalities in the room all the time too,
And hearing them talk about their sports and steering opsess
they were too made me feel like a not so crazy.

Speaker 2 (14:55):
Yeah, there was like such a theme. It was just
like coded in different words. They were basically all blaming
the deep level of obsession and commitment and just like
the like OCD of it all that we kind of
have with skateboarding like they have it in their sports
like they had to continue to show up, you know,
day after day, year after year, and rise to It

(15:15):
was up to them to be as great as they
were going to be, and it's up to us as skateboarders.

Speaker 3 (15:19):
We don't even have coaches, though, so it's kind of.

Speaker 2 (15:21):
Crazy that we've still arrived here independently. And to your point,
nour just need a skateboard and driveway and the rest
can be yours. So it's a pretty magical thing that
we have easy access to. And it was just so cool.
I was so happy to have you guys there. Way
more fun to be in the rooms with you all
running around and being professional, but also we were so professional,

(15:46):
lightening up the room a little.

Speaker 1 (15:47):
We did good. We did. We were on our behavior.

Speaker 3 (15:50):
I kept walking in the wrong doors and getting yelled at.

Speaker 1 (15:52):
You did, Yeah I didn't.

Speaker 3 (15:53):
I could not understand the curtain and the door situation.

Speaker 2 (15:56):
That's right, Yeah, but it's kind of fun.

Speaker 1 (15:58):
I kind of like getting yelled out on, like Sun,
aren't you supposed to be in school today?

Speaker 3 (16:04):
They did the group and he's like, it's so nice
that they brought their son up there with them.

Speaker 1 (16:09):
I fully had my hands on your shoulders I'm so proud.

Speaker 2 (16:14):
Yes, that was a pretty amazing past couple of days.
We also got to interview Leo Baker. Yep, so that
was rad. Episode is out now so check it out.
What an honor And uh yeah, we've got a few
more days out here, so a lot to happen. Do
you guys need some luck for the rest of the week.
I'd love to hear about what you're searching for. I

(16:35):
need some electric lights last night.

Speaker 1 (16:38):
I need two extra hours of sleep a day.

Speaker 3 (16:41):
I need to figure Okay, I think in my head
that I can do the bank to wall at the
Brooklyn Banks.

Speaker 2 (16:45):
That's what I wanted to do and do it. You
guys can do it, but I don't know. You're goofy
right in regular Oh god, damn it. Well that's the
same clip.

Speaker 3 (16:55):
Would have just walked out, but I was going to
all to the wall. Oh okay, Well, we're gonna see.

Speaker 5 (17:02):
Good luck is just basically, after we get through these podcasts,
we're gonna go to the Brooklyn Banks and we're gonna
skate there and hopefully it gets close.

Speaker 2 (17:09):
Yes, stay tuned, please think of me and your thoughts.
We're gonna pull us. We're gonna go to get this.
We haven't skated it all this week and last night,
as we mentioned, was wow. So here we go.

Speaker 3 (17:25):
Where to go?

Speaker 2 (17:26):
All right? Listeners, you can find us at good Luck Pod.
Wherever you listen to your podcast, you can also find
us there and great review like subscribe, Yeah, tell us
about it again. I want to know who you are
out there.

Speaker 1 (17:39):
We're here for you.

Speaker 2 (17:41):
And this is good Luck with That. Good Luck with that? Yeah,
hey kid, good luck with that.

Speaker 1 (17:54):
Good Luck with That is an iHeart women's sports production
in partnership with Deep Blue Sports and entertain We.

Speaker 6 (18:00):
Are your hosts Ashey Rayfeld, Nora bas Gonzalos, Alex White,
and Mimi nu. Our executive producer is Jesse Katz, supervising
producer Tari Harrison, video producer Daniel Goodman, and video production
by School of Humans.

Speaker 3 (18:15):
This podcast was created by Ashley Rayfeld.

Speaker 6 (18:17):
Listen to good Luck with That, a skateboarding podcast, on
the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
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