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April 24, 2026 46 mins

Leo Baker joins GLWT. 
This episode covers a lot of ground.

Two-time Super Crown champion. Eight X-Games medals. First trans person to have a signature shoe on Nike. A body of work and video parts that we're still talking about. 

We get into being shaped by an industry that decided what was “marketable,” and the cost of surviving inside it. Walking away from the Olympic path to transition. Building brands like Glue and Tacky.


Process, obsession, and what it actually takes to own a trick.

Choosing yourself is the whole story.

See omnystudio.com/listener for privacy information.

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Episode Transcript

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Speaker 1 (00:03):
Good Luck with That is an iheartwomen's sports production in
partnership with Deep Blue Sports and Entertainment.

Speaker 2 (00:12):
Hey everyone, I'm Ashley right phone, and I'm Alex White.

Speaker 3 (00:15):
And today on Good Luck with That, we have the
very lovely guest, one of my good friends, my brother
from another mother, Leo Baker, is joining us today on
the Pavlio.

Speaker 2 (00:24):
Thank you so much for thanks for having me. Yeah,
we got to New York and you were our first
phone call.

Speaker 1 (00:28):
I'm honored that a two time Super Crown champion, eight
X Games medals, filming, massive video parts, first transperson, having
the signature shoe on Nike, tons of accolades, just in general,
a major motion picture documentary called The Leo Baker Story.
I Get on board on Netflix? On Netflix, do you
pick me up from JFK?

Speaker 4 (00:49):
I did? I love you a lot?

Speaker 2 (00:51):
I love you a lot.

Speaker 1 (00:52):
Thank you so much. I wanted to know, like, what
have you been up to lately?

Speaker 4 (00:56):
Keeping it really simple.

Speaker 5 (00:57):
I have just been skating and I've been in the
gym and just hanging out with Carlos, my dog.

Speaker 4 (01:03):
Thank you for Yeah, everyone's like, who the fuck is Carlos?

Speaker 2 (01:07):
Uh? Yeah, six year old baby boys.

Speaker 4 (01:10):
That's not chill. It's crazy.

Speaker 5 (01:13):
He's good, yeah, playing music whatever, keeping it simple and tight.
Nothing really complicated is happening in my world? Well your
world used to be a lot more complicated, fee yeah,
and I'm like done with that now, okay, But like
twenty years of skateboarding, what's it feel to be like

(01:34):
just starting.

Speaker 4 (01:37):
I'm kidding obviously, I mean, I'm like.

Speaker 5 (01:39):
I could, we could do it, we could go there.
I mean, there's just been a lot of beginnings within
the span of my career, but this one does feel
new in that I'm like, no more any bullshit at
all and just video parts and filming and shooting photos

(02:01):
and like no other people. What's the bullshit part the industry,
the people running the industry.

Speaker 4 (02:08):
The show is a way that.

Speaker 2 (02:12):
The way that.

Speaker 4 (02:15):
I don't Oh my god, there's just so much.

Speaker 5 (02:16):
I mean, it's like a microcosm of the world at large,
you know, right, people are just disenfranchised based off of
things that are not within their control, and.

Speaker 4 (02:28):
I just think that's so fucking lame. But we all
deal with it.

Speaker 2 (02:32):
You've been navigating it since such an early age and
in the public eye, and you've had many chapters because
life has lots of chapters, and I'm just so excited
to hear about your perspective on it all. But that's
going to be developing, and I'm really excited to hear
that you feel like you're in a different chapter with it.
Yeah again, Yeah, you're still skating incredibly. Well.

Speaker 4 (02:51):
I saw its yesterday. I just love skating.

Speaker 5 (02:55):
It's just so fun Like trying to get me to
not skate, like it's not going to work.

Speaker 1 (02:59):
I think it's so funny to watch your process.

Speaker 4 (03:03):
Can you talk a little bit.

Speaker 5 (03:06):
It's hard for me to talk about it because I'm
in it, but like you were a witness to it yesterday.

Speaker 4 (03:11):
Yeah, so maybe you can discribe it mad things.

Speaker 2 (03:14):
I would like to use the word obsession, like you
get really obsessed with a trick, like for a long period.

Speaker 4 (03:19):
It's that trick. Yeah.

Speaker 1 (03:21):
Well, also like you have been skating for so long
and you have gone through so many iterations of obsessions
in like a genre of skating, like it'll be manuals
for a long time, Like right now you were like
into like faky slides forever.

Speaker 4 (03:34):
Oh, I love it.

Speaker 5 (03:35):
I still like that. Yeah, Like I'm like trying to
apply that lots of places.

Speaker 4 (03:39):
Like what are you?

Speaker 1 (03:39):
Like, is that your current obsession?

Speaker 5 (03:40):
Like I'm really into faky just doing shit fakey uh
and switch nose manuals. I'm like, Okay, I need to
like get my shit together before it's too late and
like get good at that trick.

Speaker 4 (03:53):
And like front croas just tricks that like.

Speaker 5 (03:55):
To me when I was younger, I would see them
and be like, damn, that looks like a hard trick.

Speaker 1 (04:00):
Like what tricks did you struggle with when you were
younger that you are grasping now?

Speaker 2 (04:07):
None? Have you watched Leo skate? Yes, I'm so sorry.
What's funny?

Speaker 4 (04:11):
Fakey manuals.

Speaker 5 (04:11):
Baky manuals are hard, have been hard, Like the just
it's not even the trick, it's the confidence. Yeah, that's it.
It's like building confidence to like commit to a trick.
That's the hardest part. And when it's a new trick
or it's like a different direction or I just haven't
built up that muscle, it's scary. But then once I
build the muscle up, I'm like, oh my god, I
could apply this so many ways.

Speaker 4 (04:32):
So it's just like repetition.

Speaker 5 (04:34):
I just do the same shit, yeah all day, Like
learn I learned kick floop back tail by doing I
was so sick of not having it consistently, like you want,
Like I did one when I was sixteen, and I
was like, okay, cool, I can do it, but then
I like couldn't really do it. Like it's like there's
a difference between like doing the trick like oh I
did a kickfloop back tel and being like I know
how to do that.

Speaker 2 (04:54):
Okay, that is your skateboarding Leo, because I think everything
every scene you do is you don't like bring it
out and from the public until you own it. And
I think you do that with everything you do in life.
You're you're gonna like reiterate, You're gonna reap, You're gonna
like master that thing and then it's yours to keep
and have forever and you have it on lock like
that and even your music Like not to talk you
too up, but like it's pretty cool. I think it's

(05:16):
like a really amazing process. I'm too lazy to do.
You're gonna have to help me carry my head out
of here. But like baes are yours every sing under
the sun.

Speaker 4 (05:28):
I'm still worrying, dude. Switch trays like I leand like
two A year.

Speaker 2 (05:32):
Yeah, land a trifle. Tell you're ninety in my eyes,
I'm sure you will.

Speaker 4 (05:38):
Then, Yeah, we'll see. I'll try.

Speaker 5 (05:40):
But yeah, the kick flip back tail, like I was so,
I was like so done with like not being able
to like just do it. And then I was like,
I need to like figure out how to do it.
So I was like, Okay, I'm gonna do kick flip
backside five os every single day for a week. Nothing
else in my brain going on, just that kick kick

(06:01):
flip back five okay, and just all day every day.
And then I was like, okay, now I just got
to put the tail down because you get I got
the timing of the flip to the ledge and so
then I just same thing except turn it to the tail.
And then I was like boom, only to fucking twenty years.
I'm not kidding, I'm thirty four, seriously.

Speaker 1 (06:19):
Like, That's what I think about with you a lot.

Speaker 2 (06:20):
Too, is that it's never too late everyone out there, Yeah,
never too late.

Speaker 1 (06:24):
Really well, when natural talent meets obsession, like you are
obsessed with skateboarding to a degree that I think a
lot of people don't really fully grasp, like you look
like a natural talent, but you're really a hard worker.

Speaker 4 (06:37):
That's my thanks, low Ki. Yeah.

Speaker 5 (06:38):
Yeah, It's it's intense because, yeah, when I feel that,
it's like a drive. It's like a biological need that
I must go after. Like I woke up yesterday morning,
like obviously not warmed up, like you know, kind of
like limping around from the skating five hours a day before.
But I'm like, I like have to skate that fucking ledge,
Like I like I was the I was like thinking

(07:00):
about it. I was like, should I go? I know,
and I'm like, I should not go? Should have a
podcast with us rest? Yeah, like maybe I should just
go hang out there. And then I'm thinking, like my god,
what if I went out at Switch, Like think about
the hours of figuring stuff out that could happen just
skating and Switch.

Speaker 4 (07:18):
I don't know so much to discover, but you.

Speaker 1 (07:21):
I think you like really at this stage of your life,
like putting your mind into skateboarding because from a really
young age you had to support your family and do
so much more.

Speaker 4 (07:31):
Can you talk a little bit about that.

Speaker 5 (07:34):
Yeah, it's like a double edged sword because it was
just it kind of just felt like I was always
in the right place. At the right time, Like I
met the right people at the right time that guided
me to like, I don't know, like Ryan Miller meeting you, meeting.

Speaker 4 (07:48):
Lisa Whittaker shout out on good luck.

Speaker 5 (07:54):
Every episode we shout out, well it's happened every time
it comes up every episode ye in mayor yeah that's right,
of I don't know skateboarding.

Speaker 2 (08:04):
Yeah, okay, well so so then yeah, so I was
like people were just I guess, like noticing how fucking
talented I am.

Speaker 4 (08:13):
I hate Oh, it wasn't even about that. It was
about the hair.

Speaker 5 (08:17):
They're like all the like pedophiles running everything were like,
we can't wait to get that child in skinny jeans.

Speaker 2 (08:24):
Yeah, you were a blonde I'm not kidding, amazing young skateboarder.

Speaker 4 (08:31):
It is true.

Speaker 2 (08:32):
You fit the archetype that they were looking for and
you have the skills. It was like this perfect cosm.
But you were a child.

Speaker 1 (08:37):
Yeah.

Speaker 5 (08:38):
I remember being in a meeting that was like they're
talking to my mom, but I've been in the room,
but like I feel like they think I can't hear
them or something. Have you ever had that experience with
adult Like you're like, I'm like right here, they're like talking.
She's talking to my mom and she's like, oh my god,
so marketable, like down to the name. It's like the
long blonde hair and the style and the name your name.

Speaker 1 (09:02):
Can you give us your fall dead name?

Speaker 4 (09:04):
Yeah, it's roner Baker.

Speaker 2 (09:12):
Hearing that is like.

Speaker 5 (09:16):
Marketable. I mean they didn't know about the three middles.
Well it's two middle to last. Ron Baker is my
last name, so I still have that now. My name
is Leo Marshall Roner Baker.

Speaker 4 (09:28):
Leo.

Speaker 2 (09:29):
How much have you been crying lately?

Speaker 4 (09:31):
Like, not at all? What's up with that? I think
it's I think it's being on tea.

Speaker 5 (09:37):
Oh it's like I can't cry unless I'm like so mad.
Oh no, I'm on like so much prozac. Okay, oh
maybe it's that. Could be some people can cry.

Speaker 2 (09:48):
I think it's the tee thing.

Speaker 4 (09:49):
I think so too, because that's why I just don't cry.

Speaker 1 (09:52):
Boys boys kidding, like the.

Speaker 4 (09:57):
Movie don't bring that movie yep. I and that's the worst
the world. Sorry about that, but how dare you?

Speaker 2 (10:03):
I know? Yeah, okay, so we're not crying a lot lately?
Is this a good thing?

Speaker 4 (10:07):
Yeah?

Speaker 5 (10:07):
I mean I'm just like like I said, I mean
keeping it really simple.

Speaker 4 (10:11):
I like wake up, I eat breakfast.

Speaker 5 (10:14):
I like skate, I work on tacky stuff with Alex,
and I hang out with my dog. And I'm just
like in other ways, not just skating, but working on
like music, Like I'm I'm signed up to this thing
called pickup music where you can like follow different learning
pathways about just like different styles of guitar that you
want to learn, and there's so much information in there

(10:38):
it's sick. I'm like, I wish that there were two
of me so I could do two lessons at once
and learn both things. It's just like, you know, it
takes time to get through it, yeah, and that's what
that's really what I'm learning these days is like when
I was younger, and I still believe this. I'm like
I've always been like my mindset's been like it's not

(10:58):
like I can or can't. It's like do I want
to and do I have the time to figure it out?
When I was young, I was like, oh, I have time.
I have so much time to figure everything out. And
I was like I want to like get good at
piano and like violin and like fucking start a band
and like tour and like have a family and like
all this shit.

Speaker 4 (11:14):
Now, I'm like, oh, I'm.

Speaker 5 (11:15):
Like thirty four years old, so I should like stick
to my main instrument guitar. I can like work on singing.
I can like definitely just stick to skating, like making it.
I don't know, Like I'm like, okay, maybe we're not
going to master the piano.

Speaker 4 (11:28):
In this lifetime.

Speaker 2 (11:29):
Never say never never see.

Speaker 4 (11:31):
Yeah, I'm like, I'm I still I think I have
like two thirds.

Speaker 2 (11:34):
Knowing you and your session. I could see you.

Speaker 4 (11:36):
Yeah.

Speaker 5 (11:37):
Well now that I like prioritize sleep, Oh, that takes
up a lot of time.

Speaker 2 (11:41):
Horizontal. Yeah, I feel like every time we talk, I'm like,
what are you about to You're like, nap.

Speaker 4 (11:46):
I take a nap every day sometimes too.

Speaker 2 (11:48):
Yeah, I admire that about it. I'm like really hyperactive,
and my partner often says, I'm like a dog like
needs to be like constantly let out and if I
don't get my exercise, it kind of it doesn't have
a short circuit.

Speaker 4 (12:02):
It's like emotional regulation.

Speaker 5 (12:03):
Like you take a nap to like clear the slate, clear,
clear the palette.

Speaker 1 (12:08):
Tell Ashley about the trick you taught me, Like the
not nap nap.

Speaker 5 (12:12):
It's yeah, just lay down for twenty minutes with no yeah,
set a timer, close your eyes for that amount of time.
Do stimulates quiet you're laying down, things are soft like pillows, yeah,
and the bed or wherever.

Speaker 4 (12:26):
Yeah, And it's just like shut down.

Speaker 5 (12:28):
And then you come back and you're like, okay, Like
I don't know, it's like a reset.

Speaker 2 (12:33):
You telling me that is a reset. It's like sounds
like so much peace.

Speaker 5 (12:37):
It works so well. I did it today for an hour.
I was like, okay, we're going in the dark. One
hour and I fell asleep and then I woke up
and I was like, oh my god, forty minutes has
already gone by.

Speaker 4 (12:47):
I need more time.

Speaker 1 (12:49):
Well, I think it's it's like a it's a there's
like a really good theme emerging around this too. And
and I see this hee in you in your life
where very chaotic, very we think I'm emerging about this,
Like you had like such a chaotic upbringing and there
was so much overstimulation, and you moved to New York
six years ago.

Speaker 2 (13:09):
Yeah, when did you move to New York?

Speaker 5 (13:11):
I moved here the day after Donald Trump got elected
the first time, so I was in twenty sixteen, Like
I stayed in LA because I was registered to vote
there and I was like, well I have to vote
and then I'm out of here.

Speaker 2 (13:23):
It's kind of like I remember the day so well.
I think everyone can remember the day. It's almost like
the story of like you ask where you were during
nine to eleven universal with Donald Trump, and like everybody
is like split, but with respect to so many real talk,
serious lives that were lost. But it is these like weird,
like these moments that just like stop you and you

(13:45):
have these core you have this immediate memory. So you
were twenty sixteen, you moved to New York City.

Speaker 5 (13:49):
To yeah, okay, so I I was like ready to
get so ready to leave LA. I was like, did
you get me the fuck out of here? I didn't
have like any kind of a going away thing. I
went to a cafe stellar by myself and got a
steak and was like there and it was just like
me and the bartender. And then I was like watching
the the map, you know, as it turns whatever color
blue or red, and I was like each state just

(14:10):
kept turning red and it's just me and the bartender
were both just like this this is not a good situation,
and I just whatever ate my food and then went
back to.

Speaker 4 (14:22):
Vanessa's Vanessa Taurus.

Speaker 5 (14:25):
I was staying with her because my apartment had the fire,
so that.

Speaker 2 (14:30):
My god, I forgot about the fire.

Speaker 5 (14:31):
So that's why I moved to New York and November
instead of the spring. But regardless, I uh yeah. Then
I went to the airport the next day with my
cat Maxi.

Speaker 4 (14:39):
And just dismal vibes.

Speaker 5 (14:44):
And then okay, like the pilot of my plane like
saw me there hanging out Maxi, just in the waiting area,
and he like came up and was like, oh, I
love cats, Like you should bring her up to the
cockpit like at the end. And I was like, oh
for sure, like hell yeah, like whatever. He seemed like
a nice enough guy. And then as he's walking away,
like on the bottom of his luggage has a Trump
bumper sticker on it, and I was like, I was

(15:07):
just I was like a Trump supporter, like held my cat.

Speaker 4 (15:11):
That's weird.

Speaker 5 (15:12):
Oh no, like he voted for Trump, Like he wants
me dead, Like yeah, probably doesn't like trans people, definitely
hates women.

Speaker 1 (15:19):
Yeah, but he loved your cat.

Speaker 4 (15:21):
He liked the cat though, huh.

Speaker 5 (15:23):
I'm like, what if I was like, what if he
knew I was trans but then I didn't even transition yet.

Speaker 4 (15:28):
I don't know. He probably thought I was like twelve
years old or something.

Speaker 2 (15:32):
These things happened, Yeah.

Speaker 5 (15:34):
Yeah, but I was like, I just remember, like my
skin just thought like my skin was crawling in that moment,
like him walking away, like to fly the plane, and
I'm like.

Speaker 4 (15:44):
These are the people in charge? It just blows me away.

Speaker 2 (15:48):
Yeah. Well, the good news is you look great in
New York City.

Speaker 4 (15:52):
Thanks.

Speaker 2 (15:54):
All right, everyone, We have more with Leo. We'll be
right back after a quick ad break. We keep talking
about all these different moments in your life. You've had
so much life happen. Everybody does. But I feel like

(16:15):
because we've been able to watch you just grow up
in front of us, in front of skateboarding, it's been
cool to see the New York version of you. You
became a pop star, Leo. Pop star for those that
don't know, yes, you you're skateboarding. In terms of the
video parts you're putting out because you were filming often here.

Speaker 1 (16:32):
The documentary so sick knowing on the documentary, can you
talk for saying about that part in your mind. I
feel like that's a big uh marked clip, so to speak.

Speaker 5 (16:41):
In twenty twenty one, Yeah, okay, so yeah that was
a crazy time because I feel like just everything was
coming to a head, like skating in the Olympics and
like all this shit, and like I'm just like another
fucking year. Like I'd been like trying to just get
a top top surgery console since I was like twenty

(17:02):
five or twenty four to twenty five, and like I'd
be traveling for competitions, but the console you have to
book like eighteen months out.

Speaker 4 (17:10):
So I'm like, okay, I was, I have a date,
but I might.

Speaker 5 (17:11):
Like be in fucking Norway or like wherever the fuck
we were going that year. So I was just every
year missing the console and like just was like I
like I And then so then I was on the
Olympic women's team and I just was I just was
like I can't fucking do this, Like I just can't,

(17:34):
I cannot do this. And then yeah, because I like, well,
I booked my top surgery date finally for the the
fall after the Olympics in twenty twenty, but then it
got postponed. But like I sent my I texted me
me and I was like, I think I'm actually gonna

(17:55):
like not do this, and then she was like okay, cool,
like just send me an email like stating like your resignation.
I was like, so immediately am I standing in my
kitchen like emailing from my phone like I'm not doing this?
And then it got announced like within weeks that it
was getting postponed because of COVID.

Speaker 4 (18:17):
So I was like, thank god anyway, So that so
the documentary.

Speaker 5 (18:24):
The way that the documentary relates to that is like
Rehdta was like, you know, I want to do a
movie about you whatever, and I was like, okay, sure.
I was always say yes to everything because that's how
I was raised.

Speaker 4 (18:36):
Say yes, make people happy.

Speaker 2 (18:39):
So am I hearing you would do it differently.

Speaker 5 (18:41):
Now I have I have a lot of thoughts in
my post documentary years.

Speaker 4 (18:46):
Okay, I'm just take us through the through line. So Redda'
is like, I want to do this movie, and I'm
like all right.

Speaker 5 (18:53):
So we did like film as Sizzle, and the pitch
was non binary skateboarder on their way to the Olympics,
and Netflix bought that. They pitched it around in to
like different networks Netflix bought it and then it went
into production and that was truly the story until like
my gut was just like, okay, the story is changing

(19:14):
like today, Like I was, I was gonna go for
the Olympics. Like I was, like, this is the only
life I know. I mean, besides street skating, it's like, Okay,
in competitions, it's like, am I not gonna do the Olympics?

Speaker 4 (19:26):
Like yeah, like for.

Speaker 5 (19:27):
What I'm like, obviously for this reason, I'm like, okay,
it's a really good reason not to do it, but
like otherwise I probably would have fucking gone. But I
was like, dude, I can't. And I remember, like the
last time I competed was in Rio Rainy one and
I had a fucking sick ass bender after that because
I was standing up on the quarter of pipe waiting

(19:50):
to drop in to take my run and then they
announced my fucking dead name and then I'm like I
want to kill myself. And then I do my run
flawlessly and with lots of style and grace because as
you guys know, I work really hard on that and
I didn't even make the fucking semis and like, sorry not,

(20:11):
I love that. But the thing that pisces me off
is like, Okay, this.

Speaker 4 (20:19):
Is gonna be a controversial thing. Please.

Speaker 5 (20:23):
From my experience watching how competitions develop, they see, okay,
what what did the person do last year that won
that contest? Then everybody goes and learns that trick. The
year I won Super Crown, I was doing no slide
two seventies and no slide bigspins, and then what was like,
you guys like everyone's doing that trick, which I'm like, great, cool,

(20:45):
like you guys all learned it, but I'm like they're
not doing it good or going fast.

Speaker 4 (20:49):
Dude.

Speaker 2 (20:49):
We talk about this all the time.

Speaker 5 (20:50):
They're like, do all these hard tricks, but they like
looked so bad. Yeah, and I'm like talking about how
did that person make the finals over me?

Speaker 2 (20:59):
I'm fucking hauling ass out here.

Speaker 4 (21:01):
Yeah.

Speaker 5 (21:01):
So then I went and got like so much fucking molly,
and it's like on the beach, I.

Speaker 4 (21:05):
Was all sunburned and shit, and then I was like, yeah,
I'm done with this.

Speaker 5 (21:09):
I'm done with this. I'm done with it. Like I
was like, I'm fucking not. I can't, like I can't
do this anymore. My spirit is like drowning.

Speaker 2 (21:20):
You saved yourself.

Speaker 4 (21:21):
Yeah, I'm like, dude, fuck this.

Speaker 2 (21:23):
I mean, we'll get back to the bender, but you
didn't save yourself and I'm really proud of you about that.

Speaker 4 (21:28):
Thanks.

Speaker 5 (21:29):
Yeah, I mean against all odds too, Like everyone like
being on the phone with like previous managers and they're
like are you sure? Like they're like, I support you
no matter what you want to do. They're like, are
you really sure you want to quit the Olympics. So
I'm like, I'm pretty sure. But it's like the same
thing as like.

Speaker 4 (21:44):
Do you want to cut your hair off?

Speaker 5 (21:45):
Like do you want to It's like this theme of
like me feeling a way that they all I'm trying
to align with myself and then people nobody understanding it
and people being like, but like you're successful because of
these reasons, and I'm like, yeah, but this is who
I am. And so it's like cutting off my hair
and like dressing fucking masculine again, and then like quitting

(22:07):
the Olympics. Everyone's like, that's the most insane choice you
could make. That's because it's like you're going to the Olympics.
Like who could say that. I'm like, I don't care
what the fuck I can say? I just I don't
even care, Like it's not even my dream, Like this
is your guys' dream, right for me and for all that.
Like I didn't, like, I didn't start skating to set
out to like go on this Olympic mission. I'm like,

(22:27):
I skate because I like fucking skating and like grinding
curbs and making stuff out of nothing and like being
with friends and like whatever fucking Debocher's shit we get into.

Speaker 4 (22:37):
I'm not like out here to be on the fucking
it's so sterile.

Speaker 2 (22:41):
Oh my god, it's so boring.

Speaker 4 (22:43):
Oh god, sorry, No, I have more to I have
more to say, let's go.

Speaker 5 (22:46):
And then when I'm like in the fucking so so
now I'm like, okay, so I'm on the Olympic team, right,
and they're like.

Speaker 4 (22:55):
Fucking people like, uh, what's the what's the drug? People
want to this woman? Okay, my phone like nine missed calls.

Speaker 5 (23:04):
I'm like, if I have a nine missed calls, like
somebody died probably right, yeah.

Speaker 2 (23:10):
And three voicemails.

Speaker 5 (23:11):
But and this is lady Susan outside my apartment at
six o'clock in the morning to like get my pee.

Speaker 2 (23:16):
Oh the drug testers. Yeah, and but like Nicole has
a good.

Speaker 4 (23:19):
Story about the one.

Speaker 6 (23:20):
Oh it ruined everything, like it really really really ruined everything,
Like when I won or right, I like got the
podium at U fucking sell Polo one year.

Speaker 4 (23:32):
I don't remember what year it was.

Speaker 5 (23:34):
And then like the whole that's like the best moment, right,
everyone's like yay, you won, and you're holding a trophy
and all your friends and there people are taking pictures.
They take you and you go into a back room
that's like dusty and there's no windows and you're there
with a fucking clipboard and there's like some lady here
whoever the fuck, and then has to watch you lift

(23:56):
up your shirt, pull your pants down, show your full
name naked body, so that there's no like fake pea
bag fuck, I mean, get it, do whatever, but like
I'm not doing that.

Speaker 2 (24:11):
You're not.

Speaker 4 (24:12):
You don't compacity for that.

Speaker 5 (24:15):
So and then finally I pe and then they'd take
it and then they'd fill out the foot, do all
the fucking paperwork, and then then you walk out in
the rain is empty, everyone's gone, and you're like I'm starving.

Speaker 2 (24:30):
So this is why you actually quit the Olympics, not
because your life depended on it. It was the pea bag
and lady, I'm kidding. Obviously that didn't help.

Speaker 4 (24:39):
And I but it was like the gender thing on
top of it.

Speaker 5 (24:42):
I'm like, I have to show my pussy to someone
maybe tomorrow at six a m.

Speaker 2 (24:46):
Yeah, any day leading up for the next three years.

Speaker 4 (24:49):
What the fuck?

Speaker 2 (24:50):
Yeah, it's even worse now. Oh I'm sure, yeah, it's
even worse now.

Speaker 1 (24:54):
Sit tight, We'll be right back after this quick ad break.
How does it to like turn your back on all
that pressure and all that stuff? And it makes sense,
but like, how is it to choose yourself over that?

Speaker 2 (25:16):
You know?

Speaker 5 (25:18):
I mean, it's just it feels like a lot of
that stuff and so many iterations of myself growing up
were modes of survival.

Speaker 4 (25:30):
Like it was like.

Speaker 5 (25:33):
They weren't like you have to wear these skinny jeans,
but they were they can be like but like we
like nudge, like we like meaner of youone. And then
event I like got the hint that like they weren't
gonna fucking market me if I'm dressed like a boy
and my mom can't afford to pay for anything, and
like this is like okay, I can secure a bag

(25:54):
if I like, I can like get one step closer
to my goal to making money, to like things.

Speaker 4 (25:59):
That are like first Survival.

Speaker 5 (26:04):
If I just make this one adjustment, just wear skinny jeans, okay.
And then they're like, we'll try on this like shirt
and it's like a deep V. Well first regular V
and then like deep V. And then I'm like, there's
a kick. There's a photo of a video clip of
me doing a kick like the best. I would like
use this clip like five times in a video. I
wouldn't even care, but you could like full cleavage, low

(26:26):
cut tank top, like titties bouncing like I made least
to take it down from.

Speaker 2 (26:33):
No.

Speaker 4 (26:34):
This was like post Fedora.

Speaker 5 (26:35):
This was I was seventeen, okay, okay, and I'm like,
I can't believe I skated dress like that, like so uncomfortable,
so vulnerable, like so much skin showing and shit, it's
just like.

Speaker 4 (26:51):
What the fuck.

Speaker 5 (26:54):
I remember coming out of like one of we would
call it. They called it like a walk through.

Speaker 4 (26:57):
Each season. I'd go in and pick out clothes.

Speaker 5 (26:59):
And coming out with like even baggy your jeans, and
my mom was like, oh my god, and I was
like I don't care, like I love baggy jeans, and
then I think about that myself in that moment, and
like if people didn't influence me, and like there weren't
all these like such high stakes, if I would have
just kept dressing that way, like the way I dressed
now today, sitting here, so that whole like detour, and

(27:24):
then like after so long, it's like how many times
can you get splintered off before you're like not even
a person anymore? And so I just was super fucking
hollow and empty and like couldn't get a fucking board sponsor,
Like nobody even gave a fuck about what I was doing,

(27:45):
and I'm like, like.

Speaker 4 (27:47):
What went wrong? Yeah? Uh? That was like in the
nine eight o nine.

Speaker 2 (27:55):
Leo, I remember when I met you, which was about
that era and nine.

Speaker 5 (27:59):
Yeah, there's no there's no paycheck happening. I worked a
full time job, yeah, for graphic designer.

Speaker 4 (28:04):
Yes, I did. I went to school that was things
at a lighting company.

Speaker 5 (28:08):
I mean, I I just remember being super young and
being like I don't know, I somehow had the wherewithal
to be like I'm going to need a fallback plan
in case skating doesn't work. Yeah, So I like, you know,
I loved going to school. My mom was like, are
you sure you don't want to do homeschooling like all
the other like fucking kids, your a's that are in
this whatever, they're all doing it.

Speaker 4 (28:28):
You have the option if you want. I'm like, no
fucking way. I liked stability.

Speaker 5 (28:32):
I like school, I like learning, and I really loved
a lot of my teachers. And I was like, yeah,
I want to do whatever something as like a fallback.
So I went to school for graphic design as soon
as I graduated high school, and then midway through my
college career, I had to cut it short and graduate

(28:52):
within associates because that's when shit really tanked for like
anybody who's like a non CIS male skater. So thankfully,
I I mean there was like I graduated and I
did my show or whatever, and then they had like
job placement and I just got at my first interview,

(29:13):
I got hired at that place.

Speaker 4 (29:15):
Yeah, and so then I worked there for I don't
know three years.

Speaker 2 (29:20):
Before but I remember Monday through Friday and then you
would go out and film on the weekends or sometimes
after work.

Speaker 4 (29:25):
But I just want to like.

Speaker 2 (29:26):
The context is so important here and I hate I
don't want to tell your story, but I want to
put in context here. You would work a forty hour
work week and yeah, there are pro skaters at work
and then film, but you were working and then doing
overtime for skateboarding filming, and then you'd be your part
would be on Thrasher and it would look like the
optics would look like you were a paid pro skater.
And like what I was trying to say about FLS

(29:46):
is like you were flow for Vans and for you
you got out to Chicago and tell the listeners of
that story to be able to get a ticket out there.

Speaker 4 (29:56):
This was the X Games one. Yeah, when you're this
was an X Games moment.

Speaker 2 (30:01):
And you're holding the trophy in the van shirt.

Speaker 4 (30:04):
That was X Games podium. Yeah, so okay.

Speaker 5 (30:08):
So then during that moment, I was like, okay, I
should probably like take another stab at it. So I
like quit my job and was doing freelance graphic design
to like make ends meet, and then like I had
somebody living with me to help me pay my rent.

Speaker 4 (30:20):
So it was like very frugal living.

Speaker 5 (30:22):
I shared my bed with this person, got some coaching.
I'm like, how do people like get paid in skating,
Like how the fuck? And so they're like, you have
to like make a pitch deck. I'm like, oh, okay,
so I like made a one pager. Oh fucking one pager.
Hate fucking industry, lingo, get fucked. Whatever was showing like

(30:43):
my stats, Instagram followers, accolades, projects, I'm working on whatever,
And then a potential agent was like, I don't want
to negotiate this deal for you because I don't want
to take ten percent of the nothing that the going
to give.

Speaker 4 (31:00):
Those were his exact words.

Speaker 5 (31:02):
So I like cast the net and I'm like, Vans,
I've been okay, I've been on the team forever, off
and on my whole life, but from nineteen to twenty four.
So that was like, I don't know, five years. I
don't know math I do if I think long about it.
But yeah, so I'm on Vans Flow five years. And
then they're like there's nothing. They're the nothing they're going

(31:24):
to give you, and I was like, not any nothing
like nothing, so so whatever I was like, I was like,
I don't know how I'm gonna get out to Austin
for the X Games. I guess I'll like ask Vans.
Maybe I was expecting them to say no, and then
they were like yeah, And I was.

Speaker 4 (31:37):
Like, whoa.

Speaker 2 (31:39):
Insane?

Speaker 5 (31:41):
I'm getting that flight paid for. I mean like back
in the day, it was like Bill o'bam would pay
for my flights.

Speaker 4 (31:45):
But they're like, hey, but you just gotta wear a
Van shirt while you're skating. Do me a favor and
wear a band shirt.

Speaker 5 (31:52):
Was like easy, of course, of course, no problem. I'm like,
what else can I do for free? Do you want
to split me in any other way?

Speaker 4 (32:01):
Go ahead? So you went to the mall, I bought
a shirt.

Speaker 2 (32:05):
You bought your shirt, and then what happened to that contest?

Speaker 5 (32:08):
Oh?

Speaker 4 (32:09):
I won? Yeah, I won that year and you were
holding or did I win our second place? Well?

Speaker 2 (32:12):
No, you won and you were holding the trophy. And
this is a big deal at that time for like
there was more visibility happening around women's skateboarding. You're on
the podium, you won the contest, You're wearing a Van shirt.
To me, it looks like you were entirely paid. And
so again like the optics of like what a male
counterpart was doing. They were paid to skate, and you're
like doing triple time, triple time to yeah, the best skateboarder.

(32:37):
I just like want to like again, I don't know,
it's just so important to understand how much, how many
laps around the sun you were doing just to stay afloat.

Speaker 5 (32:44):
Yeah, barely at that, But it's like, uh, yeah, people
like us have to work like three, four or five
times as hard to make a third of what a
guy would make any fucking whoever. Yeah, any run of

(33:05):
the mill of fucking skater gets probably what I make
as like.

Speaker 4 (33:09):
A top paid transskater or whatever the fuck.

Speaker 2 (33:12):
And it got better when you found your home at Nike.
But like, I think it was interesting. We were talking
about how everyone's kind of tried to tell your story
for you, and I was involved at Nike that time
and getting to tell your story for you again, which
was cool because I felt like I knew you. But
in retrospect, I'm like, man, who hasn't tried to tell
your story other than you?

Speaker 4 (33:29):
Yeah, yeah, I mean it was interesting.

Speaker 5 (33:31):
I mean, this will go back to the documentary too,
Like that was such a crazy era of my life
because it was just like Dark Knight of the Soul
like on film, Like I was like everything that I
ever thought, everything that worked for me, all the ways
I learned how to survive, none of it is real
for me, and so I'm gonna just take the leap.

Speaker 4 (33:54):
And like I.

Speaker 5 (33:55):
Figured, it's like when I cut my hair, then I'm
like not marketable and then I like lose on my sponsors,
while other more feminine counterparts in the industry keep their
contracts and they keep their paychecks and whatever because they're like, okay, well,
if we're gonna cut one of the like women get
rid of the dike.

Speaker 4 (34:14):
That was me.

Speaker 5 (34:15):
So I'm always boom. So I was like, if I
come out as trans like what the fuck, that's it.

Speaker 4 (34:19):
That's the end.

Speaker 5 (34:21):
Uh, Thankfully for me. At that time, it was like
marketable to be woke.

Speaker 4 (34:25):
So I squeaked in. Look I squeaked in.

Speaker 5 (34:28):
I got a contract, but like now it's not marketable
to be woke, and I'm just like, hmmm, I'm noticing
a pattern.

Speaker 4 (34:36):
It was a good era.

Speaker 2 (34:37):
I mean we all became employed in the skate industry
in that era in a meaningful way. Yeah, I got
to see to the table, You got to see the table.
You got a meaningful contract that wasn't just taking the crumbs.
It was like it was and promises for a signature show.

Speaker 5 (34:52):
Yeah thats raw that I really truly feel like I
squeaked in because I'm like, who's even getting pro shoes now?
Like it's all corporate, Like it's like if skater own
shoe brands, Like remember you say the Musca, the ar Sorry,
Like everyone had a fucking shoe back in the day,
like early two thousands the Americas, there was like the
Leo Romero that a Templeton's OK, and the Jury shoes,
Like everyone on the team had a shoe.

Speaker 4 (35:13):
Yeah, it was sick.

Speaker 5 (35:14):
Now it's like you're lucky to get a colorway. A
signature shoe is unfucking heard of. So I'm like, wow,
even if it's just for this moment, like I did
do it.

Speaker 2 (35:27):
It will never be forgotten.

Speaker 4 (35:29):
Oh thank god.

Speaker 5 (35:30):
It's so comfortable too. I know I made that a priority.
That was my number one. I'm like, why why would
we be uncomfortable.

Speaker 4 (35:37):
When we could be comfortable? Like the fuck?

Speaker 2 (35:39):
Yeah, I can't always love you in gear check and
like gear talk with you is super fun because you
like get down, Yeah, well what don't you obsess about?
And thank god you're there doing all the hard work
for us.

Speaker 4 (35:50):
Yeah, but like you were.

Speaker 2 (35:51):
Putting in every shoe, you would just spend so much
time skating it to really figure out the dues and
don'ts of what you do and don't like about it.
Then you would alter it. And you you're great seamstress.
I'll say, are you so you?

Speaker 4 (36:04):
Yeah?

Speaker 1 (36:04):
You know.

Speaker 2 (36:05):
I feel like you just know how to like make things.
You approach things with like a do it yourself. I'm
gonna make it work for me, and I'm going to
improve it, and so you're always like finding the problem
and building this solution. And then when I found out
you were getting your own shoe, I was like, oh,
this is going to be incredible, Like you're now working
with some of the best performance designers that can bring
your ideas the forefront of a shoe and I love
that like comfort and that was a big one, and like,

(36:28):
I don't know, you've skated so many shoes, Like what
about do you want everybody shoeing or should we just
we could?

Speaker 5 (36:34):
I mean I could also like and like the reason
why my fucking feet her so bad is because I
skated vans my whole life.

Speaker 4 (36:40):
Yeah, with my like the seams are like pressing up
whatever we don't know.

Speaker 5 (36:45):
Yeah, we don't have to do all that, but I
just wanted to be wid enough in the toe box
so that I.

Speaker 4 (36:49):
Didn't have a fucking foot pain when I'm skating. And
how hard is that?

Speaker 5 (36:53):
Why is every shoe so narrow? Why have you tried
to put a Janowski on?

Speaker 4 (36:58):
Try it? Yeah?

Speaker 5 (36:58):
I love you Janowski, but like that shoe, I like
it like fits a corn dog.

Speaker 2 (37:03):
So weird too, narrow white feet? Men have white feet
and skateboarders I think, I don't know, I can speak
for everyone's feet, but my feet are wide and like
so it's really interesting that the if you think back
to all the shoe eras a lot of them, it
went from wide to narrow, and then it went kind
of back to wide again, Like why are we binding
our feet?

Speaker 1 (37:21):
Leo, you're a really good designer. You are a seamstress.
You have had to alter your world to fit you
and getting to work on this brand with you, Taky,
can you tell me a little bit about why you're
making your own brand?

Speaker 4 (37:33):
Oh my god, yes, I certainly can.

Speaker 5 (37:36):
Yeah, that is a that's a recurring theme for me,
like whatever, like finding something that's like close but not
exactly right. And then going in on it and then
making it fit better, whether it's clothes or like a
fucking board sponsor.

Speaker 2 (37:56):
Uh.

Speaker 5 (37:56):
Just I've been in some pretty raunchy like just dirty
like vans on skate trips, Like it's like the fucking
booze and peeing and bottles and like just smoking in
the car and the windows are up, and it's like,
oh my god, like this is not this is if
I'm gonna be on a board company, Like this is

(38:17):
not the van that I want to be in.

Speaker 4 (38:19):
I want to be with people.

Speaker 5 (38:21):
That I don't know or like like I want to
be in the van with like you guys, we all do,
and like we're like consider it. And it's like there's
not like piss on the I don't know, but further,
you know, there's a after glue and all that ended.
It was like kind of a fork in the road
whether or not should I get a board sponsor or

(38:41):
should I start another new brand? And I really sat
with that and kind of let the my like let
it come to me. And my gut was like let's
do the brand because that way I can just have
an out like I like do all the art for it,
like everything from like art direction to like gruntworks like

(39:03):
all all me and Alex is the legs because she
does spreadsheets and other things that I cannot do, and
you do, Like how many times have I booked a
flight and it's the wrong day. I can't do it
with the numbers and shit. No, it's like it's shapes
for me, yeah, right in shapes and physics for me.

Speaker 4 (39:24):
Yeah. But yeah, so yeah with Tacky it's nice.

Speaker 5 (39:27):
And I also, like, you know, there's a lot of
stuff I learned on my own on the way, like
on my journey that I wish I knew when I
was eighteen, seventeen, sixteen, Like I'm like, could I'm like,
could you fucking imagine how unstoppable I'd be if I
learned about PT when I was sixteen?

Speaker 2 (39:46):
All of us.

Speaker 5 (39:47):
Fucking that whole from sixteen to twenty six just always
a rolled ankle.

Speaker 2 (39:52):
Could you imagine if I didn't have that issue?

Speaker 4 (39:55):
Whatever?

Speaker 5 (39:56):
So yeah, I'm trying to share that wealth of knowledge
with just whatever younger kids, the team on tacking and
whoever whoever wants the information. I'm like obsessed with giving it.
I'm like, you have to do this because it like
then you get to skate way longer and better and
stronger and like all the shit. So that and then
other just like industry stuff where I don't know, I

(40:17):
think that like I could like I could say, like
I wish there was somebody to guide me, but there
wasn't a person like me to be guided by. So
it's been a lot of trial and error and I
feel like, Okay, we're like out a place where I'm
like here's what I will do, and here's like what

(40:39):
I won't do. Yeah, and it's just I just like
have to walk into the fire. I don't know, I
just gotta try it and see. Like there's I don't know,
people don't know how to like managers, and I just
feel like, you know, I'm at this stage where i've
like like go of management and stuff. I just feel
like nobody really knows how to advocate for me except

(41:00):
for me. So that's right, I'm going to just take
a stab at it and like stop, you know. But
it's like it's the people are like, oh, you should
get a manager, but then then they're like how do
They're like market Leo Baker and they're like okay, hell,
and they're like, actually have no idea. It's a transperson.
We've never done that before, and I'm like, You'm like,
I'm the one that has to be like, this is
how to do it.

Speaker 2 (41:19):
Yeah, We're so lucky to have you in this timeline.
Though I've been like, I don't want to get too
emotional about this, but I admire you so much and
I've just watched you become the most beautiful person ever.
You always have sowe and handsome and handsome and talented,
and like, it sucks that you've had to go through
the industry and it's worse to know how to make

(41:40):
it better and to give people like the tutorial, like
thank god they're learning from you, and like the gifts
that you've given skateboarding and everything that's going to be
left behind and the things that you're still giving it.
It's just one of the kind thank you. I don't
want you to be so alone in it all.

Speaker 4 (41:58):
It's very lonely. It is only because I'm like, they say,
could I even whatever.

Speaker 5 (42:03):
I'm just like, I'm just gonna call Alex and be like,
you're making guess what you're.

Speaker 2 (42:06):
Making the but you're making the blueprint the blueprint in
real time, and we're all here to keep your map
with lights on it so you don't get too lost.
Thank you, And uh yeah, I think I make promises
that don't happen on this podcast all the time. But
I really do want to have you to come back.
I've even gotten into like.

Speaker 4 (42:24):
I feel like we just got started.

Speaker 2 (42:25):
We just got started. We haven't even talked about.

Speaker 4 (42:29):
How there's all kinds of stuff.

Speaker 2 (42:30):
Oh God, I want to know what you and your
therapists are talking about. I want to talk about real
talk on how you just moved through this world when
it gets hard, because it does, and then I don't
know whatever else we could go on for the next
Like you said, we might be here till tomorrow. You
said that at the top.

Speaker 4 (42:45):
Yeah, I'm like, oh, there's going to be a lot. Yeah,
it's like.

Speaker 2 (42:49):
Talk about what notifications are going on your phone right now?

Speaker 4 (42:53):
Well hopefully not.

Speaker 1 (42:55):
Thank you so much for joining us a lot. We
got to have you back again.

Speaker 2 (42:59):
All right, Leo, where can we find you?

Speaker 4 (43:02):
Okay? So my Instagram is Leo Underscore Baker.

Speaker 5 (43:06):
My skateboard company's instagram is at taki joy Factory all
one word and Tackijoyfactory dot com is the website where
you can please buy stuff from me music and then yeah,
I make music under the pseudonym Leo pop Star, which
if you search on your fucking phone you can find
it on whatever streaming platform that you used to listen

(43:29):
to music. Wherever you get your music, yeah, hopefully not
any place that has ice ads. Sorry if I just
ruined the whole take, but I just can't deal with it.

Speaker 2 (43:39):
It's like, what happened to fucking let's do Let's bring.

Speaker 5 (43:42):
Back CD players like on my CD on my webs
I don't know they're claiming the youth are doing that,
they're bringing back I'm just sick the phone.

Speaker 4 (43:50):
Yeah, everything is in the fucking screen.

Speaker 5 (43:53):
It makes me The Internet is one insane sometimes but whatever, Okay.

Speaker 2 (43:58):
Yeah, and you're on good luck with that. We named
it that because we could have named it a skateboarding one.
But I swear to God how many times we've heard
through luck with that throughout our lives.

Speaker 4 (44:07):
I will to know.

Speaker 2 (44:10):
What you might need some luck with. Right now.

Speaker 4 (44:12):
I need a lot of luck with switch trays.

Speaker 5 (44:14):
I mean, I am putting in the hours, but God,
I am not getting the return.

Speaker 2 (44:18):
I want to know. Are you just letting it happen, like,
just let it happen like sometimes like.

Speaker 4 (44:23):
I yes, ish, yes, ish, Okay, we'll have to talk
about it. I'm almost there. Okay, I'm getting there.

Speaker 5 (44:32):
Okay, my first like my first try out, the gate
used to be just like chaos. Now it's like, okay,
there's some structure happening, and I'm just figuring out like
the whole.

Speaker 2 (44:42):
What's the last part of it that you unlocked?

Speaker 5 (44:45):
Just consistency and flipping it correctly, but it still goes
behind me, and then it's I still don't land it
or it doesn't flip.

Speaker 2 (44:53):
All the way, so it's scooped and it's flipped. It's
just where it needs to like it's over there though, okay,
and it needs to be right here. Okay, all right,
So we want you to try.

Speaker 4 (45:02):
Yeah, I'm working. I will put in the time. It
will come. Well, it might be ten years, it might
be next year, it might be next month.

Speaker 2 (45:10):
And one thing we do know is it will be
perfect when you're ready to show us. Thank you for that,
of course, Well, thank you so much for joining us today.
We are beyond lucky. I mean I mean it, thank
you sincerely, like so stoked to have you here. It's
been a long run.

Speaker 4 (45:24):
Yeah, well that's it.

Speaker 1 (45:26):
That's our show for today.

Speaker 2 (45:27):
Yeah, listeners, tune back in. You can find us on
at good Luck pod write, subscribe, like, don't like, do
whatever you need to do, but tell us if you're
out there. We'd love to hear from you. That does it.
We'll be here next week.

Speaker 3 (45:41):
Good Luck with That is an iHeart women's sports production
in partnership with Deep Blue Sports and Entertainment.

Speaker 2 (45:48):
We are your.

Speaker 3 (45:48):
Hosts Ashley Rayfeld, Nora of Bas Gonzlos, Alex White, and
Mimi Neu. Our executive producer is Jesse Katz, supervising producer
Tari Harrison, video producer Daniel Goodman, and video production by
School of Humans.

Speaker 1 (46:02):
This podcast was created by Ashley Rayfeld.

Speaker 3 (46:05):
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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