The Problem with Snowboarders with Olympian Scotty James

Summary

Podcast Summary

Dear Chelsea – "The Problem with Snowboarders with Olympian Scotty James"

Host: Chelsea Handler
Co-host: Kathryn Law
Guest: Scotty James, Olympic Snowboarder
Date: February 5, 2026

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Episode Overview

This episode of "Dear Chelsea" features Chelsea Handler and Kathryn Law in conversation with world champion and Olympic snowboarder Scotty James. The discussion blends Chelsea’s trademark comedic tone with honest advice, deep dives into Scotty’s Olympic journey, spirited debate about snowboarders and skiers, and live listener questions covering relationships, self-esteem, and social dynamics—all delivered with a lively, irreverent spirit.

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Main Topics & Key Discussion Points

1. Chelsea’s Recent Adventures (03:32)

• Chelsea shares tales of her Vegas residency, a successful gambling streak, a near-missed flight, and a travel mishap which was saved by a kind stranger.
• Notable Quote:
  "Who pays attention to other people’s luggage? Like, I don’t pay attention to who’s putting what in the overhead bin."
  —Chelsea Handler (05:10)

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2. Celebrity Gossip Warmup (05:52)

• The hosts chat about pop culture headlines: Beckham family drama and leaked Blake Lively / Taylor Swift texts.

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3. Introducing Scotty James: Olympic Snowboarder (07:18)

• Kathryn sets up Scotty’s impressive resume and new Netflix documentary “Pipe Dream.”
• Chelsea congratulates him on his latest win and probes into his Olympic mindset.

Training & Dealing with Pressure

• Scotty describes handling both self-imposed and external pressures, especially representing one's country:

  "There’s always the pressure you put on yourself, but then, you know, there’s all this exterior pressure that people put on you...But it’s my fifth go around now, so from the pressure perspective...I feel a little bit more vintage, which is a good thing."
  —Scotty James (09:10)

Pre-Competition Rituals

• Scotty isn’t superstitious but always wears red gloves during events—a tradition born of a lucky X Games victory.

  "I saw these red gloves, which a brand had sent me. Anyway, I put the gloves on and I felt like I was coming out to fight a bit that week...Ever since then, it's been my thing."
  —Scotty James (10:51)

Snowboarder vs. Skier Debate

• Chelsea lightheartedly blames snowboarders for her slope mishaps, prompting a spirited back-and-forth:

  "The only two times I’ve been hit on a ski mountain are by snowboarders."
  —Chelsea Handler (08:29)
  "I think it’s more so the skiers have the problem with the snowboarders, not the other way around...We’re just cooler."
  —Scotty James (23:31, 24:56)

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4. Scotty’s Early Life & Career (14:12)

• Grew up near Melbourne in Warrandyte, not the typical Aussie beach town.
• Started on skis at age 3 before switching to snowboarding; family trips to Canadian mountains.
• Describes the importance of parental support and commitment in a young athlete’s journey.

  "They had to kind of realize that dream for me...They had to create the pathway for me from when I was seven or eight years old."
  —Scotty James (16:07)

Responsibility & Early Success

• Left home at age 12 to pursue snowboarding professionally; first Olympics at 15.
• The emotional impact on family and the subject of his new documentary.

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5. Physiology, Growth & Competition (18:06)

• Kathryn asks about growing tall as a snowboarder (6’2”), the challenges of center of gravity on the halfpipe, and the pros and cons.

  "Sometimes I feel a little bit like Bambi. Like my limbs are flying every direction and I’m trying to pull them back in."
  —Scotty James (18:23)

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6. Personal Life & Balancing Relationships (19:38)

• Married to Chloe, daughter of the Aston Martin heiress—she’s the “CEO of Scotty James.”
• Shared the story of their meeting and disarming her family’s skepticism of snowboarders with his accent, humor, and wine.

Parenthood

• Has a one-year-old son, Leo, yet to be introduced to the slopes.

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7. The Skiers vs. Snowboarders Culture Clash (23:01)

• Chelsea pushes for clarity about the tension. Scotty says it’s largely manufactured and maintains snowboarders are just “cooler.”
• Discussed etiquette and the few ski areas in America that still exclude snowboarders, like Deer Valley.

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8. The Solitary Nature of Mountain Sports (28:54)

• Addresses how snowboarding demands self-reliance, with a team made up of family and close supporters more than fellow athletes.

  "You have to be okay with being alone, be okay with being extremely selfish about what your endeavors are...My team is more so, you know, my family, other people that have helped me in my journey."
  —Scotty James (29:23)

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9. Documentary “Pipe Dream” (31:39)

• Discussing the emotional process of making a documentary about his life and career, reflecting on hardship, family sacrifice, and hearing for the first time how his parents and siblings felt about his early departure.

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10. Mental Game & Preparation (33:27)

• On overcoming setbacks during competition:

  "Honestly, I reflect on… I just say, fuck it. Let’s just go get it done."
  —Scotty James (33:51)

• Age and experience make it easier to stay present under pressure.

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11. Listener Advice Segment

a. Learning to Ski Later in Life (44:35)

• Caller wants to know if it’s too late to start skiing seriously at 31; Chelsea says absolutely not, emphasizing practice, good instruction, and trading fearlessness for competency.

  "What you lose in fearlessness, you gain in competency and capability."
  —Chelsea Handler (45:42)

b. Ski Self-Esteem & Relationship Pressures (47:00)

• Jess from Vancouver, married to a ski instructor, feels excluded by her husband’s insular, critical ski tribe and is losing her love for the sport.
• Both Chelsea and Scotty recommend finding a less judgmental or more diverse group to ski with, and establishing boundaries.

  "Nobody wants to talk about technique all the time...Just change the channel."
  —Chelsea Handler (48:44, 49:28) "It doesn’t matter your level. I have that same feeling in my world sometimes...If people have a go at you about not being on their level—who gives a shit? It doesn’t matter at all."
  —Scotty James (50:13–51:22)

• Scotty jokes he could welcome her "to the snowboarding side" and emphasizes fun over ego.

c. Financial Disparity in New Relationships (55:05)

• Rebecca, who moved to a Greek island to pursue her dream, is dating a much wealthier man and asks when or how to have “the money talk.”

• Chelsea recommends clarity, honesty, and collaborative compromise early on, without making it dire or expecting him to pay for everything.

  "I think you should just bring a lightness to this conversation and be like, listen, I am excited about all of this potential...But I just really want to be transparent."
  —Chelsea Handler (58:34)

• Scotty, noting by analogy his own marriage to an “heiress,” adds:

  "Congrats on having the courage to move, try something different. I think that takes a lot of courage, so respect for doing that."
  —Scotty James (60:15)

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12. Final Rapid-fire Q&A with Scotty (64:57)

• Time on the mountain: yes, with family, but not much outside training/competition.
• Favorite pre-competition meal: Spaghetti Bolognese (night before).
• Family’s support: will be present at the Milan Olympics, a welcome change after China’s closed-door Games.
• Chelsea teases a bet to go snowboarding with Scotty if he brings home gold.

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Notable Quotes & Memorable Moments

• On superstitions:

  "How do superstitions maintain when they don’t work a lot of the time?"
  —Chelsea Handler (11:29)

• On athletes and reflection:

  "You really have to take note of where you began and how far you’ve come...You’re the one who got yourself all the way here."
  —Chelsea Handler (37:24)

• On courage and success:

  "I think everyone...we all have passions, we all have something that we want to realize in our lives. And I feel very fortunate I had the courage to actually continue and go for it."
  —Scotty James (38:13)

• On social dynamics in mountain sports:

  "If you don’t fit that mold, you don’t really feel like you’re a part of what they’re doing...find a bit of sanity in that you actually enjoy it."
  —Scotty James (50:13–51:22)

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Memorable Segments & Timestamps

• [07:52] Meet Scotty James & Olympic Season Check-in
• [10:19] Pre-competition rituals and red gloves backstory
• [14:12] Childhood, upbringing, and chasing winter across the globe
• [16:07] Parental influence and the leap to professional snowboarding
• [19:38] Marriage, in-laws’ skepticism, and using the accent card
• [23:31] Skiers vs. snowboarders cultural debate
• [28:54] Solitude in snowboarding vs. team sports
• [31:42] “Pipe Dream” documentary—emotional family revelations
• [33:51] “Just say, fuck it”—the mental reset in competition
• [44:35] Advice: Is it too late to become a good skier?
• [47:00] Advice: Ski self-esteem & marriage to a ski instructor
• [55:05] Advice: New relationship and disparate finances
• [64:57] Q&A: Off-duty mountain time, family, favorite meal pre-competition

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Tone & Style

The episode provides an engaging mix of humor, candor, and practical advice. Chelsea’s irreverent takes, Scotty’s humility and honesty, and Kathryn’s facilitation keep the energy light and accessible, whether discussing the Olympics or relationship boundaries.

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TL;DR Takeaways

• Scotty James opens up about five Olympics, pressure, rituals (red gloves!), and the snowboarder identity—balancing grit with humor and humility.
• Listeners receive frank, supportive advice—whether learning to ski late in life, managing self-image in competitive scenes, or navigating financial disparities in love.
• The skier-vs-snowboarder “feud” is more about attitude and culture than any real animosity, with everyone ultimately encouraged to do what brings them joy on the mountain.

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Listen For

• Tales of Olympic-level discipline and family sacrifice
• Chelsea’s comedic but actionable advice for real-life problems
• A rare peek at the softer, reflective side of a world-class athlete
• Tips for thriving in sports, relationships, and navigating social insecurities—with a healthy dose of wit

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For full episodes and more advice, find "Dear Chelsea" on your favorite podcast platform or YouTube: search 'Dear Chelsea Pod.'

Transcript

[Chelsea Handler]

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[Kathryn Law]

60% off your first box.

[Chelsea Handler]

Okay guys, the High and Mighty Tour is about to begin. Tour starts on February 13th. Everybody D.C. i will see you there. To jump things off, February 14th, Atlantic City, which I just added. Madison, Wisconsin. Milwaukee, Wisconsin. Detroit, Michigan. Cle. Cleveland, Columbus and Cincinnati, Ohio. Denver, Colorado. Portland, Maine. Providence, Rhode Island. Springfield, Massachusetts. April 3rd, which is in Rohnert Park, California. That has just been added. Chicago, of course. Indianapolis, Indiana. Louisville, Kentucky. Albuquerque, Mesa, Arizona. Kansas City, Missouri. St. Louis, Missouri. Minneapolis, Minnesota. Nashville, Tennessee. Charlotte, North Carolina. Durham, North Carolina. May 6th, I'm doing Netflix as a joke festival. I will be in Los Angeles. That is a new announcement. Saratoga, California. Monterey, California. Modesto, California. And Port Chester, New York. Boston, Massachusetts. Portland, Oregon, and Seattle, Washington. I will be touring from February through June. Go to chelseahandler.com for tickets if you want to come see me perform. I will be on the High and Mighty Tour. Hi, Katherine.

[Kathryn Law]

Hi, Chelsea. How's it going?

[Chelsea Handler]

Well, I'm still recovering from Vegas. I had a real quick turnaround. I did one of my shows this weekend for my residency. I had a lot of people come, a lot of friends. We went to dinner, then we went to my show. Really fun. Working on all my new material for my new tour.

[Scottie James]

Oh, nice.

[Chelsea Handler]

And then we went and gambled. I won $3,500. I mean, I'm unstoppable, basically. I've also. I'm betting on the super bowl, so that's good.

[Scottie James]

Oh, good.

[Kathryn Law]

Oh, she's a sports betting girly.

[Chelsea Handler]

Yeah, I'm betting with sports. Yeah, me and my new friend are betting a lot. He's a gambler. So I've just decided to join his gambling addiction. And I'm into it.

[Kathryn Law]

As long as you keep winning, it's great.

[Chelsea Handler]

But I had a 6am flight out of Vegas. So I got home at 1:30 and then at 4:30 I was like, guys, I don't know that I'm gonna make this flight. I said to my assistants, I'm like, you guys, so, you know, have a backup one. But I don't like spending the day in Vegas. And the next direct flight back to Vancouver was at 4:45. So I went to bed at 1:30, woke up at 4:30 to make my 6:30 flight. 6:15 flight out of Vegas to Vancouver. I was drunk at the airport. I was a mess. I got to Vancouver. I spent the entire time looking at ridiculous videos of the people. That trend where people call their parents and say the police are coming following them back to their house because they told them their parents had fallen so that when they get home to their house, their parents have to be on the ground acting like they fell down. The stairs. I mean, I was laughing so hard on the flight. I was so delirious. I finally sobered up. I got to Vancouver. I get off the plane, and I forget I had a tote bag because Carlos brings all my stuff from la, so I don't have to travel with a lot. But I forgot my tote bag, which had my computer, like, all my stuff. I left it in the overhead bin. Just completely forgot I had even had bags. Walked all the way to customs, and this woman is like, miss, Miss, you left your bag in the overhead bin. And she was another passenger. And I'm like, God, who ever pays attention? And she didn't recognize me because she didn't say Ms. Handler or Chelsea. She didn't. She was just like, miss, I brought this for you. You left. And I'm like, oh, my God. I'm like, who pays attention to other people's luggage? Like, I don't pay attention to who's putting what in the overhead bin. It was so.

[Kathryn Law]

That is really sweet.

[Chelsea Handler]

I'm like, thank you so much. I mean, it was.

[Scottie James]

Yeah, that was.

[Kathryn Law]

It restores your faith in humanity.

[Chelsea Handler]

I know, I know, I know. I'm a lucky girl.

[Scottie James]

Yeah.

[Kathryn Law]

Okay. I do have to ask you, what do you think about all this Beckham drama? Are you keeping up on this a.

[Chelsea Handler]

Little bit about Victoria Beckham and the dog kids? I mean, I don't really know anything about them, but it tracks from what I do know.

[Scottie James]

It does.

[Chelsea Handler]

It sounds plausible.

[Kathryn Law]

I feel like there's probably bad behavior on both sides, but I. I feel like the big red flag is that the, like, son and daughter in law just had, like, they renewed their vows already. Like, they had a vow renewal. I'm like, when you have to do that a year or two in. Yeah, I think it's curtains.

[Chelsea Handler]

Yeah.

[Kathryn Law]

It's a bad sign, I think.

[Chelsea Handler]

Yeah, you're probably right about that.

[Kathryn Law]

Yeah.

[Chelsea Handler]

I don't know. I don't know. I don't find that much interest in that story. But, I mean, yeah, it's kind of.

[Kathryn Law]

I just like people airing their dirty laundry. That I find.

[Chelsea Handler]

What about the Blake Lively and Taylor Swift messages and all the. Not even. First of all, Taylor Swift comes out looking awesome once again, of course. And Blake Lively and Ryan Reynolds, like, oh, my God, So embarrassing to have all of those things. Text and voice memos released. It's so embarrassing.

[Kathryn Law]

Oh, my gosh. Can you imagine, like, every random thing you texted your friend?

[Chelsea Handler]

No way.

[Kathryn Law]

I know.

[Scottie James]

Way.

[Chelsea Handler]

That is just like, stop it. Those two must be, like, under a curtain somewhere and, like, stop. Make this go away.

[Kathryn Law]

They didn't get the Oprah advice of, like, imagine I'm not on the front page of the New York Times. Like, whatever you're sending in a text.

[Chelsea Handler]

Or think about that. When I text people anything, I'm like, just imagine this is going to be public at some point, because it probably will.

[Kathryn Law]

Well, our guest today is going to the Olympics.

[Chelsea Handler]

I know. Yes, you guys, the Olympics are happening. Today's guest is a world champion, an Olympic. He's so funny, too. And an Olympic snowboarder, entrepreneur, philanthropist. He's won two Olympic medals, 10x game medals, five world half pipe championship gold medals, and he's headed to try and snag the gold this month at the Olympics in Milan, Cortina. His new documentary is called Pipe Dream. It's on Netflix now. So please welcome Scottie James. Scotty James, welcome to. Dear Chelsea. Hi.

[Scottie James]

Hi. Thank you for having me.

[Chelsea Handler]

Thanks for taking the time to catch up during your season with the Olympics about to happen. You're having an incredible season. I know. You just won again in Switzerland, so congrats on that. How are you feeling?

[Scottie James]

I'm feeling good. Look, we needed to catch up Chelsea before the Olympics. You know, we're approaching closely, so I just needed your insight before we head over to Italy. But so far, the season's been. Been great. But, no, I'm feeling really good. And, yeah, naturally, obviously getting a win under the belt this time of year is a good confidence boost. So, yeah, looking forward to the. The rest of the season.

[Chelsea Handler]

I want to know all of it. I want to know how you. What your process is, how you maintain what you do before you race. I mean, listen, you're favored to win gold at the Olympics this year, so no pressure. You are a snowboarder, so I take issue with that because we're going to have to discuss that etiquette as well. The only two times I've been hit on a ski mountain are by snowboarders. Two snowboarders. And one happened the other day, too. But first of all. Okay, let's talk gold at the Olympics in Milan, Cortina. So tell me how you're feeling about it, how you look at things like this. What do you do with the pressure that is put upon you by being so good at what you do.

[Scottie James]

Yeah, I mean, naturally, coming into this Games, it's, you know, you feel that pressure. I think there's always the pressure you put on yourself, but then, you know, there's all this exterior pressure that people put on you to want to. They want you to show up and deliver maybe the result that they expect. And that's from the fans to your country that you're representing. And I think, most importantly, more so myself. I think I do go into every event with the intent to want to do my best and put my best foot forward to win. And that's the approach with the Games. But, yeah, I mean, when you're out there wearing your country colors and you're flat flying the flag and there's obviously a lot more attention, you know, you feel that pressure a bit more. But, I mean, it's my fifth go around now, so from the pressure perspective, but also experience, I feel a little bit more vintage, which is a good thing, I think, in this case. So I'm. Yeah, no, to be honest, I'm really excited. I feel like I've had a great preparation and the lead up's been awesome, so I just have to focus on the important things like fundamentals and making sure that I'm prepared from a. From a practical standpoint, snowboarding. And the rest will. Will do what it will do and.

[Chelsea Handler]

What happens the day of. What happens the day of a big competition. Like, are you superstitious? What is your regimen? What is your ritual?

[Scottie James]

I don't have too many rituals that I necessarily do before the event, but I always wear my red gloves in the event, so I guess that's a ritual. It's something that I always have. I listen to a lot of music, actually, when I'm training and competing as well. No specific artist, just depends how I'm feeling on the day.

[Chelsea Handler]

Just elevator music. Wait, what's with the red gloves? Where did those come from? Is that to remind people that you're a redhead?

[Scottie James]

Exactly. Yeah. Yeah. Just because, you know, I got so much equipment on, you know, it's hard to see the red hair sometimes. But no, I. In 2017, I want to say I won my first X Games gold medal, and I'd come from another event in Switzerland, and I saw these red gloves, which a brand at the time had sent me. And anyway, I put the gloves on and I felt like I was coming out to fight a bit that week. A bit of strength and adversity, and I won the event, and it was obviously a huge marquee event for us. And ever since then, it's been my thing. I always wear my red gloves, so it's been a fun little narrative.

[Chelsea Handler]

Oh, I like that. There was just a gambling movie that I watched with Colin Farrell where he wore gloves While he gambled, but he lost all the time. And I'm like, how do superstitions maintain when they don't work a lot of the time? You know what I mean? When people are like, I've got to do it this way. I've got to do. And it's like, it's not working for you, so stop doing that.

[Scottie James]

He doesn't have the right gloves, obviously.

[Chelsea Handler]

No, no.

[Scottie James]

Call in some of the red ones. Yeah.

[Chelsea Handler]

How many pairs of red gloves do you have, by the way?

[Scottie James]

Many, many, many. Well, we make our own gloves. We sell them. But, you know, I also have. I mean, through a season, I actually don't use that many. Like, one pair. They're pretty durable and good. But, yeah, in a season, I try and keep one pair because when I wear one pair, it's a bit superstitious. Like, I'm like, I gotta keep wearing, particularly if it's a good season. So.

[Chelsea Handler]

Yeah, and so I know you're friends with Shaun White. You guys are buddies, right? You competed a lot together, and now you've. You've surpassed him. I mean, you're greatest snowboarder of all time as we sit here today. So how does that impact your relationship? Because I know how insecure he is. Just kidding. I do know how insecure he is, but we all are.

[Scottie James]

We all are. That's very true. Well, if you look hard enough, everyone's got one.

[Chelsea Handler]

That's right.

[Scottie James]

I think we have a good relationship, actually. I think naturally evolved over time because, you know, I was a little kid, put him on a pedestal, and, you know, he's a hero and. Yeah, naturally, you know, with respect to Sean, he's one of the greats in my discipline. Always looked up to him and. Yeah, from when I was a kid to watching, to, I guess, to try and emulate the kind of success he had in the career, and then being able to do that in my own way, and then us building a relationship on the mountain, obviously, your competitors, we both wore our heart on our sleeves, so at times there's tension to. Then him retiring, and now, you know, we text and we have a good relationship. So, yeah, it's been a fun journey, I guess, to say the least. But I have a lot of respect for him. I think he's been amazing on the hill.

[Chelsea Handler]

I want to know more about what you guys do when you. What do you do when you. When you win. How do you celebrate? Because I was talking to Mikaela Shifrin and she just, like, found out about champagne a year ago, and I'm like, sister, what is the point of winning all of these, Being on all these podiums and winning all of these races if you don't know how to celebrate? She's like, it just never occurred to us. She's like, I didn't even know. And then once, I think she celebrated once, she's like, oh, wait, wait, wait. This is actually a really good time. We should do this more often.

[Scottie James]

Well, unlike Michaela, Shifrin and Chelsea, you'd be very proud of me. I discovered the champagne celebrations a little while ago, so.

[Chelsea Handler]

Well, you're Australian, so I do believe you. I do believe you. The only people who drink more than Americans are Australians, so I get it.

[Scottie James]

Exactly.

[Chelsea Handler]

Where did you grow up in Australia?

[Scottie James]

I grew up in a little town about 45 minutes out of Melbourne, the city called Warrandyte. So it's a tongue twister. You can try and say it. Warrandyte.

[Chelsea Handler]

Warrandyte. Okay. I tried it and it worked. So successful. Huge six. Let me get a bottle of champagne. Hold on one second.

[Scottie James]

You're allowed into enter our local pub. It's like, you know, it's the rite of passage, if you can say Warren Buck. So, yeah, no little town. And my. My family still live there, and I've got a house not far from there. So. Yeah.

[Chelsea Handler]

And so how does one get into snowboarding? I know a lot. I know a lot of skiing happens in Australia. People come over here. I live. I'm in Whistler, Canada, right now, and where. This mountain is filled with Aussies. So how did you start? And, like, what. At what age? You're like three years old, right?

[Scottie James]

Yeah, I was really young when I started. I don't even remember the first day. The first day I went on the hill. First time. I kind of remember snowboarding. I would have been probably 7 or 8 years old, maybe 10. But I'd started, yeah, when I was 3. At least. I was on skis, I think, for a little bit, which is a bit controversial, but then transferred over to snowboarding. Yeah, we. I mean, in Australia, we do have mountains. We have snowy mountains. You know, my local resort in Australia is Threadbow, so we. We just don't have a long season, so we were always having to travel overseas. I actually spent a lot of time In Canada and B.C. we used to go to a mountain called Big White. I went to Whistler. Yeah, we loved it over there. So my family weren't your typical Aussie family, playing tennis or going to the beach or doing those summer sports that most Australians do. We Were chasing the winter, so it was fun.

[Chelsea Handler]

And so at what age did you go, okay, this is gonna be. I wanna know how something like this happens when you start so early. Like, what percentage parents encouragement was it? What percentage passion was it? Like, what's the ratio of how things started to get serious for you in this sport?

[Scottie James]

I would say, I think others made that decision for me because, you know, so young, you don't really snowboarding. Such a young demographic we have, you know, I'm now 31 and I'm competing against 18 year olds. And even before that, if you're, you know, extraordinary talent, you're 16 and you know you're competing with the men. So it's, you do have to start young and get good young. So, so you can start to propel yourself into the career. So I really don't think I realized that it was a professional career or something that I would comprehend until I was about 13 or 12 or 13 years old. But before that, you know, even now speaking to my parents, they had to kind of realize that dream for me. It is something that I obviously wanted to do, but they had to create the pathway for me from when I was, you know, seven or eight years old. Obviously I had no awareness of that. I was just up on the mountain enjoying what I was doing and having fun. And I still do that. But they were, you know, creating that avenue for me if it's something that I really wanted to do down the line. So that point would have been, I would say 12, 11 or 12 years old was when I was like, okay, I want to take that leap into realizing this as a potential profession because.

[Chelsea Handler]

You'Re one of, you're the youngest of four kids. Yeah.

[Scottie James]

Yeah.

[Chelsea Handler]

And so were you the only one in your family that got that passionate about sport?

[Scottie James]

Yeah, youngest in my family of four. The most spoiled one, apparently the most.

[Chelsea Handler]

Me too. I'm the youngest of six and it's the best position to be in. The youngest is the best.

[Scottie James]

I mean, Chelsea, look at us, we're the best. I mean, it just is what it is, you know. But no, I think it was 10 or 11. I propelled myself into it.

[Kathryn Law]

I have a question about, like, as your body is changing when you're starting that young, I know you're pretty tall for a snowboarder. Like you're starting with one center of gravity and, you know, growing into a very different shaped human. What was that like? And were there struggles with that?

[Scottie James]

Absolutely, yeah. I would, I, I would say I'm a very differently shaped human. Up there on the mountain, did you.

[Chelsea Handler]

Try to stunt your growth so it could be a little bit more operational for you? I guess it's not really having that much of an impact for. So if you were shorter, who knows if you'd be able to accomplish all of these things?

[Scottie James]

Yeah, I mean, it might have helped. And maybe my parents looked into that. They're like, oh, boy, how are we going to stop this growth thing from happening? But no, it's. Yeah, I mean, a lot of my competitors are 5, 4, 5, 3, 6 foot 2. So it's a. It's a significant difference. And where that can be challenging is without getting into too much snowboarding lingo, the half pipe, the wall's 22 foot high. And typically, when you're riding up the wall, you're hitting a lot of G force. So when you have a lower center of gravity, you naturally don't have as much force pulling you down into the ground. And you can kind of just. You're just a little bit more in control. You have a bit more awareness of your, you know, your surroundings. And for me, sometimes I feel a little bit like Bambi. Like my limbs are flying every direction and I'm trying to pull them back in. So I'm compact like the other guys, but, you know, I'm naturally. I also have some benefits, whereas I'm a bit heavier. So when it's snowing, you know, we're in a unpredictable profession where it snows, there's wind. There's a lot of variables in those conditions. I'm a bit heavier, so I can carry more speed. Amplitude is a big criteria in our sport, so it can be also beneficial. So I like to focus on the. The positives, I guess, but it is a very, you know, big difference.

[Chelsea Handler]

Yeah. Yeah. And you're married to. Your wife. Says she's. The wife's name is Chloe. She says she's the CEO of your life. She's an heiress to the Aston Martin fortune. So you're basically a kept man by your wife. So how does that feel as a professional athlete?

[Scottie James]

Yep. She's the CEO of Scotty James, as she says, and she keeps the trains on the tracks.

[Chelsea Handler]

Yeah. How did you lock that down, Scotty?

[Scottie James]

Well, I mean, should we go down the whole. The whole story? She always says I don't tell the story in detail, but today I can make the exception of doing that.

[Chelsea Handler]

Absolutely. We have a lot of female listeners, so they definitely want the details, so.

[Kathryn Law]

Yeah.

[Scottie James]

Gotcha. Okay. Well, I. I explained it in my wedding speeches, me being Carrie Bradshaw from Sex and the City. And I was in New York City, walking down one of the streets in New York, and I was thinking, you know, maybe tonight's the night my love story's about to begin. I was playing that, that audio in my head. Walked to a restaurant called Motel Morris in New York City. It's on the corner of, I want to say 7th and 18th, but I could be wrong. We got to the restaurant, I met Chloe. I knew her brother, actually, before I met Chloe. Connected us. And sure enough, here we are, married with a little, little guy as well and still friends with her brother.

[Chelsea Handler]

So, so what was your, what was your move? What did you say to her? When did you know that you liked her? And then how did you follow up on it?

[Scottie James]

I mean, I think initially she was probably a bit skeptical. Had a very similar experience as yourself with snowboarders. Her dad, frankly, didn't like the idea of a snowboarder. Apparently when she was younger, she was also run over by a snowboarder. So off to a bad start before I even walked into the restaurant. So approval from dad was like, big. No, no. Snowboarder. Naturally, over time, the accent played a bit of a role. And, you know, we both shared a couple bottles of wine. And that helps.

[Chelsea Handler]

Yes, yes, yes. Okay, that does help. The accent also helps. For some reason, Americans are just like, she's American, right?

[Scottie James]

Canadian.

[Chelsea Handler]

Canadian. Well, same thing. Well, actually not now, but usually it's the same thing. But yes, yes, we are suckers for accents. It doesn't really matter which one. Any will do.

[Scottie James]

Yes.

[Chelsea Handler]

We just love an accent. So that gets you, that gets you further for sure.

[Scottie James]

Hopefully in some cases. Yes.

[Chelsea Handler]

Yeah. And now you guys have a kid. You have a one year old.

[Scottie James]

Yeah, Little Leo. He's one in a, in a few months now. I told myself I'm not going to be the dad that says like, says it by the months. I'm like, he's one in three months. I'm not, I'm not going to be like a. He's a 20 month.

[Chelsea Handler]

No, I'm with you.

[Scottie James]

It's too confusing. Just he's one year and a bit. That's where he's at at the moment.

[Chelsea Handler]

Yeah, exactly, exactly. People who talk in months. I once had somebody talk to me and tell me that her child was 72 months. I was like, what? I was like, is that five? What are you talking about? Do you mean five? I mean, I don't even know what 72 months is, but it's long and I don't have time for that. Has your son hit the slopes yet? Have you put him on a snowboard yet?

[Scottie James]

Not yet, no. No. I went up on the hill, and I put him in a backpack, and we went riding, which was really fun, but I haven't got him on the board yet. A lot of people ask me that question. But we'll see when the time's right, he can give it a go.

[Chelsea Handler]

Absolutely. Okay, let's move on to snowboarding. And why it's. What is the. What is the problem when you are not a professional athlete like yourself? I want to know, and I don't want to shame snowboarders. I'm dating somebody who snowboards right now. I'm trying to transition him to skiing, but I don't know. That could be a bigger commitment. But what is the issue between skiers and snowboarders? And where does it come from? And are there different. Two different sets of etiquette or one set of etiquette?

[Scottie James]

I mean, I think. I think it's more so the skiers have the problem with the snowboarders, not the other way around. I mean, it's just. It's the history and.

[Chelsea Handler]

But why is there such tension? Why? Why? It's like England and Ireland. Why are. Why do you. You don't think snowboarders care about skiers? They don't have a problem. They wouldn't want a snowboard only mountain.

[Scottie James]

Yeah. I don't know what the. What the gripe is between the two. I don't have an agenda. I'm like, if you like the mountains and you have as much fun as I do, go ahead. But, you know, maybe snowboarders, in this case, where you're getting run over and, you know, Chloe's been run over in the past, just not building a great strong case for us. There's also mountains still in the US where you're not allowed to snowboard. So. Yeah, I actually, funnily enough, went and stayed at a hotel at one of those mountains before, and it was quite a strange experience, fighting with not going out on the hill but staying in the hotel. It felt like I was really in the wrong territory. Where were you?

[Chelsea Handler]

At Deer Valley? Are you talking about Deer Valley?

[Scottie James]

Yeah, I was there.

[Chelsea Handler]

Yeah. Yeah, I know. I love it there because there are no snowboarders. I mean, I want us to get along. I do. I just don't understand. It's like. It's like a different ilk. It's like they just come and it's so rough, and then you hear them and you can't see them. But it's not the behavior of the snowboard, obviously. It's the behavior of the snowboarder. There's just a more of a.

[Scottie James]

We're just cooler. We're just cooler.

[Chelsea Handler]

I know.

[Scottie James]

You guys think we have more swagger. No, Then we don't think it. It's just that we can talk about facts. I mean, it's important to get factual on the show. You know, we're more comfortable. We walk around, like, in shoes. You know, we could wake up, roll out of our bed. It's like slippers, and I could wear those until I go to bed at night. I just also think that skiers are a little bit upset, and they're just like. They're just angry that they can't do that.

[Chelsea Handler]

Here we go. Here it comes. I don't think we have a problem with skiers. And now he unleashes. Unleashes this vitriol. How old were you when you went to your first Olympics?

[Scottie James]

First olympics, I was 15.

[Chelsea Handler]

Okay, so that's crazy. And how old were you when you left home?

[Scottie James]

I left home when I was sort of pursuit. When my parents decided. Well, and myself, it was, you know, all of us in my family collectively decided I wanted to pursue it professionally. I was 12. I was really young. So it was a massive commitment from my parents to have the trust in my coach at the time and his sister to look after me not only on the mountain, but off the mountain as well. And through that time, from 12, I was able to realize a professional career in the sport. And then by 14, I was offered the opportunity to go and represent Australia, which was a unique, special experience. And, you know, fortunately making it there. I was 15 at the time and taking full advantage of all the free McDonald's in Vancouver.

[Chelsea Handler]

That's nice that you get to eat McDonald's while you're a teenager growing up.

[Scottie James]

And that's not the case anymore.

[Chelsea Handler]

No, no, you can't. As soon as you're an adult, you have to stop that. But what was it like leaving your family at 12 years old? I mean, that must have been emotional. And for all of you guys, for your siblings, for your parents, for you.

[Scottie James]

Yeah, it was hugely emotional. And recently we just made a documentary, and for the first time in a long time, you know, it was kind of the first time that I'd really heard everyone else's experience about that. I mean, it's almost been 20 years since that moment when I left Melbourne and going away overseas on my own. I Remember being at the airport and it was just the floodgates were open. Everyone was very emotional, myself included. And all the way through the flight from Melbourne to Sydney, I was crying. And then all the way over to Europe and yeah, I think that my parents didn't even realize how emotional I was until we watched the film recently. And then I didn't realize how their side of the story until we watched it recently as well. And my mum said to me the other day, she's like, you know, if we had have known how upset you were, we never would have sent you. And I said to mom, I was like, yeah, but look what we've realized. Like as much as, as much as it was so hard in the moment and you know, I do think that all extraordinary things that you want to try and accomplish takes hardship and you know, that was mine. But I was, you know, able to travel with great people and I was in a, you know, in a good and safe environment. It was a challenging time, but it's nice to reflect on now.

[Chelsea Handler]

Yeah, I would imagine it just gives you so much, A, you, you grow up real quick. Right. And B, you just become really independent and self sufficient at a young age. Even if you do have people helping you.

[Scottie James]

Yeah, definitely. And I think, you know, even more so is, you know, the stigma with snowboarding. It's smoking, it's drinking, it's partying, it's, you know, it's, it's a wild scene still today. A little bit.

[Chelsea Handler]

All things I love, all things I love and support.

[Kathryn Law]

So you should start snowboarding, Chelsea.

[Scottie James]

Exactly.

[Chelsea Handler]

You can do that while you ski also, by the way, just FYI.

[Scottie James]

So my parents, even though naturally, I mean, now I'm a dad, I would be thinking about that. The environment and the world you go into, it's evolved a lot since then. But yeah, a lot of factors for them to think about, which I'm sure they lost sleep. Omar.

[Chelsea Handler]

Yeah, and also, I'm sure. And also it's such a. And then you're the baby on top of it. But it's also such a solitude, you know, it's like, I mean, I guess all these kind of mountain sports are very solitary unless you're doing, you know, like, you know, you're working together. But like, how does, how does that impact your relationship with other athletes and how does it impact your relationship with your coaches? Like you become, is it like, would you compare it to maybe like a tennis player or do you feel more like you're on more of a team?

[Scottie James]

Yeah, sure. So I Think the unique thing about snowboarding or our world, which is very cool, is everyone does have a good relationship. So you're up there at the top of the pipe, for example. You know, some might wish each other luck. Like, it's. It's a little bit more. Call it happy, go lucky in the sense of being a little bit less cutthroat. I'm probably more so on the other side where I'm up there. I have intention. I'm not necessarily focused on making friends in that exact moment. But, yeah, I would say that there is a sense of solitude that you have to be okay with being alone, be okay with being extremely selfish about what your endeavors are. You're not doing it for anyone. You have to be so, I guess, obsessed with the craft to want to do it for yourself. I've always found my team is more so, you know, my family, other people that have helped me in my journey. Like, that's the kind of weight that I ride with, is. I'm doing it because it wouldn't be satisfying enough for me if I was just up there with my own intent every week to just do it for myself. I think my team is. I want to do well for them. But, yeah, you're right. There is. It's a little bit more like a tennis player rather than, you know, a football team, for sure.

[Chelsea Handler]

Yeah. That's interesting. I mean, you get to travel all over to the world to train in different places.

[Scottie James]

What is.

[Chelsea Handler]

Is there anywhere you prefer never to go back to?

[Scottie James]

Oh, we did world championships in. In Georgia a couple of years ago.

[Chelsea Handler]

Georgia. The country.

[Kathryn Law]

The country.

[Scottie James]

Yeah, yeah, yeah, the country in Georgia. I forget the name of the mountain. We were very far from anywhere more. So it's actually. The country was cool, but this where we were, the weather conditions, it was out there, so probably there.

[Chelsea Handler]

I think Georgia is the country where I saw that video that went viral one year with, like, the gondola, where the gondola chairs were put on backwards, and then they started turning. They flipped it and reversed it. And then people were just flying off of the Godzilla because it was coming around like, 60 kilometers an hour.

[Scottie James]

It was, like flipping around, honestly. Sounds like. Sounds like something I would have seen when I was there, so it probably was.

[Kathryn Law]

Yeah.

[Chelsea Handler]

Tell us about your documentary. I want to hear about that.

[Scottie James]

Yeah, it was. It's been really fun. I mean, as the. We made the documentary called Pipe Dream and came out on Netflix on December 19, so it's still early days. It's had its premiere, which is. Yeah, it's been awesome. Awesome. And yeah, I think overall, it's obviously incredibly rewarding to have been able to go on such an amazing platform for myself, but also just for snowboarding is really exciting, just to get more people, hopefully more viewers and eyes and every. Everyone engaged in what we're doing up here in the mountains. And it was a pretty emotional process, getting it all together and. And obviously hearing from my family and other peers and hearing from other snowboarding competitors present in the past. And so it's quite cool to hear a lot of people's perspective, which I actually haven't heard before. So, yeah, it was a rewarding process. Long process, but really, really cool. And I've never told my story like that before, which was fun to do.

[Chelsea Handler]

Yeah, I can't wait to see it. That must be really interesting to see all these people talk about you. Because I think in life, you know, we talk about this a lot on this podcast. Like, you don't really have time necessarily to reflect on things. Like, especially when you're going like, you're an athlete, you're training all year long. Literally. What, you have, like, a month off a year or something? Is that right? A month off?

[Scottie James]

Yeah. Yeah. It's probably say, three months. Because you go Northern hemisphere season, which starts in October, goes through to April, first week of May, then you have June off, Then you, you know, then the Southern hemisphere winter starts. So you're kind of obviously always constantly chasing winter, so you get a few months off a year.

[Chelsea Handler]

Okay, so if you had to describe before we move on to the next part of that, I just want to. I want to know what you. When you are starting and you're competing and you're listening to music to get ready once it starts, what is in your head? If you fall behind by a fraction of a second or you don't hit the same, there's something that you want to hit. What do you say to yourself in that moment when something doesn't land like it's supposed to land? A hundred percent?

[Scottie James]

Honestly, I reflect on. In that exact moment, I just say, fuck it. Let's just go get it done. Because you can spend so much time thinking about, I should have done this better. Did I prepare well enough? What's he gonna do? You know, everyone's watching, everyone's expecting. It's like, that's what I do. I just say effort. And I think there's this really amazing piece in being able to say that confidently, because that's like, the best part about what I do is when you can drop in and just be so present in the moment with every trick and enjoying the environment. That's what I try and focus on. It'll be in the case. I'm sure it's similar for you if you're going out for a big gig or doing standup. It's like you, you've prepared so much, you have 10 more seconds. What else can you do other than just be like, like, let's just get after it and see how we go. And if things happen, it happens and you're going to learn from it. And that's what I, I do embrace that a lot. I think that, you know, you do spend a lot of time preparing and you can become way too meticulous and overthinking and over, over, over everything that you end up actually giving yourself. You have no satisfaction because you're like, well, what was all the work for if I can't just embrace the moment? So I do focus on that.

[Chelsea Handler]

Yeah. Yeah. And do you find that that's different now as you've gotten older, that you're more in the present moment than you were when you were competing as a younger person?

[Scottie James]

Definitely, 100%. I think naturally, you know, still young, but going through, you know, time when you're younger, you do spend and waste so much time thinking about things that just do not matter at all, whether that's on the mountain or off the mountain. You know, I did that, went through that. Whereas now I'm very much. Yeah, very present. You know, I know what I want to accomplish. I know who I am as a person. My two feet are on the ground and I do lean into that.

[Chelsea Handler]

Like, if you had one weakness that you would, that you would like to work on or that you're working on, what would that be?

[Scottie James]

It's a good question. I. My weakness would probably be besides being a snowboarder. Besides being a snowboarder. It would be. To be honest, it's still, it's funny, like, even after having found such a groove in, you know, maybe whatever you define success as in my case, you know, being able to compete really well and do well in advance is still belief. Like, you still have moments where, you know, you, you prepare so well and you're like, all I have to do is show up and put my best foot forward and land a really amazing run and it'll, you know, it'll go my way. We're well enough and in tune enough that we know when we have the tools to win. If you don't, you know, where you're kind of at. And I still sometimes, yeah, I battle with that belief of can I actually realize now what I'm trying to accomplish and have I taken the right steps to get there? So I would say that that's something that I continue to work on. But because as much as I feel I am working on it, I also think it's kind of my blessing because then I don't take advantage of any day. Every opportunity is an opportunity. I try and squeeze every opportunity that I can. Training. And maybe that's that lack of belief that it makes me go overboard in term with my preparation, my training. So I don't know, it's probably whether it's a weakness or maybe it could. Might not be, but that would be.

[Chelsea Handler]

One that I feel. I mean, circling back to the subject or the topic of reflection, I always think if there's something big, high stakes in my life, which is obviously very different than yours, but I always think, okay, think about all the things that led to you being here. Think about all of where you came from. So when I talk about reflection, I know as an athlete, you're moving so fast, you're training so much, you have limited time off or limited off season. And it's like you really have to take note of where you began and where you've come, how far you've come. You know, as a reminder for anyone really, in any situation, it's like, oh, I'm the one who got myself all the way here, obviously with help of coaches and support from your family, et cetera, and your wife. But also to really remember, like, how, you know, how far you've come.

[Scottie James]

Yeah, definitely. And I think the, the one I always sit on a lot is the courage. I think everyone, we all have passions, we all have something that we want to realize in our lives. And I feel very fortunate that I'm one of the ones that was. Had the courage to actually continue and go for it, particularly with, you know, the setbacks that you have when you're young. And I think that's across. A lot of people always ask me, like, oh, who do you look up to? Who do you admire in your life? And to be honest, I don't have one person. It's always people that I look at and I hear their story and I hear about their adversity and their courage to actually pursue what they want to do in their life. And that's hard. So I do focus on that too, is the courage. Takes a lot of courage to actually commit to your passion in life and I've done that. Which has been rewarding and fortunately worked out.

[Chelsea Handler]

But, yeah, yeah, people always say that to me. Who do you look up to? Like, who is your favorite? And I was like, well, Bill Cosby. But that didn't really work out for me, so I have to stop mentioning it. That's not a hero anymore. Anyway, we're gonna take a break, and we're gonna be right back with Scottie James. Okay. This episode is sponsored by BetterHelp. Sometimes it can feel like everyone else has it all together in their love lives. Whether married, dating or single, the truth is, most of us are still figuring it out and finding our way. And no matter where you are in your romantic journey, therapy can help you find your way. Help you determine what you want, what feels heavy, and how you could take some pressure off yourself. I get it. February is full of flowers, candy, stuffed animals, Valentine's Day, and of course, lots of talk about relationships and dating. And no matter where you are, whether you're married or dating or single or just focusing on you, you're right on time. Therapy can help you find your way and see more clearly where you wanna be. And that's why there's BetterHelp. BetterHelp therapists work according to a strict code of conduct and are fully licensed in the US they do the initial matching work for you so you can focus on your therapy goals. A short questionnaire helps identify your needs and preferences. And their years of experience mean they typically get it right the first time. If you aren't happy with your match, switch to a different therapist at any time from their tailored recommendations. Sign up and get 10% [e-mail] dearchelsea that's betterh e lp.com dearchelsea let's be real. We all want to look a little younger without a visit to a surgeon, lying about our age, or pretending we suddenly drink more water. That's why Plexaderm is taking the beauty world by storm. Millions have tried it, and not to mention it has a 4.0 review on Amazon. Why? It's because it works. So say goodbye to dreaded, puffy under eye bags, wrinkles and crow's feet. With Plexaderm, your skin can look years younger in minutes and it lasts up to 10 hours. 10 hours? Seriously? Influencers rave about it, fans can't get enough, and we are just obsessed. Elle magazine even gave it their Editor's Choice Award for Best Instant Wrinkle Filler 2025. Basically an official stamp of approval from the pros. The Best part, the appearance of fine lines, wrinkles under eye bags dramatically reduced in 10 minutes or less. No surgery, no gimmicks, just results that last. So join the millions of users and try it now for only $14.95 with free shipping. Visiting plexaderm.com Chelsea that's plexaderm.com Chelsea if you're looking for a wine that's not just delicious, but also a total crowd pleaser, let me introduce you to Josh Sellars. This California wine brand has over a dozen award winning wines. From crisp Sauvignon Blancs to velvety Merlots. Josh Sellars has the perfect wine for every occasion. Serving up a juicy steak at your next barbecue. Josh Sellers Cabernet Sauvignon is the perfect pairing. Unwinding with friends after a long week, you can't go wrong with their Pinot Grigio. With so many delicious wines to choose from, Josh Cellars has something for everyone. Josh Cellars wines are made for sharing with those who matter most to you. And each wine is made to exacting standards. So no matter which varietal you choose, you can be confident it will be well balanced and delicious. Josh Cellars is a proud sponsor of Dear Chelsea. Visit www.joshcellars.com Chelsea and join the Wine Club to get 20% off. Please drink responsibly. It's the new year, which means everyone's talking about doing better, eating better, feeling better, taking care of themselves. And if you're thinking that way about your own health, your dog probably deserves that same energy. Doug eats just fresh from Just Food for Dog dogs. It's real human grade food, not processed junk. And it's the number one vet recommended fresh dog food. And yes, I've seen the difference. More energy, shinier coat, and a dog who suddenly cares very deeply about dinner. Because let's be honest, you wouldn't eat the same processed thing every day. So why are we feeding that to our dogs? No judgment, just logic. What makes this work is that it's shelf stable. I don't need freezer space, I don't need to plan ahead, and I definitely don't need a lifestyle overhaul. If you're starting the year trying to do better, start with your dog. Go to justfoodfordogs.com and get 50% off your first order. No code needed. Just a smarter way to start the year.

[Scottie James]

Right.

[Chelsea Handler]

And we're back with Scotty James. Okay, Scotty James is on his way to the Olympics, so. And this is not his first time at the Olympics. This is your fifth time at the Olympics.

[Scottie James]

Fifth. Yes, vintage.

[Chelsea Handler]

Yeah, vintage. Fifth time. My gosh. Okay, so we now we take questions from callers. Scottie, are you ready?

[Scottie James]

I'm ready.

[Chelsea Handler]

You seem ready. You seem ready. Yes, Katherine, what do we got?

[Kathryn Law]

All right, well, we're gonna start with a couple skiing snowboarding questions, but then move on to some interpersonal, juicy stuff.

[Chelsea Handler]

So then we're gonna move on to some gynecology questions just to keep you comfortable. Exactly.

[Kathryn Law]

Right in your wheelhouse. So we're gonna start with a brand new segment, which is our one drink question. And this is just a little quickie. So our listener says, Dear Chelsea, this is not an incredibly deep question. It is about skiing. I grew up snowboarding and decided I wanted to switch to skiing after college for longevity purposes. I visualize a 50 year old version of myself who's a badass skier and spends a third of my year in Telluride. Here are my questions. One, what age did you start spending serious time skiing? Do you think 31 is too late?

[Chelsea Handler]

No.

[Kathryn Law]

2, how long did it take you to feel confident on Blacks? With age, my fearlessness has faded, and I'm frustrated with how much hesitation I have going down the mountain. How many lessons did you have before you felt really capable and confident to handle all terrain?

[Chelsea Handler]

Great questions. I love it. First of all, I didn't start getting into skiing like, seriously seriously until I was like 39. I mean, I skied in my 30s, but I didn't start, like, taking, like, actual private instruction, which are pretty expensive. So if you can afford that, great. But if not, your fearlessness gets replaced by competency. I would say, you know, what you lose in fearlessness, you gain in competency and capability. So the more time you spend on the mountain and the more runs you do in bad conditions, in good conditions, in powder and groomers, all of it, you become a better skier. And I, like, I'm a really good skier now. I could ski down pretty much anything. My friends took me down something like two days ago that I was like, if I had done that 10 years ago, I would never have taken. I would never have made it. Right? I would have been like, no way. So that felt really good. But, you know, 31, yeah, you're down. You could do whatever it takes. Like, I think it takes a good hundred days on a mount, but you want to get instruction from someone who knows what they're doing so you don't create really bad habits and then beat up your body. Right, Scotty?

[Scottie James]

Whoever asked the question lost Me, it. I transferred to skiing. So no comment.

[Chelsea Handler]

First of all, and also to our writer in you doing the right thing by leaving snowboarding and transferring to skiing. Scottie and I are from two different schools of thought, obviously, and I support you 100%. And that's it. Problem solved.

[Scottie James]

Okay.

[Kathryn Law]

All right.

[Scottie James]

Okay.

[Chelsea Handler]

Cheers. Is that our one drink? Yes.

[Scottie James]

Scotty and I can confirm Chelsea's actually looking at potentially, you told me earlier you're looking at doing some instructing at a local resort, so maybe you could take that on.

[Chelsea Handler]

I gotta get my level ones first. I gotta get my level ones, two, three, and four. Yeah. Double blacks. Yeah. It takes a while to get down, but by the way, once you get good at skiing, at double black, you don't even look at whether it's black or blue or. It doesn't matter.

[Scottie James]

You're.

[Chelsea Handler]

You're fine.

[Scottie James]

It's true. No, but to. To second you. You're right. I think the more consistency you have and the more often you do it and the. And your curiosity is where you'll win. So go for it. But you should stay on the board. Yeah.

[Rebecca]

All right.

[Kathryn Law]

Well, our first caller today is Jess, and she is calling in from Vancouver. So she says, dear Chelsea, I've fallen up. This is another skiing question, but it will make sense to you, Scotty. So I've fallen out of love with skiing. Growing up, some of my best memories were spent on the slopes, and I chose a grad school partly based on proximity to a hill. Post Covid, I took a break from my studies and moved to Queenstown, New Zealand to work on the ski field. I got paid to ski every day and loved it. Wanting to improve, I signed up for a ski instructor exam. I really enjoy developing my technique. And Chelsea? I too ended up sleeping with my ski instructor. We're now married. My husband is a highly skilled snow sports professional, and skiing is central to his world. But within that world, I often don't feel welcome. When we're with his friends, conversation revolves almost exclusively around ski technique and criticism of the industry, and I largely feel excluded. Being surrounded by constant evaluation has made me wonder what he thinks about my skiing, what his peers think too. It's such a visible sport, and I've seen the ego driven underside of it. Over time, I've come to associate skiing with feeling inferior. When my husband and I do ski together, the days have slowly morphed into being about filming him for YouTube and marketing his business. I've become the cliche. I've become the cliche Instagram girlfriend we moved to B.C. a couple years ago and have incredible skiing available to us. We've had conversations about this, but I find myself sabotaging ski days by offering just to film without being asked just to avoid skiing myself. Honestly, I'd rather be in the lodge with a margarita. Chelsea, how can I build my ski self esteem and fall back in love with the mountains again? Thanks so much, Jess.

[Chelsea Handler]

Well, Jess, it feels like you gotta find a group of, like, women to ski with so that you don't feel like that you got a new. I mean, it doesn't even have to be women. It just has to be people that aren't that judgy or so psychotically talking about skiing all the time. That's not fun either. Nobody wants to talk about technique all the time. Unless you're Scotty and you're on your way to do the Olympics and that's all you have to talk about.

[Scottie James]

About even. I don't do that. I promise.

[Chelsea Handler]

Yeah, actually go back and tell them, Scotty. James doesn't even talk about it as much as you guys do, and he's competing in the Olympics.

[Rebecca]

Yeah, I. When I was in New Zealand, we had. I worked in the industry a little bit and I found some group of women that were a little bit less intense about it. So it was really fun. But I. I haven't quite found that here in B.C. and Canada. But, yeah, I think that's a great idea.

[Chelsea Handler]

But you know what? You could find ski groups online. You know, there's like. I'm in a ski group on Saturdays, like, Club Link at Whistler, Blackcomb, where I ski. You know, we have a guy that just cuts the lines for us. You know, when it's busy and, like, takes us, it's fun. You can do that. You can join. And then Cypress and Grouse are in Vancouver. I mean, that's so much fun. Night skiing, I love that. But yeah, I would just change the channel. Like, first of all, stop going and recording your boyfriend, husband, whatever he is. Like, what are you, his assistant? I mean, have him go. That's not fun for anyone. I mean, do you have children? No, not yet. Exactly. That's why you shouldn't be filming anybody because he's an adult man. I mean, you know. Scotty, what do you have to say to this? Anything?

[Scottie James]

I would say, firstly, you're welcome over to our side any day of the week.

[Kathryn Law]

The snowboarding side.

[Scottie James]

Get you some snowboarding. Yeah, we can. We can bring you in. It'll be a warm welcome. Secondly, it's actually really interesting. My ears pricked up when you said that you sometimes don't feel like you fit in into conversations. It doesn't matter your level. I have that same feeling in my world sometimes there's maybe a certain type of person or a certain type of, you know, way that people perceive snowboarders or skiers in this case to be. And if you don't fit that mold, you don't really feel like you're a part of what they're doing. And at the, you know, even for me, I always got a bit insecure about that. But I think that the second that you realize, I guess, who you are and what you're doing and why you're actually even out there, like firstly, just wanting to have fun. And that's what anyone should be up there doing. If you're not pursuing it professionally, I think just find a bit of sanity in that you actually enjoy it. And if people start to have a go at you about not being on their level of knowledge, like, who gives a shit? It doesn't matter at all.

[Rebecca]

It is quite a made up sport, I suppose too, you know, unless you're in a gate and you're trying to get from A to B really quickly or you're being judged on specific criteria, it is made up. So I do try to tell myself that, like, it doesn't really matter what I look like, I'm still having fun and that's the point.

[Scottie James]

But.

[Rebecca]

But yeah, there's definitely a little bit of ego and I think that comparison that.

[Chelsea Handler]

Yeah, but that's men. I mean, that's why, like, don't ski with a group of men. Like, that's just not fun, you know, I think that's your solution.

[Scottie James]

Yeah, it's like you have to be one exceptions.

[Chelsea Handler]

Yeah, there are. Scottie, you seem like a really nice guy, but again, you know, still a snowboarder, a world champion, but a snowboarder nonetheless. So you just gotta get, you gotta change the channel and decide who you're skiing with and just be honest with your partner and be like, listen, it's not fun. I don't feel like I wanna have fun on skis. I'm like losing my love. Have you expressed that to him, by the way?

[Rebecca]

Yeah, we've, we've talked about it a bit. I think the worst season was last season. Just I didn't actually get a single day to ski to myself. But yeah, knows how I feel. The issue is, is that he's trying to make YouTube his business and I'm kind of tied into that as well.

[Scottie James]

Right.

[Rebecca]

Like, he doesn't really have anyone else to go out with him. So sometimes. Sometimes I kind of get pulled into that. But I guess trying to make that boundary or draw that line.

[Kathryn Law]

A college student. Find a college student to do that.

[Scottie James]

Yeah.

[Rebecca]

Okay. That's a good idea.

[Chelsea Handler]

Great idea. I wasn't gonna say that, but I was gonna say you can also, you know, you do something for him and then he. And then. Okay. In exchange for that, you get to go skiing alone or you go skiing with a group of people or you go skiing and he's not allowed to talk about skiing for the entire day. You know, like, figure out what the compromise is while you're skiing. You're not allowed to talk about skiing while we're skiing.

[Scottie James]

For every photo or video, it's one margarita. I mean, come on.

[Chelsea Handler]

Yeah, perfect.

[Scottie James]

Let's go. Good negotiation.

[Chelsea Handler]

What is your drink of choice on the mountains, Scotty? When you can have a drink, when you are celebrating, what is it?

[Scottie James]

Good question. After. After, like, an event. Probably champagne, actually.

[Chelsea Handler]

Yeah. I mean, that's because they're spraying it all over you. So readily available.

[Scottie James]

Cliche. True. Yeah.

[Chelsea Handler]

I like a Moscow mule on the mountain. Or I like a stiff margarita. Because I like to have a margarita juice boost at around 11. If I go out around nine, I like to stop, have a little margarita at 11th and then go back out and have a little more bravery.

[Scottie James]

This is. This is the Olympics of skiing drinking knowledge. Watch house.

[Kathryn Law]

Yeah.

[Chelsea Handler]

Yeah. So there you go, Jess. And hopefully I'll run into you at one of these mountains.

[Rebecca]

Yeah.

[Kathryn Law]

Yeah.

[Rebecca]

We're gonna go into the interior in a few weeks in February. So. But. Yeah. Yeah.

[Chelsea Handler]

Oh, good.

[Scottie James]

Okay.

[Chelsea Handler]

Well, yeah, but don't lose your love. You know, if you love skiing, like, make sure you, like. You've gotta, like, guard in your passions. You know what I mean? Just, like, you have to, like, guard in your relationship. You have to, like, make sure you do what you want to do and enjoy something that you love that you, like, kind of got ruined by somebody else. Like, don't let that. Don't let them take that away, you know? Go and be, like, true to yourself and get back out there.

[Rebecca]

Yeah. I think the idea of finding women to ski with is a good one.

[Scottie James]

Yeah. Always.

[Chelsea Handler]

Always. If you're a woman. I like, you know, skiing with women. I like women guides. Every. I'm like, if she can move her body like that, then I can move my body like that. You know, it's easier sometimes with a woman when you are A woman.

[Rebecca]

Yeah, that's a good point. Okay. Things to think about. Thank you, guys.

[Chelsea Handler]

Okay, great. Thanks for calling in. Take care.

[Scottie James]

Thanks.

[Kathryn Law]

Thanks, Jess.

[Chelsea Handler]

I would love to do like a thing where they had to. It was spectators had to compete drinking while at the Olympics and then interviewing the athletes after. Who could do that? The best. And that would be me. I would now lose my shit. The more alcohol in my system, the more clarity I get.

[Scottie James]

I mean, I think that's a fair pitch. I do too, actually.

[Chelsea Handler]

I don't know why I'm not doing that. I don't know. They must have hired somebody else. Somebody more reliable. Okay, Katherine, what else? What else do we got?

[Kathryn Law]

Well, our next caller is Rebecca. She says, dear Chelsea, I am a 42 year old who moved to a Greek island on my own just over a year ago. After nannying and waiting tables my whole life, I decided it was time to live my dream and stop waiting for my person, for my life to begin. So I used my savings to do the Golden Visa and buy property in Greece while giving myself a few years to really give my all to my business and gain clients. Clients. I know it will take some time to support this life financially. With a savvy budget, I can support myself with savings for another year until my business picks up or I have to go back to the US and find another nanny job. Recently, I got on a dating app and found a really great guy who's also an expat. Our relationship is quite new, but we're very compatible and we're. We're falling fast for each other. He's in a very different financial situation. He recently retired. He's in his 50s with plenty of money and is constantly taking lavish vacations all over the world. At first it sounds amazing, right? But when I really think about it, I'm not in a position to actually join him on these vacations. Even though I can work from anywhere, just paying for one splurgy meal on a trip would cost the same as my budget for two weeks here. So my question is, how and when do I approach this money conversation? Do I just turn down trips with him? He's currently angling for a getaway to the Maldives. We're only six weeks in, so is it too soon to talk finances? Rebecca.

[Chelsea Handler]

Well, I mean. Hi, Rebecca. How are you?

[Rebecca]

Hi.

[Scottie James]

Hi.

[Chelsea Handler]

This is our special guest, Scotty James. He's heading to the Olympics. He's the best snowboarder of all time. So you came to the right place because he's got lots of answers for you.

[Rebecca]

Perfect.

[Chelsea Handler]

Has it come up yet? Have you guys been on a vacation? I mean, usually the person that wants to go on the vacation that badly is happy to pay for it, but have you guys been on a vacation like that together, like, a nice vacation yet?

[Scottie James]

Yet?

[Rebecca]

Yeah, we went to Vienna for New Year's. He paid for most of it, but I had to pay for my plane ticket, which wasn't that much, but it's still significant for me. So I just kind of have to measure, like, how many times can I do that? We're going to Santorini in a couple weeks. And again, he's paying for the trip, but I'm paying for my plane ticket. And so, yeah, it's. It's. You know, I'm not really sure how to. I'm not great at talking about it yet, and I'm not sure, because it's so new, what the best way to do it is.

[Chelsea Handler]

Yeah, well, I don't think for. Yeah, I know it's not a sexy conversation to talk about finances, especially when they're like, you're strapped for them, but I think you should just have a very honest conversation and just let him know, like, what your situation is. Go be like, I'm sorry I'm not as established, like, these vacations really, like, even the plane ticket is a lot for me. That's, like, my budget for. However, I mean, plane tickets are fairly. If you're in Greece and you're going to Santorini, obviously that's a little bit more affordable.

[Rebecca]

Yeah, yeah, that's true. That's true. It's more that they add up. And also just things like this summer, I don't like to be here for August because it's too hot and too crowded. So if I were single, I would be looking for a house swap or looking to house sit, like, something free that I could do. He keeps talking about going to the Maldives, and he keeps hinting, do you want to come or not? He hasn't actually directly said that, but he said, do you like the Maldives? Do you think you'd ever want to come? So it's like we're not quite there yet to, like, plan that. But then I need to also be planning my life just in case we don't go.

[Chelsea Handler]

But I think you should enter this. Listen, Scotty's married to an heiress, so he's in the same boat, basically as you are.

[Rebecca]

Okay.

[Chelsea Handler]

But I think you should just bring a lightness to this conversation and be like, listen, I am excited about all of this potential, and I know we're very new. But I just really want to be transparent. This should be like an in person conversation about where you are financially, what your plan is. Like, everything you just mentioned in your letter is worthwhile knowledge. Like, you moved to Greece. You have a year to set up your business, you know, or before you have to go back to the States, which you definitely don't want to do right now. So you, like, you know, just be very transparent without asking or expecting. You know what I mean? Just saying, like, I want to figure this out together, and I don't expect you to pay for everything. I want to contribute, so what's the best way I can do that? Maybe there's a different way that you can contribute that isn't fiduciary. You know, like, maybe you can, you know, maybe you can be involved in the planning more or you could pick up the restaurants or do some more of the legwork. You know, figure out a way to contribute if he's cool with it. But I think you should just, you know, don't make it dire. Just say, hey, I want to just start talking about this. I know it's not a sexy conversation, but I want to be transparent and I don't want to, like, take advantage of the situation. You know what I mean? Just be very honest. I think that gets the ball rolling in the right kind of candor and transparency, especially at the beginning of a relationship, it's important to say those things.

[Rebecca]

Yeah, okay. Yeah, that's really helpful.

[Kathryn Law]

Yeah. And then also giving him the option of, like, if it doesn't work for, you know, you just bring for the vacation, like, I'm totally cool to do a house swap and, like, I'll see you in a month when you get back from the Maldives.

[Chelsea Handler]

Yeah, yeah, Threaten him. Who knows who I might meet in that time? Yeah, who knows who I'll meet him to meet while you go to the Maldives. That always works.

[Scottie James]

And congrats on having the courage to move, Try something different. I think that takes a lot of courage, so respect for doing that.

[Rebecca]

Oh, thank you.

[Chelsea Handler]

Yeah, it does. It does. To get up and move to someplace where you don't know anyone and so far away. Like, I love that move. And I think you'll know you'll get rewarded. I mean, there's. Greece is always, always a good place to be.

[Rebecca]

Yeah. Yeah. I love it here so far.

[Chelsea Handler]

Okay, well, good. Good luck. And yeah, let us know how that conversation goes. We, like, follow up calls.

[Rebecca]

Okay, awesome. Yeah, thank you so much.

[Kathryn Law]

Thanks, Rebecca.

[Rebecca]

Okay, bye.

[Chelsea Handler]

Bye. Bye. We're gonna take a quick break and we're gonna be right back to wrap up with Scotty James. Let's be real. We all wanna look a little younger without a visit to a surgeon, lying about our age or pretending we sudden water. That's why Plexaderm is taking the beauty world by storm. Millions have tried it and not to mention it has a 4.0 review on Amazon. Why? It's because it works. So say goodbye to dreaded puffy under eye bags, wrinkles and crow's feet. With Plexaderm, your skin can look years younger in minutes and it lasts up to 10 hours. 10 hours? Seriously? Influencers rave about it, fans can't get enough and we are just obsessed. Elle magazine even gave it their Editor's Choice Award for Best Instant Wrinkle Filler 2025. Basically an official stamp of approval from the pros. The best part? The appearance of fine lines, wrinkles under eye bags dramatically reduced in 10 minutes or less. No surgery, no gimmicks, just results that last. So join the millions of users and try it now for only $14.95 with free shipping. Visiting plexaderm.com Chelsea that's plexaderm.com Chelsea if you're looking for a wine that's not just delicious but also a total crowd pleaser, let me introduce you to Josh Sellars. This California wine brand has over a dozen award winning wines. From crisp Sauvignon Blancs to velvety Merlots. Josh Sellers has the perfect wine for every occasion. Serving up a juicy steak at your next barbecue. Josh Sellers Cabernet Sauvignon is the perfect pairing. Unwinding with friends after a long week, you can't go wrong with their Pinot Grigio. With so many delicious wines to choose from, Josh Sellers has something for everyone. Josh Cellars wines are made for sharing with those who matter most to you. And each wine is made to exacting standards. So no matter which varietal you choose, you can be confident it will be well balanced and delicious. Josh Sellers is a proud sponsor of Dear Chelsea. Visit www.joshcellars.com Chelsea and join the Wine Club to get 20% off. Please drink responsibly. It's the new year, which means everyone's talking about doing better, eating better, feeling better, taking care of themselves. And if you're thinking that way about your own health, your dog probably deserves that same energy. Doug eats just fresh from just food for dogs. It's real human grade food, not processed junk. And it's the Number one vet recommended fresh dog food. And yes, I've seen the difference. More energy, shinier coat, and a dog who suddenly cares very deeply about dinner. Because, let's be honest, you wouldn't eat the same processed thing every day. So why are we feeding that to our dogs? No judgment, just logic. What makes this work is that it's shelf stable. I don't need freezer space, I don't need to plan ahead, and I definitely don't need a lifestyle overhaul. If you're starting the year trying to do better, start with your dog, go to justfoodfordogs.com and get 50% off your first order. No code needed. Just a smarter way to start the year right. Dumb skincare companies that make billions by making us feel like getting older is a bad thing. It isn't. I'm 50 years old and guess what? I love it. I have earned this face. That's why I wanted to talk to you guys about Froia Organics, a company that actually gets it. They know they're not going to magically make you look like you're 20 again. And honestly, you need acid washed jeans and crimped hair to do that anyway. And I'm not looking to look like I'm 20 again. What they will do is work with your skin to make it look and feel the healthiest for your age. They do this by using wild arctic plants that survive in some of the harshest environments on the planet. Plants like arnica and sea buckthorn are packed with antioxidants and omegas that increase collagen production while repairing the skin's natural barrier. It's like the equivalent of going vegan for your face, minus the pretension and hemp braces. No fillers, no bullshit, just natural ingredients that your face will love. Go and check out froyaorganics.com now and get 40% off. And we're back with Scotty James. Scotty, do you spend a lot of time on the mountain when you're not like, do you spend any time on the mountain when you're not training?

[Scottie James]

Yeah, I would say when my family's around, yes. Like, my dad loves snowboarding, so he's always keen to be on the hill. He's the guy that's up at the lift line first and waiting for the chairlift to open. So I definitely, when he's around, I'm up there just for fun and to go cruise around. But to be honest, during a competition week, I'm not on the hill too much. Other than competing in training, what is.

[Chelsea Handler]

Your meal right before you compete?

[Scottie James]

I love spaghetti bolognese. Yeah, I just. I mean, probably a night before. Cause if I had it right before I compete, might be a little on the heavy side. And I'm already heavy, as I explained earlier, so throwing around spaghetti bolognese in my stomach, doing flips is not a great outcome. But, yeah, probably that.

[Chelsea Handler]

I would say, yeah, it's nice to have to eat spaghetti bolognese for your profession since you need to carb load and you need to get your body stored up. It's nice to have that kind of responsibility.

[Scottie James]

Sure. Yeah. This is. Sure.

[Chelsea Handler]

And will your family. Your family's going to be at the Olympics? Yeah, yeah.

[Scottie James]

So the fam will be there, which will be really nice. They obviously with. Last Olympics was in China. The country was still closed, so it was pretty interesting experience. It was like just us and robots. Didn't really feel like an Olympics and robots and it was. Yeah. Strange. So it wasn't like. Didn't really feel the. The energy last time. So it'll be nice to have, you know, Italy will be great.

[Chelsea Handler]

I love it.

[Scottie James]

Italy as a country. Spaghetti bolognese on hand, obviously, whenever. But no, it'll be master of the family. That'll be good.

[Chelsea Handler]

Okay. Well, I cannot wait to see you win a gold medal. So we will be watching. It was delightful speaking with you. I hope I get to meet you someday in person. Maybe I'll pop by the Olympics this year. Who knows? Anything's possible.

[Scottie James]

If I get the job done. We'll promise you one thing. We're going snowboarding together. You shake on it?

[Chelsea Handler]

Well, okay. Yeah.

[Scottie James]

And then I'm gonna take a photo of it and be like, she's transitioned.

[Chelsea Handler]

Yes. Transition in more ways than one. Thank you, Scottie. Thanks for being here.

[Scottie James]

Thank you guys so much for having me. I appreciate it.

[Chelsea Handler]

Okay, take care. Okay, guys, the High and Mighty tour is about to begin. I'm in D.C. february 13th, February 14th, Atlantic City, which I just added. 15th is Norfolk, Virginia. February 19th, Madison, Wisconsin. February 20th is Milwaukee, Wisconsin. February 21st, Detroit, Michigan. February 22nd, Rama, Ontario. That's Canada for those of you who don't speak Canadian. March 13, Cleveland, Ohio. March 14, Columbus, Ohio. March 15, Cincinnati, Ohio. And then March 20 is Denver, Colorado. March 27, Portland, Maine. March 28, Providence, Rhode Island. March 29, Springfield, Massachusetts. April 10 is Chicago. I'll be at the Chicago Theater. April 11, Indianapolis, Indiana. April 12, Louisville, Kentucky. April 16 is Albuquerque, New Mexico. April 17 is Mesa, Arizona. April 23 is Kansas, City, Missouri. April 24 is St. Louis, Missouri. April 25 is Minneapolis, Minnesota. April 30, Nashville, Tennessee. May 1 is Charlotte, North Carolina. May 2 is Durham, North Carolina. May 6, I'm doing Netflix is a joke festival. I will be in Los Angeles. That is a new announcement. And May 15, Saratoga, California May 16, Monterey, California May 17, Modesto, California and then June 4, Portchester, New York. June 5 is Boston, Mass. And June 12 is Portland, Oregon. And then Seattle is June 13. So suck on that, everybody. Go to chelseahandler.com for tickets.

[Kathryn Law]

Do you want advice from Chelsea? Write in to dearchelseapodcastmail.com Find full video episodes of Dear Chelsea on YouTube by searching earchelseapod. Dear Chelsea is edited and engineered by Brad Dickens Executive Producer Kathryn Law. And be sure to check out our merch@chelsea handler.com.

[Chelsea Handler]

It's time to dump skincare companies that make us feel bad about getting older. I'm 50 years old and guess what? I'm loving life. Froia Organics is completely different. They know they're not going to magically make you look 20 again, and honestly, who wants that anyway? But they do use arctic plants like arnica and sea buckthorn that hydrate, repair and protect your skin's natural barrier, giving you healthy, radiant skin at any age. No fillers, no bullshit, just natural ingredients that actually work. Visit FreyaOrganics.com now to get 40% off if you're looking for a wine that's not just delicious but also a total crowd pleaser, let me introduce you to Josh Sellars. This California wine brand has over a dozen award winning wines, from crisp Sauvignon Blancs to velvety Merlots. Josh Sellars has the perfect wine for every occasion. Serving up a juicy steak at your next barbecue. Their Cabernet Sauvignon is the perfect pairing. Unwinding with friends after a long week, you can't go wrong with their Pinot Grigio. With so many delicious wines to choose from, Josh Cellars has something for everyone. Josh Cellars is a proud sponsor of Dear Chelsea. Visit www.joshcellars.com Chelsea and join the Wine Club to get 20% off. Please drink responsible.

[Kathryn Law]

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[Chelsea Handler]

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[Kathryn Law]

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[Chelsea Handler]

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[Scottie James]

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[Chelsea Handler]

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[Chelsea Handler]

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[Rebecca]

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[Chelsea Handler]

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