The "Strava Outlaws" Set a New Skiing Speed Record on The Middle Teton's Ellingwood Couloir

To watch Jim Ryan and Madison Rose Ostergren ski is a thing of beauty.

They were the immediate favorites to win POWDER’s inaugural Sun Valley Stampede back in the spring of ’26, and while neither left with the top prize, the general consensus amongst the crowd was: “Holy sh*t. Those two can ski.”

In the self-titled Jim & Mads Show on YouTube, the pair document their intense, borderline unhinged skiing endeavors for the world to see. The episodes follow a familiar format that typically includes lots of laughter, at least one moment when Mads questions what Jim has gotten her into, and some of the best skiing humans are capable of.

The first episode of the new season dropped today, October 5, 2026, and is titled, “watch this before we get in trouble… again (Chasing Strava Records in Jackson Hole).” The title references a video from last season that has since been deleted, in which Jim & Mads chase Strava speed-skiing records around Jackson Hole Mountain Resort (more on that later).

The new episode, while not filmed at an active ski resort, is arguably more impressive.

Tap or click below to watch as Jim & Mads attempt to descend the Ellingwood Couloir on The Middle Teton, in the middle of July, as quickly as possible. Keep reading for a quick Q&A with the duo about the episode and plans for more Jim & Mads content.

Jim Ryan and Madison Rose Ostergren Q&A

Why was the Strava Outlaws episode from JHMR deleted?

Jim: “Let’s just say the OG episode was a little ahead of its time.”

When was the new Strava Outlaws episode recorded?

Mads: “We filmed it in July!”

Jim: “I think Grand Teton National Park is arguably just as fun in July as it is in December. No avalanches, more sunshine.”

What kind of prep goes into skiing a line like Ellingwood Couloir as fast as possible?

Mads: “A lot of preparation goes into skiing a line like the Ellingwood. It’s a very steep, technical couloir in Grand Teton National Park, with sustained skiing over 50 degrees. When you watch the video, it is obvious that Jim is skiing with an insane amount of skill… but it has less to do with the line and more to do with a lifetime of skiing fast in variable conditions. He has just spent so much time in steep terrain… and he’s a little crazy.”

Jim: “I had skied the line before, but Mads hadn’t, so she was essentially skiing it on-sight. That’s wild to conceptualize when you watch her drop in. That line is so consequential, and she ripped it.”

What gear were you using for this episode?

Mads: “A lot of the time in the backcountry, we use our lightweight ski-mountaineering kits, but for this episode, we actually went with our resort setups.”

Jim: “Yeah, I convinced Mads to carry the heavy set up. I knew the speed we would have to carry to get the Strava crown, and I legitimately thought light setups could result in disaster. That’s why we work out, right? So we can carry plug boots into the high alpine?”

Mads: “We were both skiing in Dalbello DRS race boots and the Völkl Mantra skis, along with lightweight Helly Hansen shells and base layers.”

What can we expect for the rest of this season of the Jim & Mads Show?

Mads: “Our next episode is about Ridgway, aka the Superbowl of Skijoring. That episode is amazing. The production level goes crazy.”

Jim: “Mads and I also broke off this year and made an episode each on our own. Mads made this unreal short film, “Not a Chick Flick,” with Veronica Paulsen and the next generation of freeride women. It’s so good.”

Mads: “Jim paired up with Sam Hennessey, one of the most badass ski alpinists in the US, to climb and ski a new variation on the Grand Teton… I’m not sure if what they did has ever been done before, but I doubt it.”

Jim: “We also have a gear test, Mads went to Nor-Am Ski Cross Finals, and we wrap up the season with The Killington Superstar Showdown, the episode documenting the first-ever Jim and Mads event. It’s so fun. People skied out of their minds. I’m really proud of how that event and episode turned out.”

Do you have other Strava Outlaw episodes planned? If so, where were they filmed?

Jim: “We have plans to film more Strava Outlaw episodes this upcoming season, but this is the only one we’re releasing this fall.”

Mads: “If you like the vibe, stay tuned. Maybe we’ll be traveling to a mountain near you…”

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