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Come Fan with UsFriday, June 19, 2026

Chris Cole’s famous Wallenberg video is a lesson in persistence

When I need to feel inspired, I watch this skateboarding video.

Chris Cole grinding on his skateboard during competition, with red and white graphic art surrounding him.
Chris Cole grinding on his skateboard during competition, with red and white graphic art surrounding him.

I love skateboarding because its stars are more admired for trying difficult things and failing than they are for having a high success rate.

Despite what the X Games and skate videos might have led you to believe, skating is primarily about repeatedly eating shit and getting back up. Baseball is noted for being a sport in which its best players fail 60 percent of the time. Well, elite skateboarders fail around 95 percent of the time, if they’re lucky.

Here’s Chris Cole performing like the best skateboarder in the world in the 2000s.

This is a classic skateboarding video part. It shows one gnarly miss to remind you that Cole is human, then three minutes of him doing insane stuff that I — a person who can count the number of kickflips I have landed on one hand — can barely comprehend.

But as Cole’s former teammate Jamie Thomas notes in the intro, Cole’s part took about four months to film. A day when a skater lands just one great trick that can make the video is a success. Skaters will often try a single trick unsuccessfully for hours until their body is too sore to continue. Cole was able to film his part in four months because he is an alien; many professionals take an entire year to film a video part they can be proud of.

A more accurate reflection of what it’s like to be an elite pro skater is this video of Cole attempting to land the first 360 flip down the Wallenberg steps in San Francisco. It’s one of the most inspirational things I’ve ever seen — a lesson in persistence and learning from failure, as well as a reminder that getting better at something isn’t always a linear path.

Before the first attempt: Cole rolls up, stops, and takes a look at what he has to jump over. He’s the best skateboarder in the world but this is still a bit intimidating. It’s OK to be scared. Being scared is not an excuse to not do something.

Attempts 1-3: He’s not even close. He kicks the board away well before trying to land.

Attempts 4-10: Progress. It seems like he’s getting closer and learning something every time.

Attempt 11: A setback. Probably his worst attempt.

Attempt 25: Cole yells “fuck,” showing frustration for the first time in the video. If I was there, in person, I probably would have started to think he was going to quit without landing it.

Attempt 27: YO, HE GOT REALLY CLOSE. This is the moment when the camera crew starts to feel like he can actually do it.

Attempt 39: I thought this was the one. I was sure he was going to stick the trick. The WOOs from the camera crew get loud. They have stopped believing Cole can do it, and started believing that he will do it.

Attempts 45-46: Two close calls, more cheering. I’m wondering if the crew feel like they need to pump up Cole as much as they’re excited themselves.

Attempt 54: Cole lands it, technically, but it’s not good enough. He spins around and puts his hands down. He wants a clean roll-away.

Attempt 59: For the first time, we hear what sounds like Cole in some pretty serious pain. I have not slammed myself into concrete 59 times in one day before, but I imagine it feels like shit.

Attempt 67: Cole sticks it clean. It’s the kind of perfect landing you see in polished video parts. The kind that makes you believe that Cole rarely bails, and that the things he does are impossible.

But he had to eat pavement 66 times to get that landing. And to be able to land that 360 flip over the Wallenberg set, he had to eat pavement thousands of times before that, just to get good enough to even attempt it.

If I ever feel like I can’t do something because I’ve failed miserably in the past, I turn on this video and watch Cole fall on his face 66 times before he does the perfect trick.

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