Miles Kipper Interview July 1st 2023. From the Road.

Interview with Miles Kipper:

It’s day 11. We’re staying the night in Dubois, Wyoming. Probably the most beautiful town yet. But Wyoming is definitely the least forgiving state we’ve ridden through.  Lots of elevation, poor pavement, hills, falls, heat, rain. On the flip side, the people are super friendly and there’s a great vibe here. We don’t have much time to explore off the path, but I’d like to come back and spend time here after the trip.

Miles Kipper

It’s challenging to think back on the trip since everything blends together into one giant skate session.  The other day we we’re trying to think back on where we had stayed over the trip and no one was able to recall more than a day or two.  That said, here’s a bit of what we’ve been going through:

It was a really fun first week, burning through whole states in a day. Watching the terrain change. One highlight was the initial pristine bike path.  Another was coming out of Ohio we had about 10 miles of straight straight road that was amazing.

country road

Another thing that sticks out is the locals we’ve met along the way.  The stories we’ve heard and told.  On one of the first days we stopped in a little valley in West Virginia.  I had my camera out and this guy walks out to the road with cowboy boots and a 45 strapped to his hip. He comes out yelling that he doesn’t like cameras and what are we doing here.  We got to chatting and he ended up being really friendly. Turns out he’s a firefighter but he’s getting sick of his town because it’s getting too big now that it has 100 people.

Hey, there’s a bad ass double rainbow starting right over me right now. 

(Just then a Tornado siren goes off. None of the guys seem to know what to do about that in a motel in a small town, but after a minute the siren turns off).  

I’ve driven recently across the country but it’s so different to be doing it on a skateboard.  You hear the windmills. We’ve averaged about 190 miles a day. We’re each skating 5-7 hours a day every day. It’s super different than on a controlled course.  There’s traffic, crappy roads, crappy weather.  Dirt roads, construction sites. Everything except for snow.  30 mph headwinds one day.  That was a rough day.

As for the team dynamics, It’s been really cool.  The first few days were a bit intense but we figured out how to communicate.  We all got sick as hell (the Vandemic), but we got through it.  Paul and Andy are super hardcore, but Jack wants to make this an adventure and a healthy experience. It took Jack a little while to get a sense for the caliber of the riders and it took Paul and Andy a bit to figure out Jack’s rhythm.  But it’s come together and it’s flowing.

push crew

Jack is impressive.  He’s done 4 push trips, an eskate attempt, and at least 7 or 8 vehicle trips.  He’s seen more of this country than anyone I’ve ever met.  He’s got stories about everything and his life is super interesting.

Dylan didn’t stand a chance to not be a skateboarder with a dad like Jack.  He’s a badass skater in his own right and he’s been an incredible navigator. He’s also been keeping us all balanced.  Jack and Dylan are an amazing dynamic duo.

Paul’s a unique individual. I’ve really enjoyed getting to know him.  He’s great. His brain works in mysterious ways.  And he’s an amazing skater.  

Rick is the oldest skater on the team at 57.  He’s a former runner and the only one legged pusher–but he’s generally using a paddle.  He’s been more than keeping up.  He had at least one 100k day! He’s also been keeping a handwritten journal of the trip and he’ll be the only one that’s gonna remember the actual details.  He’s super solid.  Doesn’t miss a beat.  Super inspiring to me.  Rick has great quotes.  Every day there’s a new one:  today was “shred till you're dead”.  And he’s fast.  Beats me on anything under 20 miles.  I’m super inspired by him (and the stories of his adventures with his lady Wendy).

I was so busy prepping for this trip.  We worked so hard to get to this point.  Preparation, training, and personal work.  But once it’s started you need to slow down and be present.  Here I am, doing something I love all day, everyday.  Sometimes really not loving it, but then turning a corner and the cross wind becomes a tail wind.  You never know what’s around the corner when you’re making the space for it.  It’s life distilled.  Life happens. Sometimes it’s hard, sometimes it sucks. But keep the mental positivity and just push through till you crest the next hill. Sometimes you go from pissed to Nirvana.

The skate side of things: I’m getting stronger every day after the first few days. We’ve all become skate machines.  Mentally it’s also been great.  But it’s living in a van with 6 dudes so it is what it is. 


As for skating technique: I’m a way better pusher than I was two weeks ago.  I learned how to push uphill, especially watching Paul and Andy push. They are both so economical. And Andy’s fit fit.  With Paul you see him pushing from his head all the way through to his toes.  It’s taught me a lot.  I’m engaging way more of my body, my big muscle groups, especially in my push.  I’ll never skate the same. I’ve been doing it wrong my whole life.  

But now I’m fitter than I was and faster than I was, and this will be helpful for my personal distance skating going forward.

The mental gymnastics of knowing there’s a support vehicle changes things.  It allows you a mental out that’s different than doing a personal distance skate.  And that allows me to push even harder. But personal distance everyday is a bit about the luck of the draw and depends on the roads and conditions. 

People have been coming out of the woodwork. Tons and tons of love and support.  From old friends and random strangers. 

Jack was very intentional about picking the 4 of us.  I’m really interested in why.  There’s definitely faster skaters than Rick and I, but we’re super stoked to be part of this. It’s allowed me to push the envelope of what I thought I could achieve.

This has been and continues to be the longest most epic skate trip ever. And, once again, it's an honor to be a part of this.

But after this trip I’m gonna hide my skateboard in a closet for a week.

To follow the team visit:

Instagram – @thepushskaterelay

YouTube - @ThePush-SkateAcrossAmerica

Facebook - The Push A Skate Relay Across America

And here's a bio on Miles Kipper:

Miles Kipper is a Minneapolis based skater with more than 20 years of longboard experience. He is the cohost of the long boarding podcast, LDP Cast and the current record holder at the 24 hour Miami UltraSkate in the Men’s Clydesdale division. He has been an active member of the LDP community since 2019 and has taken part in or helped plan skate events all over the country. He is a storyteller and works to bring the community together whenever possible. He is honored and stoked to be part of the Push relay team.

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