#247 - He didn’t hop on a skateboard until he was 33 and he still calls himself “awful” at it, which somehow makes what happens next even wilder. Moondog Roop (David, if you ask his mom) joins us to talk about thru-skating: combining long-distance skateboarding with the realities of hiking, carrying the board for hundreds of miles, and committing to the kind of day-after-day grit most people only daydream about.
We get into the real origin story, too. Moondog shares what led to sobriety at 27, the rock-bottom moment that forced him to quit making excuses, and how recovery became less about “not drinking” and more about building a life he actually respects. That foundation shows up everywhere in his adventures, from pushing into fear, to staying present on the road, to choosing the next right move even when his body and brain are begging him to stop.
From the Florida Trail to New Mexico, Texas, and the perimeter of Puerto Rico, we unpack what long distance skateboarding looks like when it’s not a highlight reel: headwinds, heat, water carries, rashes, food poisoning, and the constant risk of traffic. Moondog also shares the moments that keep him coming back, like “roadside love,” trail magic from strangers, and the unexpected stop in Madrid, New Mexico that changed the trajectory of his entire life.
If you’ve ever wondered whether it’s “too late” to start something hard, this conversation is your proof that the clock is not the boss. Subscribe for more human stories like this, share the episode with a friend who needs a push, and leave a rating or review so more people can find the show.
To learn more about Moondog check out his Instagram account @gomoondog.
To learn more about me and see clips from past, present, and future shows give me a follow on Instagram @humanadventurepod.
Want to be a guest on The Human Adventure? Send me a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/journeywithjake
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