In this episode of HappyCast, we welcome ultra runners Chuck Clark and Ben Bridgeman to recount their epic (and sometimes disastrous) attempt at running two brutal 100-mile races just two weeks apart: Outlaw 100 and Lovit 100. What started as a simple challenge turned into a saga of icy wipeouts, brutal climbs, poor life choices, and a whole lot of stubbornness. From navigating Jeep roads littered with boulders at Outlaw to dealing with a brand-new course layout at Lovit, the guys break down the highs, the lows, and everything in between—including the moment when Ben took an all-time classic fall that had his friends doubled over in laughter.

With course changes, extreme conditions, and the mental battle of pushing through back-to-back races, Chuck and Ben share their strategies (and mistakes) in managing fatigue, staying fueled, and making sure they crossed the finish line. Along the way, they discuss why pacing each other sometimes feels more like a competition than teamwork, why the smallest aid station breaks can kill your race time, and what it’s like watching your friend’s race completely fall apart in real-time.

Plus, we debate the age-old ultra-running question: Is it better to go out fast or play it safe? And, of course, no episode is complete without some well-earned roasting, a look ahead at future races, and the latest Can’t Let It Go segment. Tune in for an episode filled with laughs, lessons, and the kind of suffering only ultra-runners willingly sign up for!

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