I Beat the Boys: Cruel Jewel Edition with Drew Flowers and Mike Coutu

This week on HappyCast, the spotlight is on cohost Stephanie, who just completed one of the Southeast’s most brutal ultramarathons: the Cruel Jewel 100. Alongside fellow runners Drew Flowers and Mike Coutu, the trio takes us deep into the Georgia mountains and even deeper into the pain cave, reliving the highs, lows, and everything in between. With 105 punishing miles and over 33,000 feet of climbing, this race tested not only their legs but their sanity. Stephanie finished in an impressive 41 hours and 25 minutes, and Drew and Mike crossed the line together at 44:18—and yes, she lets them know who finished first.

From forgotten trekking poles to mid-race trail therapy sessions, the stories fly fast in this post-race debrief. Stephanie talks about running on stair machines and spite, Drew recounts pulling a hamstring in a kids’ street race, and Mike details what it’s like to deal with Crohn’s while trying not to DNF. We get the scoop on hallucinations, aid station carnage, trail naps, revenge runs, mystery runners named “Hugh Jace,” and a certain bear that ate a car door. Spoiler: everyone gets poison ivy, except Mike.

Whether you’re an ultrarunning junkie or just here for the chaos, this episode is full of humor, heart, and hard-earned miles. It’s a celebration of resilience, community, and the weird, wild stuff that only happens when you spend two days running through the woods. And yes—Stephanie beat the boys. Let’s talk about it.

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Have a topic you'd like to hear discussed in depth, or a guest you'd like to nominate? Email us at info@happyendingstc.org