Pizza, Pain, and Perspective | Fireside Chat Guest: John Calabrese

What do pineapple pizza, the Barkley Fall Classic, and Oreos have in common? For most everyday athletes these are part of their endurance journey. John Calabrese, known in the endurance world as Breezy Trailhead, is no different. Each of those are pieces of the larger puzzle that make up his raw, real, and relentlessly human endurance journey.

In the latest Fireside Chat on Run Tri Bike, host Jason Bahamundi dives deep into John’s story, a tale stitched together by hardship, humor, and a whole lot of heart. Whether he’s toeing the line at JFK 50 or debating pizza toppings with fierce conviction, John reminds us why we fell in love with running in the first place: because it makes us feel more like ourselves.

Turning Pain Into Purpose

Long before he was running back-to-back ultras or pacing friends through the night, John was navigating personal darkness. A difficult divorce and chaotic lifestyle might have derailed his path. That was until running gave him something solid to hold on to. Inspired by the military’s Physical Readiness Test and driven by an inner need for change, John turned pain into momentum.

His ultra resume is as rugged as it is relatable—DNFs, tough finishes, and moments of madness like running a marathon in a trash-bag costume as Bradley Cooper. But his message is clear: it’s not about always finishing strong. It’s about showing up, again and again, for yourself.

Mindset Over Miles

Now 45, John’s training looks different, but the fire still burns. Hip and knee injuries have shifted his focus to swimming, cycling, and strength training, but his mindset remains adaptive. Instead of chasing rigid metrics or PRs, John listens to his body, makes space for joy, and embraces every season of his athletic life.

His philosophy? Fitness isn’t linear. The best version of ourselves doesn’t come from perfection. The best version comes from persistence, perspective, and play.

A Heart for Community

John’s story truly comes alive in the way he gives back. After meeting Donald Harms, a young athlete competing in a racing chair, John stepped into a caregiver role, forming a friendship that’s impacted his entire family. Through grassroots events and Ainsley’s Angels, he’s become a passionate advocate for inclusion in endurance sports.

That spirit of connection runs deep. Whether it’s through aid stations serving up cheesesteaks or quirky low-cost races like Jarman’s Invitational (hello, 9,000 feet of elevation), John thrives where community and chaos collide.

Fueling the Fun: Food and Nostalgia

What’s a run without some legendary snacks? John shares his ultimate aid station go-tos—from Red Vines and Dr. Pepper to frozen York Peppermint Patties and cookie dough ice cream. He’s nostalgic about the Pizza Hut Book-It program and loyal to Double Stuff Oreos.

His lighthearted food takes are more than comic relief—they’re a reminder to bring fun, flavor, and authenticity into every part of our endurance journey.

Stay Human, Stay Inspired

John Calabrese isn’t a conventional athlete and that’s what makes his story so compelling. It’s messy. It’s funny and inspiring in all the right ways. His journey from heartbreak to healing, from Barkley to Book-It, speaks to the everyday athlete in all of us.

Training for your first 5K? Maybe your tenth ultra? As an everyday endurance athlete on your own journey remember John’s story. He will inspire you to run with your heart, laugh along the way, and never underestimate the power of showing up—snacks in hand.

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