Billy Mann is one of my favorite people—and that’s not just a casual statement. I’ve had the pleasure and privilege of knowing Billy for the last few years, having been introduced by his wife Gena, a childhood friend of mine.
To simply list his accomplishments—Grammy-nominated songwriter, publisher, producer—feels reductive, though impressive. He’s also a devoted husband, father, and passionate Philadelphia Eagles fan. But what truly sets Billy apart is his generous spirit and thought-provoking nature that has made him one of the most genuine individuals I’ve met.
As one of the earliest guests on our podcast, Billy shared a mantra of his that helped to reshape my perspective on midlife: “Chase the hit life, not the hit song.” It’s this kind of maturity that exemplifies who Billy is—someone who consistently pushes himself to grow emotionally, physically, spiritually, and creatively.
Recently, Billy undertook a really cool journey; a guys’ trip to Guatemala. When he shared a recap of his experience with me, I was touched by both the challenge he embraced and the deeper meaning behind it. As someone who strongly believes in the value of “the guys trip”; it’s a full chapter in my book —whether through physical challenges like hiking mountains, or my recent trip to Naples with my fraternity brothers which consisted of nothing more than boating, pickleball (yes, I played), great meals, and big laughs— Billy’s experience landed with me; and I just enjoy learning about new things and maybe add them to my list.
Billy’s detailed account of his Guatemala expedition—from his friend Dan who organized it for his 60th birthday, to the lessons learned and the bonds formed with his fellow travelers—was so compelling, somewhat scary and pretty fuckin funny, in a “we survived” kind of way, that we invited the entire group onto a Zoom call to record a podcast episode, which I’m excited to share with y’all soon.
Billy sees things through a unique lens – his viewpoint, perspective, and philosophies shapes his artistry and how he interprets the world around him. In this edition of “How I See It,” I’m honored to share the insights of my friend, Billy Mann, a man who truly embodies what it means to not only chase the hit life, but to actually be living and enjoying it. This interview combines a post he sent me and our conversations about the trip.
How I See It, with Billy Mann
MLM: Conversations like this inspire me. A few years ago, I never would’ve imagined doing this—sitting down on a Monday morning, talking with someone like you. It’s incredible. And of course, I’m dying to know why you decided to get on board with this insane Guatemala trip?
Billy Mann: Last year, my friend Dan invited me to join him and a group of his pals for what he called a “not a joke” Guatemala Trek. The plan was to travel to a remote Mayan country and hike 8 or 9 miles a day, mostly…UP.
I thought I understood what “up” meant, but I learned very quickly that I did not. By the time I was shortening my walking sticks to negotiate the space between climbing and crawling—for hours—I was wondering why anyone would consider this a leisure activity. By the first hour of the first day, I was already asking myself existential questions like, “Why am I not on my couch waiting for UberEats to bring me sushi?” But there I was, at 7,000 feet, dizzy from the altitude and breathing in a thin air cocktail of orange, earthy dirt, volcanic ash, and whatever else nature decided to throw my way.
MLM: Just you versus nature. How difficult was that first day overall?
Billy Mann: Grueling. None of us copped to the agony of that first day, that first hour, or the mental negotiations we were all silently having between time and benefit. We were a group of a dozen men—mostly Americans, plus a Swede, a Brit, and an Israeli—brought together by Dan. Different backgrounds but all successful, Type A, achiever types. No one was going to complain or whine. Light encouragement? Sure. But we were not the empathetic type. We even had two ranking soldiers among us, and only one musician. This was not a group for glamping.
At night, temperatures dropped into the 30s, and we huddled around a teepee firepit to reflect on the day. Guides handed us hot water bottles—“babies,” we called them—to keep warm. It was so cold, we clung to them like lifelines. Around the fire, I strummed a guitar, which anchored me in a way nothing else could after hours of endless climbs and descents, surrounded by brush, ash, and the humbling reality of aging bodies. That first night, I finally drifted off to sleep when I heard a growl outside my tent.
MLM: A growl? Oh shit. What happened with the growl?
Billy Mann: Startled awake, I held my breath. This growling sounded ferocious. I was convinced a wolf—or worse, a jaguar—was right outside my tent. I grabbed one of my walking sticks and retracted it into a spear-like weapon. “Great,” I thought, “I have to kill a wild animal now.” Armed with my headlamp and “weapon,” I unzipped the tent, crouched down, and stepped outside into the pitch-black night, my heart pounding like a techno beat.
I spun around, shining the headlamp in every direction. Nothing. I hissed to scare whatever it was. Nothing. Finally, I stood to pee, and there it was again—the growl. Louder this time! I spun around with my walking stick, ready to fight for my life. And then…I realized the terrifying beast was the Swede in the adjacent tent, snoring like nothing I’ve ever heard. So much for my Indiana Jones moment. I confessed the ridiculous episode the next morning and got some good laughs.
MLM: What surprised you about the trek?
Billy Mann: Over the days, I got to know Dan’s friends—people I likely would never have met in my day-to-day life. We shared stories about families, habits, and experiences. Nature has this way of mentally lubricating conversation, and standing eye-to-eye with a volcano as it erupts does wonders for perspective.
The most humbling moments came from the locals. Mayan villagers, some as old as 70 or as young as 7, would pass us wearing sandals, carrying heavy stacks of wood or baskets of supplies, moving effortlessly while we labored in our fancy hiking boots and daypacks. They weren’t nearly as tall as us, but they moved like they were floating.
MLM: Did you face any unexpected challenges?
Billy Mann I got food poisoning the first night, which was not ideal for a trek with no bodega for Pedialyte or urgent care. I felt self-conscious about holding the group back and being perceived as weak. But I pushed through, swallowing my embarrassment when my condition caused delays. It was a tough balance—wanting to be strong while knowing my body had other plans.
MLM: What did you take away from the experience?
Billy Mann: Dan gave us all the gift of shared humility. We were all tested. We all shivered and raged at the freezing roosters at 3 a.m. We all learned to appreciate the small things—a Goo energy pack, a beef jerky stick (arguably the best thing ever), or in my case, stomach medication.
The trek wasn’t just about pushing through physical challenges; it was about understanding privilege. Seeing the disparities in the Mayan villages—the lack of air conditioning, dentistry, or basic amenities—put my own life into perspective. And then there were the kids. Their bright, smudge-faced smiles in traditional, colorful dresses were like jewels against the earthy green and brown backdrop of Guatemala.
MLM: How did it all end for you?
Billy Mann: By the last morning, my food poisoning had worsened. I called my doctor, hoping he’d clear me to continue, but his response was, “If you were my brother, I’d say, ‘Don’t be an idiot.’” I packed my things and said goodbye to the group, singing one last song around the fire. It was tough to leave, but it was the right decision.
The group checked on me afterward, bringing Gatorade and sending supportive texts. The bonds we built were incredible. This trek was a reminder of how good humans can be when we let down our guard and work together. It also left me reflecting on how easily we “other-ize” people and cultures. In Guatemala, I saw the best of humanity—shared stories, humility, and unprompted compassion.
