Leadership, Endurance, and the Team Behind Every Effort

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Borrowed & Learned

Over the past few years, I’ve read a bunch of books by endurance athletes recounting their journeys of taking on seemingly impossible challenges. Most recently, I finished Iron Hope by James Lawrence. Known as “The Iron Cowboy,” he’s broken multiple Guinness World Records for endurance racing—including 50 triathlons in 50 states over 50 consecutive days.

But this book focuses on his most ambitious feat: the Conquer 100. From March 1 to June 9, 2021, he completed a full-distance triathlon each day—a 2.4-mile swim, a 112-mile bike, and a 26.2-mile marathon run. That’s 140.6 miles per day for 100 straight days, totaling 14,060 miles in just over three months.

Stories like this always highlight themes like discipline and mental toughness, but what also stands out is something less obvious for a solo endurance challenge: the role of a team. Even in the most solitary pursuits, athletes rely on support systems—coaches, family, friends, and teams who help them perform at their best. In Iron Hope, Lawrence has friends pacing him, a physical therapist keeping his body in check, and most critically, his wife, Sunny. She’s not just the mastermind behind the logistics—she’s also the one who won’t let him quit. Even when Lawrence feels like he has nothing left, or others think stopping is the logical move, she refuses to let him give up.

I haven’t taken on anything nearly as extreme as these ultra-endurance athletes, but the fitness events I’ve pursued have required my version of intense commitment and hard work. And in any physical pursuit—especially those without a tangible reward at the end—it takes a certain kind of motivation to keep showing up. I’ve learned that falling in love with the process is the only way through, no matter how hard it gets.

But while it’s on me to wake up early and train, to stay disciplined with nutrition, rest, and preparation, my wife Dana has been there every step of the way—working with me to make it work. We’ve found a good balance in sharing responsibilities, each carrying our weight, but the reality is it would all be a heck of a lot more challenging without her flexibility, support, and understanding.

One of my favorite moments from my first marathon last year was spotting Dana and Mylo cheering on the sidelines. I’d feel completely drained, but the second I saw them, it was like a surge of energy that carried me forward for the next few miles. I couldn’t pinpoint what gave me that extra push in the moment, but looking back, I think it was perspective. Seeing them zoomed me out from the pain of the race and reminded me of everything that had led to that moment—the work, the trade-offs, and most importantly, why I was out there in the first place. Events like this are milestones in the never-ending pursuit of testing my limits and pushing toward the best version of myself. Someone who, as I get older, can continue to be an asset to my family—not a liability.

After finishing Iron Hope, I started thinking about how this shows up beyond fitness—how the same perspective and support applies to leading the team at Barrel.

This year has already felt like a race. There’s no finish line I’m chasing, but every day is about keeping the pace. Whether it’s real pressure or just what I put on myself, I feel it—to keep moving and build momentum.

A couple of weeks ago, I came into my weekly one-on-one with Peter (Barrel’s co-founder/CEO, now leading Barrel Holdings) feeling like I was at mile 20 of a marathon—motivated but carrying the weight of everything behind me and in hindsight, looking for the fuel for the next push forward.

I shared what was on my mind: all the moving pieces, the recent challenges, the effort to give everything the attention it deserves. New business conversations have been slow, and while I feel optimistic about what we’re building, I’m constantly learning how to navigate the ups and downs.

Talking with Peter was a bit like seeing Dana and Mylo on the sidelines—an energy boost. He reminded me of our progress—for instance, just over a year ago we were talking about going all-in on CPG and set a goal of adding 10 new clients to our roster. In 2024, we exceeded that and tomorrow, we'll be leading a panel discussion at Expo West.

We also fleshed out ideas I’d been working through and, more importantly, created space to step back and see the bigger picture. In any endurance event, you might start with a goal—crossing the finish line or hitting a certain time—but as the race unfolds, it quickly becomes about taking the next step. That mindset keeps you moving forward, but every so often, you have to look up and recognize how far you’ve already come. The real work happens before race day—the effort, the preparation, the right inputs during training.

I’ve worked with Peter and Sei-Wook, Barrel’s other co-founder, for almost 12 years. Stepping into the CEO role in June has been an exciting new chapter, that’s also required an adjustment. Leadership, like endurance sports, requires a deep level of intrinsic motivation. There’s a weight to the responsibility, the pressure to make the right calls each day. Despite being surrounded by a team whose dedication and drive consistently impress me, it’s easy to feel like it’s all on me. In his book, Scale at Speed, Felix Velarde describes it like this:

"Leadership can be a bit lonely. Which is peculiar, since many leaders are extroverts. To their friends on Facebook they seem invulnerable, motivated, successful and popular. The famous loneliness at the top is not about the glory; it’s about the responsibility. It’s about the fact that ultimately the decisions have to rest on the shoulders of the leader, noone else. It is you who has to hear the worst, to deal with the crises, to fire the popular laggard or patch up the client’s ego. It’s all on you. The worst thing is, you can’t share the stresses and strains. There is no-one you can offload to."

Grateful to have Peter and Wook as sounding boards and partners, reminding me that decisions may fall on me but I have their support whenever I need it. And of course, to our leadership team, who is always read to dive in to new initiatives and work together to make progress.

There's plenty more I could write, but what I want to say is—whether through endurance sports, leadership, or life—discipline and intrinsic motivation are required to progress and to show up, especially when the going gets tough. But having people in your corner—to see the bigger picture, to talk things through, and just be there—can make all the difference.