He Rode His Bike Across South America To Heal - with Ryan Griffin

Ryan Griffin has played Division One baseball, run a marketing team, hand-fed sharks at Sydney Aquarium, and built his own company. He told me all four stories on the same call, and I stopped him twice just to keep the order straight.

From Cricket Country to Division One Baseball

Ryan grew up in Australia, a country where baseball barely registers next to cricket, but he was the kid who threw everything. Toys, rocks, whatever was in reach. His mom signed him up for T-ball around age six, and that was the start of it. He got selected for the Australian Schoolboys baseball team, toured the US and Canada for three months, and picked up a scholarship out of that tour. He ended up playing junior college ball at Clarendon College in Texas, then finished out his eligibility at Lindenwood University in St. Louis. Four years of Division One ball, on the other side of the world from home.

The Career That Nearly Broke Him

When Ryan came back from the US, he landed a job at a digital marketing agency almost immediately, part of the larger WPP group. He was good at it, and he loved it in a way that surprised him. Six a.m. workouts, long study sessions, ten-to-fourteen-hour workdays, and he wasn't burned out by it, he was energized by it. He made director in four years.

Then his body stopped cooperating. He needed surgery. It didn't heal right, so he needed a second one. What followed was a complex wound that took ten months to close. He was largely bedridden, on strong pain medication, unable to move the way he was used to, and he gained roughly thirty-five pounds during that stretch.

The moment that stuck with me most from our conversation was smaller than the surgery itself. Ryan told me about the daily dressing changes, an hour each time, pain medication required just to get through them. During one of those changes, a client called him four times in thirty minutes. He didn't pick up. He told me flatly: "I don't care about your problems." That's the sentence that told him something had to change.

Asking for His Own Demotion

Most guys wait to be pushed out before they admit a job isn't working. Ryan asked for a demotion himself, stepping back from managing a team of eight to doing his old individual role. His company was accommodating about it, which he's grateful for, but the culture around him still pushed back in smaller ways. He started leaving on time, around six instead of the office norm of eight or nine, and got labeled a "part-timer" for it. That was enough. He decided the industry wasn't for him anymore.

A Bicycle, a Breakup, and a Second Health Scare

Once he was cleared, Ryan met someone, and the two of them bought bicycles and set out to ride the length of South America, starting near the top of the continent and aiming for Ushuaia, Argentina, about as far south as you can go on land. Somewhere along the way his girlfriend lost her enthusiasm for the trip and headed home. Ryan kept riding. About a year in, in Peru, he got sick again, lost a significant amount of weight, and had to cut the trip short and fly home.

Sharks, Not Spreadsheets

Back in Australia, Ryan decided marketing was, in his words, "the devil," and went looking for something he actually loved: underwater animals. He worked ad hoc for a couple of Sydney dive shops before landing a job at Sydney Aquarium, first leading tours, then moving into animal care. That meant getting in the water to clean exhibits, check on the animals' health, and hand-feed sharks up to twelve feet long. He calls it a dream job, and listening to him describe it, I believe him.

COVID ended that dream fast. With the aquarium closed to visitors, there was no need to keep the exhibit tunnels spotless, and Ryan was let go. He'd just turned thirty. He was living with his now-wife's parents, applying for roughly fifteen jobs with nothing to show for it.

Building Chunky Duck

Out of necessity, Ryan went back to what he knew: marketing. He reached out to old contacts, picked up freelance work, and within a year had more business than he could handle alone. He partnered with two other freelancers he'd been working closely with, and that partnership became Chunky Duck, now five years old.

What stood out to me wasn't the pivot itself, it was how deliberately Ryan has built the culture inside it. Every Thursday, the fully remote team gives each other kudos through Slack, with small coin rewards that add up to gift cards over time. In one-on-ones, critical feedback comes first, before anything positive, because Ryan doesn't want people bracing for a compliment sandwich. And once a year, every remote team member flies into Ryan's hometown of Noosa, Australia, for a week of workshops, dinners, and Mario Kart. Fifty-one weeks apart, one week together, on purpose.

The One Thing

When I asked Ryan the question I ask every guest, what's one thing our listeners can do today to build deeper connections with the people around them, his answer was about language. He told me his wife will sometimes say she had a "bad day," and he'll push her to get more specific. Frustrated? Embarrassed? Small? He does the same thing with himself and with his friends, naming the actual emotion instead of the vague catch-all. It helps him process what he's feeling, and it helps the people around him know how to actually show up for him.

Ryan's story doesn't move in a straight line, and he'd probably be the first to tell you that. But every turn in it, the demotion, the bicycle, the sharks, the culture he built at Chunky Duck, comes back to the same thing: knowing exactly what you're feeling, and being honest enough to say it out loud.

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Watch the whole episode: https://youtu.be/7PmU86rheEY