Why I Dropped Out to Surf the World
Most kids from Punahou School are handed a script: work hard, get into a great college, land a good job. Jack Ho — known across Hawaii's surf world as "Jack From Town" — read that script, applied to the University of Hawaiʻi on his phone during a break between classes, won a scholarship, and then did something almost no one around him expected. He walked away to chase waves across the planet. In this episode of Greater Good Radio, Jack sits down with Evan Leong to talk about the choice that defined his early twenties, the fear and freedom of doing it his own way, and what he's learned about being enough.
The Kid Who Just Wanted to Surf
Jack grew up a short walk from Waikīkī Beach, surfing every afternoon from the age of five. While some of his most talented friends were homeschooled and living in the water all day, Jack went to school from kindergarten through twelfth grade — and spent years feeling like he was missing out. Every day was the same rhythm: class until the final bell, then a sprint to his truck and a drive to the North Shore to catch whatever light was left.
Looking back, he sees that "disadvantage" completely differently now. The classmates, teachers, deans, and lifelong friendships he built at Punahou became the foundation for everything that came after. What felt like a cage in the moment turned out to be a network — one of several "pillars" in his life that, though very different from one another, all connect to the bigger picture of who he is today.
Foiling, COVID, and a Cheap Hand-Me-Down
When Jack was thirteen, hydrofoiling was just beginning to take off in Hawaii, and he was one of only a handful of young people doing it. He couldn't afford the real gear — a new setup ran $2,500 to $3,000 — so he started on a $500 hand-me-down foil and kept posting videos his dad filmed from the beach on a small Walmart camera. Then COVID hit, and the dream he'd always had quietly came true: no school in person, just the ocean, every single day.
That stretch changed everything. He won a team charity foiling contest in Waikīkī, caught the eye of a few brand reps, and landed his first sponsorship — a gear trade with Lift Foils — followed by a paid deal with Olukaʻi footwear. By tenth and eleventh grade, he was making money doing what he loved. He still didn't know if it could last past high school, but the door had opened.
The Hardest Decision: Honoring the Scholarship, or Chasing the Dream
After graduating in 2023, Jack won the Outrigger Duke Kahanamoku Foundation scholarship, which covered a full year of tuition at UH Mānoa. He balanced online classes with surf travel for a year — and then his sponsorships started paying real money, and the pull to travel full-time became impossible to ignore. His dad told him to go for it. His mom, a nervous parent, wanted him to take the safe route, but ultimately gave her blessing: college would always be there.
The part that weighed on him most was the scholarship itself. How could he walk away from an opportunity that generous people had chosen to give him? So he called Bill Pratt, the head of the foundation, and laid it out honestly. Pratt's answer freed him: they'd chosen Jack because they wanted him to learn and grow — and if that growth happened in the real world instead of a classroom, then he should go and do it. That conversation was the push Jack needed. He didn't sign up for another year. He poured everything into building "Jack From Town."
Study Abroad, With No Safety Net
Jack likes to joke that he's doing study abroad — except he's his own principal, his own teacher, and the one booking every flight. Alone in airports in Sydney, Tokyo, and Paris, hauling two coffin-sized board bags and a backpack, he taught himself how to travel: pack light, know your connections, stack airline miles, and always bring a gift for the people who help you out. When something breaks or a flight gets missed, there's no one to call — you figure it out or you don't eat, don't find a bed, don't make it to the wave.
That's exactly the point. While his classmates were on the mainland learning independence in dorm rooms, Jack was learning the same life lessons in foreign countries with no one to fall back on. Booking his own hotels in a language he didn't speak, hunting for an ATM in Indonesia, calling his bank to sort out international fees — every small hardship built the same muscle college was supposed to build. And when he pulled it off, it came with a quiet pride: I can do this on my own. I'm enough.
What Surfing Teaches About Life
Ask Jack for the biggest lesson from the water, and it comes back to opportunity. In the lineup, everyone is watching everyone. The moment you hesitate — pull back from a wave you could have caught — it's gone, and the people around you take note. He's felt that sting of "I should have gone" enough times that it now pushes him over the ledge, on big waves and in life alike. If he has the time and resources, he's learned he'll never regret trying.
He frames every risk the same way: there are only two outcomes. Either it works out, or it doesn't and you learn from it — and both are a benefit, 100% of the time. Whether it's a trip with friends, a dinner with your grandparents, or a job you're scared to chase, the worst move is to let the wave pass. That mindset, forged paddling in terrified from a mile out at sea, is the real thing he brought back from the ocean.
Bringing a Friend Along for the Ride
One of the most meaningful chapters of Jack's story is his partnership with his childhood friend Kainoa, a state track champion who left Babson College after a hard winter on the East Coast. Jack offered him a lifeline: come home, point the camera, help edit, and see the world together. A month later they were on their first trip to New Zealand, and a year and a half in, Kainoa films and edits every video on Jack's Instagram. As Jack puts it, without Kainoa, the brand is nothing — he'd just be a surfer without the footage.
For Jack, watching Kainoa's face light up in a foreign airport for the first time is its own reward. Something he once did alone, he now shares with a best friend who's equally invested in the journey. Together they joke that this is the biggest group project they've ever done — everything they learned in school, applied to real life at a slightly bigger scale.
Being Enough
Underneath the perfect waves and the passport stamps, Jack is refreshingly honest: the glamorous life people see online is not the whole picture. He worries every day about the future, about whether he's on the right path, about whether he's doing enough. But he keeps coming back to one question — are you happy? If you enjoy the work you do and make time to take care of yourself, that's already a win. You don't have to be a surfer or a student; you just have to be doing something that brings you joy.
The people he credits most are his parents, whose unconditional support made his whole life possible. They could have forced him onto the conventional path. Instead, they let go. And that's the message Jack most wants to leave behind — for a younger student, a friend, or anyone questioning whether they're on the right road: you're enough, you're okay, you're in the right place. Sometimes those few small words are all someone needs to keep going, keep learning, and keep chasing the life that's truly theirs.
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