Professional surfer Jack Ho grew up in Waikiki chasing waves after every school day at Punahou, envious of the homeschool kids who surfed dawn to dusk. Years later, holding a Duke Kahanamoku scholarship to UH Manoa, he walked away from the conventional path to build his "Jack From Town" brand and chase swells across Fiji, Indonesia, France, and beyond. He and Evan Leong dig into the unglamorous reality behind the highlight reels: the airport yard sales of foil gear, the fear of paddling in alone from a mile out at sea, the localism you earn by respecting a lineup, and the parents who told him to do what makes him happy. This is a story about connection, risk, and figuring out who you are when nobody hands you the map. Watch now to see why Jack bet on himself.

Chenoa Farnsworth, managing partner of Blue Startups, sits down with Evan Leong for a wide-ranging conversation that moves from Hawaii's startup ecosystem to the inner life of the people who build it. She traces her winding path from a Big Island macadamia nut farm to health policy in Washington, D.C., to founding Hawaii Angels, Kolohala Ventures, and Blue Startups — and why she turned down a Silicon Valley VC job to raise her kids at home. Along the way she and Evan dig into the shame that quietly powers so many founders, the loneliness epidemic haunting high performers, the sexism that lives loudest in parenting, and a meditation-retreat experience that reshaped how she sees success. Watch now to learn why the whole person — not just the CEO persona — may be the real key to building something that lasts.

Long before Washington, D.C., Ed Case was a kid from Hilo who describes his childhood as "Norman Rockwell, but Hawaii" — the only haole in his class, surfing after school and never once thinking about race or ethnicity. In this wide-ranging conversation, Ed traces the unlikely path from a small-town upbringing on Hawaii Island to the U.S. Congress: the family that left a Kansas law firm generations ago, the culture shock of an elite New England college, the poster on a career-office wall that sent him to D.C., and the lessons he absorbed working for Senator Spark Matsunaga. It's an honest look at forks in the road, close-fought elections, and what it really means to find your passion and chase it. Watch now to hear how staying home shaped everything that came after.

From the deadliest mass shooting in American history to the most devastating wildfire tragedy in modern U.S. history, Chief John Pelletier has spent his career leading through the unthinkable. As incident commander during the 2017 Mandalay Bay shooting in Las Vegas and now Chief of the Maui Police Department during the catastrophic 2023 wildfires, Pelletier opens up about what it actually takes to make life-or-death decisions under unimaginable pressure — and what it costs him personally as a husband and father. He shares the moment his wife told him to leave for a hostage rescue on Christmas Eve, the truth behind the false narratives that spread after the Maui fires, and why officer wellness matters as much as crime fighting. Watch now to learn how Chief Pelletier leads with compassion through tragedy.

Kauai Mayor Derek Kawakami sits down with Evan Leong for a rare, unfiltered conversation about leadership, loss, and legacy. From surviving Hurricane Iniki as a teenager to losing his mother, father, and brother within eighteen months, Derek opens up about grief, mental health, and why he refuses to stay silent about his brother's suicide. He shares how his wife Monica's wisdom shaped his run for office, why he built Kauai's first inclusive playground, and what's driving his campaign for Lieutenant Governor. Watch now to hear why real leadership starts with honesty, not perfection.

Steve Sawyer grew up in a home where silence was the deadliest weapon — and rage could erupt without warning. As founder of the Developmental Trauma Training Institute, Steve draws on his own childhood wounds to reveal how unhealed trauma shapes every relationship, addiction, and behavior we carry into adulthood. From the neuroscience of the nervous system and the four core survival wounds identified by Anna Freud, to the life-changing power of repairing better as a parent, this conversation is a roadmap for breaking generational cycles and reclaiming connection. Watch now to discover why healing trauma isn't about soothing the pain — it's about moving through it.

What if the key to healing trauma, anxiety, and depression has been misunderstood for decades — and the answer lies in a medicine most of us were taught to fear? Mike DeMattos, Chair of the Bachelor of Social Work Program at the University of Hawaii, joins Evan Leong for a deeply honest and wide-ranging conversation about psychedelic-assisted therapy, the roots of self-rejection, and what it truly means to heal. Mike shares how his initial skepticism gave way to compelling research — and how psilocybin, MDMA, and other psychedelics may offer something traditional treatments have struggled to provide: a new way of seeing the world, free from the emotional patterns that have held us back. From unpacking childhood trauma and the "ruminative conditions" that trap us, to the power of IFS therapy and his own deeply personal unburdening, Mike brings both the clinical expertise and the lived experience of someone who has done the hard work himself. Watch now to discover why healing is never a solo journey — and why being whole matters more than being good.

Brad Yates spent six decades coaching elite athletes, leaders, and even legendary college football head coach Bill Curry — and his hardest lesson came from looking inward at his own unprocessed anger. At 84, the former Punahou School educator and high-performance coach sits down with Evan Leong to unpack "Accept Love," his framework for elite performance, why most of what we call passion is actually stored anger, and how grief, fear, and agency intertwine in every leader's life. From getting recruited to Georgia Tech to coaching at Punahou for 30 years, surviving FBI protection alongside Bill Curry at Alabama, and writing a coach's manual at 84, Brad shares the wisdom that only comes from a life fully lived. Watch now to learn why elite performance starts with accepting the work — and why repressed emotions quietly destroy even the strongest leaders.

Scott Simon walked away from a high-paying executive career to become a leadership coach — and the journey that led him there is anything but ordinary. From playing D3 volleyball at Santa Clara after turning down Princeton, to navigating corporate law and a company bankruptcy, to ultimately trading a corporate paycheck for the freedom to build something on his own terms, Scott brings a rare depth of lived experience to every coaching conversation. In this episode, he and Evan Leong unpack the mindset shifts, practical frameworks, and personal turning points that define a life built around continuous reinvention and service to others. Watch now to discover what it really takes to lead — and to let go.

Pal Eldredge has lived one of Hawaii’s most extraordinary sporting lives — from a three-sport athlete at Punahou and a College World Series competitor at BYU, to decades coaching baseball, scouting for Major League Baseball, and teaching fifth grade to a boy the world would come to know as Barack Obama. Evan Leong sits down with Coach Pal for an unflinching conversation about aging, legacy, physical decline, and what it truly means to give back to the game and the people who shaped you. Pal shares raw and moving reflections on losing his brother and sister, raising daughters he’s fiercely proud of, and why the greatest thing a player could ever say is “I learned a lot from that man.” Watch now to hear the honest truth about a life lived fully — and what really matters when the innings run out.