When life forces you to grow up fast, grit becomes part of your DNA. In this episode of The Climb, Teko Bailey sits down with entertainer, storyteller, and cultural voice Lanai Tabura to trace the journey from a pineapple field on Lānaʻi to award-winning media creator. Raised in poverty by a single mother, shaped by back-breaking plantation work, radio hustle, and the responsibility of cooking for his brothers at age twelve, Lanai’s story is a case study in resilience.

He unpacks the realities of growing up without a father, why hardship became his greatest teacher, and how the plantation generation built the foundation of Hawai‘i’s modern culture. From picking pineapples in 120-degree fields, to building one of Hawai‘i’s most influential radio stations, to hosting global food shows and winning Emmys, Lanai shows how a tough childhood forged the discipline, drive, and creativity that fuel his work today.

Lanai and Teko dive into the pressures of entertainment, the evolution of island music, and the science behind radio that most people never hear about. He talks candidly about fatherhood, the weight of modeling healthy communication, and why telling your kids “I love you” can change the trajectory of their lives. They explore the responsibility of carrying ancestral stories, the importance of cultural preservation, and how travel, food, and storytelling became his way of honoring the people who raised him.

This episode is for anyone grinding their way forward, anyone pulled between culture and ambition, and anyone who needs to remember that tough beginnings don’t disqualify you—they shape you.

(00:00) Why Hard Work Built His Life

(03:00) Growing Up Poor on Lānaʻi

(06:00) Pineapple Fields, Pain, and Grit

(09:30) Plantation History and Hawai‘i’s Melting Pot

(12:30) Radio Beginnings at Sixteen

(15:00) Music, Artists, and Building Island 98.5

(18:40) Family, Fatherhood, and Modeling Love

(22:10) Anthony Bourdain, Food, and Storytelling

(25:00) Creating Shows and Global Travel

(28:10) Preserving Culture and Helping Local Businesses

(31:00) Success, Responsibility, and What Matters Now

Lanai Tabura is an Emmy Award–winning producer, radio host, actor, culinary storyteller, and creator of Cooking Hawaiian Style, now in its 22nd season. Born and raised on the island of Lānaʻi, he has built a multi-decade career in television, radio, travel media, and food culture. His work includes The Great Food Truck Race, documentaries such as Ramen Yokocho, TV hosting across Asia, and pioneering the launch of Island 98.5, one of Hawai‘i’s most influential island-reggae stations. Lanai’s passion is preserving Hawai‘i’s culture through food, travel, and storytelling while helping local artists and businesses thrive.

Instagram: @lanaitabura

About Teko Bailey

Teko Bailey is a husband, father, coach, and guide for men walking the path of faith and purpose. Through The Climb, he’s building a brotherhood of men committed to living fully, leading boldly, and climbing with intention.

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