More My First Million episodes

From selling ACs to becoming the tourism king of Jamaica thumbnail

From selling ACs to becoming the tourism king of Jamaica

Published 20 Feb 2026

Duration: 2858

Gordon Stewart's entrepreneurial journey is profiled, highlighting his success building a multi-billion-dollar empire through innovative ventures in air conditioning and hotels.

Episode Description

Get our 140+ business idea database: https://clickhubspot.com/hkf Episode 798: Sam Parr ( https://x.com/theSamParr ) and Shaan Puri ( https://x.com/Sh...

Overview

The podcast explores the entrepreneurial journey of Gordon Stewart, a Jamaican businessman who built a multi-billion-dollar empire through his air conditioning and hotel industries. Starting with odd jobs and a passion for fishing, Stewart transitioned into importing air conditioners in Jamaica, gaining a competitive edge through quick service and installation. He later expanded into real estate by acquiring a struggling hotel in Montego Bay and rebranding it as Sandals Resort, offering a luxury, inclusive vacation experience. His business approach emphasized studying competitors, strong branding, and heavy investment in advertising, which not only boosted his success but also contributed to Jamaicas economic revitalization. His legacy continues through his children.

Additional topics covered in the podcast include Gary Lovemans data-driven transformation of the casino industry, Chinas talent development programs, and reflections on parenting, fear, and personal growth. Emphasis is placed on the importance of exceptional customer service, the role of data in decision-making, and how early affirmations can influence personal success.

Recent Episodes of My First Million

27 Mar 2026 The Skill That Made Steve Jobs Exceptional (and how to learn it)

The text discusses how success now prioritizes emotionally resonant, authentically styled work aligned with "good taste" in the AI era, emphasizing a four-step process to cultivate identity through imitation, historical study, and deliberate creativity across design, culture, and decision-making.

17 Mar 2026 DHH: $100M+ Advice That'll Piss Off Every Business Guru

Recommended: Alternative business strategies that actually work and are possible for small teams.

A company centered on honesty, simplicity, and original thinking rejects conventional advice and Silicon Valley's uniformity, prioritizing education over advertising, embracing constraints-driven innovation, balancing intuition with data, and emphasizing long-term resilience, authenticity, and independence in navigating modern business challenges and AI's evolution.

More My First Million episodes