He fainted in a hospital hallway. Quit law school after just two weeks. Got robbed—twice—on his way to high school. And for a while, he sold jewelry just to pay rent. So how did that guy end up helping Apple launch the Macintosh, becoming one of the most influential voices in tech, and helping Canva grow into a global design powerhouse?

In this episode, I sit down with Guy Kawasaki, a man whose life defies the clean-cut success stories we often hear. Born and raised in Hawaii in a lower middle-class family, Guy’s journey took off not because of privilege—but because of grit, curiosity, and the occasional wild twist of fate.

We dig into the pivotal moments that changed everything: the joyride in a Porsche 911 that sparked his ambition, the winding road through college majors and a short-lived attempt at law school, and the serendipitous friendship that opened the doors to Apple—no résumé polish required.

We also talk about his career after Apple: from venture capital to writing bestselling books, and most recently, his work with Canva—a company that reignited his passion for democratizing access to powerful tools.

Whether you’re just starting out or feel like you’ve taken a detour, this conversation is a powerful reminder that success isn’t linear—and the messiness might just be the point.

In this episode: 

• (00:00 ) Growth mindset & grit
• (12:41 ) Dropping out & MBA journey
• (15:09 ) Sales experience & Cutco lessons
• (20:58 ) Networking, relationships & “nepotism”
• (25:04 ) Working at Apple & Steve Jobs
• (39:29 ) Signal platform & secure communication

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About Our Guest

Guy Kawasaki is a marketing executive, author, speaker, and entrepreneur best known as Apple’s original Macintosh evangelist and Chief Evangelist at Canva. A psychology major turned tech visionary, Guy helped define how products get adopted and movements are built. He’s written 17 books including The Art of the Start, Enchantment, and Think Remarkable. Today, he hosts the podcast Remarkable People and continues to inspire creatives, marketers, and entrepreneurs around the globe.

Guy Kawasaki

• Guy Kawasaki's Website
• Guy Kawasaki LinkedIn
• Guy Kawasaki YouTube
• Remarkable People Podcast

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