Today’s guest, Guy Kawasaki, flips the usual “success story” on its head with a string of jaw-dropping missed opportunities that became the foundation for a life measured by impact, not just outcomes. In this conversation, Guy takes us from being a kid on the “wrong side of the tracks” in Honolulu to Stanford, Apple, and Canva—sharing how cars, connections, and a few spectacular “what was I thinking?” decisions shaped his relationship with money and ambition.

Guy is a Silicon Valley original. As one of Apple’s first evangelists, he helped introduce the Macintosh to the world. Today, he’s a bestselling author, venture capitalist, podcast host, and a trusted voice on entrepreneurship, innovation, and making a positive difference through your work.

Guy is the chief evangelist of Canva, host of the Remarkable People podcast and author of eighteen books including Think Remarkable. He is an adjunct professor of UC Santa Cruz and trustee of the University of Hawaii Foundation. He was the chief evangelist of Apple, trustee of the Wikimedia Foundation and brand ambassador of Mercedes-Benz. Kawasaki has a BA from Stanford University, an MBA from UCLA and an honorary doctorate from Babson College.

Guy Kawasaki’s journey reminds us that success isn’t defined only by wins, titles, or perfect timing. Missed opportunities, unexpected turns, and “what was I thinking?” moments often shape our values, ambitions, and relationship with money just as much as the highlights do.

If you’re reflecting on your own path—whether navigating career pivots, weighing new opportunities, or redefining what impact and success mean to you—an Aspiriant advisor can help you explore your financial decisions with perspective, purpose, and intention.

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