Guy Kawasaki Describes Working with Steve Jobs and Other Remarkable People Who’ve Used Optimism as a Strategic Advantage
Release Date: 12/03/2025
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Guy Kawasaki Describes Working with Steve Jobs and Other Remarkable People Who’ve Used Optimism as a Strategic Advantage
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Guy Kawasaki has had an amazing life and career. After growing up in Hawaii, he went to California for college and later went on to what was then known as Apple Computer where he was a self-described “brand evangelist” during some of their highest growth and most entrepreneurial years. He describes Steve Jobs as being optimistic almost to the point of being delusional, and working for him has inspired Guy to be interested in mold-breaking people ever since, hence the name of his popular podcast, . He has also written 17 books on a variety of subjects, his latest being , which...
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info_outlineGuy Kawasaki has had an amazing life and career. After growing up in Hawaii, he went to California for college and later went on to what was then known as Apple Computer where he was a self-described “brand evangelist” during some of their highest growth and most entrepreneurial years. He describes Steve Jobs as being optimistic almost to the point of being delusional, and working for him has inspired Guy to be interested in mold-breaking people ever since, hence the name of his popular podcast, Remarkable People. He has also written 17 books on a variety of subjects, his latest being Wiser Guy, which was released earlier this year.
Chapters:
00:00 Welcome to Blue Sky
Bill Burke introduces Guy Kawasaki as a remarkable guest on Blue Sky, highlighting Guy’s background as chief evangelist at Apple and Canva, and his extensive writing. Guy shares his preference for being a podcast guest due to less prep work, contrasting with the host’s five-hour preparation time.
03:10 From Hawaii to Stanford
Guy recounts his childhood in Kalihi Valley, a lower-middle-income part of Hawaii, and how a public school teacher’s advice led him to a private school, then Stanford. He describes feeling immediately at home at Stanford in 1972, despite it being pre-tech, and the campus’s amazing atmosphere.
06:17 Apple, Steve Jobs & the 1984 Ad
Guy discusses his two stints at Apple, particularly his time in the Macintosh division under Steve Jobs from 1983 to 1987. He reveals the Macintosh team’s mission to preserve democracy and freedom through computing and shares the behind-the-scenes story of the iconic 1984 Super Bowl ad, which the board initially wanted to pull.
11:49 Evangelizing Apple & Sales Skills
Guy details how Apple evangelized its new operating system in the 1980s through fervor rather than just money, contrasting with the corporate image of IBM. He also shares his ‘checkered past’ of dropping out of medical, dental, and law school, leading him to an MBA and invaluable sales experience in the jewelry business, which he considers essential.
17:02 Steve Jobs: Visionary & Demanding
Guy describes working for Steve Jobs as the most formative experience of his career, calling Jobs a visionary and passionate, albeit demanding and intimidating, leader. He emphasizes that Jobs was a ‘mission-driven egoist’ who cared only about making the best computer, disregarding personal biases like race or gender.
23:01 Remarkable People Podcast Origins
Guy explains his decision to start the ‘Remarkable People’ podcast, initially inspired by the lucrative ad model of another podcaster, and his realization that his access to remarkable individuals and business experience uniquely positioned him. He highlights the strategic advantage of having prominent guests like Jane Goodall to attract others.
30:08 Jane Goodall: A Source of Hope
Guy recounts his personal connection to Jane Goodall, stemming from a TEDx interview, and how she became his first podcast guest. He describes her as the most remarkable person he’s interviewed, embodying hope and tireless dedication to her cause, even declining a rest offer at 90 due to ‘too much to do.’
36:30 Optimism as a Strategic Advantage
Guy discusses optimism as a strategic advantage, asserting that it’s crucial for achieving anything significant, combining realism with the belief that challenges can be overcome. He shares his experiences of taking up ice hockey at 44 and surfing at 60, attributing it to a ‘growth mindset’ and the belief that one is never too old to learn new things.