We kick off 2020 with a conversation with Silicon Valley legend and all-around wise guy, Guy Kawasaki. Not surprisingly, he is funny and opinionated in addition to being wise. Guy worked with Steve Jobs at Apple as the original evangelist for the Macintosh computer. Then he went on to a career as an author, speaker and investor. He has written 15 books, a number of them New York Times and Wall Street Journal bestsellers (the most recent is a quasi memoir, Wise Guy). He gives over 50 keynotes a year on the topics of innovation, evangelism and entrepreneurship for brand name companies like Nike, Google and Microsoft. Most recently, he became chief evangelist for Canva, an online design tool.

So how does Debbie know Guy? She met him exactly 20 years ago, in 1999, when she heard him speak at a small business conference. She was so taken with his presentation that she went up afterwards to say thank you and introduce herself. He responded by scribbling a note on a scrap of paper and handing it to her: “Think digital, act analog – Guy Kawasaki. May 25, 1999.” Bingo. Even back then, in the early days of the Web, that hit home. She treasures the note and has thought of Guy as one of her unofficial mentors since then.

Guy is a social media celebrity with 1.4 million Twitter followers. But he’s also a genuinely nice guy, respectful and responsive. When Debbie got an email from him recently announcing his new podcast, Remarkable People, she replied to congratulate him and asked if he’d come on the Gap Year podcast. He responded, “I’d be happy to!”

She was a little nervous about interviewing him so she prepared a list of specific questions. Generally she likes to let the conversation wander a bit more, but this worked out pretty well.

She and Guy talk about:

• his Rule of Ten
• lessons learned from working with Steve Jobs
• the practice of gratitude
• what changed when he turned 60 (he’s now 65)
• the importance of having a growth mindset and continuing to learn
• why you should seek moments of joy (and not eternal happiness)
• his thoughts on the writing process (an obsession Debbie shares with him)
• why he mixes politics and social media
• his positive outlook on life
• how asking simple questions can yield big answers
• his advice for those seeking to reinvent themselves (hint: don’t spend all your time on social media and answering your email)

Be sure to listen to Remarkable People. Debbie’s favorite of the episodes so far are his interviews with Jane Goodall and Margaret Atwood. Both are legends but he manages to walk the line between admiring… and fawning. Debbie hopes she’s done the same in this conversation with Guy.

Mentioned in this episode

• Remarkable People: Guy’s new podcast
• About Guy Kawasaki: an amusing and frank bio
• Guy’s books, including The Art of the Start 2.0 and Wise Guy
• His favorite book on writing: Brenda Ueland – If You Want to Write
• Steve Jobs
• Canva