Leap Academy with Ilana Golan
Guy Kawasaki: The Tech Evangelist Who Built Apple and Canva into Iconic Brands | E97
Thu, 17 Apr 2025
Guy Kawasaki’s journey from a lower-middle-class neighborhood in Hawaii to becoming a Silicon Valley icon is clear proof of grit and transformation. After working in the jewelry business, he pivoted to tech and joined Apple as Chief Evangelist. There, he played a key role in launching the Macintosh, shaping Apple’s brand, and transforming how technology is marketed. Today, Guy is a venture capitalist, startup advisor, and Chief Evangelist at Canva. In this episode, Guy shares his battle with hearing loss, why passion is overrated, his top sales strategies, and advice for scaling a business as an entrepreneur. Guy Kawasaki is a marketing specialist, bestselling author, venture capitalist, and speaker. As the former Chief Evangelist for Apple, he played a pivotal role in launching the Macintosh and now serves as Chief Evangelist at Canva. In this episode, Ilana and Guy will discuss: (00:00) Introduction (02:11) From Humble Beginnings to Studying at Stanford (06:24) Why Sales Is the Key to Business Success (11:01) Knowing When to Pivot vs. Stick with Your Career (17:26) Transitioning from Jewelry Business to Tech (21:48) Key Lessons from Working with Steve Jobs (24:38) How to Evangelize Great Ideas (26:31) The Promotion That Led Guy to Quit Apple (31:58) The Myth of “Finding Your Passion” (38:26) Building Resilience After Hearing Loss (43:15) Strategies to Scale Your Career and Business (49:33) How to Truly Understand Customers’ Needs Guy Kawasaki is a marketing specialist, bestselling author, venture capitalist, and speaker. As the former Chief Evangelist for Apple, he played a pivotal role in launching the Macintosh and now serves as Chief Evangelist at Canva. Despite experiencing hearing loss and receiving a cochlear implant, Guy’s passion for sharing ideas remains unwavering. He hosts the Remarkable People podcast and delivers over fifty keynote speeches annually for clients like Apple, Nike, Google, and Microsoft. Connect with Guy: Guy’s Website: guykawasaki.com Guy’s LinkedIn: linkedin.com/in/guykawasaki Resources Mentioned: Guy’s Podcast, Remarkable People: bit.ly/RemarkablePeoplePod Guy’s Book, Think Remarkable: 9 Paths to Transform Your Life and Make a Difference: https://www.amazon.com/Think-Remarkable-Paths-Transform-Difference/dp/139424522X Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training
Chapter 1: Who is Guy Kawasaki and what is his background?
I quit Apple twice. I turned Steve Jobs down for a third job. So you're listening to a podcast guest who left Apple three times.
Guy Kawasaki, Apple chief evangelist. He helped launch the Macintosh. And since then, he's become this venture capitalist, bestselling author, startup advisor, working with game-changing companies like Canva and others.
The way it works in Silicon Valley is you throw a lot of shit up against the wall. Some of it sticks. You go up to the wall, you paint the bullseye around it, and you declare victory. I hit the bullseye. I hit the bullseye because I am so freaking smart. This concept of finding your passion is vastly overrated. There are only two fundamental processes in business.
Somebody has to make it and somebody has to sell it. Everything else is easy. My advice to entrepreneurs first is.
Guy Kawasaki joining us today, this legend from Silicon Valley, I know you're laughing at me, but that's okay, who I have been following and learning for years. Apple chief evangelist, he helped launch the Macintosh, shaping how we think about innovation and branding.
And since then, he's become this venture capitalist, bestselling author, startup advisor, working with game-changing companies like Canva and others. He's also the host of Remarkable People podcast, really making the world a better place and shining the light on people that are remarkable. Thank you, Guy. It's going to be so fun to have you.
As long as you don't say that I wrote Rich Dad, Poor Dad, I'm happy.
I did not. I know. I already heard like this is one of your. Trust me, I do my homework, but oh, my God. Well, it is a similar last name, though. You have to admit.
Yeah, we all sound alike. We all look alike. It's OK.
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Chapter 2: How did Guy Kawasaki's upbringing in Hawaii influence his career?
Existed. Yeah, yeah.
And I was in a public school system. And thank you, God. One of the public school teachers told my parents to take me out of the public school system, put me in a private college prep system because I had potential to go to college. And again, thank you, God. My parents listened to her and made the sacrifice. And so I got into this school and then...
I honestly cannot remember why, but somehow I decided to apply to Stanford. Because I know today if I applied for Stanford, I wouldn't get past the first reader. I don't think I would get past the, you know, AI they use to make the first screen. So, yeah. So I got into Stanford. I went to Stanford.
But why Silicon Valley? Was that like a dream? Did you know that I got to get out of Honolulu or how was it?
I hate to tell you, but I'm so old that Silicon Valley wasn't Silicon Valley yet. I mean, I came to Silicon Valley in 1972, and it was like Intel and HP, but it certainly wasn't this kind of phenomenon yet. And yet, coming from Hawaii, the scales were removed from my eyes when I landed at SFO because here was a place that... Fortunes, true fortunes were made.
If you're from Hawaii and from Clay Valley, you know, you think you're successful if you run a drugstore or run a hotel or work in agriculture. Not that anything is wrong with those three things, but your horizons are limited by what's in Hawaii. And I come to California and it's like, oh my God, there's like Italian cars, German cars, blonde women, you know, I have found myself.
This is the promised land.
But you started studying psychology, of all things. So first of all, why psychology? Was that something you were drawn into?
Well, there's a deeper story there. So if you were Asian American back then in the 70s, your parents wanted you to be a doctor, dentist, or lawyer.
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Chapter 3: Why did Guy choose psychology and how did it shape his sales skills?
But I will say that one of the sentences that you say pretty often is that one of the best skills is sales and marketing. And I wish somebody was saying that more often because I think it's absolutely true.
You know what? If you come right down to it, there are only two fundamental processes in business. And somebody has to make it and somebody has to sell it. Everything else is easy. Counting it, getting the money, hiring, training. Everything else is easy. If you have somebody who can make it and somebody who can sell it, revenue comes in. And with revenue, as I say, sales fixes everything.
Everything.
Sales fixes everything. No more strategic partnerships. No more strategic bullshit. Sales fixes everything. So in the world, the world, you're either selling or you're making. So I was not an engineer. So I couldn't make. So I had to sell. And it was that simple. And I attribute my success in evangelism and selling. I work for a small jewelry manufacturing company in downtown L.A.,
And this was a manufacturing company owned by a Jewish family. And they embraced me. I don't know why. I mean, I could not be further from Israel than Honolulu, Hawaii. But, you know, whatever. So they embraced me. And basically, I schlepped gold and diamonds for the first five years of my life. And I tell you something, the jewelry business is a very, very tough business. We were a manufacturer.
We sold to retailers. And so we weren't the retailer. We didn't do business with consumers. We did business with businesses.
So you learn patience because you make an appointment with a jewelry store and you fly to Kansas City and the appointment's at 10 and you get there at 9.30 and then all of a sudden it's 11 and they kept you waiting and then they say, okay, so now you can go see our buyer, but the buyer's about to leave for lunch, so you got 15 minutes.
So then you open up your bag and you show your goods and they look at the goods and they say, well, you know, there's five ounces of gold is one carat of diamonds. Diamonds are $300 a carat. 14 carat gold comes out to so much per gram. And so... They're basically reverse engineering. You say you got $300 worth of diamonds. You got $75 worth of gold. Your cost of goods sold is $375.
Because I'm such a nice person, I'm going to let you make 10%. A bargain.
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Chapter 4: What lessons did Guy learn from working in the jewelry business?
Maybe you want to go find a better episode now because why would I listen to this dumbass who left the most valuable company in the world before he made any long-term capital gains? So Let's just put that out on the table. But I will say that for those of you who are now thoroughly confused about whether you should pivot or stick it out, I'm telling you, either way can work.
And like I referred to before in Silicon Valley, the way it works is if you pivot and you're successful, you say, Of course I pivoted. I'm so smart. I came to that realization. And if you stick it out, you say, of course I stuck it out. I knew I was right. But that's how Silicon Valley works. Now, there is a bigger, more important lesson here.
And I think the bigger, more important lesson is whenever you hear a story, you always ask the question, what's missing? And I'll give you a perfect story for this. So, you know, lots of times there's this issue about should I go to college or not? Is a degree worth it? I'm an entrepreneur. I don't need a degree or do I?
And then you listen to some people, Peter Thiel or whatever, and they say, you don't need to go to college. Steve Jobs didn't finish college. Bill Gates didn't finish college. Mark Zuckerberg didn't finish college. Those are three highly successful people. They prove you don't need to go to college. Well, when you hear a story like that, you ask yourself, what's missing?
And what's missing is you've heard three examples of people who didn't go to college and succeeded. Well, what about the people who didn't go to college and failed, which is 99.9999999% of the people? And the flip side is also true is how many people went to college and became successful? Because every Fortune 500 company has a CEO that went to college.
And then you also have to, how about the people who went to college and failed? But you need to ask in that two-by-two matrix of college, no college, success, failure. You cannot just look at the box about no college, success, and conclude failure. That's for me, because the odds of you being the next Mark Zuckerberg or Bill Gates or Steve Jobs is pretty low. I hate to tell you.
I hate to tell you.
I agree. But I think in your book, if I'm not mistaken, it's your last one, Think Remarkable. But I did read most of them, so I could be wrong. But I think you say something that is very powerful, which is quit on a good day. So one of the things that I think is really important is to not look at the slump and
and then decide, okay, I'm giving up, but look at it from a successful point and saying, okay, yes, I can look at this and still with my eyes open, this is not the right place for me and I need to move. And I think this is something I personally like how you say that, Guy.
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Chapter 5: How did Guy transition from the jewelry business to the tech industry?
Talk to me a little bit about what that looks like.
Well, first of all, evangelism comes from a Greek word meaning bringing the good news. So Apple's Macintosh was the good news that made people more creative and productive. And I will now unveil, get a drum roll here, I will unveil the secret to evangelism. And the secret to evangelism is that you evangelize good shit because evangelizing shit is hard, if not impossible.
So now that sounds like a duh, isn't it? Like, God, thank you very much. Until this podcast, I was going to evangelize shit. But now I realize I shouldn't evangelize shit. I should evangelize something insanely great. Thank you very much. You know, what a great podcast.
What I'm telling you, what I'm telling you in a not subtle way is that if you want to be a great evangelist, you have to either create or find or align yourself with something great. Otherwise, it ain't going to work because evangelism is about bringing the good news. And if you have mediocre news, it ain't going to work. So don't try it with something mediocre.
Now, I'm not saying that evangelism is the only way to succeed. There are other ways to succeed. I mean, for crying out loud, Microsoft has succeeded. So that proves, right, you don't have to be insanely great. But for evangelism to work, you have to have something great.
But then you decide to leave Apple and I think you're doing your own ventures, which is a freaking hard guy, but I'm sure it's also helped you shape a lot of the things that I learned from you as an entrepreneur. So first of all, thank you. What were those moments of decision, I guess twice, of leaving Apple and what was it like to start being an entrepreneur?
There are two explanations for why I left Apple, the first time anyway. So one explanation is this. I was the evangelist for Macintosh, and I believe Macintosh was good news. It was a great opportunity. So, of course, Guy would leave Apple to start a Macintosh software company, right? Because if the evangelist doesn't believe in the software market, who will?
So it's expected almost that I would leave. So that's story A. Story B is deeper and sicker and more insipid about me. So at the time, this is 1987. At the time, I was a manager of the group that did the Apple-labeled software developer tech support and Apple evangelism, convincing people to do Mac software. So... I was the manager and the next level up was director.
And the next level after that was VP. And so Apple had this policy that they would buy a director or VP a car. That was, you had to get one level higher than me. So I love cars. I love cars. We could have a whole podcast just about cars and cars. I don't mean like I have to drive a Lamborghini to show off the other people. Nobody needs to know what I drive. I need to know what I drive.
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Chapter 6: What was Guy Kawasaki's experience working with Steve Jobs?
And it's a Venn diagram where you love what you're doing, you're good what you're doing, and you can make a lot of money. And that's your passion, you know, that's your ikigai. And Man, that is a good theory, but I'm telling you that I think that most things start off as an interest. Like I'm interested in social media. I'm interested in podcasting. I'm interested in writing.
The hell if I knew I would become passionate about any of those three things, right? And I would make the case that stop looking for your passion. Just keep your eyes open, your ears open, and your mind open. And when you see things that interest you, scratch that itch. And over the course of a lifetime, you'll scratch a lot of itches. And thank you, God, if some of them become passions.
But don't set off in the world saying, I got to find this passion overnight. I'm in love. I mean... To use a dating analogy, if you tell people, yeah, I decide I'm going to get married, so I'm going to find the passion of my life. I mean, I guess you could do that. Good luck to you, right?
Yeah, good luck to you.
I more advise you to do a lot of sampling.
Experimenting. I totally agree. I mean, that's the same experimentation.
The only way you can figure out your mission in life is by looking backwards. You know, I could tell you right now, looking backwards, that clearly a mission in my life was democratizing things. So I wanted to democratize computing with Macintosh. Right now, as a chief evangelist of Canva, I'm democratizing design.
So you can see this consistency of guy likes to take things that only the elite could do, only the elite could afford, you know, blah, blah, blah.
And now you can do it to others.
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Chapter 7: What is evangelism in tech and how does Guy define it?
Chapter 8: Why does Guy say 'sales fixes everything' in business?
So I would love to hear you because I think a lot of people are trapped in a career that is not suitable just because of the fear of what if I move? What if I leave things behind?
This is one of those kinds of questions that you answer and you hear somebody answer. And you have to understand, you need to be a skeptic when you hear people answer that kind of question because you're only hearing one person's story. There's nothing scientific about my story. There's no controlled experiment.
It's like if you took two people identical to a guy, you put them in an identical program, you give them identical opportunities, and then you see which way is better, pivot or stay. This is not science. There's no control. There's no hypothesis. This is just dog shit luck. But dog shit luck worked out for me.
That works out too.
Listen, I write management books, so I know how much bullshit there is. But for every book that says you got to fail fast, you got to break things, you got to pivot. There's another book that says you got to stick with it. Even when naysayers are telling you it's impossible, you don't believe them, you stick with it because you believe. Well, those two pieces of advice are diametrically opposed.
Do I pivot or do I gut it out? And it depends on which book you read last, right? So when you asked me that question, I don't know what to tell people because for some people you can pivot, for some people you can stick it out. Both ways have worked.
I don't think there's any science to it, but I will tell you that my observation, and this is just one person's observation, is that sometimes it's better to water the grass that you're standing on than to find new grass. And I could make the case that I quit Apple twice. I turned Steve Jobs down for a third job. So you're listening to a podcast guest who left Apple three times.
Maybe you want to go find a better episode now because why would I listen to this dumbass who left the most valuable company in the world before he made any long-term capital gains? So Let's just put that out on the table. But I will say that for those of you who are now thoroughly confused about whether you should pivot or stick it out, I'm telling you, either way can work.
And like I referred to before in Silicon Valley, the way it works is if you pivot and you're successful, you say, Of course I pivoted. I'm so smart. I came to that realization. And if you stick it out, you say, of course I stuck it out. I knew I was right. But that's how Silicon Valley works. Now, there is a bigger, more important lesson here.
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