Leap Academy with Ilana Golan - Guy Kawasaki: The Tech Evangelist Who Built Apple and Canva into Iconic Brands

Episode Date: April 17, 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

Wow, this show is going to be incredible. So buckle up and I'm sure you're going to enjoy it. But before we get started, I want to ask you for a favor. See, it's really, really important for me to help millions of people elevate their career, fast-track to leadership, land dream roles, jump to entrepreneurship or create portfolio careers. And this podcast is all about enabling this for millions of people to see a map of what it actually takes for big leaders to reach success.

So subscribe and download so you never miss it. Plus, it really, really helps me continue to bring amazing guests. Okay? So let's dive in. 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 Conva 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 victories. 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've 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 Conva 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 okay. Take me back in time, Guy. You grew up in Hawaii, if I'm not mistaken, kind of a tougher part of Honolulu. So you didn't come from a lot of money. No, I did not. I did not grow up in Mar-a-Lago, no.

So tell me, how did you grow up? I grew up in a lower middle income neighborhood in Hawaii. It's called Kalihi Valley. And if you know anybody from Oahu or Honolulu and you say you met a guy from Kalihi Valley, the first question out of their mouth might be, well, did he hijack you? Did he pull a gun on you? Did he pull a knife on you? And so that's the kind of place I grew up.

It was a very, very diverse community. Oh, can I say diverse anyway? These days, right? We were DEI before DEI was a thing. 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 AI they use to make the first screen. So yeah, so I got into Stanford. I went to Stanford. Incredible.

But why Silicon Valley? Was that like a dream? Did you know that I got 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 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, you know, fortunes, true fortunes were made. If you're from Hawaii and from Cali Valley, you know, you think you're successful if you run a drug store 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. Oh, me too.

Trust me. Doesn't matter. I have two options. And marry a nice Jewish girl. Yeah. Exactly. Right. And so I took this course where you went on staff rounds at the Stanford Medical Center.

I swear to God, in the first class, I fainted. So I figured, okay, that takes out medicine. And then I thought well maybe dentistry but then I'd read an article that dentists have the highest rate of suicides. I said no there goes dentistry so all that was left was law and my father was a state senator in Hawaii so he would have loved if I had a law degree. He never went to college so I went to law school and oh wait we're we're backing up, backing up. How did I get a psych major?

I got a psych major because at the time at Stanford, psych major was the easiest major you could find. I had a very rigorous selection process. I'm like, what is the easiest major? Psychology, sign me up. I went to law school for about two weeks and I quit and I just couldn't stand it.

I mean, it was like too tough on my fragile ego. Or the way I look at it now is that many lawyers take 20, 30 years to figure out they're miserable. I did it in 20 days. So that's how much smarter I am. So you were already entrepreneurial and you were already experimenting. That's how I see it. Well, I mean, listen, I'll tell you something about Silicon Valley. 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 victories. I hit the bullseye. I hit the bullseye because I am so freaking smart. I hit the bullseye. I hit the bullseye because I am so freaking smart. I hit the bullseye. So you're wondering why this story applies to my career. So yeah, I can say I look back and I said, yeah, I decided I wanted to be in sales and marketing. So I majored in psychology because I knew psychology, social psychology, behavioral psychology would help me in the rest of my career. And if you want to believe that, God bless you.

But I'm telling you, the reason why I picked psychology, psychology was the easiest measure. It is that simple. 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. 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. 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 LA. 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 golden diamonds for the first five years of my life. And I'll 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. And 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 is 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. They 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. Yeah, so now you can get $400 from me and I need 90-day no interest dating because I'm not going to pay you right away and And I need delivery in two weeks. And then, and that's the good news. That's if you got an order, if you didn't get an order, you went to Kansas city for nothing.

So basically I learned sales in that kind of surrounding hand to hand combat. Which if you tell that to most Gen Z people who say, this is what sales is like, you're sitting in an office outside the door. You're waiting for an hour. You get 15 minutes. Somebody throws your goods on a scale. They figure out the cost of goods sold and the scrap value. And because they're kind to you, they're going to give you 10% over scrap value.

That's what sales is like, not this bullshit. Let's do A-B testing on our way of sight. Is the purple border more effective than the red border? Do we get more clicks with this? Do we get more clicks with that? Should we put the button at the top or the button at the bottom? That's not sales. I love that and I can already see my next question when you get to Apple. But before that, you considered law school, but also realized that this is not for you. So what was that moment that you decided to pivot? And I think you talk a little bit about sunken costs when you talk about this. 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 dogshed luck, but dogshed luck worked out for me. That works out too. You could conclude, listen, I write management books.

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 then 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.

So when you ask 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 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. Or what about the people who didn't go to college and failed, which is 99.999999% 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 hop out 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, 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 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. I think that's absolutely true. And I'll give you a sort of a related theory that I learned from Angela Duckworth, who

is the mother of grit, MacArthur Fellow mother of grit, right? And she has a rule in her family that you have to take on something challenging, something that stretches you. And then you can quit that when you are successful. So if you took up, I don't know, let's say you took up figure skating and it was very hard for you to become a figure skater. And so you just wanted to quit after one or two times. You're not allowed to quit until you are successful

or at least you have some kind of positive experience. You cannot quit on the downside. You have to quit as a winner. And as a parent, I can tell you that is a great theory. As a parent, I can also tell you that it's very hard to do. That's hard. I mean, I already gave up, so you can say that, but... I think for you parents out there, I mean, I'm sure you'll agree with me that the concept

that you can control your children is a delusion. I mean, it is. You are absolutely not in control. No, but you can hope to be. But I absolutely agree. Okay, so you work in the jury space. How did you get then into the tech world? This is another good story that you should ask what's missing because now you might think, oh, so Guy, you know, he decided to pivot. He made a very intelligent

decision. He started taking programming classes. He started to learn about computing. He started to learn about tech because he was tired of schlepping gold and diamonds. And so he's going to go to tech. And I'll tell you something. What happened is at Stanford, I became very good friends with a person who was very technical. And after graduation, he went to Harvard Business School. And after Harvard Business School, he went to Hewlett Packard in the calculator division. So he was in Eugene, Oregon, or Bend, Oregon, or someplace, and he was recruited out of HP to go to the Macintosh division of Apple.

And then he went to Apple, and then he recruited me out of the jewelry business into Apple. So you could say that, yeah, Guy, you are so smart. You pivoted from the jewelry business. You saw the future of Silicon Valley. You saw that everything was going to go tech. You are such a visionary guy. Even at a young age, you called the future. Or you can say, Guy, you are successful because of nepotism, nothing else.

And that would be closer to the truth. And I will say nepotism is just a hidden market. This is how we get all the coolest opportunities anyway, Guy. So. Well, I'll tell you something, you know, I have come to embrace nepotism because I have come to believe that it is not how you get your job.

It is what you do after you get your job. So yeah, you can be the boss's son or daughter and that's how you can get in. But ultimately it doesn't matter how you got in, whether it's because you're the friend of a classmate or whether you're the son or daughter of the boss or the founder. Ultimately, it depends on how competent you are, how hard you work, and maybe how lucky you are. So I have gotten over guilt of nepotistic starts. And I got to tell you that there's lawnmower parents who just mow down everything in front of their kids.

Then there's helicopter parents who just hover and make every decision. I'm more the lawnmower parent. I mean, I can mow down almost anything in front of my family. Literally I can mow it down. And I tell you something, I have mowed down a few things from my family, but I'm telling you that once the lawnmower goes past, that lawnmower doesn't come back. So if the weeds grow back, that is your problem. I mowed it, I planted your ass.

Now it's your problem. Right. But I'll tell you, I don't call it nepotism. Like I seriously believe that the best type of opportunities we all get from our network and we all get from people knowing people and that's part of the reason to go to college was all respect is that network. Oh, without a doubt.

Right? So, I think people pull you and by the way, it's up to you to make sure that your brand is aligned with where you want to go and that they bring you to the right opportunities. So yes, your brand was somehow aligned with where you wanted to go. He somehow knew about it and he brought you into Apple. That is a really cool story. Again, you know, you have to ask the question what's missing, but without my friend Mike Boych from Apple, the guy that I met at Stanford, I don't know, I might be making cappuccinos

right now in Starbucks and I met him in college. If I had stayed in Hawaii, I would not have met him. If I had not have met him, I would not have gotten to Apple. If I had not have gotten to Apple, I wouldn't become the chief evangelist of Canva and Wikipedia, board of trustees and all these things. And certainly you would not be interviewing a barista from Starbucks on your podcast right now. I mean, not that there's anything wrong with being a barista from Starbucks on your podcast right now. I mean, not that there's anything wrong with being a barista at Starbucks because some of that is an art,

but probably I would be less desirable as a guest. Probably, although the surfboard makes it pretty desirable at the back, but no, but seriously, I think there's a lot to creating your own luck. But when you got into Apple, first of all, it's funny because I literally live across the street from Steve Jobs basement. But what was your impression working with Steve Jobs? Like, how did that environment shape you? Well, listen, everything you have heard about Steve Jobs is true.

It's true. It's true. It's true. Every story, every movie, every article is true. And so this is another very good example of you should ask what's missing because from the outside looking in, it's very difficult to separate correlation and causation. So if you did a really shallow analysis of Steve Jobs, he would say, well, I need to wear Levi's jeans. I need to wear a New Balance jogging shoes.

I need to wear a black mock turtleneck. I need to drive a Mercedes or a Porsche. I shouldn't register the Mercedes or Porsche because I don't want a license plate. I should drive in the carpool lane by myself. I should park in the handicap slot and I will be the next Steve Jobs. And I hate to tell you, but if you did all that, all you would be is an asshole. You would not be the next Steve Jobs. And then speaking of asshole, you could say, well, you know, Steve wasn't exactly known

for treating his employees with empathy and kindness. And that is the understatement of the year. So if you look at all of that, you say, okay, I'm going to black mock Turner, I got a blue cheese, New Balance shoes, Porsche, Mercedes, I'm not gonna be an asshole. You're still not gonna be Steve Jobs. You're not gonna be Steve Jobs.

So the last person who tried to emulate Steve Jobs is now in prison. If you know what I mean. I do. Mrs. Elizabeth, poor girl. But tell me, working with him, like I'm sure it still creates a lot of learning opportunities.

What did you get? Listen, let me be honest. I would not be where I am without Steve Jobs, right? Because let's just say that there's a saying that the rising tide floats. I will also tell you that the tsunami floats everything too. And I was riding the tsunami. So Steve Jobs, I've never met anybody like him. He really could either invent the future or call the future.

He could predict what people would want or he would make whatever the hell he wanted and convince people that they wanted it too. Either one of those explains Steve Jobs. And I learned from him the importance of design. I learned about how to be an evangelist and get people to believe in stuff as much as you do. But I want to go there with you for a second, Guy, because at that point, you needed to literally go persuade people

about a vision that barely existed, right? It wasn't like selling diamonds that you can just pour it on the napkin go persuade people about a vision that barely existed, right? It wasn't like selling diamonds that you can just pour it on the napkin or whatever, this scale. Like now you're trying to like sell this concept and make them create software and hardware for something that doesn't exist. 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. But 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 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. 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. I just put it in the garage. I look at it.

I don't need to pull up at some country club or some disco in my Lamborghini. In fact, I would never do that because I don't go to discos or play golf. But anyway. I'll just say that we just had John Hennessy on our podcast and he wanted to go slam on cars and I'm like, dude, we're going to talk about your careers because I don't know anything about cars, but maybe I'll connect you to. Okay. You should have him and me on and I will debate.

Let's do it. So anyway, so the next level of Apple, you get a free car. So I go into this job review, right? I think he was CEO of Apple at the time. And he starts by saying, you know, guys, the small developers, they just love you. These are the page makers and these companies you probably never heard of. You know, they love you. The small developers love you.

You've championed them. You helped them embrace Macintosh to bring it out. These innovative products. And I'm thinking, man, should I get a Mercedes? Should I get a Porsche? Should I get a Lamborghini? Should I get a Ferrari? Which kind of car should I get?

And then he says, but the big companies don't like you. Microsoft doesn't like you. Lotus doesn't like you. WordPerfect doesn't like you. And Ashton Tate doesn't like you. And I'm thinking, here we go, no more car. And he says, they don't like you. And I'm an optimist, I'm still thinking, yeah,

this is a strength of mine because Microsoft was copying our user interface so they shouldn't like me. And Ashton Tate was doing a piece of crap software so they too should not like me. So I'm going down this list, those big people should dislike me and it's their fault, not mine. But he says, so since they don't like you, but your job as evangelist is to

have all the companies like you. I'm not promoting you to a director. Okay. So, so I walk out of that meeting and I see my friend Jean-Louis Gasset at the time. He was a vice president, but I was a manager, but we were more or less peers in a sense. So I go to Jean-Louis, I say, Jean-Louis, ho ho, guess what, Jean-Louis.

I did not get Z promotion, Jean-Louis. And I said, you know, and this is why, and Jean-Louis, I think I'm just going to quit. And he says, guy, do not quit. It'll be very useful for your career to leave Apple as a director, as opposed to just a manager. And he said, listen, there's going to be a reorg and I'm going to be your boss and you

have another review in six months and in six months, I'll make you a director. So for once in my life, I listened to somebody and I stayed for six months and then I got to be a director. And then the next day I resigned. What? So now, now if you look at my LinkedIn profile, it says, Director of Apple. Only for one day, but I was Director of Apple.

So that's another piece of wisdom. Don't believe everything you read on LinkedIn. Oh my God, that's another piece of wisdom. Don't believe everything you read on LinkedIn. Oh, my God, that's so funny. Oh, my God. So if you're 35 to 65 and listening to this, I mean, one lesson to that is you quit on your own terms and you quit when it's good for you. And don't quit out of fury or hate.

Calm down and think what's the strategic move? When should I quit? And let me quit on my terms, not on the company's terms. Well, I hope you enjoyed this conversation as much as I did. If you did, please share it with friends. This really helps us continue to bring amazing guests. Also, if you are feeling stuck or simply want more from your own career, watch this 30-minute training.

I know it's gonna help. It's leapacademy.com slash training. That's leapacademy.com slash training. And I will see you in the next episode of the Leap Academy with Ilana Golan Show. Okay, so you quit, you do your own ventures, you come back, et cetera. If we look at, speaking your LinkedIn, like the last 30 years,

or whatever that adds up to be, Guy, it looks like Guy is just like hopping from one advisory to one thing to another thing. It looks like this have all these opportunities floating, there's never challenges in Guy guys world. So can you walk us through what does actually take to leap again and some of these challenges that do come with some of this? More me a culprits because if you think that there was ever a grand design or a plan I hate to disappoint you no no such thing. So I started a software company that did okay. I fell in love with writing. The writing led to speaking, and the writing and speaking became very lucrative.

So I just did that for a while and then started another software company. I returned to Apple. I mean, I did a lot of weird things, but I cannot tell you that there was ever a plan. I have gone from thing to thing that intrigued me. Now, some of that I was lucky because really at no point was like living check to check so I could take chances.

Right. But there was no plan and the lesson that I learned I think which is important to people listening to this is this concept of finding your passion is vastly overrated. The passion test is too hard a test because it seems like you're supposed to find your passion and you instantly fall in love and you're instantly good at it 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 you know, 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, 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, but I... 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 the 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. Now you can do it to others. Yeah. But let's just be honest that when I was in college, it's not like I had this aha moment and the scales were removed from my eyes. And I dedicated myself to helping people find their passion because that just did not occur. I wasn't too concerned about changing the world. I just wanted to change the car. But I think maybe it's like your belief was strong enough to know that eventually it connects to DOS.

Like if you believe that you can continue and not quit, somehow you did. There is no case to be made that you should have the victim mentality. Now, do not get me wrong. Okay. I have been very fortunate. I didn't come from a rich family, but I mean, look at the arc of my life. So I come from this lower middle-class family. This elementary school teacher tells me to go into this college prep school guy gets

to Stanford, his parents sacrifice. So he gets to Stanford. He meets this other guy. Nepotism gets him into Macintosh. Macintosh gets him into these other things. And pretty soon he's a writer and a speaker and chief evangelist of Canva and you know, blah, blah, blah. Now it was not easy, but I cannot tell you that I overcame like, I have interviewed people from my podcast that they literally came across the American border as an illegal immigrant. I have interviewed people in my podcast who spent the first, well, not the first, but they spent 22 years of their life in prison. I've interviewed people on my podcast who have ALS and ALS

typically is lethal after two years and she's had it for 10 years. So Guy has not overcome anything like that. All right. So just, let's just get that out on the table in a rare moment of humility from Guy. But I think you just have to keep trying. I'm not telling you that you deserve something

and the world owes it to you because I think that would be deceptive too, but there is no case to be made to say that just understand you are a victim and feel sorry for yourself. That is not gonna work. Well, it's not gonna get you closer to your goals. So you can decide challenges are inevitable,

but the suffering is a choice. You need to decide, are you gonna suffer through life or are you gonna do something about it? As my son often tells me that, suffering and pain is mediocrity leaving your body. Ooh. Oh. Ouch.

That's a good one. But speaking of suffering, Guy, if I'm okay with taking you there, you did go through a very hard moment a few years ago. Can we take you there? Sure. You can take me anywhere you want. Okay. Well, share a little bit because you had some big news a couple of years ago, and that could have taken you into some pretty victim mentality, but you continue to be a podcaster. You continue doing so.

Oh, you mean losing my hearing. Yeah. For example, like that is a big thing. People have told me that I have a really great attitude about this, but honestly, honestly, one of the beauties of my podcast is that I have been able to see relative challenges that I have faced compared to other people, right? About four years ago, I lost almost all my hearing and I use a cochlear implant. That's why we're having this conversation at all. I have a cochlear implant. So technology has brought back my hearing from being deaf

to just being really lousy. If you're out there and you have normal hearing and stuff, you're probably thinking, oh my God, it must be so hard to be deaf. Don't get me wrong. It's not like I said, yeah, I love being deaf, but I will tell you something that if you said, guy, you can either be deaf or you can have pancreatic cancer, what would you choose?

Oh, deaf. Guy, you can have ALS or you can be deaf. What would you choose? Oh, deaf. Guy, you can go to prison for 22 years or you can be deaf. Oh, I choose deaf. Oh, guy, your parents could be crack addicts and they could steal money from you and they could beat you.

What do you choose? Oh, deaf. Oh, guy, your parents could be crack addicts and they could steal money from you and they could beat you. What do you choose? Oh, deaf. Oh, Guy, you could be homeless and you know, you're in 30 different shelters over the course of your life or you could be deaf. Guy, what would you choose? Deaf, deaf, sign me up. And so, you know, with a combination of technology and I guess I'm just an optimist. I'm just a happy guy.

And listen, I prefer not being deaf, but I'm telling you, nobody ever died from being deaf. And I would much rather be deaf than dumb because for deafness, you can get an implant. If you're dumb, I don't know what you can do, but it's not as easy as getting an implant. Oh my God. But seriously, when you get something like this, how do you not fall into a really big black hole?

Or maybe you do for a little bit, because that's okay too. What worked for me, and again, this is kind of hindsight, but what worked for me is that, in a sense, having this podcast was a blessing because I came into firsthand contact with people who had ALS, with people who had been in prison, who people were homeless and all this kind of stuff. So you know, if you have half a brain and you're on the phone with somebody who has been in federal prison for 22 years, it's hard for you to say, oh man, you should feel sorry for me, I'm deaf. I mean, there's just no freaking way.

If you have half a brain and you can say, well, you know, I'd rather have gone to prison than be deaf. Oh. No, but you also didn't quit the podcast. Normal human beings would have said, okay, screw this, this is not going to work. Listen, I don't want you to think I'm Dan Quayle comparing myself to JFK. But, but when I became deaf,

I said to myself, if Beethoven can compose the Fifth Symphony, surely, Guy, you can interview a few people being deaf. And for a while before my cochlear implant, I was basically depending on half a good ear, but also live transcription. And right now, I'm getting live transcription of most of what you're saying so that it helps me, right? So live transcription helps. So one way of looking at it, you know, one message is that there's always a way. And believe it or not, Elana, I interviewed a woman who was deaf and blind and graduated

Harvard Law School. No, you're kidding. That's incredible. Yeah, I can hear, I can see, I don't think I would even get into Harvard Law School, much're kidding. That's incredible. Yeah, I can hear, I can see. I don't think I would even get into Harvard Law School, much less graduate. And then to just top it off and make me feel about two inches tall, she surfs. I was like, how the hell can a woman who is deaf and blind go to Harvard, pass and surf? This is Harvard. Oh my God. Pass and surf. This is not just possible, Guy.

You are only deaf, so you know. Get your ass in gear, Guy. Oh my God, I love this. So Guy, for professionals who are hearing this and saying, okay, but Guy, I want to go faster. I want to go higher. I want to be on stages like you, I wanna author books like you,

I want to be interviewed to podcasts like you. What are some of the advice that you would give them? I already mentioned the passion thing, like don't go looking for passion, just look for interest, and when you find interest, scratch them, and just hope that over the course of your lifetime, a few of them developed into true passions

or true reasons for your existence. So that's one thing. A second thing I would say is do not underestimate the grit that's necessary. You have to be gritty. You have to be willing to persevere. Nothing will come easy that's valuable. And then you have to make yourself vulnerable. You know, I took up ice hockey at the age of 44, never played ice hockey, never skated before. I took up surfing at 60, having never surfed before. Now those are athletic things, but I gotta tell you, I mean, taking up ice hockey at 44 is 39 years too late,

and taking up hockey at 60 is 55 years too late. But you have to say, those were interests that I scratched 39 years too late and taking up hockey at 60 is 55 years too late. But you have to say, those were interests that I scratched that became passions, if not obsessions. And you have to say that you're going to have to pay the price and you have to open yourself up to vulnerability that you will get hurt if you try something risky, if you have in the words of my hero, Carol Dweck, if you have a growth mindset, the flip side of the growth mindset is you have to embrace vulnerability because you are going to get hurt. You are going to fail. You are

going to be ground down and you just have to come to grips with that. And I think it's very, very poor to say to yourself, you know, I tried this and it was so hard. I didn't succeed immediately. It's not for me. If you go through life only doing things that you're instantly good at, you're not going to do very many things. I hear that.

And I think that goes ties really well to what you said in the beginning. The grass is always looks greener on the other side, but it's not. It's hard on that side too. You don't see it. And I think as an entrepreneur, like I remember some all these gurus like, oh my God, you should look at this direction. I was just like, OK, let me go look there. And I was like, okay, that's it.

I need to listen to myself because this is gonna drive me nuts. You know, the grass that looks greener might be AstroTurf. True. Is there something that you wish somebody would have said to you earlier in your career? If somebody had told me not to quit Apple three times because he would be part of a trillion dollar company,

that would have been useful. That would be nice. On the other hand, maybe this is a rationalization, but if I had stated Apple from 1983 till today, I'd be richer than God, but I would also be even more of an asshole. So, you know, there's some upside there. Well, I do believe in freedom and I think you're living the freedom of choice.

I am. Which is the most incredible freedom possible. So, I mean, you're doing your thing and you're giving a lot of entrepreneurs a lot of hope. You're teaching us how to pitch and how to create with decks and whatever. So, it makes a difference. Can I give the entrepreneurs listening some advice? Yeah, please. All right.

So my advice to entrepreneurs first is you have to understand the business you're in and the business you're in is not creating wealth for yourself. It is not creating jobs for society. It is to create customers. You need to take people who never heard of you, don't know what you do or make, don't understand what you do or make, and you need to create customers out of those people. That's the purpose of a company. And if you create customers, the wealth and everything else will follow,

but if you don't create customers, you might end up in jail. So that's step number one. Step number two is that you have to understand that sales fixes everything. You can talk all about the strategic visionary stuff you want, but the end of the day, cash flow is king. Do not ever forget that because you cannot pay the bills with strategic relationships. It is cash. That's number two.

Number three is if you're the CEO and you have a technical officer or an engineer or VP of engineering, let me give you a rule of thumb. Whatever your VP of engineering or CTO tells you about the delivery date of the product, you always add one year. You always add one year. I don't care if they say that it's going to be ready in two weeks. You add a year. You will never go wrong adding one year to the delivery date of what your engineer tells you. And so that's engineering. Now on the sales side, you can never go wrong by taking his or her worst case projection for sales and divide it by a hundred. So basically I'm telling you when your CTO says we'll be shipping in a month, you heard

13 months, when your VPS sales says we're going to do 5 million in the first year, you divide that by 100 and you get, what is that, 50,000 or whatever. Yeah, right. And if you believe that and then you always believe that sales fixes everything, you'll be just fine as an entrepreneur. Now the way you figure out what to make for this person, this customer, this you're trying to create is you have to work backwards. You have to work backwards from what people need as opposed to what you like to do.

So you may like to do something, but that doesn't mean that it's gonna sell. You have to work backwards from what they want. And the way you figure out what they want, that's called empathy. And the way you do empathy is you have to either go and see them in real life, or even better, you go and be them in real life.

And I'll tell you an exercise that I ripped off from my friend, Martin Lindstrom. He was retained by a pharmaceutical company who wanted to get, quote unquote, closer to the customer. So this is the most powerful metaphor you're going to hear in this episode. You want to get closer to the customer. If you work for a large company, when you hear that, most of the time that parses to, oh, we're going to hire McKinsey for $5 million to do consumer research. Okay? So I'm telling, I'm going to save you $5 million right now. You should at least listen to my

podcast and buy my book for the $5 million I'm going to save you right now. So if you wanted to get closer to the customer, the way to do this is to be the customer. And I'm going to give you a story that you can use as a metaphor in your brain whenever this occurs to you. So my friend Martin Lister was working with this pharmaceutical company. He took them on an offsite and he passed out straws.

I actually did this in Maui two weeks ago. I passed out straws to the executive team of this company and I made them breathe through the straw during my presentation. And at the end of that, I said, listen, this is about empathy. Let me tell you a story about my friend, Martin Lynch, from the pharmaceutical company. He passed out straws like I just did. He made them breathe through straws just like you did. And the reason is, he said, because your customers have asthma. And that's what it feels like to have asthma.

Like you're breathing through a straw every minute of your life. So you want to get closer to your customer. I just made you into the customer. So now, if you're listening to this podcast, you take that metaphor and like, how can you be the customer? How can you be the customer. So now, if you're listening to this podcast, you take that metaphor and like, how can you be the customer? How can you be the customer? You breathe through a straw. If you are designing minivans, you actually use a minivan and you try to figure out, well, how do I get two baby seats, two strollers and two baby bags in the back of this thing? And if you are a camera company, like, you know, have you ever tried to go

through the menu structure of a Japanese digital camera? I mean, it's like they sat down and they said, oh, how can we confuse these Americans the most? Let's just put the things you need the most buried in the 14th menu of the 14th menu. And maybe an example every day we encounter is like, well, we're going to give away all this free information. All we ask is people set up an account, but to set up an account, we first want to get their credit card, even though we're not going to build it for the first month. So yeah, we're going to ask everybody to give you

their credit card for a free account. Like, in what planet do you live on? And then they say, yeah, and then we got to make sure it's not some kind of Russian bot. So we're going to make people feel, you know, complete a cap test. The motorcycle thing. Yeah, yeah. So, yeah. So there's a three by essentially four by four matrix. And, you know, click on the pictures that have motorcycles.

And I have literally a lot of never, ever succeeded in doing that the first time. I know, I always fail somehow. I mean, it should be pretty obvious that, oh, you know, click on the pictures with a school boss. I mean, a school boss is not a subtle thing, but I cannot get that right. You should be the customer. So, you know, the underlying principle here, if you're an entrepreneur is, assuming you're not a psychopath, you should never ask people to do something you would not do yourself.

And you wouldn't give a credit card. You don't like filling out CAPTCHA. You know, you don't like putting up with all that bullshit. So why are you making your customer do that? That is true, Guy. I admit that is true. Can I go surfing now? Now you can go surfing. Guy, thank you so much for everything.

And continue to inspire and crush it. Alrighty. I hope you enjoyed this as much as I did. If you did, please share it with friends. Now also if you're feeling stuck or simply want more from your own career, watch this 30-minute free training at leapacademy.com slash training. That's leapacademy.com slash training. See you in the next episode of the Leap Academy with Ilana Golanshchuk.