GUY KAWASAKI: 20 years ago, I had a Porsche 911 and I’m driving in Menlo Park, California in my Porsche. 

JEFF BERMAN: That’s Guy Kawasaki, author, podcast host, veteran of the early days at Apple, and currently, Chief Evangelist for Canva. 

KAWASAKI: So I pull up to this stop sign, and I look to my left, and there’s a car with four teenagers in it. And they’re smiling, they’re laughing, they’re making eye contact with me, and the girl in the front seat makes this motion, roll down your window. 

I press the button, the window goes down, and she sticks out her head. And like in my mind, I’m saying to myself, Guy, you have truly arrived. Even teenage girls know who you are. It’s because of your work at Apple, it’s your startup garage. com, it’s your writing, it’s your speaking, it’s your TEDx, you know. Everybody knows who you are. These are the thoughts going through my head as I’m sitting in my 911. So she sticks her head out, and she says to me, “Are you Jackie Chan!?”

BERMAN: Ooof. On so many levels. But Guy says he used that day to distill a deep learning.

KAWASAKI: Don’t worry about what motivates you. Just worry about that you got motivated and you made a difference. The lesson that I took away is that now one of my motivations in life is that someday Jackie Chan is in Hong Kong in his Bentley, his S Class, or his Panamera, and he pulls up to a stop sign. There’s four teenagers in this car next to him, and they roll down the window and they say to Jackie Chan, “Are you Guy Kawasaki?”

That’s one of my goals in life.

BERMAN: We would all be so lucky to be mistaken for Guy Kawasaki and to dream as big as he does. I don’t just mean movie-star status. 

Guy joined Apple in 1983 and helped launch the Macintosh line of Apple computers starting in 1984. His title was Software Evangelist, selling and advocating the new product line. Since the 1980s, he’s held the position of evangelist, advisor, and brand ambassador at several high-profile companies – including Mercedes-Benz, Motorola, and now the design firm Canva. He’s also been a founder and investor in tech beyond personal computers through his firm, Garage Technology Ventures. 

Now in the fifth decade of his career, Guy also shares his experience – far beyond his business partners. He’s written 16 books – on entrepreneurship, leadership, and personal growth. 

Guy hosts a podcast called Remarkable People, with accomplished figures from all walks of life. He says the one thing they have in common is an insatiable desire to learn and to do more. 

It’s this combination of an impressive corporate resume and personal growth that I wanted to explore with Guy Kawasaki. He has keen insight into how founders and entrepreneurs can grow their companies – by expanding their thinking about what’s possible in their own lives. 

[THEME MUSIC]

[AD BREAK]

BERMAN: I’m Jeff Berman, your host.

One of my favorite aspects of Masters of Scale is hearing the stories behind groundbreaking innovations. And it’s not just the person with the original idea who takes it to scale. It’s the people who first work alongside any boundary-pushing founder need to have vision, perseverance,  and a growth mindset. 

That’s the perspective we focus on today. Guy Kawasaki had an up-close view of the early scaling journey at Apple – the first days of the computers we now simply call “Macs.” But he didn’t set out to work in a brand new industry or for a maverick company.

Guy Kawasaki grew up in Hawaii before moving to California for college at Stanford University. His early understanding of relationships would have a huge impact on his life and career. 

KAWASAKI: Growing up in Hawaii, you learned about family. You know, the Hawaiian word for family is ohana.

But ohana extends beyond your blood relatives. You know, there’s this sort of honorary title that you give to people who are like family, but not blood related. I think that the sort of horizons in Hawaii, if you were successful, you ran Sears Roebuck at the Ala Moana Shopping Center. You ran Hilton Hawaiian Village. You worked for Dole Pineapple; that was the sort of spectrum of opportunities there, if you were very successful.

And then I get off this airplane and I land in California, and it was as if the scales were removed from my eyes because there’s Hewlett-Packard, there’s National Semiconductor, and there’s Intel. And these people are creating international companies, not just one great department store or one great hotel.

And so it just totally broadened my horizons. 

What Guy Kawasaki learned from the jewelry business 

BERMAN: After graduating from Stanford, Guy tried law school. He got in, and he started, but dropped out after just two weeks. 

KAWASAKI: Law school was basically saying, ”Yeah, you may be bright, but we’re going to tear down your mind and build it back up again,” and I could not handle that pressure. Quite frankly, I wimped out. Maybe that’s the last time I wimped out. Of course, you could make the case that, Guy, you wimped out and you ended up working for Steve Jobs, which is quite the contrast.   

BERMAN: But before Apple, Guy earned an MBA from UCLA. 

KAWASAKI: While I was at UCLA, I worked for, of all things, a small family-owned jewelry manufacturer.

So I literally schlepped gold and diamonds, and we sold them to retailers. And from there, I sort of jumped the curve from jewelry to software in the Macintosh division. And the only explanation I can give you for that is nepotism. My Stanford classmate and buddy hired me. And on paper, you know, you wouldn’t need AI to reject me as a candidate to be a software evangelist for the Macintosh division.

BERMAN: Well, I’m going to push back on you that it was nepotism, because one, that was Ohana you made, not Ohana you were born into. And two, the lesson that I’ve heard you talk about, having learned from schlepping jewelry all over the world, is that sales is everything. And you have to know how to take care of your customers. And I have to imagine at Apple in those early days, having someone in your role who was relentlessly focused on the needs of the customers was a critical component. And so, actually, you seem like the ideal hire for it, given the experience that you’d had.

KAWASAKI: Far be it from me to correct the record, but let me more accurately describe this. So, people think of sales today as, “Should I make the border blue or should I make it yellow? And let’s do A–B testing and see if we get more than 1 percent click through rate increase.”

This jewelry business is hand-to-hand combat. You called on jewelry store owners, and you begged them for business. They kept you waiting in the lobby. Sometimes the end of the day came and they said, sorry, I don’t have time to see you anymore. And they stick your designs on a scale, and they want to pay you slightly over what the scrap value of your ring is.

And all that really taught me how to sell, and that skill has stayed with me the rest of my life. Believe it or not, working in the jewelry business prepared me to be a tech evangelist. 

BERMAN: In jewelry, Guy had to convince his buyers that something about the product made it worth more than just its literal weight in gold. Maybe the design or the craftsmanship. 

What is a software evangelist?

At Apple, the pitch was more complicated. What exactly did his job title mean – “software evangelist?” In the 1980s it meant convincing software developers to make programs for Macintosh computers.  Guy was the hype person – he had an enthusiasm and grit rooted in his sales expertise, and the knowledge and passion to push for widespread acceptance of Apple’s new technology. It was sales, marketing, and leadership all rolled into one.

And so, with Guy as Software Evangelist, Apple’s Macintosh computer set off the desktop publishing revolution, empowering customers to produce documents with text and images. Guy also fostered relationships with developers who designed software and programs for Apple computers. He convinced them that it would be worth the effort. When Guy left Apple in 1987, the company was just starting its meteoric rise.

BERMAN: When you reflect back on those early days at Apple, was there a sense of how big Apple could be back then?

KAWASAKI: So you are talking to a person who quit Apple twice and turned down Steve for a third position. So you know, the receipts indicate that I obviously did not think that Apple was going to be the most valuable company in the world because I left there twice and turned down the chance to come back.

BERMAN: Guy is referring to the time he came back to Apple for a couple of years in the 1990s, then left again for his own projects – and declined later opportunities to return to Apple.

How companies can inspire their intrapreneurs

He left to pursue other opportunities that simply couldn’t happen within Apple. And maybe there’s no scenario where Apple – or any other big company – could have contained his multitudes. But there are ways for leaders to encourage and keep innovative team members within their ranks – the intrapreneurs, those who are bursting with ideas they dream of pursuing 

BERMAN: What can big companies learn from your experience about how to not just keep talent like you but inspire talent like you, especially when your role is as evangelist, You’re the one who’s out pitching the vision for the company.

KAWASAKI: Well, I’ve thought about this a lot, and I’ll give you some factors that I believe would help intrapreneurs. So first of all, you will need an egomaniac leader because this egomaniac leader has to withstand a lot of pressure from the existing infrastructure of the company and the negativity that this leader is going to face is that the sales force is going to say we’re not interested in this product.

Just give us better faster cheaper status quo; if you don’t make the company jump to the next curve, the company will die. 

And Kodak is a particularly good example because, in 1975, Steve Sasson, an engineer at Kodak, invented the digital camera. Now, If you invent this digital camera and you go to your boss and you say, “Guess what, boss, I figured out a way people don’t have to buy film anymore. Am I not a remarkable engineer?”

You would have probably been fired because they were geared towards making film. And so the lesson is, do you want to be the next Kodak? Or do you want to be like Apple, that went from personal computers to handheld devices to app stores to, continuously reinventing itself?

BERMAN: It sounds counter-intuitive: redirecting resources, time, and energy from the current product line for an experimental, future, unknown innovation. But, as Guy says, the bold thinking of these intrapreneurs is what allows companies to survive in a competitive marketplace and have a chance to dominate it. 

KAWASAKI: A second thing you need is a separate physical building. I don’t think you can do intrepreneurship inside, physically a company that is already existing. So if you are sharing resources physically inside a building, you’re never going to be top priority. You want people who are going to live and die with your idea, not people who are matrix managed and giving, a slight part of their perspective and a slight part of their bandwidth to one thing, and they’re doing mostly the existing thing.

I think that a separate building should be at least a mile away from headquarters. You want something that’s close enough where you can come back and steal resources, but far enough so that when managers at the company want to come see you, they have to get in a car. And it’s like such a psychological barrier. Oh God, I got to get in my car. I gotta drive. I gotta find parking. I’ll just leave them alone. 

BERMAN: Guy, part of what’s inherent in what you’re saying is also something I’ve experienced a number of times in my career. I’ve been asked to present a five-year business plan. Right. And you’re laughing because it’s a joke, but, you think about where we were five years ago, right? I mean, as we sit here today, we hadn’t had COVID; generative AI was not something that, you know, more than a few thousand people were really thinking about seriously.

What’s the point of a five year plan?

I mean, the world was a very different place, and five years from now, it’s going to be even more different. So given that we know that this is true, why do so many investors, why do so many big companies, and why do they think in this very narrow, constrained way where you’re trying to forecast something that is literally unimaginable?

KAWASAKI: Who among us five years ago said there was going to be a day when there’s large language models that are sentient and smarter than most people and they can write your essays, create your PowerPoints, and generate images. Nobody said that. 

It’s part of a game that you have to play that you have to pretend like you know what’s going to happen in five years because if you took the opposite approach and somebody asked you for a forecast and you said, “Listen, I have no freaking idea. I don’t know what’s going to happen. I’m just making it up as it goes.” Which is the truth. I would not say that is an optimal answer for receiving investment. And I think that the sophisticated entrepreneur realizes it is part of the game. 

It has to do with the fact that many venture capitalists have to report to limited partners, and limited partners are fund managers, and fund managers are spreadsheet jocks, and that’s part of the game they play. But truly sophisticated investors and sophisticated entrepreneurs know that it is a game. And so it’s kind of a litmus test on how they feel about your business, as opposed to you know really what they’re trying to do is due diligence.

BERMAN: Well, it’s interesting. I hadn’t thought about it this way before, but the way you’re describing it, it sounds like it is a filter for deciding what work to do that is similar to Warren Buffett’s investment thesis, If you love the product, if you use the product, if you’re obsessed with the product, then that sounds like a pretty good place to be.

KAWASAKI: Well, it’s easy to evangelize great stuff, and it’s hard to evangelize crap.

A demo counts for 1,000 slides

BERMAN: Guy has been evangelizing for his current company, Canva, long before most of us heard about it. He started there in 2014, when awareness of the product was critical. And the role of evangelist was clear. 

Guy saw similarities between Canva and the early days at Apple. Canva was trying to democratize design the way Apple did for computing.

KAWASAKI: So, ten years ago, it was me and a handful of people looking like fools when everybody was using Photoshop and Illustrator and people were saying, if you truly want to be a designer, you have to learn Photoshop; you have to be an Adobe customer.

And the same thing with Macintosh, when everybody was using MS DOS. And I guess what I learned is, at least in my life, that a demo is worth a thousand slides. So you can have all the slides you want and talk about your differentiation and your key selling points, and everybody makes a chart and you know, there’s these features in your competition, and your competition’s column is all empty, but your column is all check, check, check, check, check.

Everybody does that. It’s all BS. So I think the rubber hits the road when you back then in 1983. You pull your Macintosh out of a bag, and you show them Mac Paint and Mac Write. Now these are people who are used to electric correctable typewriters, or at best, at best daisy wheel printers.

And you show them Mac Paint and Mac Write and bada bing bada bang. They either get it in 10 seconds or they never get it. I think the same is true with Canva — that with Canva, I can build that Instagram graphic faster than most people can boot Photoshop. And you immediately get it. So I’m telling you, if there’s a skill that is necessary for entrepreneurs to succeed, it is that you have to do a great demo. A demo counts for 1000 slides.

BERMAN: It’s a well-worn adage of sales and marketing that, when you’re selling something great, it is far better for a prospective customer to experience the product rather than merely hear a pitch. Do you remember the first time you used a product or service that was simple, was useful, perhaps even a beautiful experience? That was Canva for Guy. When he first saw the product, he knew the impact it could have. For Guy, evangelizing Canva meant and means showing people its customer-friendly interface for graphic design. The company has attracted 170 million monthly users, and earns $2 billion in annual revenue. At first, it drew mostly individuals and small enterprises — customers who needed visual assets for marketing, without hiring a designer. Now, clients include FedEx, Zoom, and Starbucks.

By deeply understanding and believing in the advantages of his products, Guy has helped Apple, Canva, and others scale to incredible heights. After the break, we’ll explore more of his personal experiences and insights, especially around AI. Spoiler alert – when it comes to AI, Guy is yet again an evangelist.

[AD BREAK]

BERMAN: We’re back with author, entrepreneur, podcast host, and tech evangelist: Guy Kawasaki. To watch our complete interview with Guy, head over to the Masters of Scale YouTube Channel. 

Guy has worked alongside entrepreneurs who grew their ideas into some of the most valuable businesses of the last half century. He’s also struck out on his own, starting a venture fund and his own companies. He has learned countless lessons in leadership, marketing, sales, and attracting investors. 

And his most recent endeavor ranges widely outside the realm of business. Guy’s podcast “Remarkable People” features just what you’d expect, from the title – life stories and lessons from authors, scientists, politicians, and more. 

BERMAN: With so many hours of incredible insights on the show, Guy decided to turn the podcast premise into a book.

BERMAN: Guy, we sit here talking in March of 2024. Your book, Remarkable People is just out. You’ve talked a little bit about how you’ve used AI in the process of writing. Can you give a specific example of where AI made a real difference for you in writing the book?

KAWASAKI: Absolutely. I use AI as a research assistant. I don’t just go to chat GPT and say, give me 50,000 words on how to think remarkable and be a remarkable person. I use it as a research assistant to help me write the book. 

Writing a non-fiction book today with ChatGPT is so much easier than before. Because before you had to depend on reading extensively and knowing a lot of people who could give you ideas. 

Be like Jane Goodall and Julia Child

BERMAN: That approach meant using AI tools to help identify examples and patterns, adding layers of insight to Guy’s innate curiosity. When someone’s story struck him, he boiled it down to some specific elements he found intriguing, and asked AI to help him find more.

KAWASAKI: And I noticed this book comes from interviewing 250 remarkable people like Jane Goodall, Stacey Abrams, Wozniak and what I noticed is that every remarkable person had a growth mindset. To be remarkable, you, you have to have a growth mindset.

Now, there are two kinds of paths for many of these remarkable people. Some people, like Jane Goodall, they fall in love with animals at age six and for the next 84 years. They’re focused on animals. Then there’s people like Julia Child. Julia Child, until her mid thirties, was a spook working for the OSS.

The OSS is the organization that became the CIA. And in her mid thirties, she moved to France and fell in love with French food. And that’s why Julia Child is a French chef. There’s these two theories, and part of being remarkable is you have to be able to hold two conflicting ideas in your head.

One is, be like Jane Goodall, stick to the path and grow on that path. Another is, change horses in the stream. And so I love the theory of people making great changes. So, I need examples.

So I go to ChatGPT, and I said, give me five or six examples of people who have made radical shifts in their career and achieved great success. Thanks. 30 seconds later, chat GPT says Jeff Bezos. Jeff Bezos started as a private equity person, and he moved to, selling books and e-commerce. And the second example it provides is Julia Child.

And I say, Julia Child, how is Julia Child an example of switching careers? And that’s how I learned that she worked for the OSS. Now ChatGPT makes crap up. So then my co-author, I just read this about Julia Child; go verify that it’s true that she worked for the OSS. And I can tell you with total certainty that Julia Child would not be an example in my book were it not for ChatGPT. And I would make the case that, at least at the state of the art of generative AI today, you still have to make sure that the message is right. So it is the world’s greatest assistant, but it is not a replacement for you.

BERMAN: I hear that. And, as I use AI, as the team behind Masters of Scale uses it, we’re getting more efficient. It’s helping us work more quickly, whether that’s Grammarly or Descript. It’s incredible how much more productivity we get. But that human element is still there, and it feels like a lot of AI is becoming right now and is likely to be at least for the next few years, which is it’s not a replacement for the human element. It’s really a co-pilot. It’s something that’s augmenting your analysis and informing your decision making But it’s like AI informed, not AI determined.

KAWASAKI: And I would say that’s a very good use of AI for writers and it’s a very good use for investors to make decisions. At the very least, you could stick in a business plan and ask chat GPT, are there any other similar ideas that are floating around the world? I don’t know about you, but I’ve met many entrepreneurs, and they always say that no one else is doing what we’re doing.

And no one else is capable of doing what we’re doing. And I’ll tell you that my initial reaction to anyone who says that is, do you not know how to use Google? I mean, how stupid are you? 

At the end of the day, you know, there’s only going to be one, two, or three winners. So, what’s your unfair advantage? And I think that is the most difficult question an entrepreneur will face. And when I, you know, looked at plans and pitches, I kind of made the assumption that yes, they can deliver on the technology.

Yes, they can do this. And now let’s assume they can do this. How do they differentiate from everybody else? And I’ll tell you some, the irony of this is that that’s going to occur in LLMs. Like today, if I had to explain to someone when to use chat GPT, when to use Bard, when to use Perplexity, when to use Claude, and when to use all this, I couldn’t. I mean, I use all fives kind of at random.

And in the car business, as you say, if somebody says, well, I want the car that’s the safest. Okay, Volvo, I want the car that’s the sexiest. Okay, Ferrari, you know, I want the car that gets the furthest on a charge. Okay, I understand that. But I don’t know how LLMs are going to create unique positioning in people’s minds.

BERMAN: We don’t yet know how AI tools are going to distinguish themselves from each other. We also don’t yet know how and whether customers will care which large language models power those AI tools. But If anyone knows how to make a product stand out in a new or underdeveloped market, it’s Guy Kawasaki.

And he sees AI as something every company should embrace, to speed its innovation.

KAWASAKI: I’m a glass half full kind of guy. And I would say that if I were running these companies, I would say, oh my God, this is the best thing ever for us to innovate. And we’re going to embrace AI before our competition does.

And we’re going to embrace AI before two guys in a garage do. And we’re going to take those two guys and two gals in a garage who are innovative. And if we can’t innovate them, we’re going to buy them. And even if they’re close to us, then we have to use our other strengths, such as brand awareness and scalability.

Huh, what a concept. There should be a podcast about that. So we can scale. You know, Apple has significant advantages over any two guys or two gals in a garage. So I think that you just have to figure out that this is going to happen and think that it’s the most exciting time to me.

AI is a bigger deal than personal computers. chips, social media, internet, all combined. I cannot believe how much has happened in one year.

BERMAN: Bigger than the Industrial Revolution?

KAWASAKI: Bigger than the industrial revolution. I seriously think so. I feel so lucky to have been born and, you know, been living when this happened.

This is humongous.

BERMAN: It’s great talking to you, I appreciate you.

KAWASAKI: Thank you.

BERMAN: Of all the lessons Guy Kawasaki shares, I’m perhaps most struck by the simple question that every entrepreneur should ask: “How does my product improve on what came before?” When you answer that question with conviction, your team members, investors, and customers are far more likely to join you on your journey. Passionate advocates who have seen and believe in new products can authentically spread the message of their value. That’s evangelism. Done well, it works no matter what you are selling. 

I’m Jeff Berman. Thank you for listening.