GaryVee x Guy Kawasaki: Lessons on Business, Tech and Culture

6 Sep 2025 · 27 min

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The GaryVee Audio Experience: Episode Summary

Podcast Title: The GaryVee Audio Experience Episode Title: GaryVee x Guy Kawasaki: Lessons on Business, Tech and Culture Release Year: 2024

Overview

In this episode, Gary Vaynerchuk (GaryVee) interviews Guy Kawasaki, a legendary author, entrepreneur, and former Apple evangelist. The conversation centers around Kawasaki's new book and his extensive experience in shaping business and culture. Key themes include lessons from Silicon Valley, the evolution of marketing, and how entrepreneurs can adapt to the fast-paced and ever-changing business landscape.

Key Discussion Points

Introductory Remarks

  • Gary shares his reluctance to break his New Year's resolution of avoiding virtual podcasts but makes an exception for Guy Kawasaki due to admiration for his work.

Guy Kawasaki's Background

  • Career Start: Began in jewelry manufacturing before moving to Apple as a software evangelist for the Mac division.
  • Current Role: Chief evangelist for Canva and host of the "Remarkable People" podcast.
  • Publication History: "Think Remarkable" is his 16th book, showcasing a long history of authorship.

Reflections on Communication and Writing

  • Gary expresses his struggles with writing and admiration for Kawasaki's prolific blogging era in the early 2000s.
  • Kawasaki discusses how his high school experiences shaped his love for writing and emphasizes the value of tough mentorship.

The Concept of "Think Remarkable"

  • The book distills insights from over 220 interviews with remarkable individuals into a structured guide for personal and professional development.
  • Core Themes:
  • Growth: Continuous learning and progress.
  • Grit: The importance of perseverance over mere talent.
  • Grace: Being kind and empathetic in the pursuit of business success.

The Shift in Generational Mindset

  • Both speakers note the challenges faced by today's youth in an era of instant gratification and numerous options.
  • Gary emphasizes accountability, suggesting that young people should take responsibility for their own success rather than blaming external factors.

Legacy and Making an Impact

  • Guy expresses a desire to be remembered for making a difference in people's lives rather than for financial success alone.
  • The importance of contributing positively to society, especially for the younger generations, is highlighted.

Closing Thoughts

  • The episode concludes with Gary and Guy discussing the broader implications of their experiences and the lessons imparted through Kawasaki's new book.
  • Book Release: "Think Remarkable" is set to be released on March 6th, 2024, designed to be a concise and impactful guide for readers.

Key Takeaways

  • Grit Over Talent: Success is often rooted in perseverance rather than innate ability.
  • Role of Adversity: Challenges and tough mentorship can lead to significant personal growth.
  • Empathy in Business: Kindness and grace can coexist with a drive for success.
  • Importance of Accountability: The younger generation must embrace responsibility in their journeys.
  • Making a Difference: True fulfillment comes from contributing to the lives of others rather than mere financial achievement.

Conclusion This episode provides rich insights from two industry veterans, emphasizing the evolution of business, the importance of character in entrepreneurship, and a thoughtful approach to success that prioritizes personal growth and societal impact. Gary and Guy's engaging dialogue serves as a reminder of the values that underpin meaningful achievements in life and business.

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Transcript

Automatic transcript. May contain errors.

0:00This is the Gary Vee Audio Experience. Vayner Nation, how are you? Welcome to the podcast. There are very few people on earth that I'm willing to break New Year's resolutions. My New Year's resolution, one of the silly ones was to not do virtual. Excuse me. By the way, Russian superstition, if you sneeze, it means what you're saying is true. So this is really, really working here for me. My New Year's resolution was not to do any virtual podcast this year. Guy reached out. He's got a new book. He's one of the great authors in business and culture and tech. I said, Guy, awesome. Please come through.

0:37I'm really trying to hold the line. He goes, Gary, in reverse, I'm not traveling, which I remembered we've talked about in the past. I said, I just can't say no to this guy. I like him too much. I admire him too much. So here we are, Vayner Nation. Guy, how are you, my friend? I'm good. Thank you very much for breaking your rule. I understand it's a slippery slope and, you know, I won't tell Adam Grant or I won't tell any of these guys that you broke the rule for me. Okay. I appreciate. Guy, why don't you tell everyone here for the small part of my audience that doesn't know you or your legendary career, maybe one minute on that.

1:11But then more importantly, we're here to talk about a new book and let's talk about what it is and what it's about. Okay. I started my career in Silicon Valley at Apple, basically. So after a short career, actually not so short, a career in the jewelry manufacturing business where I schlepped gold and diamonds, I went and became software evangelist for the Mac division, convincing people to write Mac software and create Mac hardware. So I worked at Apple in the Mac division. I left. I came back as Apple's chief evangelist. I left. I started some tech companies. And today I am chief evangelist of Canva, which is something that Gary and I know and love.

1:53And I'm going to make a lot of money on. Here come the New York Jets, baby. And also I have the host of a podcast called Remarkable People. So that's what I do right now. How many books have you written? This is the 16th book. And Gary, I got to tell you something. 15 times I said, I don't have another book in me. This is it. Somehow it keeps coming. If you had told me, if you had told me 30 years ago, you're going to write 16 books, I would have told you you're nuts. Speaking of writing, one of the ways that I really became a fan of your work and you as a person, there was one era of the modern web that I was not a part of.

2:37Obviously, I launched winelibrary.com in 1997. So it was very early e-com, email marketing, Google AdWords. And obviously, since 2005, every social media or attention trend I was part of. But even though I've written six or seven books in my career, the one skill of communication that I struggle with is writing. I have two new books coming out, a kid's book and a business book. And all of them or audio, you know, when I do my books, I audio. The era that I missed was this beautiful era in 2003, four, five, six, seven of blogging. You were very prolific in that for just two seconds. Like when you think back to that era, pre-social media, but there was like, you know, WordPress and blogging.

3:19Was that an enjoyable era for you? It's an enjoyable era for me because I love to write. And in high school, I had an English teacher and he was a real hard ass. He's the most hard ass teacher I've ever had. And he instilled in me a love of writing. Well, I use the word instilled loosely. He pounded it into my head. And you know, one thing I learned, Gary, and I also learned this from my podcast about remarkable people is that when you look back, the coaches and the teachers and the bosses who are the hardest on you taught you the most. And And, you know, there's a lot of young people listening to this and you might be tempted to go find that easy professor, easy boss, you know, easy everything.

4:02And I'm not saying you're going to regret it. But 20 years from now, if you're working for a real hard ass like Steve Jobs, you're going to say, God, that was the best experience. Yeah, it makes so much sense. I think, you know, I often say adversity is the foundation of success. And, you know, this like maybe it's because we're graying up and every generation does this. I believe it's because these kids are so fortunate to have so many options as they do today that we didn't have. But, you know, people are no question struggling with accountability and struggling to be comfort in adversity or being patient.

4:43and I think you and I are lucky that we grew up in eras where in some ways we didn't have the option. Even the Steve Jobs and others, it did take years. We didn't have this instant wealth, instant fame ecosystem. Literally a kid today will post something mundane and silly on TikTok and overnight within 24 hours amass 100 ,000 followers and start on a journey of being known, get a hoodie company, DMing them and give them$5 ,000 to wear it. And that level of speed and it's kind of like people that the data around people that win lottery tickets, they lose all their money. There's less sustained obsession with building something sustainable.

5:26It's very instant. You know, ironically, probably the thing that got me into most of the Silicon Valley's ecosystem. Today is the 18th anniversary of my first episode of Wine Library TV. Yeah. Wow. And I did that show every day for five years, every day. Yeah. And it was two years before it started to show up on Dig or Daring Fireball or all that. This goes back to the blog era, like showing up on TechCrunch or Metafilter or all the things that used to create Rocketboom or the things that used to create Discovery. Anyway, nonetheless, I'm reminiscing because I enjoyed my time with you. Talk to me about Think Remarkable.

6:07Yeah. So Think Remarkable. Basically, with the Remarkable People podcast, I've had about 200, 250 interviews with remarkable people like Gary Vee and Jane Goodall and Neil deGrasse Tyson, Steve Wozniak, Stacey Abrams. I bet you never thought you'd hear your name in the same sentence with Jane Goodall. There you go, Gary. I finally made it. I finally made it, my brother. And what I figured out looking back over the 220 or so episodes is, you know, I have 220 hours of great inspiration and information. It's 5 ,000 pages of transcripts, but nobody's going to listen that long or read that much. That's right.

6:54So my co-author and I, Madison Neismar, we distilled all of that down to 170 pages. And the filter was my 40 years of experience. So this is not an interview book where it's just the transcripts, chapter by chapter, organized by person. This book is organized by stages of life as you become remarkable. And the three stages are growth, grit, and grace. And like a few minutes ago, you were talking about instant success. I think instant success from the outside looking in may be true. But, you know, yeah, there are outliers and unicorns farting pixie dust. But in the real world, it's grit. I would take somebody with grit over talent anytime.

7:47100%. I mean, look, you know, I was such a poor student and we grew up in an era where like grades were complete definition of if you were smart or not. Yeah. And, you know, for me in the late 90s into the early 2000s, as I started building my dad's business and as I got into my era, like, and especially when I got into angel investing around the time where we met early on, I invested in many companies started by kids from Harvard and Stanford. And I would be baffled, Guy, because I grew up in a framework where, by default, I thought these kids were smarter than me. And to your point, I learned pretty quickly in the mid-2000s, I'm like, wait a minute, this entrepreneurial thing.

8:26And then it became bigger. And I love that you used grace. I think one of the things that I'm proud of is, you know, this is interesting because obviously you grew up with the legendary Steve Jobs. but something that I always had a disconnect with Steve, even though I admired so much of what he accomplished was I grew up in a family business where my father was tough on the employees and I was completely the other way. And to your point, I wasn't easy on the employees. First of all, I set an example. I worked 18 hours a day. So you can imagine like even going out to lunch, I would make a comment of like, what are you doing a half day?

9:00Like it wasn't that easy, but I was incredibly gracious and kind. and I love you for putting grace in a business. Like I really do think nice guys finish first and I do want to teach the world that you don't have to compromise who you are as a human to have financial and business success. And I love that you have grit and grace in there. Growth is of course very understandable, but I feel like people, I'm obviously, and you know me pretty well, I'm an aggressive communicator. I'm a - okay i learned a new phrase today aggressive communicator like i know i know that i was inspired by randy the macho man savage and chris rock and richard prior i can see in the way i communicate being affected by things i consumed as a kid but i like that kindness and empathy and compassion and grace are making it into the lexicon of success yeah like you know gary as i look back, I'm 69 years old.

10:04So I figured out in the first third of my life, I was underpaid. In the second third, I was overpaid. And now it's time to pay back. And I think, you know, when I die, I want people to say that I helped them make a difference. And I don't mean you have to be Jane Goodall or Steve Jobs. Making a difference can be to just one person, you know, one kid you mentor, one classroom, one team, one stream, one river, you know, one street. And the way that it works, and I hope people understand this, that this is not a typical self-help book where, you know, in 48 hours I can teach you how to be remarkable.

10:48That's a bullshit lie. The way it works is if you make a difference, if you make the world a better place, people will start considering you remarkable. So the way it works is you do good shit, you will be considered remarkable. It's not because you woke up one day and hired a PR firm to position you as a remarkable person. I couldn't agree more, brother. And look, you know this, you're a bright man. We got fortunate. You and I have some similarities, which is we have our ambitions and we have our, like any human, we have our selfish wants. But the reason we both consistently communicated for decades now is there's something within us that likes us to share.

11:28You don't share as consistent as you have when it's just what's in it for you because you scratch that itch. When you have something that's selfish or that's in it for you, it eventually becomes abundant and it becomes boring. For someone like you who's been communicating for over 20 years now publicly consistently back to blogging early twitter we were there you know all the books written i mean to put it in gary v terminology it takes a lot of energy to be an asshole it's much better to be a nice guy it's a lot easier to be a nice guy than an asshole and if you're an asshole you are clearly hurting inside yeah That's the part that kids learn when they get into their 20s, 30s, 40s, 50s.

12:20It takes everybody some, everyone's on a different track. But what you realize is, I realize all the people that are mean or angry or trolling or when I encounter them in real life, short or abrupt or inappropriate, it's 100 % a reflection of what's going on in their own souls. And for me, I don't know how to be upset for myself when I'm met with darkness. I'm only built, parented, and luck of the DNA I default into compassion for them Yeah, I mean, I think You know, it may be, Gary, that You're third generation or second generation in America? You're first? I was born in the Soviet Union, guy You were born in the Soviet Union?

13:06I was, brother So now, obviously, I came, I was very young I was four, five, but I grew up I mean, I lived in a studio apartment with seven, eight family members in Queens, New York for years when we first came. Like I went on one family vacation. We stayed in a Holiday Inn in my entire childhood. Like I really lived it. So my gratitude is off the charts. Yeah. Yeah. So, you know, you have kids now, right? And I'm third generation and I worry about this. So you must really worry about this. Because it seems to me like every succeeding generation, they're getting it easier and easier. And I'm not saying I suffered.

13:50And, you know, I had a I came from a lower middle income family. So I wasn't right. But I wasn't rich. So I don't want to, you know, but I worry. Yeah. Well, I'll tell you why. And I'm sorry to jump in. I apologize for jumping in. But let me say this because I want to give you some flowers. Regardless of where someone starts their journey, what you represent, I mean, there's people who are third generation, upper middle class, but they were the fourth generation or the fourth generation. They were the individual that took the family to the moon, right? There's some people doing Gen 1, Gen 2, Gen 3.

14:28As you know, many people, you know, the thing you probably worry about, I mean, I do, like we see the ups and downs of what the dollars do. But like, it's not that you grew up quote unquote poor, but let's call a spade a spade. You over the last 50 years of your career have changed the trajectory financially of your family. Yes. You're the one who sees it most up close and personal of the biggest divide. It was a slow and steady climb. You created that multiple jump and you can see it and you see what ends up happening with prosperity. and America has had unlimited prosperity now for a long time.

15:05A lot of families go through it is the thing that most people struggle with that work for things. They see entitlement up close and personal. Yeah. Entitlement and lack of accountability drives people that are accountable crazy.

15:24You called it, bro. You called it. It's real. And so, look, you know, again, and then I mentioned it earlier, the thing that the kids have, kudos to them. I mean, my mom and I joke all the time that if I was growing up right now in this era where you could start a Shopify store and have a TikTok, she even said a joke the other day. She's like, forget about college. Definitely you wouldn't have graduated or gone. She goes, but forget about high school. She's like, I'm not even sure. I'm not even sure if you would have graduated middle school. She's like, because by fourth and fifth and sixth grade, I was checked out selling baseball cards.

15:59I think the other thing that I have a lot of empathy for these kids, they don't want to go work at Kmart or Starbucks for 15 or 20 bucks an hour. They literally know that in their hands, the devices started by the pioneers of technology that you grew up with have given them so many goddamn options. My big thing to the kids is if you're not winning with all these options, then you need to be accountable and realize you suck, not the world.

16:28Tough love from Gary V, baby. A little bit. It's, you know, if you have all these options and you don't want to do this grind work because you have all these options and then you're not winning, don't blame the algorithm. Don't blame the audience. Don't blame your parents. Blame yourself. That's how you'll actually get there. Yeah. So let's go back to Remarkable. Because we're just having fun because we enjoy each other. Like, talk to me about the things that really stand. You've really been around Remarkable people. You've obviously got the podcast interviewing so many of them. So you've been thinking about it, your writer's mind, analyzing, pulling out.

17:03Give me here on the podcast like one thing that is very obvious to you that might be a little more subtle. Or if it's tried and true and cliche, which one is like, oh, my God, this is one of the things for damn sure. Well, for damn sure, every one of the people that we interviewed, the remarkable people we interviewed, they had a growth mindset. They did not believe that they are what they are. They cannot be any more, nor did they believe they cannot be any less. So they were always trying to make progress. They were always trying to learn new skills. They always had intellectual curiosity. And they seldom, if ever, rested on their laurels.

17:47Never get high on your own supply. Yeah, never, never. You know, to my knowledge, I don't have any billionaires on my podcast. Certainly not any hedge fund managers. Yeah. And I think to your point, I mean, I think a lot of people that have that DNA, I actually think they enjoy the game. Like for me, there's many behaviors I do that is not maximizing my wealth. It's maximizing my enjoyment of being a builder. Yeah. Yeah. Well, you know, at the end of the day, Gary, I mean, what do you want people to say about you? And what do I want people to say about me? And it's not because you bought the New York Jets or it's not because I donated a building to Stanford, which I'm not going to do.

18:34You know, seriously, if I had Boku bucks like that, like, you know, like donate building bucks, I would give it to the community college system of California. Yeah. That's who needs the money. That's right. I think I think one of the things that has kept me from often publicly talking about what I do in nonprofit is I just watch everyone use nonprofit as a thing to build themselves up. Right. Right. To your point, if you're going to donate, Stanford's the last place that needs it. You're doing that for you. Yeah. Walk by the campus that you learned from. And it's obviously an amazing institution, but you want to see your name there.

19:09And I get it. You want your grandkids to say, like, I think it's highly valuable. But if you're really trying to really make an impact, there are many. I mean, by the way, that's how I got into the two boards I'm on. Pencils of Promise and Charity Water. All their work is done predominantly in Africa. And all of them is done predominantly on things that make no sense to me, which is it is 2024. And 850 million people on earth do not have access to clean water. How can that be? That's how I get excited. Look, there's things. There's a tornado or an earthquake. There's many things in America. that man that one i will i don't know like every night like i think a lot i think about a lot i'm like how is that like clean water i i live in a community of farm workers and i support an organization called digital nest and the whole premise of this organization is to give hispanic kids an alternate career path than agriculture don't get me wrong there's nothing wrong in agriculture okay but you should have options so they teach kids digital skills in the middle of a farm area and that is a beautiful thing and that's my call you know you know i'm not giving money to stanford there's not even a brick at stanford with my name on much less a building guy before we get out of you know get before we get out of here what can people one of the things i'm very proud of is even though I have very poor reading comprehension and I learned by listening and watching, this podcast is a pretty aggressive book buyer.

20:46And so I anticipate a lot of people picking up Think Remarkable by Guy Kawasaki. Who's this for? Have you, and the people that have read it around you, given that you've written 16 incredible books, is there, like, if somebody's listening right now, either the value prop or the for instance or the scenario that you think is a complete no-brainer. Because I agree with you. The thing that I'm most fascinated by is books are so inexpensive to be a concise capture of a moment. My new book also got a lot of purple in mine, right? This, when I tell you, I know bullshit. Day trading attention that comes out, I think in May, is literally what I'm running the strategy of my$350 million marketing agency.

21:30It's our competitive advantage. And I'm literally to the best of my ability putting the most updated information in detail. Yeah. So I always think books are the best deal of information out there still in a weird way. So in this, what is the answer to that question I have for you? The answer to that question is, this is 170 pages that takes the wisdom of 250 remarkable people filtered by someone who's been on the front lines for four decades to give you a manual or a handbook or using apple vernacular oh read me first for life this is it this is this is this is the book that i want to be remembered for that it helped gen z it helped gen z figure out how to be happier.

22:22Yeah. And you know what? Not happier in the sense of now you can buy a big house and a German car. Happier in the sense that I think what makes people truly happy is that they made a difference, not that they made money. And I also say that if you make a difference, you will probably also make money. Well, that's right. Because everyone's counterpoint is like easy for you two guys to say you've made money. And I get it. The problem is you and I are, I mean, you look phenomenal for 60. So are you doing something big for 70? You know what? I, Gary, I, seriously, I, I am such a lucky person. Like, okay, I'm deaf, but you know, cochlear implant kind of helped that.

23:11So there's worse things to be than nobody ever died from deafness. Right. Right. So I, I, I just, as I said before, when I die, I want people to say that I helped them make a difference. That's it. That's what I want my legacy to be. And this book is going to do it. good news you already did it you didn't need this book i mean that guy listen you know you know this we've interacted a dozen plus times at this point on through the years on speaking stages and we even did a book signing together i think it's out by one year and you know i i'm saying this out loud because i want everyone to hear how i feel from the first time we met to today it's always important to me that I give you flowers because you represent an era of communicators that became something that I did as well, not as early as you.

24:03And I believe it became a foundation of our society, which is normal human beings got to become the Walter Cronkites, got to become the internet changed the world and created meritocracy around humans that had good spirit. Everyone wants to focus on what it allowed bad people to do. You and I, especially in 05, 6, 7, 8, 9, 10, there was so much focus on what it was allowing good people to do. And I think you're one of those good people. And I think you will be remembered fondly with or without this book coming out because you've put in the work over the last three decades. You just have. Thank you.

24:44Gary, your blessing on this book means the world to me because I know you're such a hard ass and you don't tolerate bullshit. So yeah, I don't know. To read this book. Honestly, the thing I'm, I'm really stuck. I'm actually very proud of it. I'm shocked how many people reach out to me and talk about the bump on sales. And you know, I'm a businessman. So like, I'm not scared of commerce. I'm not scared of entrepreneurship. I'm not scared of, you know, things selling and I'm very proud of that. They just will. I know this audience. I know that as you know what you did, that is especially remarkable.

25:21How many pages? 170. Yes. I mean, again, people that have, you know, I don't have reading comprehension, but the people that do, like the speed in which they're going to be able to, this is a one night book for some people. Yeah. Which is massive. And very, you know, that was actually the biggest concern of mine. I decided to like put out my best secrets of social media and creative. And so it's actually pretty dense by my standards. I would even argue has parts that might be the most boring of anything I've ever done in book form, but it required it. But I think what you're doing here is snackable and definitely a weekend or a spring.

25:59You know, when's this coming out, Guy? March 6th. Yeah, so I think, again, I've always liked my books that came out that time of year because people really read during spring break. So I think you're gonna get a lot of that kind of action. Anyway, Think Remarkable by Kawasaki and Madison, right? Like we gotta, she's there, we gotta give her love. Looking forward to having the feedback from much of my community who's read it. I wish you well, health, the best day. We'll talk to you soon, Guy. All right, Gary. Thank you so much. Take care. Stay welcome. Bye.

From the publisher

In this 2024 episode, GaryVee sits down with legendary author, entrepreneur, and Apple veteran Guy Kawasaki to talk about his new book and decades of experience shaping business and culture. They dive into lessons from Silicon Valley, the evolution of marketing, and how entrepreneurs can adapt to today’s fast-changing world. A candid conversation between two industry icons on where business and technology are headed next.


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