Neil Patel

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Guy Kawasaki is the co-founder of, an online magazine that offers articles about popular topics. He is also a founding partner at Garage Technology Ventures and the chief evangelist of Canva, an online graphic design tool. Prior to that, he was the chief evangelist of Apple and an advisor to the Motorola business unit of Google. Kawasaki is the author of ten books, including Enchantment, Reality Check, The Art of the Start, Rules for Revolutionaries, How to Drive Your Competition Crazy, Selling the Dream, and The Macintosh Way.

In this episode you will learn:

  • What separates visionaries from the rest
  • Lessons learned from Steve Jobs
  • Patterns to recognize potential successful founders
  • The role of chief evangelists
  • Takeaways from building five companies


For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here) that I recently covered. Thiel was the first angel investor in Facebook with a $500K check that turned into more than $1 billion in cash.

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Moreover, I also provided a commentary on a pitch deck from an Uber competitor that has raised over $400 million (see it here).

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About Guy Kawasaki:


Guy Kawasaki has been a fixture of the tech world since joining Apple’s Macintosh team in the 1980s. He is currently the chief evangelist of Canva, the Australian “unicorn,” and a brand ambassador for Mercedes-Benz.

His bestselling books, including The Art of the Start 2.0, The Art of Social Media, and Enchantment, have established him as an expert in innovation, entrepreneurship, venture capital, and marketing. But his new book is a radical departure from the other fourteen that he’s written.

It’s called WISE GUY: Lessons from a Life and is his most personal book yet. Told in a series of vignettes, WISE GUY explains Guy’s wide range of experiences and the lessons he’s learned from them. Think of it as “Miso Soup for the Soul.”

The book covers everything from moral values to business skills to parenting. As Guy writes, “I hope my stories help you live a more joyous, productive, and meaningful life. If WISE GUY succeeds at this, then that’s the best story of all.” Guy writes on a wide range of experiences and reflects on the lessons he’s applied to his business philosophy and life.

Connect with Guy Kawasaki:


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Alejandro: Alrighty. Hello, everyone, and welcome to the Dealmakers Show. I’m very, very excited about the guest that we have today. So, someone that has been around the block quite a few times on every single perspective that you can think of as an entrepreneur, as an author, as a speaker, as an employee as well. Without further ado, Guy Kawasaki, welcome to the show today.

Guy Kawasaki: Thank you. Good morning.

Alejandro: So, you were born in Hawaii, Guy.

Guy Kawasaki: Yes.

Alejandro: How did you end up studying at Stanford?

Guy Kawasaki: I went to a public school, K-6 public school, and one of my elementary school teachers told my parents to pull me out of the public school system because I had too much potential and get me on a more challenging, faster academic track. So, my parents listened to her. They put me in a private school. From that private school, I went to Stanford. Looking back now, I don’t know how I got into Stanford because I certainly couldn’t get into Stanford today. But you know what, Alejandro, it was so long ago that back then Asian Americans were considered an opposed minority and they needed extra help.

Alejandro: Got it. After graduating, actually you go into law school, and I believe that I read that you only lasted about a week because the professors were not being so nice to you. They were trying to remake you. I wanted to ask you here, what lessons did you learn from rejection?

Guy Kawasaki: Well, they didn’t reject me.

Alejandro: Or maybe you felt that way because when people are telling you stuff that it’s not nice to hear. I think I read that they kept telling you that you were crap or something crazy like that.

Guy Kawasaki: Basically. I guess what I learned from that is just because you quit once, that doesn’t make you a quitter for the rest of your life. Many people, I think, they have this fear that “If I quit one thing, if I quit ballet, if I quit taking language lessons, or if I quit playing Lacrosse, then I’ll quit the next time and the next time, and the next time. Pretty soon, I’ll be homeless, and I’ll be a total, total failure.” No. My experience is sometimes it takes more courage to quit than it is to stick it out. That doesn’t mean you should go and quit everything willy-nilly, but I think there are times in your life when you should quit.

Alejandro: Of course. So then after this, you actually went to do your MBA, and you started doing a little bit of counting diamonds at the Nova. I think that here, you learned one of the most important and most vital things in your career, which is selling. Right?

Guy Kawasaki: Yes.

Alejandro: So, why would you say selling has been so vital in your career, Guy?

Guy Kawasaki: Because in the real world, not the internet world where everything is an AB test, in the real world, if you’re breathing, your selling. You have to sell the person who’s checking you into the airline to let your extra bag be free, and put you in first class in an aisle seat. You have to sell when you apply for a job. When you want a promotion, you have to sell your product or your service. You’re either making or selling every day of your life.

Alejandro: Absolutely. That’s completely true. Guy, after your experience of working for EduWare Services, you got a job at Apple. What year was this?

Guy Kawasaki: This was 1983.

Alejandro: I believe that Apple at that time was like 50 cents a share. I mean, what a ride.

Guy Kawasaki: Well, yeah. No kidding.

Alejandro: Why did you leave in 1987?

Guy Kawasaki: I left in 1987 to start a software company. Basically, I was the Macintosh Evangelist, and I started believing my own hype.

Alejandro: I love it. What was the name of this business?

Guy Kawasaki: ACIUS. It was the American version of a French company.

Alejandro: Got it. What was the trigger of this company? How did you incubate this idea?

Guy Kawasaki: The company was creating a Macintosh relational database that Apple was going to publish. Then Ashton-Tate, a database company back then put the pressure on Apple not to publish it. So, Apple was tearing up the contract, and I was so upset about what Apple did that I decided to leave with the product and start a company with the other founders of the company.

Alejandro: What happened then with the company? With ACIUS?

Guy Kawasaki: I believe it still exists today, and it’s still selling Macintosh relational database.

Alejandro: That’s amazing. I actually went to the website. I was like, “Wow. I can’t believe that this is still up and running.” It’s amazing. I think that right after this is when you actually started writing and speaking, and the rest is history because how many books have you written so far?

Guy Kawasaki: Believe it or not, I’ve written 15 books. I don’t believe it either.

Alejandro: Wow!

Guy Kawasaki: Listen. When I wrote my first book, this is in 1987, I thought I was done, that I had nothing else to say for the rest of my life. It’s pretty amazing.

Alejandro: Wow. Fifteen. I mean, I’ve written one, and I think that’s enough for the rest of my life. I can’t even imagine 15. That’s amazing. And you’re actually launching, if I understand right, your latest book today called Wise Guy. Is this right?

Guy Kawasaki: Yes, it is literally launching today.

Alejandro: Wow. So, what is this book about?

Guy Kawasaki: This book is about 25 bucks. No, this book is about the stories in my life that have shaped my life and taught me lessons. In each case, I tell a story, and then I explain the lesson and the wisdom that I learned from this lesson. So, it’s not an autobiography or a memoir in the sense that I’m giving you a total chronology of my life from the moment I’m born to today. I skip around a lot, and it’s organized by subject, not by a timeline. This is not the kind of book that’s going to be made into a movie. Okay? It’s not like I came over to America in the last helicopter out of the U.S. Embassy in Vietnam, and the U.S. Navy dropped me off in Vallejo, and I had to work at 7-11, and I saved all my money. I went to a college, and then I got lucky. It’s not that kind of story that you’re going to see in the Oscar presentation. I had a very nice, lower-middle-class upbringing. I didn’t have any abuse. I didn’t have to overcome any drug addiction or anything. This is just stories of my life. Kind of like Chicken Soup for the Soul, only it’s all my stories.

Alejandro: Got it. And that’s from Jack Canfield or who wrote that one?

Guy Kawasaki: Yeah, it was Jack Canfield. Yes.

Alejandro: Oh, good stuff. In this book, you’re tackling the personal and also the business aspect. So, it’s like the two things at the same time. Right?

Guy Kawasaki: Yes. There are many things about business innovation, my experiences at Apple, selling, evangelism, social media, speaking, all that kind of stuff because there are a lot of stories because that’s my identity. But I talk a lot about values and parenting and sports and children.

Alejandro: Really cool. Well, I’m definitely looking forward to reading it because I have been a big fan, and with books like The Art of the Start and things like that. They are all recommended reading for founders. Especially for the ones that are listening. Talking about founders, and going back to your own journey. After this experience of ACIUS, you go on to launch your next venture, which is Fog City Software. Is that right?

Guy Kawasaki: Yes. Fog City Software was a Max-offer company, and we made an email client. It was a small company, and we just tried to create really fine Max software. Another fun project.

Alejandro: You talk very highly of your co-founders. How did you meet them?

Guy Kawasaki: At Apple. Will Mayall, who is the co-founder you’re referring to, I met at Apple on the ACIUS relational database project. We’ve been best friends to this day.

Alejandro: Wow. You’ve definitely met a lot of people at Apple, even your wife.

Guy Kawasaki: Yes. Apple’s been very good to me.

Alejandro: That’s fantastic. What was the outcome of this company?

Guy Kawasaki: We sold the product, Claris, the software division of Apple. We kind of finished it, and it’s not like I made a billion dollars off of it. We’re still all friends. It was fine.

Alejandro: I think that being old friends as you said is critical. So, that’s good. Then after this, you returned to Apple. I think it was about 1995. This was a time when Apple was in terrible shape and not the Apple that we know today. How did you find the company at this point?

Guy Kawasaki: When I returned to Apple, Apple was supposed to die. Michael Dell told Steve Jobs to give back the money and close down the company, etc. So, my job was to help maintain the Macintosh cult: they still loved Apple; they still loved Macintosh. It was a very interesting time. It was right before Steve returned to Apple.

Alejandro: What was the culture like or how was it to be there?

Guy Kawasaki: I’ve been in Apple in good times and bad times. It’s never as good as it seems, and it’s never as bad as it seems. It kind of regresses to the mean. I don’t think people were exactly totally depressed and all that. On the other hand, they weren’t in the delusional euphoria that it is today. I like to portray myself as a person who really did a lot of major work to avert a crisis, but between you and me, it wasn’t that hard.  

Alejandro: Got it. What was the experience, Guy, of working with someone like Steve Jobs?

Guy Kawasaki: He was remarkable. Very difficult to work for. A true visionary and I use that word very carefully because I think there’s only been about three visionaries in the history of American business, which is Steve Jobs, Walt Disney, and Elon Musk. So, all the movies, books, and things, all the things, the stories you’ve heard, they’re all true. And yet, I don’t think any of us would trade our time working at Apple for anything. It was a remarkable time, a great experience. I hope everybody gets to work for a Steve Jobs once in their life.

Alejandro: Wow. What would you say made it so difficult to work with him?

Guy Kawasaki: Because he was such a perfectionist. He just basically kicked ass. I don’t know what else to say. That was his shtick. A lot of people like to kick ass. They just aren’t visionary. Well, he’s both.

Alejandro: Yeah. In terms of being a visionary, what made him that great in terms of vision and having that scale?

Guy Kawasaki: I just think that he could really anticipate what people would come to want. It is remarkable. He either knew what people would eventually desire, or he made whatever he wanted to make and made people desire them. He was remarkable.

Alejandro: From your experience, working with him as a leader, you went to do your own thing later one. I guess, from him, what did you learn the most?

Guy Kawasaki: Oh, there are so many lessons. We could go on forever on this.

Alejandro: You can stop after three.

Guy Kawasaki: 1) Your current customers can’t tell you how to create a revolution. They’re just going to tell you how to make better, cheaper, faster, whatever they have from you already. 2) Design counts. It’s not just functionality. People care about design. 3) You should hire people who are better than you at the job because it should be a source of pride when you look around the room, and the people you’ve hired are all better than you at what they do.

Alejandro: Got it. You’ve built companies. You’ve invested in multiple folks. When you’re looking to hire other people, what kind of advice would you give to those people that are listening?

Guy Kawasaki: That general advice is hire people who are better than you, not worse than you, and people who are different skill sets, not the same skill set because you need people to compliment you, not duplicate you.

Alejandro: Yeah. So, you left Apple in 1997 to start to connect entrepreneurs with investors. I found this interesting because this was way before the equity crowdfunding movement or funding platforms or any of that. You’re also quite a visionary, Guy. How did you come up with this concept?

Guy Kawasaki: Which concept?

Alejandro: With this initiative of of really connecting entrepreneurs.

Guy Kawasaki: One of my friends is Rich Karlgaard who’s the publisher of Forbes. He came up with an idea of a website on how to make a business in New York, San Francisco, Munich, Bogotá, and Tokyo. So, we were going to do this series of websites, all these cities of how to do business in each city. Then we met with a lawyer named Craig Johnson, and he had a different take on the idea. His idea was “Focus on just the fundraising for those cities.” That became, helping entrepreneurs in specific locations raise money.

Alejandro: This eventually ended up being Garage Technology Ventures. I’ve seen investments that you guys have done such as Pandora or Motley Fool. So, very, very successful companies. How many investments has Garage Technology Ventures done?

Guy Kawasaki: I don’t even know.

Alejandro: You’ve lost count.

Guy Kawasaki: Dozens. I don’t know. I lost track. I’ve shut my brain off about venture capital.

Alejandro: I love it. In this arena, because you’ve advised a ton of companies, and you’ve seen a lot, what are some of the patterns that you typically recognize behind these entrepreneurs that have the potential to succeed?

Guy Kawasaki: Well, I think the richest vein for entrepreneurs that will succeed in tech are people who are creating products that they want to use. That sounds completely counterintuitive. Right? Because you’re supposed to create the product that has a large and growing market. My observation is that the great tech companies started because two guys in a garage, or a guy and a gal in a garage, or two gals in a garage, they created the personal computer they wanted, the website they wanted, and come to find out, they’re not the only two people in the world that wanted it. So, I think that’s the richest vein. I’m specifically telling you that the richest vein is not marketing-driven where they read some report that says, “IoT is going to be big.” So, they start an IoT company even though they could care less about IoT.

Alejandro: Got it. Is there like a process that you’ve seen because you’re an expert as well in marketing. Is there a process to follow to see if that MBP may be something that people want to use?

Guy Kawasaki: I mean, not to put too glamorous a spin on it, but basically you ship, and you pray. That’s about it.

Alejandro: I hear you. I know the drill. So, talking about shipping and praying. You actually did that a few years after this with AllTop when it was born. What was this initiative all about?

Guy Kawasaki: The AllTop initiative was to create a website where we would curate all the best RSS feeds for each topic. So, for cars, for photography, for food, for Japan, for knitting, all that. We wanted to make it so that people would not have to assemble their own collection of RSS feeds basically.

Alejandro: This website had an amazing amount of traffic. Did you guys experience some type of scaling issues or perhaps scaling things that you learned?

Guy Kawasaki: It never came down to scaling. I mean, that is a high-quality problem. I wish I could be involved with companies who can’t scale fast enough. It’s a high-quality problem.

Alejandro: I hear you. Then after this, you go with Truemors. I believe it was also acquired by NowPublic, but what’s the story behind this company?

Guy Kawasaki: Truemors, the idea was that people—it was kind of my first idea for user-generated news where people would be able to post true rumors. So, rather than wait for established press to find something, we would try to turn everybody into a journalist. It was so-so. It didn’t really take off.

Alejandro: You guys announced the transaction to NowPublic. For example, doing the M&A process did you guys just do it yourselves. Did you have a banker?

Guy Kawasaki: No. This is a small deal, so it was just myself and the CEO of NowPublic.

Alejandro: There are a lot of people that are listening, and perhaps they’re looking at getting their company acquired or doing a transaction or something like this. What kind of advice would you give to these guys so they can get the deal done?

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Guy Kawasaki: My advice is that I think that tech companies are bought, not sold. What that means is that you as the entrepreneur may think, “Oh, Apple is the perfect company to buy me.” Or “Facebook is the perfect company to buy me. If somebody could just introduce me to Tim Cook or introduce me to Sheryl Sandberg, I can convince them why Facebook or Apple has to buy me, or it will be a tragic mistake.” I don’t think it ever works like that. So, the way it works is you create a company. You’re signing up people. You’re kicking ass. Things are going great. Then one day the phone rings, and it’s the M&A person from Apple or the M&A person from Facebook or Google, or whatever, and they say, “Listen. We’d like to get together and have a talk about how we can strategically work together.” So, your job is not to sell your company because let me tell you, Sheryl Sandberg and Tim Cook, they’re getting 100 messages a day. “I have a shrimp farming software company built on the Macintosh platform. There are two million shrimp farmers in the world. It is a strategic market for Apple. So, Tim, I’m going to do you a favor. I’m going to enable you to buy my shrimp farming software company.” That happens 200 times a day. Tim Cook is not going to call you back. So, the way it has to work is somebody says to Tim Cook, “These people are creating something that just fills this tremendous hole in our product offering. We’ve been trying to do this for five years. We haven’t succeeded. You ought to just buy this company.” Then somebody calls you. So, your job is to make a company that the phone rings. That’s it. That’s it. Companies are bought. They are not sold.

Alejandro: I agree, and I think that obviously, for the phone to ring, you need to make sure that you make yourself stand out so that whenever that company is making or placing a bet, you know that they’re going to hear about you. You definitely know how to do that. How do you nowadays really get the word out and to make a splash with your company?

Guy Kawasaki: Well, the start of getting the word out and making a splash is to have a great product because it’s easy to market something that’s great. It’s hard to market crap. So, 1) Make something great. Then God’s gift to all of us is social media. With particularly, I think, Facebook and LinkedIn, how much better can it get? So, make a great product and use social media. It’s kind of simple.

Alejandro: I’ve seen as well that you’ve been chief evangelist for companies like Canva or Mercedes. What does a chief evangelist do?

Guy Kawasaki: Evangelism comes from words meaning bring the good news. So, a chief evangelist is the person who brings the good news for a product such as Macintosh or Canva. Canva is an online graphic design service. If you want to make a book cover, record cover, presentation, flyer, social media graphic, social media profile background, graphics for your blog post, graphics for your website, anything like that, we make anybody into a great designer. So, think of it as PhotoShop for the rest of us. About three million designs are created per day. We sign up more than 100,000 new people per day. So, you know, I’m supposed to bring the good news of that. Let me tell you. It’s not hard to bring the good news of Canva because it is so great.

Alejandro: I love it. And Canva, for example, they’ve raised over 80 million dollars. You’ve been involved with a lot of companies, so I want to ask you how do you see those companies, when they have to go from Series A or Series B, the leadership skills that you see shifting on the founders, how do those need to shape so that they continue to push the venture forward to the successful path.

Guy Kawasaki: At some point, it becomes all about can you build a team and can you scale? But I will tell you if things are going well, any problem can be fixed, literally. Any problem can be fixed. You can find different management. You can do this; do that if the dogs are eating the food. If the dogs are not eating the food, it’s almost impossible to fix that problem. Again, I just keep coming back to the key is to make a great product and get it out there. That is 99% of the battle. The other 1%, all the “strategic” stuff is just not as important. Just make a great product and sell it.

Alejandro: Yeah. Obviously, it’s great that like you were saying, delivering the good news is great, but I think that especially during the early stages, it’s really tough building a company from the ground up. The early days are awful. I’ve been there. I’ve done that. I know what it is to be behind the trenches. I think from your perspective, Guy, and for the people that are listening that perhaps are going through the early phases, what kind of recommendation would you give them?

Guy Kawasaki: Well, get your prototype early. Keep revising it. Understand that entrepreneurship is a process; it’s not an event. To use an athletic metaphor, it’s not a sprint. It’s more a marathon. An even better analogy than a marathon is that it’s a decathlon. You have to do ten things well at once. It’s not just doing one short thing, running for 100 meters as fast as you can.

Alejandro: Got it. If you had the opportunity, Guy, to go the past and give yourself advice before you launched, let’s say your first company that we were talking about, what would that advice be and why?

Guy Kawasaki: My advice would be, stay at Apple because I quit Apple twice, and I turned down Steve for a third job, and if I had not done any of those three things, I wouldn’t be on the phone with you right now because I would be in Tahiti. But, you know, who knew that Apple would become a trillion-dollar company? Not me, man. Let me tell you.

Alejandro: What was that third job, out of curiosity?

Guy Kawasaki: It was to run Apple University, their internal training program for new employees.

Alejandro: Got it. And why did you turn it down?

Guy Kawasaki: I don’t know. I was stupid. Because I didn’t want to work for Steve again because I wanted to create my own company. Who knows? I try to block out those bad memories.

Alejandro: I hear you. From your initiatives, Guy, launching companies, is there one single lesson that if you had to start a company all over again, it would be like absolutely top of mind?

Guy Kawasaki: So, one lesson for launching a company, the top lesson. Well, several things. One is focus on the prototype. The purpose of a company is to create customers. It’s not to make a pitch and raise money. I think many entrepreneurs, they lose sight of the fact that it’s about making a product and making a customer. It’s not about raising money. The purpose of a company is not to raise money. So, to focus on their prototype. Build the prototype that you would want to use. Hope that you’re not the only person in the world who wants to use it. I wish I could tell you that it’s magic and I just gave you the keys to the kingdom. It’s not true. It’s very hard. So, that’s what it takes. There’s a great deal of luck involved. Don’t get me wrong.

Alejandro: Absolutely. I think as they say luck is preparation meets opportunity. Right.

Guy Kawasaki: Yes.

Alejandro: How do you see, Guy, marketing evolving and changing from now to the next couple of years because content, for example, has really taken over. I don’t think that advertising is as appealing as it used to be. So, how do you see it evolving?

Guy Kawasaki: I’m all about social media, providing value via social media, so you earn the right to promote your book, your software, your website. I’m a believer in Facebook, the targeting of Facebook. I realize there’s some controversy with some other things Facebook does, but I don’t know a better way to target a market than Facebook. So, between social media and content, which is a form of social media. You’re providing great content so that people believe you when you tell them to buy your product. I’ve never been a big spend five million dollars on advertising because I’ve never had a five-million-dollar budget. If you had a five-million-dollar budget, I’m not your person. Of course, if you have a five-million-dollar budget, you’re probably not listening to this podcast.

Alejandro: Well, you never know. You never know, Guy.

Guy Kawasaki: I don’t mean to insult your audience, but let’s face it. This is about scrappy entrepreneurs. Right? It’s not about Fortune 500 CMOs.

Alejandro: Right. Absolutely. On the side of writing a book, you’ve written, like you were saying, 15 and today you’re launching your new one. I actually meet with quite a bunch of founders that are looking at becoming a thought leader and putting a book out there and educating people. So, what kind of advice would you give to someone that is thinking about publishing their first book?

Guy Kawasaki: Don’t do it. Seriously.

Alejandro: Why is that?

Guy Kawasaki: If you are a CEO and you’re saying, “I’m thinking of writing a book,” something is wrong because you should not have time to write a book because being a CEO is 150% job. Now, you’re telling me you have time to write a book? I know what it takes to write a book. Okay? You cannot write a book and be a CEO. It just cannot be done. So, now, you might say, “Well, I’m going to use a ghostwriter.” Well, then my problem is, first of all, a ghostwriter still takes up man-width. You have to meet with the ghostwriter. You have to meet with the ghostwriter. But also, then the book is not truly yours. You’re basically spouting off some of your thoughts, and somebody else is really crafting it. I believe that writing a book is an art. So, I don’t think Picasso said, “Well, you know, I have this idea for this woman’s face, and it’s going to have a triangle. It’s going to be black and white here, and color in there. Will you go now and execute that?” So, Picasso, Michael Angelo, the reason why they’re artists is because they did it. Not because they thought about it and had a ghost artist do it. So, that’s one. It’s just a time constraint. The second thing is that the concept that “Ah, I’m going to establish my personal brand, and be a thought leader, and blah, blah, blah,” is also no good. Do you think Steve Jobs and Elon Musk, do you think they ever sat around and said, “How can I position myself as a visionary and thought leader? Maybe I should introduce a computer with a graphic user interface, or maybe I should introduce an electric car.” That wasn’t going through their brain. They were trying to change the world by electrifying cars, or bringing personal computers, or bringing smartphones to market. They weren’t sitting around saying, “How can I make people think I’m a visionary?” Because if you truly are a visionary, you don’t need to spend time thinking about how to make people believe you are a visionary.

Alejandro: Yeah. I love it. So, Guy, what is the best way for folks that are listening to reach out and say hi?

Guy Kawasaki: Probably on LinkedIn. I’m a brave guy. I’ll tell you my email is [email protected]. So, just my name @gmail. I tell you the subject line that will guarantee that I read your email. You ready?

Alejandro: Go ahead.

Guy Kawasaki: The subject line should say, “I loved your latest book.”

Alejandro: I love it.

Guy Kawasaki: If you say that in your subject line, I guarantee you I will read the thing.

Alejandro: How many emails do you receive a day, just out of curiosity?

Guy Kawasaki: Ah, a few hundred.

Alejandro: Oh, my gosh. That sounds stressful. Alrighty. Well, Guy, it has been an honor to have you on the show today. Thank you, so much.

Guy Kawasaki: Thank you. You take care. Okay?

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