Transcript

Guy Kawasaki: Win Every Pitch Using These Timeless Sales Principles | Sales | YAPClassic

From Young and Profiting · Episode page · Watch on YouTube

· 58 min · 10,631 words · 112 timestamped sections

This is the full, timestamped transcript of "Guy Kawasaki: Win Every Pitch Using These Timeless Sales Principles | Sales | YAPClassic", an episode of Young and Profiting published January 2, 2026 (58 min, about 10,631 words). It mentions 13 people, works and ideas, including Apple Inc., Canva, Young and Profiting Podcast, Goldman Sachs, Tiffany.

What is discussed, and when

  1. – 5:00: Tiffany, Young and Profiting Podcast
  2. – 10:00: Goldman Sachs
  3. – 35:00: Young and Profiting Podcast
  4. – 45:00: Clowner Perkins, Goldman Sachs, Guy Kawasaki, Sequoia

Notable quotes from "Guy Kawasaki: Win Every Pitch Using These Timeless Sales Principles | Sales | YAPClassic"

  • Hey guy, welcome to Young and Profiting Podcast.
    about Young and Profiting Podcast · at
  • Tiffany, Tivol, Bailey Banks and Bidd, those kinds of high-end jewelry store. And the jewelry business is hand-to-hand combat, manufacturer and retailer in terms of selling. So, it's.
    about Tiffany · at
  • Have the most amazing pedigree, Harvard MBA, Yale undergraduate, summer internship at Goldman Sachs, you work for Mckenzie for a year. So you got this perfect background, but…
    about Goldman Sachs · at
  • Wrong. I have never ever said that and I've said in thousands of pitches. So, there's the guy Kawasaki 1020 or 30 rule which is 10 slides in 20 minutes, 30 point font minimum. So, that's a good sort of foundation or framework. the other.
    about Guy Kawasaki · at
  • To John Door, right? Or, the general partner, the big cheese at Sequoia or Clowner Perkins or, whoever, right? We'd love to pitch to Elon Musk. We'd love to pitch to Tim Cook…
    about Clowner Perkins · at

Who and what is mentioned in this episode?

People

  • Guy Kawasaki — Person · 1 mention · first at
  • Tim Cook — Person · 1 mention · first at
    Whoever, right? We'd love to pitch to Elon Musk. We'd love to pitch to Tim Cook, etc., etc. But I'm telling you, when you start off, you should just pitch to anybody who…

Companies & orgs

  • Apple Inc. — Company · 4 mentions
  • Canva — Company · 4 mentions
  • Goldman Sachs — Company · 2 mentions · first at
  • Tiffany — Company · 1 mention · first at
  • Clowner Perkins — Company · 1 mention · first at
  • Sequoia — Company · 1 mention · first at
    To John Door, right? Or, the general partner, the big cheese at Sequoia or Clowner Perkins or, whoever, right? We'd love to pitch to Elon Musk. We'd love to pitch to Tim Cook…
  • HP Inc. — Company · 1 mention
  • Yahoo — Company · 1 mention
  • Yale — Company · 1 mention

Concepts & topics

Full transcript with timestamps

Hello, young and profiters. We're kicking off the first YAP Classic of the new year. So, welcome to 2026. And there's no better way to start off a year of growth, opportunity, and leveling up than by exploring the fundamentals of what truly drives a remarkable career. We're rewinding to my conversation with Guy Kawazaki, legendary marketer, former chief evangelist at Apple, and current chief evangelist at Canva. Guy's career is full of bold pivots, unexpected opportunities, and practical lessons drawn from decades in Silicon Valley. In this interview, he breaks down what true evangelism means, why sales is the most important skill in business, and how to pitch and demo like a pro. Guy also shares candid stories about working with Steve Jobs, the role luck played in his biggest breaks, and how stacking skills from every job can transform your future. By the end of this conversation, you'll have a clearer picture of how

exceptional careers are truly built. So, let's dive right into my chat with Guy Kawazaki. Hey guy, welcome to Young and Profiting Podcast.

Thank you. Thank you for having me. It is such an honor to have you on the show. It seems like I hear your name all the time. You are also rocking the podcasting space. You're a host of the Remarkable People podcast. You're also a very in- demand keynote speaker, the author of 15 books. And as for your day job, you are currently the chief evangelist of Canva, which I love that software. And previously, you're also the chief evangelist at Apple, and you're well known for helping Apple become a household name. In fact, you are known to have popularized secular evangelism during your time at Apple.

And so, I feel like Apple is a great place to start this conversation when it comes to your journey. It was a long time ago, but it's super relevant still and I think lots of great lessons. And from my understanding, you had no technical background before you worked at Apple. You had a degree in psychology. You were a law school dropout and your former college roommate actually got you the job. And this was pre-Apple that we know today. So 1983, the year before Macintosh came out and changed the world. And you were getting your MBA. You worked at a jewelry factory. And you said what you learned at the jewelry factory actually translated to your new job at Apple. So I thought that was really interesting. I always talk about skill stacking. So take us back to your 20-year-old Kawazaki days right before you landed your job at Apple. What were you like?

How did you get your foot in the door? And how did your experience in sales translate to your job at Apple?

So I worked for a jewelry manufacturer in downtown Los Angeles. And this manufacturer sold two retailers. Tiffany, Tivol, you know, Bailey Banks and Bidd, those kinds of high-end jewelry store. And the jewelry business is hand-to-hand combat, manufacturer and retailer in terms of selling. So, it's not at all like today's idea of selling where, you know, let's test the blue line versus the red line to see if it increases clickthrough or, you know, let's see if this background influences clickthrough. Nothing like that. This was open up a suitcase of samples and pray for an order. So that that's what it was like. And from that experience, I truly learned how to sell. And that selling skill because it was necessary.

You either sold or you died. So that translated into evangelism and has helped me the rest of my career. Now you have many entrepreneurs listening to this and let me just cut to the chase here. As an entrepreneur, there are only two important functions, making it and selling it. And so, if you're the engineer, you've got to make it. And if you're the salesperson, marketing person, evangelist, social media person, it's all about selling. And so, you the greatest example ever of this is W and Jobs. So, you know, Jobs couldn't design the motherboard and couldn't design the computer and was couldn't sell. So, it worked out perfectly. laws could design and jobs could sell. And yeah, that's the genesis of Apple. So, if you're an entrepreneur and you're listening to this, you just need to understand that you fundamentally need two people. Um, one to sell and one to make and the rest is, you know, the rest is

extra. I love that. I always say that sales skills is such an important job. And for me, I remember I worked like 10 or 12 different jobs in retail, working at every store in the mall. And back then I was making minimum wage or, you know, barely making any money. But that's translated into millions, you know, 10 years later as I'm using the same skills as an entrepreneur because my main job to your point is selling whether I'm landing sponsorships or or selling social media to my clients. You've got to sell as an entrepreneur. So, I'd love to hear about, you know, what were some of the key lessons you learned in terms of building trust and making sales at your time either at Apple or the jewelry factory? Like, what are your biggest like sales tips?

Well, one of the things that I learned at Apple and in the jewelry business is that fundamentally, well, I call it guy's golden touch. So, guy's golden touch is not whatever I touch turns to gold. I wish that was true. A guy's golden touch is whatever his gold guy touches. And by that I mean, you know, the key to sales and evangelism is that you're selling and evangelize something good. Because it's easy to evangelize and sell something good. It's hard to evangelize and sell So guess what? Don't affiliate with Duh. Now that is a duhism, but you'd be amazed at how many people don't understand that. So that that's I would say 80% of sales have a great product.

Yeah. And so when you got Apple, what was your actual job title? Yeah. No, my actual job title was software evangelist. So my job was to convince companies to write software for Macintosh. And now you have to understand that evangelism comes from a Greek word meaning bringing the good news. So I was in the position of bringing the good news to developers. that Macintosh was a a new platform, new kind of reach to a different kind of customer. It prevented you from having overdependence on IBM software, IBM market. And it finally for the engineer it offered the kind of richness and development environment that you could write the kind of software that you always wanted to write. And so this was good news for a company. It was new customers in new markets with cool, you know, potential for graphics. Uh, that was the good news of Macintosh in the developer sense. In the consumer sense, the good news of Apple was

democratizing personal computing that people who could not have used a computer because of the the user interface challenges before could now use a Macintosh. And today I'm chief evangelist of Canva and it's the same thing. Canva has democratized design. So now you don't have to be an expert in Photoshop or have a graphic designer uh in your company or in your group or be an a graphic designer. Now you can create your own beautiful graphics.

Yeah. So I I read your book called Wise Guy and you had a lot of lessons in there that I really liked and one of them was just get in the door, right? And you rose up the ranks in Apple. I think you ended up directly working with Steve Jobs and obviously you didn't start out that way. And so I'd love to hear your advice because I have so many young professionals trying to get their big break. They're looking for their dream job and they don't realize that it starts with maybe the internship and you work your ass off until you get your dream job.

I think very few people initially get their dream job. Frankly, I'd make the case that when you're fresh out of college or, you know, in in that bracket, you don't know what your dream job is. you don't have enough data to judge. So, um, particularly for this generation, your generation, over the course of your career, you'll probably have 10 or 15 jobs. So, you know, you shouldn't exactly sweat that that you don't like the first two or three because there's 12 more to come. And it it's different in my age bracket and older. You know, if you went to work for IBM in the 70s or the 80s, you expected to retire or die at IBM or HP. And that's just not true for your generation. So, several pieces of wisdom. So, piece of wisdom number one is it does not matter how you get in.

So, I got in because of nepotism. I got in because of my college roommate. Other than that, I had very few qualifications. Arguably may or may not have any qualifications. So, I got in because of nepotism. But now, the important thing to know about nepotism or however you got in is that it's not how you get in, it's what you do once you get in. Because the day after I started at Apple, nobody gave a that I worked for this guy or that I went to college with this guy. At that point, it was you either are productive and useful and valuable or you're not.

It doesn't matter. And now that can work both ways, right? So if you have no background like me and you get in and you prove you're valuable, nobody cares that you didn't have a background. The flip side is also true. So you could have the most amazing pedigree, Harvard MBA, Yale undergraduate, you know, summer internship at Goldman Sachs, you work for Mckenzie for a year. So you got this perfect perfect background, but then you started a company and you are useless. Well, guess what? Nobody cares that you work for McKenzie or Goldman Sachs or you went to Harvard or Yale.

You are just useless. And so that's a very important letter lesson. It doesn't matter how you got in. It matters what you do once you got in.

I love that advice. And while we're on advice for like the younger, you know, bracket of my audience, I heard you once say, and I wasn't planning on bringing this up, but I feel like it's very relevant. You were saying that um people should stay in college as long as they can. You said it was pretty funny. you were like, "Try to stay five years, not four years if you can." I'd love for you to touch on that a little.

Of course, this does not apply to my children, but I think that college is one of the last times in your life where you are truly free. I mean, your your biggest problem is your chemistry midterm or your English paper that's due, right? And so this is the last time that those things are seeming big challenges and crisis. The for the rest of your life, you're going to be worried about making money, paying off student loans, finding a you know lifelong partner. God help you when you have kids. Then you know you completely lose control of your life. And so you should enjoy college as long as you can. And with hindsight, I graduated in three and a half years because you I'm an Asian-American. I was like overly driven to to graduate fast. Um, and I didn't take advantage of things. So, I could have gone to an overseas campus. You know, the school that I went to had overseas in London and, you know, Brazil

and Japan and, you know, you name it, they had an overseas campus. But no, I was the dumbass who wanted to graduate as fast as possible. I wish I had gone to an overseas campus.

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I've overcome that. So, let's turn it on the flip side. You, you know, you've worked at Apple, you've worked at Canva. What are some of the biggest lessons that you've learned along the way when it comes to managing a team, employee recruitment, employee retention? So the biggest lesson that I learned in employee recruitment and retention and optimization really is to hire better than yourself that it should be a source of pride that when you look around the room, the people you've hired are better at the function than you could ever be. Um, as we said in the Macintosh division, you know, A players hire A players, B players hire C players, C players hire D players. I've subsequently modified that so that A players hire A+ players. And this takes uh some self-confidence. You if you look around the room and everybody in the room does their job better than you could ever and you're the CEO, you might

think, "Oh my god, you know, I'm supposed to be the the big dog and I'm not." Well, I think the ultimate confirmation of you being the big dog is you're big enough to hire people who are better than you.

I love that advice and it's so true. you do kind of need confidence for that. Some people are too cocky to do that, but that's not how you get ahead. So, speaking of bosses, um I heard you on another show. I do a lot of research for this show and and you talked about the hardest bosses and teachers being the best bosses and you were you mentioned Steve Jobs being your hardest boss, which I just think it's so cool you got to work with him. And then also your English teacher in high school was your hardest boss. But you didn't say what they taught you.

Well, my English teacher taught me about grammar and writing, you know, no question. And grammar seems to be less and less important these days, but in those days, he just drilled it into us. So, I learned about writing, the just the the rigors of writing from Steve Jobs. Oh my god, I learned so much. I mean, I learned that uh you can't ask your current customers how to innovate because all they want is better, faster, cheaper. I learned that A players hire A players or even better A+ players. I learned that if people believe in what you believe in, they will go through all sorts of lengths to help you. That's evangelism.

And I also learned some stuff from Steve Jobs in a in a sense of what not to do because uh he was extremely demanding, even scary to work for. It's not clear to me that that's necessary uh to succeed.

Interesting. I love that. And so, like I said, I've been listening to a lot of interviews. So, Jordan Harbinger is actually my mentor and one of my closest friends. And you guys were having a conversation about luck. And you guys got down this rabbit hole about how Steve Jobs, you know, Jeff Bezos, Mark Zuckerberg, Elon Musk, they had a lot of luck with their journey. And you were arguing that they are smart, but they're not that much different than everybody else. And so I couldn't tell if this was motivating or like depressing because on one side it's it's a good thing that, you know, we all could potentially achieve that kind of greatness. I don't know if I exactly said that Jeff Bezos, Steve Jobs, and Elon Musk are not any smarter than any of us. I and I, you know, the person I know best is Steve Jobs, and he's on a different plane of intelligence. Okay? So, let's let's concede that. Having said that, um if if

you gave me a choice of here's a lucky CEO and here's a smart one, I probably would pick the lucky one based on what I know today. uh and and now when you have a Steve Jobs who is both lucky and smart and could actually influence both sides. So if you're smart, you may influence your luck because you'll be in the right place at the right time. And if you're lucky, um then you'll seem smart. So I it's not exactly a um you know either or. You can be both and arguably those people are both. But I what I'm my point was that uh it it's not just about you.

There are plenty of smart people in the world and some of them have just been unlucky. Some of them have picked the wrong thing. Some have been in the wrong place at the wrong time etc etc. So if if you start believing that you know you are God's given gift to entrepreneurship then you're going down a bad path. So you should be you should be humble enough to understand that you know it takes a lot of things to be successful. One of which is luck

and I want to understand do you feel like there's any way to like maximize our chances to get lucky?

Well you know part of it is just showing up right. So you have to show up. I mean, luck there's a saying, a Chinese saying that you have to stand by the side of the river a long time before the roast duck will fly into your mouth, right? Which which is to say um you know, you can't just depend on luck. You have to go make the luck happen and you have to be in the game. If you're an entrepreneur, well, if you truly believe in luck too much, you may believe that you don't even have to be an entrepreneur. That someday, you know, I don't know what, fortune will smile upon you and bada bing, bada bang, you're presented with the next apple.

That's not going to happen. You have to go start the apple. You have to go fail a few times. And that's just the way it works. Um, if if it was easy to be an entrepreneur, believe me, more people would be one.

Yeah, I totally agree. So, let's talk about quitting, right? So, another life lesson that you often talk about is quitting. You quit law school, I think just a couple weeks in. And I agree, the times that I've quit something in my life were some of the best decisions in my life because it it opened up the opportunity to do something different. And sometimes you've got to let go of good to get something great. And, you know, it actually reminded me of something I I interviewed this guy Colin O'Ry yesterday. He's this like endurance athlete. He's crossed over Antarctica unassisted. He's rode through Drake's Passage, which has claimed the lives of like 20,000 sailors. And he told me something that like really imprinted on me. And it was that life is a scale of 1 to 10, right? So tens are like the biggest milestones in your life, you know, crushing it with some sort of accomplishment, having a baby. Ones is

like going bankrupt, you know, getting divorced, all those bad things. And people tend to stay at five, you know what I mean? They're comfortable. They every day is just five, five, five because they're worried about hitting a one or a two, right? And they never get a nine or a 10 because they're just staying at five. And so I feel like that is very relevant to, you know, taking a chance to doing something like quitting because people are just so afraid of failing. So I'd love to hear your perspective on quitting and why it's not failing and just your thoughts on that.

Several thoughts, some of which may conflict. First of all, quitting takes courage. It I don't know about you, but for me, it took a lot of courage to quit because I was in such this, you know, Asian-American path of going to this prestigious school, then going to law school, and, you know, it was all planned out being doctor, lawyer, or dentist, right? So, getting off that track and wasting the efforts of 2,000 years of my family took some courage. Uh now I interviewed Angela Duckworth and she had a very interesting take on quitting which is she says you can quit but you should quit when it's a good day. So let's say we'll take a example. Let's say that you're taking the violin and you you're not allowed to quit because you are not progressing on violin. You can quit if you're doing well with violin and you just decide that you don't like it.

That's okay. But quitting before you even get to that point is not okay. There's a very interesting perspective on quitting. That's easy for her to say and me to say, not necessarily to do. But anyway, so that's an interesting thing about quitting. You just, you know, you have to quit in the right way for the right reason at the right time. You know, I quit that law school. I have no regret about that. The concept of a slippery slope is vastly overrated. So, you know, you can make the case, oh god, you quit law school, so now you're a quitter. you know, you're not going to be successful for the rest of your life.

You're just going to be a bum because you quit law school. Well, that didn't exactly work out that way. And and I think if you look at many things, um the referral to the slippery slope is vastly vastly overblown that you know, if you require background checks to buy an AR-15, next thing you know, you're going to be taking away my guns. That's a slippery slope fear, right? But it ain't true. I mean, you know, so so you need to beware of being too afraid of the slippery slope. Now, if you quit three or four things in a row, you probably should be worried about the sl of, you know, you are going down that slope, but quitting one thing, I don't think so.

I think in your case, you quit, but it's not like you decided you weren't going to work or or like keep on hustling and trying to make it. You found something that you enjoyed more. So, I totally agree there.

I would say my observation is most people stay too long rather than quit too early. But I got to give you a huge caveat with that. But I also have come to believe the concept that the grass is always greener is not true and that sometimes you should fertilize and water the grass you're standing on, not try to find greener grass.

Are you alluding to you leaving Apple by any chance? Exactly. talk to us about that.

Well, I left Apple twice actually. Um, once because I wanted to start a company. Actually, both times because I wanted to start a company. But, you know, let's be honest, when you leave a company to start another company, you could talk about all the romance of entrepreneurship and you wanted to dent the universe and blah blah blah blah, but it fundamentally at some level it means that you are not happy or you don't believe in where you are, right? I mean, there's got to be some piece of your decision that is tied to that. It cannot purely be all this amazing upside. Listen, if if you had told me when I quit in 87 and 97 that Apple would become a $2 trillion company, I would have told you you are on hard drugs.

Like hard illegal drugs. There is no way. The first time I quit Apple, it's not clear that Apple would have survived. So, you know, who knows? Who knows? So, sometimes you should just stick with it. Now, this might not play well with your generation who I just said is going to have 12 to 15 jobs over their career, but uh at least my experience, you know, I I know people who had a great one or two years at Salesforce and left because at this point, you know, at that point Salesforce was already large, publicly traded. They weren't handing out big options anymore. It was hard to see, you know, how they're going to make millions and millions of dollars and rise into this large organization.

Well, you know, it's too early to really assess that decision, right? Because I left Apple in uh 97 and it didn't become a trillion dollar company to, I don't know, 2017 or whatever it was, right? So, you it took 20 years. Now, you might say, well, who wants to work for the same company for 20 years? But that's dependent on what you're doing and how you're growing, not necessarily just going to the same parking space for 20 years. So I know this is this interview is filled with inherent conflicts that I just want people to realize who's listening that yes I am conflicting myself. It's not that I'm stupid. I know I'm conflicting myself but you have to understand that that is how life goes.

You know it's not black and white and I am just one data point. And you know with entrepreneurs in particular, I'll give you a classic entrepreneurial thing that one theory says you take your shot and then you pivot quickly. Another says no matter what the negativity and naysaying is about your product, if you believe you stick through it, that you stick with it and you pop out the other side. Those are two completely different things, right? Pivot or grid it out. Both have worked. So it kind of depends on well what's the last podcast?

Exactly. Who was the last person I talked to about this? Right. Exactly. I love it. But you know what? There's many paths to success. You know, like you said, people succeed one way or another. And you've succeeded even though you've made decisions that maybe you kind of regret, but at the end of the day, that maybe that wasn't your path, right? So, let's talk about some of these decisions cuz you didn't go to um Apple. You quit Apple twice. Then Steve Jobs, I think, asked you back a third time. You said no. You almost got to be the CEO of Yahoo, right?

Yeah. Well, that's an overstatement. I was asked to interview and let's let's take the worst case. Let's say I got asked to interview and I I was offered the job.

You could have been this the CEO of Yahoo. And I guess that was before Yahoo was Yahoo, right?

Well, yeah. That's so that you know that right there. That's two billion. Those are billion dollar decisions. Have you learned anything about decision- making where do you feel like you've gotten better at it or do you just feel like again it's this luck idea of luck?

Who among us doesn't think they're getting better at decision making? But let's just say we're not all right. So I don't know. Listen, I you I turned down this opportunity with Yahoo. I quit Apple twice. I turned Steve Jobs down for another offer. So there, you know, there's four right there, right? So that would be roughly I'd say$2.5 billion dollars total and you know 2.5 billion here 2 and a half billion there. It adds up to real money after a while. So maybe people are turning off this podcast right now because they're saying why would I listen to this dumbass who left Apple twice and turned down Yahoo?

I should go listen to someone who, you know, did everything right in his or her life, which is kind of the empty set. But yeah, so a lot of it is positioning and branding often in your own mind. So in my mind, the way I explain myself is okay, so you know, I worked at Apple and Canva. Ah, who's going to say you're a failure, right? I mean, Apple and Canva, I mean, that's that's two very good acts, right? I mean I think you are far from a failure. You are very successful and Canva is like becoming this huge company. I mean you really found a unicorn. You do know how to pick them.

Well, okay. Let's let's discuss that. Okay. Because it's very important that I think entrepreneurs truly understand what goes on. So I started with Apple because of nepotism, right? Then I left Apple. I started a company. I went back. I started another company. Those two companies you would not have heard of because they were moderate if successful at all. As a venture capitalist, I probably put down I don't know 15 bets or something. So if you if you just looked at the numbers, if you just were a you know a numerical geek, you'd say, "Okay guys, so you have Apple and Canva and you have 15 failures. So guy is two for 17." So that's one way of looking at it. The way I look at it is I may be two for 17, but look at the two.

Look at the two. And and you're, you know, everybody knows who you are. You're hosting a popular pot. You're being way too modest. You've written 15. But come on. [snorts]

No, no, no. Well, you know, but listen, I'm I'm not a trillionaire. I'm not a billionaire. I'm, you know, I just like I'm a surfer. I just like to like to surf and podcast. That's what I do. I surf and podcast. That's my I have decided that you know my podcast I'm on a mission to make people remarkable with my podcast. And it's not because of my wisdom. It's the wisdom of people I interview such as if you're an entrepreneur. I've interviewed Steve Waznjak. I've interviewed the CEO of PooPourri which is a great story. Don't laugh at that story. Susie Batiz uh Frey Farm the most pumpkins. Uh the hint water. So, I have a lot of different kinds of uh entrepreneurs in my podcast and you know, I think my podcast is actually over the course of my lifetime.

I've been an evangelist, I've been an investor, I've been an advisor, you know, whatever, etc., etc. The best work I've ever done is my podcast without question. It's also the least appreciated. I might be able to help you there. But I have to I have to say uh my client Marshall Goldsmith went on your podcast and we were planning to put out a podcast and you were so good at the podcast that he literally came to me in a meeting and he was like holla I don't think I want to do this podcast anymore. And I was like why Marshall you were so excited about it. And he's like I went on this guy's podcast guy Kawazaki and he was so good and so prepared and this is just way too much work. I cannot be doing this and holla and I was like, "All right, we'll switch gears. Whatever you want, Marshall."

Okay, this this is a great story. So, of course, I've been on the other side of this discussion, right? So, one day I get an email from Marshall Goldmith. And I hope people out there understand who Marshall Goldsmith is. He's like, you know, the living Peter Ducker. Of course, they may not know who Peter Ducker is, but so Marshall Goldsmith is arguably the best executive coach in the world, maybe ever. He's way up there. And so he sends me this email. I says, "Guy, you changed my life." And I said, "Is this spam?"

So, so he says, you know, give me a call to schedule a time. So, I call him and it's really him. And he says, you know, guy, he tells me this story that he was on my podcast and he listened to it. is so well done and I was so well prepared. He just doesn't want to do it anymore. So he said he told me, "God, you you changed my life. You made my life better cuz I was going to try this and it's too much work and it's too hard. I don't want to do it anymore." And so that is like one of the greatest forms of praise.

How funny is it that it's all coming full circle and then I'm the one behind it. So funny. So funny.

I want all you people listening to this podcast that Hala is a fantastic interviewer. And I say that and I consider myself a fantastic interviewer. So

that's so sweet. Thank you so much. That's so nice. So let's get back to the actionable advice for these young and profiting podcast listeners.

The lesson here is 99.9% of the people whether it's podcasting or entrepreneurship or you know whatever don't freaking prepare. They think they're just, you know, a a very good example of this is pitching your company. So, most entrepreneurs believe that they're natural communicators. They're going to rise to the top. They're going to rise to the occasion and they're going to just pitch from their hearts and it's going to work out right because they're a natural. And that's total unequivocal And so, you know, you need to prepare. If Steve Jobs, if Steve Jobs used to prepare for weeks for a keynote, and if Steve Jobs needs to prepare for weeks, guess what? You are not Steve Jobs. Not you. Holla, you listening. You are not Steve Jobs. So, if Steve Jobs needed weeks, you probably need months.

Hello, young and profits. Running my own business has been one of the most rewarding things I've ever done. But I won't lie to you. In those early days of setting it up, I feel like I was jumping on a cliff with no parachute. I'm not really good at that kind of stuff. I'm really good at marketing, sales, growing a business, offers, but I had so many questions and zero idea where to find the answers when it came to starting an official business. I wish I had known about Northwest Registered Agent back when I was starting Yap Media. And if you're an entrepreneur, you need to know what Northwest Registered Agent is.

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Get more with Northwestregistered agent at northwestregisteredagent.com/yapfree. That's yap free. Happy new year. Yap fam. I just love the unique energy of the new year. There's something about it that makes fresh starts feel possible and encouraged. And if you've been thinking about starting a business, this is your sign. I mean, you already have what you need. The idea, the skill, and the passion. 2026 can be the year that you build something that's truly yours, and it starts with Shopify. I built plenty of my own businesses on Shopify, including my LinkedIn secrets masterass.

I built my site quickly in just a couple of days. Payments were set up super easily, and none of the technical stuff slowed me down like it usually does because Shopify is just so intuitive. And this choice of using Shopify helped me scale my masterass to over $500,000 in revenue in our first year. Shopify gives you everything you need to sell online and in person, just like the millions of entrepreneurs that they power, you can build your dream store using hundreds of beautiful templates, and setup is fast with built-in AI tools that can help you write product descriptions and edit your photos. Plus, marketing is built in so you can create email and social campaigns easily. And as you grow, Shopify can scale right along with your business. In 2026, stop waiting and start selling with Shopify.

Sign up for your $1 per month trial and start selling today at shopify.com/halla. Again, that's shopify.com/halla. That's shopify.com/halla.ha. Yap fam, here your first this new year with Shopify by your side. And I have to say having a good pitch skills, being able to demo your product. This is so key. I have a funny story too. So when I was first starting Yap Media, I was just I had my podcast two years into it. grew this brand. You know, people were asking me to be their client. I kept pushing it away and then finally was like, fine, I'll give this a shot. I had volunteers and interns and I was like, I'll I'll hire them, right? I remember I went I had a billionaire that was interested in my services. His name is Jason Waller, still my client. And I had no website. I had no logo. I wasn't even incorporated, right? I had no trademark, nothing. All I had was my PowerPoint presentation skills and I was a good presenter and I

did it for myself already. And so I went in, I gave a pitch, and I closed like my first deal was a $30,000 monthly retainer from a freaking PowerPoint presentation that I just designed really nicely. And so it just goes to show you like if you can pitch and demo, you can make so much out of literally nothing.

The lesson there is you got to show up and you got to be gritty, right? It's not, you know, as as as I said before, standing by the side of the river, the roast duck is not going to fly in your mouth.

Yeah. But I want to hear more advice about your pitching skills because I know that you talk about it a lot with evangelism. So like what should we do? How should we prepare for a demo? Like what do we need to know?

The key to a pitch is the preparation. And the preparation for an entrepreneur, let's say you're pitching to a venture capital firm, right? So you have better know who's in that room, where they came from, you know, what school did they go to, what are their interests, what are they invested in, what boards are they on, everything like that. You're looking for hooks that, oh, we both went to Stanford, we both like to surf. Um, you you're on the board of Copper and I love Copper, you know, as my CRM solution. You gota you're looking for hooks to differentiate yourself from the other dumb asses that came in at 8 9 10 1 2 and three. You're the four o'clock appointment, right? So everybody said we have patent pending curve jumping paradigm shifting way to dent the universe. We're going to provide you with, you know, unbelievable shareholder returns while enabling our employees to self-actualize their life goals or

exceeding the expectations of our customers. Every entrepreneur says that. Nobody says, "I'm a dumbass who's lazy." Okay? So, you have to find hooks. And the hooks are, you know, LinkedIn is God's gift to pitching. Basically, if you if you don't study LinkedIn before a pitch, something is wrong with you. You're an idiot. It's like have a sign on your head that says, "I am clueless." So, that's the preparation. I think an initial concept is you can never be too brief. I've never sat in a presentation or a pitch and said, "This was too short. it was too succinct. Something is wrong. I have never ever said that and I've said in thousands of pitches. So, you know, there's the guy Kawasaki 1020 or 30 rule which is 10 slides in 20 minutes, 30 point font minimum. So, that's a good sort of foundation or framework. Um the other metaphor that I would love for entrepreneurs to understand is that think of yourself as an airplane

or a pilot in an airplane and at two ends of the spectrum in airplanes. There is the 787 airbus A380 at one end and at the other end there's the F-15, there's the you know the F-18, the whatever. And so the A380 and the 787, they have two miles of runway and they go rumbling downahove and then at the end of two miles they take off and everybody says, "How the hell can half a million pounds ever exceed?" But anyway, so you know, it's a miracle that those planes take off. At the other end, you're on an aircraft carrier, you get in this plane, you have 150 m to get off the flight deck or you fall in the water and you die. Okay?

[snorts] And I think most entrepreneurs think they are piloting a 787. So they come into this pitch and they say, "Well, let me tell you my life story. You know, my great-grandfather came over on the Mayflower and he landed in New Cananan connected and then he started a horseshoe business and he went and like and then and then okay, finally, so you know, then they made it rich. So they endowed a a fellowship at Yale and I got into Yale and then that first summer I worked at Goldman Sachs and then I got an Harvard MBA and I started at HP in the internship program and then I took Windows, you know, uh, Windows classes and finally I decided to start a company. Okay, that's the Airbus A380. The F-18 pilot has got to get off the deck and you should be an F-18 pilot. So in the first 30 seconds, everybody in that room should understand what you do. I have sat in so many pitches where they're talking about

their whole family heritage, their education, their strategy, the size of the internet. Oh, the internet's going to be big. You know that, right? So let me explain how big the internet will be. And this is right now. This is, you know, and so there this Airbus A380 trying to get down this two-mile runway. And I'm sitting there, I'm thinking, is this hardware? Is this software? Is this e-commerce? Is this social networking? Is this AI? What the hell do they do? And so the I think the most important lessons are be brief, prepare, and get your ass off the tarmac as fast as you can. 30 seconds into it, they should understand this is a software company.

This is a cloud-based software company. What does Canva do? It democratizes design. So you don't need Photoshop. There, I said it. five seconds.

I love that. And practice, right? I'll hop on discovery calls. I know they can't afford my services and I'll just do it to practice, right? Practice your pitch. Um, how about who we should pitch to, right? So, there's the right people and the wrong people and some of them are really uphill battle. So, I'd love to hear that.

Well, you may not agree with this piece of advice, but I think that when you're starting out, you should pitch to anybody who listen. I don't think you can be proud. Now, of course, you know, we'd all like to pitch to John Door, right? Or or, you know, the the general partner, the big the big cheese at Sequoia or Clowner Perkins or, you know, whoever, right? We'd love to pitch to Elon Musk. We'd love to pitch to Tim Cook, etc., etc. But I'm telling you, when you start off, you should just pitch to anybody who listen. And it's for the reason that you mentioned that, you know, yeah, you may be starting with a summer intern who's not going to make a decision to write you a check for five million bucks. But, you know, 20 summer interns later, you will be meeting with a partner. At that point, it's too late.

You need to have had 25 rejections and 25 practice sessions to be ready for this great meeting. And you have to pay the price. So, what about like more generally though? Like, and when it comes to evangelism and trying to market a product, you don't want to market a product to people who just don't believe in it, right? You want to go agnostic. I want to hear those lessons from you.

You're spitting words back at me that I wrote. So, um I I would say that here here we go with some, you know, sort of conflicting advice. On the one hand, I would say that you should pitch even a product to anybody who will listen. It's good practice and you may never know. You may think that this person is not qualified, but you know that this is a summer intern or secretary, administrative aid, customer service manager, whatever. Not the decision maker, but guess what? the decision maker is listening to this person because this person did really does the work or this person you're pitching to spouse is a decision maker at another company. You just never know.

So I'm really into indiscriminate pitches. I think it's also humbling that you know you should not think that you are so freaking important that unless you are talking to the CXO uh this company is not worthy of your time. Like frankly you know you're you're full of Anyway, so that's one thing. Now, on the other hand, you know, as you say, you could be wasting a lot of time doing what I'm saying and I freely admit that. But I would say that yes, you know, go for it. Go do your qualification and figure out who the decision maker, etc., etc., is.

Yes. And again, LinkedIn is your greatest weapon in this. But uh if if if you said, "Okay, guy, should you pitch too much or too little? Should you, you know, evangelize too much or too little?" I would say too much. Air on the side of doing too much. And this is completely in the face of the the concept of, you know, select a few targets, know them well, get get just the most highly qualified, specific, you know, use a rifle. I'm telling you, use a shotgun.

Yeah. I mean, this goes back to a lot of the things that we've been touting today, like expanding your luck, showing up, you know, getting practice, preparing, right? It's just all those things combined because you never know who you pitched to, what that will end up being or who they'll end up being in 20 years even.

Okay, I'll tell you a great story that you as a podcaster will truly appreciate. So, do you know who Angela Duckworth is?

Yes. MacArthur Award winner. grit, right? Okay, big deal. You know who among us as a podcaster would not want to have Angela Duckworth?

Nobody. Nobody. Nobody in their right mind. Maybe Joe Rogan wouldn't want, but anyway. So, so I want Angela Duckworth, right? So, I don't know her. So, I send an email to whatever info@angela duckworth.com. No response. Weeks go by and I and you know, I default to yes. I kind of say I like I really didn't know exactly what I was getting into today, but I default to yes. Right now, if you think that I did all the research and you had Marshall Goldmith and you know how many followers are, you're the most influential person on LinkedIn and all and that's why I said yes, you can believe that. God bless you. But that's not the truth. The truth is I default to yes. So I default to yes. and and one day I'm on this podcast as a guest and the person starts off by saying yeah so you know hi my name is whatever Trixie Smith and and I live in I don't know Mobile Alabama and I am a freshman in high school and so we're going to

talk about whatever innovation right and I was sitting there saying God you are such a dumbass like why did you accept to waste an hour of your life on a podcast with a 14-year-old person she probably has five subscribers to her podcast. Mom and dad, aunt, uncle, and younger brother. Okay, I'm sitting there thinking, "God, you are such a stupid," you know. Anyway, but lo and behold, man, she asks great questions.

It's so funny how sometimes you could get really surprised, I think. Yes, asked great questions. And then at the end of this podcast, I say to her, "Who else have you had on your podcast?" I'm thinking who else was dumb enough to say yes, right? And and she said, "Oh, about two weeks ago, I had Angela Duckworth." And my freaking jaw is on the ground, right? I said, "You had Angela Duckworth? How did you get Angela Duckworth?" She goes, "Well, Angela Duckworth really likes to help young women succeed." So I, as a young woman, reached out to her and she said, "Yes." I said, "Okay." I said, "So how about this? Will you ask Angela Duckworth to be on my podcast?" And she says, "Yes." So she, 14-year-old girl in, you know, like I said, Mobile, Alabama with Over the Moon podcast.

She writes to Angela Duckworth, CC's me, and lo and behold, Angela Duckworth answers and one thing leads to another and I get Angela Duckworth on my podcast.

Amazing. You know, people might think, "Oh, guy, everybody knows who you are. You're a big deal." Blah, blah, blah. So that's how you, you know, even Angela Duckworth would be thrilled to be on your podcast. You know, she's probably just checking info@angela duckworth.com every half an hour looking for that invite. But the truth is, it was a 14-year-old podcaster from Mobile, Alabama with five subscribers who got me on who got me Angela Duckworth. Now, that every entrepreneur should listen to that story and say, "Huh?" Now, what's the point?

The point is, you never know. You never know. You got to milk all those connections. No matter who they are, everyone is connected to someone

for all you know. You know, for all you know, her her grandfather was Warren Buffett, right? Who knows, right?

Exactly. Well, that's cool. I want to find out her name and and help her. I want to be like Angela Duckworth and help this girl.

That's right. All right. So, let's talk about enchantment before we go. I know we're wrapping up on time here, but I love this concept of like likability, first impressions, and and you know, making people like you more. So, I'd love to hear your best advice and guidance when it comes to being more enchanting.

Okay. So, enchantment, I think, has several pillars. One is likability because it's hard to be enchanted by someone you don't like. Let's face it, right? So, there's likability. Um, there's also sort of competence that it's hard to like people who are incompetent. Bozos, that's the second leg. And the third thing is trustworthiness. Because you could like somebody, you could like, I don't know, you know, some Tik Tok influencer, that doesn't mean you trust that Tik Tok influencer. You know, you could you could like Paris Hilton, that doesn't mean you trust Paris Hilton. So, likability, trustworthy, and competence.

Those are the three pillars of enchantment. And so, this book, Enchantment, is about how to increase all three of those things. As far as likability, I think a lot of it is just well, this was written before the pandemic, right? So, I think a lot of likability is, you know, what is your handshake like? You know, is it is is it like wimpy or or are you trying to crush the person's hand or is it in the middle? Um what is your smile like? Is it a grit your teeth, hold the pencil in your teeth kind of smile or is it a legitimate happy duchen smile? Are you showing crows feet? you're too young to have crows feet hollow. But you know it, are you showing your crows feet or not?

Cuz crows feet is a very good indication of sincerity and smiling. So it's those kinds of things. And a third thing in likability is are you accepting people for what they are or are you trying to change them? Right? And and so I think people can pick up when you you know you like you can sense that this person thinks that you know I should be a Democrat or I should be a Republican or you know I I should be something that I'm not. And it's hard to like people who don't accept you for what you are.

And I know that you say you also should be aligned to a good cause. And I thought this was really interesting because you wrote the book in 2011 and in the last year I feel like every other conversation I have is like conscious business, conscious leadership, right? Like everybody wants to talk about aligning purpose with a good cause. And it seems more recent because I've been doing this for four or five years and now everyone's talking about that. So I'd love to hear your thoughts on why you think we should align ourselves to a good cause. And you've obviously thought this for a long time. Well, ju just to be clear, I I'm not saying you should align yourself with a good cause because it's good marketing and good financial returns and good all and that although those may be true, don't get me wrong, but but I think yeah, it is a byproduct and I I just believe that there is a karmic scoreboard in the sky

and this karmic scoreboard is tallying what you do with your life and if you jack people around and screw them and you you know you like trash the earth and all that it's it's being counted someplace. Now you can say guy you're so full of you know like you do you have any scientific proof of this karmic school board? Not at all. You know you can't prove God either. But you know I I digress. But I'm just saying, you know, with something like this, why take a chance? Like, right, why take a chance? I mean, you're only talking about your life, your reputation, and who knows, maybe your afterlife. So, you know, do you want to be stuck in a 737 in a center seat in the smoking section, or you want to be in Singapore Airlines or, you know, Emirates a bus, Airbus A380? It's up to you. So, I I just think it's good karma.

Yeah. And I love I love your, you know, default. Yes. I'm the same way. I just say yes. If you can help somebody, if you have the time, why not, right?

Even if you don't have the time. Yeah. Well, this has been such a great conversation, guy. I always end my interviews with the same couple of questions and then we do some fun stuff at the end of the year. So, the first one is, "What is a piece of actionable advice that my young and profits can do today to become more profiting tomorrow?" you can learn how to truly empathize. That is um this is this goes beyond market research, you know. So market research is basically go and see go see how people live. Go whatever. I would say if you want to do it even better, you go and be which means you go and be the person like you, let's say you're doing a study of customer service. So, you could go to the customer service center and you could see what happens on the call lines. Or you could actually put the headset on and be the customer service person. Or you could actually call into your company's customer

service and be the customer. Empathy is a great skill and it'll just open your eyes to so many things.

Oh my gosh, I love that advice. And what is your secret to profiting in life? And this doesn't have to be monetary. Profiting is whatever you believe it is.

Listen to your wife. How's that? Why? Cuz women are smarter than men. I truly I truly do believe that. Like if you look at this world right now, men have screwed this world up from top to bottom for centuries. I think we should let women run the world.

I mean, what a better place to stop the interview right then and there. And where can our listeners go to learn more about you and everything that you do?

Well, if you truly want to see my best work, go to remarkablepeople.com. And just just a word of caution here, remarkable people is not guy spouting off about how to be remarkable. Remarkable people is guy getting people like Jane Goodall and Steve Waznjak and Neil Degrass Tyson and Ariana Huffington and Christy Yamaguchi and I could just go on and Angela Duckworth on and on. I'm I'm trying to get the wisdom from them into you. That's what I'm doing on Remarkable People.

I love it. Well, if you guys like my podcast, I think you're going to love, guys. So, make sure you check it out. We'll stick all of his links in the show notes. And thank you so much for this amazing conversation.

My pleasure. And uh maybe I should have you on the podcast. I really I would love to be on the podcast. They call me the podcast princess. I built a media empire. I have 60 employees. Started it as a side hustle. I'd love to be on your podcast.

I think you're the podcast queen. Forget the princess though. Thank you. I feel like I say you're old.

No, I know. I feel like I want the princess for a few years and then I'll graduate to queen. Like

Okay. Okay. Alrighty. Thank you so much. All the best to you. Take care.

Questions about this episode

What is discussed in "Guy Kawasaki: Win Every Pitch Using These Timeless Sales Principles | Sales | YAPClassic"?

In order: 0:00 Tiffany, Young and Profiting Podcast; 5:00 Goldman Sachs; 30:00 Young and Profiting Podcast; 40:00 Clowner Perkins, Goldman Sachs, Guy Kawasaki, Sequoia.

What is mentioned in this Young and Profiting episode?

13 people, works and ideas are mentioned, including Apple Inc., Canva, Young and Profiting Podcast, Goldman Sachs, Tiffany, Guy Kawasaki. Each one on this page links to its own page with every episode that mentions it.

How long is "Guy Kawasaki: Win Every Pitch Using These Timeless Sales Principles | Sales | YAPClassic"?

The episode runs 58 min; the transcript is about 10,631 words in 112 timestamped sections.

More from Young and Profiting

About this transcript: the episode's spoken words as captioned on YouTube, split into timestamped sections. Reclip.Me locates every person, work and idea in the text, keeps the time it is first named, and quotes the words around it verbatim. Last updated January 24, 2026.