Jonathan: Hey, everyone, Jonathan Bailor back with another bonus Smarter Science of Slim Podcast. I’m always excited about our podcasts, you know that; but today is a special one because we’re here with a gentleman who I am as excited to hear from as I know you are.
He is a man who has inspired me for literally over a decade and has had immeasurable impact on my life, a man who is normally known for his work in the technology and innovation world, but really is just an agent of change, is an agent of influence, and is an enchanting man. That is the title of one of his most recent books and the book I’d love to focus on today, which is called Enchantment. Guy Kawasaki, welcome to the show.
Guy: Thank you. Thank you very much for having me and that kind introduction.
Jonathan: Well, Guy, I wanted to just get started. Before we dig into the meat of today’s chat, I heard you speak probably a decade ago. If I remember correctly – it was so long ago – you told a story where you referred to yourself as a bozo, and I think it was in reference to your early goings-on with Yahoo. Would you mind just sharing that story really quick? I remembered it for decades, so I figured listeners would like it as well.
Guy: What happened was I was invited to interview for the CEO position of Yahoo, and at the time, who knew what Yahoo would become. So I turned it down. Lo and behold, boy, I wish I had taken that interview. Yahoo has had some challenging times lately, but it had quite a ride; and who’s to say it’s over yet? It could still have quite another ride. So I never should have – I should have said yes.
Jonathan: Do you recall why you said no to the opportunity?
Guy: Because it was so far away, and I have to drive so much, and who knew? It was not a very defensible looking site. It was just a collection of these two guys’ favorite websites. So who knew? Who knew?
Jonathan: That’s funny. Well, you’ve certainly picked up the pieces and built something quite lovely in Yahoo’s stead. The thing I wanted to focus on today is one of your more recent books; certainly you’ve written, I believe, somewhere around ten and done all kinds of other entrepreneurial things. Your book is called Enchantment, and the reason I wanted to bring you on this show, which tends to be a little bit more health-focused, is I’ve got to tell you, when you look at the economic pressures, when you look at the emotional pressures that our country is facing from a health perspective, I personally believe that it is an area in dire need of enchantment. Can you tell us a bit about what you mean by enchantment, the characteristics, and then maybe we can riff on how it could help save some lives.
Guy: For me, “enchantment” is to build a basis of a relationship on trustworthiness, likeability, and competence. I believe if we have those three, everything else is easy. I hope people would stop trying to just “sell” people; that they develop a likeable relationship, a trustworthy relationship and, above all, that they’re competent. Because I’ve found that it is much easier to enchant people when you are competent and you have great stuff than when you have a piece of crap. Trust me, I learned the hard way on that.
Jonathan: Please correct me if I’m wrong, there is a difference between getting someone to do what you want, like forcibly taking your child upstairs and throwing them in the room and saying, “Clean your room!” versus enchanting them, which is bringing about, as you call it, voluntary, enduring and delightful change.
Guy: Yes. That’s because deep down inside of everybody who’s enchanting, you have learned to accept others for what they are. You respect them for their own choices. You’re not trying to bludgeon them into anything. You want to show them perhaps a better way and hope that they accept it.
Jonathan: Guy, as you historically have done, you are able to crystallize things which are otherwise ephemeral. I think oftentimes what you describe as enchanting, you’ve distilled down in the book, is what a lot of people call the X-Factor or charisma; but you’ve really done a better job defining it. Have you seen people draw those kinds of parallels?
Guy: I guess so. I really don’t like to use the term “charisma” because I think many people believe that charisma is something you’re born with. To me, it has two negative effects. First of all is you think you have charisma, so therefore you’re born with it, it was a gift, you can’t lose it, you’re like some special person and there’s expectations of whatever, right?
That’s one problem where if you think you were born with it, if you have this feeling of entitlement because you’re charismatic, I think that’s a big mistake. The other flip side of that is if you think you’re not born with it, therefore you cannot achieve it, that is also bad. I don’t like to use the word “charisma” because it implies some special, lucky person who was born with it and doesn’t have to do anything else.
Jonathan: I love that distinction, Guy, because it puts the power in our hands. Where I want to take the conversation next is further talking about putting the power in our hands. Folks that are familiar with you know that your experience is in high-end technology very often.
A lot of the people listening to this show might say, “Okay, that’s great, I don’t live in Silicon Valley, I’m not in a position to start a new company.” I believe, based on what you say in your book, when enchantment is needed, that – let me just run through the list really quickly. When you want lofty, idealistic results; when the change is very difficult; when you need to overcome entrenched habits; when you want to separate from the crowd; and when you want to proceed despite delayed or non-existent feedback, literally, we’re five-for-five when you talk about making lifestyle changes, just general lifestyle changes in our everyday life. We need to enchant ourselves, almost.
Guy: Yes, I agree with that, absolutely.
Jonathan: Let’s just go through the list. Often, we see these lofty, idyllic results. We live in a world where nearly 70 percent of us are overweight, and there’s a 100,000-percent higher rate of diabetes than there was about 100 years ago. We want to avoid that; we’ve got this lofty result.
Guy: I just want you to know I just ate a piece of chocolate, but that’s okay.
Jonathan: You’ll notice in that list that perfection was not…it’s all good, it’s all good.
Guy: Okay. Well, the key here is that it takes several things. One is that you are cognizant of the existence of lofty ideals; and secondly, that you believe that you can achieve these lofty ideals; and arguably third, if you don’t fulfill those lofty ideals, you don’t go into a deep funk the other way and really tank yourself. All three, I think, are necessary. I’m in the middle of a weight-loss program right now, so I can relate to this.
Jonathan: The thing that really struck me, Guy – and this is what strikes me about all of your work. You strike me as a very principle-centered man and a man who is very much in favor of meaning and creating meaning. When you said in your book Enchantment lofty, idealistic results, what that made me think about is, for example, here is a non-lofty idealistic result.
Just make the scale have a lower number. That’s much different than set an example for my children so that they don’t get sick when they get older. To me, that’s a loftier… what do you think? Am I misunderstanding?
Guy: No, I think that is absolutely true, that setting an example for your children and your spouse – now that you put it that way, I’m even worse off than…
Jonathan: Well, the other thing I wanted to talk to you about is my experience at Microsoft. Certainly, you’re much deeper experienced in other technology arenas. We see brilliant people, I’m talking brilliant geniuses who, when it comes to doing these somewhat simple tasks regarding eating and exercise, it’s like a different language almost. So, what’s going on there?
Guy: Maybe they are all Rain Man when it comes to fitness and health. I don’t know. You see seemingly very intelligent people about some stuff just clueless about others. I can relate to that. You could accuse me of that, in fact.
Jonathan: Well, you seem to be doing just fine. Let’s go to the second, when enchantment is needed, when change is difficult or infrequent. Certainly, this is difficult here. It might be frequent, it’s certainly frequent when we have decisions about physical activity and what we put in our mouths, but it’s certainly difficult. How can we overcome difficult change?
Guy: First of all, difficult change is difficult for everybody, including myself, okay? So I don’t want people to think, “Oh, yeah, Guy has got this figured out.” I’ll tell you a story. I am in the middle of a program called Retrofit. What it does is, it’s very, very tech. So I have a FitBit Flex and I have a Withing or Worthing or Woving scale, a wi-fi scale or something, right? Every morning, I step on that scale, it calculates my weight, calculates my BMI, sends it to not only my website but also my counselor’s website or counselor’s analytics panel. There’s a counseling team of nutritionists, physiologists, and overall account manager. I’m supposed to record all my meals every day. This is an interesting thing. For this program, you don’t have to say, “Well, I had one cup of rice, eight ounces of chocolate, 16 ounces of beer, ten ounces of shrimp.”
They just tell you to list what you eat, not any quantities, not counting calories per se. I think, “There’s got to be an easier way.” Now, I just take a picture of every meal and I send it to them. I tell you, just the fact that I have to take a picture or report in, I just eat less because I say, “Oh, man, I got to admit that I just had red velvet cake.” It’s just easier not to take the picture.
This is an illustrative example, because the fact that I’m measuring daily with a scale is an influence; and the thought that they would come in to my panel and say, “Guy, you’re gaining weight now,” the fact that I can see a graph, the positive results reinforce more positive results, right?
The more you lose, the more you think it works, the more you’ll lose. Not that I have any fear of withering away to anorexia. So that’s another effect. Interesting thing: The nutritionist told me to start using a nine-inch plate. With a nine-inch plate, she said roughly half of that should be fruit and vegetable. So a nine-inch plate, half of that fruit and vegetables, I feel like a freaking rabbit these days.
I’m trying to communicate this feedback. There’s this guilt that other people are going to see, like you’re disappointing them. The hassle factor: The more you eat, the more you have to list, the more you have to photograph, the more you have to explain. It’s just easier to lose the weight than… Maybe this is completely contrary to everything you believe about weight loss, but that’s what I’m in the middle of right now.
Jonathan: It sounds like they’ve made it such a pain in the butt for you not to change that change is just the easier path at this point.
Guy: Well, I’m sure that they don’t position themselves as, “We’re the people making it a pain the butt to lose weight.” I think a lot of it is just social psychology, that whatever gets measured gets changed. There’s this social factor that when other people know exactly what you’re eating, it makes you hesitate to eat crap. There’s a lot of interesting stuff going on.
Jonathan: Absolutely. A lot of people, a lower-tech approach, but what you’re mentioning here, I’ve noticed a lot of people are using either Twitter or Facebook and they just photograph before they eat anything and just immediately post it up on wall. And they have found that to be extremely helpful in that social accountability, absolutely.
Guy: I think most people who do that are trying to show off that they’re eating a steak. I don’t think it’s because they want people to eat less. If anything, it might be encouraging people to eat more and drink more just to show off that you had that steak, right?
Jonathan: Well, certainly. And certainly we could talk about whether or not eating less, if you’re eating the right kinds of foods, is the key; but that’s neither here nor there, we can get to that later. Guy, what we’re talking about here has to do very much with the third area when enchantment is needed, and that’s overcoming deeply-entrenched habits.
Just for a second, I want to maybe pop out of using you as a personal example. We see so much the need for overcoming entrenched habits in technology and in other areas of life, but certainly in our lifestyle. Is there a level of this voluntary, enduring, delightful change, is there this trustworthiness we could build within ourselves; is there meaning we could apply that could make it easier for us to overcome entrenched habits?
Guy: Wow, I never thought of it that way. I’m sure there could be, absolutely. To wrap my mind around that…
Jonathan: Well, Guy, the reason I bring it up, oftentimes people who are in the health and fitness arena – you have a technology influence or engineer background. I’m also an engineer by trade. When you look at a problem space, you don’t have to look at just traditional engineering problems like an engineer. You can say, for example, can we apply the same principles we apply to institutional change or organizational change and change our lifestyle habits that way.
When you do that, when you apply that model, sometimes it’s pretty interesting, especially if you’re doing that in an industry which historically is more about deferring to authority and maybe just doing what we did in the past out of respect; whereas in technology, the exact opposite is true. It’s always about, like, the past is almost innately bad and we need to make improvements in it. It’s certainly interesting to apply those models’ cross-discipline.
Guy: Yes. I think, forget the weight loss, a very good principle in life is to look outside. If you’re in the tech business, there’s a lot you could learn by going to something that’s nothing to do with tech, that you see this cross-realization of ideas. You get inspired by these different things. I’ve noticed that a lot in my career, that I go to these things that have nothing to do with my business and I say, “Oh, that is a really great idea. How can I rip that idea off and use it?” One of the key tests is you got to know what to rip off. You could break into somebody’s house and steal all the garbage; you need to know what to steal.
Jonathan: Exactly! I love that. Certainly we don’t want to break into anyone’s house and steal their garbage. If we’re going to break into their house, we want to get some good stuff, right?
Guy: Yes, yes.
Jonathan: I think someone defined “creativity” once as just the ability to combine two unrelated things in a sensible fashion on some level. Number four when we need enchantment, which is just – I’m so attracted to this idea of enchantment because I think, especially in the area of lifestyle change, we try to brute force.
It’s just, “I’m going to force myself to eat less, I’m going to force myself to exercise more,” and we wonder why it doesn’t work. That sort of approach doesn’t work in any area of life. So when we talk about overcoming entrenched habits, we talk about separating from the crowd. Certainly that is applicable here, because the crowd is just saying – and it sounds like you might be experiencing this as well right now – just eat less and exercise more, just eat less and exercise more, that’s it. That’s what the crowd is saying, but it doesn’t seem to be working. What can we do to separate from the crowd?
Guy: Well, why don’t you tell me? Because that’s what I’m trying to do, eat less and exercise more. You’re shaking me all up here.
Jonathan: I certainly don’t want to shake you up too much. The question I would ask you, Guy – and I don’t want to put you on the spot here – is certainly if one’s goal, for example, is to stop burning their hand on the stove, the answer is not to just touch the hot stove less, it’s to put your hand somewhere else. I think often, when we say to take the same diet that caused us to be dissatisfied, either with the way we feel or the way we look, and just eat less of it, is not the correct approach or the ideal approach.
The ideal approach would be more find the types of foods that have been proven to enable us to reach our specific goals and eat as many of those as you want because, I’ve got to tell you, Guy, when you eat the right kind of food, the body reacts appropriately, and it is nearly impossible to overeat them.
Guy: Yeah? Tell me what kind of food that is, because I want to go to the market tonight.
Jonathan: It’s really pretty simple, Guy, it’s three categories. The first is going to be non-starchy vegetables. These are vegetables you could eat raw. You don’t have to eat them raw, but think of vegetables you could eat raw. For example, you can’t eat a potato raw, but you can eat things you put in salad raw. So that’s going to be the vast majority of the food you put into your mouth.
Nutrient-dense protein: Seafood, high-quality cuts of meat, eggs, things like low-sugar dairy, maybe like a cottage cheese or a Greek yogurt, things that are high in protein and low in sugar. Then next is going to be whole-food fats, so think coconut, cocoa, avocado, nuts and seeds. And then also, low-fructose fruits, so berries and citrus fruits.
Guy: Does that eliminate bananas? Are bananas a good or bad thing?
Jonathan: In terms of relative to a Snickers bar, banana is good. In terms of relative to some other fruits, not going to be as good. Guy, I don’t know, maybe the next thing you’re trying to do is be on the cover of a fitness magazine. Bananas would be okay for you as long as that’s not your goal.
Guy: No, no, that’s not my goal, not unless I’m the “before” picture. We’re kind of going off on a tangent here, but I’m so intrigued. Are you thumbs-up or thumbs-down on coconut water?
Jonathan: I’m extremely thumbs up on coconut, the whole food. I’m not a huge fan of drinking calories in general. I would encourage you, maybe, Guy, if you want, is to make your own coconut water. It’ll save you some money, too. Just get shredded, unsweetened coconut; you can get it off Amazon, it’s organic and super easy, you can get it at a local market. You live in California, you could probably get it if you walk three steps in any direction.
Guy: Shredded, unsweetened coconut. So it’s the meat?
Jonathan: It’s the meat. And just pop it in a blender. Hopefully you have a nice blender. Blend it up for a minute with some water, throw some ice in there to cool it down, you’ve got yourself some coconut water.
Guy: Is that less calories than the coconut water I’m paying four dollars a bottle for?
Jonathan: Oh, man, we might have to set up a little session for you here because, my friend, it’s not about the calories, in fact. We’re not just trying to eliminate calories, we’re trying to provide your body with the highest-quality calories. When you eat that whole coconut, you’re going to get a bunch of amazing nutrients and, actually, fat called medium-chain triglyceride, which helps your body burn fat, and you’re going to get a bunch of fiber so it’s going to help fill you up.
It’s less like drinking a soda, where you notice you can drink 600 calories of soda and it doesn’t do anything to satisfy you; whereas if you ate 600 calories worth of vegetables, your stomach would explode. I like whole foods. Coconut water is not bad, but I would much rather you eat a whole coconut, not literally the entire nut, but you understand my point.
Guy: See, the way I look at it, it depends on where you’re coming from, but I think that coconut water is so much better than drinking a Coke.
Jonathan: Oh, absolutely!
Guy: At least I think I’m moving in the right direction.
Jonathan: Oh, and to be clear, Guy, do not hear me saying that what you’re doing is wrong. Maybe I’m just suggesting you can have something even less expensive that’s even better for you in place of that Coke which is still delicious, and that’s your home-made coconut water.
Guy: Okay. You are saying this is shredded coconut. Is it dried?
Jonathan: Yes, at least the kind I get, because I just order it in bulk off Amazon.
Guy: So it’s like flakes?
Jonathan: Yeah, think of it… I mean, have you ever tried dried fruit before, the chips?
Jonathan: It’s essentially just the coconut meat and it’s just dry, yes.
Guy: I’m going to go to Whole Foods tonight and look for that.
Jonathan: Yes, certainly things like coconut water are going to be better for you than Coca-Cola. The closer you can get to something found directly in nature, there’s a good rule of thumb, the better it’s going to be good for you. Folks, welcome to the… Guy, we should just do this. You want to talk about public accountability, we should have a weekly podcast with you where we talk through this stuff.
Guy: Why don’t I just give you the password to my scale and you could just…
Jonathan: Guy, I tell you, if I had my druthers, we would take that scale out in your backyard and we’d break it with a baseball bat.
Jonathan: Because it is not indicative of your health, it is not indicative of your fitness. What I would have you do is replace that $99-plus scale with a 99-cent measuring tape.
Guy: To measure what?
Jonathan: Your waist circumference.
Jonathan: Much, much better predictor of long-term health, much better predictor of long-term illness risk, and also so much better predictor of aesthetics. People could weigh – if I told you I weigh 200 pounds, does that mean I’m overweight? Who knows? It’s what the 200 pounds is made out of, right? So that waist measurement is really, really key. You’ve got to separate from the crowd, Guy. Come on, enchant yourself.
Guy: I am separated from the crowd. Most people don’t do what I do.
Jonathan: I’m just kidding. Guy is like, “I’m never coming back on your podcast, ever!”
Guy: No, I don’t care. This is learning, this is enchanting! Usually, when I do these kind of interviews, it’s all one-sided; I’m passing all the knowledge I can. So today I learned something in this interview. It’s very unusual.
Jonathan: Well, thank you, Guy. Let’s move on to the last stage of when enchantment is needed because certainly, it applies here. And maybe you even have some personal experience with this, I know I do, and that’s to proceed despite delayed or non-existent feedback.
Guy: Yes. It’s very important because… well, I don’t want to go back to weight. It is kind of self-driven at some level. Thinking back on a business example, there were years when we didn’t get a lot of positive feedback about Macintosh and Apple. Those were challenging days. Becoming enchanting is not easy, it’s not get rich quick, it’s not fix everything quick. You know, there would be more enchanting people if it were easy. There would be more skinny people if it were easy too, right?
Jonathan: Guy, there’s continually, both in technology and in wellness, there’s always these get rich quick, quick fix, it’s just simple and it’s just so easy. How do we enable ourselves to proceed despite delayed or non-existent feedback?
Guy: Partially, the realization is that it is a challenge and you’re going to have to gut it out and it’s not easy. I think some of these gimmicks, well, not gimmicks, I think it’s real that when you see yourself making progress, you make more progress. It becomes a positive loop. I think it’s a very important principle.
But I never thought about that. So these principles of whatever gets measured is what you do, and results beget results. And if you get negative results, you get even more negative results, or you give up. There are these things that really, I think, impact people’s behavior, I really do.
Jonathan: Guy… Oh, go ahead, sorry.
Guy: No, you go ahead.
Jonathan: To the point of that which is measured is so important, what do you think – because there’s certainly business and lifestyle behavior here. For example, in the health arena, if you were to measure your weight, say you’re a woman and your weight fluctuates dramatically based on the time of the month it is; or you’re a man and you’re very stressed and retaining water. What you’re measuring could actually deter you from moving forward, even though you might be doing all the right actions. Do you have any thoughts, even maybe for sales, like you’re making great sales calls, you’re putting in great work, it’s just no one is picking it up yet. Do you want to measure the actions you’re taking? Do you see what I’m saying?
Jonathan: It’s a difference between measuring your effort and if you’re doing consistent, correct effort versus measuring something you may not be able to control as much.
Guy: This is the hardest question in the world. Entrepreneurs ask me this all the time. It’s like, “When do you know if it’s time to give up?” That is the hardest question in the world. Because you always hear these stories about people who didn’t give up and they refused to give up and they succeeded and all that. But you never hear of the 99 percent of the people who gave up and were right to give up.
So what do you do? I don’t know if there’s an easy answer for that. Well, one easy answer only will help men, is you ask your wife. I think your wife has much better judgment than you. If you’re a woman, I don’t know who you ask. Well, you could have same-sex marriages, so you could still ask your wife.
Jonathan: There you go.
Guy: I don’t know, that’s a hard one. Really, lots of entrepreneurs ask me that. I wish I could say it’s as simple as, “Well, if you’re asking the question, you know it’s over.” But that’s not true. Every good entrepreneur is a little bit paranoid, and a good entrepreneur is always worried, “Are you doing the right thing, am I doing the right thing, should I be doing something else?” Everybody thinks like that. and if somebody tells you that they’re totally certain they’re doing the right thing, they’re full of shit, basically.
Jonathan: Absolutely. Again, folks, to the listeners, when Guy says “entrepreneur,” I interpret “entrepreneur” as broadly as possible, where that’s someone who’s trying to start something new. And again, that same thing applies to us.
Guy, you mentioned right now you’re doing a bit of a health effort. When would you stop, if things weren’t going the way you would want them to?
Guy: When my wife tells me.
Jonathan: I might have to have a podcast with your wife, then.
Guy: Yeah, you would learn a lot more.
Jonathan: Guy, I love it. Certainly, I could talk to you for hours and hours and hours, but I know you’re a busy man, so I was just hoping we could wrap up this conversation with a quick summary of, again, from your mouth, what it means to be enchanting, why it matters, and steps we could take to be enchanting. And then I have one last question for you.
Guy: Okay. So basically, I think the key to enchantment is a set of three things, which is likeability, that people like to be with you, look forward to seeing you. That they trust you; I mean, you can like somebody but not trust them. You could like Charlie Sheen, like to hang out with Charlie Sheen, but you don’t trust Charlie Sheen. That’s trustworthiness. Think of examples, like where women buy shoes without trying them on.
And then there’s the competence-quality check mark. Think of Apple with the great stuff they make. So if you are competent, and you have a likeable and trustworthy personality, I think you’d be able to influence people’s minds and hearts and actions.
Jonathan: Guy, the question that I want to pose back to you – and maybe this isn’t something that I necessarily want you to answer on this show, but I think it might be something interesting to think about, because it’s kept me up at night for the past couple of days. If we want to drive change in our self, do we need to like our self; do we need to trust our self; and do we need to believe that we are competent in order to enchant and make change in our own lives?
Guy: It’s kind of hard to imagine those not being necessary. It’s also hard to imagine how you fabricate an experiment where you find – okay, you need to find a group of people who don’t trust themselves and see if they achieve anything. It’s hard to do a scientific experiment that way, right?
Guy: Yes, I think those are necessary conditions because you are trying to effectuate change, and change is not easy, believe me.
Jonathan: Well, Guy, I want to know one last thing, and that’s what’s next for you? Your CV is so long, it made my computer crash. So what are you adding to it next?
Guy: I am an adviser to the CEO of Motorola, I do a lot of work in Motorola; I have just written this book APE about self-publishing, how to self-publish a book; and I do a lot of writing and speaking. And I have four children, so I am a busy boy.
Jonathan: I love it! You’re living a healthy lifestyle, it sounds like, so that’s even better.
Guy: Healthier! Coconut water, not Coke.
Jonathan: You know what, it’s all about taking steps in the right direction. It sounds like that’s what you’re doing.
Guy: That’s right.
Jonathan: Well Guy, thank you so much for joining us. And on a personal note, thank you so much for all that you’ve taught me over the decade-plus that you have.
Guy: This has been a lot of fun. Thank you very much.
Jonathan: Thank you. And listeners, I hope you enjoyed today’s show as much as I did. If you want to learn more about Guy, just type his name into any search engine and you’ll be like, bam, there’s so much stuff. Guy Kawasaki, website of the same name. Enchantment is the book we talked about today. The newer book is called APE. He’s got a Wikipedia entry. He’s the man.
I hope you enjoyed today’s show and remember, this week and every week after, eat smarter, exercise smarter, and live better. Talk with you soon.
This week we have the pleasure of hearing from Guy Kawasaki. In his own words:
“Guy Kawasaki is a special advisor to the Motorola business unit of Google. He is also the author of APE, What the Plus!, Enchantment, and nine other books. Previously, he was the chief evangelist of Apple. Kawasaki has a BA from Stanford University and an MBA from UCLA as well as an honorary doctorate from Babson College.
I was born in Honolulu, Hawaii in 1954. My family lived in a tough part of Honolulu called Kalihi Valley. We weren’t rich, but I never felt poor-because my mother and father made many sacrifices for my sister and me. My mother was a housewife, and my father was a fireman, real estate broker, state senator, and government official during his long, distinguished career.
I attended Iolani School where I graduated in 1972. Iolani is not as well known as its rival,Punahou because no presidents of the U. S. went there, but I got a fantastic and formative education there. (Punahou is “USC,” and Iolani is “Stanford”—but I digress.) I pay special tribute to Harold Keables, my AP English teacher. He taught me that the key to writing is editing. No one in the universe would be more shocked that I have written ten books (or one book ten times) than Harold Keables.
After Iolani, I matriculated to Stanford; I graduated in 1976 with a major in psychology—which was the easiest major I could find. I loved Stanford. I sometimes wish I could go back in time to my undergraduate days “on the farm.”
After Stanford, I attended the law school at U.C. Davis because, like all Asian-American parents, my folks wanted me to be a “doctor, lawyer, or dentist.” I only lasted one week because I couldn’t deal with the law school teachers telling me that I was crap and that they were going to remake me.
The following year I entered the MBA program at UCLA. I liked this curriculum much better. While there, I worked for a fine-jewelry manufacturer called Nova Stylings; hence, my first real job was literally counting diamonds. From Nova, its CEO Marty Gruber, and my Jewish colleagues in the jewelry business, I learned how to sell, and this skill was vital to my entire career.
I remained at Nova for a few years until the Apple II removed the scales from my eyes. Then I went to work for an educational software company called EduWare Services. However, Peachtree Software acquired the company and wanted me to move to Atlanta. “I don’t think so.” I can’t live in a city where people call sushi “bait.”
Luckily, my Stanford roommate, Mike Boich, got me a job at Apple; for giving me my chance at Apple, I owe Mike a great debt. When I saw what a Macintosh could do, the clouds parted and the angels started singing. For four years I evangelized Macintosh to software and hardware developers and led the charge against world-wide domination by IBM. I also met my wife Beth at Apple during this timeframe—Apple has been very good to me.
Around 1987, my job at Apple was done. Macintosh had plenty of software by then, so I left to start a Macintosh database company called ACIUS. It published a product called 4th Dimension. To this day, 4th Dimension remains a great database.
I ran ACIUS for two years and then left to pursue my bliss of writing, speaking, and consulting. I’ve written for Macuser, Macworld, and Forbes. I call these the “Wonder Years” as in “I wonder how I came to deserve such a good life.”
In 1989, I started another software company called Fog City Software with three of the best co-founders in the world: Will Mayall, Kathryn Henkens, and Jud Spencer. We created an email product called Emailer which we sold to Claris and then a list server product called LetterRip.
In 1995 I returned to Apple as an Apple fellow. At the time, according to the pundits, Apple was supposed to die. (Apple should have died about ten times in the past twenty years according to the pundits.) My job on this tour of duty was to maintain and rejuvenate the Macintosh cult.
A couple years later, I left Apple to start an angel investor matchmaking service calledGarage.com with Craig Johnson of Venture Law Group and Rich Karlgaard of Forbes. Version 2.0 of Garage.com was an investment bank for helping entrepreneurs raise money from venture capitalists. Today, version 3.0 of Garage.com is called Garage Technology Ventures; it is a venture capital firm and makes direct investments in early-stage technology companies.
Currently, I’m a founding partner at Garage and co-founder of Alltop as well as a husband, father, author, speaker, and hockey addict. Alltop is an online magazine rack that I hope you’ll check out—you’ll probably enjoy Innovation.alltop, for example. I’ve also written ten books. My latest is Enchantment: The Art of Changing Hearts, Minds, and Actions.”