10 Start Up Secrets You Don't Have to Learn the Hard Way
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The Insider’s Guide to Startup Success: 10 Must-Know Secrets

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Ever heard the saying, “Learn from the mistakes of others. You can't live long enough to make them all yourself?” Well, when it comes to startups, this couldn't be truer. Luckily, Guy Kawasaki, the author of “The Art of the Start 2.0,” has got your back. I sat down with him to uncover ten startup secrets that can save you from learning the hard way. If you're ready to give your startup the best shot at success, you won't want to miss this.

The Art of the Start 2.0 is the quintessential guide for anyone starting anything written by Guy Kawasaki. I had a recent one-on-one interview with Guy to talk about The Art of the Start for My Book Club and got some great takeaways that you can use to help with your business or entrepreneurial success.

Genuine influence goes deeper than getting people to do what you want them to do. @GuyKawasaki Share on X

Here are ten start-up secrets for you:

  1. Create an individual pitch email for people that you want to connect with. Don't cut and paste.
  2. The subject line of your email determines whether your email is read or trashed.
  3. Send a short email with four to five lines.
  4. Don't send an email to ask if you can ask a question. You can blow your one shot.
  5. If you try to take advantage of people, they'll know. And remember.
  6. Three classes that students should take if they want to be an entrepreneur: writing, programming, and debating or presenting.
  7. It's not about you. Please do your research on people you're pitching to ensure it's relevant for them.
  8. Guy does check out cool things that are emailed in good pitches with links, and so do I. If you write a great email, it can get noticed.
  9. Have a YES attitude. The way Guy achieves networking success is to default to yes, which means that basically whenever he meets people, he's always thinking how can he help them. This is a yes attitude. Many people are thinking quite the opposite. They're thinking of how I can say no or how can I not be taken advantage of.
  10. Guy's perfect pitch deck: 10 slides, black background, white text, Sans-serif, bold font, 30 points or more, put in as many diagrams as you can and as little text as possible. You're better than 90% of the pitches in the world right there.

There are many ways to fail, but there are many ways to succeed, too.

And there you have it—ten startup secrets straight from the guru himself, Guy Kawasaki. Remember, the road to entrepreneurial success is fraught with challenges, but you don't have to navigate it blindly. With these invaluable tips, you're not just avoiding common pitfalls; you're setting yourself up for unparalleled success. So go ahead, take these secrets to heart, and let's make your startup the talk of the town. Your future self will be forever grateful.

Full transcript of my one-on-one interview with best-selling author and Silicon Valley tech advisor Guy Kawasaki about The Art of the Start 2.0.

Peg Fitzpatrick:         Hi, this is Peg Fitzpatrick with My Book Club, and I am here with my special guest from an Uber car, Mr. Guy Kawasaki. Hello!

Guy Kawasaki:          This is truly a Silicon Valley phenomenon. I'm in the back of an Uber Black car. I don't do Uber X, I think, you know. I'm traveling south on the 101. It's because I miscalculated what time I could get home.

Peg Fitzpatrick:         Because you had a big fancy schmancy board meeting with fancy tech people. I got it.

Guy Kawasaki:          Well, not really, not at all. I had a nice lunch with the communications person of Wikimedia because I'm on the board of trustees of Wikimedia.

Peg Fitzpatrick:         Very cool. Well, it's a nice throwback because our first book club, you actually tweeted in from a taxi like in New Jersey or something. I only remember that because it's all on the first book club thing that you were like, “I don't think I could make it. I'm traveling.” Then you were like, “Hey, I'm in a taxi. It's kind of like that, but now we're not in taxis, we're in Uber. Books must be selling well.

Guy Kawasaki:          You've come a long way. We've gone from just text and now we have video.

Peg Fitzpatrick:         Yeah, well back then Uber didn't exist either.

Guy Kawasaki:          That's when they were stagecoaches, right?

Peg Fitzpatrick:         Stagecoaches … 2011 when we started doing Book Club. Okay, so today we are going to talk about The Art of the Start 2.0, which is an updated version of Guy's classical entrepreneur guide The Art of the Start. It's much bigger and thicker than the original version, so there's a lot to talk about. If you don't know Guy Kawasaki, you clearly don't have a computer, but I'll give you a little background. He lives in Silicon Valley as he mentioned. He was the original Apple Evangelist, and he is now the chief evangelist of Canva, which is an online design tool.

You will make his life if you go check it out after this because that will make him happy, or happier because he was always happy. Let’s see, what else do I want to say? You were my co-author on a book. We worked together, and you’re like an awesome father. Let’s dig into questions about Art of the Start. Are you ready?

Guy Kawasaki:          Sure.

Peg Fitzpatrick:         Okay, so this is my first question. It's really not about Art of the Start, but I'm sneaking it in because this is my question I have for you. You have said that everything that you know about sales, you've learned from working in the jewelry business, and that is a skill that entrepreneurs, they have to be kind of like the jack of all trades, so what did you learn in the jewelry business that would help entrepreneur with pitching or selling their business?

Guy Kawasaki:          Yeah, so prior to going to work in high tech, I worked for a small, family-owned jewelry manufacturer in downtown LA, literally downtown LA. This is a company that got gold and loose diamonds and [inaudible 00:03:06] It was not a retail operations. This was a manufacturer. We sold to retailers. Let's just say the jewelry business is a very competitive business because at some level, you know, 18 karat gold is 18 karat gold or a VVS diamond is a VVS diamond, so it was all about trust, personal selling, hand to hand combat.

It's not like today where you have this freemium model, and you know, 20,000 people a day are signing up for your service and 2% are going to be paying you in the next 90 days and you never know who they are. Maybe you store their credit card, nothing at all like this. It's truly hand to hand combat, and I learned so much about selling that has been so useful for the rest of my career because at some level you're always selling and [inaudible 00:04:00] very important skill.

Fundamentally, in startups, you're either making it or selling it. That's the only two things that matter.

Peg Fitzpatrick:         Was your first boss then the person that you learned that from at the jewelry business?

Guy Kawasaki:          Yes, I really kind of, I broke the color boundary, the race boundary, you know a lot of things because this was a small, family-owned company … Jewish people, and I’m not exactly Jewish, so it is a Jewish industry. It was really interesting. I probably know more Yiddish than Japanese to this day.

Peg Fitzpatrick:         Was it sink or swim or did you get some guidance? Or was it just like go sell stuff, and if you don't, you know?

Guy Kawasaki:          It was closer to that. Not in the sense of we're going to fire your butt if you don't sell but I worked inside, so I worked with the salesman, but I also made sales calls for the company. I think one of the most-

Peg Fitzpatrick:         That's something that doesn't happen today either. Is it direct sales calls?

Guy Kawasaki:          Yeah, and so one thing you learn in direct sales is rejection, so you learn that you have to beg for an appointment, and the appointment starts late or it gets cancelled at the last minute, and you know, you do the whole thing and you negotiate the whole thing and then they cancel the order or you get all this done, and then you find out that the guy doesn't have the right credit, so you can't place the order. So many things could go wrong. I think that's a very valuable skill.

Today, again, you just say, all right, we got 10,000 new signups today, and we're going to monetize a hundred of them, and that's out business model. It's not like that in jewelry.

Peg Fitzpatrick:         No, yeah. Hand to hand, awesome. Okay, so now my burning question that I had has been answered I can move on. Okay, so this question comes from a millennial. Miss Shayla read your book and she would like to know what three classes you would recommend for college students who would like to start a startup. If they're in college, what would you recommend?

Guy Kawasaki:          If you were in college, I would, first of all, take at least one computer science programming class. Not necessarily because you're going to be a programmer, but at least so that you know when programmers are lying to you because sometimes it's hard to tell when they're lying. Sometimes they don't know they're lying. At least one engineering class. I would also take a class in writing. I would take a class, if such a thing exists, in debate or presenting or, you know, pitching.

Now, you could also … The flipside of this question is what classes are not necessary and I kind of think that things like accounting and all that, which everybody says you should know, are less necessary because those are positions that are easy to hire for. I would rather have an articulate person in writing and speaking, who either is a programmer or understands programming, than to have someone who's an expert in finance, accounting, and operations research. I think those are staff positions at startups, which is different than founder positions.

Peg Fitzpatrick:         Okay, cool. Networking is key to success in being an entrepreneur, so can you give some tips on how to connect and maintain a network because I know that's one of the things that you have a huge amazing network, so you clearly know how to do it.

Guy Kawasaki:          I think, the way I achieve success for this is I kind of default to yes, which means that basically whenever I meet people, I'm always thinking how can I help them. This is a yes attitude. Many people are thinking quite the opposite. They're thinking of how can I say no or how can I not be taken advantage of.

I think if you go through life like that, man, you're going to miss a lot. I think the upside of defaulting to yes far exceeds the downside of maybe being taken advantage of. I've never really been taken advantage of. You've been actually involved in some cases where people tried to take advantage of us, right?

Peg Fitzpatrick:         Yeah.

Guy Kawasaki:          They never got it. They never took advantage of us. We will never freaking help them again. We have a list.

Peg Fitzpatrick:         Now people know we have a list.

Guy Kawasaki:          There is default to yes and there's stupidity.

Peg Fitzpatrick:         Yeah. That's the truth. Let me ask you this, when you meet people that are on a level that you'd like to connect with, how do you stay connected with people? Through e-mail mostly?

Guy Kawasaki:          Yeah, it's mostly through e-mail. I can't tell you that I'm not really this warm and fuzzy, touchy feely person who's like … The thing I hate to do more than anything is meet in person.

Peg Fitzpatrick:         Yeah?

Guy Kawasaki:          Yeah, I hate to tell you. It's so inefficient. People send me e-mails and they want to have a cup of coffee.

In their mind they're asking me for a half an hour, but it's not true because most plans, it takes a half an hour to get there, and then it never really goes a half an hour, it always goes an hour, so now we're at an hour and a half, and then it takes them a half hour to get back, so that's two hours. Two hours in my work day after I drop off kids and play hockey, I really have about four to six hours that's left, so you're taking up half my day.

A quick cup of coffee at Starbucks to you is half my day to me. I know it sounds kind of arrogant and kind of like not defaulting to yes, but I would much rather you send me a five-sentence e-mail and I could just help you via e-mail, rather than you telling me your whole fricking life story and trying to be my buddy. I don't want any more buddies.

Peg Fitzpatrick:         I solve that by living in New Hampshire.

Guy Kawasaki:          Yeah, that's right.

Peg Fitzpatrick:         Actually, I had a guy today. He was very nice, but he tried to like pitch me in my Facebook messaging, which is like, to me, not the-

Guy Kawasaki:          Really?

Peg Fitzpatrick:         Right, that's what I was like, really? He was like, “I just wanted to say hi,” and I'm like, “Hi.” I had no idea who he was, and then he started with, “So I had a question I've been wanting to ask you for a long time. Can I ask it?” So that's kind of like, you just wasted a question, but okay, so I'm like, “Sure, shoot.” Then he starts with he really had something that he wanted to pitch me, but then he finished it with like, “and I wonder what your thoughts are on social media?” I'm like, “So, have you been waiting to pitch this to me, or did you want to know about social media?” He's like, “Oh, you're very direct.” I'm like, “Well, you know, if you want to pitch.” I didn't actually answer his questions, but I did give him some tips on if you want to connect with someone that you should send an e-mail pitch, not like a blind connection like that because he kind of [crosstalk 00:11:36].

Guy Kawasaki:          I would just point him to our book and say, “Here, you want to understand social media, read the book.”

Peg Fitzpatrick:         Right, right. That leads me to e-mail pitches, which you mentioned you like five-sentence e-mail pitches. I'll tell you a secret, I think I may have already told you this, but maybe other people don't know this. I actually … before I sent my first request to Book Club, I reread the section in Enchantment a whole bunch of times to make sure I met exactly what you like in an e-mail. I would spend forever making sure I had really good creative subject lines because that is really the key to getting an e-mail open.

Guy Kawasaki:          [inaudible 00:12:14].

Peg Fitzpatrick:         So I Guy Kawasaki'd my e-mail to Guy Kawasaki.

Guy Kawasaki:          Do you have it? You should save that.

Peg Fitzpatrick:         I did. It says, “Dear Mr. Kawasaki.” Isn't that funny? But I didn't know you, so you should be polite, right?

Guy Kawasaki:          Obviously, it worked. You should post that, and then everybody will copy and paste it, and I'll get the same thing thousands of times.

Peg Fitzpatrick:         Well, tell me what kind of e-mail pitches do you … I was asking you if you would be a guest on Book Club, so it was something that was really kind of beneficial to you, too, but it's a two-way street. You know, when people are asking you to be in a podcast or a hangout, it's kind of like they're asking you for time, which is valuable, so-

Guy Kawasaki:          Well, for me, it's all about the subject line because I probably have made up my mind just from the subject line, and it's really like the first three to five words. I tell people it's five sentences, but I make [inaudible 00:13:14] some absolute killers. If somebody starts off an e-mail to me with “As you probably know,” okay, so it's like, “As you probably know, social media is a hot topic.” I throw the e-mail away. I just like … you know, yeah, I probably do know social media is a hot topic. I probably do know that security is a hot topic. I probably do know that the world is round. I just … I just think it's an idiot that starts an e-mail with, “As you probably know,” because if you know I probably know, then why the hell are you telling me?

Another kind of killer introduction sentence for an e-mail is “My 22-year old client has created a 1 million dollar company and is writing a book, How to Succeed in Life.” I'm like, 22 years old, you don't know how to succeed in life, and I could give a shit that you started a 1 million dollar company, you know? Steve Jobs sent me that e-mail if … Elon Musk sent me that e-mail, okay, but you know, your 22 year old client, Joe Schmo, of Schmo Way whose Schmo Industries 1.5 million dollar Schmo business, I could care less. Now all these PR people are saying, “Oh, Guy is such an arrogant asshole. You know, all that.”

Peg Fitzpatrick:         The PR e-mails really are the worst, though. They're so canned. You know someone's paying a lot of money to have someone send that e-mail on their behalf.

Guy Kawasaki:          Well, the even funnier ones are like your book Rich Dad Poor Dad is one of my favorites. Oops, that's Kiyosaki, not Kawasaki.

Peg Fitzpatrick:         Yeah, do you respond to those at all, or do you just delete?

Guy Kawasaki:          I respond just to humiliate them. I say, “Well, you know, I'm Poor Dad, Poor Dad. I'm Kawasaki, not Kiyosaki. I know we all look alike and we all sound alike, but you got the wrong guy.”

Peg Fitzpatrick:         If somebody does have a great subject line and they have a really nice short, concise … You know, “I know you're very busy. I have this app I created. Here's a link to it. Tell me what you think.” Do you ever take the bait and click on those to see what they are?

Guy Kawasaki:          Oh, all the time.

Peg Fitzpatrick:         Yeah?

Guy Kawasaki:          All the time. Especially if it's like social media, right?

Peg Fitzpatrick:         Yeah.

Guy Kawasaki:          If it's something like I know you use Buffer, and Sprout, and Hootsuite, let me show you an alternative. I would look at that all day long, or I know you want to … I know you're into optimizing something, so here's a way, or something like that. I would do that all the time, but for this e-mail to work, they really got to know that I'm really, truly interested. If somebody says I know you're interested in Enterprise Software, then clearly that's a form e-mail because I have no interest in Enterprise Software at all.

Peg Fitzpatrick:         Right. Do your research on people that you're pitching to make sure it's relevant for them.

Guy Kawasaki:          Yeah, many people say Dear Gary, you know what I mean.

Peg Fitzpatrick:         Really?

Guy Kawasaki:          Yeah. Another way I make a really fast judgment is, when you're in Gmail, often you see the person's avatar, right?

Peg Fitzpatrick:         Uh-huh (affirmative).

Guy Kawasaki:          So if it's a dumbass avatar, I just make an instant decision. You know, only a dumbass would have a dumbass avatar. Why am I bothering with this e-mail? I also … when it comes from women, and they're in like some bikini or some cocktail dress, I got to tell you, I make the same judgment. I just say, you know-

Peg Fitzpatrick:         Not professional?

Guy Kawasaki:          Yeah, yeah.

Peg Fitzpatrick:         You say, “Not profesh?”

Guy Kawasaki:          Yeah, right.

Peg Fitzpatrick:         Okay, so presentation pitches, another area I know you're passionate about. If somebody wants to make a great presentation deck, what would you recommend that it have?

Guy Kawasaki:          I think it should have roughly ten slides. It should have a black background. Not white, black. It should be white text on black background. The smallest font should be 30 points, Sans-serif, bold. If you could, just use Arial Black. Arial Black on white.

Peg Fitzpatrick:         Yeah, actually you like Arial Bold.

Guy Kawasaki:          Well, I'm changing to Arial Black.

Peg Fitzpatrick:         Really?

Guy Kawasaki:          I'm upping my quality standards.

Peg Fitzpatrick:         Wow.

Guy Kawasaki:          And if you just did that, if you did 10 slides, black background, white text, Sans-serif, bold font, 30 points or more, put in as many diagrams as you can and as little text as you can. You're better than 90% of the pitches in the world right there.

Peg Fitzpatrick:         And then how long do you think … How long do people usually take to pitch? 10 to 15 minutes?

Guy Kawasaki:          Well, I very seldom read a pitch or read a Power Point … via e-mail, I just make a decision based on the 1 or 2 sentence description.

Peg Fitzpatrick:         Good to know. I hope people are taking notes.

Guy Kawasaki:          Well, they'll send me a 10MB Power Point file, and they think I'm going to go through their 60 slides, they're hallucinating.

Peg Fitzpatrick:         Yeah, that's way too … that's crazy.

Guy Kawasaki:          Because you know, one thing … a lot of times I'm reading e-mail on Virgin America using Google Wireless. You think I'm going to download your 10MB Power Point file to see that you have a patent-pending, career-jumping, paradigm shifting, technology with a proven business model and a world-class team? I don't think so.

Peg Fitzpatrick:         The best market ever. That their competitors are just stupid, right?

Guy Kawasaki:          Yeah.

Peg Fitzpatrick:         The top 10 lies of entrepreneur. Okay, so I wanted to talk about the chapter The Art of Being a Mensch. Can you explain that?

Guy Kawasaki:          Yeah, so mensch is a German word to describe someone who's truly a gentle person, trusted person, a person who defaults to yes and sees the good in everybody, and I think, you know, that should be people's goals in life. I think prime example of being a mensch is probably Nelson Mandela. You may find this surprising but I think that Bill Gates with all his work with the Gates Foundation, he's turning into a mensch. He hasn't bought a basketball team and that kind of stuff. He's out there trying to cure measles or whatever or malaria or whatever. It's not about money, you don't have to be rich to be a mensch. You just have to be kind and giving.

Peg Fitzpatrick:         Okay, you're almost home, so we will close with, if you were a startup, how would you use social media to share your startup with the world?

Guy Kawasaki:          Okay, so for most startups, social media equals marketing. This is the only marketing they can have because they don't have a lot of money. You use … I would start with Facebook probably because I think Facebook has the most targeting, the most cost effective with dark post and geographic post, you can explain all this because you know this better than I do. I would just post great content that appeals to my potential customers, that provides some information or assistance or analysis, and then I would earn the right to every once in a while promote your own product or service. Be like NPR. Provide great content, then run your pledge drive.

Peg Fitzpatrick:         Cool. Okay, well I won't take up any more of your time because I know you're going to be home soon, and then we'll see your whole house and everything. I will close with if this is of interest to you and you're an entrepreneur who would like to start, please grab a copy of the Art of the Start 2.0, and thank you Mr. Kawasaki for joining from your Uber car today.

Guy Kawasaki:          I'll show you the driver. Say hello.

Peg Fitzpatrick:         Hey Uber driver. That's awesome.

Guy Kawasaki:          Can I give one more piece of advice to entrepreneurs?

Peg Fitzpatrick:         Sure.

Guy Kawasaki:          Don't focus on Power Point, Excel, and Word. Don't focus on the business plan, the spread sheet, and the pitch. Focus on making a prototype. The concept is this MVP, like minimum viable product. I think you should make a minimum viable valuable that is important and validating, that has proved your premise, your theory. That's what you should focus on, not Excel, Power Point, and Word, okay?

Peg Fitzpatrick:         All right.

Guy Kawasaki:          All right, thank you.

Peg Fitzpatrick:         Thank you so much. Have a good day.

Guy Kawasaki:          Oh, by the way-

Peg Fitzpatrick:         Yup.

Guy Kawasaki:          We should build all the graphics with Canva.

Peg Fitzpatrick:         Yeah, I can't believe you took all this time to mention Canva, but Canva is great for a startup. They don't have money for a designer.

Guy Kawasaki:          Okay, take care.

Peg Fitzpatrick:         Okay, thanks. Bye.

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5 Comments

  1. Hello Peg, I visited your site a couple of times, but I took my time to dig deeper and was excited to find out that you have provided transcripts for someone like me who is deaf, with 100% hearing loss in both ears. It is a breeze for me to read through this instead of reading “non-perfect closed captioning” videos! Thank you for your time in creating this for people like me. Keep blogging away and I am looking forward to your newest blogs and vlogs to come.

  2. Such a treat watching/listening to this video. Loved it !
    I have recently known Guy as a name, such a great example.

    Thanks Peg!

  3. Hi Peg,

    Startup tip #9 is a ice-breaker. I have used this tip to build new relationships and cement old ones. That tip makes business a whole lot easier and makes converting people to investors/customers a better experience. I think it forms the bedrock of all the other tips because when you are thinking of how to genuinely help someone, you would put in an effort, you wouldn’t try to cut corners by copying and pasting, you wouldn’t want to take advantage of that person and you are ready to go all out to do what is needed (including doing in-depth research before a pitch, keep the mail short and sweet and cranking out an attention-grabbing title for the email).

    Selflessness is the best foundation for building a startup. I like how Guy describes Bill Gates as ‘turning into a Mensch. I have a lot of respect for both men and am quite inspired by the way they help people.

    Thanks for sharing this piece, Peg. I loved it.

    ~Chioma

  4. So thankful that I found this site. Lots of very informative post. Well detailed and easy to understand. Keep it up…

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