Episode 22 | Part One: The Communications Guru

Gregory Shepard, an entrepreneur who's built and sold 12 businesses, a recipient of 4 private equity awards, TEDx speaker, and Forbes author. This is The Boss Podcast with Gregory Shepard.

So you've come up with a great idea, but what are you going to do next? Well, my next guest might be able to help you. His name is Carmine Gallo, and he's been called the communications guru. Carmine is a keynote speaker, Harvard instructor, and bestselling author of books like Talk Like TED and The Presentation Secrets of Steve Jobs. Carmine, thanks so much for joining me on the podcast.

Oh, thanks, Greg. Thanks for inviting me. It's a great audience— investors, entrepreneurs. That's who I write for.

That's perfect. It's perfect. That's why we were so happy that you accepted the invitation. I'm a big fan of your Twitter feed. And your profile says that you're number one in transformative communication. And I wondered if you could just break down what transformative communication is for the folks.

Transformative, meaning to transform an individual or a company or a startup or an idea. Most entrepreneurs or leaders who I work with are good or average public speakers or communicators. But if they can take their skill to just another level, not significantly better, just let's just take it one more notch higher so that everything you pitch and present is more persuasive, clear, specific, concise, it makes a dramatic transformative difference in their careers and in their companies, especially given our audience. When I work with entrepreneurs who are pitching during IPO roadshows, Mm-hmm. Venture capitalists and analysts and bankers and investors tell me that that makes a big difference because you can explain a cloud computing company, for example. I worked with a big Silicon Valley cloud computing company last year that was one of the few IPOs last year. And they can speak very well to their peers. They can grow very well internally, But once they're in front of bankers who don't understand the very complex nature of what they do, then it becomes imperative that they are clear, understandable, concise, emotional, inspiring, you know, to generate that enthusiasm. So I believe so much of success in entrepreneurship comes down to how well you can talk and express your idea. Right, Greg? I mean, you can have the best idea in the world. If you cannot express yourself in a way that moves people to action, then who cares? What does it matter?

100%. I mean, you know, it's interesting you say that because I look at probably, I don't know, 100, maybe 200 investments, you know, on a monthly basis. And a portion of those I have conversations with. And the large majority of that group, it's very difficult to get them to answer the questions precisely. You know, everything is really broad and you end up having to say— I can't tell you how many times on a phone call I have to say, can you unpack that for me and give me the details? I agree with you 100%. This is a critical misstep that entrepreneurs make all the time.

It's interesting that you still get that reaction, that you still have to say that. That's the point. You should, as an entrepreneur, you should be doing your homework well ahead of time. People want to know what's in it for them. Why should I care? The basic questions that go back to journalism school. When I went to— I got a master's in journalism at Northwestern many years ago. That's Journalism 101. That's the first day of class. Answer the question, why should I care? It's amazing to me how many entrepreneurs and anyone with an idea They start in the middle. They get into the details. They talk about their solution because they are enamored with their solution. It's the greatest thing in the world. But they never answer, who cares? What is the problem you solve? Why should I care? What does it mean to me?

Yeah.

Basic questions. Answer those up front and at least you'll get some— you'll get interest. You'll get someone like yourself, like Greg, to say, that's interesting. Tell me more.

You know, this is a really interesting topic for me because what I've done is over the past, you know, 5 years, we did a study to find out why entrepreneurs failed. We had like 5 people, we did all these interviews and all this data and everything. And one of the places they fail is right up front. And one of the reasons why they fail right up front is because they can't explain their business to people that don't understand their business in a concise way. I think what you bring to the table helps out with that. And one of the questions I wanted to ask you By the way, I'm a huge fan of your Talk Like TED. Before I did my TED Talk, I did the audiobook probably 5 times. So, just to throw that out there.

Oh, you poor man. You actually had to hear me speak in your ear for all those hours?

I thought it was fantastic, actually. I just put it— I had a long drive and I just put it in and I would just play it over and over and over again. So, I think it's fantastic. I would advise any entrepreneur to Uh, read that book and look at the advice and then apply it. Uh, just to throw that out there, it's really—

Can I bring up one thing about Talk Like TED that applies here? So I wrote a book, like you mentioned, it was called Talk Like TED. It was based— it is based on the TED conference, but it's not necessary. I'm glad you used it for your TED Talk. It's not necessarily a book— this is not where I intended it to go— to be a book that's meant for people who speak at TED. It was intended to capture some tips and advice and techniques from people who are among the best speakers in the world. What have they learned? But as it turned out, you know, Greg, it brings up a lot of interesting tips and techniques that anyone, especially entrepreneurs, can use to pitch their ideas because When you have to create a TED Talk and it's only 18 minutes, you have to be clear and concise and interesting in 18 minutes, which is the same techniques that apply to an entrepreneur who's pitching investors.

100%, especially, you know, they do a lot of these pitch competitions and they have like 8 minutes, 10 minutes to pitch an entire business and unpack that and get investors' interest. And I found that, you know, after I went through the book, You know, I think 10 times or something. And then, I wrote all these notes and everything. I went to TED and then, they give you a coach, you know, a coach to help you out. And the stuff that the coach brought up was similar to the things that you brought up and I already knew them and it was kind of fun.

Oh, great, great. You know what's amazing though, what I've learned not only after writing a book about the TED Conference but writing a book about— years before that, I wrote the first book on how Steve Jobs gave. Presentations. So that was called The Presentation Secrets of Steve Jobs, which a number of companies, startups, and even unicorns have used to create their pitch decks and presentations. So it's still really relevant. But whether or not you look at TED or Steve Jobs or other speakers in a number of different areas, they all are arriving at the same conclusions. I just— I read a book a couple of years ago by Alan Alda. The actor is really into communicating science. Well, I read his book. He had a lot of studies that I've talked about in Talk Like TED. He uses very much the same approach. We reached the very same conclusions. I came at it from working with entrepreneurs in Silicon Valley, and he came at it from acting, and we reached the same conclusion, exactly the same conclusion.

That's fascinating.

I think there's a formula here, Greg. I really don't think it's something that we have to overthink.

There's a formula to it which you've mastered. Let me ask you a question. When you look at these entrepreneurs that are pitching or anybody doing, you know, keynotes or any speaking engagement, is there a commonality between why their speeches aren't good and are good? Is there, you know, you're talking about this formula like an algorithm. Right? Is there an algorithm on both sides that you could help the listeners with in terms of what makes a good talk and what makes a bad talk?

Algorithm. I love that. Spoken like a true startup investor. Show me the algorithm.

I'm a tech nerd, so I—

That question isn't always phrased that way. But yeah, I think it— what's remarkable is the tools of communication have changed. So here we are on a podcast, or we're using PowerPoint, or you're using online tools as well. They didn't have those tools 2,000 years ago when Aristotle was roaming the planet. But the same tools of persuasion that Aristotle wrote about 2,000 years ago are the same ones we're using today. We just use different tools to get that information across. So, my whole idea is that the formula has remained the same and consistent for thousands of years. We know how this works. We don't always implement it, but we know how it works. So, one thing I've really gotten into, Greg, recently, I don't want to use a cliché, but storytelling. And storytelling, really storytelling narrative, it's crucial.

Yeah.

To any type of pitch or presentation or to grabbing people's interest. When I wrote the book on Steve Jobs, I used presentations. That was the word I used— how to deliver a better presentation, how to create a better presentation. And not too long ago, Tony Fadell, who went on to build Nest, you know, and sell it to Google for billions of dollars, he worked with Steve Jobs side by side for many years. Tony Fadell was on a podcast, another interview and they asked him, what did you learn from Steve Jobs? And Tony said, storytelling, storytelling, storytelling.

Hmm.

And it dawned on me, Greg, that even though I wrote the book on how Steve Jobs created presentations, I never used the word storyteller. So, I think that— and then after TED, I started using storytelling. I think storytelling is the key. And most venture capitalists I've talked to, and I've talked to some of the top ones in the Valley, They're even the ones who bring up storytelling, especially for early entrepreneurs, because if you cannot bring them into the journey with you, if they don't understand the journey, the hero's journey— why is this taking place? What is the adventure we're on? What are the hurdles and the obstacles that we can encounter? What is the end goal? What is the reward at the end of the movie? If you can't bring them on a journey, it's really hard to convince them to invest in the company or to take action on your ideas. So this whole idea of storytelling has become a central focus for what I'm— for what I write, for what I look about, and the whole lens now of looking at pitches, presentations, communication It's all through the lens of story now. I'm sort of obsessed with storytelling.

You could probably help me out with my story.

I am not good at storytelling. This is creative. This is the creative stuff. And PowerPoint is not a storytelling tool. You open PowerPoint, you start filling in bullet points. That's not narrative. It's not storytelling. So, I've been going back to analog, you know, and I get my— these entrepreneurs or clients who I work with, let's get on the whiteboard. Let's do sketches like a director would before they even start filming a movie. They're still— they're called— it's called storyboarding in Hollywood, right? It's all about sketching out the scenes. What story are we trying to tell first? Then we can use PowerPoint to complement the story.

Instead of the other way around, right?

Yeah, that's the algorithm. Algorithm is Don't start by opening PowerPoint. Start by sketching out the story, the journey that you want to take people on. The tool PowerPoint is going to complement the journey, but it's not creating the journey.

So let me, let me sharpen that a little bit. So when it comes to speaking, you emphasize that it's important to always express the big picture before you go into detail. Because some people get lost in the minutia. So, how do we focus on the big picture in a more tactical way?

Oh, okay, good. Uh, that again, that everything we're going to talk about, Greg, falls under story, which is why I begin with story. Okay, but how's it— what's a good story to start with? Okay, um, a good story sort of starts with the big picture, a headline. If you read any newspaper column, what's, what's the headline? What's the one thing that this story is about? Well, why don't we do that in a business presentation? Why do we bury the headline in the middle of the presentation or wait till the end? This is not a novel, okay? You're not Hemingway. You're not waiting till the last page for the big reveal. An investor has very limited time. They just want to know what's in it for me. And give me the story right up front. Then you can back into it with the details once you've got me hooked.

Oh.

That's why I say let's start with the big picture. And getting back to story, in— I think I wrote about this in Talk Like TED for the first time. I like to speak to screenwriters, Hollywood screenwriters, because I learn a lot from them. They're great storytellers. In Hollywood, and this is a real thing that happens, if you are a screenwriter and you have a film to pitch, and those guys go through pitch meetings, you know, multiple times a day for new movies, they want to know in one sentence, and they call it the logline, in one sentence, what's your logline? The logline is the movie poster, Greg. It's the poster. It's in one sentence, what is this movie about? Every movie that's ever pitched in Hollywood has to have a logline. They even have books for screenwriters. So, that's how hard this is, Greg. It's you have to distill your movie in one sentence. So, how does that apply to entrepreneurship? I remember having a— you'll know this name, Michael Moritz at Sequoia Capital.

Yeah.

Right? One of the great investors who backed Yahoo and Apple and Airbnb and so many other startups. So, Sequoia Capital, one of the biggest firms in the Valley. He told me this story. He said the Google guys, Sergey Brin and Larry Page, walked into his office one day and it was a Friday. He remembers this because I think they invested by that Monday. Brin and Page walk in and they say, Google— and they said, look, we've got this idea for a company, we call it Google, that it allows anyone to access the world's information in one click, right? So make the world's information accessible, which I think is still very much part of their, like, mission or vision statement. Make the world accessible. Make the world's information accessible in one click.

Mm-hmm.

And Michael Moritz says to this day, he still remembers how clear they made that message. So, his next question is, well, that's interesting. Let me see how it works. So, now he's interested.

Yeah.

But then— and here's the key, Greg. Michael Moritz told me that after that day, he always demanded of entrepreneurs who walked into his office, I want to know what your idea is in one sentence. And then he said, if they cannot express their idea in one sentence, I'm not interested, period.

Yeah, that Bezos follows the same logic.

Yeah, yeah, you're absolutely right. It's like, give me, give me the big picture, the big picture in one sentence.

So when you're crafting a story then, right? So are you basically taking the journey of your business into a byline, if you will, right? Like a trailer, a movie trailer, that poster that you mentioned, and then that's your opening to the conversation, right? That's your opening. And then do you wait then for them to ask the next question before you go on, or do you— what do you do now? So, you've got their interest, you've done the byline, now what?

Often you can start with that personal story and tell that story in 60 seconds. Right now, just in the past few days, I've been reading more about Canva. Melanie Perkins, who I've interviewed a couple of years ago. So Canva has just become the most valuable female-founded startup. It's valued at $40 billion. They just got a new infusion of $200 million a couple of weeks ago as we're talking on this podcast, a new round of infusion. So they are all about online design. Well, from day one, Melanie Perkins' mission was to, quote, democratize design, to empower anyone in the world to make beautiful simple designs easily and quickly. If you're listening to how I'm trying to articulate that, Greg, sometimes my words could change. I don't work for the company, so it's not exact, but just by reading her interviews, I understand, I get it. In one picture, I understand what they're trying to do. And I love this whole term democratized design. Then only once she gives you the big picture, this is what, who we are, this is what we are trying to do. Online design to make it easy for anyone to make beautiful designs. Okay, I got it. In one sentence, I understand at least where your company or startup falls into. Now I can categorize it. But almost immediately, Melanie goes right into, let me tell you why. She tells you the why before the how. She doesn't pitch it by saying, this is how it works. Yeah, we'll get to that. First is why. And now, almost always, in every interview I've heard her in the last few months, she always goes back to the story. In 2007, so, you know, most of your listeners may have heard this by now. In 2007, she was teaching Adobe Photoshop and other design programs at a university in Australia. And she realized just how frustrating and how difficult it is to teach and to learn those programs that were still based on the desktop. Why couldn't this be remarkably easy online? Like other social media sites are making things easy. Yeah. Easy online. And that's where it was born out of that frustration. And anyone can understand that frustration. So she goes right back to that story. That's what I mean, Greg, by first give me the big picture. What is this company about? What does it do? Just so I can have a mental category of where you fit. But then she gets into the story. And it's that story that draws you in. Because as she has said, if people don't understand the story, and they don't know my background and why I started Canva, they will not understand the why. And then we'll be getting right into the how. Well, the how can be confusing until you learn why it's even necessary. And the best vehicle we have to transfer that knowledge of why is through story.

I think that's impressive, to say the least. All right, unfortunately we have to stop here, but coming up in the conclusion of my conversation with Carmine Gallo, In an 18-minute TED Talk or a short presentation, you cannot bombard people with everything you know about the topic.

Give them 3 things to take away. Give them 3 reasons to invest, 3 reasons why this is going to be a multi-billion-dollar category, not 28.

Learn more about the Boss Business Podcast at bossbusinesspodcast.com. Operating Support System at bossstartupsience.com, or you can reach Gregory Shepard at gregoryshepard.com. This has been a production of Forbes Books.