5 Storytelling Secrets From Andy Raskin (aka The Guy Top B2B Brands Call When They Need Help With Positioning)

On this episode of the Marketing Swipe File, DG sits down with Andy Raskin – who he calls a Silicon Valley storytelling mastermind. Andy Raskin is a highly sought-after consultant who knows a good story when he sees one. Case and point, his post “The Greatest Sales Deck I’ve Ever Seen” has become an internet sensation, with nearly 80k views on Medium. So we got Andy to spill his top five storytelling secrets. The ones he usually only shares with CEOs and CMOs. Secret number 1? State a big, undeniable change happening in the world. Secret number 2? Show that there will be winners and losers. Want the rest? Listen to the full episode.

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Full Transcript

Dave Gerhardt: Hey, everybody, it’s DG. One of my favorite episodes of the Swipe File coming up. Why is it one of my favorite episodes? Because I sat down with Andy Raskin, the man, the myth, the legend himself. Andy is a Silicon Valley storytelling mastermind. But instead of interviewing Andy for this one, and saying who are you, what do you do, blah blah blah, I said, “Andy, I want to know your five secrets for storytelling. Give them to me, step one, step two, step three, step four, step five,” And that’s what we’ve got for you on this episode of the Swipe File. Tune in.

Andy, thank you for doing this.

Andy Raskin: Oh, man. My pleasure.

Dave: You’re one of my favorite people, which I tell you a lot-

Andy: Likewise-

Dave: … don’t let it go to your head.

Andy: … which I tell you a lot, don’t let it go to your head.

Dave: Okay. So, we have the great honor of hanging out with you at SaaStr. We have not gotten kicked out.

Andy: Yet.

Dave: Despite us being outside, we have not gotten kicked out of this place. So, I thought of, like what could we talk to Andy about? And I think you have this superpower, which is the ability to get companies to tell a story that doesn’t sound like corporate jargon BS, what most B to B companies sound like. And I think I first started to hear of you when you did this, The Greatest Sales Deck Ever.

Andy: The post about Zuora.

Dave: The post about Zuora.

Andy: Yeah.

Dave: Did you notice an inflection point in people asking you for stuff after that?

Andy: Yeah. There was a post I did about a year before that, that was about Elon Musk, it was called Want a Better Pitch? Watch This. It was about his keynote for the Powerwall where I first kind of started talking about this, structuring the pitch, and starting to talk about doing it almost like a movie, the similarities there. That one kind really kickstarted my consulting business, but yes, there’s one that’s gotten around two million views now, it’s around the world, so-

Dave: Holy cow.

Andy: Yeah, companies around the world, I’ve been totally privileged to work with them on how a leadership team tells a story.

Dave: Yeah. And then the following year, you did another one. You did an update. It was like the-

Andy: What was that about?

Dave: Was it the Drift one?

Andy: Oh, yeah, that was about Drift. So, yeah, that was The Greatest Sales Pitch I’ve Seen This Year, I think it was.

Dave: Okay. So, Zuora was ever. We were this year.

Andy: I can go retroactively back to ever, and then … yeah.

Dave: Okay. So, anyway, I don’t want to talk about us. I don’t. What I want to talk about though is, you told me that you will be nice enough to share the thing that you usually only share with CEOs, CMOs, which is … you have a recipe for telling these stories, which, I think if you’re a marketer watching this, you’d be crazy to not literally print out Andy’s framework. So, if you read the Zuora stuff, if you read the one you wrote about Drift, and you read any of your other stuff, there’s like maybe four or five key ingredients. You told me you do remember them, so that’s good.

Dave: I want to talk through them and just give people … this is for our marketing show, and I’m obsessed with having frameworks. I don’t think you can framework everything, but as far as like telling a story, so, for example, I stole one from Steve Jobs that I use for all of our decks and landing pages. And it’s five steps, it’s like, tell a story, pose a problem, blah, blah, blah, and that’s been super helpful. But I like yours a little bit better, and I want to go through the steps.

Andy: Cool. Yeah, well, first of all, you said it’s a marketing thing. First thing I would say is, you’re so lucky because you have this CEO, who, I think David Cancel sees the story as his job, you know?

Dave: Totally agree, which is fun to think about. If you go back and rewind any of the companies that have been great at this, Salesforce-Benioff, Apple-Steve Jobs, Amazon-Bezos, Tesla-Elon Musk, right? All those CEOs do care that much about storytelling.

Andy: Yeah. And marketing, of course, is going to be the storytelling center of excellence that you’re going to tell the story. But in all the engagements I do, I’ve really learned, it has to be at the CEO level. If marketing just takes this on as the project, like, “Oh, we’re going to create the story,” and then pushes that into sales, it’s not going to work as well.

Dave: Just from the insider part of this, I can tell you that Dave, I have not worked with any of those other guys, but from David’s perspective, he is maniacal about … you might think right now we have a good story, but I can tell you that he’s texted me at 8:00 yesterday saying, “We need to work this in, we need to rev on this.” And I had a meeting with the CMO of ServiceNow yesterday, and I sent David a video after because he said something in that conversation, he said, “You and me, we got to rev on this, we got to work on this.” So it is always something he’s thinking about, I know that.

Andy: Yeah. And I think the greatest CEOs who think about this, or, yeah, I mean they have the basic story that they’re telling all the time, but it’s never final. It’s always evolving a little bit. The framework that you talked about, and like you said, it’s just a framework, it’s just some principles. It’s not a template, so-

Dave: The framework alone will not make you great.

Andy: Yeah. The thing that happens a lot is people will say, “You know, I tried that [inaudible 00:04:59] and didn’t work.

Dave: Andy, you suck.

Andy: Yeah, doesn’t work. Then they’ll send it to me and what it turns out, they’ve actually pasted their own logo into this [inaudible 00:05:11] slides and literally pasted over a few words.

Dave: And we believe in a subscription economy. You make popsicles, what are you talking about?

Andy: They have maybe a different economy. But every team that I work with, we start with that rough structure, but it never exactly works, we always have to massage into whatever is really going on for them. The structure is really, the first thing is starting with this undeniable, relevant, newish change in the world. This is essentially the same thing as the Play Bigger folks are talking about. It’s this point of view on what has changed.

Dave: I’m glad you mentioned them because that … you should go read the book Play Bigger because they go and break down basically all the big companies in the last 20 years, very successful IPOs. All have this one thread in common, in that they’ve created a category, and by definition, you can’t really have a category … we can’t be creating a category about like these podcasts might cover, right? It’s got to be something that has that big emotional story. I love your thing because it immediately starts with not a feature, not a product, but a, “Hey, look, this undeniable thing is happening in the world. Do you agree?” “Yes.” “Okay, next.” Right?

Andy: And you agree, you’re with us. You don’t agree, you think the world is not changing that way, “Okay, we’ll see you in a couple years,” right? The next step is, and this is, I think, the place, the thing that a lot of teams skip. It’s the thing that a lot of storytellers skip is laying out the stakes.

Dave: Yeah, I forgot about this one.

Andy: Because of this change, why, if you stick to the status quo are you on the road to ruin?

Dave: I think it’s in your article, but I have it somewhere and never know. It’s like, “There will be winners and there will be losers.” And you have to show the real pain of like, “Not only can you agree that this shit is happening, but you’re going to miss the boat and here’s what happens if you do.”

Andy: And not only that you’re going to, but that it’s already, if possible, it’s already happening. Already the winners are adapting and if you don’t adapt, you’re on the road to losing. One of my favorite, our sort of national treasure storyteller, Ira Glass, This American Life, this is one of his big things. He says we’ve got a lot of great, I’m paraphrasing here, we get a lot of great pitches for stories, but the good ones have to lay out the stakes.

One of their famous episodes is about, they spend like an hour in a car dealership. They lay out the stakes for these car salesmen, like what’s at stake if they don’t make their quota. It’s so big that you actually feel really sorry for these salespeople which is probably the most incredible storytelling feat that I’ve ever seen.

Dave: You go in and you hear from the person who’s going to miss a paycheck and their family’s not going to … whatever, right? And you’re like, “Oh, man, I feel that.”
Andy: It turns out a lot is riding on not the profit on each car, but hitting some big quota for the whole dealership and then some big payment is at stake and then, yes, people’s livelihood and their kid’s education are at risk.

Dave: Okay, so undeniable change, winners and losers.

Andy: So now we have their attention, they see the stakes and now the next thing they want to know is, “Well, what’s it going to take to win? What does it take to be one of these winners?” All of this has a real analog and movie structure, that’s where I learned about all this stuff. I was pitching a company and it was going really badly until I found this screenwriting book. You think about all the great movies, Star Wars, of course, is a good one because a lot of people have seen it, they lay out very early what is the state that the hero has to get to that, all we want is basically committing to help him get to.

Andy: In that movie, it’s destroying the Death Star, in other movies, it’s something else. And can you do, what I call, is tease the Promised Land, meaning, give a glimpse of it. And this functions as both a gold state for the customer, but also a commitment from the company like, “This is what we’re going to get you to.” In this way, I really see this as the mission statement, but it’s the mission statement from the customer’s point of view versus some kind of self-centered thing.

Dave: There’s another good one.

Andy: I’m really cold, by the way-

Dave: I’m cold.

Andy: … that’s why I’m shaking.

Dave: I’m cold.

Andy: I’m not nervous.

Dave: No, no, it’s okay. I’m cold too. I’m cold too. We’re doing good. This is good. The challenge of a great storyteller is, we want to put you in circumstances that you’re not used to and can-

Andy: You’ve done it. You’ve done it.

Dave: … come and still stay. I was going to say, I learned a great lesson from Aaron Sorkin, not personally, but from Masterclass which is amazing. He does a class on screenwriting. And he said something really simple which is so powerful, which is, “Every great movie, every great story has intentions and obstacles, right? So, ‘I want to go home tonight, but the car’s broken down and I can’t. And I want to get there because … ,'” blah. And you set that up up front and so I know where this story’s going to go.

Andy: That’s a great segue to the next piece of framework because most companies, they start out with what is the problem? What is the problem, what is the solution? This is a metaphor, the company is the problem solver in sales, traditional sales culture, it’s the doctor, doctor/patient. You know, you get this, “We’re going to look for pains and here’s how we’re going to relieve the pains. Marketing’s job is to arm the sales team with a list of pains.” But if you start there, if that’s the starting point, then we don’t really understand what the stakes are. And then what happens is, you get this thing where only the people who really have the problem, really care about it. So you get pushed down very low in the org.

Andy: When you start this other way, with the Promised Land and, as you said, now you talk about, “Well, okay, if that’s where we want to get to … ,” you know, destroying the Death Star, just having conversations with people, then what’s stopping you from doing that? What’s in your way? There’s probably going to be a lot of big things in the way because this Promised Land should be pretty hard to get to.

Dave: I think that’s such a valuable exercise though as a marketer or a storyteller, or whatever, sales person, is to say, is actually go through and lay out all the objections somebody’s going to have. They have to destroy the Death Star. What are all the things that could happen along the way? And then actually make those part of your story because then you could be like, “I know you’re probably thinking they’re going to do … ,” blah, “Well, they don’t, they actually do … ,” this. And you handle all the objections up front.

Andy: It’s objections, and it’s also challenges they’re going to have that you’re anticipating like what’s going to be hard for them. Because if it’s easy, they don’t need you. But, yeah, so positioning these things as obstacles to a goal versus disembodied problems.

Dave: Totally, okay. That’s four.

Andy: And then, the last piece is, even if we’ve done this really well, then the buyer, the prospect, should still be kind of skeptical because this Promised Land, we’ve set it up to be really aspirational, hopefully, but also really hard to reach.

Dave: It’s the freaking Death Star, how are you going to have these three people destroy it?

Andy: Really, Mia, a lame teenager, is going to destroy that Death Star? Me, as a marketer sitting behind forms, I’m going to just have a conversation? How’s that going to happen? I look at ones like Airbnb. A lot of people call this the tagline, but I like to call it the Promised Land message, “Live there. Really, I’m going to live in the place rather than be in a hotel?” We need to give them some evidence that we can make the story come true. That’s the things like, “Well, Jobs was great at the product demo. Hey, you can’t get the phone yet, but here’s what your life’s going to be like. You call the Japanese restaurant,” just by moving his fingers around which was pretty cool back in the day. But, of course, the best evidence is stories about customers you’ve already gotten to the Promise Land or at least on the way, so those are testimonials and go by the horrible name case studies, but stories about that.

Dave: Proof.

Andy: Yeah, proof.

Dave: It sounds funny because marketers have always needed, ask any salesperson, they need more case studies, right?

Andy: Yeah.

Dave: But I think it’s more important than ever today because of what, you talk about it a lot, like the whole reality TV thing that we do, right? The reason why that matters is, because I think marketers have the hardest … we’re entering the hardest decade, I think, for marketers because even if you’re so good at what you said, undeniable change, here’s the problem, here’s the solution, right? People are still like, “I don’t believe you.” We are all more skeptical than ever today. Every sales rep is going to tell me they’re thing is faster, it’s better, it’s easier to use, it’s whatever … even if it’s true, which sucks for them because they’re not going to ever convince me so you do have to have some facts to back it up.

Andy: But what I love … especially what you do, and I think I’ve seen some others, it’s like most companies are selling a solution, and they’re giving evidence of the solution, evidence that, “We are the best.” What this framework is really about, and I think what I see you guys doing is, it’s more about you’re selling belonging to this group of believers who believe in the story you’re telling. And the proof is, of course, you’re always talking about how folks are using Drift, but a lot of it is about the proof of thriving and winning in the world of conversational marketing.

Dave: And I think, like I’m obsessed with finding examples that are somewhat related to us outside. Everyday I walk home from work and there’s a Bank of America right there. And the big window of Bank of America positions their app now as a 24/7 banking assistant, right, or, I use the Lyft example all the time. It’s like, “After this, I’m going to go back and we’re going to get lunch. And I’m going to pull up Lyft on my phone and they’re going to scan the area for a driver near me and find someone for a ride.”

Dave: Why can’t that happen on your website? That has nothing to do with Drift, but it’s these related stories that get people to see and that’s a story that I can take to a room of non marketers, I can take to my family at Thanksgiving and say, “You know what? Don’t you hate how when you go to a website and you do … ,” blank? “Well, we’re solving this problem.” My Mom doesn’t care about conversational marketing and sales tactics and that, but she knows the problem of, “Yeah, I hate going to somebody’s website and freaking waiting.”

Andy: Yeah. This really gets to, it’s not just that, it’s everything you do. You know that thing where you’re doing videos while you’re walking and drinking your greens. It’s that whole authenticity message, of course it stands alone, but it also is very connected, I think, to the Drift story. Everything you’re doing is really, goes back to that change in the world that you believe in and the whole company is built around.

Dave: What would you do, before we wrap up because I’m freezing too. What would you do if you’re a company, and you’re a little bit newer company, newer startup, whatever, and you don’t have all those case studies. Can you still do this in a compelling way without the facts yet?

Andy: Yeah, first of all, it’s a wake-up call to say, “Hey, let’s do some kind of beta. Let’s do something, that it’s really important, can we get something like that?” I run a lot of workshops where early stage founders will come and they’ll often ask this question, so that’s one of the things I say. What’s the best we can show them? Do we have, maybe product demos, all we can do at this point, or whatever.

Dave: Or a quote from somebody saying, “This would be amazing if I … ,” blah.

Andy: Which is, not great, but maybe it’s the best they can do.

Dave: All right. Let’s hit them with the recap, if you can remember off the top of your head. Number one is, state a big undeniable change happening in the world. Number two is, show that there will be winners and losers.

Andy: Stakes.

Dave: Stakes. Number three, what’s number three?

Andy: Tease the Promise Land.

Dave: Tease the Promise Land, show them the path to the future. Number four …

Andy: Summarize the obstacles and show how you can help overcome them.

Dave: What he said. And then, the fifth one is proof, show examples.

So awesome, Andy, I can’t get enough of the stuff you write. So if you’re watching this, and you’re not listening or reading Andy’s stuff, go and check him out, araskin on Twitter, right?

Andy: Araskin on Twitter, yeah, that’s right, or connect on LinkedIn, that’s where I’m always posting stuff. Yeah, I heard you post some stuff over there too.

Dave: I dabble, I dabble.

All right, Andy. Thank you for doing it.

Hey, thanks for listening to another episode of The Swipe File. I’m having a lot of fun doing this podcast. Because it’s fun for me, I hope it’s fun for you. It would mean the world if you could leave a review, reviews really help and so go leave a review. Go to applepodcast, leave a review. Let me know what you liked about the show, didn’t like, want to hear more of. And also, if you’re not already subscribed, make sure you go subscribe on applepodcastspotify, the show is everywhere that you get your podcasts, probably where you’re listening right now.

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