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

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This is a podcast episode titled, 5 Storytelling Secrets from Andy Raskin (aka The Guy Top B2B Brands Call When They Need Help With Positioning). The summary for this episode is: 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.

DG: Hey, it's DG. And I want to send you a ton of free marketing stuff right to your door or your inbox, whatever you want. I'm serious. Because look, we know how it is. One of my favorite things about doing marketing at Drift is that we are all marketers, just like you. So we're marketers doing marketing to marketers. It's crazy. And one thing we know that in the B2B world, there's so much content out there. It can be hard to figure out what to read and who to trust if you're looking to grow your business. And so we put together something that I call the ultimate conversational marketing starter kit. We asked our top customers, literally turned to them and said," What resources would you give to somebody new to Drift and conversational marketing?" And we're packaging all of that up to send right to your door for the first time for free. So that means I will send you a copy of the book I wrote with my boss, our CEO, David Cancel, on conversational marketing. This book was an instant number one new release on Amazon in three categories and it's already sold 10,000 plus copies to date. I'll literally send you the actual 262 page hardcover book right to your door. Also, we'll send you, This Won't Scale, a digital copy of our very popular book, This Won't Scale, which is a book we wrote as a marketing team about how we do marketing at Drift. It's 110 pages. It's only been available as a hard copy, but we're making it available digitally for the first time as part of this offer. We'll also send you the Modern Marketer's Playbook. You'll get a digital copy of our Modern Marketer's Playbook, which is a guide we wrote with strategic insights from 35 of today's most influential marketing leaders from companies like Slack, LinkedIn, Octa, Vimeo, and more. We'll also give you the Conversational Marketing Blueprint, which is the best next step after you read the conversational marketing book and it gives you a step- by- step guide for implementing and optimizing conversational marketing for your business. And, it's not over, the Conversational Sales Handbook. This is the guide you're going to need to give to your sales team to build your conversational sales strategy. AKA what you do after you take everything you've learned in the book and the blueprint. All you have to do is visit drift. com/ starter and grab all this stuff right now. That's starter, S- T- A- R- T- E- R. I tried to have no Boston accent on that. Drift. com/ starter. We'll send everything right to your door, or we'll literally just send an email, if you'd prefer that. Okay. drift. com/ starter. And I will see you hopefully there. 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 got for you on this episode of the Swipe File. Tune in. Andy Raskin, thank you for doing this.

Andy Raskin: Oh, man. My pleasure.

DG: You're one of my favorite people, which I tell you a lot.

Andy Raskin: Likewise.

DG: Don't let it go to your head.

Andy Raskin: Which I tell you a lot. Don't let it go.

DG: Okay. So we have the great honor of hanging out with you at Saster. We have not gotten kicked out. Despite us being outside, we have not gotten kicked out of this place. So I thought of like, what can we talk to Andy about? And I think you have this super power, which is the ability to get companies to tell a story that doesn't sound like corporate jargon, BS, what most B2B companies sound like. And I think I first started here when you did the greatest sales deck ever.

Andy Raskin: The post about Zuora.

DG: The post about Zuora.

Andy Raskin: Yeah.

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

Andy Raskin: Yeah. So there was a post I did about a year before that that was about Elon Musk. That was... It was called Want a better pitch? Watch this. It was about his keynote for the power wall 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 of really kick- started my consulting business, but yes, there's one that's gotten around 2 million views now, it's around the world. So.

DG: Holy cow.

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

DG: Yeah. And then the following year you did another one, you did an update. It was like the same... What was the Drift one?

Andy Raskin: What was that about? Oh, yeah. That was about Drift. So, yeah, that was the greatest sales pitch I've seen this year, I think it was.

DG: Okay. So crosstalk. We were this year.

Andy Raskin: I can go retroactively back to ever, and then still have that one. Like, yeah.

DG: 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 like literally print out Andy's framework. And so, if you read the Zuora stuff, if you read the one you wrote about Drift and you kind of read any of your other stuff, there's kind of like maybe four or five key ingredients. So I just... You told me you do remember them so that's good. So, I want to talk through them and just kind of 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 Raskin: Cool. Yeah. So, well, first of all, you said it's a marketing thing. And first thing I would say is you're so lucky because you have the CEO who, like I think David Cancel sees the story as his job.

DG: Totally agree. And 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 Raskin: Yeah. And marketing, of course, is going to be the storytelling kind of center of excellence that you're going to tell the story. But in all the engagements I do, I really learned like it has to be at the CEO level. If marketing just kind of 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.

DG: Just from the inside a part of this. Like 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 so he's always like, and I had a meeting with the CMO of service now 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." And so it is always something he's thinking about it. I know that.

Andy Raskin: 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 like sort of 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.

DG: The framework alone will not make you great.

Andy Raskin: Yeah. The thing that happens a lot is people say," I tried that thing and didn't work.

DG: crosstalk.

Andy Raskin: Yeah. It doesn't work. So then they'll send it to me and it turns out they've actually just sort of pasted their own logo into the Zuora slides and literally like pasted over a few words.

DG: And we believe in the subscription economy. You make bicycles. What are you talking about?

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

DG: 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 IPO's all have this one thread in common, is 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 podcast mic covers, right? It's got to be something that has that big emotional story. And so 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 Raskin: 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 of years. Right? The next step is, and this is, I think, the place, the thing that a lot of teams skip. It's a thing that a lot of storytellers skip. Is laying out the stakes. So.

DG: Yeah. I forgot about this one.

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

DG: I think it's in your article, but I think I have it somewhere in Evernote. 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 shift is happening, but you're going to miss the boat and here's what happens if you do.

Andy Raskin: And not only that you're going to, but that it's already possible, like it's already happening, like already the winners are adapting. And if you don't adapt, like you're on the road to losing. One of my favorite, like our sort of national treasure storyteller, Ira Glass, This American Life. This is one of his big things. We got a lot of great, I'm paraphrasing it, but 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 and they lay out the stakes for these car salesman, like what's at stake if they don't make their quota? And it's so big that you actually feel really sorry for the salespeople, which is like probably the most incredible storytelling feat that I've ever seen.

DG: You go 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 Raskin: Yeah. Yeah. I guess it turns out like a lot is riding on not the profit on each car, but hitting some big quota for the whole dealership and then like some big payment is at stake. And then yes, people's livelihood and their kids' education.

DG: And so, it's undeniable change, winners and losers.

Andy Raskin: Yeah. And then, so now we have their attention, you sort of 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 kind of where I learned about all this stuff. I was pitching a company and it was going really badly until I sort of found this screenwriting book. And 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 kind of what is the state that the hero has to get to, that all we want is basically committing to help him get to, in that movie, it's destroying the Death Star. In other movies, it's something else. And can you do what I call is sort of like tease the promised land, meaning like give a glimpse of it. And this functions as both a kind of goal 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.

DG: There's another good one.

Andy Raskin: I'm really cold, by the way. That's why I'm shaking.

DG: I'm cold. I'm cold.

Andy Raskin: I'm not nervous.

DG: No, no, no. It's okay. I'm cold too. I'm cold too. We're doing good. This is good. We want... The challenge of a great storyteller is we want to put you in circumstances that you're not used to and crosstalk.

Andy Raskin: You've done it. You've done it. You've done it.

DG: 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?

Andy Raskin: Yeah.

DG: And so you want to go, 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 upfront and so I know where this story is going to go.

Andy Raskin: And that's a great segue to the next piece of the framework because most companies, they start out with, what is the problem? What is the problem? What is the solution? This is a kind of metaphor. The company is the problem solver in sales, like traditional sales culture, it's the doctor. Doctor, patient. 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 start to get pushed down very low in the org. When you start this other way with the promise land, and as you said, now, you talk about, well, okay, if that's where we want to get to, destroying the Death Star, just having conversations with people, then what's stopping you from doing that? What's in your way? And 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.

DG: I think that's such a valuable exercise though, as a marketer or a storyteller or whatever, sales person, is to say, it's actually go through and lay out all the objections somebody's going to have. Right? Like 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 can 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 upfront.

Andy Raskin: It's objections and it's also sort of like 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 just sort of disembodied problems.

DG: Totally.

Andy Raskin: Yeah.

DG: Okay. That's four.

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

DG: It's the freaking Death Star. How are you going to have these crosstalk?

Andy Raskin: Really, me as sort of like a lean teenager is going to destroy that Death Star. Me, as a marketer sitting behind forums, I'm going to just have a conversation. How's that going to happen?

DG: Totally.

Andy Raskin: I look at ones like Airbnb. A lot of people call this the tagline, but I like to call it the promise land message. Live there. Really, I'm going to live in the place rather than be in a hotel.

DG: It's somebody else's house.

Andy Raskin: Right. And so we need to give them some evidence so that we can make the story come true. And so that's the things like, well, Jobs was great at the product demo. Hey, here's the... You can't get the phone yet, but here's what your life is 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 promised land or at least kind of on the way. So those are testimonials and what go by the horrible name, case studies, but stories about that.

DG: Proof. You need proof. Because I think it sounds funny because marketers have always needed, ask any salesperson, they need more case studies. Right?

Andy Raskin: Yeah.

DG: But I think it's more important than ever today because of what, you talk about a lot, like the whole reality TV thing that we do. 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 so more skeptical than ever today. Every sales rep is going to tell me their 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. And so you do have to have some facts to back it up.

Andy Raskin: Yeah. But what I love is, 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, like evidence that we are the best. And 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.

DG: And I think we, like I'm just obsessed with finding examples that are like somewhat related to us outside.

Andy Raskin: Yeah.

DG: Like every day 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?

Andy Raskin: Yeah.

DG: 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. Why can't that happen on your website? That has nothing to do with Drift. But it's like these related stories that get people to see.

Andy Raskin: Right.

DG: 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."

Andy Raskin: Yeah.

DG: My mom doesn't care about conversational marketing and sales tactics and that, but she knows the problem of like, yeah, I hate going to somebody's website and freaking waiting.

Andy Raskin: Yeah. And 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 really goes back to that change in the world that you believe in and that the whole company is kind of built around.

DG: 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 Raskin: Yeah. So, I mean, 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 comment. They'll often ask this question. And so that's one of the things I say," Well, what's the best we can show him? Do we have... Even maybe product demo is all we can do at this point or whatever.

DG: Or a quote of somebody saying," This would be amazing if I blah."

Andy Raskin: Yeah. Which is not great, but maybe that's the best they can do.

DG: Yeah. All right. Let's hit him 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 Raskin: Stakes.

DG: Stakes. Number three. What's number three?

Andy Raskin: Tease the promised land.

DG: Tease the promised land. Show them the path of the future. Number four?

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

DG: 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. A. Raskin on Twitter. Right?

Andy Raskin: A. Raskin on Twitter. Yeah, that's right. That's right. Or connect on LinkedIn. That's where I'm always posting stuff.

DG: crosstalk.

Andy Raskin: Yeah. I heard you post some stuff over there too.

DG: 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. And so, because it's fun for me, I hope it's fun for you. And it would mean the world if you could leave a review. Reviews really help. And so, go leave a review. Go to Apple Podcasts. Leave a review. Let me know what you liked in the show, didn't like, want to hear more of. And also, if you're not already subscribed, make sure you go subscribe on Apple Podcast, Spotify. The show is everywhere that you get your podcasts, probably where you're listening right now. But if you want more content like this, if you want to go a layer deeper, join me on Drift Insider. It's drift. com/ insider. We're teaching courses, we're sharing videos, and we have exclusive content for people just like you in marketing that we do not share publicly. So go and check it out. drift. com/ insider.


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.