The New Game All the Winners are Playing, with Andy Raskin

#49: Andy Raskin is an expert in messaging and positioning, and has helped some of the fastest growing companies in the world align their team around a strategic narrative.

In this episode, we cover the biggest mistake most businesses make when telling their story, and how to tell a strategic narrative that will instantly establish trust with your audience and turn them into customers.

If you’ve been looking for a better way to tell your own story, you’ll definitely want to listen to this episode.

Podcast Episode Summary

In this episode, you’ll learn:

  • what the Promised Land statement is;
  • how he applied this framework into his sales pitch for his work; and
  • how content plays a role in his business


The dominators, the ones that have broken out of the noise, they started from a very different place. And the place is this change in the world. (08:10)

When people play a game or really adopt the narrative, there’s gotta be some goal. Like what is the point of no return in a good way for happily ever after? So what’s the finish line? (11:46)

If you could turn all your customers into subscribers, you’re a winner. (13:15)

Content made my business possible. (14:26)

Connect with Andy Raskin 

LinkedIn: Andy Raskin

Podcast: The Bigger Narrative

Ep. 49: The New Game All the Winners are Playing, with Andy Raskin

Andy (00:01):

The basic story that the company tells that everyone's selling, iIt has the form of you have a problem. We have a solution. Let me tell you why ours is the best solution. It pretty evolves quickly into bragging. And so this shift like, Hey, there's this new game. Look at all the people who are winning. They're all playing this new game. It's kind of setting up this club of winner.

Josiah (00:25):

Welcome to Content Heroes, everyone. We're back with another great conversation to help you build a profitable business on your own terms by creating content online. Our guest today is an expert in messaging and positioning, and he's helped some of the fastest-growing companies in the world align their team around a strategic narrative. We're going to cover the biggest mistake most businesses make when telling their story and how to tell a strategic narrative that will instantly establish trust with your audience and turn them into customers. If you've been looking for a better way to tell your own story, you'll definitely want to stick around for the rest of this episode. So let's jump in.

Announcer (01:00):

You're listening to the Content Heroes podcast, where entrepreneurs, marketers, and creatives share how they build profitable businesses on their own terms by creating content online. And now your host Josiah Goff.

Josiah (01:16):

I'm here with Andy Raskin who works with CEOs to align their team around a strategic narrative. And I'm really excited about this conversation. Andy, thank you so much for being on the show today.

Andy (01:26):

Thanks for having me, Josiah.

Josiah (01:28):

So Andy, you know, I've been following your work for several years now and you work with leadership teams from places like Salesforce and Square and Dropbox and IBM and Uber, which is fantastic. I'd love to hear your story of how you got to where you are.

Andy (01:44):

Okay. How much time do we have? I'll try to do the kind of short version. So yeah, I actually started as a Software Engineer. My background was Computer Science in college and it was kind of like mid nineties, like boom, like late nineties, I guess. And a friend and I had an idea for an app. So because of that , this is a windows app I'm talking about. And of the two of us, I spoke English. So we coded a prototype and then we decided I should write the business plan. So I wrote the plan and we sent it out to some investors and the responses were kind of uniformly horrible. And one investor wrote back, Andy, this is, I rate every business plan on a scale of one to 10 and yours is a one. And then in case it just for good measure, he wrote in parentheses "worst", in case we thought one might be the top of his rating scale. But then he wrote this other thing that was kind of the seed of everything that came after that. He wrote not a compelling story. And I didn't pay much attention to it at first, but a few weeks later I was walking by this Barnes and Noble. I was living in Manhattan at the time and I saw this sign in the window. And the sign said: :For anyone who wants to tell a compelling story", and there was an arrow to the stack of books and the books I went inside, they turned out to be about screenwriting and it was something I knew nothing about, but I bought the books and read them cover to cover. And what I realized was that they presented a very different way of structuring the story than what I had learned like in business school. We probably did a really horrible job, but we tried to use that structure in revising our pitch. And then we sent it out to some more VCs. And the interest that we got was quite different. We started getting invited to pitch. The pitches went better and we had a term sheet, you know, an investment from some pretty good VCs, like few months later. And, you know, there were, there were some other things that happened too, along the way. But the interest that we got from this revision was just really striking to me. And I started asking, well, what of these movies stuff applies to me as a seller, whether seller of a company or product or whatever, because you know, not everything did. Most of the book was sort of useless. You know, we're not building three X screenplays in business. And so what applied, what could we use? Those became questions I'd be asking for like 25 years. After that company was acquired. And you know, the story helped there, too. I actually found myself so interested in this, that I started writing freelance articles and magazines. And I was offered a job at Time, Inc at a business magazine called Business 2.0 where I worked for about six years. And then after that I got married, make some money. And I went back to tech, first at Skype as a product manager. And then I wound up getting product marketing roles at a few startups that were acquired after a few years. And those led to CEOs kind of coming to me about how they were telling the story. And that was kind of the beginning of the work that I do now.

Josiah (05:20):

I love that. So I first became familiar with your work back in 2016, I believe when you posted this article on medium, that now has over two and a half million views called The Greatest Sales Deck I've Ever Seen. And in it, you kind of, you lay out the five elements of a brilliant sales narrative. And what I loved about it, what caught my attention was that, you know, most people start with like in a sales pitch, most people start with the problem, like the customer's problem and work from there. But instead this framework starts with the first thing is name big relevant change in the world. And so I actually, I was a product manager at the time and was working on some pitches like internally in the company. And so I used this framework and it worked. It's like, it completely changed my whole approach and it works so well. So I would love to dig into this and have you share with the audience this framework and how it works when you're, obviously when you're putting together a sales deck, but also, you know, the same things apply to marketing and sales copy and content creation.

Andy (06:26):

For me like that post, of course the title, it makes it sound like it's about a sales deck and it is about a sales deck. But what it's really about is that this is the story that the CEO and everyone on down is always telling. Yes, it got codified in this sales deck, but their content is all driven by this essentially the same story and really driven by what you call that change in the world. Everything is really driven by it. Yeah. You asked about the framework and the really the core part of it is exactly what you said, which is we're taught. I mean, I was taught in business school and other places, the basic story that the company tells that everyone's telling it has the form of you have a problem. We have a solution. Let me tell you why ours is the best solution versus the competitors. And so it kind of sets, even though it starts with supposedly your problem, it's it sort of sounds like it's customer focused. It pre devolves pretty quickly into bragging. It sets you up to be what I call the bragging doctor. So you have a pain. I have the cure. Let me tell you why our cure is better than all the other cures that people might be slinging at you. And what was really fascinating, not only about Zuora, but so Zuora is the company that authored that sales deck that is in that post. What was really interesting about what they did and also what companies like Salesforce has done since then, companies like Drift, Gong, pretty much all the category. You know, the dominators, the ones that kind of broken out of the noise is they started from a very different place. And the place as you said, this change in the world. So for Zuora, they started not with, Hey, you have a problem. You know, their software is subscription billing software. So software that companies that would be selling products through monthly subscriptions would use. They didn't start, like most of the companies would start, which would be like, Hey, your problem is that you have to repeat the bill and you have to track usership and you have to manage plans. And let me tell you how we're going to do that and why we're the best to do it. That's that wasn't the structure. The structure instead was we are now in a subscription economy. So they named this change in the world. Since then I've started to call this the new game. So they named this new game that they say, Hey, and, and they're very clear also about the old game that we came from. So the change is really old game to new games. So the old game you used to sell things, you know, meaning transactionally, someone would buy them, own them, maintain them. And now there's a new game where the consumers, businesses, buyers in general are opting to want to pay for the benefits of those things without the hassles of the ownership of those things. And starting with this shift is a totally different dynamic because when you say to someone, Hey, you have a problem. First of all, they may not know they have the problem. Second. They may know it, but feel embarrassed about it or, you know, shame or something. And third, they may know it and not be embarrassed about it, but not want to tell you because they're afraid you're going to sell them something. They're going to use it against you. And so it kind of sets up this very defensive posture for people who are listening to that kind of pitch, unless the person's like, you know, screaming in pain, screaming, and like in an emergency room, you know, I need this thing so badly, but most selling situations, especially enterprise selling and, you know, beyond the kind of early adopters is not that it's trying to create some urgency. And so this shift does that much more effectively. It's like, Hey, there's this new game. And then we're going to tell you about kind of who's winning, look at all the people who are winning. They're all playing this new game. It's a kind of, not quite FOMO, but setting up this club of winners, Hey, look, all the winners are playing the new game. They're all going to subscription. And look at the losers. Well, look, they're all still selling stuff. And that's set up essentially as the setup that power of that company, you know, from nothing to being a category king and then eventually to going public. And to this day, you know, I still see posts from their CEO and he still talks about, he doesn't talk about how great Zuora is for the most part. He talks about, wow, look at how it looks at who's winning with subscription model.

Josiah (11:23):

Oh, that's so awesome. So the next thing, the next part of it is the, you know, you mentioned in this post is teasing the promised land. Can we talk about that a bit?

Andy (11:32):

Yeah. So again, I've kind of used some different language more recently that I think kind of captures it a little better, but you know, there's this new game that we're telling people to play, which is it's worst case subscription economy. And, you know, when people play a game or, you know, really adopt the narrative, there's gotta be some goal. Like what is the kind of point of no return in a good way for happily ever after? So what's the finish line. So in Star Wars, for instance, you know, and by the way, like I said, a lot of this, those come from movies and especially the beginning of movies, I think is very educational for this purpose. In Star Wars, we learned very early on, Luke is going to have to destroy this death star thing. And if he and the band of buddies can do that, then it's going to be game over in a happy sense is going to win. And so the amble to define this as a kind of statement is really great as in my opinion, like the, what some people would call a tagline. So that the top message on the website, the message we use that kind of becomes the North Star for product and everything else. Everything we're trying to do is to get customers to that point. So with Zuora, they actually had to have had a few iterations of it. I think the first one was deliver the subscription experience. And this was something they defined, it had five pieces. I can't remember what they were, but you could deliver the subscription experience as they defined it. Then you were a winner in the subscription economy game. I think they later kind of simplified it to turn your customers into subscribers. So if you could turn all your customers into subscribers, you're a winner. And this what I was calling A Promised Land statement, and lately I've more called, like, so The Object of the New Game, the statement lays out that kind of goal state that helps the buyer and the company make decisions and kind of frames their world, frames what they're doing. Anything I made confusing in that. There's a lot there.

Josiah (13:42):

No, that's fantastic. There is a lot there, but it's so helpful. And it's so valuable to have this framework, as you're thinking through, like, we connect with the story, right? We're wired that way as human beings, right. To connect with a story. That's how we understand the world, as we tell stories about it. And so using these framework and this language and these ideas to help create shifts for people is so powerful. So Andy, I'm really curious in your own business, how one, how you've sort of applied this framework into your own sort of sales pitch for your, the work that you do, but also how content plays a role in your business.

Andy (14:26):

Content made my business possible. I could not be doing the work I'm doing today without the content that I've put out there. And without the platforms that made it possible for me to put it out there and to get it out to the people who were going to be interested in it. So it was probably around 2013. I started writing posts on LinkedIn and Medium about this stuff. So initially, you know, kind of like everybody, I'm kind of writing to nobody. You know. I had some modest following on LinkedIn, nothing on Medium, not much on Twitter and, you know, gradually people started paying attention and it was kind of, and in the early days of Medium after the first post that got a lot of attention was in 2015. It was a post about Elon Musk's talk that he gave as a keynote for the launch of the Tesla power wall. He gave this talk and it was, he was kind of being widely hailed as like the next Steve Jobs after this Talk. It was a great talk. And I saw some people like sort of presentation folks dissected, and I didn't think they really got what made it tick. And so I wrote that post and it was, that was a kind of prodo conversion of the framework that I put out in the Zuora posts, but that post got around 250,000 views. And it was the top post on medium for a few days, you know, back when that was sort of easier. And it led people from really around the world to start calling me about, Hey, I want to structure our pitch like this. And for me to start doing this kind of work, I continue to do those posts. And then of course, yeah, the greatest sales deck posts just blew up. And I would still say most of my work comes from that post, that single post, because people still do use the framework in all kinds of ways. These days, I find that Medium has been less effective for me. You know, Medium when they change their model to be more dated, it wasn't as useful for someone like me where I'm not trying to make money off my content directly, and I'm not trying to get aid for my articles. And LinkedIn really became the place that the hub for me, where most of my engagement happens. And I really enjoy, you know, LinkedIn as recently as like probably a year or so ago, you didn't see much sort of personal stuff on LinkedIn. And of course there's still is a line. It's not Facebook by any means, but there's been a wide, a really wide opening in terms of what's acceptable on LinkedIn to post. And of course I'm posting, you know, mostly stuff about the work that I do and things about this framework and how it fits in the world and stuff. But I also know a lot of posts that are like a poem, an ode to my career counselor. I did one today about a pricing lesson that I learned from my therapist and people have responded. I did posts, so I launched the podcast not too long ago, three months ago. And my mom hated the name of the podcast and she happened to be visiting when I was launching it. And so I just started to put her on camera and tell me why she didn't like the name. So then I put that video on LinkedIn and wow, my mom became like this sort of minor celebrity on LinkedIn. A minor, you know. She got a lot of attention. And now actually have every episode of my podcast, my mom intros the guests, and that turned into be like this really a fun thing that I didn't expect. And so it's, there would've been no way 10 years ago for me to take that framework that I laid out in that post and find an audience for it and then create a business around it that only is possible, you know, now.

Josiah (18:39):

Yeah, for sure. I'm really curious when you were writing that sales deck post, did you have any idea, like in your head of how big it would get, or were you just not thinking about it? Like I'm curious what was going through your head as you were putting that together?

Andy (18:54):

No, I really had no idea, you know, I thought it might do well, like kind of like the Elon Musk one, but it really went to a different level and I did not expect it. No.

Josiah (19:06):

That's awesome. So I'm curious to know about, or to hear about your podcast and why you started it and what your vision for it is.

Andy (19:15):

The podcast is called The Bigger Narrative and every episode is a CEO, most of whom I've worked with so far though, that's about the change. We're getting to have enough episodes soon that I'll be talking with CEOs who I haven't worked with, but who I think are really kind of good at this and have a lot to say. And so each one is where we're talking about their strategic narrative, how they use that narrative, that's kind of old game, new game narrative in their leadership. So in many cases it's about selling or category creation, but in a lot of cases too, it's about recruiting or the most recent one I did is about getting the leadership team aligned on attacking some new opportunity and vision. And the main reason I started it honestly was because I've worked now with teams, I've done this work full-time for five years. And I wanted to go back to some of the folks I had worked with early on and get a sense, like what happened, you know, like has this story, what has it done? And I was a little shy to do it. I kind of thought like, Hey, they're going to call me. Right? Like I had this belief that, Hey, if things are going really well, they're going to call me and tell me, you know, they'll just think to do that. And in some cases they did, but in some cases I hadn't heard from them for a while. And so it was kind of forcing myself to go back and it was kind of an excuse to do it. And what I found right from the beginning was that the narrative had this long-term effects in many cases that I just had no idea about. And it was really gratifying to hear these. And, and from what I've heard from folks, it's been educational for people who are, or helpful for people who are trying to think this through for themselves of how they structure their own or that kind of stuff.

Josiah (21:13):

Yeah, absolutely. So, Andy of this has been so great. I really appreciate you coming on the show today, before we hop off here, can you share with everyone where they can find you online?

Andy (21:23):

Yeah, probably best place to find me online is LinkedIn, Andy Raskin. That's where I'm always posting about this stuff. And if you're interested in the podcast again, it's called The Bigger Narrative and you get, you know, wherever you get your podcasts, you know, the deal.

Josiah (21:37):

Yeah, definitely go check out that podcast. Once again, thanks so much, Andy, for being on the show and everybody out there listening, go be a hero.

Josiah (21:45):

Hey everyone, thank you for listening to the Content Heroes podcast. I just wanted to take a second and let you know that we have some amazing guests planned for the coming weeks. So if you haven't already go ahead and hit subscribe so you can make sure to catch every episode. And if you enjoyed today's episode, go ahead and leave a five-star review to help make it easier for other content creators to find and enjoy the show. Lastly, I'd like to invite you to join our Content Heroes Facebook community, where you can connect with other online content creators to share, learn, grow, and have fun. To join the group, just visit Once again, that is

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