How to Raise Millions in SaaS With Storytelling – Andy Raskin @Strategic Narrative

Todd (00:01.054)

you bigger because I hate looking at myself on these podcasts. Let's make no wrong one let's make you bigger. Okay cool. Hey Andy welcome to the show. Yeah pleasure is all mine. Well maybe we can start off with a somewhat philosophical question. Who is Andy Raskin? And feel free to answer that however you like.

Andy Raskin (00:11.034)

Thanks Todd.

Andy Raskin (00:21.042)

Hmm well If I tried to explain my like career path it would it would just be I don't think we'd have time in this podcast Like to try to make sense of it, but for about the last ten years I've been working with CEOs on what I call strategic narrative, which is This one story that they're telling about the world about their their buyer that powers success

sales, marketing, fundraising, product development, becomes the North Star for that, recruiting, everything. So I really look at this story as, like I said, like strategic narrative, that it is the strategy of the company, which is of course why it is a CEO, it is a CEO job to do that. And I typically work with B2B

Andy Raskin (01:20.170)

kind of enterprise SaaS companies that have large sales forces But I've written some posts over the years that Others also tell me have been really valuable for them around the sort of same concepts

Todd (01:35.182)

Yeah, got it, thank you. And what is the kind of the pain point that they're experiencing when they bring you on board? Why do people call typically bring you on board?

Andy Raskin (01:45.546)

You know, I just made a LinkedIn post where I listed out So every time a CEO contacts me, I you know, I have it We have a conversation and if it gets to the point of me, you know sending out a proposal like an SRW I'll write down like what did they say is they're looking for, you know, and and I think there's a few variations on it One is this I think the biggest thing is like alignment like hey we're

We're growing. Early on, one CEO said this, it was kind of like brute force of the founders. We were successful, but it was sort of all over. And now we're getting bigger, and we're gonna have to all speak with one voice, all sing the same tune. And I want one story that's gonna guide all of that. I'd say that's really the main thing.

Andy Raskin (02:44.306)

But it happens at different stages. Sometimes it's, you know, they're going from like, I don't know, Series A to around Series B, sort of like that stage. There's sometimes there's a, it happens later. So some companies I've worked with where they're either building or acquiring lots of new products. So they've had success in one area and they're starting to branch out into other stuff.

Todd (02:52.726)

Yeah.

Andy Raskin (03:09.446)

hey, we've kind of spoken with this one story, it's worked well, but now we're gonna need this bigger one that's gonna kind of make sense of why we have this bigger offering and help us sell that, all the rest. Some people think about it as, I wanna create a category. I don't usually use that category language, but, well, I do because just people use it, but they'll say, hey, we kind of came up with a category name we like, like these three words that we...

thought, you know, we're gonna kind of just convey to the world, like, why we're so great and different. And, I don't know, just those three words aren't working. Like, we need a story around it. And even, you know, the category people, like the Playbigger people and stuff, will say, like, hey, you know, the core part of this category thing is this story, namely about a shift in the world. And so sometimes it's that. And

And I'd say maybe the last thing is where they are... Actually, you know what? Those are the biggies. Maybe I'll just stop there. Yeah.

Todd (04:23.274)

Yeah, yeah, gotcha. No problem, you can expand on that later. Listen, I mean, you have a whole framework for how to approach a strategic narrative and that's kind of the meat of this podcast episode, so we're definitely going to go deep on that. But you also talk about superiority claims and this is kind of an alternative to superiority claims. Maybe you can just kind of expand on that point and explain what you mean.

Andy Raskin (04:46.862)

 

I think that approach, like I said, it comes from an age when products were very simple. They didn't change much. Cans of soup on the shelf in a supermarket, cars in a dealership, even software back then sold in shrink-wrapped boxes that sit on a shelf and maybe get updated once a year. But now, especially in the SaaS, we're in a world where the product is changing.

literally minute by minute sometimes. The markets are very, very crowded. So buyers being bombarded by these claims. And, you know, can you even create the identity of a company on product claims when the product itself is so dynamic and the landscape is so dynamic? And so what I started seeing...

Andy Raskin (06:42.922)

Was that there was this other approach I started seeing it over like 20 years. Well, maybe 15 years Until I sort of started codifying it That there was this other approach that I called strategic narrative and That approach is That the starting point is not you have a problem. I have the solution The starting point is hey

There's been a big change in the world, in your world as a buyer.

Todd (07:13.514)

Yeah. Yeah. Well, maybe, maybe we can, um, and just before we jump in, because that's actually, we want to talk about is because you wrote a, um, a blog article on medium, which was the greatest sales deck I've ever seen. And that kind of outlines the, um, yeah, the different, um, parts to this framework, if we, if we want to call it a framework, but just to, just to kind of zoom out for a second. And I think, make, correct me if I'm wrong, the way, the way, when I was researching this podcast and I was thinking about

you know, humans, it's intrinsically in our DNA to tell stories, right? That's how we've been able to evolve from, you know, a group of 150, you know, monkeys into huge groups of people. And in the book Sapiens, Yuvel Nohari said, "'You could never convince a monkey to give you a banana by promising limitless bananas after death in monkey heaven.'" I think basically what I'm trying to make this point here is that, yeah, stories are in our DNA. It's what the connective tissue that holds everything together. Do you feel like you've just...

taken the power of storytelling and just kind of overlaid it and applied it to a business concept and that's potentially why it's so impactful.

Andy Raskin (08:16.358)

Yeah, although, you know, the storytelling thing, like, you know, it comes from the world of movies. And, you know, we're not building a three act screenplay here. So what applies, what doesn't apply. I actually, it's interesting you say that. So the way I really got into this was I started as a software developer myself and.

Andy Raskin (08:42.970)

A friend and I had an idea for an app. This was like.com years, so like Windows app. So we coded it, a little prototype, we got some users. We were already living in the Bay Area. We were like, okay, maybe we could get some investment. We decided, of the two of us, I spoke English, so I should, fluently, so I should write the plan. So I wrote a plan, we sent it to some VCs, and the reaction was really bad. And...

One of them wrote back like, Andy, listen, I rate every plan I get on a scale of 1 to 10, and yours is a 1. And then he wrote, in parentheses, worst, in case we thought maybe 1 might be the top of his rating scale. But then he wrote in the margin, he wrote, not a compelling story. And I didn't really pay much attention to that, you know, we were just sort of, sort of like really down about the rejections.

But a few weeks later, I was walking by this Barnes and Noble in Manhattan, where I lived, and actually, I guess I still lived in Manhattan at the time, and there was a sign in the window, and it said, for anyone who wants to tell a compelling story. And, okay, that was me. And there was an arrow pointing to these books that turned out to be screenwriting books. And I read these books, and, you know, they suggested a very different way of...

Structuring a pitch. Well, first of all just this idea that a movie is a pitch I kind of think I got from these things like what is Star Wars a pitch for it's a pitch for like Ultimately like trust the force like be good, you know Have friends and be nice to people But like I said I was do I was making I was pitching a Business in a very short amount of time with no graphics or anything like what?

applied, what didn't apply. I started asking those questions and what I came to when I saw that Zora deck that you referred to, and that's the deck in that post, the greatest sales deck I've ever seen, that's where it all really clicked for me. I had been kind of working on it for years on posting about it already, but that's where it all really clicked into place for me.

Todd (10:58.742)

Maybe you can explain the story then, the genesis of that deck. How did it come about? Why did you write that article? Yeah, what's the backstory?

Andy Raskin (11:07.234)

Well, why I wrote it is because, like I said, I'd been interested, I'd been thinking about these questions for a long time, and it really helped me articulate, like you said, a framework for how I would think about this, how I was thinking about it, how I wanted to think about it. There are really five pieces to it. The first, you know, Zora...

Andy Raskin (11:37.594)

So Zora comes out of Salesforce, and the founder of Zora, Tien Tsuo was like number 11 at Salesforce. And if you look at their pitches, it wasn't, hey, you have a problem where you have to repeat the bill. So Zora called themselves a subscription billing platform.

And there were already a bunch of them. And they were basically saying that, like that arrogant doctor, hey, you have a problem, you have to like, most billing software is only gonna send one bill, and how are you gonna repeat the bill, and how are you gonna do that? And Zwera starts in a fundamentally different place. They say, hey, we now live in a subscription economy. They say, hey, the world has changed. Used to be transactions, like we would buy things one-off.

Now we're going to be, we're living in this new world already, not its future, but already where we're subscribing to things. And this was early. This was like, I think, like 2014-15 they started doing this. You know, we have Netflix, we have Uber, which is sort of subscription-like, you know, instead of versus like buying a car. But, not everything is transactional, even now, not everything is transactional. Probably the minority of things are subscription, but

Andy Raskin (13:03.610)

They pose this very absolute shift in the world, and then the whole rest of the pitch is like, well, how are we going to deal with this? The second piece of it is...

Todd (13:14.830)

Sorry to interrupt Andy, because I think this is super interesting. I guess what that does is it, instead of, even speaking of ourselves, even in my own pitch presentations, I do think we indeed start with the problem. And I'm sure a lot of people listening to this will do exactly the same thing. So instead of talking about the problem and then your solution and why yours is superior, I guess what you're doing is you're kind of saying, well, the world has changed. You're already behind. So you've kind of, you've set the expectation and they're already, oh.

you know, shit, we're behind. I guess that's important part of this.

Andy Raskin (13:46.275)

Yeah.

Andy Raskin (13:48.934)

Yeah, it's a because and you're getting to the second piece of it, which is what I call really naming the stakes because and again, there's very illustrative thing that happens in Star Wars and happens in almost every movie. When

Todd (13:59.234)

Mm-hmm.

Andy Raskin (14:11.778)

So sorry for the Star Wars spoilers for anyone who hasn't seen it. It's been like 40 years, so hopefully that's not a big deal. If you haven't seen it, you're probably not seeing it. But in the first one, the first one that came out, A New Hope, Luke has been bellyaching for the first 15 minutes. Like, I want to get into space. I want to have adventures. I want to be a pilot. So Obi-Wan shows up. He's like, hey, I got this mission for us. Let's go into space. I'll teach you to be a pilot, all this stuff. What does Luke say? He says,

Mmm, you know what? It's getting kind of late. I gotta go home Sorry can't get involved who does this sound like Todd

Todd (14:54.666)

It sounds like a, yeah, it sounds like a prospects.

Andy Raskin (14:57.198)

the reluctant prospect, right? And people say like, you should make the pitch emotional or make the story or whatever. And I always found that weird because like, what does that even mean? Like literally, how do we define that? And here's how I define it, is it's not emotional if the person does not see stakes for themselves. So Luke in that situation, he's saying,

Andy Raskin (15:25.614)

He's saying, I'm not going to do this, because he basically sees the future as okay. You know, maybe there will be ups and downs, but you know, he doesn't see it being too bad. What happens, and then what does George Lucas do to create the stakes? He, the Empire kills, again, sorry for the spoilers, the Empire kills Luke's aunt and uncle. Now, Luke's kind of understands, like, well, probably they're coming for him. And as an audience, we understand, like, well, probably he's going to be dead.

Andy Raskin (15:56.603)

Then Obi-Wan has this other, laying out this other path where that he might thrive and win. And so now the future is different. It's bifurcated into a likely, like you said, you're already behind and you're going to probably be dead. Or this other path where, you know, well, look, look who's thriving. So what Zora did is they said, hey listen,

there's been kind of this accelerated die-off of companies. They show this stat about how like the Fortune 500 companies are sort of around for shorter and shorter time, but look who's thriving. Oh, it's the companies that are adopting like subscription and subscription-like models, like, you know, all these examples. And...

This is what it's setting up. It's exactly the same thing, and it is kind of what you're saying. Like, hey, we don't want to say, like, you're behind. Like, it's just like an insult, right? Like, we don't want to trigger that. So it's a little bit sensitive. I've written about this a little bit. Sometimes we want to say, like, hey, I was in that situation, too. You know, we were there, too, and this is what happened to us. So there's a little bit of kind of like empathy there.

And we're not just saying, hey, you're an idiot because you haven't shifted. But if we do it properly, I think it really works well. And the other thing that it's super great for is discovery. So usually discovery is, hey, I'm gonna ask you questions about your pain. But if we're talking, hey, there's a shift in the world, we're seeing this happen, how's this playing out for you?

Todd (17:23.523)

Mm-hmm.

Andy Raskin (17:35.162)

This is, we can start hearing some real gold around this.

Todd (17:39.394)

Yeah, that's super interesting. So number one is name a big relevant change in the world. Then we have to create stakes, so show there'll be winners and losers. And then the third step is to tease the promised land.

Andy Raskin (17:50.934)

Yeah, so I've actually updated the way I talk about this. And when I say tease the promise line, it used to be, people would basically just sort of say like, oh, so I just have to describe how great it's gonna be once they're gonna be making a lot of money. And it was just too vague and stuff. What I now call it is the buyer mission statement. So we're gonna put out, so in this new world,

Andy Raskin (18:18.606)

The way I talk about the shift in the world now too has evolved. I call it the shift from an old game to a new game. So in the Zora case, the old game was, you know, transactions, the rules of that game are you sell something and someone buys it and you sort of have, that's it. Maybe you sell them again, something, but maybe not. And the game changed to basically how do you keep this person on for life. And...

That game has a different kind of object of the game. You know, every game, every game you board, game you play as an object of the game. What is the object of this new game that's different? So, for Zora, they went through a bunch of iterations. One iteration was very simply, turn customers into subscribers, you know.

Andy Raskin (19:10.042)

Very simple, very comes right from it, right? Doesn't have to, and I like this to be simple. I like it also to be in this second person command form so that it acts as a rallying cry. What I really think we're doing here with the strategic narrative is turning the company and the product or kind of enveloping them all in a movement. Category people may say as a category. I like thinking about it as a movement because

Andy Raskin (19:38.650)

It really is what it is. Like we're championing this shift, this change, not just a kind of like new type of thing. The new type of thing will follow, right? So, you know, if you look at Airbnb when they were earlier, early on, if you went to their website, it said, live there. This live there to me is a buyer mission statement. And the buyer mission statement often works really well as that

like top line of the website because it explains all the differentiation, not in terms of a claim of superiority, but in terms of a different goal state for the buyer. So, you know, Airbnb not saying like, oh, we're cheaper than hotels or, I mean, I don't know if they are, but...

——————

Andy Raskin (20:29.906)

Or we're more convenient or whatever. They're saying hey There's this other goal state that we're everything we do is designed to get you there So this third piece I used to call the promised land message or tease the promised land. That's fine if that works for you Lately I always call so name the object of the new game or what I call this buyer mission statement

Todd (20:49.598)

Yeah. Gotcha. And then I guess say another huge mistake that the companies make, particularly in SaaS as well as they talk about all the bells and whistles and the features themselves. Whereas your fourth step is to introduce features as, I don't get, I apologize if you've changed the wording on this, but introduce the features as magic gifts for overcoming obstacles to the promised land. So you've kind of communicated the promised land in this different state, but now you're talking about your features and your product in a way that essentially helps them get there.

Andy Raskin (21:18.170)

Yeah, I mean, there's this knock on talking about speeds and feeds. And speeds and feeds are very, very important. By this, I basically mean features, right? And especially when we're in a very technical product, these things really matter to people. What we've done, though,

by first setting up these first three pieces, is we created a context on why these features are gonna be life and death. So the fourth piece is, before we get to the magic gifts and the features, we're saying, okay, you wanna live there? Well, there's gonna be some obstacles to living there. Airbnb doesn't do this because they're not selling in a sort of enterprise situation, but...

just imagine they were. Say, well, you know, how are you going to be... Let's take actually this Warrant example instead. So you want to turn customers into subscribers. And let's say they're pitching like Ford, which is actually the company they were pitching in the sales deck that I got. So now say, okay, you want to turn customers into subscribers. Well, in this new world, like how are you going to know...

Andy Raskin (22:42.490)

the preferences over time of the people you're going to, because you want to have this always-on relationship with them. To make this work, you're going to have to track those things. How are you going to have different pricing tiers and change those often, and communicate change, all this stuff. There's all these obstacles, and you can really think about this as...

the movie situation because we've been talking about that, you know, in Star Wars or Lord of the Rings, whatever you want to call it, the character can't just go and accomplish their mission. Like there's things in the way. And same thing here, like if they could, if turning customers into subscribers was just really easy, like there's no reason for Zwar to be there. So it must be hard. So we're gonna start with...

Andy Raskin (23:38.570)

Often I do it into just like a bunch of how will you questions like how are you gonna know their preferences? How are you gonna? Track their lifetime value and and you know and and segment the highest test I can do all these things right and then of course this sets up sets us up for now talking about all these These features as this sets up the the features that is where offers as kind of like the lightsaber you know and and the

Jedi mind tricks that Obi-Wan is going to teach Luke. These are what the screenwriting people call the magic gifts that the main character gets. And now they're not just solutions to disembodied problems. I mean, because you could think of it as like, oh, yeah, that's just problem and solution. The thing is what we've set it up as, you're solving these problems.

Andy Raskin (24:33.706)

in order to reach a goal state that has life and death consequences for the company. And so setting up that context around it is, I think, where the magic happens.

Todd (24:39.170)

Yeah.

Todd (24:49.930)

Yeah, it's super interesting. And then I guess the final step, which I guess is really critical, is you then have to provide some evidence or proof that you've done this before and you can guide them on that process. You can help them with those obstacles and you can help them achieve that state.

Andy Raskin (25:06.382)

Yeah, I mean, we clearly want to show that there's some reason we're not just making this up. And then, you know, there's many ways to do that. And how you do that probably also depends on the stage of your company. So if you're, you know, a very mature company, you probably have lots of success stories you can talk to.

You can probably even target them by different, you know, what industry they're in or what segment they are and sort of pull a success story that matches them. You're just starting out. You may have like close to nothing like that. And the only thing you can talk about is like, I don't know, our team or, you know, like an investor pitch or, you know, I don't know, some prototype we made and some traction it got, you know, we'll take what we can get. But whatever we can, you know, yeah, really nice to have that.

Todd (26:02.542)

So this, I can imagine this being to guide a company through this framework and this process, because you work specifically with CEOs, right? So, and in big companies, you work with some really, really big, well-known SaaS companies. I can imagine to implement this framework to get everybody on board, to get everybody aligned must be really, really challenging. Now, not expecting you to give away any secret source here, but how do you kind of...

go about that process? And I know that's probably a really, really big question with a huge answer, but you know, like what are some of the steps you have to go through?

Andy Raskin (26:33.722)

Yeah. Yeah. Well, I think on LinkedIn, I've given away pretty much all the secret sauce. So I don't know if there's any dips of it left, but I'll share maybe a few things. You said I work with CEOs and that is true. I do see the CEO as, like I said earlier, like if this is really, if you really do believe that this story

Todd (26:45.727)

Awesome.

Andy Raskin (27:03.506)

is the strategy of the company? How can this be delegated to marketing? How can this be anything other than a CEO job? And that said, the CEO has a huge task in aligning the team around it, getting people to buy in. And so to balance that,

I ask the CEO to create a small team, I call it strategic narrative team, which is themselves and up to four other people. And typically these are heads of sales, marketing, product. So marketing does have a big role, not the leadership role. And this is controversial. I just got an email from a very well-known marketer. He's like, hey, think.

thinking of doing a new, doing a street narrative, really want to talk to you. And I sent an email back like, hey, great, but the CEO plays this sort of central leadership role. So I'd really, I'd ask that your CEO join the call and maybe read a couple of my posts beforehand. That was yesterday, I haven't heard back. So, that's what it was.

Todd (28:18.954)

Can I sorry cuz I'm no super I'm really super intrigued have it Did you start off not? Yeah with a mark ahead of marketing and then you look quickly learned that it had to be the CEO or do you always have that? stance

Andy Raskin (28:30.030)

Great question. In the first few years that I did this, it was a mixed, it was mixed. Like I basically would just, I would be open to working with whoever contacted me. Sometimes it was the CEO, sometimes it was the marketing leader, sometimes it was other, like someone else, customer, head of customer success, I think, was early on. And I looked back.

at a certain, after a few years, I was like, which were the ones here that were like the really successful ones where I, like it took hold and all the rest. And every time it was so clear. It was where the CEO was the leader. And eventually I decided to just insist on that.

Todd (29:20.682)

So you've worked with, correct me if I'm wrong, more than 100 companies implementing this framework. You must have learnt a heck of a lot. What are some of the, I think you actually wrote a blog article about this somewhere, but what are some of the key lessons you've learnt with working with 100 companies in this area?

Andy Raskin (29:39.794)

Hmm well One of the lessons that I think maybe is like the biggest one it's kind of we've been we've been talking about it a little bit but that Conversations about messaging or really conversations about strategy That You know, I think we tend to think of strategy as this very I Don't know like academic thing

Andy Raskin (30:10.222)

and that to, you know, if you ask different people in the company, well, how do you define strategy? It's kind of like that thing of the people, is it the blind man with the elephant? Like, there's like different answers based on where they are in the company. And I apologize if that metaphor is now offensive, which I'm realizing maybe it could be. But in any case, the...

I think you get the idea. You know, if you ask people who have been to business school, they say, oh, you have to define Porter's Five Forces, which I don't know if you know, it's like there was this famous book about strategy, and you do this presentation where you write about the, you figure out your stance on the Five Forces and how they apply to you. If you talk to people in marketing, it'll be some internal messaging.

positioning document that is supposed to be the source of truth for everything. If you talk to, I don't know, like leadership kind of people, it's like we have a mission statement and a vision statement. That's the strat, right? And I thought really hard about this when I started doing this work. Like what is the instrument that we're gonna use to...

Andy Raskin (31:38.394)

find that, like, how does the strategic narrative relate to all of those things? And where I came to is that it, it, it supplants all of those things, that it is those things. Like, what's the mission of the company? It's that buyer mission statement.

Todd (31:43.542)

Yeah. Yeah.

Andy Raskin (32:02.094)

If we want to be a customer focused, what is the goal state we want to put out there for the buyer? Isn't that the mission of the company? How we talk about the company, all the messaging should be there. The other thing I decided was that I really decided... So when I started working on this, my deliverable to the company would basically be a chart with those five...

Andy Raskin (32:30.918)

elements defined. Like, okay, what is the change? This was... And that was based on what I had seen marketing consultants kind of do in my career. They'd leave behind something. They might not do the same framework, but they'd leave behind some sort of messaging house, they would call it a messaging map, where it's like, okay, here's our top message, here's the pillar messages, these fragments of messages.

Andy Raskin (32:58.090)

I found in my career that that would break down, and I found it in my own work, because the idea was that people are going to go back to this thing and pull messages from it, and people didn't go back, especially when they were outside of marketing and it was kept in marketing. The other thing was, even if they did, I think it's very hard for most people to like string together these fragments into something compelling that's going to work.

Andy Raskin (33:27.598)

I thought really hard, like what would work better? And I came to the sales deck. And this also took a couple of years for me to learn. Like the sales deck as the core strategic and narrative asset. And this is very controversial. Like most people see the sales deck as an output of some, I don't know, fundamental strategic document thing that lives somewhere else.

Andy Raskin (33:53.038)

I'm saying no, let's make that let's make the sales deck which is how we talk let's make that the fundamental thing and everything goes off that and You know still people have to kind of come back to it But I think we have a much better shot because hey, it's gonna get used in the most important channel for the company all the time

Todd (34:16.586)

Yeah, so this framework essentially supersedes vision, mission, positioning, marketing, messaging. So if that's the case, and I guess that's the big challenge for you, isn't it? Because you're already coming into mature businesses where they have segmented teams, they have robust leadership with strong opinions, and then you're coming in and saying, well, we actually need something that supersedes all these things and interconnects all of them. That must be really challenging. So from like a...

In an ideal world, when would you approach this? Is it based on what I've just said? Is it from day dot? You would define this from day one and everything supersedes, cascades down from that. Would that be the case?

Andy Raskin (35:00.310)

Well, I would say you're right. That is a hard sell. And it's probably why, like, you know, the majority of CEOs are not going to ever hire me. Right? Like, they're going to delegate. They're going to have a mission vision statement. They're going to delegate this thing to marketing, whatever. There are some, though, there's some small, big enough small subset for me to like sort of live, where this resonates with them.

And I think, like I said, there are certain points in the journey of the company where they'll resonate. And that was it. This was, you asked about learnings. This was another huge learning for me. That there would be that this narrative thing became super critical at later stages of the company. When I was first starting, like I said, I got into this because I was pitching a startup.

that I had no money for initially. So once these screenwriting books kind of helped me, and actually, I don't know if I mentioned, we redid our plan and we sent it out again, and after a few months we had a term sheet, and it clearly helped us. And it helped me as a CEO, but I had no money to pay a consultant. So for 15 years I didn't...

I wanted to kind of do this work, but I was like, well, there's going to be no money in it. I mean, actually, I had an in-person class in San Francisco for a while that a lot of folks would come to, and I love it. It was like $100. I wasn't making money off it. I just really enjoy getting to interact with people at that stage. But what happened was, early on, I started working with a CEO of a...

a series C company who contacted me through a CEO who knew me, who knew about my work, and he's saying, hey, listen, I need help with blah, blah, blah, blah. And it's basically he needs this narrative thing. And I wound up, I didn't have the guts to say, hey, why don't you just hire me to do that because that wasn't a thing. So I said, why don't you hire me to be an interim CMO?

And he did. This was a company called 500 Friends, which was a loyalty platform for e-commerce brands. And the CEO, Justin Yoshimura, after about nine months, we worked together. The company got acquired by a really big marketing agency, eventually by Dentsu Japan. And I asked Justin, like,

Was it worth hiring me? And he said, he said, yes. And he's a very straight shooter. So he would have said, no. So I said, well, could you sum it up? And he's like, you got our story straight. And I said, well, if I had said just at the beginning, like, I'm gonna get your story straight and here's how much I'm gonna charge you and equity, would you have done it? And he said, yes. And this really surprised me. And I said, I don't believe you. And he...

That was a YC company. He sent a note out to the YC Founders List, Y Combinator Founders List, and kind of said, hey, this is what we did, and a whole bunch of founders. One of the first was Spencer Skates of Amplitude. Said, hey, we're looking for this. They were a little early on, but what I learned was that this was going to continue to be an issue, and

Andy Raskin (38:43.830)

I don't ever pitch it. I don't ever like try to convince anybody. What happens, I think, is CEOs get to this place where, hey, having the mission, having the vision, having the messaging doc, the category name, like it's somehow not enough. And they're looking for something to tie it all together. And somehow what I said resonates with them.

Todd (39:08.374)

Yeah, just on the kind of the output, maybe some successful examples of, well, a good example of a company that you've worked with, how has that kind of impacted them? What has been kind of the net positive after you've worked with them? What have they reported back to you? So, I think that's a good question. I think that's a good question.

Andy Raskin (39:26.094)

Well, it's almost, I think, impossible to tease out. Like, what was the effect of this? You know? I mean, aside from sort of some minor examples, like maybe A-B testing, is it even possible to tease out almost anything you do? We like to say, oh, they did this, and they were successful. And that correlation.

Todd (39:34.335)

Yeah.

Andy Raskin (39:53.126)

making the causation argument is usually pretty weak. So I don't think I'll try to do it. But there have been a couple where... So a couple of the sort of really interesting ones. Well, Gong was a really interesting one. So I worked with the Gong team. We did this work. They, you know, this whole idea about like the old game opinions, new game reality, I think they would agree comes out of that work.

Andy Raskin (40:24.010)

And you know, when Amit Bendhoff, the CEO, contacted me at first, he was like, listen, I mean, they were already like a Series B company. I think this is about 2018. He's like, look, Andy, we're going to be big. That's already kind of clear. What I don't know is how big. And I think that this narrative, if we get it right, will be a multiplier on our growth.

Andy Raskin (40:51.846)

How much of a multiplier was that? It's really hard to know. And I'm not going to take credit for that. I mean, this story, it's like that company made it the focus of everything they do. Like, I mean, only once, like it's not just our message to the world, it's also in marketing or sales, it's also the North Star for our product roadmap. Like, you know.

We get requests for features all the time that basically turn out to be about recording opinions, and we're going to say no to all of them. Another, more commonly, what I hear from the CEOs is, hey, we're getting everyone aligned around one voice, and that's letting us talk to people.

Todd (41:26.635)

Yes.

Andy Raskin (41:49.442)

in a more compelling way. I recently worked with a company called 360 Learning. So this is a training platform, that's corporate training platform, that's really big. They raised like 250 million, something like that. And for a while, they were talking about themselves as a collaborative learning platform. This was like their category name. But the CEO kind of comes to me and said, listen,

I'm talking about this, I say collaborative learning, but they're like, you know, it sort of like goes out, it comes in. We need a story to make it compelling. And so we came up with this story about, you know, the old world was learning in a corporation was like very top-down, kind of like created by some learning manager or something. And in the new world, if you look at the winning companies, like who's winning?

like Google and Tesla, they have this culture that's where they create internal experts who train others. And the idea is you're going to create this culture of learning internally. And so we came up with this buyer mission statement of upskill from within. And this, again, it's differentiating not by saying, hey, our...

our platform is collaborative, but by saying, hey, there's a different goal state we wanna put out there for you versus what every other training platform is talking about. And Nick Hernandez, who's the CEO, he tells me that now when he, he's frequently pitching CEO to CEO, like it's just like gold in terms of getting that CEO to then introduce to the learning team, which.

you know, is the actual buyer.

Todd (43:47.146)

Yeah, so obviously, you know, a lot of people listening to this won't be able to afford someone like yourself Andy, I have no clue how much you charge, but I'm guessing that's the case and they'll probably want to, you know, maybe think about this problem and maybe how they could potentially overcome it. If someone was to, you know, be inspired by, you know, what we spoke about today and they were thinking about, you know, how they could potentially address this problem, would you have any advice for them? Is there kind of a...

some place you can point them in terms of, I guess obviously they can follow your own content, which is super useful, but is there anything else you can provide to those people that perhaps wanna tackle this problem themselves?

Andy Raskin (44:25.050)

Yeah, so there's, like you said, I talk about almost every day on LinkedIn, I'm posting something that I learned in interactions with CEOs or teams around this work. I also collected the article that you mentioned and a bunch of others cover various different facets of this stuff on Medium.

So if you go to medium.com slash at Raskin, that has all of those posts. It's kind of like a little tutorial on how to approach a bunch of the different aspects of this thing if you read them all together.

Todd (45:10.482)

Thank you. Just to you kind of did touch on this a little bit you know just in terms of the alignment I think it was your third you know learning I think you said alignment is is really really hard and it sounds like just in the sense of having the CEO be the the leader of this project in of itself I'm sure is incredibly helpful for getting alignment but once you've got those I think four or five people in that room and I'm sure there's a lot of debates and disagreement healthy disagreement

Todd (45:40.034)

How do you go about navigating that and getting everybody to a consensus? Do you have any tips on that?

Andy Raskin (45:48.987)

So this is some secret sauce, not that it's secret, but it's just like a lot to explain. But one thing, maybe I'll give you some sense of it. So when I started that company a long time ago, we ran into a place where we were having a really hard time executing. And one of the VCs introduced me to a management consultant named Howard Goldman. And I...

Todd (45:52.898)

That's what we want.

Andy Raskin (46:14.858)

I introduced Howard to my co- I talked to Howard and Howard's whole approach was how to run a meeting so that you get the different opinions and you kind of come up with a decision and move forward and It sounds like such a simple thing, but it was in a way more valuable than anything. I learned in business school. I

Andy Raskin (46:39.466)

When Howard told me this, I said, I think that can really help us. I told my co-founder, who's Japanese, his name is Zen, about it. Zen met Howard and was like, yeah, this is bullshit. Um, but I overruled Zen and we brought in Howard and he helped us so much. That and Zen became such a, it was so, so impressed. Zen eventually became like Howard's disciple and created this and went back to Japan and like created like the Howard.

multi-level marketing of consultants, of meetings consultants. But I got a lot from Howard in terms of how to run a meeting. And I used a lot of that stuff. And some of the things are, you know, I'll ask, I'll like present the first piece of the strategic narrative, like this shift in the world, old game, new game.

I'll show a bunch of examples, Gong, Zora, Salesforce, I see as kind of the original one, like used to be software, now it's the cloud, that was a real archetypal version of this. And then I'll ask a question, like, what is it for you? And one thing I do is I have them write it down. So I have them write down, it goes,

Free for all, like that just takes time and there's a lot of prejudices of who talks a lot. So write it down. I learned this from Howard. And then I go around the room and have everybody read it. One by one. And everybody's really... One person gets the floor and everybody's really focused on them. Which is actually better than like some people like post it on the wall or post it in a group chat or group doc.

Andy Raskin (48:32.562)

There's something about having the floor and having people listen to you. Feel heard, right? I do a bunch of rounds of this. And then the CEO, and when you can imagine, we come out with like boards and boards of notes and ideas. And then the CEO and I go off one-on-one together for like a week, and we create a first draft of this thing. And then we come back to the team and we say,

Andy Raskin (49:01.706)

here's, I have the CEO present it. And I ask them two questions, what's working and what's not working? And I also, I tell them ahead of time, like this is gonna be the low point, this second session where the CEO, this is gonna be the low point of our work together. Because in that first session, you're gonna be giving like gold ideas to the CEO, right? But there's gonna be too many of them. So to come up with something sort of like clean,

and powerful or have a chance at being so, the CEO and I are gonna have to throw out almost everything and you're gonna be pissed. And it's funny, like, I just did a project, I just wrapped up one, I wrote about this on LinkedIn, where this woman, she was a CFO, and she was part of the team, part of this small team. CFO is unusual, but in this case, it made a lot of sense because their product was a financial product. And she said, you know, you told us,

It was going to be a low point. It's like, I love where we got to. You told us that second session was going to be a low point. Maybe you should have drilled it home a little bit more. You know? I was like, what could I have done? You know? But this airing of the complaints, like what's not working, and also, but also having some what's working, so we can have a little bit of positivity. I also learned this from Howard. And...

Andy Raskin (50:32.070)

And then the CEO and I go back again and usually when we come back The team is starting to feel pretty good about where it is. So and then there's still a lot of work to do but that's that's My base, you know in a nutshell my approach to this alignment thing and it's hard. I mean I have a There's always one person

I who I've learned is always there's one person is the naysayer who's like Often it's a co-founder. I don't know why well, I have some theories about why it is who's not the CEO but that you know and This naysayer I found plays a very important role like there's sort of you know Keeping it in on track and making it sure it doesn't get too bullshitty But at the same time there are real challenge around the alignment

I have a career coach, I write about her on LinkedIn, who's kind of like my part therapist for dealing with these situations because they can get very, very emotional. Another learning that this work is incredibly emotional for people who are in it.

Todd (51:43.198)

Okay, just just for my own fun now I have a couple of closing questions. What is the you don't have to have to name the company but is there a one that's gone completely sideways or one that not completely sideways but one that's been very heated and challenging that you had to overcome?

Andy Raskin (52:01.914)

Yeah, so the company that I... maybe because it's fresh in my mind, this one that I just recently worked at where the CFO said, hey, I wish you could have drilled it in there. What actually happened was they were so disillusioned after that second session that the co-founder

Andy Raskin (52:30.738)

actually called a timeout to the whole engagement. He's like, you know what, I don't know if we should, I don't even know if we should be doing this. Maybe we're not at the right stage. Maybe, you know, all this stuff. And okay. And the CEO and I had a lot of, had some, you know, some deep talks about this. And his conviction though was, you know, so actually,

So we decided, let's take a hiatus. And we did a hiatus. This never happened before. And I was really, I was like, no way we recover from this. Like, because momentum is really, especially when you're in this like dark place, right? Like if you're, if that's, you know, gonna be hard to recover. And the CEO went back to the team and they had a bunch of discussions and...

Andy Raskin (53:27.918)

What they came to was they, I don't know if it was overruling the co-founder or sort of coming to consensus with that person, but that the fact that we had so much trouble getting to something clean and clear was like a symptom that they needed this work. And. And the C and so then we we restarted it.

Todd (53:49.122)

Yeah, yeah.

Andy Raskin (53:57.498)

And it was about two weeks, there was about a two week hiatus. There had been plenty of times where there's a naysayer where we have to sort of wrangle the story, but never one where we had stopped. And when they came back, it actually was great because now we're committed to finding it. You know? And.

Todd (53:58.766)

What was the time period between this hiatus? Okay. Yeah.

Andy Raskin (54:25.410)

And that happened relatively quickly. You know, sometimes we have to do an extra iteration if the team isn't quite there after that second one, but we didn't even have to do that. Like we got there really fast after that.

Todd (54:41.218)

Yeah, yeah, good stuff. Well, thank you, Andy. My final question is more, a little bit more of a personal question, and we're actually talking about it but when we were speaking before we started recording. But yeah, you're, for want of a better phrase, you're a one-man band, you're, I know, a consultant, a highly valuable one that's doing really, really great work, but why is it you choose to do this solo, and why do you not try and make this into a bigger thing, a practice, a bigger practice? I don't know, why do you keep it intentionally small?

Andy Raskin (55:09.774)

Yeah. Well, I do try to make it bigger. I do. I wouldn't say that I'm not trying to make it bigger, but I'm trying to make it bigger through just doing more. Honestly, like, I've raised my rate over the years, you know, since a decade ago. It's, you know, as I got more confident working with bigger and bigger companies, I charge less for smaller companies, but still. So, I try to grow it, but, you know, that...

Todd (55:14.144)

Okay, yeah, sure.

Andy Raskin (55:37.658)

that avenue of growing it through hiring people who are gonna be, you know, I'm gonna manage to do the work. I didn't wanna do that. At least I haven't yet. I might change my mind, but I really love doing the work and less so the managing of people. I also think I have, if maybe this sounds too full of myself.

But I think I have some kind of unique skills, unique background that's a mix of, you know, being a founder, technical background, and I was a magazine editor for a number of years. And I don't know, there's like, could I teach it to other people? I don't know, maybe, like probably I could, and maybe I will.

And I think about it now, especially as I'm getting older. I'll probably give you a photo that looks younger than I am now, I haven't taken one recently. But as I get older, I'm starting to think more about teaching more. I used to have, like I said, that that class in San Francisco, but that wasn't the covid kind of nicks that. And now I'm thinking about do I want to do that?

Andy Raskin (57:04.010)

you know, maybe in a different way. So I'm thinking about it.

Todd (57:06.502)

I mean, that sounds really interesting on the cheat. I mean, I guess it's a great, if you can create a training program which is really high quality and it really does bring people up as close to your level as possible, then I guess that can ultimately can create more impact for more companies and maybe be more meaningful for you. But yeah, maybe that's, yeah, something for the future.

Andy Raskin (57:27.594)

Yeah, and I just enjoy, I just enjoy like working with people on it. So I love doing that class. People, people were great. Um, they really did get it. So forget what I said about like me having special skills. It's not really that it's maybe just laziness or, um, just being, I guess, maybe just focused on the work. And now maybe as I'm getting older, thinking about, well, do I want to pass, you know, focus on passing it on a little more.

Todd (57:53.846)

Yeah, well, listen, I'd be one of the first people to sign up to any training course. I personally found this, yeah, your work super interesting and inspiring. You know, when I was researching this podcast, I felt like I connected the dots with a few companies and you know, how they've used your framework or similar framework. I find it incredibly interesting and not just for.

for our own company, for a small agency, I think even our own pitch deck and the way we approach things, I think we can do a much better job. So yeah, thank you for the work you're doing. And I think you already kind of mentioned where people can find you, but maybe you wanna end up by, yeah, just reiterating the best places for people to follow you.

Andy Raskin (58:35.842)

Yeah, probably best place is just connect with me on LinkedIn and follow me there. That's where I'm usually posting stuff Yeah, that's usually good

Todd (58:44.470)

Good stuff, and we'll also share the articles we mentioned here as well on a medium in the show notes. So thanks so much, Andy, this was great, and yeah, hopefully speak soon.

Andy Raskin (58:54.182)

Great, great.

Todd (58:56.995)

Thanks Andy.