Start with the story - Drift's David Cancel on lessons he's learned as a 5X founder

[00:00:00] I think a lot of my job has been as an editor. So I kind of think of myself as an editor and it's like, I'm obviously not doing any of the work, pretty small amount of the work, but I serve more as the editor of kind of, what is the voice? How do we get better on the voice? And. Where do we say not good enough?

Where do we push back and say, we can do a better job there. And so I try to continue to hold us to a higher standard, which again, it's these things it's easy when you're listening to this or thinking about them, they all sound nice and easy and obvious. And, but the real work is. Actually doing it and not compromising and, and doing that over and over again.

And that's the part that makes all the difference, because it's very easy to listen or read something and be like, yep, that's a great idea. It's obvious everyone should do that, but no one does it. And that's the point. 

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for today's episode of in-depth. I am thrilled to be joined by David cancel. He's currently the CEO. And co-founder of drift the conversational marketing and sales platform, but it's really the depth of his experience across his entire career. That stands out to me over the past 25 years, he's been a software engineer, a serial CTO, and then a chief product officer and repeat founding CEO, starting five different companies from scaling scrappy startups to running product at HubSpot.

He's had a broad range of experiences. What's also interesting is how David has managed to carve out tons of time for capturing and sharing what he's learned along the way. He's penned a best-selling book runs a popular newsletter called the one thing and hosts a great podcast called seeking wisdom.

In the past, David has spoken a lot about the power of storytelling as he puts it. They're obsessed with story internally at drift. So in today's episode, we're focused on finding out how he created this culture. As the CEO, from the inspiration they've taken from the screenplay writing world to how storytelling training as part of their onboarding.

We dig deep into how David teaches storytelling and drives narrative internally at drift. We also chat about his take on the role of CEO. David's got plenty of metaphors for how he sees his role from pruning a garden to serving as an editor, to being the coach who wants his team to question the place.

In addition to giving advice for engaging with exec teams and getting better at zooming in and out, David also share some really tactical frameworks, including Charlie monger's practice of inversion. The weekly rituals drift relies on and how to use asynchronous video communication. I hope you enjoy the episode.

And now my conversation with David, David, thanks so much for joining us. 

[00:03:35] Thanks for having me. I'm excited 

[00:03:37] to be here. So I wanted to spend the first part of our conversation, talking about CEO tools and approaches to the role of CEO. And this is a role that you've had in. Multiple different kinds of companies throughout your career.

And I thought maybe we could start, you've written a little bit about this, but the role of focus and your job as a CEO to figure out what to focus on and sort of drive that across the 

[00:04:02] country. I think from me adrift my current company each year, I kind of look at. What I'm doing as a job, and then try to figure out like, what's the next version of myself.

And every year that's been a pretty different version. And now more than ever, it's all about what are the few things that I can focus on that can help the team? I think about it, like two years ago, I would have been like on every slack message, every slack thread, every email, every kind of like in all the details.

And I would constantly would spend this time zooming in and out. So with zoom really low. And then I would zoom at a very high level. And now we're at the stage now that we have all of these leaders in place, we're about 400 and some odd people on the team. And I'm really trying to spend all my time, zoomed out very little, almost never kind of really diving in.

And so trying to figure out what are the things that I focus on. And what I figured out for me is that it really is those zoomed out things. It's about what is our story? Not only the vision, but really like, what is the story that we're telling for the next year, two years, five years? How do we do a better job at storytelling and teaching that storytelling internally and not only the story itself, but the act of storytelling so that there's all of these.

Smaller stories that we have to tell ourselves that we have to tell our teams when it comes to initiatives or projects we're working on, or even the larger story that I focus on. And so how do we train storytelling? How do we translate into that, into how we communicate to our customers, to our prospects on our website and every message that we write.

And so, like, I really think about building. That story first. And then we start to translate it into, okay, what are the offerings that we bring to market? How are the offerings that we have in place changing and what are the new stories or how are we adapting those stories? And then what does the story tell us that we need to build next?

And how do we validate that? And potentially how would it work with the existing solutions we have now and kind of what our customers are using. And so it's really this crazy focus on storytelling. Themes, and then kind of how do we action those themes and then eventually goals cascade out of that and initiatives kind of cascade out, but really I'm not spending so much time on the specific initiatives.

It's more about how do we tell these stories and what I've learned so far. We're still at the early stages that, that work is the easiest for me to ignore for the organization to ignore. But it's kind of the most powerful because when we have communication, Issues within the company or to our customers or prospects, like it all comes back to that.

We didn't spend enough time trying to understand the story and how that fits in our narrative, because like, we're trying to tell this very long narrative of where the market is going in terms of the categories that we're creating, but also how we're evolving as a company. And so. Everything has to fit into this longer narrative, even though we're so kind of focused on hitting our near term 

And so what was your process to land on that being's focus area for you and were there. Other things that you thought were important that you do prioritized? I feel like focus is one of those things. That's easy in theory. And then when you, as a CEO, look back on your last week and you map your calendar to that focus area, it often gets blown 

That you're exactly right. So for me, what helped me to focus on this area was the best incentive, which was pain and all the pain that we were feeling as an organization inside. And that at first I kind of saw as a bunch of. Different issues. They didn't really see the root of them. I saw all these communication issues.

I didn't know why as we were scaling the company, we were getting bigger, like why things were getting misinterpreted, why we were working on projects that we shouldn't be working on, why our customers were struggling to understand how we fit in their world and the larger world. Like all of these different things that I was running around, obviously trying to fix each and every one of those things along with the team.

And then I started to kind of zoom out. I kind of figured out pretty quickly that it all came down to like, Missing the story. And I was on this idea of story anyway, because I had basically taught myself how to become at least somewhat a marketer and starting drift. I have an engineering background. And so I was a software engineer and serial CTO and then CEO and chief product officer and all these things.

But I always built products for. Marketers and for salespeople, but I was not a marketer or a salesperson. And so I had to teach myself this idea of marketing. And I guess now at drift, I'm known more from marketing than anything else, but it's funny. So I took an engineering mindset to it and started with.

Okay. How do people make decisions and start to read all the books you can imagine on human decision-making and cognitive biases and social psychology and all these kinds of things, and then started to work upwards towards, okay. Okay. Copywriting, understanding copywriting and why it works when it doesn't work.

And then eventually how we think about marketing from a brand standpoint. And so story was always a big part. And so we're obsessed with story internally from a marketing standpoint. And then I saw the kind of connection. And I saw it because mostly cause of pain that we were having internally on all the other issues that we had within the company at that time.

[00:09:16] So how do you go about teaching storytelling internally and driving a narrative internally, other than the obvious stuff, which everybody says as a CEO, if you're not secure yourself saying something, you haven't said it long enough. But like pragmatically, if that's a main operating theme for you, what are you doing to when you get to the end of the year to say, I think we did an exceptional job in this focus 

First start by saying that I'm the worst I repeating. So of course I've heard the same thing, but I'm the worst I repeating and long ago I was trying to figure out how to get better at just public speaking and then figured out that. I have this problem where I can't say the same thing twice, which is, does not make for a good formula for public speaking.

And I was comparing myself against other speakers that I knew that were basically saying the same story 200 times and couldn't understand like why their performance was so much better in my eyes. And then I figured out, oh, I can't repeat anything in any way. I came up with a different style that worked for me, but for me to kind of institutionalize this within the company, it goes beyond just.

Talking about story. We started from the very beginning, from the first marketing person that we hired. And myself just studying all of this stuff, sharing it publicly on our own podcast and our normal marketing to other people about first understanding. Okay. How do people make decisions? Forget about the tools because in terms of marketing storytelling, everyone wants to go to like the channels.

How do you communicate things? What channels are you using and kind of get lost in the tactics of marketing, but what at least figured out pretty quickly was that most marketers, even though they were super effective on different channels of demand generation or events, and what have you didn't really understand why the messages that they were.

Using sometimes work, sometimes didn't work and didn't understand about how people made decisions and biases and things like that. And so we began to internally first train on that. So we have this thing called drift insider, which anyone can access for free in the world. And it's a bunch of video. It's basically like masterclass for marketers and salespeople.

So a bunch of courses that we've created internally and with third parties, but we have a version of insider that we first built internally that we'll continue to build. And it was all around this type of training that we put everyone who joins the company through, during their onboarding phase of not only what is our story, but how do you tell a story?

How do you give a presentation? How do you do copywriting, water, cognitive biases? What a, how do people make decisions? All of this kind of stuff. We kind of drill. Even if your job is not marketing and we continue to kind of live that and try to push that. That doesn't mean that we're great at it. It means that it's constantly an activity that we have to focus on.

I kind of compare all of this stuff to kind of growing and then with garden, which is like some amazing thing, but, and then most garden doesn't get built by just planting the right kind of plants. And 99% of the work is pruning and 99% of the work. To actually keep storytelling a focus is the pruning and making sure and zooming in when we're not doing a good job there and trying to repeat those lessons and it never ends.

And which I guess is non satisfying answer to a lot of people. Cause they want to shortcut there. Isn't a shortcut. It's just, we drill it. We make it a ritual. It's an institutional thing and it's a thing that's non-negotiable and I think that's probably the most important 

[00:12:32] part. What's an example of that concept of pruning for you in sort of this category of storytelling.

[00:12:39] So pruning is always the painful part for me. We just hired a new VP of product marketing. And so right now in the last two months, it's been about zooming in and just tearing apart how poorly the job we've done in specific product marketing work so far. That sounds simple. It is simple, but it isn't easy because someone has put that work in, someone is on the team.

Actually our whole team has worked on that stuff. And so you're just jumping in and trying to be helpful, but it's hard for people not to feel that in their egos, that pain, that shock of just like, this is how bad we suck at X, Y, and Z. And so we're constantly tearing apart. Stuff like that. And that's the only path to grow all growth involves discomfort, but like, it's easy to say, I want to grow and it's easy to say, like I want to learn, but nobody wants to go through the uncomfortable parts and very few people who go through the uncomfortable part, want to do it all the time.

Every single day, continue to go through that because it gets tiring. And so we have to build that kind of resiliency within the team. Does it mean that it doesn't hurt? It doesn't mean that it's not fun, but that's what we do. We kind of zoom in, we tear apart things. We try to build a case around it. We try to then make it a piece of when we can, if it's significant enough, like we try to share that internally.

Then we do a lot of this through doing our own videos. And so we'll send a drift video to the team or to put it, make it part of onboarding that then says, here's what we learned. We have this problem. We sucked at this. Here's how we fixed it here, results. And kind of, we try to teach a lot through video internal video courses, which just seems for a lot of the people on the team, a lot more effective than creating a deck, creating a document or some other form 

[00:14:23] in this case of like product marketing pruning.

Can you think of sort of a specific example where the team dove in found this thing was broken and sort of take it through the solution? I'd 

[00:14:36] say on that specific one often it's not the team. So in that case, the team didn't find that that was me jumping in and it doesn't have to be me, but it's probably someone on the team who really cares about storytelling.

Who's not going to. Kind of say when we're all in the stress and we are, when we're trying to build something, we're under a deadline, that's the easiest time to kind of give up on something like this and just take the shortcut or just follow conventional wisdom, or just repeat something you did before.

So I understand why people do it, but someone like myself or someone else who really cares about storytelling, kind of like zooming in. And in this case, what we saw pretty quickly was that, or what I saw pretty quickly was that we were reducing things. To the most scalable approach, which means kind of checklists, a ton of best practices, a ton of plays.

We call them plays internally, but no one was questioning any of the place. No one was thinking through the process or thinking about how to reinvent the process. They were just following the plays or following the checklist and completing checklists as quickly as possible. And so it was. They cared about their work, but there was about checking these boxes, getting this done, hitting the deadline, meeting the requirements and not about, okay, how do we make this better?

What is the actual message? Does the message resonate with anyone this worked last time, but will it work again? Do we have a new role model that we want to use in this thing? So no one was asking the why, why are we doing this? How are we doing it? Who is all about executing on the what and the, what that we had worked on last time or created a playbook around.

[00:16:10] This type of work is you sort of noticing something, surfacing it and sort of pushing people to 

[00:16:16] exactly. And I think a lot of my job has been over the years as an editor. So I kind of think of myself as an editor and it's like, I'm obviously not doing any of the work or a pretty small amount of the work, but I serve more as the editor of kind of what is the voice.

How do we get better on the voice and where do we say not good enough? Where do we push back and say, we can do a better job there. And so I try to continue to hold us to a higher standard, which again, is these things, you know, it's easy when you're listening to this or thinking about them, they all sound nice and easy and obvious.

And, but the real work is actually doing it and not compromising and doing that over and over again. And that's the part that makes all the difference. Because it's very easy to listen or read something and be like, yep, it's a great idea. It's obvious everyone should do that, but no one does it. And that's the point.

[00:17:09] in sort of playing the role of editor or setting standards of excellence, what is the line between what you should be pushing on and what an executive at your companies should be 

[00:17:20] pushing on? Great question. The answer is it depends and it's changing. So in the early days there weren't many executives.

And so I took it upon myself. Now I do ask myself that very question. Each time that I noticed something should have been an executive on the team caught this, should I be doing this? Should I stay out of this? And we use each one of these kinds of things when I do zoom and I do often the executive as part of it.

Part of it, to me is training that executive. My expectation is that most of this will be. Done by the executive, all the stuff about zooming in for sure should be our executive team holding on this. But right now it's kind of a hybrid. And where I see more of my time is kind of on that larger story and that larger initiative.

But yeah, it is something that the executive should be getting better at, but again, they have deadlines, they have goals, they have things to meet and it's the easiest place to. Ignore. And so it's always a constant game of current. Have 

[00:18:18] you sort of, these types of areas is it's hard on the binary, it should be X or it should be Y and really it's your judgment and instincts.

And so what you're really trying to do is help people kind of develop those instincts that in many ways, mirrors yours, or do you think you look at something and it's just objective, this is the right thing to do. This is the wrong thing to do 

[00:18:40] and go from me. Is that it shouldn't be. My opinion or my version of it, because I actually don't care about my version of it.

What I care about is that, and this is how my thinking works is that what I care is that someone has actually asked the question, someone can actually answer, why are we doing this? And if someone can do that in the process, if I see something and it doesn't seem right, and we have a conversation about it, if someone can say, here's why we're doing it.

And it's a very thought out kind of answer. And it makes sense on how they're thinking about it and why they're thinking that way. Even if I completely disagree with the execution of it, I will defer to them because they've thought out something and they probably have a hypothesis that I don't understand yet, but it's very well thought out.

But most of the time when you zoom in, it's not that it's kind of the opposite of that. And it's pretty clear when you talk to someone about why they're doing something. And they find it very hard to answer that. Why 

[00:19:36] question back to this sort of journey for you as a technical founder, technical CEO, you talked about this sort of learning process as it relates to storytelling sales marketing, are there.

Specific moments or frameworks that you've learned in that journey that I've had a disproportionate impact on your own growth as a story? 

[00:19:57] Yes, definitely. I'd say the first has nothing to do with storytelling, but it is that kind of monger idea of in birds. That's the first thing that we try to do is.

Try to work backwards and try to like come up with the simplest answer that way. When it comes to being able to tell a story, we kind of practice this technique of inverting, everything, which we learned from Charlie Munger, this kind of idea of like flip it the other way around start backwards. So I flipped it around and said, okay, so the idea is that.

I love Munger and that he simplifies everything is just it's to start backwards. So like, if whatever the goal is, if your goal is, and he uses this example and how he explains it, he asks his eight kids does this champion world champion who won the world champion title at this activity, this sport at the age 20.

And then they won again at the age of 75. What was the activity or sport? And some of the, his kids couldn't figure it out, but his son started backwards, inverted and said, okay, if they want a 20 and 75, it has to be a physical activity. So it couldn't be a sport that you have to play or that you have to have a high cognitive ability.

It has to be something. Different. And then he started to walk down and said, okay, chess, could it be chess? And it's like, no, you lose too much of your cognitive ability. By the time you're 75, like, it'd be hard to be a grand champion in chess. And then the next answer was like, okay, what is close to chest checkers?

And that was the answer. This person had one checkers because it was a game that you could. Kind of almost memorize pretty easily or the moves pretty easily, but he started backwards versus trying to start forward and saying, okay, start with all these sports and start to rule them out. He inverted and said what would have to be true for the answer to be correct.

And in this case it would have to be a sport that couldn't be physical. And so you start there, that's a very simple way of thinking about it. Like for us, our very notion of what we do as a company is that we've inverted. And we said, okay, like if the world has moved from a world of kind of fixed supply in terms of, let's say software and solutions and what have you then.

Sales and marketing tools can be built this way. And that's the way we built them this entire time, including myself. But if we believe that we're moving to a world of infinite supply where now the buyer has all the choice, okay. Now we've inverted the whole model. And so everything that we do at drift, because we believe that's true.

Starts with the buyer perspective, not the company perspective, not the sales rep perspective. And so it's a fundamentally different way to start to build marketing and sales software in our case, because we've inverted the thing and said like the world has changed because we believe this one thing is true, which is we've moved from fixed supply to infinite supply across every given category.

And so like, everything has to be flipped upside down now. So 

[00:22:38] that kind of. Charlie Munger inversion version ideas. Like one of these unlocks for you in this area of storytelling would love to continue on and hear more about other unlocks in your journey to be a marketer and storyteller. 

[00:22:50] Inversion was one tool which has nothing to do with storytelling, but then we started to study just the simple or the stuff that everyone knows in terms of storytelling.

Mostly that comes from. Writing screenplays. And so there's the whole Joseph Campbell's the hero's journey because the idea of the different archetypes for different hero types and people wanting the hero journey. And so even when we started a podcast, my podcast called seeking wisdom, I was trying to figure out like, what are our characters?

Like, who are we. Not that we are characters because it's so a hundred percent us, but like, what do we need to emphasize from a character standpoint? So people can identify with this character. And for me, my role in that podcast and myself and a co-host was his name, Dave. And he was a young kind of marketer and it was more of a kind of mentor mentee relationship.

And so my character was that of the Sage, which is like, I'm the old man from the hill. Who's got a bunch of stories and trying to teach us young, new. Hero who's on the beginning path of his journey, all of these lessons that I've learned. And that was kind of the two archetypes that we kind of emphasized.

It didn't mean that we were acting and doing any of those things, but we knew that we had to like follow kind of a story pattern for people to develop some sort of empathy or connection with us. And so that was an example of how we use. That whole hero's journey and hero archetype in creating a podcast.

But we also do that in kind of like stories that we tell or copywriting that, right. We're always trying to figure out how hero path. 

[00:24:23] Are there any other frameworks or things that you've learned along the journey that I've had outside? 

[00:24:29] I think it's pretty simple. I think those are the things that I think one of the things that we try to teach internally at drift was tend to stem more about how people make decisions and cognitive biases was too.

We do this in an internal course, like I do, which is use an example that everyone's familiar with in this case. It's the Amazon product detail page. So everyone's used that page. It's the page, that same template that they use pretty much for every product that they sell. And we kind of like break it down and say, okay, what is this page work from a decision-making standpoint?

And that really helps people understand, because if you were to look at it just from a visual standpoint or UI UX standpoint, your normal designer, if you asked them to redesign that page would remove every reason that that page works so well because to them, it would appear to be just a bunch of clutter, a bunch of colors and things competing for attention.

But if you start to look at it from how people make decisions, you'll see like, okay, there is a whole group of people that primarily make decisions based on kind of their social. Bias on the Amazon detail page, you'll see obviously reviews and video uploads and photo uploads and all of this stuff that like hits you from a social standpoint and wanting to belong and wanting to be like others.

And then other people may make decisions based on, there are people who want to make decisions immediately and they want everything right away. And you'll see things like that trigger that that are just like, Hey, we only have four more of these in stock, but then there's a reassurance that says, don't worry, we're getting more in.

And then they'll say like, if you buy now, we'll ship it to you by tomorrow at 1:00 PM. And there's all these triggers over and over again for every single type that you see on that page. And of course, most people are a combination of these types of these things kind of work together. And again, to use another

Mongers gave this speech one time that said, if you trigger more than one cognitive bias, then you get into this Lollapalooza effect. That's what you call it. And that's the ultimate thing where you're triggering someone on multiple biases at the same time. And that really changes how they make decisions.

Today's episode is with David Cancel, co-founder and CEO of Drift, a conversational marketing and sales platform. This 5X founder has also been a serial CTO and the Chief Product Officer at Hubspot, giving him a unique perspective on leadership. In addition to his take on the CEO role and advice for managing exec teams, David shares why he focuses so much on storytelling and how the Drift team constantly works to get better at it.

Start with the story - Drift's David Cancel on lessons he's learned as a 5X founder

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How This 5X Founder Creates an Internal Culture With a “Crazy Focus” on Storytelling