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

David Cancel has penned two books, crafts a popular weekly newsletter, and hosts a great podcast. But he’s not a marketer by training. In fact, he’s held plenty of other titles, from software engineer and CTO, to Chief Product Officer, co-founder, and CEO — perhaps not the resume that comes to mind when you picture a storyteller.

“Even though I always built products for marketers and for salespeople, I wasn’t a marketer or a salesperson. So I had to teach myself marketing,” says Cancel, now the co-founder and CEO of Drift. As it turned out, he was a quick study.

A good story has played a pivotal role in Drift’s marketing from the outset — as Cancel has previously detailed in his newsletter:

“We didn’t want to talk about software, websites, or widgets. We wanted to tell a story. That’s why we used the analogy of an empty store. We talked about people spending all of this money on advertising trying to get people into the store, and then when the customer gets there and wants to buy something, there’s no one there who will talk to them. It made sense because we weren’t just talking about all of our great features. We were telling a story in a way that showcased the experience and outcome we knew our customers were looking for.”

What we found most interesting in our recent conversation with Cancel was how that storytelling remit has since expanded, shifting from a purely external exercise into a vital internal center of gravity for the company.

"While we were obsessed with story from a marketing standpoint, it wasn’t until later that I saw the connection between storytelling and the pain that we were having internally. I really started to think about building that bigger story first, and how we can do a better job at storytelling — not only the story itself, but the act of storytelling and training on that internally."

Today on The Review, Cancel gets more granular on how he created this internal culture centered around storytelling, sharing five lessons on how to weave storytelling into all that your startup does. From the inspiration they’ve taken from the screenplay writing world, to how storytelling training is part of their onboarding, we dig deep into how Cancel drives narrative internally at Drift.

We also chat about his take on the role of CEO—Cancel'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 plays.

He also shares tactical advice for engaging with exec teams and getting better at zooming in and out as CEO, as well as some really tactical frameworks, including Charlie Munger’s practice of inversion, the weekly rituals Drift relies on, and how they use asynchronous video communication.

Thanks, as always, for reading and sharing.

-The Review editors

Resources worth sharing:

One of DoorDash's first 50 employees shared an inside look at how the company sped up in the food delivery space.

Caroline Clark put together a deck with a handy overview on how B2B companies can scale go-to-market efforts.

Kathleen Estreich and Emily Kramer created a helpful guide on how to organize your early-stage SaaS marketing organization

Denys Zhadanov on a better way to read books.

Some inspiration on going above and beyond for customers.

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