Brett Berson & David Cancel , In Depth

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

03 Dec 2020 • 50 min • EN
50 min
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Today’s episode is with David Cancel. David has been a CEO and founder of multiple different companies throughout his career. He’s also been a software engineer, a serial CTO, and the Chief Product Officer at Hubspot, giving him a unique lens into company building and leadership at different levels. In today’s conversation, David unpacks those lessons and tells us why he’s so focused on storytelling these days as the co-founder and CEO of Drift, a conversational marketing and sales platform. From screenplay writing inspiration, to how storytelling training is part of their onboarding, David shares how they teach storytelling and drive narrative internally at Drift. 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. It’s a must-listen for current founders and CEOs, and anyone looking to level up their leadership skills.   You can follow David on Twitter at @dcancel. He also pens a popular newsletter called “The One Thing,” and hosts a great podcast called “Seeking Wisdom”  For reference, the books he mentioned in the episode include Jon Kabat-Zinn’s work on mindful meditation, and “The Passion Paradox” by Brad Stulberg.  To learn more about how Drift approaches storytelling, check out this article David wrote for Inc:  To learn more about Charlie Munger’s concept of inversion that David mentioned, check out this Farnam Street post: You can email us questions directly at or follow us on Twitter @firstround ( and @brettberson ( 

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