Number One Sink Cleaner: An Interview with Serial Entrepreneur David Cancel

There’s only one shortcut in life, according to David Cancel.

The serial entrepreneur (and sometimes Buffer advisor) is currently working on his fifth startup, Drift, which allows you to talk to your website visitors and customers in real-time, from anywhere.

But his biggest passion—and his top secret to a great life—is continuous, voracious learning. It’s a topic he explores in his own podcast, Seeking Wisdom. (It’s one of our CEO, Joel’s, favorites!)

His startup background runs deep: He’s founded and built multiple companies and previously was Chief Product Officer at Hubspot. In addition to Drift, he is an advisor, investor, and consultant to many organizations.

In this CultureLab interview, he talks about why he can’t watch Silicon Valley, why he only aims to do one important thing a day, and how Drift’s commitment to servant leadership means he’s the#1 sink cleaner in the office.

Plus: Carolyn and I chat about Buffer’s self-management experiment—what went right, what went wrong.

What you’ll learn from this episode:

• What self-management is (and isn’t)
• What Buffer got right and wrong in working toward it
• The difference between self-management and holacracy
• How Zappos implemented Holacracy
• Bringing your whole self to work
• What it means to be a serial entrepreneur
• Why every startup and company is 99% people
• The obsession that guides every decision David makes
• How David influenced one of Buffer’s biggest decisions ever
• Why most advice is “simple, not easy”
• The only shortcut in life
• Why working all the time doesn’t work
• David’s morning routine to create intentional days
• The only thing standing between going from good to great
• What life was like inside Hubspot
• The “small rocks vs. big rocks” way to work

Stuff we talk about in this episode:

• Reinventing Organizations by Frederic Laloux
• Theory X vs. Theory Y
• Holacracy
• The Holacracy book by Brian Robertson
• Zappos and their Holacracy journey
• Servant leadership
• Disrupted by Dan Lyons
• Silicon Valley
• The 7 Habits of Highly Effective People
• The Martian
• David’s list of “Books Every Startup CEO Should Read,” which he is going to add some women to!
• Former Washington Post CEO Katherine Graham, who did write a book

Notable moments

• 2:50: Hire good people and step back
• 4:40: We removed all structure
• 5:00: How Holacracy works
• 8:09: Trees don’t send emails
• 10:40: It’s not as fun over here
• 11:45: I feel like playing Xbox all day
• 12:57: What’s the opportunity cost?
• 13:32: Personal growth challenges
• 15:00: It slowed us down more than we could imagine
• 16:19: Happy to have a boss
• 17:47: Selling infomercials
• 18:38: “If you’re an entrepreneur once, that’s excusable… If you do it repeatedly, that probably says something about you.”

• 19:20: It’s not about ideas
• 20:50: 100% obsessed
• 21:37: “Starting companies is like the rabbit hole that never ends”

• 23:08: When Joel and Leo were working from a gym
• 24:39: Simple, not easy
• 26:17: “Most of the important things I’ve learned, I’ve learned through repeated pain.”

• 26:47: The only real shortcut that exists
• 27:34: When I was 18, I knew everything
• 28:20: “Whoa, I know who this is”
• 31:03: Do you start your day intentional?
• 33:45: It’s going to look kinda crazy
• 34:25: Geeking out on culture
• 35:22: Happiness at the top of the pyramid?
• 36:01: I’m the #1 sink cleaner
• 38:27: Putting ego to the side
• 42:32: I don’t know if he’s ever been in a sweatshop
• 43:50: One important thing
• 44:47: The Martian as lean startup guide
• 46:00: He’s talking about Katherine Graham, who did write a book!

Further reading

24 People, No Managers: Our New Experiment in Getting Work Done at Buffer

What We Got Wrong About Self-Management: Embracing Natural Hierarchy at Work

Self Defined Self Management: How Our Startup Is Figuring It Out Together

Get in touch!

• Connect with David: Twitter | website
• Connect with Carolyn on Twitter
• Connect with me, Courtney, on Twitter!

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Over to you!

Would you ever want to try working without structure? Do you want to challenge David Cancel in a pizza bake-off? We’d love to hear from you in the comments, on Twitter, or at culturelab@buffer.com!