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He’s had six near death experiences, and we talk about how those influenced him throughout life. We also talk about some of his early businesses, including one that had the FBI at his house when he was a kid, and lessons driving the monorail at Disney.

We also get into the founding story of ClickUp, bootstrapping to $10m in ARR, hiring mistakes from scaling too fast, why Zeb likes hiring users, how ClickUp shipped generative AI features so fast, its new chat product launched earlier this week, and the trend of software convergence.

Timestamps:
(00:00) Intro
(02:11) Zeb’s first near death experience
(08:19) Childhood businesses that had the FBI at his house
(18:23) Lessons from driving the monorail at Disney
(25:19) Mistakes scaling from 100 to 800 employees in one year
(31:04) Dropping out of college after being robbed at gunpoint
(33:19) How building a CraigsList competitor led to ClickUp
(35:32) Three waves of ClickUp’s product evolution
(39:25) How the product slowly got worse over time
(44:45) Hiring the guy who built Microsoft Teams to rebuild ClickUp
(48:11) Zeb’s favorite interview question
(49:59) Daily 5am standups in the first year
(54:28) How ClickUp got its first customers
(57:16) Bootstrapping to $10m in ARR with strong retention
(58:13) Zeb’s best kept secret, user surveys (and how to run them)
(1:02:42) The trend of software convergence
(1:08:26) Reasons Zeb likes hiring users
(1:12:19) Why VCs didn’t invest, and why it led to a better business
(1:19:02) Raising from Craft, Georgian, and a16z
(1:21:08) Peter Thiel: “I think you’re right”
(1:24:35) How ClickUp was early to AI
(1:28:03) Launching chat and video calls to hit ClickUp's original vision
(1:32:02) What Zeb’s excited and cautious about in AI
(1:37:24) Why Zeb journals every day

Referenced:
ClickUp: https://www.clickup.com
ClickUp’s new chat feature: https://clickup.com/features/chat

Follow Zeb
Twitter: https://x.com/dj_curfew
LinkedIn: https://www.linkedin.com/in/zebevansclickup

Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Newsletter: https://www.thespl.it/

214 - Rick Cotton, Exec. Director, Port Authority of NY & NJ