Guest: David Cancel, founder and former CEO of Drift; founder of Rey After HubSpot acquired his company Performable in 2011, David Cancel became his acquirer’s Chief Product Officer — and didn’t give any thought to how long he’d be in that role. When he started eyeing the exit a few years later, he was told that wasn’t an option: HubSpot had already filed to go public, and an officer of the company leaving in the first 18 months would raise major red flags. “Maybe this is what’s led me to be an entrepreneur,” David recalls. “I can never feel trapped … Someone telling me, ‘you can’t leave,’ I was like, boom. Switch went off in my head … and I was like, ‘I’m out.’” The filing was ultimately delayed and David was able to quit just before the IPO; one day later, he started his next company, Drift. In this episode, David and Joubin discuss the accountability of doing something, creating constraints, the Whitney Museum, imposter syndrome, Tony Hawk, John Romero, wandering without a map, conservative spending, Brian Halligan and Dharmesh Shah, Phil Jackson, the voices in your head, Shlomo Kramer, righteous independence, cancel culture and diversity, gut vs. data, and killing ideas with discipline. In this episode, we cover: Action and distractions (00:50)Observer and outsider (05:36)Advising entrepreneurs (11:18)“It has to be bigger” (13:23)David’s new company, Rey (16:38)Remote vs. in-person work (21:24)Who David will hire first (25:39)Fundraising and bootstrapping (27:39)The timeline for Rey (31:48)Rebuilding Hubspot’s code base (33:36)Leaving HubSpot at the IPO (42:54)“You’re not done” (48:19)HubSpot’s infamous exec meetings (54:44)David’s hardest year and selling Drift (59:26)The upmarket mistake (01:03:13)Saying no to good ideas (01:08:12)What “grit” means to David (01:11:52) Links: Connect with DavidTwitterLinkedInConnect with JoubinTwitterLinkedInEmail: [email protected] Learn more about Kleiner PerkinsThis episode was edited by Eric Johnson from LightningPod.fm