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:
Links:
#190 Co-Founder Cost Plus Drugs, Mark Cuban: Mavs to Meds
#189 Co-Founder Watershed, Taylor Francis: Worthy Missions
#188 CEO and Co-Founder Synthesia, Victor Riparbelli w/ Josh Coyne: Gorilla in the Room
#187 President & COO of AG1, Kat Cole: Wings to Supplements
#186 COO Asana, Anne Raimondi: Recovering Perfectionist
#185 CEO and Founder Netskope, Sanjay Beri: The Trenches
#184 Former CEO and Co-Founder Sun, Scott McNealy: In the Piñata
#183 CEO and Co-Founder Harness, Jyoti Bansal: Three-Layered Cake
#182 CEO and Co-Founder Cribl, Clint Sharp: Finding Traction
#181 CEO Transcarent, Glen Tullman: Problem Solving
#180 CEO and Co-Founder Verkada, Filip Kaliszan: Outlier
#179 CEO and Co-Founder Zapier, Wade Foster: Missouri’s Connector
#178 Author of “Radical Candor,” Kim Scott: Uncommon Sense
#177 President and Co-Founder Anthropic, Daniela Amodei: AI Hurricane
#176 CEO MongoDB, Dev Ittycheria: Edge
#175 CEO Snowflake, Frank Slootman: Amped
#174 CEO and Co-Founder Ginkgo Bioworks, Jason Kelly: Life Finds a Way
#173 Author of “The Qualified Sales Leader,” John McMahon: The Five-Time CRO
#172 Professor at UPenn & Author, Angela Duckworth: Grit
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