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:
CEO Loom, Joe Thomas: Communication, the Mother of All Skills
President at Databricks, Andy Kofoid: Reinvention at Any Stage
Former CEO Splunk, Doug Merritt: Creating 360° Order in Chaos
CEO Stord, Sean Henry: Supply Chains... Are Fun?
Former President at NetApp, Tom Mendoza: Sustaining Urgency and Injecting Tension
President, Global Strategic Customers at Salesforce, Jim Steele: Measuring Your Facetime
CMO Attentive, Sara Varni: Cold Beer and Cheeseburgers
CRO Nextdoor, Heidi Andersen: Nurturing an Elastic Mind
CMO Rippling, Matt Epstein: Building the Supermarket of SaaS
CMO TripActions, Meagen Eisenberg: The Joy of Living in Awkward
CRO Unqork, Philip Lacor: Playing the Infinite Game
CBO Duolingo, Bob Meese: Carrying Culture Through Language
CRO Pendo, Jennifer Brannigan: Un-designing Your Leadership Path
CRO Rubrik, Brian McCarthy: Embedding Missionary Values Into Company Culture
President and COO Coinbase, Emilie Choi: Rising Through the Crypto Ranks
COO Bloomreach, Christy Augustine: Thin Mints and Company Building
CEO Alteryx, Mark Anderson: Transformation Starts with Leadership
CEO Relativity, Mike Gamson: Fueling the Next Technology Ecosystems
CRO Stripe, Mike Clayville: Building Tornado Companies
Chief Business Officer at Compass, Rob Lehman: Leadership by Fire
Create your
podcast in
minutes
It is Free
The Commercial Edge: Unleash the Power of People
The emPOWERed Half Hour
NABOR® TALKS
U.S Property Podcast
Aligned Money Show
The Ramsey Show
Planet Money