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:
#132 Former 49ers Quarterback Alex Smith and Former Warriors Guard Shaun Livingston: Hard Steps
#131 Golden State Warriors Forward Andre Iguodala: The Sixth Man
#130 Former Vice President Al Gore: Relentless
#129 CRO Zapier, Giancarlo “GC” Lionetti: Recheck, Rebalance
#128 Former COO and Corporate Officer at Stripe, Claire Hughes Johnson: Scaling People
#127 CEO Intuit Mailchimp, Rania Succar: Consistent Inner Equilibrium
#126 CRO Gem, Lesley Young: Hard Yards
#125 CRO Starburst, Javier Molina: Reading Cues
#124 Founding CRO at Procore, Dennis Lyandres: Defining "Winning"
#123 CEO GitHub, Thomas Dohmke: Open-Source Values
#122 President and Board Member at Freshworks, Dennis Woodside: What If This Goes Really Well?
#121 Founder and Co-CEO Brex, Henrique Dubugras: Pivot or Else
#120 Chairman & CEO ServiceNow, Bill McDermott: Full Speed Ahead
#119 Co-founder and CEO Gong, Amit Bendov: No Royalty
#118 Dean of Stanford GSB, Jonathan Levin: Innovation Engines
#117 Co-founder and COO Cloudflare, Michelle Zatlyn: A Better Internet
#116 Grit Recap: 9 Intersections of Personal and Professional
#115 Executive Board Member at SAP, Scott Russell: Chief Optimist Officer
#114 CMO GE, Linda Boff: Play ‘Til the Whistle
#113 CEO PagerDuty, Jennifer Tejada: The Re-Finder
Create your
podcast in
minutes
It is Free
The Commercial Edge: Unleash the Power of People
The emPOWERed Half Hour
Reaching your Goals
Insights@work
Business Dad
The Ken Coleman Show
The Cardone Zone