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:
President of Field Operations at BetterUp, Marc Maloy: Building Better Organizations by Building Successful People
CEO Incorta, Scott Jones: From Running Sales to Running a Company, and Everything in Between
Head of eSports at Activision Blizzard, Brandon Snow: Building 'Generational Fandom' of Professional Video Game Teams
Head of Revenue and BD at Asana, Oliver Jay: The Cutting Edge of Product-Led Growth
SVP Sales at Affirm, Eric Morse: Exploring The Partnership Between Engineering and Sales
CRO Front, LB Harvey: Moving Up-Market + Operational Excellence
CRO/CSO Dialpad, Dan O’Connell: Taking Risks and Running a Company
CCO Figma, Amanda Kleha: The Strategies Behind Figma’s $10 Billion Valuation
CRO Okta, Steve Rowland: Identifying and Developing Future Business Leaders
CRO Thrive, Renu Gupta: Building Positive Personal and Professional Habits
SVP Sales at Iterable, Jan Zeman: Hiring and Coaching Successful Sales Talent
Chief Customer Officer at Xero, Rachael Powell: The Power of Positive Psychology: Creating Authentic Company Cultures
President of Sprout Social, Ryan Barretto: Establishing a Compelling Company Vision
SVP Revenue at GitHub, Erica Anderson: Combining Top-Down and Bottom-Up Sales Motions
CRO DataStax, Harry Ault: The Three Steps to a Successful Tech Company Turnaround
VP Unity Technologies, Laura Palmer: Going The Extra Mile: Forging Meaningful Customer Connections
President and COO Golden State Warriors, Brandon Schneider: Building One of the NBA’s Most Valuable Teams
CRO RealReal, Kayti Sullivan: Setting Priorities in Work and in Life
CRO UiPath, Thomas Hansen: Balancing the Art and Science of Sales
VP of Global Professional Services at PayPal, Marcy Campbell: Risk and Reward: Creating Successful Sales Organizations
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