Former CEO of Drift, David Cancel, discusses his entrepreneurial journey and the importance of never feeling trapped. Topics include accountability, imposter syndrome, conservative spending, remote work, fundraising, and distinguishing between good and great ideas.
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Quick takeaways
Feeling pushed out of one's comfort zone can fuel drive for progression and growth.
The tension between living a comfortable life and the personal need for grinding and taking on challenging endeavors.
The importance of creating external accountability and commitment when starting a new venture.
Deep dives
The need for constant progression
The speaker emphasizes the importance of feeling pushed out of their comfort zone to fuel their drive for progression. They believe that growth comes from taking on challenges that feel overwhelming and uncertain. They express the desire to always be in a state of uncertainty and to pursue opportunities that make them question their abilities.
The struggle with finding purpose
The speaker discusses their current phase of feeling unsure of their purpose and lacking a clear direction. They explore various activities and projects they have engaged in during this phase, such as helping artists, but express that these endeavors serve as distractions and do not provide a sense of personal progression. They reflect on their continuous search for meaningful challenges that push them to their full potential.
The tension between comfort and the desire to grind
The speaker delves into the tension between living a comfortable life that others aspire to and the personal need for grinding and taking on challenging endeavors. They describe feeling like an outsider and not feeling settled, which fuels their itch for progression and a desire to venture out of their comfort zone. They express willingness to commit fully to their work, emphasizing the importance of dedication and obsession.
Taking the leap into launching a new company
The speaker reveals their decision to start a new company after a period of exploration and introspection. They discuss the process of committing to this new venture, starting with choosing a name and going public with it. They express the need to trap themselves and create external accountability. They plan to recruit a team, work on the idea, and pursue the goal of building a successful new company.
Navigating the Entrepreneurial Drive
The podcast discusses the relentless drive and ambition experienced by entrepreneurs. It explores the insatiable need to go bigger and keep proving oneself. The speaker emphasizes that this drive is inherent and cannot be taught, leading to commendable yet somewhat psychotic behavior. The podcast also touches on the addictive nature of the status games in the venture world. The speaker reflects on the fear of irrelevance and starting over, particularly in the context of founding multiple companies.
Challenges and Decisions in Running a Company
The podcast delves into the challenges the speaker faced during a particularly difficult year for their company. These challenges included personal struggles, questioning cultural and social issues, and transitioning from a high-velocity, self-serve model to an enterprise-focused one. The speaker shares their views on the potential mismatch between their gut feeling and external pressures. They discuss the multiple nightmares that arose, such as increased burn, disconnected customer touchpoints, and cultural shifts. Ultimately, the speaker reflects on the decision to sell the company and the hindsight validation it brought.
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.
