#171 Founder & Former CEO Drift, David Cancel: Never Trapped
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:
Action and distractions (00:50)
Observer and outsider (05:36)
Advising entrepreneurs (11:18)
“It has to be bigger” (13:23)
David’s new company, Rey (16:38)
Remote vs. in-person work (21:24)
Who David will hire first (25:39)
Fundraising and bootstrapping (27:39)
The timeline for Rey (31:48)
Rebuilding Hubspot’s code base (33:36)
Leaving HubSpot at the IPO (42:54)
“You’re not done” (48:19)
HubSpot’s infamous exec meetings (54:44)
David’s hardest year and selling Drift (59:26)
The upmarket mistake (01:03:13)
Saying no to good ideas (01:08:12)
What “grit” means to David (01:11:52)
Links:
Connect with DavidTwitter
LinkedIn
Connect with JoubinTwitter
LinkedIn
Email: grit@kleinerperkins.com
Learn more about Kleiner Perkins
This episode was edited by Eric Johnson from LightningPod.fm
SaaStr 626: 10 Lessons Learned Scaling to $1B Valuation with Drift Co-founders David Cancel and Elias Torres
Reaching unicorn status is nice validation, but the luster fades when founders can't navigate the hidden challenges that come with uncharted territory. David Cancel and Elias Torres, co-founders of Drift, share their insight on steering a company to a $1B valuation with both the tenacity to problem-solve and a fearlessness to fail. They'll take you through their own personal experiences, from creating a scalable product strategy to building an enduring company that puts people and purpose before profit. Find out how the steps they took not only helped nurture a company's success, but also allowed its leaders to retain a growth mindset long after they hit the $1B milestone.
Full video: https://youtu.be/gGVSaRcZkOs
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SaaStr 019: David Cancel on Hiring People Not Skills, The Importance Of Investing In Relationships and Being Scrappy
Following our meeting at SaaStr Annual 2016, I am thrilled to welcome David Cancel. Now David really is a serial entrepreneur having founded 5 companies, with the last, Performable, being acquired by Hubspot, resulting in his taking up the position as Chief Product Officer at Hubspot. Now David is the CEO @ Drift. Drift allows you to talk to your website visitors and customers in real time. David is a master when it comes to hiring, company culture creation and maintenance and team building and we dig into all that in today's episode, as well as:
Why David's golden rule to recruiting is hiring people not skills?
Why is cultural fit so important for future employees? How can you test for it in an interview? Can you hire a team of all A team players without having insane competition and friction?
What does David mean when he says it is important for candidates to be scrappy? What signals are there that the person is an insane hustler?
What questions does David pose to get the candidate out of the standard interview style answering? How does david push them out of their comfort zone?
Why does David believe it is crucial to never hire PMs who have done it before? What is the benefits of this?
How does David view success? What commonalities does David se in thementiality fo those that have and have not been successful?
In a round we call the 60 Second Saastr, we also hear:
Must read books for startup CEOs?
What are the 3 biggest lessons you learnt the hard way?
What is David's approach to learning?
If you would like to find out more about the show and the guests presented you can follow us on Twitter here:
Jason Lemkin
Harry Stebbings
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David Cancel