Episode: David Cancel

David Cancel of Drift

A bonus episode with special guest David Cancel! David is a five time founder, podcaster, author, former Chief Product Officer at HubSpot, and current CEO of Drift. He talks with Mike about lessons he’s learned the hard way.

Listen on iTunes!  Be sure to subscribe to get new episodes as soon as they’re made available. Like free stuff? Find out how to enter our giveaway and win awesome prizes.



Give us the elevator pitch of Drift

  • Drift makes it easy for your customers to buy
  • Focus on BtoB
  • Help demand gen marketer and sales team get back to people when they’re ready to buy
  • Ditch the old school/form/email way of buying

You had an article in the New York Times, where you tell a story about your formative years…

  • As you get older and time passes, the more you look at those early lessons.
  • Sam was my first mentor, although we didn’t know it at the time
  • Sam owned a ton of warehouses in New York.
  • I learned the power of humility from him, he was the most successful man I had met up to that time. No one knew how successful he was because he was always the first one to do the jobs people didn’t want. The first one to grab a broom.
  • Many people who worked there didn’t realize he was the owner of these companies.
  • I learned many lessons from him about turning failures into teachable moments.

As companies grow and add middle management, they struggle with delegating. What’s your experience with that?

  • It has taken me my entire career to be able to say three words: “I don’t know”
  • To myself, to my team, to my investors, to my peers.
  • The follow up is we’ll figure out the right way to do it.
  • Most of my early career was plagued by not wanting to say that. By not wanting to share autonomy.
  • There’s no such thing as the right idea, there are just options

People justify their role in leadership by saying that they have the right answers, which doesn’t necessarily qualify you for leadership. What would you say is the role of the leader, then?

  • Making sure you have the right people on the bus
  • Problems and solutions stem from people
  • So how do you share that autonomy? I started to look into servant leadership, and think about Sam. He was the first servant leader I knew.
  • Supporting people to have the best opportunity to have the most important impact on the business
  • The most people in the company are not in leadership. Companies make it so 95% of the company has no power. 5% do. That doesn’t make sense. Why not make it so that the people closest to the problem and closest to the customer have the power.

What are the things that you inherited from HubSpot when you started Drift?

  • Having the right people on the team from day one
  • It’s easy to overlook the amount of time that you spend coaching
  • There are no B players (Radical Candor), everyone has the opportunity to be an A player in at least one bit of domain
  • Push the fluffy culture stuff until later, don’t spend too much time on it in the beginning. Spend more time on coaching.
  • Coaching is the most important thing. The first thing to go are the things that we think don’t scale. So one-on-ones are the first things to go out the window. But one-on-ones are the key to scaling a team.

How do you mix young people with old people on a team? What’s the biggest challenge to hiring young people, and then what’s the biggest upside?

  • The biggest value is that they don’t have bad habits that you need to undo.
  • The weakness is that you need to develop skills, and you need to make an investment to teach them.
  • Most people don’t want to put in the time to make that investment.



Servant Leadership






Radical Candor –  www.radicalcandor.com 

Drift – www.drift.com

HubSpot – www.hubspot.com 



NY Times article