The Future Of Conversational Marketing

David Cancel
Founder and Executive Chairman of Drift
2hr 4min
April 20, 2023
About the Show

"No, I didn't go to MIT. People who went to MIT work for me. I don't work for them."

David Cancel is the Founder and Executive Chairman of Drift, the world's first conversational marketing and sales technology company. David is a Bronx native who dropped out of college to pursue his career in tech. He has been part of six exits, including HubSpot, where he was the CTO responsible for revolutionizing their products and taking the company from a $100 million valuation to a public company worth $12 billion. He also founded Drift, which is currently the first company to focus on conversational marketing and AI. His work ethic and dedication to his craft is evident in his achievements and contributions to the tech industry.

Key Moments

The interview covers a range of personal and professional topics including cultivating work ethic, how to promote diversity in tech, raising money as a sales process, the importance of branding, discovering arbitrage opportunities in marketing, and intimately knowing one's strengths and weaknesses.

David’s experiences and perspectives are fundamentally unique and inspiring - if you have never watched the entirety of an episode, let this be the first. 


  • (00:00) - Intro
  • (2:30) -  Early years in the boogie down
  • (11:39) - Learning how to grow up in a city
  • (15:43) - First job in a Chinese-owned Warehouse
  • (19:12) - Why I dropped out of college 
  • (23:35) - Getting my first job in coding
  • (27:46) - Transitioning from student to entrepreneur
  • (30:17) - Being seen as a CTO in the startup industry
  • (36:40) - Why everyone is too specialized
  • (39:25) - Breaking into an industry where people don’t look like you
  • (47:00) - Founding Compete
  • (52:53) - Why I love raising money for a startup
  • (01:02:00) - The best way to approach a layoff
  • (01:08;00) - The concept behind Performable
  • (01:12:00) - Working for Hubspot after getting acquired
  • (01:20:00) - Rebuilding the code behind  Hubspot from the ground up
  • (01:24:00) - What makes a visionary product leader? 
  • (01:30:50) - How to enter into a good business partnership
  • (01:39:00) - Founding Drift
  • (01:43:30) - The importance of branding in a saturated market
  • (01:54:00) - Transitioning from founder to Executive Chair  


Conversational Marketing Book: https://www.amazon.com/Conversational-Marketing-Companies-Chatbots-Generate/dp/1119541832

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