Six-Time CEO, David Cancel Has Some Tech Wisdom To Share

From serial entrepreneur to angel investor and Seeking Wisdom podcaster – David Cancel has done it all and he shared some of what he learned at TechCrunch's Disrupt SF conference earlier this October. In his ExtraCrunch talk, he emphasized a people-first over product-as-a-priority strategy and offered strategies for startups looking to gain a foothold in the fast-moving SaaS industry.

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Cancel started adult life as many people do – as a college student. He majored in both computer science and accounting but dropped out before finishing his degree after realizing it wasn't going to work for him. The six-time CEO admits that he had no idea what college was about when he applied and chose that school because it was ‘there'.

“I didn’t have a good experience because I didn’t feel like any of my professors – now, looking back – were that passionate about what they were teaching. I felt like I wasn’t learning anything interesting,” Cancel shared in an interview with Boston Globe. “I’ve always been obsessed with reading, and I still am, and I would spend most of my time in the library. We had the early internet, and that became my rabbit hole that I’m still in right now.”

One of his first entrepreneurial forays was as a founding member of, a social networking site marketed to teenagers, in 1996. Cancel also contributed to the success of search engine Lykos in its early days and served as CTO of online marketplace As chief product officer of marketing software provider, Hubspot, he scaled their operations by increasing their engineering team from 20 members to over 80 and helped position them for a successful IPO in 2014.

In an interview, Cancel said he knew it was time to leave Hubspot when he stopped being challenged by the job. “I got to a point where we did a lot of great things – we were going public, it was awesome – but that last year I felt I wasn’t learning anymore. I had a bunch of people who were reporting to me and they did stuff, and they felt like they could do it on their own.”

He is also well-known for launching marketing intelligence site Compete, Inc. which was purchased by TNS/WPP; social media advertising site Lookery acquired by Adknowledge in 2008; online provider of privacy tools Ghostery that was snapped up by Evidon in 2010; marketing optimization platform Performable bought by Hubspot in 2011; and online conversational marketing and sales initiative Drift where he currently serves as CEO.

Cancel is recognized as a leader in his field and was recognized as a top-ranked CEO by USA Today. He serves as Entrepreneur-in-Residence with Harvard Business School and has guest lectured on entrepreneurship at MIT, Bentley and other universities across the country. His blog has a devoted following of a million+ entrepreneurs and has written the best-selling book Conversational Marketing.