F-Prime Capital had the privilege to host David Cancel, CEO and Founder of Boston-based Drift as part of our Founders Diaries series. David’s first exit was Compete where he set a standard for how a CTO’s vision and acumen can drive the success of venture-backed startup. He didn’t stop there, after Compete, David continued his successful entrepreneurial journey as a founder of Ghostery, Performable and Drift. He’s served as the CTO of Hubspot and has guest lectured at MIT, Harvard and other universities. David writes a popular blog davidcancel.com and hosts a podcast series (Seeking Wisdom). Finally, David literally wrote the book on Conversational Marketing (out now!).

David’s discussion reflected on his entrepreneurial journey through several startups with a focus on relaying experiences from which we can all learn.

Here’s what we learned from David Cancel’s conversation:

Breakthrough ideas don’t happen overnight:

Even a 5 time entrepreneur like David doesn’t have the expected eureka moment. It’s a long journey of continuous feedback and tweaking to evolve a company to take a company to the next level — a constant cycle of feedback and reiteration.

“I thought I was going to have a breakthrough idea because that’s the movie scenario… that has never happened. Every idea morphs. The idea doesn’t matter — the customer and the macro changes matter, somewhere there is the big idea.”

The dollar test:

When working to close the deal, there is always one “significant” feature missing for the prospects use case. Inform the prospect you’ll add feature but it will be an additional costs (minimal compared to the monthly fee.) Most turned downed the addition feature and don’t request it again. Customer feedback is king, but features and customization requests need to be validated through the sales process, hence the dollar test.

It’s all about the feedback:

Without listening to customers, you can’t build a product that everyone wants to use. Even today, David is committed to staying close to the customer, learn from the customer, and reorganize the entire company around learnings and iterate. Each month, all Drift team members are required to get on the phone with Customers, including David, to hear directly from customers.

As a leader, continuous learning:

Build a culture of continuous learning. It may feel like you are always in a state of discomfort, but it’s worth the pain for the lessons you learn from your customers. Continuous learning requires controlling your ego and listening to painful feedback over and over again.

Thanks again to David Cancel to sharing his story at Founders Diaries! Are you interested in attending a future Founders Diaries event? Sign up to stay in touch and learn about future Founder Diaries.

Check out photos from the event: