Drift CEO shares insights from 20+ years of startup experience

Why do serial entrepreneurs keep jumping back in? What things might you learn the third, fourth, or fifth time around?

To find out, Extra Crunch Managing Editor Eric Eldon spoke to Drift CEO and founder David Cancel at TechCrunch Disrupt San Francisco. Cancel has spent more than 20 years founding SaaS companies, with exits including Compete (acquired by TNS), Lookery (Acknowledge), Ghostery (Evidon), and Performable (Hubspot.)

In their thirty-minute conversation, they cover everything from finding your first customers, to what he’s seen change over the last two decades in the industry, to why he’s willing to cut a check to employees who want to leave. Rather watch them talk for yourself? We’ve embedded a video of their chat at the end of this article.

To find what people really want, ask for money — any money.

One thing Cancel says he’s learned over the years: when you’re just getting started, you need to charge for your product right off the bat because you never know how someone really feels about a product until you ask for money.

“If you’re creating a paid-for product, you have to start charging from day one,” he says.

He outlines an experiment he

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