Drift CEO shares insights from 20+ years of startup experience

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.

“What it teaches the entrepreneur is that most of the people who will tell you that they love this thing will not give you a dollar,” actionable information that can save time, money and stress.

The dollar test “shortcuts things; most people will end up spending so much time coming back to you because you keep telling [them] you love it, because you’re a nice person and you don’t want to hurt [their] feelings.”

They’d say ‘I have to go talk to my manager, I need to go talk to someone, I’ll get right back to you,'” he said, adding “Almost every single time that person continued to be a customer and never asked for that feature again.”

Similarly, if an employee says they want to leave and start their own company, David says he’s often the first to write a check:

“We would attract, in the early days, people who wanted to learn how to start their own company.

One of the things I would say, and I still say to everyone: Look, if you come on board, and work with us for some days, if you want to leave at any point and start a company, myself and my co-founder Elias will be the first checks in whatever you want to start, no questions asked.”

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