Stop Hiding Behind Your Keyboard
Caldwell: You have to get out in the world and talk to people in person. You can't just hide behind your keyboard and call that talking to customers.
A lot of folks, their inclination is to build a landing page and buy some Instagram ads and try to get people to sign up for something. Maybe that's something. But I think the reason people do that is they're just shy and don't want to put themselves out there. It's a little awkward to go talk to people.
You can't just hide behind your keyboard and call that talking to customers.
The Self-Assessment
Caldwell: Be very tactical. Do a self-assessment. In the past month, how many in-person physical meetings have I had with potential customers?
It's shocking how many companies I talk to — they're like, well, we're focused on raising our pre-seed round before we talk to customers. The core thing going on is social anxiety and looking stupid. You've got to get past that. Start doing it until it doesn't feel bad anymore.
Think about how stupid the Airbnb founders must have felt. They were like — hey, you should rent out your house and I'm going to come sleep in it. The whole thing is a little awkward. You've got to power through the awkwardness.
It's shocking how many companies say they're focused on raising their pre-seed before they talk to customers.
20-30% of Your Calendar
Caldwell: Look at your calendar. 20 or 30% of your time should say customer meeting, customer call. When the calendar doesn't say that — when what you're actually doing is buying ads to try to validate your idea — I don't think that's talking to customers. That's something else.
Nothing substitutes for an actual conversation versus just staring at analytics dashboards.
Look at your calendar. 20-30% should say customer meeting. Buying ads to validate your idea is not talking to customers.
Patrick Collison Did It Too
Caldwell: I was an early Stripe customer at my startup and Patrick would be sending me messages on a weekly basis just checking in. Patrick was very hands-on with all of his customers. Extremely available.
I'm sure he had social anxiety going through all that. It wasn't a comfortable thing to do — keep pushing people to install your software. But if you want your startup to work, this is just what you've got to do.
Patrick Collison would send me messages weekly. If you want your startup to work, this is just what you've got to do.