500 Hats is a startup consulting & investing company run by Dave McClure. You may wonder where my esteemed boss obtained the name … It’s all on the website but to direct quote:
The name “500 Hats” refers to the many hats that entrepreneurs have to wear as they get a new startup venture off the ground.
It’s also a reminder to entrepreneurs to spend time identifying all those hats, find talented people to wear them productively, and gradually take off & transfer the hats to others who can best help the business grow.
I also wear many hats as an advisor for several startups and non-profits.
and yes, there is a connection to the Dr. Seuss book “The 500 Hats of Bartholomew Cubbins”… I’ve been a fan since about the age of 3.
lastly, there’s a connection to my habit of wearing a variety of chapeau while playing ultimate frisbee around the SF bay area, sometimes while wearing a clown costume… but that’s another story for another time.