DHH is such an OG tech founder, I don’t think I realized his first paychecks from 37Signals was in the form of apple tech. What a shift to being such an apple fanboy to rage quitting and building a great linux distro that is siphoning his followers out of Mac.
I love the reminder of Gary V’s Jab, Jab, Right Hook. Meaning that you should build a following first, give, give, teach, show you have value then ask for something. The host mentioned one day they were frustrated with something, his co-founder suggested basecamp, and his response was buy it. Not shop around, see if theres something better, just buy it. He said these are my people, they’ve already given so much that I have no questions to whether or not we should give them money.