Gumroad

“Raised ten million bucks from Kleiner Perkins, Max Lefgen, Naval, Chris Saka, the wonder kind of story, college dropout, everything like that.”

“So Max Levchin, I wanted him on the cap table so bad for Gumroad. He was the last person to say yes, and he asked for all of these references. It was so intimidating meeting with him, and when he finally said yes, I asked him afterwards. I was like, what got y…”

“I just started writing and painting and really just not thinking about Gumroad more than the four hours a week I was doing support.”

“Yeah, I think Reid's quote was accurate maybe 10 years ago when he probably said something like that, but the truth is the bar for where your product needs to be today is so much higher, and yes, you should be embarrassed because I think the best founders will…”

“In 2011, Gumbert actually launched before Stripe launched”

“Our pre-seed round, or our seed round back then it was called, was 1.1 million. Excel put 400 K into that.”

“Frankly, if I could go back in time, I would have said no to them. I would have given that 400 K a hundred K to four different people, super angels or angels, or even split it further.”

“Gumroad, it took me seven, eight, nine years to get to a place where Gumroad kind of is considered, like, you know, we're at ten million in revenue doubling every year, but that's because of a macroeconomic shift, namely COVID, that just happened out of the bl…”

“Did a round of layoffs, 75% of the company went from 20 people down to five people, got to profitable, got rid of the San Francisco office, and moved out of San Francisco, left six years in, moved to Provo, Utah.”