Reflecting on My Failure to Build a Billion-Dollar Company

Amazing and poignant story; thank you for sharing.

I do wonder if there was a path for Gumroad to become a Shopify killer, instead of focusing on sellers too small and unsophisticated for Shopify, which limited the addressable market.

They're not really congruent products… if anything Gumroad is more similar to Stripe. But to take your question seriously, I'd far rather hack together a shopping site and use Gumroad for payments than grapple with Shopify again, they give me a migraine.

Gumroad is also going to have some new opportunities if Patreon continues to struggle with their similar deal-with-the-devil.

+1 Gumroad, glad to see it's found a way to thrive.

Yes I'm confused why Gumroad didn't become more like stripe or patreon. That would've been a natural development. It must be execution problems.