Reflecting on My Failure to Build a Billion-Dollar Company

Hey, #1 on Hacker News! I don't think that's happened since...I launched Gumroad back in 2011:

https://news.ycombinator.com/item?id=2406614

Thanks HN for being a part of my journey!

I hadn't heard of Gumroad before -- it actually looks like a really good product, and one that I would have occasion to recommend to people.

To what do you attribute the challenges?

Were you building a product there wasn't a market for, what you were delivering wasn't what people wanted?

Or, a marketting failure, inability to get enough people to know about it, and to understand how it would fit their needs?

Or, what I think I get from your post, is maybe you think neither of these -- rather you just tried to grow _too quickly_, quicker than the market/product could bear, and then had to deal with that.

Do you think if from the start you had _not_ tried to create a "billion dollar company", stayed smaller, accepted less investment with clearer expectations, had fewer employees, etc. -- you would have still been able to get to where you are now, but quicker and with less pain? You still would have been able to get _enough_ investment, and with the investment you had still would have been able to build the product succesfully?

I think maybe that's what your essay is implying you are suggesting, but I'm not totally sure if that's what you mean to be suggesting; or maybe you don't mean to be "diagnosing" it at all and aren't interested in these questions of what-could-have-been at this point. :)

I really tried to avoid being prescriptive about the solutions. It's a lot easier to talk about the problems :)

> aren't interested in these questions of what-could-have-been at this point

Exactly. If we shipped this or that feature... If we raised more, or less.. If I stayed at Pinterest... If I invested in Bitcoin...

I'm just not sure I gain a lot from thoughts like that!