Reflecting on My Failure to Build a Billion-Dollar Company

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!

"inability to get enough people to know about it, and to understand how it would fit their needs?"

Just from visiting the landing page for gumroad.com, I wasn't clear about what the company did. Some questions that came to my mind:

By e-commerce, is it like shopify or like stripe? By audience-building software, is that SEO, marketing, or analytics?

Just writing the feedback I like to get from others. The features page answered most of my questions in general(I think its an online store platform for digital goods?).

> "inability to get enough people to know about it, and to understand how it would fit their needs?"

It's a bit ironic that one of the main features of the product is "audience building for creators".

Thanks for sharing this. It's really important not to give too much thought to hypotheticals as they're purely that: a hypothetical.