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Re:Reflecting on My Failure to Build a Billion-Dollar Company by jrochkind1 on Thursday February 07, 2019 @11:49AM (#19106391)
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. :)

Re:Reflecting on My Failure to Build a Billion-Dollar Company by sahillavingia on Thursday February 07, 2019 @12:13PM (#19106588)
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!

Re:Reflecting on My Failure to Build a Billion-Dollar Company by mrskitch on Thursday February 07, 2019 @01:42PM (#19107318)
Thanks for sharing this. It's really important not to give too much thought to hypotheticals as they're purely that: a hypothetical.
Re:Reflecting on My Failure to Build a Billion-Dollar Company by jammygit on Thursday February 07, 2019 @12:26PM (#19106685)
"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?).

Re:Reflecting on My Failure to Build a Billion-Dollar Company by amelius on Thursday February 07, 2019 @12:33PM (#19106741)
> "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".