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Reflecting on My Failure to Build a Billion-Dollar Company

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Re: Reflecting on My Failure to Build a Billion-Dollar Company

#21
I remember when Gumroad first launched. I was 24 at that time and just couldn't believe that a kid that young could be so good at making such polished products.

To that end, I considered Sahil - and people like him - to be my model of success: being able to bring your vision to life.

Re: Reflecting on My Failure to Build a Billion-Dollar Company

#22

Ouch, number 2 employee at Pinterest - a $10 billion company that’s about to go public this year. He probably would have been worth an easy 100-200 million.

Pinterest is a malignant tumor on the face of the Web that exists to trick people who are trying to search for images. Being rich off that would be worse that toiling in obscurity.

Re: Reflecting on My Failure to Build a Billion-Dollar Company

#23

Ouch, number 2 employee at Pinterest - a $10 billion company that’s about to go public this year. He probably would have been worth an easy 100-200 million.

Reminds me of Noah Kagan. Employee #30, I think, at Facebook. That should be what - $200M+?

Re: Reflecting on My Failure to Build a Billion-Dollar Company

#24

Ouch, number 2 employee at Pinterest - a $10 billion company that’s about to go public this year. He probably would have been worth an easy 100-200 million.

Pinterest is a malignant tumor on the face of the Web that exists to trick people who are trying to search for images. Being rich off that would be worse that toiling in obscurity.

People actually do use Pinterest to collect images, I think, but I agree with you on the other points

Re: Reflecting on My Failure to Build a Billion-Dollar Company

#25
post #11

Really love this post. My favorite line is: > Every month of less than 20% growth should have been a red flag. I think that's pretty insightful. 20% growth is great for a normal business, of course; for a VC-backed startup it can show some warning signs about future hard decisions you might have to face. I think there's certainly lots of discussion that has been had — and should be had — about "should I or shouldn't…

Actually 20% per year would be great for most businesses, which just shows what an outlier VC backed businesses have become.

Re: Reflecting on My Failure to Build a Billion-Dollar Company

#26

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. :)

Re: Reflecting on My Failure to Build a Billion-Dollar Company

#27

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!

http://omswami.com/2011/11/the-successful-and-the-successfoo...

Re: Reflecting on My Failure to Build a Billion-Dollar Company

#28

Ouch, number 2 employee at Pinterest - a $10 billion company that’s about to go public this year. He probably would have been worth an easy 100-200 million.

You are vastly overestimating what even an early employee (esp a jr one) gets at a unicorn. Not that it wouldn't be substantial today, but nothing close to 1-2% of the entire value of the company.

Re: Reflecting on My Failure to Build a Billion-Dollar Company

#29
post #11

Really love this post. My favorite line is: > Every month of less than 20% growth should have been a red flag. I think that's pretty insightful. 20% growth is great for a normal business, of course; for a VC-backed startup it can show some warning signs about future hard decisions you might have to face. I think there's certainly lots of discussion that has been had — and should be had — about "should I or shouldn't…

This would be 9x per year. What are examples of companies with such a growth rate?

Re: Reflecting on My Failure to Build a Billion-Dollar Company

#30

Ouch, number 2 employee at Pinterest - a $10 billion company that’s about to go public this year. He probably would have been worth an easy 100-200 million.

crunchbase says pinterest has had 15 funding rounds. certainly they weren't all complete rounds and it would've been nice equity but nowhere near the nominal 1-2% early employees get.
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