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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

#91

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!

Hello Sahil, thanks so much for sharing this. I know it helps a lot of founders out there.

One question: You mentioned that you raised ~$8m from investors, but that your liq. preferences used to be $16.5m. Was there a 2x preference in the Series A term sheet?

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

#92

Jesus this part sucks: "In those nine months, when the whole team knew that we were fighting for our company’s life, not a single person left Gumroad. From “this is gonna be hard,” to “yep, turns out it was,” every single person worked harder than ever." Did everyone one of these people have significant equity in the company? I'd expect people who love their jobs and who work on something crucial, such as researching…

The author mentions hiring a lot of good friends, so I assume they did it because they believed in him and the mission.

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

#93

I've always liked Gumroad as a product and service but this line kind of bothers me: > There is, of course, the $178,000,000 we have sent to creators This money wasn't sent to creators. They sold products worth $178M + Gumroad fees through the service. The creators made the products, marketed the products, acquired the customers, etc. When I use Paypal to sell something they aren't "sending me money".

> There is, of course, the $178,000,000 we have {sent, channelled, moved-through-our-platform, assisted in transferring} to creators

All of the above seem synonymous and none seems particularly malicious, but "sent" is easiest way to express it. For a marketplace, I don't think anyone's naive to believe the host is directly advancing funds to the tune of millions. Is it really necessary to nitpick that?

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

#94
I'm pretty sure this is the best post I've ever read on Hacker News, because of its potential positive impact on others. It's one thing to give advice, it's another to back it up with detailed life experience. The lessons shared here are invaluable ones, and if writing this story helps others learn them without having to go through as many trials to get there, you have done a great service. Bravo.

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

#95
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…

It is still baffling to me that the tech world has glommed onto a business model where steady growth and a solid core of loyal, happy customers is considered a failure.

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

#97
This is totally awesome, @sahillavingia. For a young guy, you have learned some incredible lessons about business in a VERY short time. You are positioned well to build that billion dollar venture that you originally dreamed of. It might not be called Gumroad, but who cares?

"It doesn’t matter how amazing your product is, or how fast you ship features. The market you’re in will determine most of your growth."

This is so utterly, absolutely, painfully true. We hear stories of hypergrowth as if you can just choose that path and it magically happens. Reality is: most companies never get to hypergrowth. Your only real option is to pick a large potential market with a reasonable hypothesis for getting there. And then see what happens.

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

#99
post #93

I've always liked Gumroad as a product and service but this line kind of bothers me: > There is, of course, the $178,000,000 we have sent to creators This money wasn't sent to creators. They sold products worth $178M + Gumroad fees through the service. The creators made the products, marketed the products, acquired the customers, etc. When I use Paypal to sell something they aren't "sending me money".

> There is, of course, the $178,000,000 we have {sent, channelled, moved-through-our-platform, assisted in transferring} to creators All of the above seem synonymous and none seems particularly malicious, but "sent" is easiest way to express it. For a marketplace, I don't think anyone's naive to believe the host is directly advancing funds to the tune of millions. Is it really necessary to nitpick that?

They should have said $178,000,000 in transactions.

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

#100
> It doesn’t matter how amazing your product is, or how fast you ship features. The market you’re in will determine most of your growth. For better or worse, Gumroad grew at roughly the same rate almost every month because that’s how quickly the market determined we would grow.

This seems like a simplification, and perhaps overly fatalistic. A company's growth rate is a function with many parameters, and at most points, one parameter will be the limiting factor. An amazing product is (usually) a necessary, but not sufficient condition for rapid growth.

It sounds like Gumroad built a product that delighted their users, but there just wasn't a level of market demand to hit the growth numbers that they were hoping for. (Though I consider their end state a big success; being a unicorn isn't the only way to add value to your users' lives.)

In a different market, with enough pent up demand for the product, the story could have gone another way; "We kept on getting new users, but ultimately couldn't keep users because our product wasn't awesome enough."

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