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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

#41

Post by ikeboy »

AznHisoka wrote: post #4

I wasn't interested in the emotional story behind this. But I did resonate with 1 line in particular here: "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 true, in my experience. You hit a roadblock in recurring revenue, not because your product doesn't have enough features, or your team sucks, but simply: your market…

The corollary is that you can shift the market you're in and increase growth.

Clickfunnels addresses a slightly different market and has 9 figures of recurring revenue. Partly because they charge a lot more and have a lot more bells and whistles, partly because they have way more intensive marketing, but partly because they're targeting the demographic that wants those bells and whistles over the simplicity of gumroad.

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

#42

Post by sahillavingia »

asaddhamani wrote: post #35
sahillavingia wrote: post #13

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!

Hey Sahil, Big fan of Gumroad! As a customer, it's one of the neatest checkout flows I've come across, among Stripe. Do you have any plans to expand into subscription offerings?

We do offer subscriptions! https://help.gumroad.com/11163-products-and-customizations/s...

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

#43

Post by randlet »

beachy wrote: post #18
amelius wrote: post #6

Refreshing. I'd like to see more "anti-survivor" articles so the survivor bias gets toned down.

Yep, I was braced for more failed-but-really-succeeded porn. This is a great read, and clearly from the heart.

> was braced for more failed-but-really-succeeded porn.

Isn't that what this is though? Sure he failed to build a billion dollar business, but his business is still way more successful than most. Lots of people would certainly kill to attain this level of failure.

I certainly recognise failure is a very personal thing, but from the outside looking in this looks like a success overall, even though I'm sure it was completely gut wrenching along the way.

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

#44

Post by sahillavingia »

jrochkind1 wrote: post #26
sahillavingia wrote: post #13

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 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

#46

Post by stillworks »

This bit is interesting...

"I am following up our conversation a few months ago. KP would like to sell our ownership back to Gumroad for $1. Can we discuss this week?"

...do founders discuss a Plan-B exit strategy/costs with the VCs ? Do VCs (or their lawyers) give this option or offer to discuss.

For Gumroad, it sounds as if this was a lottery or a happy coincidence. But I am interested in finding out if VCs actually only are interested in outright discussion of the up side (similarly for the founders... but that's kind of apparent from observation, and ... well also reading your article :-) )

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

#47

Post by uptownfunk »

This brings me back to a few lessons I’ve learned from other friends:

+One of the CEOs main roles is to raise money

+Rich or King? Know which one you wanna be.

+How much is your friendship really worth? Think carefully about this before you get in business with them.

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

#48

Post by freedomben »

sahillavingia wrote: post #13

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!

Haha, it was crazy reading the discussion (in 2011) around whether Gumroad should take Bitcoin or not :-)

https://news.ycombinator.com/item?id=2407053

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

#49

Post by saluki »

sahillavingia wrote: post #13

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!

Thanks for sharing your story.

I am a huge fan of gumroad, I remember your interviews on podcasts when you launched.

I have a couple Gumroad T-Shirts that are still my favs.

I have bought info products using Gumroad and it's a great experience.

Will definitely use you guys to sell my own in the future.

Thanks again.

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

#50

Post by ishjoh »

sahillavingia wrote: post #3
sixQuarks wrote: post #2

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.

I prefer not to do the math.

for what it's worth I think you've created more value at Gumroad then you would have at Pintrest :)
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