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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

#31

Post by kaybe »

duxup wrote: post #19
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…

I always think of the market as ... all those shitty services and websites I absolutely hate / or just don't like ... that i still use because I want the service. Arguably they failed to execute some of what they did (their actual app or site) very well, but it doesn't matter, they picked the right market because I can't stop using it even in the face of other things.

Give us some examples of what you're trying to do, maybe someone here will help you in the future.

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

#32

Post by dawhizkid »

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.

If there a year at least vested one year of equity...?

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

#35

Post by asaddhamani »

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?

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

#36

Post by kickopotomus »

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.

Hindsight is 20/20. A million different factors outside of your control could have led to different outcomes for both Pinterest and Gumroad. Thank you for sharing your story!

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

#37

Post by bdcravens »

> The next year was not fun: I shrunk the company from twenty employees to five. We struggled to find a new tenant for our $25,000/month office and focused all of our remaining resources on launching a premium service.

Ouch. Even at 20 employees, $25k a month is insane when you have no profit. I'm sure it was a pretty office, the kind that attracts good developers in a competitive market.

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

#38

Post by chosenbreed37 »

dawhizkid wrote: post #28
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.

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.

> 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.

Mmm...based on the valuation even 0.1% would equate to $10 million...not bad ;-)

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

#39

Post by bdcravens »

the_other_guy wrote: post #33

I am not sure whether he's really serious or this is a long false modesty article about himself

I've had some interactions with @shl on Twitter where he seemed a bit full of himself (a few years ago - I didn't realize he was so young, so that probably had a lot to do with it). However, he could, and most would, have cut and run and found the next opportunity. Not doing so probably cost him millions of dollars; that's pretty authentic in my book.

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

#40

Post by avip »

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!

Thank you for sharing your story. It was inspiring to read.

Couldn’t quite spot the failure though... maybe ESL thing.

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