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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

#221

Earlier quoted context omitted.

"the number of phish concerts you went to" Yep. For me it's "number of Mötley Crüe concerts attended" and "number of Trans-Siberian Orchestra concerts attended". (currently "4" and "4 or 5" respectively)

My wife and I have missed the Trans-Siberian Orchestra every year for 10 years, but we REALLY want to go. It's almost a running joke at this point. This year I set about a dozen alerts that'll start going off at the end of summer to make sure I don't forget to get the tickets.

Oh man... I cannot recommend seeing TSO live highly enough. The music is amazing enough by itself, but the live shows - with the lights, the pyro, the video screens, and all the other "stuff" they do - are an absolutely amazing spectacle.

I'm also very happy that they've slowly been incorporating more old Savatage songs into their sets. :-)

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

#222

Earlier quoted context omitted.

"lifestyle business" is really just a small business that works, is self-sustaining, and not overly bloated to attempt to make obscene amounts of $$$. I feel like this is exactly what most companies should strive for. They'll make better decisions that way.

Most businesses should strive to be self-sustaining. And if they make obscene amounts of money, all the power to them. What I dislike is A) the view from startup land that there are only two types of new businesses, "startups" and everything else ("lifestyle") B) and the "everything else" category is somehow inferior or even some sort of hobby or vanity project. Sahil used the term to describe his own company, and at…

Keep in mind that HN is a website operated by Y Combinator, a company in the business of developing and launching startups that will raise more money through the VC system. The core business model involves encouraging companies to take more money at better valuations. If you view the startup world from the HN lens, it's all about the VCs and how to maximize their returns at all costs. Those incentives run counter to the values of sustainable profitability and doing right by customers.

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

#223
post #189

Earlier quoted context omitted.

Personal satisfaction doesn't matter once you're dead. Those other things do. And your entire assessment of your life at that point will be put onto other people. With that said, optimizing for after you're dead might be selfish and reasonably desirable, but there's a lot to be said for optimizing for tomorrow instead. Life would be pretty pointless if none of us were supposed to optimize for some enjoyment while we'…

>Personal satisfaction doesn't matter once you're dead. Nothing matters to you once your dead. Other peoples' assessment of your life is irrelevant to you. I would rather live my life happy with my decisions (part of which is helping people because of my own morals) rather than helping a bunch of people in ways that make me miserable.

One wonders why you have those morals if they mean so little to you. And if you don't need to justify your behaviors to others, why are you trying to justify them to me?

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

#224

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.

Why does his behavior on Twitter, good or bad, need mentioning here? What does it have to do with the article?

It feels like the new normal is for absolutely everyone to be in everyone else's good books. I'm sure a TON of people in the wild think they had bad interactions with you, online or offline. Does that really matter? Can one reduce you to any one of those singular opinions? Is one not allowed to make a mistake, because, the last I checked, humans were imperfect. Why make these trivialities a topic of conversation?

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

#225

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…

Exactly what I was thinking when I read that part. I hope those people are still his best friends. Working long hours for 9 months and getting laid off at the end doesn't only affect you financially. It will will have a significant effect on your personal life and the people around you who may depend on you.

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

#226

Earlier quoted context omitted.

Most businesses should strive to be self-sustaining. And if they make obscene amounts of money, all the power to them. What I dislike is A) the view from startup land that there are only two types of new businesses, "startups" and everything else ("lifestyle") B) and the "everything else" category is somehow inferior or even some sort of hobby or vanity project. Sahil used the term to describe his own company, and at…

Keep in mind that HN is a website operated by Y Combinator, a company in the business of developing and launching startups that will raise more money through the VC system. The core business model involves encouraging companies to take more money at better valuations. If you view the startup world from the HN lens, it's all about the VCs and how to maximize their returns at all costs. Those incentives run counter to…

Also, keep in mind that HN is mostly user curated, and represent the views of it's participants more than ycombinator itself.

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

#227
post #66

Earlier quoted context omitted.

I love your story Sahil, it is so true that people equate 'wealth' with 'success' but that is short sighted. If you step back and look at the big picture, you're on this planet for anywhere from 70 to 100 years, and at the end of that time there are two metrics, the number of people you helped and the amount of wealth you amassed and held on to, which number is a better representative of 'success'? Working on things…

> at the end of that time there are two metrics, the number of people you helped and the amount of wealth you amassed and held on to, which number is a better representative of 'success'? Let's not forget personal satisfaction. I'm a little leery of putting the entire assessment of my life onto other people (even though if I was going to, I could do a lot worse than number of people helped). Hopefully helping other p…

> personal satisfaction

You can be one of the people you help.

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

#230
post #17
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…

Yeah it appears this is a perfectly fine and successful business... it just went through an odd route for someone to figure that out. Those charts and numbers, all pretty good IMO. If someone came to me and said "Hey I (or we) made this thing here is what it does and the numbers." I'd be all about high fives and such. And yet at times they didn't think so based on the route they went, very interesting. I always wonde…

>I always wonder if there is value lost in companies that are shuttered because something isn't the next big hit, or some private equity decides they want to cash out / break up a company that otherwise... would be just fine and would have continued contribute.

Of course there is, but you have to compare it with the opportunity cost of working at something world-changing.

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