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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

#371

Post by jstandard »

graeme wrote: post #307
jstandard wrote: post #257

Earlier quoted context omitted.

Agree the essay was a great read. I didn't see anything to suggest the OP missed that fact so much as had a reaction to a specific part of the essay and wished to discuss it. Being a part of the SV startup ecosystem myself, I also see the term "lifestyle business" used as a soft-perjorative for "not ambitious enough".

That's exactly how OP was using it though, with full awareness. OP's mindset at the time was "I failed: I meant to start a billion dollar business, and I only have a crummy lifestyle business" They now have come around and appreciate their success. Their use of "lifestyle business" was chosen to convey their own negative attitude at the time. The comment I replied to totally missed that the author wasn't critcizing t…

I see your point. The admonishment to Sahil at the end to "stop using" the term "lifestyle business" does seem to miss Sahil's self-awareness of the internal conflict between knowing about the misuse of the term and yet still allowing it to affect him at one point in time.

It's refreshing to see this perspective from founders. It's a story not often told and does well to characterize the grinding rollercoaster of hard decisions you won't easily find in the sea of "A-co raised $40mm!" press releases.

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

#372

Post by sctb »

the_cat_kittles wrote: post #259
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.

who gives a fuck. i wish people would say this more, especially on this site. stop worshiping money. why am i saying this here, on what is a 50% get rich quick scheme site? i dont know... i somehow enjoy the downvotes. if you offered me 200 million to throw away a couple years of my life at pintrest, the thrill of saying "no" would far outweigh the benefit of being a sellout. only do stuff that is cool on its merits…

We've asked you many times to please stop breaking the guidelines, so we've banned the account. We're happy to unban accounts if you email us at hn@ycombinator.com and we believe you'll start posting civilly and substantively.

https://news.ycombinator.com/newsguidelines.html

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

#373

Post by mindcrime »

retsibsi wrote: post #353
mindcrime wrote: post #167

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)

> "4 or 5" I'm curious now: is there a story behind this ambiguity?

Not really. I just don't remember exactly which years I went. I think I went to my first TSO show in like 2004 or 2005, and for a while I was keeping to a cadence of going every other year... but I haven't been for the past couple of years, and I've lost track of exactly how many times I've seen them.

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

#374

Post by chii »

hn_throwaway_99 wrote: post #336
sytelus wrote: post #313

Earlier quoted context omitted.

Let's run some numbers. Say you are VC putting in $1M in 100 companies. To your great luck all companies become self-sustaining lifestyle business. By definition, lifestyle business is making just enough for comfortable lifestyle of founder, so may be $300K/yr pre-tax. Let's say founder decides to give back 10% of $300K as return on investment. At that rate, it would take 33 years for VC to just recoup his original i…

Yes, but hopefully your average founder will wise up to the following: The chances of you being super successful, happy and content are much higher with a "lifestyle business" than a VC funded one. Why? Well, the biggest issue is that VCs can diversify (as you point out, have a lot of bets counting on a few successes), while founders can't. I think for the vast, vast majority of people, there are greatly diminishing…

> That is, if you have a 1/10 chance of having a $10 million payout, vs a 1/1000 chance of a $100 million payout

1/10 chance of $10mil is higher expected value than 1/1000 of $100mil. Of course anybody sane will take the former and not the latter.

I think you'll find the tune different if the latter had been 1/1000 chance of $1 billion.

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

#375

Post by chii »

PhasmaFelis wrote: post #220
kokokokoko wrote: post #186

Earlier quoted context omitted.

It is because a startup is an investment vehicle, not a business. If someone had X amount of dollars they want to maximize the rate of return on that wealth. The point of growth in investing is that you can see the future before it happens and pocket the difference. For example if I invest in company Y and they are growing at a certain rate, I can sell my portion of the company based upon expected future potential. I…

Indeed. I guess I should say, I understand the appeal for investors, I just don't get why so many founders are getting suckered into it. I suppose the investors are selling them a dream of fame, fortune, and early retirement, shored up with the implication that "if all these financial wizards want to invest in me, I must be on the right track." The fact that the investor expects most of his investments to fail, becau…

> I just don't get why so many founders are getting suckered into it.

because they either don't understand what's being done to them (after all, VCs can be very smooth talking), and the prospect of faster wealth gains for the founders also doesn't help.

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

#376

Post by the_cat_kittles »

sctb wrote: post #372
the_cat_kittles wrote: post #259

Earlier quoted context omitted.

who gives a fuck. i wish people would say this more, especially on this site. stop worshiping money. why am i saying this here, on what is a 50% get rich quick scheme site? i dont know... i somehow enjoy the downvotes. if you offered me 200 million to throw away a couple years of my life at pintrest, the thrill of saying "no" would far outweigh the benefit of being a sellout. only do stuff that is cool on its merits…

We've asked you many times to please stop breaking the guidelines, so we've banned the account. We're happy to unban accounts if you email us at hn@ycombinator.com and we believe you'll start posting civilly and substantively. https://news.ycombinator.com/newsguidelines.html

no thanks

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

#377

Post by hn_throwaway_99 »

chii wrote: post #374
hn_throwaway_99 wrote: post #336

Earlier quoted context omitted.

Yes, but hopefully your average founder will wise up to the following: The chances of you being super successful, happy and content are much higher with a "lifestyle business" than a VC funded one. Why? Well, the biggest issue is that VCs can diversify (as you point out, have a lot of bets counting on a few successes), while founders can't. I think for the vast, vast majority of people, there are greatly diminishing…

> That is, if you have a 1/10 chance of having a $10 million payout, vs a 1/1000 chance of a $100 million payout 1/10 chance of $10mil is higher expected value than 1/1000 of $100mil. Of course anybody sane will take the former and not the latter. I think you'll find the tune different if the latter had been 1/1000 chance of $1 billion.

But again my whole point is that expected value is itself a very poor metric to use for this decision, precisely because a founder doesn't get many "swings at bat" like a VC does. Even in the case where the expected value is the same, the fact that the actual value leads to 0 for all but the very, very, very luckiest/skilled means you get St. Petersburg paradox-like results.

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

#380

Post by talonx »

Retra wrote: post #360
chillwaves wrote: post #320

Earlier quoted context omitted.

It's called having a discussion. You felt like participating, why isn't the person you are replying to given the same courtesy?

Um... Because I don't believe "other peoples' assessment of your life is irrelevant to you."

That is your reason for not being courteous?
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