Reflecting on My Failure to Build a Billion-Dollar Company • Hacker News Board

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

#211

Post by austenallred » Thu, Feb 07, 2019, 8:55 PM UTC

wolco wrote: post #200

austenallred wrote: post #173

Earlier quoted context omitted.

> So he'll be worth $50M in a few years with Gumroad. That's my best guess, yes. > Meanwhile his investors lost all the millions they invested. Well, some sold his equity back to him for $1, so yes. > His employees lost all the time and vesting. Well the employees could have exercised their grants when they were laid off, but I doubt they were inclined to double down on what was then a failing company. > That's why i…

The employees got paid less because of vesting. It is a gamble and this story shows different outcomes for employees. Pinterest paided off and gumtree didn't. In both cases the founder made between 20-50 million.

Both employees and founders vest.

Founders own more of the company than employees, of course. The good news is anyone can start a company!

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

#212

Post by [deleted] » Thu, Feb 07, 2019, 8:56 PM UTC

Justsignedup wrote: post #201

ilamont wrote: post #196

I was basically alone. I didn’t have a team, nor an office. And San Francisco was full of startups raising gobs more money, building amazing teams, and shipping great products. Some of my friends became billionaires. Meanwhile, I had to run a “measly” lifestyle business. It wasn’t what I wanted to do, but I had to keep the ship from sinking. There's that term again, "lifestyle business." Uttered like a dirty word, wh…

"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.

[deleted]

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

#213

Post by pathseeker » Thu, Feb 07, 2019, 9:05 PM UTC

Retra wrote: post #189

kbenson wrote: post #66

Earlier quoted context omitted.

> 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 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.

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

#214

Post by michaelbuckbee » Thu, Feb 07, 2019, 9:06 PM UTC

ilamont wrote: post #196

I was basically alone. I didn’t have a team, nor an office. And San Francisco was full of startups raising gobs more money, building amazing teams, and shipping great products. Some of my friends became billionaires. Meanwhile, I had to run a “measly” lifestyle business. It wasn’t what I wanted to do, but I had to keep the ship from sinking. There's that term again, "lifestyle business." Uttered like a dirty word, wh…

I like and use the term "Bootstrapped Business" -> smaller, tight focus on profitability, trying to meet real needs.

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

#215

Post by anderspitman » Thu, Feb 07, 2019, 9:09 PM UTC

He links another post he made a year ago about moving from SF to one of the most conservative/religious cities in America[0]. Both were great reads.

[0] https://medium.com/@shl/from-bubble-to-bubble-21d86195e178

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

#216

Post by robterrin » Thu, Feb 07, 2019, 9:13 PM UTC

jmrobertson wrote: post #134

"Every month of less than 20% growth should have been a red flag." It's concerning that this is the state of affairs for expected business growth

Venture capital is broken. Plenty of other good businesses to create out there that don't have to do 20% month over month.

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

#217

Post by neya » Thu, Feb 07, 2019, 9:13 PM UTC

Dumbdo wrote: post #181

neya wrote: post #178

Earlier quoted context omitted.

Hi Sahil, Thanks for sharing the amazing story. I was wondering, since Gumroad's announcement about 2-3 years ago [1], is the plan to open source Gumroad still on track? Thank you. [1] https://twitter.com/gumroad/status/811650470758359040

From the the article in OP: > Soon, we will also open-source the whole product, WordPress-style. Anyone will be able to deploy their own version of Gumroad, make the changes they want, and sell the content they want, without us being the middle-man.

I missed that totally, thanks!

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

#218

Post by Kye » Thu, Feb 07, 2019, 9:17 PM UTC

sahillavingia wrote: post #84

bdcravens wrote: post #39

Earlier quoted context omitted.

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.

I'm sorry you had those interactions with me in the past! I think I've grown since, but it still sucks to hear that about past-me.

I've only had positive experiences. Very good human.

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

#219

Post by anxman » Thu, Feb 07, 2019, 9:20 PM UTC

Amazing post.

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

#220

Post by PhasmaFelis » Thu, Feb 07, 2019, 9:25 PM UTC

kokokokoko wrote: post #186

PhasmaFelis wrote: post #95

Earlier quoted context omitted.

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.

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, because he only needs one big success to wipe out all the failures, is glossed over.