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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

#171
post #115

> On top of that, our product ideas, like our credit card form and inline-checkout experience, have proliferated the web, ... I've used Gumroad several years ago (as a customer), and the simplicity of the transaction and this interface was something refreshing. You also say that you'd make Gumroad open source soon. May we know what the tech stack behind it is?

From their calls for part-time/contract devs, I think it's largely a Rails stack.

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

#172
This idea that “people think billionaires are evil” is such a toxic straw man. “People” think that no one person is generating a billion dollars in value, and while being heavily rewarded for your decisions is fine, it’s not fine when it is at the expense of our politics (lobbying/super pacs), small businesses/innovation (Bill Gates tried to DESTROY open source, and many smaller companies) and providing for our people fairly.

It’s also ridiculous that Bill Gates gets to decide when and where we donate our money and to what causes. These billionaires need to be taxed and their money needs to be democratically distributed.

Also, look at every major players wiki... they all call themselves philanthropists, it’s a grift.

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

#173

Earlier quoted context omitted.

He owns the majority of Gumroad. Let’s say he had 100 basis points of Pinterest, call it 50% dilution, he’d walk away with $50m. That’s probably very generous, probably actually closer to $20m. Gumroad will be worth that in a few years at this rate, and he could cash million dollar paychecks along the way if he wanted.

So he'll be worth $50M in a few years with Gumroad. Meanwhile his original investors lost all the millions they invested. His employees lost all the time and vesting. Ouch. That's why it's way to dangerous to just follow any guy and do a startup and waste a few years of your life.

> 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 it's way to dangerous to just follow any guy and do a startup and waste a few years of your life.

I mean, the employees got paid all along the way, and probably not that much less (if any) than they would have working for another company, and they got to work on something they loved.

Sad that it didn't work out. These things are risky, but having worked at startups and not gained anything from the equity I would do it again in a heartbeat.

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

#174

Earlier quoted context omitted.

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 ;-)

[deleted]

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

#175

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!

Hi Sahil, I don't know why but I see you a lot in my LinkedIn feed. Hope you succeed even more in building Gumroad. Just visited Gumroad for the first time. Here is some of my feedback based on initial impressions. 1) The homepage seems to be designed around creators and not customers. It's trying too hard to onboard creators while ignoring the main source of revenue for the entire ecosystem, the customer. 2) The search bar for products is not very useful. It felt like I already need to know what I wanted to buy. There should be an alternative way for discovering, for example, top 10 selling items in each category. Like the first page a customer sees when visiting Amazon. 3) The review system although designed to help customers make more informed decisions, is not useful at this point in the product cycle. I could only find 5-10 ratings on every product. Compare this to the several 1000 reviews on Amazon products makes me scared to spend money on Gumroad. I don't want to be too critical of the product but I feel like your motivations are genuine and hate to see you struggle. So, wanted share some honest feedback.

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

#176

I’m incredibly grateful for Gumroad - Lambda School (YC S17) wouldn’t exist without it. We threw up a my book on Gumroad because why not/it was easy, and now I believe we’re sitting north of $100k in sales. I don’t think we would have put it anywhere else - wasn’t worth the effort. I often think about how important it is to remove even the slightest amount of friction as a result. I also find the move from KPCB admir…

It's interesting how Lambda School was able to capitalize on investors pumping cash into and hyping up Gumroad. It's a smart move to capture some of that VC money without having to pitch anything to them.

Not sure that entirely follows; Gumroad may have existed whether VCs pumped money in or not, but I hear what you're saying.

In a way every time you ride in an Uber or Lyft you're capitalizing on investors pumping cash into companies.

Luckily the winners make enough to pay for all the losses of the losers.

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

#177

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'? But of course those are highly correlated - it's easier to help a lot of people if you have plenty of surplus wealth and time to share out. I'd imagine that Warren Buffet will end up helping more people that almost anyone else in the…

I couldn't possibly disagree more. For starters, I think the majority of those who accumulate massive wealth do so at the expense of countless others. Buffet is an excellent example, actually. As probably the premier monopolist of the late 20th and 21st centuries, he has played a huge role in consolidating industries and destroying US wage growth. That's probably the single most detrimental macro trend in terms of quality of life over the last 50 years. His charitable donations have been fantastic, but the man has truly been a parasite on economic growth for his entire career. I would have a hard time believing the good offsets the bad in his case.

But in addition to that, there is absolutely nothing to suggest that the extremely wealthy are generally a positive force in society. Many give nothing or close to nothing back, and often work against the interests of others in so many ways (trying to decrease their own tax burden, hoarding wealth in assets, disproportionately damaging the environment, etc.)

Americans in particular worship the wealthy, but I really believe that it is utterly misguided.

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

#178

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!

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

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

#179

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…

If gumroad became a billion dollar company you'd be retiring on that 9 months of work with even a tiny bit of equity. I bet there are plenty of people that bailed out of google, facebook or other similarly positioned startups at that stage and regret it.

I bet there are far more people who didn't leave similarly-positioned-but-unsuccessful startups and regret it... maybe spurred on by the survivorship bias (or non-survivorship bias, in this case) of those who left a successful startup.

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

#180

I struggle to see how this story is one of failure. A kid launched a business that is still going 8 years later. He learned that VC funding is a double edged sword and was able to shed some of that burden - buying them out for $1. In the beginning he speaks of building this thing and having it be his lifes work - which it may well be if he keeps going. And yet there was all this talk of being a billion dollar company…

I think it's simply a byproduct of silicon valley's fetishization of the word "failure". Anything that isn't a runaway success is re-contextualized as a "failure" so that it can function as blog title short hand for "here's what I learned from my experience that didn't go 100% as expected".
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