Sahil Lavingia

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A year ago I spent a Friday night designing a pencil icon. It took me four hours. At the end of it, I had a beautiful photo-realistic pencil. But I lost four hours. I really wished I had a Photoshop file before I had started, so I wouldn’t have had to spend four hours learning.

Wait a second…

I had a file! I followed a bunch of designers on Twitter. Maybe a bunch of people like me… followed me. I didn’t think this was a ridiculous assumption, so I decided to try selling that pencil icon.

It turns out, that was pretty hard.

There are traditionally two ways to sell something online. The marketplace model, which is the online equivalent of a megastore filled with small little shops. A souk. It didn’t make sense for what I wanted to sell, and the fees are normally pretty high. And then there’s the personal website model. That made more sense!

So I tried it. I spent many hours figuring out how to set up a simple HTML page that let you pay me $1. And then I created another page with the download link. And then I spent way too much time trying to tie in PayPal and building in security for the end link. In the end, I gave up. And I already knew how to code, I had a domain, and I already had a website set up! Ridiculous. Imagine my mom trying to sell something online? Yeah, good luck.

Why is selling so hard? Sharing is so easy!

If the ability to communicate, and to own your own distribution is now available to everyone, I felt as if the ability to sell should be too. Why was selling so much harder than sharing? In my mind, it shouldn’t be. The only difference should be a credit card form.

So I built it. That Friday night I called my mom, told her about it, and she told me to stop talking to her about it and just build it instead. So I did. I started working on it, and I spent that whole weekend obsessed with it.

I spent the whole day Saturday, and the whole day Sunday, building it. I picked the only domain I had on Godaddy that was generic enough for it, and had it ready to go by Sunday night. That was a fun weekend.

The launch.

I “launched” by selling that pencil icon. You can still get it today. I tweeted about it, and posted about Gumroad on Hacker News.

It did well. It got a bunch of upvotes and ended up getting around 50,000 page views on that first day.

There was something here! At the time I was full-time at Pinterest which was also doing (really) well so I put it on the back burner.

But that’s the story about how Gumroad came to be.

My life has been pleasantly crazy over the year or so. The best part about it all is the phenomenal people I get to meet. I am excited that it has been this long and they have yet to figure out how undeserving I am of their time and attention. But until then, I will continue to exploit it!

I was lucky enough to met Semil almost a year ago. Pinterest was just picking up steam, and he reached out. He was one of the first to start clueing into our growth. I met him for lunch and was surprised at how much he knew and (this is a million times more important!) cared about certain startups and the people behind them.

Over the past few months I have been working with him on a lot of the product and operations for Gumroad. It is my first time starting a real, legitimate startup from day zero, by myself. He has been tremendously helpful on almost every front.

He is the only official advisor to Gumroad. I don’t think I could have picked a better one. I get emails every day from people that want to be ‘formally involved’ with what I’m up to these days. That’s annoying. Semil didn’t even have to ask. He just did what I have seen very few do: risked his reputation to introduce me to those he trusted most and gave me a ridiculous amount of his time without wanting anything for it. He’s genuinely helpful. That is why he is so amazing. I couldn’t care less about his background or net worth.

I’ll stop being sappy. You should get to know him. He’s on Twitter as @semil.

Sometimes life gets really tough as a founder. Or as anyone, really. And sometimes it gets really awesome.

I have a note saved on my iPhone that helps me in both cases. It keeps me going and it keeps me grounded. I forgot where I got it from. Maybe I wrote it myself. Maybe it’ll help you.

You are the creation of everyone you have ever met, and everyone you have never met. Everything you did, you did because of them. Everything good, and everything bad. You are the least responsible for your success and failure. So just, do.

I really do believe it. Every interaction has shaped me. I am so grateful for everyone else. Even you, just reading, will impact me in some way… so thanks!

I get emails like this all the time:

“Tmmrw, 3, here?”

“conway”

“No.”

“y”

The first time I got an email like this, I felt like I got punched in the stomach. Someone really didn’t want to waste their time with me. Maybe they thought I was a joke. It turns out, neither was the case.

People are busy. Really, really, busy. Especially the people that have the brains you want to pick and the experiences you want to learn from. I used to think that terse emails came from douchebags. I’ve thrown that assumption out. Emails get shorter and more to the point when the sender is busy. But never worse.

I’ve started doing the above too. It’s a side-effect of this “email overload” you’ve probably heard about and maybe experienced.

Being blunt is OK. I actually like it. If I ask you a yes or no question, feel free to respond with one word. I’ll reply back if I need more than that. Or I probably would have asked for more in the initial email. I won’t read in between the lines, because I know people are honest and open about their thoughts. Bye-bye fluff, hello productivity.

When you get emails, read them like they’re written. If you want something, ask for it. But please, don’t think I’m an asshole. I just value my — and your! — time. I hope you do too.

I told a friend I wanted to write a book. He told me I should do it. ‘About what?’ I said. ‘About Gumroad. You have the tool to sell it. Try it!’

Well, I am. I’m going to document the process of building a startup from scratch. And I’ll be using my own product to do it! Yay, dog food. I’ll be as open and transparent as I can. I’d love for you to tune in.

It’ll be an interesting (ideally, many years long) experiment. I’ll release a chapter every month, starting today. Each chapter will be $1. It’ll provide an inside look at Gumroad and details I won’t reveal publicly (about things like raising money, investors, partnerships, and more!). All feedback (via email or Twitter), is appreciated.

You can get the first chapter, titled January 2012, here: https://gumroad.com/l/RwU.

Details:

• It’s about a new startup, called Gumroad. It makes selling stuff as easy as sharing a link.
• This is about January 2012. See here for pre-2012. It’s free.
• There will be one every month (released as close to the 1st as I can) until Gumroad is either dead, sold, or goes public.
• The title is a joke, but wouldn’t it be funny if it came true?