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.

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.

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!

“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.

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?

It’s super easy to implement, just copy and paste this line into your site’s pages (requires jQuery):

<script type='text/javascript' src='http://sahillavingia.com/sopa.js'>
</script>

That’s it. Please use it! And free to modify at your own will and host it elsewhere, if you want to — for security reasons, it’s good practice.

The way they do that, is to use Facebook’s single sign-on against itself and, using that as a starting point, build an app that creates a more valuable social graph (to users, but also advertisers).

The answer is most definitely mobile, and it’s interesting to see what people are trying out.

Address book

People need a better address book. There is a flaw when everyone (or even, every device) has to maintain its own set of contacts. There should be one huge database, and any update should be synced to those devices that have permission. Everyme is an attempt.

Events

Events suck on Facebook. They are really bad. They are very stupid, and have (at least from what I can see) zero intelligent features. Events that I may want to go to. Events nearby. Things like that. And the events + mobile pairing is huge. This makes a lot of sense. The most appealing thing about this is that a business model can be built-in from the beginning — charge for paid events, and take a cut. And events are very indicative of your true social graph. Someone will nail this. Whim is trying this route.

Photos

Photos are also extremely indicative of your social graph, but arguably less than events; mainly because you can take photos of lots of things (events, friends, celebrities, pets, animals, scenery).

I don’t like photos because I think people only take photos of notable things. Whereas I think my social graph would be better made up of seemingly irrelevant things (‘lunch in 5?’ — ’last night was… you ok?’). Batch is the most obvious one doing this.

Questions

I do ask my friends questions, and I think this could work really well. But no one is doing it well. Quora is making an attempt, but not with the same goal. There are some interesting prototypes floating around that do this in a more friendly way, but nothing that is launched yet. I think this is actually very interesting though. Think about how you communicate with your friends — what’s up? how are you? how was last night? I think whoever does this in the right way is going to have a good chance of becoming really big.

Group messaging

This was all the hotness pretty recently. No longer! I think this is far too easy for Facebook to own if they see an explosive competitor. This will almost definitely not work. Sorry guys!

–

This is all super interesting to watch, and these are just a few. I’d love your thoughts! And can you think of other ways?

I think 2011 was a good year, relative to the past. My top 5 accomplishments for posterity:

• Joined Pinterest.
• Left Pinterest.
• Built turntable for iPhone.
• Moved to San Francisco.
• Started working on Gumroad full-time.

I want 2012 to be better than any previous year. My top five (public) goals for the next year:

• Get Gumroad to significant usage/traction and growing every month.
• Hire a few people to join me!
• Become more influential and well-respected in the industry.
• Get a driver’s license.
• Get fit.

What are your goals?

Coming into 2011

I had had a few successes (Dayta and Color Stream mainly) and was contributing to Hacker News like a mad man. I had just started blogging and created the first iteration of this site to start my ‘personal brand,’ as they say. I had just learned Python, but was far more proficient in iOS design and development. I was joining Pinterest, a tiny startup in Palo Alto at the time, as a member of the founding team, to do design and all-things-mobile.

During 2011

My year was crazy. The good kind. When I got to the Valley, I could feel my serendipity-constant increase. It felt great. I could finally start acting upon the tens (maybe hundred-plus) emails to meet-up that I couldn’t take anyone up on. Now I could! And I did. I think I met someone (often, multiple people) almost every weekend day. And Pinterest went from tens of thousands of users to many millions. And the product became a million times better.

In August I decided my life wasn’t crazy enough, decided to leave Pinterest, and started figuring out what I wanted to do. I was pretty sure it was my own thing. I did do a little bit of contracting work in the meantime, mainly for fun and to see how other startups worked. The most notable is turntable‘s iPhone app.

Now

In September I decided I wanted to take Gumroad, a small side-project of mine at the time, full-time. It was the one idea I had that I could see myself working on in ten years. Since then, I’ve worked exclusively on it. It is getting better every day. It is growing every day.

I am excited by the opportunities I have had and the ones I have taken. Tell a-year-ago me about what I was up to and who I was able to meet in 2011 and he would have laughed.

And I think 2012 has a good shot at being even better!

Ask the same question to a bunch of Montessori kids and you’ll get a very different result. Like, a birds-eye view of someone wearing a black sombrero in the snow. Stuff that is far more creative than the stuff I considered, but makes sense in hindsight.

That’s how I feel about starting a company. You almost need to be inexperienced and ignorant to be really successful. There are tons of experienced people trying to solve the same problem, and sometimes the solution starts by looking completely impractical and kind of ridiculous. It ends up being the right answer.

There’s a story about Google that I really like. Larry and Sergey had the idea to index the structure of the web using links. They asked one of their professors, What do you think? We think it’ll take a few weeks.

The professor, much more experienced, thought it was impossible, but didn’t want to ruin it for them. In fact, I’m sure others had the same idea they did, but it was impossible. It took longer than a few weeks, but it happened.

I think the best things happen when crazy people believe in crazy things and slightly less crazy — but more experienced — people try to guide them.

What do you think?