On Starting a Startup

We launched Upworthy 99 days ago on March 26. We started as a company two months earlier on January 30. There were various news stories written about us as the team was being built, as we launched, and a month after we launched. Read those if you’re not familiar with our story. What follows are some of my thoughts and reflections on the experience of starting a startup.

Choosing a Technology

The engineering team started out as a team of two: the CTO and me. I was anointed Founding Engineer. My background is in Ruby on Rails, but in recent years I’ve soured on it a bit. Eric, a colleague of mine when I was at the Sunlight Foundation started using Sinatra for all his projects, and he seemed quite happy. So after some evaluating and thinking, Tim and I settled on Padrino, a framework built on top of Sinatra that incorporates most of the best parts of Rails.

At the end of our first day as a company, I made sure to create a paid private account on GitHub, generate a skeleton Padrino app, and push the initial commit.

I’ve been very happy with our decision to build on top of Padrino. The built-in admin interface was a huge time saver when building towards the minimum viable product, and nearly every major Ruby library out there is compatible with Padrino and Sinatra. Some of the technologies we use are:

We launched on Heroku, and while I’m not as happy with that decision as Padrino, I’d still recommend Heroku for startups like us. There’s been some widespread downtime in recent weeks, but some of the blame can be shared with AWS. For a startup with limited sys admin resources, Heroku makes much more sense than directly managing AWS services. Yes, we do have to architect our app with Heroku in mind, but it’s not nearly as severe as hosting on Google App Engine. There’s always been a reasonable solution for what we want to do.

Buying the Domain

Naming our website and acquiring the domain was probably the hardest thing to accomplish. We stumbled on Upworthy very late in the process. It was preceded by weeks of head scratching and hair pulling because the domain name industry is completely broken. It’s been reported that if Obama wins a second term, he’ll try to reform The Drug War. Well, I hope he also tries to reform the domain name system and disband ICANN. There are too many good domains being squatted on. Offering seemingly large amounts of money to those domain squatters is fruitless. They call themselves “domain investors” and believe that they’re a legitimate market force. But all they’re doing is stifling innovation, enabled by a broken institution in ICANN.

When we settled on a name (not Upworthy) a few weeks into the project, as the first technical hire, I took on the responsibility of securing the domain for us. It was expiring in the middle of February. After doing some research, it was clear that I wouldn’t be able to just register for the domain name manually on the day it became available. So I dutifully registered on the Big 3 backorder services. The domain backorder market is a rigged game, where those companies have deals with registrars that give them the first crack at registering domains the millisecond they expire. And when multiple people register a backorder on the acquiring backorder service, there’s an auction held for a few days and the domain goes to the highest bidder.

It’s capitalism at its not-so-finest. We braced ourselves for an auction.

On the expiration date, the moment of truth came (for .com domains it happens at 2pm ET). And it went. None of the backorder services I registered with picked up the domain. Instead the domain name was snatched by a service called BackorderZone, which I had never heard of. And we were left out of the auction, because only people who bid on the domain on the winning service before it’s snatched up get to participate. I felt like a complete failure. We tried to negotiate with the ultimate winner of the auction, but it didn’t pan out.

At that point, we already had a design, a brand, an app, and a logo. But we had no domain name. After some desperate brainstorming sessions, the name Upworthy came to Eli as he was on a run, and we quickly went with it. It was close enough to our initial choice that we were able to launch just two weeks later.

So what are the lessons here?

If you’re going to try to negotiate for a domain name or snatch an expiring one, realize that the chances of you obtaining it are actually very small, unless you’re willing to spend six figures. If you try to snatch up an expiring domain, use BackorderZone. The operation is just one guy in Pennsylvania and apparently he knows what he’s doing.

But I recommend not playing that game at all. Make up a new word like we did. Combine two short words. I think we lucked out by not getting that first domain name, because I think Upworthy more accurately connotes what it is we’re trying to do.

Facebook: One-Fifth of the Web

So what exactly are we trying to do? We want to make stuff that matters as shareable and viral as funny pictures of kittens. And these days, that means optimizing for social networks. Particularly Facebook.

As a software developer and early adopter, my social network of choice is Twitter. And Upworthy certainly has a strong presence on Twitter: a following of 10,000 built up in the last 100 days. If you do a real-time search for “upworthy”, you’ll find a constant stream of tweets linking to us.

But Twitter traffic simply doesn’t compare to the traffic we see from Facebook. I could tell you that Facebook is like the Sun, and all the other social media sites (Twitter, Reddit, Pinterest, StumbleUpon) are like the planets. But then you’ll probably picture something like this:

That’s actually not to scale. Because in reality, the Sun is unfathomably huge. This more accurately depicts Facebook’s dominance:

One in five web pages loaded is a Facebook page. Until I started at Upworthy, I didn’t appreciate how nearly everyone is on Facebook. Normal people. It’s truly a form of mass media, and the other social networks we frequent like Twitter and Reddit aren’t in the same league. Facebook, whether you like it or not, is the present and future of the Web. If you’re in the business of spreading ideas, knowledge, and information, you’d be sorely mistaken to ignore it.

You know about the Like button, but here’s a tip: It’s not very effective. Use their (deprecated) Share pop up instead. Shared items make it into friends’ news feeds, not liked items.

A Lean Startup

I love the taste of the Lean Startup Kool-Aid. I’ve found the books so important that I own both Kindle and paperback versions of them:

The Lean Startup methodology is a great way to think about building a business. It provides much needed structure in treating a business as an experiment. Make hypotheses. Run tests. Prove hypotheses with data and results.

As an engineer, I’m not too involved in the day-to-day of running the business. But I’m glad for the knowledge gained from the Lean Startup movement.

Two Memoirs

At the beginning of my time at Upworthy, I relaxed at night by reading iWoz, the autobiography of Apple co-founder Steve Wozniak. Woz was responsible for engineering the Apple I and Apple II. He essentially invented the personal computer as we know it.

I never quite adored a book until reading iWoz. It’s probably the favorite book of my adult life. Woz is kind, honest, and intelligent, and that all comes through on the page. People like Steve Jobs end up running multi-billion dollar companies, but they can’t do it without people like Woz. He simply wanted to make awesome stuff. There was one passage in the book where Woz talked about his creative process: He’d think and think on a problem for days, and when he came to a solution, he’d implement it quickly in a matter of hours. That’s how I work, and it was re-affirming and inspiring to read that I shared that in common with him.

I read another book, just in the last week, called The Boy Kings. It’s a memoir of Facebook employee number 51, Kate Losse. She started out in customer service and worked her way up the company over the course of several years. It’s an engaging, well-written look inside Facebook as it grew, and it most clearly describes the “brogrammer” culture that pervades tech startups.

It’s a bit of an anthropological study of the “boys” of Facebook, as Kate refers to them, viewing them and their project with a critical eye. Obviously, Mark Zuckerberg is described in great detail, but I was most fascinated by the descriptions of co-founder Dustin Moskovitz, the world’s youngest self-made billionaire. He’s portrayed in the vein of Woz: genuinely kind, perceptive, and a hell of an engineer. While Mark schemed up plans for world domination, Dustin was busy making sure the site stayed up. The memoir is from the view of just one person, but I can’t help but think about how different Facebook would be if Dustin was the CEO and not Mark. And it led me to think about how different Apple would be if Wozniak led it and not Jobs.

Those two memoirs drove home two important points for me: First, that I want to be an engineer in the mold of Dustin Moskovitz and Woz. I respect them infinitely more than I respect Zuckerberg or Jobs. And second, technology companies really do have the power to change the world. Apple and Facebook aren’t just companies; they’re institutions. Both books tell the story of how those institutions were built.

Upworthy is about to complete its first hundred days. I can’t wait to see what the next hundred days, and then the next thousand days bring for us. I’m thrilled to be at the ground-level, as we build something that’s trying to change the world in our own way.

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