Sam, you have a history of starting renegade companies. What services that you’ve created in the past are you most proud of?
I started 3 companies in the last 10 years. In each case, I was passionate about bringing a community of people around free products or online services and in particular, products and services which had traditionally been paid for by consumers.
My first company was called SparkNotes and we took the idea of Cliff’s Notes as a line of study guides which have been around for 50 years. My partners and I started SparkNotes back in 1999. We grew it to be the largest brand of study guides on the web. We ended up selling the company to Barnes & Noble and they built it into the largest offline series of study guides as well.
After SparkNotes I teamed up with another friend of mine who had started a company called eDonkey, which was a peer to peer file sharing application, which we grew into the largest file sharing network in the world.
We ran this company until 2006 and while it was winding down I got back together with my co-founders from SparkNotes and we decided to start OkCupid. We believed that the Match.com business model was not right. They did not really think about modeling online dating to offline dating.
First, we looked at how people go and date in the real world. In the real world dating is social. One girl will call up her girlfriend and say, “Hey, let’s all go out tonight.” They all get dressed up and they never explicitly say, “Hey, we’re looking to get picked up by a guy.” They just tell themselves that they’re going out to have a good time. No one had ever invited me to join Match.com. No one ever said “go to Match.com, you’ll have a great time”. Match.com was a very lonely experience. So our vision from the very beginning was to build an online bar, a place where you go with a bunch of friends, you observe other people and decide which ones seem the most appealing to you. Then you gradually and slowly begin to strike up a conversation with them.
We also take matching very seriously. If your friend tells you he knows a great girl, no matter how much you trust your friend, you’re going to ask him a series of questions before you meet her. We were able to model that process online by having users upload their own questions and then select their own desirability and weight those on a 5 point scale. So each person was customizing their own algorithm based on their preferences.
You have started another site recently called Crazy Blind Date. Can you tell us about how that came around?
The Crazy Blind Date story actually has its roots comingled in the founding of OkCupid itself. In 2002 my partner Chris came up with an idea to create a dating website where there was a blind date button. If you push the button, you are guaranteed to go on a date that night. Of course, the problem with the blind date button is, in order for that to work, you have to have a huge database. We always had this idea of the blind date button in our back pocket. A couple of years ago we started getting serious about it. We had a big enough site that we could make a blind date button work. A blind date button on OkCupid would be great but we thought that launching it as a standalone site would be really flashy and get a lot of press.
What would you say surprised you the most about the way internet daters behave? Have there been any shocking aberrations in human behavior that you really wouldn’t have predicted?
A lot of people look at a profile and they’re immediately looking for negatives. They’re looking for reasons to reject the potential date. In the offline world people tend to be looking for reasons to make it work.
How does OkCupid help people find somebody who is a match that they also have chemistry with?
There are two elements how we handle the chemistry issue. The first is the expectation. We’re not promising that our algorithms are going to look through all the profiles on our site and find the one who is the best for you. We’re trying to facilitate you going on first dates that don’t suck. The second one is the analogy of a bar I was talking about. On OkCupid there is a big opportunity to see someone over a course of time. We allow a lot of ways for you to express yourself.
So there seems to be a bit of a trend recently with free dating sites starting to charge. Isn’t advertising revenue enough?
It’s not about enough. It turns out that there are opportunities to make money off subscription fees and also off advertisement. We’re going to see a convergence of free and paid dating sites. If you’re on a site that allows you to just post a profile and then if you want to communicate you have to pay, you’re on a paid site. And if you can communicate for free, you’re on a free site. We want to be known as a free site, but there are a bunch of things that we can offer our users who are most serious to pay for a better experience and there are things that we can offer them that are premium.
I would love to know what your vision is for the internet dating industry. What is it going to look like in 2015?
We’re going to have one big free site, maybe two, and we’re going to have a solar system of subscription sites all around them. People will still go to e-Harmony for marital, people are still going to go to places for one night stands but there is always going to be this big free site in the middle that everybody feels they have to be on.