Web Masters Episode #35: Sam Yagan

Online dating may have come to the Web early,¬†but the team at OkCupid thought that those early dating websites were broken. That’s why they decided to build something better. Hear the full story on the latest¬†Web Masters Podcast:


OkCupid Unveils Provocative New "Ask Yourself" Campaign Highlighting the  Most Important Issues to Young Daters

Sam Yagan:

Now you fast-forward to December of 2002, we’re all living in Manhattan and I got a call. Chris was at a bar in the Lower East Side that’s called Sweet & Vicious I think. He calls me up. He’s like, “Sam, we need to start a company.” I was like, “Okay. What is that?” He’s like “I have an idea for a company.” I’m like, “Okay. What’s that?” He goes, “There needs to be an online dating site with a button.” He calls it the blind date button.

He said, “It would be amazing if you just go to the site, you just hit the button and all you do is you give your age, your gender, your orientation, and your zip code. That’s it. We will just assign you a blind date. We will tell you, ‘Meet at this bar at this time.’ All you’re going to get is the person’s first name. Whatever. 7:00 PM, you’re going to meet Sally at Sweet & Vicious.” I was like, “Okay. That’s cool. Sounds like a great idea, Chris.”

Of course, he had been drinking. He’s like, “What do you think?” I was like, “This sounds awesome.” He was like, “All right.” It was really loud and so he hangs up and I just shrugged and I’m like, “Whatever.” Chris and I BS about ideas all the time so I was like, “It’s just like any other idea.”

Aaron Dinin:

It wasn’t really just like any other idea, because the man you heard telling the story was Sam Yagan, co-founder of OkCupid, the dating website that pioneered the modern freemium dating website model. In other words, the idea you just heard for a blind date button was the idea that plunged Sam into the world of online dating. Are you ready to hear the story? Let’s get dialed in.

[INTRO]

Aaron Dinin:

Hello and welcome to Web Masters. This is the podcast that teaches about entrepreneurship by talking with some of the internet’s most impactful innovators. My name is Aaron Dinin. I’m a serial entrepreneur. I teach innovation and entrepreneurship at Duke University, and I have a confession to make. I’ve never actually used a dating website. I’ve never really needed to, not because getting dates was easy for me, but because I met my now wife before dating websites became mainstream so they just never really became relevant in my life, and fingers crossed, stays that way.

Still, even though I haven’t personally used dating websites, I’ve been studying their evolution for a while now because the adoption curve of online dating is fascinating. Online dating companies created some of the earliest successful commerce models on the web. Yet, for a long time, people using online dating websites would never admit to it. Fast-forward a few decades and these days if you’re single, you’re virtually expected to belong to at least one dating website.

How has online dating grown so much? We’re going to explore some of that history in this episode, but first I’m going to pause to thank this podcast sponsor. They’re kind of like a dating website, except they match entrepreneurs with online businesses. Web Masters is being brought to you thanks in part to the support of our partner, Latona’s. Latona’s is a boutique mergers and acquisitions broker that helps people buy and sell cash flow positive internet businesses and digital assets.

That could be a dating website. It could also be things like Amazon FBAs, e-commerce stores, domain portfolios, SaaS apps, and any other type of online work-from-anywhere company. If you’ve got a business like that and are thinking about selling it, be sure to contact the team at Latona’s. They’ve helped lots of people, just like you, sell their businesses for a great price. If you’re interested in buying an already profitable business, be sure to check out the Latona’s website, latonas.com, where you’ll find all their listings of businesses you can buy and start running right now.

That website again is latonas.com, L-A-T-O-N-A-S.com. Even though this episode’s guest, Sam Yagan, has had an enormous impact on the online dating industry, there’s something a bit different about Sam’s story of internet entrepreneurship compared with a lot of the people we’ve heard from here on Web Masters. Most of the people we talk with got excited about computers and the internet from a relatively young age.

That’s actually not the case for Sam. Not that he hated computers or anything like that, but even as a kid, Sam never saw computers as being particularly special or unique, and that’s because unlike most people in the early 80s, he grew up basically sleeping next to them.

Sam Yagan:

My dad was an engineer, a programmer I guess they called it at the time. He went to college in the 60s before they even had computer science degrees at most schools. His degree was in math, but ended up learning computer science. I remember one of my earliest memories was actually, he would take me into the office sometimes because he could only reserve mainframe time late at night. I would go into the office and I remember sleeping under his desk while he would be putting punch cards or whatever into the mainframes. That’s one of my very first memories of a computer.

Aaron Dinin:

What about the internet? When did you first start using that?

Sam Yagan:

In the early 80s. I remember my first internet recollection was on a modem where you had to stick the phone into the thing and it would make those crazy sounds, the static sounds and bells. I think the idea of being able to connect to another computer, it struck me more as annoying I think in my very earliest times. There was no benefit to it. It was just this thing I had to do to accomplish the goal.

Aaron Dinin:

That familiarity with computers would carry over into college for Sam when he moved to Boston to attend Harvard. Again, unlike a lot of the people we’ve heard from on Web Masters, Sam appears to have been mostly unfazed by what was in reality a monumental shift. If anything, he was surprised more people weren’t already as digitally inclined.

Sam Yagan:

In the 90s when I was in school, I remember going to the library and they taught us Gopher to get information from other libraries, which also just seemed incredibly inefficient. Can’t I just go to the encyclopedia in our library? Why am I gophering to University of, whatever, Colorado? Of course, we used text-based chat, which seemed amazing at the time. I think those were all my very early times. That was the first class in my college where you actually got assigned an email address.

I remember learning that and I remember that feeling like a big deal. There was this seminal change that was happening, that, okay, now everybody gets an email. I had already had an email address so it wasn’t as big of a deal. I remember being a little bit surprised that prior … This would have been the fall of ’95, that people weren’t already getting email addresses assigned, and that it was now a big deal that people were.

Aaron Dinin:

I’m highlighting Sam’s relative indifference to the ways computers were changing the world around him, because I worry sometimes the entrepreneurial community gets carried away with what we might call the mystique of the visionary. It’s the Bill Gates, Steve Jobs, or Elon Musk type of person who appears to see the world in some sort of unique and revolutionary way before everyone else. That’s what allows them to become wildly successful entrepreneurs. Well, that might be true, or it might be a bit of retroactive narrative.

The point is, you don’t have to be a cutting-edge futurist to build great companies. You can be like Sam, a wildly successful entrepreneur who was even a bit skeptical of the first entrepreneurial opportunity that came in front of him. That opportunity appeared when his friend at Harvard and future OkCupid co-founder, Chris Coyne, showed Sam a website he built called thespark.com.

Sam Yagan:

I remember he came to me in the fall of our senior year and he was like, “Hey, Sam, check out this website I made.” The closest comp that anyone would know now is The Onion. Just think of The Onion, not exactly that, but that’s the closest thing out in the world. It was this humor site and Chris wrote these funny articles and I read them and I laughed. I was like, “Okay.” It at no point struck me as a business for sure, or even something that was durable or viable, something that you’d want to do other than just kind of thing on the side. I was like, “Ha ha, very funny.”

Then I went back interviewing with consulting firms for my job. The winter break came and went and then in January he said, “Hey, have you checked out my website recently?” I was like, “No.” He’s like, “You should check it out.” I checked it out. It was just more funny articles and he had added a purity test, which was all the rage at the time. Okay. Whatever, I still don’t get it.

Then he was like … I forget the exact number, but he’s like, “Hundreds of thousands of people come to the site every month.” I remember being like, “That’s a lot of people.” I still was like, “I don’t get it, other than you’ve written some funny articles that lots of people read, whatever.” Chris was like, “I think we should do this.” I remember that exact sentence. I think we should do this. I literally said, “Do what? What is the this in your sentence?” He’s like, “We should start a company.” I was like, “Okay.”

Aaron Dinin:

That didn’t sound like a very enthusiastic response. Why’d you agree to build a company with him?

Sam Yagan:

Because I remember thinking it would be fun and I would learn a lot and why not? It certainly wasn’t for money and fame and all the other things. It just seemed like a fun thing to do.

Aaron Dinin:

It’s here actually, where we can see something that’s a bigger indicator of entrepreneurial potential than being some type of tech visionary. Sam was willing to pursue a path with a lot of uncertainty. For me, that’s the defining characteristic for entrepreneurs. Most people crave predictability while entrepreneurs seem comfortable with unpredictable outcomes. What’s particularly interesting about Sam’s story is how he developed this willingness to thrive in uncertainty.

Most of the entrepreneurs I speak with tend to have a parent, close family member, maybe an early mentor who was ‘entrepreneurial’ in some way and that’s what helped facilitate their eventual journey to becoming entrepreneurs themselves. For Sam, that wasn’t the case. At least he didn’t think it was, until as an adult, he had an important revelation.

Sam Yagan:

It took me years of failing to answer the question of, what in your childhood led you to become an entrepreneur? Everybody wanted me to say lemonade stand and paper route, and all that kind of stuff and I just couldn’t answer that question for years. Then finally, I remember I was at a dinner with my parents and there was just this light bulb as they talked about their own upbringing. I was like, “Oh, you guys are entrepreneurs.”

Aaron Dinin:

What made Sam’s parents entrepreneurs? Well, they were immigrants.

Sam Yagan:

I would say the one exposure in my childhood that I think really set me up with the mindset of being drawn toward entrepreneurship was being the son of immigrants, because the life choices they made … I don’t think they ever said the word entrepreneur to me, but they gave up a life of relative comfort. Granted it was in Syria, so not comfortable today, but at the time they were upper class, landowners, well-educated.

They gave up a relatively comfortable alternative to come to a country where they didn’t speak the language, didn’t have the credentials, didn’t have any money, all for some incredibly speculative long-term undescribable, unspecific outcome. There’s going to be a unicorn. Years from now we’re going to build this family into a unicorn. But at the time it was all sacrifice, sacrifice, sacrifice. Their families ridiculed them. They took crazy, in retrospect, undue risk. I don’t know about undue. They took crazy risk.

So when my parents have talked about, “We left our family. We came with no money. We didn’t know the language. I had to go to med school again, but it was worth it.” That mentality of, it’s worth it to sacrifice for the things that you want, that made the idea down the road when the prospect of giving up my lucrative consulting to start a company, that made it seem, “Okay. Well, I’ve seen that kind of trade off before.”

Aaron Dinin:

I love this comparison of immigrants and entrepreneurs. It’s a great reminder that entrepreneurial action and an entrepreneurial mindset can be applied to all sorts of things beyond business building. It’s also a great reframing of what immigration is, and perhaps even offers a unique way of rethinking questions around immigration policy. That I suppose is probably a topic best left to another podcast.

This one is about internet history and the people who made it, which brings us back to Sam, who actually made his first mark on internet history, not with OkCupid, but by joining forces with Chris and a couple other friends in order to turn thespark.com into an actual business.

Sam Yagan:

We incorporated it as thespark.com. That’s the business we were starting. Then literally before we even got our incorporation documents done, now that we looked at it with a business lens, we were like, “Ugh, being in the humor business, the humor content business is a crappy business. Even Saturday Night Live has crappy seasons. Do we really want to be in this business of content creation?” We were sitting in Chris’s room in his dorm.

We had looked through all the data and we realized almost all the people coming to the website were students, high school and college students. Chris had these CliffsNotes up on his shelf and Max, our other co-founder, Max just looks up and he goes, “We should make CliffsNotes.”

Aaron Dinin:

That’s how SparkNotes started the online version of CliffsNotes. It was Sam’s first entrepreneurial success, ultimately getting acquired by the book retailer, Barnes & Noble. Even though SparkNotes didn’t have any direct relationship to online dating, it was during this time the seeds for OkCupid were planted.

Sam Yagan:

I will say the part that we don’t talk about very often is we had this idea of Spark being this Omni-brand and so we had The Spark, we had SparkNotes and we actually created something called SparkMatch, which was our first foray into online dating. That part of the story never really gets told because when we ended up selling the company to Barnes & Noble, they wanted nothing to do with an online dating site so they killed SparkMatch in 2001.

We knew even at that time, when they decided to kill it, we said, “At some point we want to come back to this.” We learned a lot in that first foray into online dating in the late 90s, early 2000s.

Aaron Dinin:

As you heard at the beginning of this episode, those seeds of online dating continued germinating in the mind of Sam’s co-founder, Chris, and it ultimately led to his late-night call where he pitched his idea for the blind date button. It was an idea Sam didn’t take seriously at first. He assumed Chris had just had a few too many drinks, but that began to change the very next day.

Sam Yagan:

The next morning Chris calls me. He’s like, “So what do you think?” I’m like, “About what?” He’s like, “My idea.” I’m like, “What idea?” I had already put behind me that this was actually a thing. He goes, “The blind date button.” I was like, “Wait, are you serious?” He goes, “Yeah.” We get together later that day and then we basically spend the next six months, we had pizza at Patsy’s Pizzeria many times, and just worked on this idea of like, “Okay. What does the online dating space really need? What’s going on?”

Unlike with SparkNotes where we didn’t do any research and we almost on a whim just did it. We really spent some time understanding what’s out there. The world at that time was really Match and eHarmony, both either run by or affiliated with what I thought of as relatively lame psychologists. Dr. Phil was pitching Match and Dr. Neil Clark Warren hawking eHarmony. We ended up thinking for the blind date button to work you needed so much liquidity.

You need enough people so that when someone wants a date on Friday at 7:00 in a certain zip code, you actually have a large enough pool of potential candidates that you can actually meet that demand. We quickly realized that we needed a general purpose dating site first before we could launch the blind date button. The question really became, if you’re going to launch a dating site from scratch in 2003, what would you build?

Aaron Dinin:

What did you build? What did you see as the market opportunity in the dating space back in 2003?

Sam Yagan:

We came to a few conclusions or observations, I guess at the time. The first was, everybody else was what we called paid. They were only freemium in the most technical matter, in that you could create an account for free, but if you wanted to communicate with anybody you had to pay. That was the standard Match model and eHarmony model and Yahoo had a dating business too. Those three. The equivalent would be like you could go into the bar with duct tape on your mouth but if you actually want to speak to a girl, you have to pay.

It was only nominally free to join, but really it was paid. That was the first thing we want it to mess with. The second thing we wanted to mess with was if you look at any of the eHarmony or Match marketing materials, they all were premised on the idea that you as a single person don’t know what you’re looking for in a potential date. The value that an online dating business would bring, would be to look into your soul and say, “You are person of type A, B, C. You need person X, Y, Z. But for having come to eHarmony, you never would have known that on your own.”

Our observation was actually the opposite. Our observation was that, by definition, for as long as humans have been around, we’ve actually been pretty good at finding the person that you want to be with. Otherwise, we would be extinct. That is not our problem. The problem, especially in today’s society, is you don’t meet enough new people in your day-to-day life from whom to select that best person. You go to the same Starbucks every day. You go to the same gym every day. You go to the same school or job every day.

How many new single people of the appropriate gender orientation in your age that … You start going down the funnel, you’re like, “Oh, I only meet a couple people I would even consider dating anyway.” That ends up being the problem. Our premise, as we built OkCupid, was that the existing dating products were solving the wrong dating problem. They were helping you figure out what you needed, not helping you meet more people and they had the wrong business model.

They were forcing you to pay to communicate versus the business model we ultimately pioneered that Tinder and Bumble are now based on, which is this premium services model.

Aaron Dinin:

How’d you solve those problems? How did you help your users meet more datable people?

Sam Yagan:

My partner, Chris, is like a genius when thinking about human behavior and human interaction, and what he led us to do at OkCupid was basically to digitize what humans already did. Here’s what I mean by that. If your roommate from college calls you up and says, “Hey, I’ve got a great person I want to set you up on a date with.” You don’t just say yes or no. You ask a few qualifying questions and you might ask about age. You might ask about religion. You might ask about job. You might ask about pets. You might ask about travel. Who knows?

You’re going to have a set of filtering questions you’re going to ask and if you get the questions that are disqualifying, you say, “You know what? That’s probably not a good fit.” If the responses are in line with what you’re looking for, you say, “Yeah. That sounds great.” Each person has their own set of questions, their own questionnaire, if you will.

While you care most about your questions, you might also be interested in the questions I ask. “Yeah. Oh, I didn’t think about asking that question. That’s a pretty good question. Let’s include that too.” The product that we created was basically taking the heuristic that people already use to determine whether to date someone and simply bringing that online. Rather than us hiring psychologists to say, “Well, what are the right compatibilities among people?” We simply let people ask their own questions through the system.

Aaron Dinin:

That was the big distinction? Users could ask their own screening questions? Why do you think that was so effective?

Sam Yagan:

You could ask a question, put in a question to our system, “Do you play at least two hours of video games every day?” Somebody said, “That is a question I want a potential match filtered on.” The responses were yes or no. Each question got rated on a five-point scale from irrelevant to mandatory. The way a user of OkCupid would engage is they would create an account and then they would start answering these questions. Do you play two hours of video game a day? You would first answer it for yourself. I would say, “No, I don’t.”

Then you’d say, “Well, your ideal match, how would your ideal match answer the same question?” This allows me to determine, “Do I want someone who’s like me or dislike me on this axis?” It’s not obvious. Take religion, speaking for myself personally, I’m actually quite okay with my match having a different set of religious beliefs from me. I actually think that’s actually quite positive. I would like that, but my God, I don’t want the person to want to own a cat.

In my own personal matching algorithm, cats are more important than religion. Very open to religious views. Don’t want your cat, right? It’s very hard for a centralized system to capture that, right? Like eharmony’s model would have said, “Of course, religion is more important than pets.” In my model, it’s actually not. You can imagine, as people submit these questions, we ended up with tens of thousands of questions in the database.

You see someone floating naked in front of you, which is more interesting? That they are floating or that they are naked? Now, that question is not that important and everyone marked it as irrelevant, but it’s humorous. You can imagine there’s a lightheartedness that comes in these questions. Some are very serious about kids and marriage and religion and sexual identity and politics, and some are whimsical video games and floating naked people.

Aaron Dinin:

That floating naked people question is tough. I’d wonder why they were floating, but now I want to know what that says about me. I guess that’s my next question. How did these user-submitted screening questions help people find dates?

Sam Yagan:

In the course of this, your personality begins to emerge and we end up being able to, really based on your own assessment of who you are and what you’re looking for and what’s important to you, we’re able to take the millions of people in our database and simply sort them, rank order them, just like Google does. You do a search on Google, no one hits the I’m feeling lucky button on Google. Everyone looks at the full search results and you could go millions of pages deep if you so desire. Usually what you’re looking for is on that first page.

That was that same experience. We don’t want to tell you, “Here’s your soulmate.” We wanted to tell you, “Of the millions of people in our database, here’s the person we think is best for you, second best, third best, all the way down.” We have countless, countless, countless anecdotes from members who said, “I joined OkCupid. I answered some questions. I sent a message to the single best match on the system. Went on a date, got married.”

Now, that’s not the modal engagement with OkCupid, but very common occurrence of people who went on one date with their best match on the system and that was all they needed. That’s May of 2003. We started the company with this idea of being first and foremost free, and second, data-driven specifically in algorithmically decentralized way. We empower and enable each person to create a customized matching algorithm for themselves in a painless and in most cases actually joyful and humorous way.

Aaron Dinin:

Okay. I get the theory behind why OkCupid could work better as a dating website, at least at first, but logistically you’re still stuck with a site that requires a network in order to be useful, right? Without users, nobody can get dates, and if nobody can get dates, you won’t have any users. It’s the standard chicken and the egg question, which means the problem you had with the original blind date button concept is still there. You didn’t have an audience yet, so how did you solve that issue?

Sam Yagan:

Yeah. I think especially true in any network effect or marketplace businesses. If you’re just selling a widget and you don’t need any network dynamics to succeed, I think it’s very straightforward. You create some widgets, you can buy one-off marketing, you sell widgets one at a time linearly, and then you make more widgets then you sell more widgets. Network effect businesses, whether it’s LinkedIn or Facebook or OkCupid or whatever, can’t work that way because your bucket is so leaky early on that the first person you bring to your website, if there’s no one else to search for, leaves.

By the time the second person comes to the website, that first person has left and you still don’t have anyone on your website and you just have this cold start, bootstrapping, whatever you want to call it, problem where you can just never get enough critical mass at one time to actually build the network. Chris Coyne, my partner, who I already described as a genius had the idea.

This I think ends up being a common bootstrapping strategy that many other companies end up copying effectively or being inspired by. Can we create an alternate reason for people to come to OkCupid before we explicitly tell them to come for dates? He comes up with the idea, and again you have to put yourself a little bit in internet history time. There was a period of time in the early 2000s, late 90s where personality tests were very, very popular online. What kind of dog are you? What kind of cat are you? Which president would you be? All that kind of stuff.

Chris had the idea for a dating personality test modeled loosely, but structurally on the Myers-Briggs test. There were four axes. I don’t even remember what they are now. That tells you how long ago it was. On each axis you were one of two poles. There were 16 male personality types and 16 female personality types. These personality types were incredibly nuanced, almost like any good astrology horoscope, very specific, but also very accurate.

What happened was he and Christian wrote this quiz and it became very popular. We had a little badge at the end that would have your personality type and the summary. This was pre-Facebook. This was in the MySpace days. People would take the widget and literally they would cut and paste HTML code and they would paste it on their MySpace page and so millions, literally millions of MySpace pages had people’s OkCupid dating persona badge on their MySpace page.

You don’t need a network for that. You just needed a place to take a quiz. For the first year you would go to okcupid.com and all you would see would be this test.

Aaron Dinin:

I see, that’s clever. OkCupid wasn’t a dating website at first. It was a compatibility quiz, is that right?

Sam Yagan:

It’s all it was. We were doing a couple of things. We were introducing our brand. We were collecting a lot of email addresses and we were contextualizing people in this dating context. We had a lot of people to write their own quizzes so we generalized our quiz engine so people could then create their own quizzes and their own badges. For the first 18 months, we were exclusively a quiz network, really. Then in early 2005, we turned the lights on, if you will, lifted the curtain all of a sudden said, “Ta-da, you’re at a dating site.”

We made it searchable. People could basically search the other people who had taken this dating persona test and begin to find and engage with other people. That was how we solved the cold start problem and how we artificially populated the database. As you can imagine, most people who are taking a 50% of test are single. Obviously there were a lot of people who weren’t and they were either outraged or simply deleted their profiles or whatever. For the majority of those millions of people who were single, we then had this dating site for people.

Aaron Dinin:

Just to be clear, it wasn’t an accident, right? You knew you were creating a dating website all along, even though that’s not what you built at first?

Sam Yagan:

Yeah. People often ask, they’re like, “Oh, did you stumble …” I mean, of course I can just tell you the truth, but the fact pattern is we wouldn’t have called it OkCupid if it was a general quizzing site. It’s a bad enough name for a dating site, actually in retrospect, but it’s a terrible name for a quizzing site. Definitely was in the cards the whole time.

Aaron Dinin:

If you’re an entrepreneur thinking of building a network effects type of business like OkCupid or a social network or any kind of two-sided marketplace, pay close attention to Sam’s story. In fact, rewind and listen to it at least five more times. Over the years, I’ve met dozens of entrepreneurs who have ideas for marketplaces and social networks and things like that, and with millions of users, their ideas would probably be pretty cool.

The problem, however, is how do they get users before enough people are on the platform to make it valuable? Sam is explaining the strategy. You’ll probably have to create value for those early users by offering something else entirely like Sam and the OkCupid team offered quizzes. Eventually, after OkCupid had built a large enough audience, the team was able to move those users to a dating website, but as you heard, it took 18 months.

Remember, that’s a lot of time to be working on something that isn’t even your final company. You might not even be getting paid for it. In the case of OkCupid, while the strategy worked well enough to get them launched, they still had a long way to go before they were successful.

Sam Yagan:

It grew quite nicely, but what it didn’t do was the kind of exponential growth that you can get in other categories. Before Tinder proved the ability to actually have exponential growth in dating, I wondered for many years whether dating just had ‘physics’ that prevented it. Maybe people left online dating sites when they had success, or they got sick of dating sites, or they didn’t talk about dating sites with their friends. I would say until Tinder, I was at least a contemplator that online dating sites could not grow virally.

Anyway, we were growing tentatively linearly. We raised some money 2006, and honestly, 2007/2008 were disappointing years for us. We tried to spur growth and we just couldn’t get it to grow. 2007 we tried to go international, which in retrospect is so dumb. Like, “Hey, we can’t figure out how to get growth in our home market. Let’s go to markets where we don’t even speak the language or understand the cultural nuance in dating. That’s a good idea.”

Then 2009, we finally launched Chris’ crazy blind date idea, which while it got us a ton of press also because of its very nature, it was definitionally a subset of the OkCupid user base that was using crazy blind date and so it wasn’t growing the OkCupid user base. Then there was the financial crisis of ’08. 2009 was the low point in probably all of our careers and was certainly the low point of our professional careers.

We actually began 2010 with a plan to just not give up on OkCupid, but basically leave OkCupid by the end of 2010. The four of us all got together and said, “Let’s just take 2010 and plan each of our successions.” Figure out who’s going to replace us in the company. We’ll let it just grow linearly for a decade and maybe in 2020, we’ll have a business that’s worth something.

Aaron Dinin:

Clearly you figured something out eventually. How’d you turn things around?

Sam Yagan:

I always hate taking credit for things being first, but one of the very earliest examples of content marketing, we basically mined the data in our database. Remember, we have the ability to observe every interaction between humans trying to get a date. Imagine having a video camera in every bar in the country and a team of grad students who were just diligently writing, “Oh 6’2″ white guy approaches 5’10” Hispanic girl and uses pickup line X. She rolls eyes.” Okay. That’s a data point.

You can watch every interaction literally to the point where we know that if you start a conversation with howdy, you do 30% better than if you say hi. Literally, we can go to that level of granularity because we have all the data. We start mining our data for these kinds of insights. After a couple false starts on execution, we end up coming up with this idea of writing a blog post once a month, where we would pick up a certain topic, almost always humorous, usually controversial, but always providing some insight into humanity.

Because it’s in this dating context, everyone has voyeurism and curiosity about dating because we all date at some point in our lives and we all are figuring it out as we go and we all want to know how are other people doing? We would write blog posts on the photos that work best on an online dating site, the pickup lines that work best in online dating sites. We were able to quantify how different races and ethnicities perform in online dating sites. We basically became required reading in the industry.

Aaron Dinin:

Wow. Never underestimate the power of content marketing is the moral, I guess?

Sam Yagan:

My favorite stat is in July of 2010, we had three consecutive Sunday section covers in the New York Times, different sections, business, art and culture, I think, or maybe business, tech and culture and OkCupid became the reference brand in the online dating category. If you were a writer or you were a journalist, or you wanted to say something about dating in America, you had to have the OkCupid perspective on it.

We basically took a business that was relatively flat-lining and it just began to really grow. We became a household name by the end of 2010. Just in the year that we thought we would all be giving up and leaving the company, we ended up getting bids from not just eharmony and Match, but also from the company that owned Jdate and Christian Mingle, which is called Spark Networks. Ironically also called Spark. By January of 2011, we ended up selling the company to Match.

Aaron Dinin:

OkCupid is still part of the Match network. In fact, Sam even went on to spend a few years as CEO of Match, where he also oversaw the explosive growth of Tinder. Yeah. Sam Yagan has definitely had an enormous impact on the online dating industry, both through OkCupid and beyond. It’s an impact he’s quite proud of.

Sam Yagan:

I think we brought joy and happiness to millions of people. I think that with all due respect to Google, the search for companionship is the most important search of your life. When I wear my OkCupid hoodie out in the world, I inevitably will get stopped by someone who will tell me their story. I’ve heard every story and people have cried to me on airplanes. I’ve gotten hugged and carried in Vegas casinos. I mean, we change people’s lives and that is the thing that I’m proudest of.

Aaron Dinin:

Helping people find joy, happiness, and love. It’s hard not to be proud of that. You know what? Speaking of helping people find things like joy, happiness, and love, I hope you loved this episode of Web Masters. Not the same kind of love I’ll admit, but it’s something, right? If you enjoyed it, why not share it with someone you care about so you can give them the same happiness? I’d like to thank Sam Yagan for sharing his story and the story of OkCupid. If you’d like to see what he’s up to these days, you can find him on Twitter. He’s @samyagan.

This podcast is on Twitter. We are @WebMastersPod and I’m on Twitter @AaronDinin. That’s A-A-R-O-N-D-I-N-I-N. I also write lots of articles about startups and entrepreneurship. You can find most of them over on medium.com just by searching my name. Quick thanks to Ryan Higgs, our audio engineer for his help with this episode, and a thanks to our sponsor, Latona’s, for all their support. Don’t forget, if you’re in the market to buy or sell an internet business, make your way to latonas.com.

Don’t forget to subscribe to Web Masters so you get our next episode as soon as it’s released. That’s coming soon, but for now, well, it’s a time for me to sign off.

[OUTRO]

Aaron Dinin:

You mentioned regretting the name OkCupid, what was so bad about it?

Sam Yagan:

We wanted to be the opposite of eHarmony, which was pitching you a soulmate and the idea that we were just, OkCupid, we weren’t Perfect Match or Perfect Cupid or whatever. We liked the Ok. We also liked the idea that it could be like, Ok,Cupid. Like, “Okay. Cupid.” Like it’s very conversational. We liked a lot of dynamics of it. I think it’s not good for international. It’s probably too many syllables, so there are lots of nuances about the name that in retrospect I don’t love, but people ended up calling it OKC so it’s not so bad.

Aaron Dinin:

I like that. I thought it was like Ok, as in, are you ready for Cupid? I didn’t realize it was Ok, as in mediocre. It’s like, rather than helping people find their soulmate, you were trying to help people find someone they could tolerate. It’s quite the value proposition. I’m surprised you got as big as you did.