Sam Yagan: “Don’t Start a Company Lightly”

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A perpetual willingness to rethink your ideas and re-evaluate your world view is an important value in business, believes Match.com CEO Sam Yagan, MBA ‘05.

Sam Yagan is the CEO of Match.com and a co-founder of OKCupid, which Match acquired in 2011. Now part of IAC, the company operates 40 dating sites around the world, reaching 15 million active users and 3 million subscribers per month. Yagan estimates that at least 10% of all marriages in the U.S. start with one of Match.com’s websites. In our interview he talks about immigration as the original entrepreneurship, the dark days of being a leader at a struggling startup, and the satisfaction that comes from providing the spark that starts families. He graduated from Stanford GSB in 2005.

In 10 words or fewer, what is the big idea behind your business?

We make the most important search of your life better.

What is the best advice you’ve ever received?

My mom always said, “Never give up.” A thread of that is “be willing to fail.” They are opposite sides of the same coin. If you include both sides, you have the seeds of entrepreneurship. My parents are immigrants, the ultimate entrepreneurship. That philosophy of never giving up is part of how you convince yourself to leave a country and travel to a place you have never been, where you don’t speak the language and you don’t have any money.

What was the most difficult lesson you have learned on the job?

In the early days of SparkNotes (a company Yagan co-founded that provided online study guides), I knew everyone and had personal relationships with each of them. As the company got bigger, I neglected to formalize communication channels and I lost that connection. One day a co-worker said, “I heard we were going out of business.” Yet we were doing our best ever! I was failing at my job as a communicator and at rallying the troops. So I started to have coffee with different people every week. I instituted the same program at OKCupid and Match. We now have 1,000 people at Match, so I have a small group lunch every month. There is no substitute for one-on-one interaction between the leader of a business and the people.

What advice would you give other entrepreneurs on how to build a great business?

Don’t start a company lightly. If you are unhappy in a job, you can just quit — start fresh and do something else. But when you are an entrepreneur, you follow the law of the sea: A captain can’t bail from the ship while passengers are onboard. You recruited every dollar and every person in your company by looking someone in the eye and saying, “Believe in me. Follow me.” You can’t just walk away.

What inspires you?

I think my company makes a meaningful difference to the lives of our users. I would never want to do anything where I didn’t think my job mattered. There are a lot of ways to matter. You could work in a soup kitchen or be a teacher or a police officer. I still remember the first time we got an email from a user who sent us a picture of his baby. I thought, “Holy cow, this is a human life that would not have existed if it weren’t for OKCupid!”

What is your greatest achievement?

Making my parents proud. My parents came here from Syria to give their kids opportunities they never would have had. I think I’ve made their sacrifices worthwhile. My kids have opportunities I didn’t have, and I expect even more from them.

What do you consider your biggest failure?

Failure is an interesting word. Failure implies something more existential. I would say a failure is something you tried to do and didn’t succeed. A mistake is a bad decision you made.

My biggest professional mistake was not buying back SparkNotes when the company that bought it went out of business. If I’d had a clear vision of the Internet and where it was going, I would have bought back the company and it would have been a huge win.

My biggest failure was in running eDonkey (a peer-to-peer file sharing network). I tried to get the music industry to rethink the way they did business. The press characterized the issue as “free versus paid,” but the truth was, record labels wanted to sell albums — groups of 18 songs for $18 — and consumers wanted to buy individual songs. Steve Jobs did what I was unable to do. He said, “It’s 99 cents a song now, and that’s how it’s going to be.” I tried to do that and failed.

What values are important to you in business?

Openness to new ideas; yours or someone else’s. A perpetual willingness to rethink your ideas and re-evaluate your world view. A commitment to developing colleagues’ talents. The people who are most successful are those who are committed to bringing out the best in other people.

What impact would you like to have on the world?

I want to have made people’s individual lives better. SparkNotes, OKCupid and Match really make an impact. They help people get through school and learn or find love and companionship. The search for companionship is why we exist in the world: to find someone, have kids and develop your kids. I like to think that, as a result of my work, millions of people have found love and companionship they wouldn’t have found otherwise.

Why are you an entrepreneur?

I thrive in ambiguity and unstructured environments. Some people shy away from those places. The nooks and crannies of ambiguity and uncertainty are appealing to me. I find it exciting to have the opportunity to think and learn and make mistakes. I like working on things that are tied to my identity. And I love the thrill of the chase.

What was your first paying job?

I was a teaching assistant at Harvard in the computer science department. I appreciated and understood how hard it is to be a teacher, and that teaching is a real skill. Being a leader, so much is about communicating and explaining an idea, being able to clearly articulate what you think in different ways to different audiences. That’s what teaching is.

Do you believe in balance? How do you achieve balance in your life?

Is balance “everything in moderation?” No. I am all about extremes. I would rather have lumpy balance than smooth balance. I would rather have a couple of things I feel passionate about than 10 OK things on the professional side and 10 OK things on the personal side.

What is the best business book you have read?

Influence by Robert Cialdini. It’s a survey of psychological tests and conclusions about how people make decisions, and how you can use that to influence thinking.

What businessperson(s) do you most admire?

Elon Musk and Jeff Bezos. They are just so compelling in their limitless ambition: to go to the moon or have drones deliver your things. Everyone must have told them, “You can never have that.” They just said, “I believe, and I’m going to go do it.”

What is the most valuable thing you took away from your time at Stanford?

The incredible quality of the relationships.

What do you think is the greatest innovation in the past decade?

Driverless cars will be transformative and will dictate the way we work, commute and plan cities.