Fail Because You Are Trying: An Interview with Sam Yagan

Sam Yagan

The latter part of the title is the beginning of a quote from my conversation with Sam Yagan, CEO of  The whole quote is: “Fail because you are trying, not because you are not trying.” It is probably a good example of why Time Magazine in 2013 named him one of “the 100 most influential people in the world, from artists and leaders to pioneers, titans and icons.” People hesitant to act for fear of failing accomplish little. All of my bold leader interviews to date have reinforced this fact.

Bold leadership, at its core, is about action. Ideally it is about constructive action, which means it comes with some other requirements that Sam described as we spoke.

Sam is no “one note wonder.” He is a successful entrepreneur with a few companies created, grown and sold under his watch. This includes which he sold to The Match Group, a division of IAC, in 2012. There is plenty of information about his entrepreneurship available through many online interviews and stories. As we began, I told him my interest was less about his entrepreneurialism (although very interesting) and more about how he thinks about leadership. His bold leadership.

Making tough decisions is bold leadership.

The notion of bold leaders willing to make the tough decisions came up early in our conversation. His perspective makes it clear why people follow Sam. Who among us doesn’t crave a leader who has the qualities Sam mentions here: “There is a boldness in leadership whenever you are honest, transparent, long term focused and looking out for the organization – not yourself.” 

I asked if bold leadership is always noticeable. He reflected on both the leadership required in the “corporate suit” (his words!) role he finds himself in today leading a large organization and that of a startup guy with a small, close-knit team.

“Noticeable? Well, no. Not always. Actions and decisions become bold because no one has done them before – made the really tough calls.” Sam summarized, “A lot of leadership is having the tough conversations.” Stepping into the CEO role at Match, he said, “We’ve had some really tough things that we needed to do. At points the rank and file were shocked the former leaders hadn’t done them.”

Having a huge bias for action is bold leadership.

Like other bold leaders I’ve interviewed, Sam has that strong, forward movement orientation. He said his entire leadership training has been “on the job.” Given that, he says there are no alternatives to erring toward action. “There is not another option to, ‘Okay, let’s just start doing.’ I’d rather make a decision with 80% versus 99% of the information.” Sam is talking about learning your way to the right answers. “Fail because you are trying. Not because you are not trying.”

Sam mentioned a huge project at Match. “I want us to feel like we are riding a roller coaster. You see the dips and turns and at moments feel, ‘Oh, my god we’re going to fall off!’ And then we realize: ‘Oh, no we’re not.’” Embracing the ride – the uncertainty – is the mark of a bold leader.

Moving forward is bold leadership.

Like others I’ve met, Sam’s strategy is to think forward and don’t look back. He said, “I make bad decisions every day. You can’t spend all your time rethinking decisions. I tend to not reopen things that are already closed. Personally, I am very action oriented and move forward.”

Applying the right leadership style for the challenge your organization faces is bold leadership.

Sam describes offensive leadership as “the wind at your back. You are taking it to the market,” versus defensive leadership as “you’re getting punched in the face.” You may be the market leader, but you find yourself reacting.

Opposition, or competition, forces action and can light a fire in organizations not used to moving. As a bold leader in a larger organization, complacency is one of the hardest things to fight. You must use this “punch in the face” to galvanize your teams to action. As Sam described it, you “have to instill confidence and a willingness to act,” even when you don’t have all the answers. Especially because you don’t have all the answers.

When you are on offense, in organizations shaking up the marketplace and changing the rules, people find their way to you. The bold leader responsibility in that case is to channel that energy to the right results.

Finding your way is bold leadership.

If you are the bold leader, you can’t quit. You have to see the work through to the right outcome. And, because you aren’t clairvoyant, not everything works. Finding your way through becomes more personal. “You got us into this mess!” To Sam, finding your way means “You have to hold people more accountable. Question assumptions. Dig deeper yourself.”

“As an entrepreneur it can be incredibly lonely. Very often it is an open environment. Everyone is sensing your mood. It could be nothing to do with work, but people are watching you. There is a feeling of being under scrutiny all the time.”

In a big company it is a different kind of loneliness. “People want to be led so badly. I didn’t fully appreciate this, and there is a loneliness when you have that CEO title. Other executives can always go to their peers, their boss. As CEO they expect YOU to lead.”

And then this interesting thought: “People are followers in different ways. That can make it lonely. Whatever you are doing is inadequate, even if you’re doing well. Expectations are that you’re going to come down from the mountain… with the answers.”

Actively sharing your vision is bold leadership.

Most leadership books talk about the “great” leaders, first having a vision and second, drawing people to that vision. Sam observed that in his nine years at OkCupid, he never once got the “what is your vision” question. In entrepreneurial situations people seek you out because they get the vision and want to be part of it. “You signed up. You led yourself to me.”

Now in a big company, he sees that people have a different expectation and need, “Convince me why I should work for you.” They show up to work but really need to understand. The first time the “what is your vision?” question came up at Match, Sam says he chuckled. Then he realized, “No, they REALLY need to hear from me. Even if they KNOW the vision, they need to hear from me.”

Knowing yourself is bold leadership.

Often, when I bring up the notion of “bold,” people think extroverts, big personalities or “people” people. Sam is a great testimony to the fact that real (action-oriented) bold leaders can also be introverts. “I’m an introvert. I think to talk.” (Opposed to extroverts who talk to think.) “I am more likely to go in a cave and sort it out. When I’m faced with a business challenge, I have lots of 1-1 conversations with people I trust and respect as I think my way through a problem. The other thing is, I like to write. Once I brain dump out all the things I’m thinking, I can do the ‘therefore.’”

In closing I asked Sam why he does it. I loved his answer: “I don’t think of it (leadership) as a choice. I tell people I am prepared to lose my job. I do my job differently because of that. My team notices that I am willing to take risks. Some don’t pan out but they have input into my decisions, my motives; benefiting others before myself.”

So let me ask you: What is your motive for leading boldly? And, if you’re not, what are you afraid of that you need to let go?

As the first Aveusian to work in the U.S., Asia and Europe, Chris has a unique perspective on how leaders drive material and positive outcomes in today’s global marketplace.