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Fewer Trophies, More Mistakes: Flywheel Sports CEO Sarah Robb O'Hagan On The Entrepreneurial Spirit

This article is more than 6 years old.

In 2016, Sarah Robb O’Hagan resigned from a top job at Equinox to answer a question: Why were young employees becoming so afraid of failure? Her answer, Extreme You, is both a book and a movement about maximizing human potential and changing our culture. It calls for fewer ‘participation trophies’ and more growth through mistakes.

Today, Sarah brings Extreme You to Chicago Ideas Week where she’ll give a talk at the program Innovating from Within: When the Entrepreneurial Spirit Never Stops. I spoke with Sarah to learn how she applies Extreme You to launching, scaling and turning around companies. From Virgin Atlantic, Nike and Global President of Gatorade to her current role as CEO of Flywheel Sports, Sarah has grown through taking risks. In this Q&A, we go deep into her entrepreneurial approach:

Jayna: Sarah, your career has changed significantly since you left Equinox last year. Today, how would you answer the question, what do you do and how do you do it?

Sarah: I'm currently CEO of Flywheel Sports, an indoor cycling company that’s about to become an online cycling company. We’re nearing the launch of an at-home bike where you'll be able to stream our epic classes both live and on-demand.

As for how I do it, I'm in the business of helping people unleash their own potential. That’s what fitness is all about. I mean, why do we work out? It's generally because we want to strengthen our bodies and minds and get more out of our lives.

Jayna: Tell us about the difference between leading a brand and launching one. What has been unexpected or challenging about starting Extreme You?

Sarah: I feel lucky that I've worked for iconic brands like Nike, Gatorade and Virgin. When I set out on my own and started to work on Extreme You, it was amazingly difficult and different because there was no roadmap.

At established brands, like Flywheel, you spend the first few months indulging in the heritage story. It’s a source of inspiration. But when you're starting from scratch, the boundaries are so wide that you need something to pull you in.

That was hard for me. With Extreme You, I researched psychology and interviewed a lot of people. I used their stories to identify common themes and refine down to a core idea. It was quite a fun growth process, but it took a long time to land on the right idea.

Jayna: What was the big insight? When did you realize that you were onto something?

Sarah: I was interviewing extremely successful people from very different walks of life. When you talk to Condoleezza Rice, Bode Miller and Mister Cartoon, the famous tattoo artist, the three couldn’t be more different. Yet as they talked about their life journeys, their careers and the methods they use to get the most out of themselves, I noticed commonalities in language and thought process. That’s when I realized I was onto something.

There is a reason why certain people outperform others. It goes beyond natural talent or being born in the right home. It is all to do with how you understand your unique traits and exploit them to the max potential.

Jayna: What motivated you to launch Extreme You? How does it help people maximize their potential?

Sarah: It came down to a few things. First of all, I'm a parent of three children, and I was horrified to see my kids come home from youth soccer with ‘participation trophies.’ I connected the dots between that and what I saw amongst the new generation coming into the workforce.

I speak at a lot of colleges, and students always talk about their fear of failure and the pressure to be perfect and not make any mistakes. I suspected that these fears came from being given trophies throughout life just for showing up. These students hadn’t been pushed to fail, make mistakes and grow from them.

That cultural shift concerned me and led me on this exploratory journey. I wanted to see if, in fact, that the people who’ve achieved success are those that have made lots of mistakes, embraced them and grown with them.

Jayna: How is your approach to dealing with fear of failure different from other approaches out there?

Sarah: It comes down to worrying less about the outcome and more about this question: In everything you do, are you developing yourself?

Culturally, we tell people to make five-year career plans. If you have such a plan, you don’t want to make mistakes and fail because you want to reach the five-year goal as quickly as possible.

You see failure differently if every decision starts with the question, “Is this pushing me and developing me in a new way?”

You’ll take risks and have no idea if you’re going to succeed. If you do succeed, awesome – that’s going to move you faster to your next opportunity. And if you fail, that’s awesome too because it will teach you things that progress you forward.

The outcomes arrive if you develop yourself and get to know yourself better. But if you just focus on the end goal, you’ll be less likely to take risks.

Jayna: The Extreme You manifesto talks about this idea that you need to “get out of line” to achieve your potential. Can you share what that means and an example from your career?

Sarah: There are moments when you're amongst a peer group and you can either choose to jump up and grab an opportunity, or you can choose to wait in line. Getting out of line is taking that opportunity.

The research says there's a time and place to do it. When people who don’t yet have credibility get out of line, they look like they’re just trying to take credit for themselves. We've all met that person. On the other hand, if you have credibility, there's an open gap and no one’s going for it, now might be the time to step out of line.

My example of that was when I started at Virgin Atlantic in my late 20s. The person who hired me was let go from the company. I joined a team that was in total disarray. All of us were wondering, who's going to be the new boss? What’s going to happen?

I remember thinking that either I’m going to get fired – because I'm the last one that arrived and the person who hired me was fired – or I can get out of line. I put together a marketing plan and slid it under the president’s door. I already had six years of experience in a similar role and company, so I had credibility. I was coming from a grounded place and was solving a problem for the team, which didn’t have leadership. I jumped out of line at the right time and was able to execute my plan.

Jayna: You’ve been vocal about rejecting a culture where everyone’s a winner and gets a trophy. Today, in our business culture, a lot of people will say that everyone’s “entrepreneurial.” How do you define an entrepreneur, and can people in huge companies be one?

Sarah: Yes, I love that question because I think you're onto something. I do think that we’re overplaying the word “entrepreneurial.” What is an entrepreneur ultimately? It's not somebody that starts a company and gets a bunch of funding rounds. An entrepreneur is someone who solves problems that other people haven’t thought to solve.

When I started Extreme You, I can't tell you how many people called me to ask if I was looking for funding. They assumed I must be creating a tech startup. I said no, I'm trying to solve a cultural problem. That’s one way to be entrepreneurial.

I believe people can be entrepreneurial in giant companies, but I don’t think people generally are. Being entrepreneurial means jumping into worlds that hadn’t existed before. It means taking great risks with no certain outcome.

In big companies, I wish more people had the courage and freedom to do that. Often, that’s what holds back big companies that move into decline phases. They’re unable to break that cycle of playing it safe. Usually, would-be entrepreneurs are contending with too many layers of bureaucracy. At the same time, many people just don’t act on their ideas.

I've been in these big companies. At Gatorade, for example, people felt pressured to defend legacy capital investments. When I think back to that turnaround, the options were clear. Either I was going to get fired because we didn’t turn around, or I was going to get fired because we tried and failed. I’d rather do the second.

I've been lucky to have a career in industries that have gone into big downturns. You realize in those industries that if you cling on to the past, there's no way you'll ever get to the new future. That future requires entrepreneurial thinking, and it requires action.

Jayna: When you're scaling a company like Flywheel beyond startup mode, how do you preserve the entrepreneurial spirit?

Sarah: I'm having the time of my life in this role because I’ve never scaled something up before and we do have an entrepreneurial approach. In the back of my mind, I’m thinking about how not to become one of those big, bureaucratic companies.

I’m constantly asking people to bring their own ideas to the table and act on them As I mentioned, we’re launching a tech platform, and no one’s ever done exactly what we’re attempting to do. We’re integrating a streaming platform into a studio business.

Every day, there are moments where someone says, “Whoa, we didn’t think of that…How do we do we even do that?” The spirit of entrepreneurship is to push through those challenges and get it done.

Jayna: Can you tell us about a moment when you weren’t living up to your potential? How did you know and what did you do in response?

Sarah: That happened when I was in my last role at Equinox and ended up leaving. There wasn’t any room for me to grow. As much as I loved the company and felt passionate about the business and the people, I felt restless and wanted to be thrown into an experience that would challenge me more.

Equinox is a successful company on a strong trajectory, so it was difficult to leave. But I'm so glad I did because it threw me into this experience that feels like ‘entry burn’ – when a space shuttle comes roaring into the atmosphere, and the astronaut’s whole body is shaking.

The first month on my own was disconcerting but energizing. I was used to back-to-back meetings every day and people all around me. I’m super extroverted. Suddenly, I find myself sitting at a laptop, and it's just me.

I’d go to meetings in the city and people would ask, where’s your office? Starbucks, I’d say. It was clear to me that when you throw yourself into those uncomfortable situations, they wake you up. It's like when you take on a new kind of workout at the gym, and you have intense muscle soreness the next day.

Jayna: What are you currently struggling with as a leader and founder? Can you walk us through your approach to solving the problem?

Sarah: I don’t know if I’d ever use the term “struggling” because I find that the most challenging problems are often the most energizing.

Right now, my team is on the eve of launching that streaming platform. Again, I don’t think it's a struggle, but there are so many unknowns about how the platform is going to perform, how it will change the culture and how it will affect our core business. We know that some things are going to go wrong. Rather than be fearful or worry about those things, I let them become great challenges and problems to solve.

To learn more about Sarah Robb O’Hagan, visit www.extremeyou.com

Chicago Ideas Week 2017 runs October 16-22. Check out the events and speakers at www.chicagoideas.com