The CEO’s Triple Crown

At this time of year, I often get asked: who do I think is CEO of the year? Or who is the most creative founder? Or whom would I call the entrepreneur of the year?

Typically, I’ll spend a lot of time explaining that each role is different, every year presents different challenges and opportunities, and that offering my opinion on who is the best in each of these categories is not really that helpful.

But clearly some people, teams, and companies defy the odds, competition, and haters to change the way we think about an industry, and ultimately how we as consumers actually behave.

There are the obvious choices. The new breed of disruptive companies that are still led by founders who inspire their teams, create amazing products, and change our behavior as consumers; Facebook, airbnb, Spotify, Alibaba, and Tesla all come to mind as big winners in 2014.

Then there are non-founders, people who had the courage or craziness to take on huge structural challenges, not of their own making, and through sheer force of will and execution are once again redefining their industries and creating huge new opportunities. Companies like Adobe, eBay, HP, and LinkedIn, under the leadership of highly skilled and seasoned CEOs, are reinventing themselves into more competitive growth businesses.

And of course, hot new start-ups led by visionary women and men are challenging conventions, changing consumer behavior, and raising money at very robust valuations! Today's darlings include Rent the Runway, slack, and Oscar to name just a few.

All of these CEOs are very different. Some have technology backgrounds; others have business training, while many see the world through the lens of their liberal arts education. They are both men and women, some who were born in this country and others who immigrated here.

What they share in common are things like character, courage, and an ability to harness a fear of failure into an unnatural will to succeed. They are positive people; leaders who take risks and are consumed with making a sustainable and positive impact on their companies, industries, and our lives. They are able to create a vision and harness their dedication, passion, and energy to bring others along and lead them to places most of us never imagined possible.

And yet none of them are my choice as this year’s Triple Crown recipient for founder, CEO and entrepreneur of the year (though each deserves special recognition all their own.)

No, the person I have in mind has worked for the last 10 years to found their own company, evolve their ability to compete and stay relevant in perhaps the most fickle and competitive of all industries. She navigated and is changing an industry where the business model has been under huge pressure for years and whose power brokers would rather hire lawyers then embrace change. At a very young age, she chose to go against the odds and the industry elders and bet on herself. She shocked people by giving up guaranteed money in exchange for ownership of her work. She said no to the insiders and power brokers and took a non-traditional path to success following her own vision and passion.

This CEO took a remarkable stand, and risked her brand and money for what she believes in. She had the courage to explain her thinking through a well-articulated Op Ed in the Wall Street Journal. This person has defied the odds and used new technology and social media to connect directly with her fans, embrace them, and make them a central part of her experience.

Innovation is hard. Remaining relevant with an increasingly fickle consumer is perhaps even harder. And yet, time after time this entrepreneur has managed to delightfully surprise and grow with her audiences, win new ones, and outsell all of the competition. When she launched a new product earlier this year, she sold more than 1.2 million units in the first week of release and in her industry that is the only new product this year to have sold more than a million copies in its first week of release. She is the only artist in her industry to have achieved that level of early product success not once, nor twice, but three times in the past decade.

In terms of social media following, this CEO ranks just behind the President of the United States in the number of people who follow her on Twitter. And, at not quite 25 years old (Happy Birthday DEC 13th!) this founder has already accumulated more industry accolades and awards than most people in her industry (or any other) will secure in a lifetime.

Wow, what a year for my nominee for best founder, CEO, and entrepreneur of the year, Taylor Swift!

I met Taylor when she was just 14 years old, and I was COO of Yahoo! She was playing her own music outside our cafeteria in exchange for us promoting her music. I had the joy of working with her more closely when I was CEO of Guitar Hero and, more recently, at my current company Chegg, where we helped launched her breakthrough album Red.

My family and I have watched and admired her ability to invent, reinvent, evolve, and stay relevant where almost none of today's music artists stick for very long. Taylor Swift has an amazing work ethic, vision, positive attitude, pure love and joy for what she does and whom she does it for.

And most amazing, and something she has in common with legendary Silicon Valley founders like Mark Zuckerberg, Jerry Yang, Reid Hoffman, Elon Musk, and Brian Chesky, is her clarity of purpose and willingness to do what she believes to be the right thing. When everyone tells her and other extraordinary founders that they can't do it, or shouldn't do it, or tells them they will fail if they do it… you know what they do?

They all say to themselves, the haters are gonna hate, hate, hate! But so what, I’m going to shake it off and I’m going to do it my way and I’m going to win big. And they do.

So Congratulations Taylor Swift. Not only do my daughters love, admire, respect, and root for you, but so do Linda and I. Can't wait to see you on tour!

Happy Holidays!