Ross Levinsohn

CEO of The Arena Group

Ross Levinsohn has long been at the center of transformation and innovation in the media and technology spaces. Best known for his roles at Yahoo and Fox, Ross has served as CEO of a number of high-profile brands — driving change, culture, and results.

Prior to joining the Arena Group (formerly Maven), Ross served as CEO of Tribune Interactive, the digital arm of Tribune Publishing, publisher of more than 100 titles including the LA Times, Chicago Tribune, and New York Daily News, after having served as CEO for the Los Angeles Times.

At Yahoo, Ross served as interim CEO, overseeing all aspects of the internet pioneer with more than $5 billion of revenue and a $20 billion market cap. Prior to being named to that post, he was head of Global Media and executive vice president of the Americas region.

Ross also served as the president of News Corporation’s Fox Interactive Media, where he helped grow their digital business to the most engaging set of web properties in the United States.

Among his other roles, Ross has served as CEO of Guggenheim Digital Media, managing The Hollywood Reporter, Billboard Magazine, and Ad Week; a managing director of media and technology venture fund Fuse Capital; and an executive at HBO. He began his digital career at CBS Sportsline. He also served as a senior advisor at Boston Consulting Group (BCG).

Levinsohn holds a Bachelor of Arts in Communications from The American University, where he served as a member of its Board of Trustees.

Where did the idea for your career come from?

I am the CEO of a company started four years ago by a serial entrepreneur who has built multiple companies like the Arena Group – a single, technology platform company hosting multiple independent media brands. I was handed the reigns as CEO this fall.

What does your typical day look like and how do you make it productive?

I generally get up between 5 and 5:30 am and spend the first hour catching up on news, emails and messages, and then try to work out for 30-60 mins depending on my days schedule. With covid, most of my days are spent either on zooms or returning calls and emails. I try to take two 30-minute blocks (one in the morning and one in the afternoon) where I do not do anything but think strategically or I use those blocks for returning key calls or emails. Since I’m on the west coast, my days start to slow around 5 pm, so I then have time to catch up on missed emails and texts. I’m a single father, so when I have my kids (which is half the time) I try to cook them dinner so we get time together. After dinner, I go back online to work for another hour or two and end the day feeling like I haven’t left anything hanging.

How do you bring ideas to life?

I’ve always been a dreamer and have never been constrained by convention or the norm. I try to think outside the box and when I do, I always quickly jot things down on pads or note cards. I generally let them sit for a while and then come back to them and iterate a bit, always trying to poke holes in the idea. Once I’ve set it, I then bring other people in around the company to continue to challenge it or shut it down if it doesn’t take hold. Once I commit though, I try to ensure it gets the full support.

What’s one trend that excites you?

Reimagining brands from the past. I’ve always been into nostalgia and memorabilia. History was my favorite subject in school. I remember early in my career, a business acquaintance was starting Classic Sports Network, and I remember thinking how amazing it would be to relive great sports moments. It was a big success. The same is true for great brands of the past – converse, sports illustrated, etc.

What is one habit of yours that makes you more productive as an entrepreneur?

Listening. Too often people want to hear themselves talk. I’d rather listen, take the words in, and mold my ideas before I talk.

What advice would you give your younger self?

Have more patience.

Tell us something that’s true that almost nobody agrees with you on.

Traditional media has a very long shelf life. While people tend to always rush to the new, it is the turtle that sometimes wins the race with the hare. Age brings wisdom and experience. I remember George Foreman once telling me that he became a much better fighter in his 40’s than he was in his 20’s even though he was more fearsome as a younger man. His experience made him better. I’ve now seen decades of things come and go, and those with true staying power evolve, iterate, and adapt. Fads come and go. Value is built.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Be fearless. I’ve always said that I’m not so much an entrepreneur, but rather I’m entrepreneurial.

What is the best $100 you recently spent? What and why?

I was walking in Santa Monica and came across a homeless mother and her daughter. She was asking for money. Instead of simply putting $5 or $10 in her jar, I asked her and her daughter to walk with me to a nearby restaurant. I bought them lunch and then bought them a gift card for another few meals. I wanted to make sure they ate, and the money was used to help them both.

What is one piece of software or a web service that helps you be productive?

I spend the better part of my day connected to devices (computers, phones), so I used many different services including Slack, Google Docs, Microsoft applications, and software to make us more productive. I like efficiency, so any piece of technology that can save me a minute or ten is worth trying. But I have to admit, I still handwrite post-its and have what I call my “play-calling sheet” in front of me all day long. It looks like the laminated sheets the NFL coaches hold in front of them during games, and it contains all the things I need to do/remember each day.

What is the one book that you recommend our community should read and why?

I have two: “The Art of War“, which I think is a must-read for anyone in business, and “King of the World” by David Remnick, which is the story of the life, times, and struggles of Muhammad Ali. It’s a book about life, not boxing, personified through the eyes of Ali.

What is your favorite quote?

My father, first and foremost who always taught me to listen first, be thoughtful, and to treat people as you want to be treated. Rupert Murdoch taught me to never settle, never rest, and to always be curious. Peter Chernin taught me what being prepared looked like. And, Robert Hastings, whose ode to the journey of life called “The Station”, has been a guidepost for my own personal journey.

Key Learnings:

  • Listen
  • Be Patient
  • Don’t be afraid to try something new