The first time Mark Shapiro saw Westport, he was scouting for an editing facility that his then-employer, ESPN, could use for an upcoming project. As they drove through town, he and his wife, Kim, had the same thought: can you imagine if one day we could live here?
Nearly 30 years later, not only does Mark reside here in town, but he recently had the honor of being named StartUp Westport’s Innovator of the Year. “Westport is a place that has really become home with a capital H,” Mark said at the award ceremony, held at The Westport Library on October 8. “It’s a town where, like everything else in life, you get back what you give.” And Mark has given a lot. In his impressive career, he’s worked at ESPN as the executive vice president for programming and production (creating, among other things, Pardon the Interruption, as well as acquiring rights to properties like Monday Night Football and the NBA); Six Flags as the director, president, and chief executive officer; Dick Clark Productions as the CEO and executive producer; and is now president and managing partner at representation company WME Group as well as the president and chief operating officer of TKO Group, the parent of WWE and UFC. “I’ve been fortunate to win two Peabody Awards and 16 Emmy Awards. Being recognized for the innovation that it takes to develop that type of award-winning programming means a great deal to me,” Mark tells Westport Lifestyle. “Innovation is about seeing what’s possible before others do, and having the conviction and courage to go after it. It’s equal parts imagination and execution.” This outlook is both a beautiful summary of his visionary mindset and demonstrates why he was chosen by StartUp Westport as their honoree.
At the awards ceremony, Mark spoke in a fireside chat with CNBC anchor Sara Eisen, sharing hard-won wisdom from his career with the crowd. “You have to go with your gut and you have to have convictions, but you need to listen, you need to be curious, and you need to not preach and act like you know everything, because you don’t,” he said. He also spoke about the importance of a strong, loyal team, noting that when he left ESPN for Six Flags, he took 16 people with him, some of whom he still works with today at WME and TKO. “A leadership recipe that I've taken with me throughout my career is surrounding myself with the right people. Because how much can just one person do? It doesn't matter how granular I get with the business, there's so much to do. And you can't accomplish it if you don't have experts, people that will work hard, people that are passionate, people that have vision, people that will put themselves out there, people that will give it to you straight, and if you fail, get right back up and do it again.”
Mark spoke at length about failure being constant, but temporary: “you learn from your mistakes, but you don’t dwell on them,” he said. That attitude allows Mark to be the forward thinker that he is, investing in what he believes in— from paying $4.2 billion for the UFC (and most recently selling the media rights for $7.7 billion to Paramount) to investing in new Westport restaurant Massi Co., headed by the passionate Massimo Tullio. “I never think in terms of avoiding risk – I think in terms of managing it,” he tells Westport Lifestyle. “The calculus: is the potential upside transformative, and do I have the right people around me to deliver on the promise?” Another hallmark of his leadership style, he explains, is not shying away from feedback, even if it isn’t positive. “The last step is always a brutally honest post-mortem on the outcome and results.”
Truly, the through-line for all of it is people. Mark builds relationships, whether on a global or local scale. He reminded the audience to nurture their connections, not when they need something but out of authenticity. People, he says, are the great joy of his career. “I’ve worked alongside some of the brightest minds and most talented individuals across a handful of industries. They've taught me a great deal, tested me constantly, and ultimately upped my game. That has all enabled me to do the same for those I lead,” he says.
Even with all his worldwide success, Mark remains a devoted champion of our community. “Westport is a constant reminder that impact isn’t just global,” he says. “It can, and often does, start local. The community here has done nothing but support me and my family, and it’s always been a foundational element of who I am to return that spirit and energy.” (Though the Chicago-area native does have one piece of advice for Westporters: wave to your neighbors! “When I drive down my street and I see someone walking their dog, pushing their stroller, or on their bicycle, and I wave to them, they don't wave back!” he said with a laugh. “Spread the word: say hi!”)
StartUp Westport focuses heavily on mentorship, and they couldn’t have chosen a 2025 honoree who better reflects that value. “I’ve been blessed over the years with a collection of mentors teaching, challenging, and showing me the way; I try to do the same for individuals here in Westport,” he says. “There’s no doubt we have an extraordinary group of future game-changing leaders in this town.”
“Westport is a constant reminder that impact isn’t just global,” Mark says. “It can, and often does, start local."