
March 12, 2025
Ted Leonsis – CEO – Monumental
What Leaders Can Learn From Sports, Media, and Washington DC Reboots, Ted Leonsis – CEO Monumental
In this Special Extended Edition of The Reboot Chronicles Ted Leonsis joins us with untold stories you will only hear here.
Ted is founder, chairman, and CEO of Monumental Sports & Entertainment, one of the largest integrated sports and entertainment companies that has the most diverse partnership groups in all of sports. The billion-dollar group includes eight teams, like the NHL’s Capitals, the NBA’s Wizards, and the WNBA’s Mystics; five venues including the Capital One Arena in Washington DC; and massive media, esports, and betting platforms—and other ventures changing the industry.
An early Internet pioneer, Ted was Vice Chairman and President of AOL, and cofounded Revolution Growth with Steve Case. A board member at Groupon and American Express, he also serves on the board of governors for the NBA, NHL, and WNBA—helping them reboot the next generation of sports, media, entertainment, and technology
Watch or listen as we unpack impactful and entertaining lessons you can use to reboot your business, why he bucked the trend and sold his AOL holdings, how he is upgrading Washington DC—and where he almost dropped the Stanley Cup.
Redefining Sports, Media, And Entertainment—On All Fronts
When Ted first got into sports, he noticed two major things that influenced how he wanted to grow. The first was that the other people around him who owned other teams, were “real estate people and they looked at teams as a product to fill their buildings”. He equates it to how the owner of a movie theater would work with studios so that they can bring in more business. He thought that was wrong, and clearly not enough…and became more focused on the fans—wherever they are.
The other thing he noticed was that everything was going to be digitized, and from his experience at AOL, he explains “This business really looks like a software as a service business.” Much like how SaaS companies are looking to hit a customer base renewal of 80% or more, sports teams are looking to do the same thing but hitting a renewal rate sometimes in the 90s. So those two key factors led Ted and Monumental Sports and Entertainment to become a better customer experience oriented platform with a broader impact.
Rebooting User Experiences
Sports has been going through massive changes over the last decade, with tsunami-sized waves of digital media, streaming, betting, esports and other tech. driven platforms. Now with the foundations of the innovations Ted and later Monumental wanted to make, we can move to the modern day to see what the strategy is now. This strategy primarily revolves around increasing user engagement.
Previously, a sports fan engagement with sports media was 3 – 4 hours long. They might show up to the game, be locked outside until the stadium opens up, and then be promptly asked to leave at 10 when the game is over. Ted wants to open those doors more, so if people want they could have more engagement with the things that they enjoy, all the while creating a more renewable ecosystem for sports media.
This includes opening up stadiums for business meetings or letting other corporations let their employees work out of the stadium, or bring customers, during the day, and then in the evening enjoy the game. Companies like Meta and others seem to like it. This will evolve into an entire sports book venue, that is open seven days a week all day long, so you can come in Saturday morning get some breakfast, watch a game, and place a bet on it.
On top, of that, they built an e-sports theater, where you can go and watch games live, or, wait for the ESPN coverage of it to come out and watch it at home. All of these changes and innovations are designed to promote user engagement, as well as potentially make owning a multi-billion dollar stadium more reasonable now that it is being optimized used regularly.
More Than Just A Sports Business
One of the realizations that Ted has had in the last couple of years is that what he is doing is more than just being the owner of a sports media company, he has become a staple in Washington DC from both an entertainment, economic, and cultural standpoint. This came to fruition as he was planning on moving his team to Virginia, as they were experiencing massive growth with new infrastructure being built, as opposed to where Monumental is in DC, where they are currently landlocked, and unable to build out in any direction. So, after an unpopular attempt to move his teams to the suburbs, Ted turned to the Mayor of DC and entered into a public-private partnership, and is now working on basically rebooting all of downtown Washington to create the “new front door for Downtown DC.”