How Michael Bloomberg Jump-Started Mo Vaughn’s Business Career

Mo Vaughn, one of the most feared sluggers of the 1990s, has quietly built a powerhouse second career in business, spanning real estate, trucking, sports ownership, and player development. 

The 58-year-old Red Sox legend and former American League MVP recently started a new podcast with Perfect Game, launching with A-list guests including David Ortiz, Nomar Garciaparra, Rafael Palmeiro, and former MLB commissioner Bud Selig. 

Following his retirement in 2003, Vaughn has quietly built a second career in business and investing that spans numerous fields, from affordable housing and player development to trucking and sports ownership.

Vaughn sat down with Front Office Sports to talk about all that and more, including how former New York City mayor Michael Bloomberg helped him start his post-playing career endeavor in real estate, and why he thinks Selig is underrated.

Front Office Sports: How did you start building your business career after retiring from baseball?

Mo Vaughn: I was lucky. Upon retiring, Mayor Bloomberg was running New York City—he’s a Boston guy, which I didn’t even know—and I had partnered up with my friend… His best friend was the chief of staff for Mayor Bloomberg. We connected the dots and I had a meeting with the mayor; the first question he asked me was “Do you really want to do business? Or do you just want to plant trees?” 

In 2003, we started Omni New York LLC. Mayor Bloomberg awarded me my first 289 units of affordable housing in the Bronx, and we revitalized those units. 

Eventually, we had 19,000 units across 11 states, with our own construction, maintenance, and security. That experience taught me everything: showing up on time, understanding politics, managing requisitions, navigating the city council. It was probably the most educational thing I’ve ever done.

FOS: In 2023, you sold Omni New York and launched another real estate company, SBV RE Investments LLC. You’ve also had your hand in a number of other businesses, including a Cleveland-based trucking company that you sold in 2018. How did the lessons you learned through Omni New York carry over into your other ventures?

Vaughn: Everything I learned with Omni New York LLC helped me in other ventures. With the trucking company, I’m not so sure that was a good business. Just the amount of expense, you need insurance on people, insurance on the vehicles, you know, different things like that. But you try some things, and lord knows, not everything works. But in turn, you learn a lot.

FOS: You also have Vaughn Sports Academy (a Boca Raton-based training facility where Vaughn helps aspiring baseball players develop), and you are invested in and have a role with Perfect Game. Tell me about those ventures, and how it has been getting involved in baseball again?

Vaughn: With Vaughn Sports Academy, I’ve applied the mentality I did to my other business ventures: we get up, we go to work, we represent ourselves, we follow through. It’s helped me shape coaching, development, and performance at [Vaughn Sports Academy], as well as my role at Perfect Game. That business foundation gives me confidence to make critical decisions and help others grow.

But man, I love being on the baseball side. Knowing the game the way I know it, in terms of what it takes to be successful in our game at that level—the type of person, the type of player, the mindset—these are things kids need to think about if they are serious about baseball. 

FOS: Did you think about business opportunities while you were still playing?

Vaughn: Back then, my mindset was very different. You think you’re indestructible. I didn’t fully see myself as the business. Now, I recognize my value and what I bring to the table. Today’s athletes are smart to secure ownership or equity early. It puts you in rooms and conversations you otherwise wouldn’t be in. I tell young baseball players now, ‘don’t try to do business. You are the business.’

FOS: Have you been involved in sports ownership?

Vaughn: Right now, I have a small interest through my partnership [with Eugene Schneur] in Leeds United, the soccer team that just made the Premier League. My college roommate Dana Brown is running the Astros [as general manager], so I get to consult a little there too. It’s fun being able to help there without the pressure of making all the decisions myself.

FOS: Okay, let’s get to the podcast. What made you decide to jump into that world?

Vaughn: I wasn’t really a fan [when I was first approached about the podcast]. During my career, every time I had a mic, I had to keep my mouth closed, don’t poke the bear, let sleeping dogs lie and all that. But once we started talking baseball, I realized your heart and soul are supposed to come out through the mic. 

Having the podcast has been the best thing I could have done. Not just for me, but for other guys to set the record straight. We all can’t be Derek Jeter, Cal Ripken Jr., Robin Yount. There’s always some pain, something hurt, something never said. Talking to guys like Rafael Palmeiro lets them say their piece without judgment. It’s almost therapy for me and the other players. 

FOS: Your first guests include Bud Selig and Rafael Palmeiro. They are iconic figures but due to scandals from that era, they aren’t viewed so positively nowadays. What is it like having conversations with those guys today?

Vaughn: Bud Selig, for instance, I hate that he gets bashed for PEDs. How many god damn great things did that guy do for our game? If you look it up, you will see. Realignment, retiring Jackie Robinson’s number, the wild card. All the things we like in the game, Bud Selig did those things, dammit.

When I talk to a guy like Palmeiro, I can see the pain. I can also see that he gets to say his piece, finally, with someone who’s not judging him. The podcast is almost therapy for me and for some of the guys.