Roll With Rondo

On its face, it sounds ridiculous to go to that much trouble to fulfill such a frivolous request. But that’s the nature of the business. “What [athletes] don’t realize is the sheer exhaustion that they can cause people because the demands are so high,” Gross says. “It’s 24/7.”

Rondo’s business basically works like this: When a client contacts him, he first consults his database, where he lists his customers’ various preferences. What types of cars they like, if they have a preferred driver, where their favorite pickup spot is, who their relevant family members are, when it’s anybody’s birthday, and what types of snacks they like in the limo. To keep one client happy, SGT ships a hard-to-find brand of chips to car services all across the country, ensuring that he has them no matter what city he’s in. (“If the bag’s close to being expired, we’re not going to put it in the vehicle,” says one of Rondo’s employees.)

The next step is to subcontract the ride. Because he doesn’t have any vehicles of his own, Rondo has pre-negotiated rates with limo companies in pretty much every big city in the country. (No overhead is, of course, a good thing for a fledgling business, though without his own vehicles, Rondo’s profit margins are smaller. It’s essentially a less-risk, less-reward strategy.)

For some of those limo companies, Rondo’s clients account for enough of their business to give him considerable sway. Before striking out on his own, Rondo earned his stripes by working for Jerald Robbins, the president of Weldon Worldwide Services, a local limo company. When they parted ways, they made a deal: Rondo would get Robbins’s contacts in exchange for subcontracting rides to him. Now, Robbins says, Rondo’s clients make up about 10 percent of Weldon’s business. As a result, Robbins makes sure to always hold cars in reserve on game nights in case they’re needed at the Garden. To accommodate all the athletes (and their very large bodies) that Rondo has brought to him, Robbins added three new SUV limos to his now 28-car fleet. Rondo also gives him pointers on how to stay attuned to the creature comforts players prefer. “High bass, lots of speakers, a lot of high-end stuff,” Robbins says. He adds that he just bought a 14-passenger mini coach that the players frequently use. Robbins, the type of guy you’d more expect to find kibitzing in a deli than thumping bass in a car, is especially proud of the new ride’s “really kick-ass stereo system.”

Most of Rondo’s business right now happens in Boston, New York, Miami, Chicago, and Los Angeles, where many of his entertainment clients are located. Out in L.A., Alex Ghorbani, the CEO of LAX VIP Limousine Service, says Rondo accounts for about 10 percent of his business, or about $8,000 to $10,000 per month on 40 to 55 trips. Ghorbani recently bought another Escalade limo to help accommodate the customers Rondo directs to him. (In case you were wondering, Ghorbani offers this breakdown of limo-service divas: “Athletes are not that bad. The movie industry is worse. The people in the music industry are not that bad because they are always high or drunk…. It makes it easier, but it makes the car so filthy.”)

Rondo says he arranges 12 to 25 rides per day, and has had few instances where a client has gotten out of control in the car. If necessary, he says, he’d cut ties with a big troublemaker. After all, the whole enterprise rests on people trusting him — from the limo operators, club managers, and restaurant owners to the professional basketball players, rappers, and high-powered professors. At the end of the day, what differentiates Will Rondo’s business is Will Rondo. That means everything reflects on him.

“Back door! Back door! Back door all day!” Rondo yells from our seats after Celtics guard Avery Bradley makes a nice cut to the hoop for an easy bucket. The C’s are handling the lowly Wizards pretty easily, and Rondo is especially pumped about the play of Bradley, both a friend and a client. By halftime, Bradley has already piled up 19 points against the Wizards, and Rondo is in such a good mood that he doesn’t even notice that his brother, despite eight assists, has gone scoreless. With the game on break, Rondo embarks on another handshaking tour of the Garden. During 15 minutes of walking around and glad-handing, seemingly the only person he doesn’t talk to is Aztec Gino, a Celtics super fan who dresses up in mock Indian garb and has the unique distinction of being disliked by pretty much everyone (when he’s nearby, Rondo eyes him suspiciously).

As halftime winds down, Rondo calls up his friend Christa Jones and arranges a confab in the Garden concourse. Jones is the vice president of Institutional Advancement at the Urban College of Boston, and also runs Mogul Executive Services, a concierge service (she says her business doesn’t tend to conflict with Rondo’s since he’s more focused on transportation). She helped him get his company set up, and now may be able to help him expand it.

Rondo says he’s intentionally kept things small so far, so he can provide personal attention to all of his clients. But he’s slowly growing: He says he now does VIP transportation for groups, including the American Heart Association, the Thurgood Marshall College Fund, and the NBA Players Association, and he recently launched a smartphone app for his clients to book through. The app made a big enough splash in the industry that it helped earn him a feature in the trade publication Limousine, Charter & Tour. Rondo says he’d love to eventually put employees on the ground in other cities.

Jones, it turns out, is having a meeting soon with some of the people behind Shark Tank, the ABC reality show where entrepreneurs pitch a panel of venture capitalists (including Dallas Mavericks owner Mark Cuban) to try to get them to invest. She says she’ll bring up Rondo’s name to try to get him on the show. Rondo likes the idea, but says he also plans on meeting with banks to try to find more-traditional investors.

Of course, there is the same old dilemma: If he does end up getting on the show, it would no doubt be, at least in part, because he’s Rajon Rondo’s brother. Then again, none of the sharks are going to give him any money just because of his bloodline — they’d have to like his business.

As he and Jones hash things out, I think back to that time Rondo and I were chatting at the diner in Waltham: As we were getting up to leave, he passed me the pamphlet he’d just produced for SGT. I pointed out how it didn’t say the name “Rondo” on it anywhere. He nodded — that was intentional — but then waffled for a moment. “Do you think I’d benefit more if I used the name and said who I was related to?” In the end, though, he didn’t waver: If you go on the SGT website, you won’t find his last name anywhere.

Ever the prideful big brother, what he likes best, he says, is when he’s being recommended by a satisfied customer and Rajon doesn’t come up. “Sometimes they leave off my last name,” he says, “and just say, ‘Call this guy, Will. He’ll take care of you.’”