Tracy McGrady's Real Business Education

Tracy McGrady opens his Bloomberg interview with a line that most business profiles would bury in paragraph seven, if they'd run it at all: "18 years old, I'm a millionaire. I've never learned anything about finances."

That's the whole story, honestly. Everything that comes after — the Buffalo Bills ownership stake, the OBL basketball league he built from scratch, the NBC analyst seat — is just what happens when someone who started from zero decides to keep learning instead of pretending they already know.

I've watched a lot of entrepreneurs do both. The ones who pretend don't usually last.

The conversation was the pitch

McGrady came into the Bills deal sideways. He'd wanted in on the Tampa Bay Buccaneers — hometown team, made sense. Didn't happen. The Atlanta Falcons ownership group was too far along by the time he got a call. Then Buffalo came up, and his connection to the market was more honest than strategic: he'd played three seasons for the Toronto Raptors from 1997 to 2000, and Bills legends Bruce Smith and Thurman Thomas used to come to his games across the border.

That's the kind of thing that sounds like a lucky coincidence until you realize the only people who get those lucky coincidences are the ones who spent years showing up.

He called his cousin — Vince Carter, who is a person you may have heard of — they went to a Bills game, and afterward they sat in owner Terry Pegula's office for an hour. McGrady described going in thinking he had to perform, had to sell, had to prove himself. Instead, they just talked.

"We just casually had a conversation, man, after the game, sitting in his office and just chopping it up for about an hour. And from that conversation, he was like, 'You want to be a part of this?'"

Anyone who has ever closed a deal — or watched one close, or watched one fall apart — knows exactly what happened in that room. Pegula wasn't evaluating a pitch. He was evaluating a person. And McGrady, who had spent years learning how to read rooms he'd never been in before, understood the assignment without being told what it was.

The check was large. McGrady didn't lose sleep over it. His explanation for why is more grounded than it sounds: he'd done the work to get there, and he was too excited about who he'd be sitting next to to worry about what he was signing away.

"There are not a lot of guys that look like me that are part of those groups," he said. And then, when asked whether being an owner changes how people see him: "I don't give a damn."

Both things can be true. The door matters. What you do once you're inside matters more.

The loud guy in the suite

Here's the detail from this interview that I keep turning over. McGrady described being in an owner's suite during a Bills game — one of several groups being evaluated for a minority stake. He sat quiet. Watched the game. Read the room.

Someone else in the suite did the opposite. McGrady wouldn't name him. Just said the guy was "loud and obnoxious and just going crazy."

That person didn't get in.

McGrady's read: "It don't matter how much money you have. Like, you got to be solid."

This is not a complicated lesson, but it's one that apparently needed demonstrating to a grown adult with enough money to buy into an NFL franchise. The room wasn't looking for the most enthusiastic bidder. It was looking for someone who understood what kind of room it was.

I think about the small business version of this story constantly. It's the vendor who emails twelve times before you've had a chance to respond. The partner prospect who talks about themselves for forty-five minutes at a first meeting. The investor who shows up with a term sheet before you've finished your second coffee. The money is real. The understanding of the situation is not.

McGrady watched that happen, filed it, and when he got the call that he was in, he knew exactly what he'd been graded on.

What stubbornness looks like dressed up as strategy

The OBL story is the one this interview should be remembered for, and it's the one most likely to get cleaned up into something inspirational and useless.

Here's what actually happened: McGrady had an idea for a basketball league — think high-level one-on-one competition, a platform for players who still have game but no NBA roster spot. He tested it. He took it to six cities, ran a season, found real players, found real audiences. Got enough feedback to believe he had something.

Then he went looking for money and struck out. Completely.

"Everybody's not going to believe in your vision. Right. Everybody is not going to be able to see your vision and what you're trying to create."

He could have killed it there. A lot of people would have. Instead, he went home — literally home, to the gym he has at his house — brought players in, kept filming, kept posting, kept the thing alive on his own.

That's not a strategic pivot. That's stubbornness. That's someone who believed in the thing enough to fund it with their own time when nobody else would fund it with their money. I have covered enough small businesses to know that the ones who survive the fundraise-didn't-work moment are the ones who couldn't figure out how to stop.

The right partner found him. NextGen Sports, a group with experience running alternative sports leagues, saw what McGrady was building and came in. According to McGrady, NextGen has been involved with the AVP volleyball league and a Big3 team — claims I'd want confirmed before treating them as settled fact — but the shape of what he's describing is a group that knows how non-traditional leagues actually work, which is a very different thing from a group that knows how to write a check.

Now McGrady is building OBL into a city-based league structure, handing 15% stakes to local figures — Jadakis running the New York team out of Yonkers, John Wall with the Raleigh team, Tim Hardaway Sr. in Miami — and using their existing audiences as the marketing infrastructure. He's already fielding interest from China and Australia.

The content kept the league alive long enough to find the partner. That's the actual sequence. And anyone who has kept a business on life support with their own labor while waiting for the right person to walk through the door will recognize the texture of it, even if the scale is different.

The 25-year return on a relationship

McGrady's connection to China started in 1998 or 1999 — his first trip there, back when organized basketball was still sparse on the ground. He was reportedly part of the group that participated in the NBA's China Games in 2004, playing alongside Yao Ming with the Houston Rockets when that market was just starting to take shape. He says he's still capitalizing on those relationships today.

I want to be careful not to make this into a lesson that sounds like "go to China in 1998." The actual lesson is narrower and more transferable: the relationships you build before a market is obvious are the ones worth the most when it becomes obvious. McGrady was in those rooms because he was curious, not because he had a market thesis.

Most of us are not going to the NBA China Games. But most of us know someone we've been meaning to have coffee with for two years, or an industry adjacent to ours that we've been vaguely interested in but never pursued. The gap between McGrady's version of this and yours is mostly one of scale.

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McGrady is now an analyst on the NBA on NBC — the league's new broadcasting home as of the 2025-26 season, which marks NBC's return to NBA coverage after more than two decades away. He grew up watching the league on that network in the '90s, which is also the era that made Michael Jordan a global brand and turned basketball into something people played in China. The full circle of it is almost too neat, except that McGrady earned every rotation of it.

"Eighteen years old, I'm a millionaire. I've never learned anything about finances."

What he didn't say, but what the rest of the interview makes clear, is that he decided that sentence was a starting point. Most people treat it as an excuse.

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Dorothy "Dot" Williams covers small business and entrepreneurship for Buzzrag.