The story of Michael Rubin was interesting enough before last November 6, a day he refers to as though it lives in infamy. “November 6, 2017, that was life-changing,” Rubin says today, sitting in his Conshohocken office in shorts, a T-shirt and flip-flops.

Before that day, here’s what you would have known about Rubin. He was, in his mid-forties, a hard-charging billionaire, having grown up as something of a business prodigy in the suburbs of Philadelphia. Born to a psychiatrist mother and a veterinarian father, Rubin was somehow blessed with an entrepreneurial gene. He started his first businesses at eight years old, selling vegetable seeds door to door, then overseeing neighborhood kids—his first employees—in a snow shoveling business. 

At 12, he opened a ski tune-up shop in his parent’s basement. At 14, using Bar Mitzvah money, he opened Mike’s Ski Shop in Conshohocken. Before graduating high school, he had five stores; to his parents’ chagrin, he bought a Porsche before he could legally drive. He made his first million before he could legally drink.

When eBay bought Rubin’s e-commerce company, GSI Commerce, for $2.4 billion in 2011, it catapulted Rubin into the elite of the American C-suite. Today, Rubin, a stocky ball of energy with infamous attention deficit disorder, is known as a relentless boardroom competitor (“no means yes”) who, mostly through sheer force of will, is remaking the e-commerce space through his three companies: Fanatics, Inc., a licensed sports merchandiser; flash sellers Rue La La and, most recently, Gilt; and Shop Runner, a retail benefits program.

“Before that day, you had a problem and you came to me? I’d write a check,” Rubin says. “Now, no joke, lately I’ve been spending about a third of my time on Meek’s situation and criminal justice reform.”

On top of it all, he’s one of the owners of the Philadelphia 76ers, which is how he and rapper Meek Mill first came to know one another. At an NBA All-Star game, Rubin and his now 12-year-old daughter Kylie found themselves courtside next to Mill and his then-girlfriend Nicki Minaj—Kylie’s favorite at the time. A bond between Rubin and Mill formed, Rubin says, over their shared inquisitiveness. Rubin’s attention may famously wax and wane, but he asks rapid-fire questions, the wheels always turning, processing answers before breathlessly jumping to the next new idea. Mill, Rubin found, has the same sense of curiosity, grilling the billionaire on the art of deal-making.

So that’s a pretty good life story right there, no? But then last November 6 happened. On that morning, Mill called his billionaire friend, a not uncommon occurrence. How close are the billionaire and North Philly born and bred rapper? For the last five years, they’ve spoken or Facetimed multiple times every day. Along with the third member of this most unlikely triumvirate, 77-year-old Robert Kraft, billionaire owner of the New England Patriots, they regularly vacation together. (Paging Mark Burnett: Is that a reality show waiting to happen, or what?)

On that day last November, Mill called on the morning of yet another probation hearing—he was arrested in 2007 on gun and drug charges and still has six years left of probation. The rapper said, “I don’t have a good feeling about this.” Rubin pooh-poohed his friend’s worry. After all, the judge was calling Mill back before her because authorities had seen him on social media popping a wheelie on a dirt bike, and for being in a minor altercation in the St. Louis airport; no charges were filed in either case. Still, Rubin decided to show up for moral support, despite having to surrender his phone before entering the courtroom, stirring panic.

“Before that day, you had a problem and you came to me? I’d write a check,” Rubin says. “That was my attitude. I was focused on my businesses. Then, when I saw something like this happen to one of my really good friends, you have to take action. Now, no joke, lately I’ve been spending about a third of my time on Meek’s situation and criminal justice reform.”

What he saw that day was a judge, Genece Brinkley, hellbent on sending his friend away for an astounding 2 to 4 years for violating probation—despite the fact that neither the prosecutor or probation officer were recommending any jail time for such minor infractions. But Brinkley had long been oddly obsessed with Mill, once even showing up at Broad Street Ministries when Mill was supposed to be feeding the homeless and admonishing him for folding T-shirts instead.

“Listen, I manage about 8,000 employees at our companies, and part of the job is to be an evaluator of talent,” Rubin says. “Same thing in sports. A core part of what you do is evaluate people. And when I sat in the courtroom that day and I watched how she conducted herself, how she treated the probation officer, the district attorney, and Meek with such disrespect, it was an out-of-body experience. I spoke before she sentenced him, and she didn’t even look at me. This can’t be the justice system, can it?”

When Brinkley dropped her sentencing bombshell, Rubin says, Mill and he looked at each other, both tearing up. And then his friend, his pockets hurriedly emptied, was cuffed and gone. Later, Kylie would say to him, “Dad, you’ve got to fix this.” He was one step ahead of her. Turning to the woman next to him, Rubin said through gritted teeth, “I am not fucking stopping until he’s out of jail. Period. End of story.”

“Look how much I’ve learned from Meek,” Michael Rubin says. “Look how much he has opened my eyes to shit I didn’t understand before. How lucky am I?”

She looked at him and said: “I’m not stopping until he’s out of jail.” Rubin didn’t know that he was talking to Desiree Perez, the COO of Jay-Z’s entertainment juggernaut Roc Nation. Perez has been called Jay-Z’s “secret weapon;” Billboard named her one of the most powerful women in music last year. Together, they turned what they saw as the injustice of that day into a cause celebre.

Suddenly, Stand With Meek Mill buses flooded the streets and #FreeMeekMill became a thing. On Thanksgiving, there was activist Anton Moore of Unity in the Community—Moore addressed the 2016 Democratic National Convention—solicited by Roc Nation to continue Mill’s tradition of handing out free turkeys on the streets in the rapper’s absence.

The increased attention led to a spate of stories about Brinkley that raised questions about her demeanor and tactics, painting her, among other things, as disturbingly litigious. Other stories cast serious doubt on the initial arrest of Mill in 2007 on gun and drug charges, given that the arresting officer, Reggie Graham, has since been disgraced.

For Rubin, it’s all been part of a game-changing process of self-education, one that began before Mill was sent away. He and Mill would argue about race late into the night. “He’d tell me there are two Americas,” Rubin recalls. “Like, we used to fight about it. I’d say, ‘Shut up, dude. Stop being such a cry baby. There’s one America. Stop with the bullshit.’” A couple hours after being led out of the courtroom in handcuffs, Mill called Rubin. “Now do you believe me?” Mill said. “I know you want to get this judge, but it’s bigger than that.”

“He was right,” Rubin says. “There are two Americas. It sucks. But, to me, that’s an opportunity. Like, we’re not going to end racism in a day. But let’s lessen it every year.”

Maybe Mill, a symbol now of a system in desperate need of repair, is, like his billionaire friend, in a stunning state of becoming. Maybe they’re both waking up.

The aperture of Rubin’s lens has extended beyond the particulars of Mill’s story. Along with Kraft, Jay-Z and other one percenters with a conscience, he’ll be forming a high-profile bipartisan organization to make change. Last week, he spent hours interviewing CEO candidates in search of a dynamic leader who can spark a movement. The more he dives in, the more Rubin learns that Mill’s story is not unique.

“You start hearing these crazy stories,” he says. “You know, this guy had a minor thing when he was a kid, smoking weed, and he was still on probation, so he went to jail for 10 years. Or this woman who wrote a $75 bad check, she’s seven months pregnant and because she had a prior crime, they put her back in jail, where she delivered her kid. Now the kid has no parent. It’s stupidity. The criminal justice system could not be more broken.

“Look, I have no involvement in politics because I hate people fighting. I’m a uniter. But someone’s gotta do something. The criminal justice system has 6.7 million people in it, 2.2 million in prison and jail and 4.5 million people on parole or probation. I just want to go into the system and address it with some business sense. We’re going to get one million people out of the criminal justice system in the next five years, and we’re going to be unrelenting about it. Jail should be for murderers and rapists. Let’s not put someone who smoked weed behind bars, okay?”

Rubin’s soliloquy about the system’s shortcomings matters so much because of who is saying it. First, he’s modeling for all of us who live lives of comfort that it’s never too late to become empathetic. It wasn’t a couple of months ago that he first heard himself described as “woke.” “I didn’t know what it meant,” he says, smiling sheepishly. “I thought it was a misspelled word.” He had to ask Kylie for the definition.

But there’s potentially some bigger meaning to Rubin’s middle-aged burst of social consciousness. If Rubin and Kraft—who also visited Mill in prison and who spoke to Mill by phone about the rapper’s plight while he and Rubin vacationed in the South of France—together can stimulate the business class, it could widen the constituency for reform beyond the already converted. After all, if Mill and Rubin are right that there are two nations when it comes to justice in America, that no doubt is owing to the voicelessness of those at its mercy. But, to further the strange bedfellows theme of this story, if the donor class suddenly aligns with the underclass, perhaps that will attract the attention of policymakers.

Rubin’s success owes mostly to indomitable will, but also to seeing opportunity for improvement where others don’t. Every business he’s bought has been fueled by the idea that We can do it better. How many African American kids caught up in the system who aren’t famous rappers might benefit from some outside force agitating for just that kind of solutions-based emphasis applied to the wild west that is our criminal justice system?

Of course, Rubin runs the risk of culturally deifying Mill, which could lead to backlash. To be clear: As I’ve written before, not only isn’t Meek Mill Nelson Mandela—as the author of rhymes like If you ain’t about that murder game then pussy nigga shut up/if you diss me in yo’ raps, I’ll get your pussy ass stuck up—his art to date doesn’t approach that of Pulitzer Prize-winning rapper Kendrick Lamar in terms of either literary heft or social consciousness.

But here’s hoping that’s about to change, too. Last month, at the BET Awards, Mill debuted his new song, Stay Woke, and it comments on, rather than glorifies, life on the street: It’s amazin’, this environment we was raised in/ On them papers, one mistake and I’m gettin’ caged in/ You get feel me, feel like the system tryna kill me…

Maybe Mill, a symbol now of a system in desperate need of repair, is, like his billionaire friend, in a stunning state of becoming. Maybe they’re both waking up.

If Rubin and Kraft together can stimulate the business class, it could widen the constituency for reform beyond the already converted. If the donor class suddenly aligns with the underclass, perhaps that will attract the attention of policymakers.

Clearly, Rubin is evolving. Last week, the New York media had a field day reporting that he’d closed on the most expensive penthouse ever sold downtown in New York City—$43 million, complete with a 5,000-square foot roof terrace with a private pool.

But, in person just days later, it’s not his newest plaything that brings him to life; it’s his newfound passion—for the first time in his life—for justice. He’s fixated on talking about his relationship with a 31-year-old rap star who, as Rubin points out, was arrested at 18 and has spent the last 13 years in the system. “People have said to me, man, Meek is so lucky to have you as his close friend,” Rubin says. “I’m like, man, I’m the one who’s lucky to have him as a close friend.”

He pauses, and fixes me with one of those powerful, determined stares that no doubt makes business opponents cower, but what comes out next is introspective—not bombastic. “Look how much I’ve learned from Meek,” Michael Rubin says. “Look how much he has opened my eyes to shit I didn’t understand before. How lucky am I?”