Rapper Meek Mill and entrepreneur Michael Rubin, CEO of e-commerce giant Kynetic, have very different relationships with failure—out of necessity. While Rubin built his career (which includes founding and selling GSI Commerce to eBay for $2.4 billion in 1999, founding sports-merchandising pioneer Fanatics, and purchasing an ownership stake in the Philadelphia 76ers) on making mistakes and learning from them, Mill grew up in an environment without second—let alone third, or fourth—chances.
“For me, I think failing is great, because if you fail fast and you learn how to fail, you can use that to build your next success,” Rubin said on Wednesday at Fast Company’s Innovation Festival. “That’s great for mainstream America, [but] it doesn’t work that way for poor people, it doesn’t work that way for people who grew up in Meek’s environment. For Meek, he doesn’t even need to fail, he still goes to prison.”
Rubin and Mill joined Fast Company to discuss the Reform Alliance, an organization they cochair that aims to reform probation and parole laws in the United States. The Alliance was inspired by Mill’s own experience, after the rapper was sentenced to two to four years in prison in November 2017 for technical violations to his probation. (Mill was arrested for gun and drug charges in 2007, when he was just 19 years old, and was sentenced to 11 to 23 months in county jail, to be followed by 10 years of probation. That conviction was overturned this summer.) During the hour-long discussion, Mill and Rubin shared how their unlikely meeting at a 76ers game led to a close friendship that eventually opened Rubin’s eyes to a side of the criminal justice system he didn’t know existed. Rubin was shocked, for example, when early in their friendship the Philadelphia-based Mill told him he couldn’t cross state lines to visit Atlantic City without permission from his probation officer. Mill, likewise, couldn’t believe Rubin didn’t know more about how probation worked—or how precarious it is for people on it, who can be sent back to jail for any number of small violations, including failure to pay court fines, a missed court appearance, and even jaywalking.
“My mind was blown, I’m like ‘my rich white friend doesn’t even think this is possible,'” Mill said of his probation terms. “It baffled me how surprised [Rubin] was. And as I met more people who cared about this situation they were like, ‘That’s not normal, Meek.'”
When Mill was called back to court in 2017 for minor probation violations that included popping wheelies on a dirt bike in New York (for which he was arrested, but not charged), Rubin attended his court appearances. “I thought there was zero chance he was going to prison,” Rubin recalled.
“He thought it was almost impossible for me to go to prison without committing a crime,” Mill explained. “When I called him [after my sentencing], I was like ‘If this was you in the courtroom, this wouldn’t be this way.’ And he got a chance to see it firsthand.” On the day of Mill’s sentencing, Rubin immediately called NBA commissioner Adam Silver to tell him he’d “do whatever it takes to get [Mill] out” and got the commissioner’s blessing to pursue his campaign to free the musician.
Mill credited Rubin’s business background with helping to get him released on bail in April 2018 and get his own conviction overturned this past summer. “Mike taught me to never accept no,” Mill said. “I thought I was never getting out of prison, I was like ‘this white man is crazy.’ I come from an environment where we see the no all the time, but he showed me that you don’t have to do that.”
Now the two have turned that approach into the Reform Alliance. Rubin explained that while the criminal justice system is in need of overhaul in several key areas, the Reform Alliance—which has $50 million in investment from partners including Jay Z and Patriots owner Robert Kraft—will get results by honing in specifically on the 4.5 million Americans who are on probation and parole. “We’re running this like a business, and that’s how we’re going to get results.”
He learned to focus like this, he said, from business mistakes he had the privilege of making throughout his career. “When I sold GSI Commerce [to eBay in 2011], I felt we had a good outcome, but I felt like it would have been a lot better had I focused more,” Rubin said. “I wanted to take the mistakes and use them to make ourselves more successful with the Reform Alliance. We’ve had lots of people try to distract us,” he added, “but we’re like a dog on a bone on probation and parole reform, going state by state, changing laws, and educating people.”
Mill, in turn, has educated Rubin and other powerful business figures involved in the Alliance “on my side of the world,” he says. “Mike grew up in business, I grew up in survival.” It was the pair’s friendship, Rubin agreed, that was the catalyst for his education and now his work on probation and parole reform. “I didn’t approach this in any way other than watching my friend get taken away,” Rubin said. “I wanted to get this fixed at any cost.”
The Alliance is currently working on changing laws in Mill’s native Pennsylvania and next will take on Georgia—which has the most parolees of any state in the country. They’re also working on educating the general public about the issue. “Most people are like me, they want to believe that the system works well,” Rubin says. “Once you educate them, most people are good and want a fair system.”
“People like me get to grow up and fail and learn,” Rubin explained. “People who grow up like Meek should get that opportunity, too.”