One Mistake Shouldn’t Define A Life: How This Nike Executive Is Rewriting The Rules

I'll be honest with you: the day I went to jail for the first time in my life was one of the most enlightening days I've ever had.

My colleagues led a career development program at Rikers Island—two pilot cohorts using my method for career pivots — and I went to celebrate the program’s completion. What I found on the other side of those walls shattered my assumptions. The men in that room were perceptive, thoughtful, and hungry. One participant noticed the subtle Native American influences woven through my writing — something most of my other clients had never picked up on. These were people who, given a fair shot, were ready.

That experience shapes everything I write and develop about career change, and it’s why I knew, the moment I listened to Larry Miller and Ken Oliver speak at South by Southwest, that their story demanded its own space.

Miller is the founder of the Justice & Upward Mobility Project (JUMP), Chairman of the Jordan Brand Advisory Board at Nike, and author of the memoir JUMP, co-written with his daughter Laila Lacy. Oliver is JUMP's President and CEO. Both are 2026 Compassionate Leaders Circle Award recipients. Both have records. And both are among the most compelling leaders I've ever interviewed.

From the Streets to the Suites — and Back Again

Miller’s story is well documented and worth reading in his own words: a childhood in West Philadelphia, choices that led to prison, and a decision — made behind bars — to earn an accounting degree. When a well-meaning advisor suggested he settle for a clerk’s job afterward, he refused. "I put in the same effort, got the same degree," he told me. "Why should I take something less than the next person?" That refusal to accept lowered expectations carried him to being Chairman of Nike’s Jordan Brand and leading the Portland Trail Blazers.

Oliver's path is different but equally instructive. He grew up in South LA, was sentenced to life under California's three-strikes law at 26 as a passenger in a stolen vehicle, and spent 24 years in prison — nearly a decade of it in solitary confinement. He read over a thousand books, taught himself constitutional law, and filed a landmark civil rights lawsuit challenging the conditions of his confinement. With Stanford University and the law firm Mayer Brown at his side, he won an unprecedented settlement — and his freedom.

When these two men finally met, something clicked. Miller used to tell his friends on the stoops of Philadelphia that if he could just make five hundred dollars a week, he’d leave the streets. Oliver said the same thing to his friends in South LA, a generation later — his number was a thousand. Two men, three thousand miles and a generation apart, having the same internal conversation about access. As Miller likes to say, they built JUMP to prove that one plus one can equal three.

A Talent Strategy, Not a Charity

JUMP is not a traditional reentry nonprofit. Oliver calls it a narrative change organization — a national movement using the cultural power of sports, business, and entertainment to shift how America sees the roughly 80 million people living with a record, a number projected to reach 100 million by 2030.

The strategy is deliberate. Working with Boston Consulting Group, JUMP mapped the U.S. cities with the highest recidivism and unemployment rates among justice-impacted people and committed to building localized coalitions — business leaders, philanthropists, policymakers, universities, and community organizations — in 30 cities over the next 15 years. Oliver moved to Charlotte, the first JUMP City, to build the model himself. The goals are audacious: a million jobs and a cut in recidivism in half within two decades.

The data says it’s possible. A Harvard Business School case study built on Miller's life — now taught in its Executive MBA program — cites research showing that when returning citizens learn a marketable skill leading to a livable wage, recidivism drops from 77 percent to 30 percent. With a bachelor's degree, it falls to 6 percent. With a master's degree, it hits zero.

Miller watched 250 C-suite executives study his case. At the start of class, the professor asked whether they would have hired Larry Miller knowing his record; roughly 80 percent said no. By the end, the numbers had flipped. "Those are the decision makers," Miller told me. "How do we reach them and change the narrative for them?"

The Barriers Are Built Into the System

Here is what Oliver wants every leader to understand: 95 percent of companies run background checks, and automated screening — increasingly powered by AI — filters people out before a human ever sees them. Oliver worked inside one of America's largest background check companies and watched applicants get screened out for fishing license violations. Layer on more than 44,000 collateral-consequence laws restricting jobs, housing, and occupational licenses, and you have what he plainly calls legal discrimination — a system that hands someone $50 and a bus ticket, then closes every door.

Miller’s own career turned on a single moment of grace. When the Trail Blazers were hiring him, a security check dug up his record. The executive who wanted him agonized, then called owner Paul Allen. Allen's response: "How long ago was this? Don't worry about it."

Every leader reading this has the power to be Paul Allen in someone's story.

What Compassionate Leadership Has to Do With It

At Compassionate Leaders Circle, we’ve found that compassionate leaders share three practices: self-compassion, vulnerability, and translating both into making the world better through compassionate actions.  Miller and Oliver embody all three. They forgave themselves, they tell their stories publicly, and they’ve turned that energy into infrastructure — including executive-caliber leadership training for justice-impacted people, because, as Oliver puts it, we should look at them "the same way we look at somebody who graduated from Yale."

April is now recognized as Fair Chance Month, honoring people who face and overcome the challenges of living with a record. But fair chances shouldn’t be seasonal. If you lead an organization, start here: read Miller’s book. Join the Second Chance Business Coalition, which Miller now co-chairs alongside Jamie Dimon, CEO and Chairman of JPMorgan Chase. Support JUMP through hiring partnerships, funding, or amplification. And audit your own hiring: are algorithms rejecting capable people before anyone meets them?

I keep coming back to what Oliver told me: everyone wants safer communities and a stronger economy. Second chances deliver both. The business case says you should. The human case says you must. Listen to my interview with these amazing leaders here and learn more about all the 2026 Compassionate Leaders Circle Award Honorees here.