90: Second Chances, Sound Leadership: Larry Miller and Ken Oliver on Building the Justice & Upwar...

What does it take to build a career — and a life — after the justice system has already written you off? In this conversation, Laurel sits down with Larry Miller, founder of JUMP, and Ken Oliver, JUMP's President and CEO, to talk about second chances, systemic change, and the leadership lessons hiding inside both of their stories. Larry and Ken met four years ago and quickly realized they were building toward the same goal from different angles. Together they founded JUMP — a workforce development and entrepreneurship organization for people coming out of incarceration — built around a simple but radical belief: this isn't charity, it's an untapped talent strategy. What You'll Hear • Why Larry and Ken built JUMP around sports, entertainment, and corporate partnerships — and how "one plus one can equal three" • The story behind Larry's hiring at the Portland Trail Blazers, and the moment owner Paul Allen asked one question that changed everything: "How long ago was this?" • How a Harvard Business School case study on Larry's life flipped a room of 250 executives from 80% "wouldn't hire him" to 70% "would" • Ken's path from a life sentence to running JUMP — and the mentor who told him "you can teach everything under the sun... but you can't teach drive" • JUMP's four-part strategy: skill-building through apprenticeships, local coalition-building between CEOs and community organizations, shifting media narrative, and policy reform • The recidivism data that changes the entire conversation: without intervention, 77% of people return to the system within two to three years — but that number drops to 30% with a marketable skill, 6% with a bachelor's degree, and 0% with a master's degree • JUMP Cities: how Larry and Ken identified 30 target cities (starting with Charlotte) using a landscape analysis built with Boston Consulting Group • Why entrepreneurship training matters — and why it has to be real training, not "a $5,000 business plan and don't dream bigger" • Larry's appointment as co-chair of the Business Roundtable's Second Chance Business Coalition alongside Jamie Dimon • What "compassionate leadership" looks like when it's not a talking point but an operating system Memorable Moments • "In this world, talent is distributed equally, but opportunity is not." — Larry Miller • "We're not asking people to be grateful for a second chance. We're asking employers to recognize they've been overlooking an enormous pool of capable, motivated talent." — Ken Oliver • "How long ago was this? Don't worry about it." — Paul Allen, on learning about Larry's record before hiring him About Our Guests Ken Oliver President & CEO, Justice & Upward Mobility Project (JUMP) Charlotte, NC Ken Oliver is the President and CEO at JUMP. Before his impressive career at the intersection of law, public policy, and philanthropy, Oliver spent 24 years in prison, including nearly a decade in solitary confinement. He successfully challenged the conditions of his confinement, securing an unprecedented settlement and his freedom through a landmark civil rights lawsuit in partnership with Stanford University and Mayer Brown. Oliver and his team are bringing together business leaders, policymakers, culture changers, and communities to drive sweeping, lasting change that gives people well-deserved second chances. A cornerstone of that work is confronting the very real problem of stigma and shifting narratives around people with records. April is now designated as Fair Chance Month (https://www.prisonfellowship.org/abou...) , a recognition of those who face and overcome many of the challenges associated with arrest records in the United States. Larry Miller Founder, Justice & Upward Mobility Project (JUMP) Chicago, IL Larry Miller is the Founder of the Justice & Upward Mobility Project (JUMP (https://www.jumpproject.org/) ), a national movement harnessing cultural influence to unlock education, employment, and economic mobility for youth and adults impacted by the justice system. He is also the current Chairman of the Jordan Brand Advisory Board, a division of Nike Inc. He has garnered international respect for his reputation as an inspirational leader who understands how to build innovative, cultural, and premium businesses in the world of sport and lifestyle, establishing the standard for athletic luxury footwear and apparel. His memoir, JUMP (https://www.amazon.com/Jump-Streets-S...) , co-authored with his daughter Laila Lacy, shares the organization's name and tells the story of his journey from the streets of Philadelphia to prison and ultimately to leadership at Nike and the Portland Trail Blazers. Learn More ...