What happens when three friends who’ve walked through the darkest valleys of the criminal justice system come together to create something that could change everything for millions of people?
When I sat down with my good friends Jeff Grant and Drew Chapin for this special episode of Nightmare Success, I knew we were about to dive into something that could fundamentally change how our country handles criminal justice reform. This wasn’t just another conversation, this was a masterclass in turning personal setbacks into powerful purpose.
Jeff Grant, co-founder of the White Collar Support Group and a reinstated attorney, has been at the forefront of criminal justice reform for years. Drew Chapin, founder of The Discoverability Company and entrepreneur who’s been speaking at college campuses around the country, brings a unique perspective on how to rebuild after hitting rock bottom.
Together, we explored the Federal Expungement Initiative, a groundbreaking effort that could provide an off-ramp for millions of people currently trapped in the federal criminal justice system.
“There’s nothing preventing Congress from passing a federal expungement law,” Jeff explained, quoting Rachel Barkow from NYU Law, a former US Sentencing Commission member and Justice Scalia’s law clerk.
What makes this initiative so powerful is that it addresses a fundamental flaw in our current system: there’s no way out. While 50 states (except Alaska) have some form of expungement, there’s no federal statute for expungement.
This means that someone convicted of a federal crime – regardless of how much they’ve transformed their life – carries that label forever. As Drew pointed out in our conversation, “You called me an ex-felon, but I’m not an ex-felon. That status remains despite having paid the price.” This distinction is crucial because it highlights the permanent nature of federal convictions and why the Federal Expungement Initiative is so desperately needed.
Jeff’s personal journey illustrates the transformative power of redemption. After serving time and getting his law license reinstated, he experienced what he described as “a hand being passed over me that this guy is okay.” The impact was profound, not just on his self-esteem, but on his family. “There’s a big difference between ‘this is my father, he went to prison’ and ‘this is my father, he’s a lawyer,'” Jeff shared.
What we’re talking about is creating a pathway for millions of people who have served their time, paid their debt to society, and are ready to contribute meaningfully to their communities.
The Federal Expungement Initiative is about creating a system that recognizes redemption and provides hope. The proposed law would likely require seven years of post-release good behavior, steady employment, and community service before someone could even apply for expungement. It’s a rigorous process that ensures only those who have truly transformed their lives would qualify.
“This is like a long-term project,” Jeff explained. “It could be seven years post-release before you even qualify for an expungement. So this is like a long-term project. And very different than the climate of pardons right now.”
What excites me most about this initiative is how it addresses the broader issue of community responsibility. For someone to qualify for expungement, they need to have a job for seven years—which means someone has to give them a job. They need to do volunteer work—which means someone has to allow them to volunteer. It takes an entire community to make this work, and that’s exactly the kind of cultural shift we need.
Drew’s approach to his own reentry exemplifies this philosophy. “I disarm it in a way by owning it,” he explained. “My thought process on that has simply been to just open it up. And then I have nothing to worry about.”
The White Collar Support Group, which meets every Monday night on Zoom, has become a lifeline for over 1,600 members. “There’s probably about 40 people online” on a typical Monday night, Jeff shared. “And to me, my favorite thing is when someone comes on for the first time and they’re scared … and they can’t believe that, oh my God, I’ve been going through this alone for some time years. And there’s like 40 people here who are going to give of themselves freely and share and provide me resources.”
This community aspect is what makes the upcoming White Collar Conference on October 11th so powerful. With speakers like Jeffrey Tuben (CNN commentator and author of “The Pardon”), Joe Bankman (Sam Bankman-Fried’s father), and a panel on the Federal Expungement Initiative featuring Mark Osler and Doug Berman, this isn’t just a conference, it’s a celebration of our movement.
What struck me most about our conversation was the sense of urgency and hope. We’re at a unique moment in history where criminal justice reform is gaining momentum, and the Federal Expungement Initiative represents a practical, achievable solution that could change millions of lives.
“We’re not doing it just for ourselves,” Jeff emphasized. “We’re doing it for anybody and everybody who has been convicted of a federal crime.” This isn’t about special treatment—it’s about creating a system that recognizes human potential and provides a pathway to redemption.
As our conversation came to a close, I was left with a profound sense of gratitude for having the opportunity to share this story.
Join the Movement for Second Acts
If you’re interested in learning more about the Federal Expungement Initiative, visit federalexpungement.org. And if you want to be part of the conversation about criminal justice reform, join us at the White Collar Conference on October 11th at 9am Eastern. You can register at whitecollarconference.com.