OuttaDeeBox Podcast
OuttaDeeBox podcast is a pre-recorded bi weekly show geared towards supporting former and current inmates and their families in Wisconsin. Our mission is to inform listeners about community resources that can assist them in securing employment opportunities, housing, mental health and substance abuse support, with the goal of reducing recidivism in Wisconsin. We also give listeners and guests the opportunity to share their unique inspirational stories through spoken word and other forms of musical artistry.
Contributors
Guests
Peter Gray
Peter Gray (he/him) is a recovering Wall Street recruiter who now recruits social impact leaders and
fights bias in hiring.
As founder and CEO of Peter Gray Executive Search, based in Madison, Wisconsin, he guides
nonprofit organizations and social impact employers through strategic hiring. His placement experience
includes 37 CEO leadership successions, including four at affordable housing organizations.
Peter also trains employers on diversifying hiring outcomes and coaches individuals on overcoming
bias in job search and career advancement.
Peter began his career in executive search at Korn Ferry in New York City. Before that, he was a
management consultant at CSC Index, the firm that pioneered business process reengineering.
Peter gives back as a volunteer adviser, fundraiser, and board member for nonprofit and civic
organizations.
Shanyeill McCloud
Shanyeill McCloud didn’t just build Clean Slate Pardon Help Desk — she is Clean Slate.
This work isn’t theory for her. It’s a lived experience. It’s personal.
As someone who has navigated the justice system herself, Shanyeill understands what it feels like to be judged by your past and how hard it is to prove who you’ve become. She built Clean Slate Milwaukee from that place: not to help people ask for pity, but to help them walk in prepared, confident, and unapologetically transformed.
With over 12 years of experience in the Wisconsin pardon process, Shanyeill has helped hundreds of people turn their stories into strategies. She's not a lawyer—and that's the point. She's a voice for the overlooked, a guide through the noise, and a coach who shows up with honesty, grit, and clarity.
This isn’t just a job for her. It’s her mission.