Business Spotlight with Shannon Ross from The Community

Jackie Zach
January 1, 2025

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This episode features the powerful story of Shannon Ross who shares his remarkable transformation journey, from spending 17 years in prison to becoming a leader in the community, advocating for the system-impacted. Since his release in 2020, Shannon has immersed himself in multiple impactful projects, including his organization, The Community, which works to correct the narrative around individuals with criminal records. He credits his success to a combination of personal resilience, strong support networks, and the lessons learned from past failures. Shannon emphasizes the importance of honesty, recognizing weaknesses, and adapting to challenges as crucial elements of his personal and professional growth.

One of his major endeavors is the University of Reentry, a groundbreaking project aimed at providing a supportive, campus-like environment for people reintegrating into society. This initiative strives to offer not just education but also empowerment, helping individuals reshape their futures. While he and his partner face significant challenges in funding and managing such a large-scale project, Shannon remains driven by his vision of fostering exploration, creativity, and support for those who need it most. His journey is a testament to the power of community, mentorship, and the ability to rise above adversity.

 

Podcast Transcript:

Jackie Zach: Hello, everyone! This is Coach Jackie Zach, and I’m thrilled to have Shannon Ross with us today. Shannon is the founder and executive director of The Community. Since his release from prison in 2020 after serving 17 years, Shannon has accomplished an incredible amount. He is a founding partner of a multi-dimensional justice solutions firm called Paradigm Shift, an EdTrust fellow, a Represent Justice alumnus, a consultant at Marquette University, and a graduate of the Master’s in Sustainable Peacebuilding program at the University of Wisconsin-Milwaukee.

Born and raised in Wisconsin, Shannon somehow cheers for sports teams on the coasts—but I won’t hold that against him. He’s also a first-time father—congratulations! In his downtime, he enjoys basketball, athletic activities, or stand-up comedy. What I find especially inspiring is that Shannon considers his work an accomplishment stemming from the opportunities and skills he’s been given. 

Above all, he takes pride in his ancestry and his identity as a biracial person in America. It’s an absolute pleasure to welcome Shannon Ross to the show today. Welcome, Shannon!

Shannon Ross: Thank you so much, Jackie.

Jackie: Sure! Tell us a little bit about your personal story.

Shannon: In the realm of storytelling—where I spend a lot of my time working in community spaces—I always wonder: do I give the short, medium, or long version? But as you already mentioned, I was born and raised in Milwaukee. I did my freshman year at UW-Milwaukee, and then I made a life-altering decision that led me to spend 17 years in the Wisconsin prison system.

Since my release three and a half years ago, I’ve been fortunate to connect with incredible opportunities. I’ve also leaned into my natural skills, which have helped me seize those moments and turn them into something positive. While my life choices once took away from my community, I’ve been dedicated to giving back ever since. My ultimate goal is to create a world I’d want my son to grow up in—a world I wish I had grown up in.

Jackie: What’s a funny story about you that your family loves to tell and you’re okay with sharing?

Shannon: One story comes to mind right away. When I was about four or five, my dad—who is mixed-race but has a darker complexion, looking Cuban at the time—was my main caretaker since my mom was working. We lived in a neighborhood with a large Latino population, and as a kid, I was pretty racially ambiguous. I could pass as Arab, Puerto Rican, or Mexican, and people often assumed my dad and I were Latino.

One day, we were on a bus, and I wasn’t behaving. I refused to sit down, and people around us started to question whether he was really my dad. Someone called the police. The police came, and after showing his ID and calling my mom, they confirmed everything and let us go.

Once back on the bus, my dad was trying to tickle me to cheer me up, and I said, “Stop it, Daddy!” He laughed and said, “Oh, now I’m Daddy!”

Jackie: That’s hilarious—you couldn’t have said that earlier?

Shannon: Exactly!

Jackie: So, with everything you’ve accomplished, tell us how The Community came to be. At what point did you feel confident about running your own organization?

Shannon: It wasn’t a single moment—it was a gradual build-up of experiences. I always admire people who can pinpoint the exact time they gained confidence, but for me, it was more about doing small things that grew into larger projects. Over time, I realized I could handle the responsibility.

I’ve also learned that how you respond to failure matters more than having the right skills or experience. Facing setbacks and adjusting my expectations taught me resilience. I focus on creating environments that increase the likelihood of success while staying realistic about challenges.

A big factor in my journey was growing up with supportive and capable people around me. I didn’t experience adverse childhood experiences (ACEs), which many people I work with have endured. These experiences can significantly affect confidence and decision-making later in life. I was fortunate to have people who poured empowerment into me—whether intentionally or not.

I think we often underestimate how much our past shapes us. No one achieves anything alone; we’re all influenced by what’s been given to us in some way. That foundation of support has been instrumental in my path.

Jackie: That’s wonderful. Could you tell us more about the community work you’re involved in and what you do?

Shannon: Sure. It’s always interesting to answer that question because I wear so many hats. Right now, I’m literally wearing “The Community” hat. I’m involved in higher education for prisons, consulting, and other projects outside the community. But if I start with how it began, it all started with a newsletter.

My mom, a soon-to-retire newspaper editor, and I put it together. She worked for a small construction paper in Milwaukee. A friend of mine, who had just gotten out, worked at a copy shop and was a polymath—he knew tech and law and later became a professional digital graphic designer with multiple degrees. Another retired friend also helped us get started. I wrote the content, collaborated with my friend on the design, and we printed and sent it to 200 people initially.

Over time, it became the most widely read publication in Wisconsin’s prison system. Our latest issue will reach over 8,000 people—about 40% of Wisconsin’s prison population. When I got out three and a half years ago, I began pursuing another idea: correcting the narrative around people with criminal records.

We highlight their successes, humanity, and agency through presentations across and beyond Wisconsin, a video series (our third season premieres at our annual celebration on August 24 at the Medical College of Wisconsin), and a podcast. Our work involves both correcting the narrative and internal efforts, which we refer to as ‘pre-entry.’ This has now expanded beyond just a newsletter to include a learning platform and a fellowship. Recently, we received a significant grant from the Medical College of Wisconsin to develop a community healthcare worker training program for individuals in prison. This program will equip them with a certification and skill set that can help them secure employment upon release.

Our goal is to help the system-impacted community—those with records and their connections—and the broader community come together on equal footing. It’s about seeing people for who they are, beyond mistakes and biases, and building a stronger community together.

Jackie: Wow, that’s incredible! Can you share a story about someone who pushed or inspired you to achieve such a huge impact, growing from 200 readers to 8,000?

Shannon: There are so many moments when someone inspired me or held me accountable. If I think back to the beginning, my mother comes to mind. While I was incarcerated, she supported both me and my father, who also needed care and support. She’s always carried immense responsibility, and seeing her dedication has profoundly influenced me.

Growing up, we clashed—me being a teenage boy and a person of color, while she was a white woman from small-town Wisconsin. We often didn’t see eye to eye. But in prison, I witnessed her unwavering commitment—not just to me, but to everything she does. That’s stuck with me. It drives me to see things through, even when it’s not healthy or convenient. If I say yes to something, I feel compelled to finish or ensure someone else can take over.

Even now, people push me to manage my time better. I guess I’m what some call “time-blind,” which I’m working on. Being late can harm relationships and opportunities, so I’m trying to improve. I struggle with estimating how much time I need to prepare for things, and sometimes, I’m late simply because other commitments run long. But I’m learning to prioritize and plan better. Those lessons shape how I approach my work and relationships.

Jackie: Well, again, that’s a pretty typical business owner experience, right? Wearing all the hats and juggling everything. So, what has been your biggest learning as a business owner?

Shannon: I keep coming back to how you respond to things. At one point during my brief time as a free person—it’s been about three and a half years now—I had a trucking company. Just three months after I got out, I started it, and about a year and a half later, we dissolved it. Around eight months ago, I went through personal bankruptcy because of it.

For a while, I struggled to accept the reality of that situation. Holding on to the business was ruining my friendship with my partner and affecting me personally. It was draining—I was in graduate school, my son had been born, and sometimes I’d end up driving a truck on the third shift when someone didn’t show up.

It was a humbling experience. I had to admit the failures and the mistakes I made so I could move forward and make better decisions. I think we often get prideful and sensitive about admitting failures, especially as leaders. We love to highlight the upside, the wins, and the social media version of our lives, but we don’t talk about how difficult it really is.

It frustrates me when people say, “You can do this too, just follow XYZ.” Because in reality, there’s no such thing as “just XYZ.” They’re leaving out 23 other letters before XYZ.

The biggest takeaway for me is the importance of honesty—with yourself and others. When hearing someone’s success story, ask: What were the struggles? What didn’t they know? That’s the information I need. It makes it easier to respond to challenges without shame and see failures as lessons. The most human thing you can do is fail. The worst thing you can do is not admit it or be honest about it.

Jackie: Right. And really, failing is just your first attempt at learning, right? As long as you take away the lessons. Bankruptcy is a huge challenge, but what other challenges have you faced? And who helped you get through them?

Shannon: Other challenges I’ve faced are unique to my situation as someone reentering society after a long time away. What I’m about to say might sound conceited, but I believe in recognizing individual strengths. I can also acknowledge my weaknesses, which might sound humble.

One of my strengths is being quick to figure things out and adapt. I didn’t experience the common overwhelming feelings many people face after incarceration, like struggling in grocery stores or crowded places. During my 17 years inside, I deliberately maintained discomfort so that transitioning back to society would be easier. I didn’t seek comfort while I was there because I knew it would make adjusting later more difficult.

Even so, I still struggle in certain areas, like social interactions. I’m socially awkward and still learning to be better in groups. I can play the extrovert, but I’m really an introvert at heart. Another challenge is navigating professionalism—do I always wear suits and try to impress people, or let my personality and skills speak for themselves? I’m still finding my balance in the social and business world, often stepping into opportunities I’m not entirely ready for and figuring it out as I go.

Jackie: One thing you mentioned was staying uncomfortable for 17 years, and that’s a powerful lesson for business owners. We naturally seek comfort, but your approach of embracing discomfort to prepare for the future is inspiring. For the business owners listening, those are huge lessons. Thank you for sharing that.

If you had to pick three people who’ve been most instrumental in your journey as a business owner, who would they be?

Shannon: Just three? Constraints can spark creativity. First, my mom—nothing I do would be possible without her presence and support.

Second, my partner Adam. We balance each other in a unique way, combining our differences and similarities to create opportunities and accomplish a lot together.

Third, I’d say the field of business literature. While I was inside, I didn’t have role models around me, but I read books like Inc. and watched shows like Shark Tank. That exposure gave me guidance and inspiration.

I often joke that my mentors were dead authors—people I never got to meet, but who laid the foundation for my journey. Literature, TV shows, and even social media have played a huge role in showing me what’s possible and how to navigate the entrepreneurial world.

Jackie: Awesome. So, what’s the next big thing for you and your business over the next one to three years? Where do you see growth opportunities?

Shannon: That’s an interesting question because I have a few projects happening in different spaces, but they’re all connected. One major project we’ve been working on for years is called the University of Reentry. Right now, we’re looking at the possibility of acquiring a large 48,000-square-foot building in Milwaukee, near Walker’s Point, close to downtown.

This would be a revolutionary project, bringing together different organizations to create a campus-like environment that fosters exploration, creativity, and support—similar to what universities do for students. Universities transform individuals into promising and powerful human beings, and we aim to do the same for people reentering society. We want to take individuals who are struggling and help them become valuable members of their own lives, families, and communities.

Having that kind of supportive atmosphere would be transformative. This project ties together everything I’m involved in and represents a huge step forward in the work we do. It’s ambitious, but I believe it could be revolutionary.

Jackie: That’s an amazing vision. What do you see as the biggest challenge in making it happen?

Shannon: My partner Adam and I are navigating unfamiliar territory. We’re learning about funding and managing such a large real estate project, ensuring sustainability, and overseeing all the moving parts within the building.

The biggest challenge is not only convincing others we can pull this off but also being mindful of our blind spots. We need to listen to advice and feedback carefully, even when it doesn’t initially seem applicable. Sometimes, people give advice that isn’t relevant to our situation, but we can’t dismiss it outright.

This is a new area for us, so we need to approach it differently than we’ve handled smaller projects. It’s about staying hyper-aware and open to learning while also trusting our instincts when appropriate.

Jackie: Right. So, what advice would you give to a business owner trying to do it all on their own?

Shannon: First, have an honest conversation with yourself. Are you truly ready for the hard work? Running your own business requires at least twice the effort you’d put in working for someone else. If you’re not prepared for that, consider partnering or working for someone else instead.

This path requires adaptability. You can’t say, “I don’t know how to do that” and leave it at that. You either learn or fail—it’s that simple.

There’s plenty of information available online—Google, YouTube, and elsewhere. The key is being willing to listen and learn, rather than thinking you’re immune to common pitfalls. So, really ask yourself: Are you genuinely ready for this challenging yet rewarding journey?

Jackie: That’s great advice. It sounds like you’ve been blessed with incredible people who’ve helped you along the way. What would you like to say to them?

Shannon: Before I answer that, I want to clarify something from my last answer. While the journey can be tough, it’s also deeply rewarding. Even when I’m overwhelmed, I remind myself that these are my challenges—ones I chose, not someone else’s.

There’s beauty in the struggle. When things work out, it’s incredibly empowering to look back and say, “I created this.” It’s about designing a life you’re proud of, even if it’s hard.

Now, to your question—Adam and I have talked about hosting a celebration in the future to express our gratitude to everyone who has supported us. I’m someone who believes in paying it forward. The support I’ve received has never been wasted, and I hope people see that their investment in me wasn’t in vain.

I may not always get everything right, but I’m sincere and committed to making their support worthwhile. My way of saying thank you is to continue extending that kindness and support to others.

Jackie: Well, Shannon, it’s been a pleasure speaking with you. Thank you so much for being on the show. For our audience, you can find Shannon’s contact information below if you have any questions or want to connect. Shannon, thank you again!

Shannon: Thank you so much for having me.