I Walked Into Prison With Judgment. I Walked Out With Perspective.

Today I walked into a prison for the first time. I had the opportunity to spend the day at Kewanee Life Skills Re-Entry Center as part of a Defy Ventures program and business competition. I owe the experience to friend and well known Chicago based entrepreneur & CEO, Kristi Zuhlke, who I have known for almost a decade through Junto. Kristi has talked to me about Defy, the work they do and the impact these visits can have, and I can't thank her enough for encouraging me to experience it myself and being there alongside me for my first visit. It was also great to see some familiar faces from the Chicago technology and finance communities who made the trip. I had heard a lot about the experience beforehand, but there really isn't a way to completely prepare yourself for walking into a prison for the first time.

If I'm being completely transparent, I walked into Kewanee with judgment and probably some fear of the unknown. I wondered why the men were there, what they had done, how dangerous some of them might be and what it was actually going to feel like spending an entire day inside a prison. I wondered what the conversations would be like and whether there would be an obvious divide between the volunteers and the incarcerated men participating in the program. You can tell yourself not to judge people, but when you walk through those gates for the first time, some of those thoughts and assumptions are there whether you want them to be or not. Mine certainly were.

What surprised me most was how quickly those thoughts disappeared. Within probably five minutes of meeting the roughly 60 men participating in the day's program and business competition, my mindset began to change. I wasn't thinking very much about why they were incarcerated anymore. I was shaking hands, learning names, listening to conversations and hearing ideas. Instead of wondering what someone had done to get there, I became much more interested in who they were, what they were learning and what they wanted to do with their lives when they eventually left. Judgment started being replaced by curiosity, and throughout the day I found myself increasingly impressed by the wisdom in the room, the professionalism, preparation, manners and genuine desire to learn. There was also a level of graciousness toward all of us who volunteered that I didn't expect. You could genuinely feel how much they appreciated people taking the time to simply show up.

A major part of the day was a business competition, which was naturally something I was excited about. I've spent much of my career around entrepreneurs, businesses, investors and people trying to create something from nothing. I love hearing an idea, asking questions and trying to understand the customer, the problem being solved, the business model and what makes an idea different. As I listened to the presentations, I found myself doing exactly what I would do in any other business competition. I wasn't thinking about incarceration anymore. I was thinking about the businesses. Some ideas needed work, some were surprisingly well thought out, and others led to really interesting conversations. What I appreciated was that these men wanted feedback. They didn't want sympathy or for us to tell them everything was great. They wanted to be challenged, taken seriously and given an opportunity to get better.

There is something powerful about entrepreneurship in that way. An idea doesn't really care about your title, your bank account, your education or your past. You start with something you believe in and then have to figure out what comes next. You have to solve problems, accept criticism, adjust, learn and eventually convince someone else that what you're creating has value. Those are important skills for anyone trying to build a business, but I found myself thinking about how much more meaningful they might be for someone preparing to rebuild a life.

As much as I enjoyed judging the business competition, surprisingly, it wasn't the part of the day that affected me the most. Defy incorporated exercises throughout the program that required vulnerability from everyone in the room, not just the incarcerated participants. That's when something really interesting happened. The normal markers we use to categorize people started becoming irrelevant. Job titles didn't matter very much. Money didn't matter. Professional accomplishments didn't matter. Who had founded a company, managed money, built a career or achieved something impressive outside those walls wasn't particularly important. At the same time, the label "inmate" started to disappear as well.

People began talking about experiences, mistakes, fears, families, regrets, insecurities, hopes and things they wanted to change. The conversations became incredibly human. We spend so much of our lives introducing ourselves through what we do and using titles, careers and accomplishments to establish who we are. CEO, investor, entrepreneur, employee, volunteer, inmate—these labels make it easy to categorize people, but they can also prevent us from actually seeing one another. Defy did an incredible job of stripping some of that away. Once people were willing to become vulnerable, the separation between "us" and "them" became much harder to maintain.

I've thought a lot since leaving Kewanee about the difference between understanding someone and excusing what they have done, because they aren't the same thing. I don't know the stories of all 60 men I met. I don't know every crime, every victim or every circumstance that led someone to prison. Serious actions have serious consequences and accountability matters. Nothing about today's experience changed that belief. What did change was my willingness to think I understood an entire person because I knew one fact about him: he was incarcerated. We do this constantly in life. We take one decision, one failure, one mistake or one period in someone's life and allow it to become the entire definition of that person.

Today made that much harder for me to do. The men I interacted with weren't one-dimensional people defined exclusively by whatever brought them to prison. I met intelligent people, funny people, thoughtful people and ambitious people. I met people with families, business ideas, regrets and real hopes for what might come next. That doesn't erase the past, and it shouldn't. But maybe the past doesn't have to erase everything that could still exist in someone's future either.

Another thing that stayed with me was how appreciative the men were that we were there. At first that felt strange because I didn't think I was doing anything particularly extraordinary. I got in a car, traveled to Kewanee and gave up a day. I listened, asked questions, participated in exercises and judged some business ideas. But sometimes simply showing up matters more than we realize. Showing up tells someone that their idea is worth listening to, that their future is worth discussing and that someone outside those walls is willing to spend time with them without immediately reducing them to the reason they're inside.

What I didn't expect was that they showed up for us too. They listened to our stories, asked questions, encouraged people and participated fully in exercises that required everyone to become vulnerable. It wasn't a one-way exchange where a group of volunteers arrived with all the wisdom and the incarcerated men were simply there to receive it. We learned from one another, and that may have been one of the biggest surprises of the entire day.

I came away incredibly impressed with Defy Ventures. The energy throughout the program was amazing and the execution of a very full schedule was exceptional, but what impressed me most was the culture they created inside that room. There was accountability without constant judgment, structure combined with encouragement, and an unmistakable amount of care and support for people who are trying to prepare themselves for whatever comes next. It also wasn't about making people feel good for a day. The entrepreneurship component required work. Presentations required preparation. Questions required answers. Feedback was real. There was an expectation that participants were capable of learning, improving and being held to a standard. To me, that's much more meaningful than simply offering encouragement. Believing in someone's potential also means expecting something from them.

I walked into Kewanee wondering about the men I was going to meet and walked out thinking much more about myself. How quickly do I judge someone when I don't know their story? How often do I allow a label to tell me everything I think I need to know about another person? How different would some of our conversations be if we removed titles and status and allowed ourselves to be more vulnerable with one another? Those aren't really prison questions. They're human questions.

I've spent a lot of my life around business, entrepreneurship and leadership, and those environments can make status feel incredibly important. Titles matter, companies matter, success matters and money matters. We spend enormous amounts of energy building identities around those things. Then you spend a day in an environment like this and realize how quickly all of it can become irrelevant when two people actually sit across from each other, listen and have a real conversation.

I went to Kewanee believing I was volunteering my time and hopefully giving something to someone else. I left realizing that I probably received as much as I gave, and maybe more. I left with a different perspective on judgment, second chances and the power of vulnerability. I also left thinking about how much wisdom can exist in places we might never think to look for it.

Thank you again, Kristi, for opening this door for me and being there for my first experience. Thank you to everyone from the Chicago community who made the trip, and thank you to Defy Ventures for the energy, execution, expectations and genuine care you brought into that room. Most importantly, thank you to the roughly 60 men who welcomed a group of strangers into their world, shared their ideas and stories, and reminded me how quickly judgment can disappear once you actually take the time to know the person standing in front of you.

I went into Kewanee not really knowing what to expect. I came out knowing two things with certainty: I want to go back, and I want to find a way to become more involved.