Understanding Privilege – My Experience in Prison

A month ago Mark Suster (Upfront) and I hosted 75 colleagues for a full day at the California State Prison, Los Angeles County – also known as Lancaster. We did this as part of Defy Ventures, an entrepreneurship, employment, and character development training program for currently and formerly incarcerated men, women, and youth. It was a top 10 peak life experience for me – easily one of the most profound things I’ve experienced to date.

Mark wrote an incredibly detailed post about the experience. Rather than repeat it, I’m going to point you to his post How I Promise You One of the Most Meaningful Days of Your Life. In order to understand this post, you have to start there. So – go read it now – I’ll be here when you get back.

Defy Walk The Line

If you want more views of the day, read Ali Berman’s (Techstars) The Day I spent in Prison, Kerri Shea Beers’ (Techstars) White Privilege, Prison, and a Shot at Redemption, Ben Casnocha’s Visiting Prison Again — With Defy Ventures, Caroline Fairchild’s (Linked) I spent 12 hours in prison with 75 venture capitalists and founders. Here’s what happened, Rick Klau’s (GV) Last month, I went to prison. Next month, I’ll return, Jason Wang’s Going back to prison as the founder of my own startup, Kobie Fuller’s (Upfront) How a day in prison could give you a lesson on judgement, and Kara Nortman’s (Upfront) Spending a day in prison lead me on a path of radical self-improvement. Everyone wrote about the same day (we were all together) if you want to triangulate on the experience.

I’m going to focus on the part of the day where I finally began to understand the notion of privilege. It’s worth starting with one of the definitions from the Merriam-Webster Dictionary:

the advantage that wealthy and powerful people have over other people in a society.”

The exercise lasted about an hour and was just before lunch. We’d had a lot of interaction with the EITs (we are volunteers, they are entrepreneurs in training or EITs) and were feeling as comfortable as one can feel in a level four maximum security prison. Catherine Hoke, the founder and CEO of Defy who ran the event, told us it was time to shift gears. As she described what we were going to do, she told us that it was imperative that we respond honestly. This wasn’t going to be a legalistic exercise, but it was going to be uncomfortable. We then got the rules.

The exercise was called Walk the Line. There were two strips of tape running diagonally across the gymnasium we were in. They were a yard apart. The EITs lined up on one side. The volunteers lined up on the other. We then all took five steps back from the line. As Cat called out questions, if our answer was yes we walked to the line. If our answer was no, we retreated to our position five steps behind the line. We were instructed to look around and connect visually with empathy across the line. We were not to look at the ground or at Cat. We were allowed to shake hands across the line and hug on our side of the line. Cat ended by reminding us that the dominant emotion we should be carrying is empathy.

She then started asking us questions. I’m going to list them all below along with comments in italics on how I felt in response to some of them. I encourage you to read them out loud – it’s the only way you will go slowly enough to really understand what was going on. Each question consumed about a minute as people walked to and back from the line, shook hands, looked at each other, hugged, and cried.

The Warm-up

  1. I like hip-hop.
  2. I work out 3 or more days per week.
  3. I’m older than 20 years old. 25. 30. 40. 50. 60. 70.
  4. I dropped out of high school.
  5. I’ve earned a four-year college degree. Suddenly, I had a feeling about what was to come. Every EIT was away from the line. Almost every volunteer was on the line. This was an almost complete reversal from the previous question.
  6. I’m a natural-born hustler. There were lots of smiles as both sides were generally on the line.
  7. I’ve been self-employed or started my own business, legal or illegal. The smiles continued, with some chuckles interspersed, as a lot of people on both sides were on the line.
  8. I’m committed to starting my own business. 100% of the EITs were now on the line.

About today

  1. This is my first trip to prison. Very few EITs were on the line at this point, meaning many had been in prison before.
  2. I felt at least a little nervous about coming to this event today. 100% of the volunteers were on the line. 100% of the EITs were on the line.
  3. I regularly feel judged by others … for skin color or economic status. The volunteers take a step back, the EITs stay on the line.
  4. I regularly judge others.
  5. I regularly judge myself.
  6. I came here to give of myself.
  7. I came here to take or to receive for myself.
  8. I can already feel myself comparing myself to others, or judging myself or others, right now. 100% of the people on both sides are on the line. Cat reminds us that we are answering honestly and thanks us for doing this.

Even if I don’t know all of you at this line …

  1. I will to do my best to set aside my judgments and comparisons so I can connect with you.
  2. If you become vulnerable in this exercise, I will show you respect and will do my part in creating a safe and reassuring environment for you.
  3. If I see or sense pain or vulnerability, I will offer a hug to reassure you. Both sides of the line are full. I feel anxious all over – I’m sweating and staring ahead across the line, making eye contact in a way that I think is empathetic with the person directly across from me. He looks uncomfortable. I feel uncomfortable.

My childhood

  1. I grew up in poverty. Boom.
  2. My parents paid for braces to straighten out my teeth. All the EITs are off the line.
  3. I heard gunshots in my neighborhood. (wave for “a lot”) All the EITs are on the line. Several volunteers who I know are on the line.
  4. I was suspended or expelled from school. Almost all the EITs are on the line. Several volunteers are on the line.
  5. Violence took place in my home. Again, all the EITs are on the line.
  6. Think of the age when you lost your innocence: I lost my innocence after age 18, 16, 14, 12, 10, 8, 6. As the count down begins the EITs are on the line while the volunteers quickly back off the line. By age 6 there are still a startling number of EITs on the line. I have tears in my eyes as a wave of emotion comes over me. I don’t feel like I lost my innocence until sometime in my early 20s. I can’t imagine self-identifying with losing it younger than age 6.

My Family

  1. For most of my childhood, I was raised with both of my biological parents in the same house.
  2. At least one of my parents wasn’t exactly a positive role model for me – or wasn’t even around.
  3. I was born out of wedlock. I was born to a teenage mother.
  4. At least one of my parents abused drugs or alcohol.
  5. I suffered through the loss of an immediate family member before the age of 18.
  6. My mother or father has been to jail or prison. At this point, the patterns are clear. The EIT directly across me stays on the line through all these questions but the first one. I’ve been off the line since the first one. Now he has tears in his eyes. I keep his gaze while thinking how fortunate I am to have had my childhood and not his.

My beliefs and values before the age of 18

  1. I learned that I couldn’t trust anyone. It continues. Now I have tears again. He smiles at me. He breaks my gaze and looks at the person next to me. I use this moment to look up and down the line on my side. Very few volunteers are on the line. One who I know is on the line and is crying openly. But we continue.
  2. I learned that it’s better to keep my mouth shut and my feelings to myself.
  3. The way I was living, I thought there was a good chance I wouldn’t make it to age 21. There are hugs on our side of the line as we process what is going on. At this point the word privilege isn’t being used (nor does it get used openly throughout the day), but the idea of privilege and how it impacts one’s belief system and values is what is front of mind for me.

Past Criminal life – Cat reminds us that Defy doesn’t work with criminals, but with people who have committed crimes in their past.

  1. I’ve been arrested.
  2. I’ve done criminal things for which I could’ve been arrested, but didn’t. (drunk driving, weed) A series of experiences run through my mind as I think of how different things could be for me if I hadn’t grown up white and middle-class in the suburbs of North Dallas.
  3. I’ve committed a violent offense (even if I wasn’t convicted). Cat stays on this for a while. As all the EITs are on the line, a few volunteers join them. Cat isn’t satisfied and calls out “a bar fight is a violent offense” and a dozen volunteers sheepishly walk to the line. Then a few more do. And we sit with this one for a while.
  4. I’ve been convicted of murder.
  5. I was sentenced before 18 years of age. I’m ready for this experience to end. Between 25% and 50% of the EITs are on the line. All of them are black. Another switch just flipped in my brain.
  6. I’ve spent more than two years of my life in behind bars. 4. 6. 8. 10. 12 (go all the way up). Guys that look like they are in their 30s are hanging on the line through 20 years. We keep going. 30 years. 40 years.
  7. I’m a lifer. Yup – there are a bunch of EITs on the line.
  8. I’ve actually been shot or stabbed.


  1. I’ve lost someone I loved to gang violence.
  2. I’ve lost someone I’ve loved to AIDS. I was one of the few volunteers on the line for this one. I didn’t expect this question at all and it sent me back to my late 20s when my fraternity big brother died of AIDS. I remembered the dream I had on an airplane just before he died but about a week after he called me to say goodbye. I kept looking ahead at the EITs on the line.
  3. I’ve lost one or both of my parents.
  4. I’ve lost a child.
  5. I haven’t properly grieved some of my losses.
  6. I have suffered, or currently suffer, from depression. A lot of volunteers are on the line along with me. I feel a sense of relief that the stigma associated with depression might be lifting, but then I remember the context I’m in.
  7. I could use a hug right now. Everyone walks to both sides of the line. Hugs ensue.

 My children

  1. I’m a father (or mother).
  2. My lifestyle caused me to miss out on valuable years in my child’s life.

If you could see inside my brain …

  1. If you knew every one of my dirty secrets, and knew the real me, you wouldn’t love me.
  2. I feel ashamed of my past.
  3. I feel inadequate, at least in some ways.
  4. Sometimes my feelings of inadequacy lead me to overcompensate in some areas, or act out.
  5. There are some things I haven’t forgiven myself for, and may never forgive myself. A number of volunteers walk to the line, including me. I thinking of a specific thing that has happened to me as an adult. It’s something I don’t talk publicly about because I haven’t yet resolved it myself. Or, more honestly, I haven’t forgiven myself for letting it happen to me. I feel ashamed against the backdrop of everything else.
  6. There are some people I haven’t forgiven for hurting me.
  7. Not forgiving others or myself is hurting me to this day.
  8. I am kind to myself; I do a great job of nurturing myself and taking care of my own needs.

My growth

  1. I’m on a journey of personal transformation. Almost all of the EITs are on the line. People are starting to smile again.
  2. Others look at me as a role model. I’m aware of the importance of my influence.
  3. I might not be able to explain it, but even though I’ve been revealing difficult things and have made myself vulnerable in this exercise, right here, right now, I feel safe, accepted and loved.
  4. I already love Defy!! Everyone on both sides is on the line.

I know that words above doesn’t do the experience justice, but at the end of the hour I was emotionally exhausted. There were at least 25 of the EITs who I had made eye contact with that I wanted to go talk to. There were an equal number of volunteers who I wanted to talk to. Instead, I tried to relax a little. I grabbed on to one word – privilege – that I knew represented a fundamental difference between most of the people on either side of the line.

While it’s easy to talk about privilege it’s hard to really understand it. It’s even harder to experience it if you are the one with privilege. I thought I understood it, but I didn’t. As I let the next five minutes quietly unfold in my mind, I decided that I was no longer going to assume I really understood privilege. Instead, I was going to engage with society in a way to help those without privilege have a better opportunity. Through that, I’d understand it better, have empathy for others who didn’t have privilege, and channel my actions as a human into making the world better from that frame of reference.

I’ve committed to go to prison with Defy four times in 2017. If you want to join me as a volunteer on one of the trips, just reach out. I can promise you a life changing day.

Also published on Medium.

  • Sebastien Latapie

    Thank you for this write-up. What a powerful experience. Just reading through the prompts gave me a much clearer understanding of what is meant by privilege, as well as some strong emotional response. The in person experience must be transformative.

    • i second that. awesome and thanks for posting

  • Manuel A. Richter

    Brad, thanks for sharing your experience and highlighting “privilege”. In our world “privilege” has a huge impact on one’s life from the moment we are born, or maybe already earlier. Most of us tend to forget this and a day in prison definitely helps to highlight this. I am involved in an organisation working with youth inmates. For me it is always very interesting and impacting getting to know their stories and why they ended up in prison. At the same time also learning about their dreams and helping them in making them come true. Nevertheless, for us – you and everybody else, who participates in such programs – we all know that after some hours we will be out and back home. Earlier this year I got a different experience when I got wrongfully arrested and I had to sleep one night in a prison. For me the experience was not the fact of staying there, it was more that from the moment of the arrest, you, your life, everything what you want to do is in the hands of another person. You cannot make decisions by yourself, you need to follow orders. You lose your freedom. There are many things, we, the privileged, take for granted. I encourage everybody, therefore, to participate in such programs as Defy or any other program, which puts you in a situation you are not “used to”. It will open your eyes and mind. I hope nobody else here will have the other experience I had, although it is a much more powerful experience.

  • My wife headed up the medical system for a Delaware State Maximum Security Prison.

    The other two words that are important are compassion and empathy.

    Many of these people have never experienced compassion. None, zero, zip. I told her our (my) lifestyle just could not sustain her having this job. She hung on for more than a year, because she said everyday somebody would cry as she showed them the smallest amount of compassion, by fixing a toenail, a cyst, or something small, that was not medically required that she treat, but she would do anyway. Just a tiny token of compassion, that they never have had.

    Because of this many had no empathy. None.

    She actually believes in orphanages as the least worst alternative. She was abandoned at age 12 and managed to get her Masters from Penn. It was a very tough road. She felt it was her calling to do this because she feels so lucky that people showed her compassion by taking her in, even small things like the janitor that let her sleep in the closet before her rounds after she got off last call as a bartender and rode a motorcycle in the rain or snow to get to the hospital.

    But read Curtis Martin’s Hall of Fame Speech and imagine growing up as him. http://ren-wei.blogspot.com/2012/08/curtis-martin-hall-of-fame-speech.html

    I am probably the most “conservative” person in these comments. I do not believe in hand outs: “free-shit”. I do however strongly believe in mentoring people. Finding a person and just showing some compassion, giving a hand up.

  • Great post. Very powerful to read. Redemption is not conducted in a vacuum. Thank you for putting your personal truths and emotional realities out to the world. Standing on the line and viewing the others would a worthy journey for anyone. s/e

  • Lainey

    Tears right now.

    If women are allowed, I will join you in 2017

    • Women are allowed. About 33% of the volunteers on this trip were women. Email me and I’ll add you to the mailing list for my events next year.

  • While obviously interesting for you, what did they feel and how were they affected? I mean, why did you do this? What do they get out of it?

    • I can tell you from my volunteer work, there are so many adults that have never experienced a positive male role model. They have never received compassion from another man. It’s really hard for both sides to understand. Once you are in the system (prison) it’s really hard to get out. Hell even Walmart won’t hire you. I’m not allowed to hire you (lose my compliance certification)

      I’m going to give a shout out to Charlie Crystle’s Bread company and another one to Dave’s “killer” bread (sold at Costco). They are willing to hire ex-convicts.

      • There’s a fantastic non-profit I just encountered in LA where they take food that is ‘unsighly’ eg bruised vegetables, fruit etc and turn it into wholesome food for shelters etc. The really cool thing is that all the food prep is done by people who have had real problems (homeless, prison, addiction, abuse…) and they are trained as sous-chefs. The program has 100% employment rate on graduation. Now some of the graduates are doing so well in the hospitality industry that they are hiring freshly graduated students.
        “Give someone a fish and you feed him for a day. Teach him to fish and he feeds himself for a lifetime.”

        • That’s a great program. The church across the street from me does a similar thing. I belong to a different one, but I found out about it because I woke up one morning with 100 loafs of bread on my porch. (The bread truck guy got the wrong address) I noticed they all were one day expired. It was funny because I was scratching my head thinking why would somebody put all this bread on my porch in the wee hours of the morning. I went over on a hunch and they were so relieved they thought they couldn’t make their sandwiches for the day to hand out.

      • The only bread I eat (at home) now is Dave’s Killer Bread. In addition to being a powerful story, it’s amazing bread.

        • Jason Randell

          Why not make that bread, the same bread that is broken in the work place? I have no idea what it would take to move the needle for Dave, yet I do know that more individuals that hear this message can then put their thoughts into action.

      • Jason Randell

        Lets create a place where everyone has a shot at being hired. Lets make a culture where positive role models are not only encouraged, they are an integral part of every team…

    • This could be a long post in and of itself.

      @philipsugar:disqus nailed it with his first sentence: “… there are so many adults that have never experienced a positive male role model.”

      It gives you chills (and tears) to hear someone say:

      1. I have never walked across a stage in front of anyone before when they were clapping.

      2. No one has ever encouraged me to do something.

      3. No one has ever said thank you to me.

      4. No one has ever invested a day of their life in me.

      The level of positive energy, positive emotion, and hope in an environment where there is very little of any of those things is profound – at least from my perspective.

      • It is just shocking when somebody tells you that is nicest thing somebody has done for me and my son and you know they mean it. Any you think what???? What did I do???

        You came to my office for learning (I am heading to Lego Robotics League in 10 minutes) and I gave your son some trivial conference swag because he said it was “cool”.

        I’m thinking that doesn’t even register as an act of kindness I’m getting rid of clutter, and you think that is the nicest thing somebody has done?

      • Jason Randell

        After reading this article (for the second time) the only other form of emotional recall I can relate to (as of recent) is when a friend told me “My greatest fear is not living one day longer than my child”. It was in that time that I realized that the prison walls that so many have known to be physical can easily be found in ones own household or mental state. (As I re-read this article and ask that anyone reading this do the same, think about someone you know that has a disability, mental or physical and see if much of what you read could apply to them too?) If you now find yourself pondering the fear of living one day less than your child, you simply have to think of what we are building as a society and what walls should and should not be.

  • Mark’s piece was the best thing he’s ever written. Incredibly moving.
    And yours too.
    I’ll come with you.

  • Mariah Lichtenstern

    LOVE this…Thank you for sharing.

  • It’s posts like this that take your Blog from occasional follow to “must read” status. Thanks for the reminders on ‘privilege’ especially as we enter the holiday season.

    Sounds like a genuinely transformative experience. Good on all of you!

  • Ramiah Spearman

    I often cry n ask GOD why we as an ‘imperfect people’ go thru bad experiences of hardships n pain and/or loss that subsequently causes us to shy away from our true destiny……i guess in trying times all we can do is pray for inner/outer peace, strength n wisdom, joy, faith, serenity n courage and jus pray that we r seen thru n protected n guided by the Good lord GOD Almighty…..when there’s a will there is a way…Lord let our ways be of your will n forgive us as we forgive you first, ourselves n others daily…and deliver us from temptations that try to keep us in constant struggle.

  • What a powerful experience.
    I would love to join next year, sending you an email now.

    • Got it – you are on the email list for upcoming trips!

  • Congrats on being a part of such an important project. Those who are convicted deserve opportunity just as much as the rest of us. I’m a firm believer that whether someone’s a 2nd, 3rd, 4th time offender, everyone should still be given the opportunity to change and turn their lives around.

    I am Canadian and how we look at those who have done or are doing time is different than how most look at convicts here in the US. It starts with listening. I feel that what Defy and you guys are doing is a great step in the right direction by listening to why and how they got to where they are. Then providing them with the opportunity to better themselves and build things.

    Again kudo’s to everyone at Defy Ventures and those involved in this initiative.

  • Powerful post. I’d love to join next year, will send you an email.

    If an EIT is a lifer, how do they implement their business plan?

    • They don’t / can’t but they can still have a powerful experience as an EIT.

  • Rosey

    Brad, thank you for role-modeling a meaningful life. Just… WOW!

    Here I sit on AA1212 MCO to ORD in 6E (1st Class) after leading an all-day client team meeting netting a respectable fee for doing something I was privileged to learn how do, taught by men and women who took and interest me. I am privileged to have ridden on their shoulders. They ran their lives on a proven, highly moral operating system. My privilege is a product of their morals. They did not steal — they would not touch what was not theirs. They did not diminish the life of anyone they met without due process, but added something, and attempted to learn from the least.

    Every step away from the line when one should be able to stand on it, or forbidden to step to the line when one ought to — is the result of a moral failure some how.

    What breaks my heart is these ancient, proven, civilizing moral codes are now mocked and despised.

    I grew up on a world of unlocked doors pick-ups (while varmint rifles hung on back window racks) and an extra plate set at an empty seat at our table in case someone showed up needing a meal (and would never feel unexpected).

    And we were economically dirt-poor.

    Anyway, I’m with you — what privilege I have is the dividends of my parent’s generation’s morality. I am grateful, but i can never apologize for what they crafted. I can only attempt to follow their example — and invest some privilege in those who will receive it.

  • brianrhea

    Truly inspiring, Brad. Thanks for sharing.

  • JaiDee23

    I loved this. The understanding that comes from getting as close to being in someone else’s (someone completely unlikely) shoes. In both directions. The learns, empathy, human-ness that come from it are valuable beyond all. I would so love to be a part of this kind of effort. Thank you for sharing – with tears in my eyes it made my day and I’ll look forward to sharing it.