White Privilege, Prison, and a Shot at Redemption

Last Friday I spent the day in prison. And it was the best day of my life.

About 70 miles north of LA, in the middle of the desert near the city of Lancaster, is a maximum security, level 4 California State Prison. It’s a sprawling facility surrounded by high chain link fences and barbed wire. It’s dirt and concrete and guards with guns. From the outside it looks cold and hard and scary. But on the inside, the most beautiful and powerful human transformation is taking place.

California Department of Correction and REHABILITATION, Lancaster, CA.

Inside the walls of this prison, and 20 more like it across the country, men and women whom the rest of the world have forgotten about, are being given another chance at life. They are learning business skills, taking entrepreneurship classes, and receiving intensive training, coaching and mentorship.

Led by Cat Hoke of Defy Ventures, these prisoners are “transforming their hustle” and learning what it takes to change the trajectory of their lives. They are known as Entrepreneurs in Training, or EITs. Defy is a grantee of the Techstars Foundation, improving diversity in entrepreneurship.

What is most impressive about this program is that those who go through it end up with only a 3% recidivism rate vs. 75% which is more typical. The program gives these men the skills and support they need to make it on the outside so they are much less likely to re-offend.

When we arrived at the prison on Friday morning, we gathered in a classroom along with 30 other volunteers. A bus was en route bringing 50 more volunteers. Together, our entire group was made up mostly of white male venture capitalists, investors and MBAs. Our group included ~10 women and a few people of color, but it was mostly white men in white dress shirts. The EITs had been working on business plans and we were there as judges for a business pitch competition.

We made our way through the security screening and then it was time to meet the EITs. The double doors of the gym opened and we were greeted with loud, thumping music, two long lines of smiling faces, cheering, and lots of tattooed arms and necks. We made our way down the center aisle high-fiving these guys on both sides with each hand. Immediately I was laughing and hollering with them. They were so welcoming and full of joy — you absolutely could not help but be swept up in their positive energy.

The Welcome Wagon

(As this was happening, I realized how it was the same welcome my twin 11 year old boys had received when they started middle school two months ago. At their mostly all-white school in Boulder, Colorado, they were greeted the same way with their all-white teachers in a gym, with loud thumping music and high fives. The contrast was not lost on me.)

A few other people I went to this event with have described their experience. To get the full picture of the day, read Mark Suster’s blog here and Ali Berman’s story here. They do an amazing job of walking through this day and how it affected us on a personal level and what it felt like to be the recipient of such intense empathy.

I’ve had a couple of days for this to sink in — yesterday I spent the day crying and literally telling every single person I met about it. I cried as I told affluent Boulderite parents at our soccer game at Pleasant View fields. I babbled about it to good friends at a birthday party over kickball and beers. I went on and on with my yoga teacher neighbor who indulged me and just let me get it all out.

It is hard to accurately convey what I learned and how this has changed me forever. But I want to hone in on the white privilege part. Before Friday, I had heard that term and scoffed. Yeah, yeah, I thought. I was born with advantages, sure, but come on — people who made bad choices did so of their own accord. Didn’t they? They committed crimes as a result of their poor decisions. Little did I know how wrong I was. I never fully understood all of the factors that led up to these decisions — these fateful moments, these mistakes — that end up changing their lives forever.

One of the EITs from Lancaster

The empathy exercise we did are what made me finally understand what white privilege really means. We did something called Step to the Line. The EITs were lined up shoulder to shoulder in single file on one side. We volunteers were lined up the same facing them, about five feet apart. Our job was to be honest, be vulnerable, and look at the other person in the eye. Offer empathy with your eyes. Cat read off a series of statements. If the statement was true for you, step to the line. If it was not, take a few steps back.

Step to the Line

I like hip hop music. All of the EITs stepped to the line. About half of us did.

I dropped out of high school. All EITs stepped up. All of us stepped back.

I graduated from college. All of us stepped up. All EITs stepped back.

We went through a few of these easy ones until it got harder.

I heard gunshots in my neighborhood growing up. I had a parent in prison. There was violence in my home as a child. I had a parent addicted to drugs or alcohol. I lost a sibling before the age of 10. I’ve lost a child. I’ve spent a night in jail. I’ve been in jail for 10 years, 15 years, 20 years, 25 years. I’ve murdered someone.

The picture starts to become clear. You see what you have in common and you see what separates you. Almost all of the (white) volunteers had college degrees, grew up in safe neighborhoods, with two parent homes. With stability. These men of color did not. The odds were stacked against them.

Most of their stories we heard later were around the pain and anger they had from joining gangs for survival; from committing crimes to get money to feed their families; from being overcome with frustration and rage from the loss in their lives. They do not make excuses for their crimes — they own what they did. But understanding all of the factors that led them there matters. And I began to understand my white privilege.

I’ve done something I should be in jail for.

Almost every volunteer stepped to the line. Look at that. We’ve broken the law too but somehow we are over here. Maybe we didn’t get caught. Maybe the cop let us go. Maybe there were no cops in our safe neighborhood. Maybe no one turned us in. Maybe we were able to pay a lawyer $100,000 to keep us out of jail. Because of our white privilege.

I have done things I am ashamed of. I have not forgiven myself. I have not forgiven someone else who has hurt me.

This is where it all blends together. Some of the EITs and some of the volunteers stepped to the line for these ones. By this time, many of us are crying. Tears are streaming down our faces. We are all one. We felt and realized our humanity — together.

Arsenio was across from me. He was one of the most charismatic guys I met that day. He was always smiling, grooving, nodding his head, moving around, with a Cheshire grin and a calm confidence. When I started to crumble and cry, he stopped moving and looked at me with so much care and just held my gaze. I looked away and came back to him and he was there nodding his head, smiling at me, as if to say — I got you Kerri. It’s all right. You’re all right. There was this unspoken understanding between us and this was going on ALL AROUND ME. When you looked up and down the line you could see this happening between everyone. It was the most intense, human experience of my life.


We’ve all done things we’re ashamed of. It’s hard to forgive yourself. And this is what holds us back in our lives. If this man across from me has forgiven himself for murdering someone, for being in here while his wife has to raise their kids alone, could I forgive myself for the petty things I beat myself up for? For not being the perfect mom? For not being the perfect wife? For working too much, for not working hard enough, for not being home enough? Look at all I’ve been given in my life — my white privilege — two parents, a stable family, a safe neighborhood, a college education, a happy marriage and three healthy children, a great job that I love, money and support whenever I’ve needed it. If these men can make peace with their painful pasts and work so hard for a chance at a new life — then so can I.

And, I will use my white privilege or my megaphone or whatever it takes to tell the world about them.

White privilege is a term that can be controversial. It’s defined as “an invisible package of unearned assets.” I know that it’s tricky for me to go here. It’s hard to talk about race. Who am I to talk about this? To call this out. I know that this can make people uncomfortable and defensive. I only want to highlight this piece of it because it matters. It’s relevant. It was evident as we stepped to the line. I witnessed it. It’s real and it’s a part of a broader systemic racism in our country that is overlooked. We need to wake up and understand what’s happening.

As the day went on we judged their pitches. We went through the most beautiful graduation ceremony. With blue caps and gowns, the EITs processed up to the stage as “Pomp & Circumstance” played and they received certificates from the Baylor MBA program. They had been working so hard for so long and had achieved so much. As they came up on the stage and posed for their pictures, I saw the most powerful and palpable joy and pride I had ever seen in my life. Their smiles were so huge, they were absolutely glowing! I wished that each of their mothers could have been there to witness that. My heart cracked wide open with a powerful love for every single one of them. I realized right in that moment that they were inspiring me to simply be a better human being. To fully embrace and appreciate my life.

Graduation Ceremony

Towards the end of the day, we had a closing ceremony. Each of the men had flowers to give us. JoeVaughan stopped in front of me, holding a flower. We chatted a little bit about the day. It was a quiet, intimate moment. He started to really look at the flower in his hand. I noticed it was as if he had never seen a flower before. He turned it over and over in his hand looking at every inch of it…

“Do you know how long it’s been since I’ve seen a flower?” he said as he stared at it…

“Oh. No. A very long time, huh?” I answered.

“Yeah, it’s been so long…Do you know what kind of flower this is?” he asked.

“Yes, it’s a Carnation,” I said watching him.

“And, do you know what it means, what it symbolizes?” he asked.

I didn’t know what to say. I wasn’t sure, but I looked at him and said the first word that came into my head.

“Kindness,” I told him.

His eyes lit up. “Really? Oh, that’s nice,” he smiled.

We looked at each other in silence. We smiled and just held our eye contact. He said, “Wow, you have so much empathy in your eyes. I can feel it.”

I just nodded and smiled and cried. And said, “Thank You.”

Then, he handed me the flower.

The carnation I received from JoeVaughan.

Cat Hoke and her team at Defy Ventures are on a mission to change the world. To get these programs into every prison in the country. These men are intelligent, beautiful, good people. That is what many of them wanted me to tell you. That one simple thing: they are good people. I saw it in their eyes, in the way they spoke to me, and in the way they loved, supported and respected each other. Yes, they made mistakes and did bad things. But they have been transformed and they deserve a shot at redemption. Just like you and me.

Please take some time to learn more about Defy Ventures. Read the book, “The New Jim Crow.” If you live in California, vote yes on Proposition 57.

Volunteer for a day in prison.

It will change you and it will change your life forever.

EITS who have transformed their hustle.
Jazz hands