Locked In with Ian Bick - Life After 19 Years In Prison | Jesse Crosson Pt. 2
Episode Date: October 26, 2023A “Locked In” repeat offender! We catch up with our first guest, Jesse Crosson. The podcast has grown a lot since our debut episode in January. Find out what Jesse has been up to after serving 19 ...years in state prison as he breaks down 2023 and what he’s got planned for 2024 and beyond. Watch my first interview with Jesse: https://www.youtube.com/watch?v=5M4_oLTtpgY&t=0s Connect with Jesse Crosson: https://jessecrosson.com Buy Merch: https://lockedinbrand.com Use code lockedin at checkout to get 10% off your order Connect with Ian Bick: https://www.ianbick.com 00:00 Intro 01:04 NY Comedy Club Live Show 01:56 One Million on TikTok 03:37 Stimulated by work 04:17 Seeking mental Health Treatment 07:08 Court ordered therapy 10:59 Challenges after getting out of prison 12:30 What it’s like on the bad days 16:00 Having a relationship after prison 18:53 Appreciating things more after prison 20:25 Alex Cooper / Call Her Daddy 22:40 Prison Influencer friendships 24:50 Hurt People Hurt People 27:15 Why is Jesse Crosson interesting? 29:19 Attracting a certain type of person 30:42 Cutting people out of his life 31:46 Non negotiables in relationships 32:48 Are all crimes forgivable? 36:04 His focus now 37:47 Challenges with criminal records 38:47 Felons can’t rent apartments 41:31 Biggest misconception about prison 43:02 Lingering trauma from prison 46:50 Day to day life Produced by: https://www.instagram.com/shanedanahy https://www.shanedanahy.com Learn more about your ad choices. Visit podcastchoices.com/adchoices
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And that's when I realized when I look back, it was the relationships I had that made my success possible.
Somebody offered, give me a free place to stay for six months in town.
So I was no longer living with my mom and dealing with the same dynamics that were problematic when I was a teenager.
I was in town in a tiny, tiny, tiny space.
But who cares? It was like my own space.
Every time I go into a prisoner at jail, I talk to guys.
And I say, look, guys will talk to you about housing issues and getting a job.
What they won't talk to you about is when you're, like, curled in the bed in the fetal position, crying and you have no idea why.
or when you're in a public space and you just start shaking and you have no idea why.
The trauma effects in the body and the social scenes and the environments that set it off,
they were just debilitating.
I didn't know how to deal with that.
On today's episode, we have my good friend Jesse Crosson from the Second Chancer Foundation
back on the show to focus on his life after serving nearly 18 years in a Virginia State prison
and the life he has been able to rebuild for himself.
Jesse was our very first guest ever on this podcast back in January.
and I thought now would be a great time to bring him back into our brand new studio and catch up with him.
Exciting, exciting, exciting, exciting news, everyone.
I will be at the New York Comedy Club in East Village on November 5th,
alongside comedian and podcaster Johnny Mitchell for his live show.
Grab tickets at eInbick.com, and I'm excited to see you there.
Remember by hitting the subscribe button on YouTube or giving us a follow and review on whichever site you listen to this podcast,
It helps us tremendously in being able to produce high quality content on a consistent basis.
Sit back, relax, and get ready to lock in with Jesse Croson.
Jesse Croson, welcome back to Locked in, man.
How are you?
I'm good.
How are you?
I'm good, man.
It's been, what, almost a year now since you came.
You were the first guest in our old studio.
Since then, you passed a million followers on TikTok.
Congratulations.
Thank you.
And we're here.
We got nice, comfy chairs.
a nice trip in for you.
He took the train and had a nice breakfast.
Yeah, and you talk about what I've done.
What you've done is amazing.
You started off with this kind of rag tag idea of,
I want to do a podcast and now having this amazing studio,
having all this production value,
having Chevy Chase on the show.
Like, how did, I don't get it.
I don't understand how that happened.
I know.
It's pretty crazy to think about.
And I always watch, like, our interview
because that just shows how far I've come.
Because it's like that crappy camera angle
on both of us, the echo in the room.
It was two of us, like, I was just asking you questions
that you've been asked so many times before.
And, you know, I brought you back today
to do something a little bit different,
not ask you what you're used to getting asked
about prison and stuff.
I want to focus on the life you've been able to create after prison.
I appreciate that.
It gets repetitive, you know?
I know how I am when I get on an interview with someone.
And I want to do the interview,
and then they're like, give me, tell me everything.
What happens?
and it's open-ended.
It's about the 10,000 time.
You sell the same story.
You're just like, all right, I want something different.
I kind of talked about that at breakfast.
Like, what's next?
What's the chapter after rather than just staying stuck in that personality
or stuck in that experience forever.
So I appreciate it.
The more I've interviewed people, the more I've developed mentally
and more maturely in certain things.
And I think like we were talking about that in the car this morning.
I like to have like in-death conversations and get to know someone
and really have like those intellectual,
talks that you don't always get from telling the prison war stories.
Yeah.
It's funny you talked about it.
You said you're stimulated by your work.
And I think about that.
Like, I want to live a life where the people around me and the work I'm doing is engaging,
like mentally and emotionally.
Like, I want to feel like I'm a part of something.
And it's so easy to get caught in a trap where it's like, I feel like a dog and pony show.
Like, I'm doing the same performance over and over because, yeah, people like it, but it's not
who I want to be.
Absolutely.
So for those of you, for the people listening that don't know your story, definitely check
out Jesse Crosson on all platforms and on our original interview, which isn't the best interview,
fair warning. No fault to Jesse, but at least it does a good job sharing your story.
You served 18 years in prison in a Virginia State prison.
Yeah, almost 19 years.
Almost 19 years. When you got out of prison, did you seek any mental health treatment,
therapy, anything like that? What was that process like for you?
That's a great question. I was one of the people who had sought.
mental health treatment inside. Like, I didn't care what the stigma was, but anybody else says,
I was going to go see mental health. I was a psychologist that I talked to on the phone every week
for 12 years. I was going to try to get all the help I could. And then when I got out, I was so overwhelmed
and I was so busy. I didn't know how to work that in my schedule. And one of the conditions of my
probation or my parole was that I had to get a substance use evaluation and a mental health
evaluation. So I went to see, okay, I have to do this. I called the community service board.
And they were like, yeah, we've got like a three to nine month waiting list. Like, we'll try to get to
you, but we're not really sure.
Went back to probation parole.
They said, well, you have to have it done by this date.
Like, it's not really our problem.
Went back and forth.
And finally, he just paid out of pocket because I was in a position to be able to do that.
Talk to a psychologist and actually got kind of a glowing review.
He was like, hey, whatever you're doing, it's great.
Because I talk to people coming out all the time and, like, your, you know, head and shoulders
above them.
But like, yeah, just make sure you take care of yourself.
And I didn't really, I jumped into this thing.
You know, we were talking about earlier about how we don't know how to relax.
All we do is throw ourselves into work.
And so I was doing that same thing.
and I didn't know how to relax and take care of myself.
And it finally took kind of a breakdown.
Had a conversation with my mentor,
led to some kind of childhood memory stuff
that I experienced in a different way
to realizing, like, I've got a lot of stuff I have to process.
Like, not only from my time in prison,
but from the stuff that led me to prison
and realizing that I needed to deal with that.
And that was when I realized,
I'm going to pay out of pocket for this
because my insurance doesn't cover it,
but it is genuinely the most important thing.
Because if I invest in stock
or if I invest in real estate
or I invest in, you know, relationships,
none of that matters if I'm not taking care of myself.
If I'm not able to show up and be here for myself or be here for the people in my lives,
none of the other work I do really matters because I'm just going to burn out and crumble.
So I've been going to therapy weekly for the past seven months, eight months,
and it was the best decision I made.
What are some things that you learned about yourself in therapy that you didn't know before?
When I've been in therapy off and on since I was a kid.
I mean, because I realized early on that I had issues, but I think in prison I looked so healthy
compared to everybody else and like within that, you know, that small space,
it looked like I was doing really well.
And then so I got out to the world.
One of the things that I learned is that I wasn't prepared for the world.
Like I wasn't prepared for all the challenges.
I wasn't prepared for relationship dynamics.
And I had to kind of grow into accepting that I'm starting over in so many ways.
Because when you get really good at something, you don't want to be a novice all over again.
But now I'm trying to find the kind of joy in that.
And one of the things that I discovered in therapy this round, because I've started doing what's called IFS or internal family systems, is that I've got a lot of like splits and schisms inside of me.
I like to think of myself as, oh, I'm a, you know, responsive.
mature adult. And that's great in some areas, but like when it comes to relationships or when it
comes to those like childhood fears, those insecurities, that's still what it was all those years ago when I
stopped looking at her to dealing with it. You know, it's interesting. I had court ordered
therapy, mental health treatment when I got out and luckily the court system paid for that.
Otherwise, I wouldn't have been able to afford it. But there's like the stigma, especially individuals
like ourselves who are getting out of prison. You have to have like that tough guy act. And that's a
sign a weakness inside prison and outside prison. How do men kind of get over that stigma to be
able to do it? Because I think that once they get over that and they're able to do the therapy and
do the work, they're going to realize there's a relief off their shoulders and that's going to help
them. But it's just a question of getting them to that point. Absolutely. I mean, I think there is this
toxic masculinity and this toxic independence. And I know this is an example. When I first got out and
started making videos, I still responded as if I was in prison. When somebody would make a comment or say
something, I responded with that same like defensive aggressive mindset. And that was one of the biggest
kind of signs for me that, hey, I need to make a change. Like, I need to look at things differently.
Because when somebody is saying something on a video and I'm feeling my heart racing and the blood
pumping through my hands, like this is not how I want to live. And thankfully, I'd reach enough
lows in my life, enough just like absolute rock bottoms that I was willing to ask for help when
nobody else was, when it wasn't cool, when it wasn't tough, when it wasn't, you know, the thing to do.
And in a weird way, that's been the blessing for me. Is it like I've lost everything in enough times
that I don't have any pride around
like not asking for help.
I don't have any pride
around admitting that I'm wounded
or that I have issues.
What I've actually found
and I did find this in prison
which if I lead with that honesty
and that vulnerability,
I actually get a much better response
in any of the tough guy
or slick guy or con man stuff
that people do
because people connect to that.
Like I've had really, real,
deep conversations
with like the most dangerous guy in the room
and almost always response
is like, man, like yeah, I feel that too.
And because I think we all do.
And it's just getting past that idea.
It's not even that like guys
can't be weak in front of other people, they just feel like they can't be weak. The reality is if you
show that vulnerability to the strongest guy or the toughest guy, he's going to respond the same way
because we're all going through the same thing. And so I think it's just getting past that idea
that somebody else is going to judge us and actually going through the experience, being
unafraid to take that first step or taking it afraid and realizing that, hey, we're in a much
better position, more open and honest than we just try to put on an act. You know, that's what I've
always appreciated about you because through your content, you never change up. You don't try to be
someone you're not for views or for likes, like, you'll be yourself. And if it does a thousand views
or if it does a million views, you're still that same person. At the end of the day, you don't let it
persuade you. Like, I think a lot of people in society try to be someone they're not and they're not
comfortable in that. And it's interesting to hear from the perspective of someone that was
not necessarily themselves for 18 years because you were locked in a box for the majority of your
life and to come out and then find who you are and find your purpose and like stick.
to that. That takes a lot. It's a journey. And I think weirdly it started in prison because I mean,
I was that person for most of my life or I guess at this point I'm so old. It's not most of my life
anymore. When I was younger, I was always trying to be what I was supposed to be or what somebody
else thought I should be or what I thought would get me to a position of safety or security or
and finally, like I said, losing everything just allowed me to realize that I can't worry about
what everybody else is thinking, what everybody else expects? Like, what do I need to do to be okay,
to feel like I'm enough.
And what I found inside is contributing to other people,
like finding some meaningful way to interact with the community around me
or somebody in my life or just basically show up for other people.
That allowed me to show up for myself.
And I felt a lot better than when I had money
or I had a position that was based on some outside motivation.
This is who I want to be.
This is what I want to do.
And it is.
There's a validation of getting a million views or a million likes or a million whatever,
but none of that compares to the validation of being able to sit down at the end of the day
and look at myself in the mirror
and feel like, hey, today I was the person I wanted to be.
I did the things that I wanted to do, and I feel good about myself.
I feel in alignment with my values.
I don't always feel that way, but the vast majority of days, I feel that way.
That's great.
What were some challenges getting out after serving that much time and reintegrating into society?
I think they're the kind of classic ones, and I was really lucky because I had a place to go.
And so many people that I talk to don't have housing or don't have any kind of support.
But I had relationships, and that's when I realized when I look back, it was the relationships I had
that made my success possible.
So it was going out and having a place to stay for a month
and then having good enough relationships.
Somebody offered give me a free place to stay for six months in town.
So I was no longer living with my mom
and dealing with the same dynamics that were problematic
when I was a teenager.
I was in town in a tiny, tiny, tiny space,
but who cares?
It was like my own space.
But it was just the emotional components, I think, more than anything.
And every time I go into a prisoner at jail, I talk to guys,
and I say, look, guys will talk to you about
about housing issues and getting a job.
What they won't talk to you about
is when you're, like, curled in the bed in the fetal position,
crying and you have no idea why.
Or when you're in a public space and you just start shaking
and you have no idea why.
The trauma effects in the body and the social scenes
and the environments that set it off,
they were just debilitating.
I didn't know how to deal with that.
And again, I'm really thankful that I was willing
to reach out and ask for help and talk to people about that.
Because I talked to people, there was a guy who called me the other day.
He's been out for three and a half years
and he still doesn't talk to anybody about that
until he gets drunk in the middle of the night and calls me up.
And he's like, bro, I just don't know if I can do it.
Like, hey, if six months in,
you would start talking to somebody
and seek and help for this.
You wouldn't have to hide it until the middle of the night.
You wouldn't have to keep pushing it down until it becomes so big.
It just explodes and you can't control it.
I think we all struggle with the emotional stuff.
We all struggle with the environments that just feel so alien and so dangerous,
even though there's no threat there anymore.
So I want to focus on that for a second.
You and I both have large social media platforms.
And our followers, our listeners, our viewers don't necessarily see us in our sad moments
in our moments where, you know, we're a person.
We're having a bad day.
You know, we're in bed, we're crying, we don't feel like going on.
What are those moments like for you that the world doesn't normally see and how do you get through those moments?
When I try to be as transparent as possible, because I think that there's this horrible culture on social media of making everything look good and glorious and perfect and I just think that's BS and it's incredibly destructive.
So I've cried in a number of my videos.
There's one that it's kind of funny now, but literally I was sitting there.
somebody had sent me a giant box of potato chips and I was sitting there eating them with chopsticks
and Courtney recorded me she was like are you okay I was like no like I'm just having one of those
days like I just I got to eat a whole box potato chips with with chopsticks and I think it's important
to highlight that but of course when I'm going through something really difficult yeah I'm not thinking
about a camera I'm not thinking about responding to the world like I'm just trying to hang on so I would say
for me those moments are generally when I'm comparing myself to something in the world and I don't
feel like I'm adding up or some of that kind of like childhood trauma or
some of that internal stuff is just welling up in a way
that I don't know how to deal with.
And I'm really grateful that I've developed
a lot of coping mechanisms I didn't have.
I've learned things from DBT,
I've learned to reach out to friends,
I've learned to kind of come back to my body,
I've learned things that have helped me get through that.
But the other side is when those things come up,
like I call them emotional storms,
which I actually got from a relationship
with a girl who is very emotionally unhealthy.
When they come up, I just have to allow that to be.
Like I found the most vital and the most important thing
is to allow that to happen
and not push it away or not act like it's not important.
I'll cancel a meeting if I'm in a place where I just know I'm struggling because I'm not going to show up half-ass to this meeting and not like actually give myself to the person and give them the attention they deserve and I'll lay there and there are times that I just have to literally like just kind of put myself under a blanket and cry or struggle and they're happening less and less over the years but it's only been two years.
Like I'm trying to give myself some grace to accept that, hey, I haven't like built great wealth or I haven't changed the world completely or I haven't like stopped crying under a blanket, but it's only been two years.
Like maybe years down the road it'll be okay, but give myself a little bit of room.
to feel those things and just be human
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Makes me feel a little bit better.
And I think it's important for the average person to see that someone with, like, say, a million followers on TikTok is still under their bed sheets crying sometimes because things are hard. Things are tough. Like, that's a part of life. You have to go through that. And it's normal to feel pain and feel hurt sometimes. And I think that's a big problem with social media that you have a lot of influencers and stuff portraying the certain life and it alienates people thinking that that's a whole different.
world, but they feel what you feel too.
100%. I mean, that's
one of the things I never learned growing up. And like, if I look
back, I wish somebody had taught me that
it's okay to not be okay, that things are
going to be hard, that they're going to be days where you just
don't perform at 100%, you don't perform it 20%.
You just barely get through the day.
And that that's okay. Because for my whole
life, I always thought I was supposed to be up here all
the time and I wasn't. Not only did I feel bad
just because I was feeling bad, then I added that layer
of like shame or guilt or self
recrimination. Whereas if
I had just allowed it to happen, it would have kind of like
passed on by, but I clung onto it, and that led me into the depths of addiction, that led
me into the depths of destruction, it led to me into the depths of depression I didn't know
how to climb out of, rather than just accepting that, hey, some days are going to be good,
some days are going to be bad, but, like, it's a flow, and if I just keep riding, I'm going
to be okay.
Now, when you got out, you kind of simultaneously built your social media platform to showcase
your journey, and you had a relationship coming out of prison.
What was it like to go through, like, a public breakup with your followers, where you guys
broke up and your followers felt how you were feeling?
because I remember seeing your videos
and I felt your pain as a follower.
What do you think that connection is like
and how do you feel about that?
That was really strange
because I never know how much of my life
to keep private or public.
And there are some people I know
who have massive followings
who have personal lives
that nobody knows about it.
If you don't know them as a friend,
you don't know what's going on.
I think it's important,
if I'm going to put myself out there
to be like you said,
honest about the good things
and the bad things,
the struggles as well as the joys.
And so I thought it was important
to share that.
but I didn't know how to share that.
So I remember we had broken up.
We had this rough night.
And then I didn't say anything about it.
And I'm still trying to make videos and like, dude, I didn't want to get out of bed.
I was struggling.
But finally I was like, all right, like, I have to do this.
Because somebody noticed like, hey, we haven't seen Courtney in a couple videos.
Like, you haven't seen okay.
Like, what's going on?
And it felt good to be able to share that and not feel like I was holding onto a secret.
But it also felt bad because the, like, the internet divided over me and my ex.
Literally, I had people who were like Team Jesse and Team Courtney.
And I'm like, hey, I'm Team Courtney.
Like, this is not a schism.
There was a Reddit sub thread about me that a bunch of people sent me over, like,
whatever you do, don't read this.
I was like, man, when does this become my life that, like, I'm literally being, like,
attacked by people on this side and I'm having people reach out to me and my DMs as soon as
we break up, like, hey, by the way, like, now that you're single, it was just, it was so
overwhelming and bizarre and beyond anything I could have imagined that I'm glad that I did it
publicly.
And I, my focus was really to do it with integrity, to, like, carry myself in the way, both
publicly and privately that I could feel proud of,
if I'd feel comfortable with.
But it was definitely overwhelming in a way that I didn't expect.
Looking back on it now, even though it was devastating at the time,
do you think you needed to go through that
and experience that alone, single time?
I mean, I think I still do.
And it's funny because Courtney and I have talked,
we go through periods of, like, being closer and not,
but, like, we both really care about each other.
And we always will.
And she's come to me and said,
look, you know, I realize now it just wasn't realistic
to expect you to jump into a relationship.
Like, you need your time.
And the problem I have now is that,
Once I was single, I was like, cool, I'm single.
I've been thinking about being single my whole life.
And rather than taking that time to actually take care of myself, which was my intention,
end up going out with friends or going on dates or being busy and not really taking
that time to figure out who I am in the world.
So that's something I'm still struggling with and still trying to figure out.
Because it's just like we want to make up for lost time.
We've talked about like, hey, we want to catch up.
We want to get ahead.
Well, I can't catch up and get ahead with a relationship until I'm ready.
So if I jump into another relationship, all I'm going to do is end up in the same place.
I need to take that time to kind of build the framework for myself.
really focus on who I want to be and how I want to live my life.
And then I can work on building another person into it.
But if I do it now, I'm just going to get lost in another kind of maze and not actually move forward.
What are some things that you've come to appreciate more now post-prison that maybe you didn't appreciate before you went to prison or even while you were in prison?
Well, it's easier to say the things that I appreciated more now than before because it's everything.
I took everything for granted before I went to prison.
And in prison, I don't think I took anything for granted because there was a lot of,
a scarcity or a rarity to even moments outside or fresh air or breeze or seeing the stars or anything
like that. And I try not to lose that. It's one of the things I try to hold on to it. And I'll
try to put it in perspective because I'll always end up with one of these like first world problem
situations. Like I'll notice I'm getting frustrated over traffic or I'm getting frustrated over
whatever, some minor detail in my life. And then I go back and I'm like, you know what? Like two years
ago, I would have been ecstatic to be stuck in traffic. I could not imagine how joyous I'd be to be
stuck in traffic.
That being said, I get to enjoy things that I never expected.
I'm up in New York with Morgan, and she's making me go shopping and buy different clothes,
and she's right because she says, people will judge you based on the way you dressed.
And for the longest time, I was like, I'm not going to do that.
But look, it's kind of nice to get a nice outfit and go out and see people respond to you
in a different way.
It's nice to eat good food.
Like, it doesn't have to be expensive, fancy sit-down food.
Like, there's a taco truck in my town that's amazing.
But making that a priority to say, you know what, rather than sitting at home and eating microwave food
or rotissory chicken from Costco, I'm going to good.
go get good food.
And especially if I can do that with other people,
because I need more of this time by myself,
but what I love more than anything is like finding my tribe or my community.
And there are people at the co-working space I go to.
There are people at the gym that I enjoy spending time with.
And every time I go, I leave feeling like my cup is full.
Whereas when I go around people I don't want to be around,
I leave feeling exhausted and depleted.
Yeah, you know, I was listening to Alex Cooper from Caller Daddy,
big Caller Daddy fan.
And she was saying she was like,
one day she found herself sitting in her house,
like on her phone scrolling through TikTok
she's like have a beautiful
fucking sunset outside why
why the hell am I sitting on my phone right now
scrolling through TikTok
and sometimes we get engulfed in that
like I'll before bed I'll go on TikTok
and like all this motive my whole algorithm
is motivational inspirational
type stuff which you know I love that
but I go down this rabbit hole
and you know when I should be sleeping or I should be
doing other things that I'm really trying to prioritize
that and like we were talking about earlier
I love diving in to work, because that's the only thing I know how to do, because that's what I did my whole life.
You know, when I had the club, I lived, ate, slept, breathe the club when I, you know, got out of prison.
I was at Whole Foods.
I did every, I was there, you know, 100 hours a week.
And now I'm doing this.
So sometimes we just have to, like, appreciate those moments and there's a power in that.
And that's, you know, people in my life are really good about that where I'll be spending time with somebody.
And they'd be like, bro, put your phone down.
Like, what are you doing?
and I try to do that myself.
Like, one of the reasons I moved,
Courtney and I bought a house outside in the country,
but we didn't like it,
and I think that actually contributed to our breakup
because I don't want to drive 30 minutes in and 30 minutes out.
Because every morning I get up,
two days a week I go to the jiu-ditsu gym,
three days a week I go to the gym at the apartment complex,
and then I go walk downtown.
I walk to the co-working space.
And that's time that I'm not on my phone,
although sometimes I make videos doing it.
But it's like time for me to be out and in my body
and not in the busy craziness of it,
like appreciating the fact that it's beautiful
or that it's cold or that's raining,
because I bring an umbrella,
but like putting myself out in the world,
because for all those years,
that's what I wanted to do.
And instead of sitting inside,
scrolling on my phone and working from home,
I'm gonna go out and be around people.
And I do, I find that incredibly rewarding.
And I've developed friendships that when I had my motorcycle accident,
the manager from a co-working space
came and stayed the night with me.
Like, people from there brought me food.
People from the gym bought me like an Uber Eats account.
Like people just looked out for me
and it was just, it was so touching,
and it was so validating.
And it really let me know
that the most important thing in my life
is not the accomplishments or the money
or the positions, it's the people.
It's the relationships.
And that's really where I want to focus my energy.
Absolutely.
And on the topic of friendships, a lot of our followers, listeners, viewers,
when they see individuals like me and you together on TikTok or other people in, like,
the prison talk community, they always get excited for like those crossovers.
Can you talk about how that formed, like what exactly are like these prison talk retreats
and how it's like a community in itself?
Sure.
So I had somebody reach out to me on social media.
I guess a little more than a year ago,
and say, hey, you know, you really need to get a community.
You need to find your people.
You need to come together.
You guys talk all the time.
Why don't you invite them?
I've got this property up in Pennsylvania.
Why don't you guys all come out here?
And nobody had done that before, not that I know of.
So it seemed like a crazy idea.
So I reached out, and I reached out to Carrie and Morgan and Marcy and all these people
and said, hey, this is going to sound crazy.
But do you guys want to meet me in a rural Pennsylvania that may be a murder house, but hopefully not?
And everybody did it.
And everybody showed up.
And we had an amazing time.
Vice News came and did an interview with us, and we found that there was just like incredible emotional experience.
Like we talked about things that were not for the cameras, that were not for anybody else, that we were able to talk about that because we'd been through a similar experience that a lot of people don't understand.
And we also realized that people were interested and went crazy over the crossovers.
So we made a commitment to do this, like once a year or a couple times a year.
And we've done it, I think, three times since.
And it's been incredibly validating to get together.
And we, I think we had one we were planning for this year that it just kind of fell apart.
but we're going to continue to do this because it's the opportunity to come together.
And sure, like, people get excited and we get to interact and we really like each other.
But additionally, like, there's something healthy about that.
One of my board members from the nonprofit is formally incarcerated.
But as soon as he got out, he stopped associating with anybody from that life.
He went to college.
He got a Fortune 500 job.
And he forgot until we were sitting in the room together talking about things.
He's like, man, I forgot how good it feels to be around people who I don't have to hide anything from, who I feel comfortable with, who know what I have to say or what I'm feeling before I ever have to express it.
And I think there's a value in that.
but the only caveat is that they have to be people
who've been through the same experience
but are also doing the same things now
like living a healthy life
and that's not always the case
and that's why I stay away from a lot of people
who have had the same experience
but are still like reveling in the craziness
of it or still telling war stories
because that's not where I want to be.
I want to be like how do I build the next chapter
of my life knowing that this is where I came from
and these are the advantages
and disadvantages I have from that experience.
Do you think that quote about hurt people,
hurt people and healed people,
heal people applies to this scenario?
Very much so.
I mean, I think hurt people, hurt people, and hurt people can also heal people.
But it's a question of, are we investing in our own healing?
Are we investing in dealing with the things that we've struggled with or that have hurt us?
Because until we do that, we can't help anybody.
Or if we do, we're trying and we're just depleting ourselves and exhausting ourselves, the point that we collapse.
But yeah, very much, like, we have two choices in that situation.
If we've experienced trauma in our lives, we can either use that to kind of, like, hurt other people and pass that pain on as an infection.
We can use that to heal ourselves and try to heal other people.
Something I found fascinating when I was in Houston and I got to meet a lot of the other prison
TikTokers, whatever, you know, we call ourselves. But I just, I saw a room of individuals that went
through some very traumatic experience in their lives and they're turning that into energy.
That's like their purpose and creativeness and what they're doing. And within that comes a lot of
happiness and fun. Like I see when you and Morgan were posting videos on TikTok last
You guys are just like, you guys have so much individual trauma, but you're coming together and you're happy and you're sharing that with the world and the world just needs more of that.
I mean, and that's, you know, spending time with everybody from that group and I've spent more time with Morgan lately.
This is actually an interesting example because one of the reasons I'm back here is because I came to spend time with Morgan last time.
I ended up running around and spending time with friends and going to meet other people.
And she said, hey, like, if you made a commitment to spend time with your friend, you need to spend time with your friend.
And I needed that.
I want friends who call me on my stuff,
who don't just allow me to do whatever.
And that's why I was like, okay,
if I'm saying I'm prioritizing relationships,
I need a prioritized relationship.
This whole trip, including being here with you,
I prioritized, all right,
she's got to work from this hour to this hour.
I'm going to go meet people.
I'm going to go meet foundations.
I'm going to try to raise money.
And then on the off hours,
I'm spending time with her.
We're going to go out to dinner.
We're going to do stuff together.
We're going to enjoy each other as friends.
And that's what it is.
When I make that time and I commit to it,
we make funny videos and we laugh and we go clothes shopping.
We have good food.
and it's a valuable experience rather than the mindset of,
another way we talk about throwing ourselves into work.
We never get out of this compulsive place.
We're like, all right, what's the next connection we can make?
What's the next money we can raise?
What's the next project we can work on?
What's the next video we can make?
Like, no, like let's just sit down and actually enjoy each other's company.
What do you think draws people to you?
Why do you think that you're an interesting figure in certain people's minds?
Have you ever thought about that?
What the draw is?
I think I'll say what the majority of the comments that I get say that my communication style or I communicate very clearly or that I speak well.
And I think that draws people into some degree.
But more importantly, and what I hope it is and what I've had people tell me is it's authentic and vulnerability.
Because the people that I want to be around are the people that are real.
I don't want to be around somebody who's a tough guy.
I don't want to be around somebody who's pretending to be something they're not.
I want to be around somebody who's smart or dumb or pretty or ugly, like whatever quality they have, they are who they are who they are.
And weirdly, I learned that in prison
because I remember there's this
little gay, like, kind of tough guy.
And I remember thinking, like, how can you be little and gay
in prison? Like, you're going to get picked on, you're going to be whatever.
But he was just who he was. And he actually, he could fight.
He was kind of a dangerous guy. But it was one of those things where
it was this inspiration where in this place where I thought you had to be a certain
thing, he was just 100% himself. He wasn't ashamed of it.
He didn't hide it. And I was like, man, that's what I want to do.
I want to be myself. And so I spent those 19 years
working on trying to figure out who I was and just be myself.
And those moments of transition of, you know, standing up to Samadie and saying, hey, I don't like your homophobic stuff, or I don't like this, or I don't like your misogyny, or I don't like that.
Being who I was in the face of what felt really uncomfortable was incredibly scary in the beginning, but then eventually it became a strength because more often than not, just like I said, when I lead with vulnerability, I get a positive response.
And I remember having conversation with guys, sitting in the cell with guys, who everybody, you know, was afraid to talk to or thought was, you know, was somebody else, and having these conversations about their experience in foster care or having been sexually assaulted as a kid or the things they'd gone through.
and realizing that, hey, everybody's looking at this guy as a monster.
Like, dude, he's just struggling like everybody else.
But I wouldn't have gotten there if I hadn't been willing to open up about my own experiences,
my own struggles, or put myself out there and make myself available.
So hopefully that's what it is.
Hopefully it's just the fact that I put myself out there, you know, authentically and
vulnerably, and that I make myself available to other people because I genuinely care.
I'm interested in people.
Do you think you attract a certain type of person with that mindset, friends, relationship,
anyone that comes around your circle?
Do you think that attracts a certain type of individual?
I'll say when I look at the people in my life, the people that I spend time with, whether
it's at the co-working space or the gym or people online, I seem to have found people who
have a similar value.
Maybe we're different places in the journey.
There are people that I meet that I look up to because of the things they've accomplished
or how strong or how vulnerable they are.
And I meet people who are just starting on the journey.
I just got an email this morning from somebody who said, hey, this is what I'm struggling
with.
I have no idea how to move forward and I don't know who to talk to.
Like, are you willing to talk to me?
And I get a lot of those messages.
And I guess that's what I'm hoping.
Like, if I can help people by being open and authentic, and I can be helped by people who are being open and authentic, I hope that we can kind of form this, like, network and this community of people who are just living their best life.
And the thing about it is that's one of the reasons that I love the gym and I love the co-working space.
Because the manager at the co-working space who came to stay with me has a PhD in history, which is a professor and then left to run a co-working space.
At the gym, we've got like a venture capitalist and a police officer and like a dude who's basically just smoking weed for a living.
And everybody comes together.
And it's not about what we do in the world.
It's just about how authentically and genuinely we live our lives.
And that's the connection.
Because I don't want people who just do what I do or just are interested in what I'm interested.
I want to expand my horizons.
And I get that through people who are just genuine and open and authentic.
And it's one of the things that inspires me.
Have you had to cut certain people out of your life that were with you when you got out of prison?
But now that as you've grown and developed as a person, they don't fit in that mold anymore.
100%.
The way I put it is, you know, there are people that I still love, but I have to love at a distance.
there's some like very personal some family members that I've had to push away not even necessarily because of anything currently but because I realize that there are dynamics there especially dynamics from childhood that that they don't serve me well like I'm not the person I want to be when those dynamics come up so until I can heal myself enough to the point I have to keep them at a distance and that's that's really uncomfortable and I have a lot of guilt around that and I struggle with that what I come back to is the only way that I can be whole is again to like focus on healing myself to then be in a position to deal with people who maybe things come up or I feel triggered by or I feel triggered by or I
struggle with. But, you know, I've talked about this in prison. It's been true, probably even
more true since I got out. It wasn't just about finding good people in my life. It was about distancing
from the people who are drawing me down. Like, who is adding value and depth and genuineness and
love to my life? And who is somehow depleting me. And the people that are depleting me,
again, I just have to love them at a distance. What are like three non-negotiables you won't
accept? Gaslighting. Gaslighting is number one, because I've been through that so many times.
for somebody who's close to me
somebody who is like engaged in compulsive destructive behavior
that is like drawing them down or is bringing the law
or bringing you know danger on themselves
again I can love them at a distance but I can't be around that
and I think that the last one would just be like
patent dishonesty and I notice a lot of people
who are unable to be honest with themselves
and I don't begrudge them I'm not angry at them
when I see someone who can't be honest with themselves
or who can't be honest with the people around them
I'll tell them and I'll tell them with love like hey
you know when you get this figured out like I'm happy to be
be here. I'm happy to meet you, but I can't expend my energy on somebody who's not willing to be
honest with me or not willing to be honest with themselves. And I'll help you get treatment. I'll
help you get resources. Like, what do we need to do to help you? But I can't spend my energy on that.
Now, your platform, you've built a platform that's entirely on second chances. That's what you
believe in. Your foundation's called Second Chance or Foundation. Do you think that there are
certain maybe crimes or things that people commit in their life?
or do in their life that a second chance isn't warranted,
or do you think all people are deserving of a second chance?
I think that depends on how we label a second chance.
There are people, for example, that I understand why we don't ever let out of prison.
I would not feel comfortable living next to them,
and I wouldn't expect somebody else to.
That being said, if that person is going to be in prison for the rest of their life,
is there a way that they can add value to their community?
And maybe there's not.
Maybe some people are so traumatized and so damaged that they have no value to add,
there's no way that they can contribute.
But if there is, if they're behind the walls,
why not put them in a position to do that?
Why not allow them to mentor other people?
Why not allow them to train or teach
or work online or do something?
And when people get out,
there's this massive community
that judges people by their crime when they get out.
The way I look at it, if somebody is getting out of prison,
our number one priority as a society
is to make sure they have the tools they need
to get on their feet and exist
without returning to crime
or without going back to a dark place.
And when we say, oh, well,
we want to give housing to this person
but not that person.
or we'll support nonviolent criminals
but not violent criminals.
All we're doing is we're just creating
a separate subset of people
that were just pushing back into the corners
and pushing back into the old life that they had.
And so I believe that if somebody's getting out of prison,
we need to make sure that they have at least the opportunity.
Not everybody's going to take advantage of that opportunity,
but the people that never have that opportunity,
they're out on the streets with 40 bucks and no hope.
I don't care what they did to go in.
I don't want to see them doing that
because it's more likely that they'll hurt somebody else
and go back to prison because that'll seem like a better option
because they don't have an option out here.
So second chances don't necessarily have to mean the person got out of prison.
Society needs to give them a second chance.
Second chances could be as simple as an inmate being or given the opportunity to teach a class in prison or to maybe go to the gym or do things like that in prison for themselves.
It could be internally too.
Sure.
I mean, I definitely believe in a different sentencing structure than we have.
I think we have a lot of prison, people in prison for the rest of their lives that don't need to be there.
I'd give you an example.
I have a friend sincere who managed to get a group of elected officials to come into the prison.
And the prison system was terrified because they're like, oh, my God, what are they going to say?
What are they going to talk about?
What are they going to do?
But they had organized this well.
Because rather than showing up and talking about the abuses or the scandals or things that were going on,
every one of them showed up with a program they had written or a class they had taught or something positive they've done or a book that they had published.
And all the elected officials were like, why are these people in prison?
Like, this guy's been in prison for 30 years for something he did when he was 17.
He wrote two books and designed a curriculum that's used by the entire DOC.
Like, why is he in here?
Like, yeah, he did something terrible.
Why are we paying $30,000 a year every year to have him in here when he could be out there working with the kids that most need, you know, an example of change?
Working with somebody contributing to his community paying taxes.
And so I think that, yeah, we need a different sentencing structure.
But that being said, there are probably some things that society is never going to accept.
and I understand that.
And I found meaningful work while I was inside,
mentoring people and tutoring people.
I felt probably a more meaningful existence
doing that inside than I ever had outside on the street.
And if I had done something absolutely heinous and unforgivable,
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I would at least want that opportunity to contribute and be a part of some kind of solution where I've been a part of the problem.
What's your focus on now, the re-entry aspect or the actual reform inside the prison itself or maybe even before it gets to prison and just like the sentencing structure and how that process plays out too?
So what we do with the nonprofit is separate from any advocacy work because there are regulations around how that's how that's done as a 501c3 versus four.
My focus with the nonprofit is we're focusing on essentially reentry services.
Trying to make sure that people have connections.
And again, going back to relationships, the most important thing in my life, both when I turn my life around in prison and since getting out has been the relationships that I've had.
So we're building a digital mentor network to where we're connecting people with professional experience from all these companies that say, hey, we'd love to give you five hours a month.
We've got 10,000 employees.
It's 50,000 hours a month.
Like, we have a lot of resources and a lot of people with experience they can share,
as well as the vast array of formerly incarcerated people who can coach people through the process of reentry.
And so we're going to connect them both by kind of a digital mailbox and eventually through apps like Emilio to people.
To people who are currently incarcerated as formerly incarcerated can develop relationships with people
that will help them navigate the process of reentry, help them build professional skills,
help them learn about a space they want to get into, and just expose them to what's out there.
I didn't know what venture capital was.
I didn't know what entrepreneurship was.
I didn't know anything about tech.
I didn't know anything about these things
until I had a relationship that introduced me to him,
which led to more relationships.
That being said, on the advocacy side,
there are a lot of things we're doing.
Like right now we're doing a big push
to try to reduce the cost
or eliminate the cost of phone calls and video visits.
Because, again, relationships are the most important thing.
And if people can't afford to stay in touch
with their loved ones, they can't afford
to stay in touch with the positive forces on the outside,
they're going to continue to communicate
with the negative forces on the inside.
Have there been challenges
with your criminal record,
running a foundation?
So with the nonprofit, there hasn't been a challenge.
But I give you an example.
When Courtney and I bought the house outside of town, never once did they run my background,
did they check my name, did they do anything?
No issue there.
But when we broke up and I started renting that place and I tried to rent a place in town,
I got one denial after another.
Oh, you're a convicted felon.
You need not apply.
Oh, you have a criminal record.
Sorry, we can't accept your application.
So I could buy a house, but I couldn't rent an apartment.
Like, this just didn't make sense to me.
And weirdly, there's been a lot of growth in the kind of
service space to where people are looking for someone who's formerly incarcerated. And sometimes
that's really good because they say, hey, you've got the experience you can help, but sometimes it
turns into this really performative dog and pony show where they want to trot somebody out and say,
hey, we work with formerly incarcerated people. Look at this guy. Look at how good he is. And then they send
them around to do this show while the nonprofit doesn't actually do any work. And that's the thing
that infuriates me the most because they're devaluing people in the same way that the prison
system does, but they're feeling good about it and trying to make other people feel good about it.
And that just feels so dishonest.
Where do you think that stigma comes from that a felon can't rent from certain housing?
Like, who do you think came up with this?
And then why do you think that's in place?
Is it the neighbors not wanting to live next to someone with the criminal history?
Is it the owners of the building themselves that are worried about it?
What do you think that comes from?
So actually, I reached out and talked to a bunch of different people because I was thinking about trying to take this on as an advocacy piece.
One person who worked for a giant property management company said was that we simply look at the statistics and we have worked.
statistics people are formally incarcerated than we don't. That's the reason why we do it.
We don't care. We don't care what your history is. When we look at the numbers, it doesn't make
sense to rent to people. And I started thinking about that. I was like, well, you know, if I came from
a place or I'm in prison and I don't take care of myself or I'm taught that I don't have value or my
environment doesn't have value, it would make sense that I would then go out and not take very good
care of my apartment or take very good care of my place. So I think there are programs that
would help show people, like essentially a better way to live and a better way to take care of themselves
and take care of their environment. But there's also legislation. For a long time, if you
had a drug crime. You couldn't live in Section 8 housing. You were banned from housing all of
the state of Virginia where I live. And what that did was essentially force people to be homeless
rather than living in a sustainable place in the name of public safety because then they couldn't be
in those neighborhoods selling drugs. But that didn't stop them from selling drugs. Like it didn't,
if anything, it pushed them in a corner where they couldn't get a legitimate job because they didn't
have a place to live. Like they're forced to be on the corner and force to live in hotels and
forced to scramble and get by. And so I think that it was all intended as a way of protecting
public safety, but the end result was actually significantly harming public safety.
You know, there's plenty of people that don't even go to jail that can't pay their rent.
They're no different than someone that's getting out of jail and that's looking for a chance and is denied that opportunity.
So I feel like that's kind of just like a blanketed excuse.
Like it's kind of a skewed number to say, oh, we have more bad history with people that happen to have a criminal record.
Yeah.
I don't know.
It's crazy to me in that sense.
It's one of those ones where I see that if we invest in people, we get a return.
And that's one of the number one things.
That's why we're so interested in the mentor network because I look at, you know, Josh, one of my board members, who got out, the one who went to the Ivy League school, who did all the good things.
When he got out, the only job he could get was at a hardware store because Hardy's turned him down, McDonald's turned him down.
Everybody turned him down.
And he probably would have stayed working at that hardware store until somebody invested in him.
Or we've got a guy up at Columbia right down the street from us who was out working at a tire shop.
And because they were the only ones who gave him a job, he almost turned down the opportunity to go to Columbia University because he was like, no, they were good to me.
like they gave me a chance.
The loyalty you get out of somebody
when you invest in them
when nobody else has is incomparable.
So if you're willing to take that person
and give them a chance,
connect them with a job,
allow them to be the handyman
for the place while they live there.
Like you're going to get loyalty
in a way you're not going to get
from anybody else on the street.
What do you think is the biggest misconception
about prison
that society doesn't understand
or hasn't realized?
I think it depends.
I think we have half of our
half of our country
is for rehabilitation
and half our country is for punishment.
And I think that the people who are all about punishment,
they misunderstand that prison is full of hurt people.
Like, that's just the reality.
People don't do the things that they do to go to prison
because they're happy and healthy and living a good life.
They do it because they're traumatized.
They don't have coping mechanisms.
And they're doing the only way they know how to do.
For the other people, I think that there's an accountability issue
where a lot of times I'll talk to people who are very much in the advocacy space and
we just need to let everybody out.
And if we just give them a job, it'll be okay.
And it's like, no, like, that's not actually true.
We do need to give people jobs, but we need to work on accountability.
We need to help people take responsibility for their actions in a way that they may not have
realized that they were failing to do in the first place.
And when people just say, oh, you know, if we just like give them something, it's going to change,
it's like, no, there's a lot of trauma.
There needs to be work on that trauma.
There needs to be therapy.
There needs to be healing.
And we need things like the victim impact program, which is based on restorative justice,
which is about, hey, you need to take responsibility for the things you've done.
Like, you were not in the right mind state to do that.
Like, I wasn't in the right mind state when I was strung out on drugs and I was dealing with
childhood trauma and trying to figure out what I was doing, but I still had to stop and take
responsibility for what I'd done. So I think on each extreme is this unfair and unrealistic view
that people are either evil or people are kind of saintly. And in the reality, we're all just
flawed people. We're all just hurt people who need some kind of help and have to be accountable for
the things we've done so that we can move forward in a healthy way. What kind of lingering trauma
do you still have from prison? Do you have nightmares at all? Do you have flashbacks? No, I've never
once dreamed about being back in prison. I've never once woken up and really thought I was in prison,
which things I'm incredibly grateful for. That being said, there are definitely some environments
where I feel myself going crazy. There's some times where, like, I don't sleep really well through
the night. I lay my head down, I go immediately to sleep. And then two or three nights a week at 12
or one or two, I wake up and I'm just like shock awake. I'm full of adrenaline. I'm like ready to
go. It feels like something happened. And I don't know where that came from, but prison's the only
place you can think of because it didn't happen when I was younger.
So having been through some of the things, having, you know, when I think about it, it's like in prison in a weird way, the safest I ever felt was when I was locked in that cell at night because, you know, there's only one other person to deal with and that door was locked. Like, I'm going to hear if that door opens. But sometimes in the middle of the night you'd hear the screams or something horrible happening or I don't know. But it almost feels like now because I'm in the world where I don't, like, I have a lock on my door and I guess I could lock it, but it doesn't feel the same as a giant steel door. It almost feels like I don't know how to be secure because there isn't a giant steel door holding me inside.
And in a weird way, I feel like that the strange structure that I found in prison got me acclimated to like living in that cage.
And now it's almost uncomfortable to live in the world.
Yeah, you know, it's funny you bring that up because I felt the safest when I was in the shoe or solitary, whatever you want to call it, when you're locked in there because you know the only one that has the power to open that door is the prison guards.
You're protected from everything else.
It's just you and yourself in there, which is a very lonesome place, but it's also a peaceful place too.
and something that could bring you so much pain
could also bring you so much peace
and that's just like a whole
different area of the mind to really think about
and a mental capacity and stuff.
100%.
I mean, I think about that from time before,
but also people now.
When we've been hurt by somebody else
or hurt by an environment,
we draw into ourselves,
which then prevents us from having those relationships
and prevents us from healing,
but it's the only place that feels safe.
I mean, that's why when I'm in a really bad mental state,
my first impulse is not to reach out
for people and get help.
It's to draw into a corner and cover myself up.
It's to run away from everything in the world
when ultimately what I need to do in that place is to heal.
I need to be around people that are healthy.
I need to allow myself to go out in the sunlight.
And allow myself to do all that.
But often the trauma that was caused by other people
causes us to kind of forever feel like we need to be alone
or we need to be isolated or away
because we're afraid or we're afraid of the environment
or we're afraid of the people or we're afraid of the effect.
And it can be isolating in a way that's probably just as traumatizing
as the initial effect of whatever happened.
What have been some challenges of having a platform
and being in the public eye.
The only real challenge I see is, again, trying to be accountable, trying to be honest,
trying to be authentic.
But, you know, how to take a stance on things or not?
Because, I mean, I have my own, like, political views or I have my own personal views.
But I don't necessarily want to focus on things that divide people.
I really want to focus on things that bring us together.
So when I see something as egregious, I'll call it and say, hey, I think this is absolutely
unacceptable.
Nobody, regardless of their political affiliation, their gender, their whatever, should
ever do this.
But for the most part, I try to only focus on the things that we can all kind of agree.
on because we have such a partisan divided society right now on every front that I don't think
it helps to kind of point things out. And that's one of the reasons like I'll do kind of segments on a
news story. If I see a news story about like a horrible thing that happened in a prison, well,
let's talk about the failures of the staff that runs at prison. Let's talk about the failures
of the people who live inside. Let's talk about all this and not just put blame on one person.
Because as much as I remember what it felt like to be a victim inside a prison and, you know,
blame the staff or blame whatever was going on. The realities, again, we all have to take accountability
to trying to really like step back
and not just respond emotionally
or react emotionally,
but really take stock of the situation
and speak from a holistic perspective
because otherwise all we're doing
is contributing to the divide
and just like creating, you know,
walls that we're throwing stones at
from each side.
What's a day-to-day life are you like now?
That really depends.
On a typical average day, what are you doing?
When I'm home, I mean, I'm on the road,
I don't know, probably anywhere from a day
to a week a month.
When I'm at home, again,
I try to have a structure
because that was what I found inside
that really worked for me.
So I'll get up and I'll go to, again, the apartment gym,
or I'll go to the jujitsu, I'll come back,
try to sit and meditate for a few minutes,
I'll make coffee, I'll walk down to the co-working space.
I'll sit there and talk to the staff for probably 15 or 20 minutes
because one of the reasons I go there isn't just to work.
It's because I don't have this, like, I don't have colleagues.
Like, I work by myself, the nonprofit.
We're hiring an operations person who lives in Texas.
I don't get to have that kind of like office banter,
which I'd really like, so I find that there.
Then I'll sit down, I'll start responding to email,
I'll start working on proposals,
we'll start reaching out, depending on what kind of project we're working on.
It may be technical things like this cloud-based thing we're producing.
It may be reaching out to foundations for money.
It may be filling out grant proposals.
It may be reaching out about speaking opportunities.
It may be just responding to emails.
Because again, I get, I don't know, probably five or ten emails a day from somebody who is formally incarcerated or is facing time in prison.
Who has a loved one who's locked up.
And that's not really a part of my job, but I feel if I have the time to do it, I want to respond to those.
Because I know how much it meant to me every time somebody was willing to take my call or respond to my letter when I was locked.
up when I felt hopeless and my fault alone, that if I can show up for those other people,
this is me just passing on the good that was given to me.
I'll usually kind of run through that through the course of the day. I have meetings.
A lot of time they'll be on Zoom. Sometimes it'll be in person. Sometimes it's in Richmond or
D.C. Sometimes I'm driving maybe on the train or I may get on a plane to go somewhere else
for meetings or for opportunities or speaking engagements. I also started an interning at a venture
firm because we talked about, I don't just want to focus on prison reform or just talk about prison.
I want to figure out what the next chapter my life is.
And I've been really interested in tech.
I've been really interested in business.
I didn't know anything about it.
So I could go back and spend $120,000 and get an MBA
where I can spend two years interning a venture firm that does med tech and health tech
and see every side of a business, see every side of operation, see every side of scaling
and exiting, see every side of the investment equation.
And I basically get that MBA education for nothing.
And like even theoretically, I get upside equity in the product we're investing in.
And so I'm trying to give that about 15 or 20 hours a week so I can find
focus on that being my education and building relationships.
So basically, as one of the people that I'm close to back home says, like, I just don't stop.
I start early in the morning and then like eight or nine at night, I finally turn my computer off,
and I try to watch TV and that's it.
Or I go out with friends or I go out on a date or I go do something.
And then it feels like I just, I don't really have any time to myself that isn't work or
immediately around other people.
And that's where I'm trying to build in a little more time to like come back to myself,
to rest, to relax, to kind of reflect, to read.
I mean, I love reading.
I go from reading two to three books a week for 19 years to reading two or three books a year.
Like I'm kind of slacking.
What's like the next five years look like for you?
What's like the Jesse Cross and five year plan?
So we need to get funding.
We're looking at the runway for the nonprofit.
If we can get enough funding, I see myself probably exiting the role as the executive director
and allowing basically hiring somebody else, probably somebody else who's formally incarcerated,
to run the operation because I feel like, you know, maybe I can continue to have the biggest
an impact there, but I feel like in some ways I may have a bigger impact by kind of building
wealth and being able to influence policy through that. And I have a friend who inspired me
of this because she said, you know, I could go work for a nonprofit for $45,000 a year and maybe
make an impact and maybe just turn my wheels, or I could go work for corporate America, make
$140,000 a year, give $30,000 a year to charities that actually need it, still make more money
and still have a bigger impact. And I don't know which of those I feel, but I'll always continue
to do advocacy. I'll always be going to the General Assembly or going up to D.C. to speak.
I'll always continue to network and reach out about things that I think are important.
I could see myself staying in venture.
I could see myself spinning off my own company.
We've got a couple investment opportunities I'm looking at.
I could see myself doing some real estate stuff and really focusing on providing housing for returning citizens.
Because I think everywhere, but especially in the area that I'm at, the housing crisis is just the biggest problem.
Because people don't have a safe place to live.
And if you look at Maslow's hierarchy, if you don't have the base level, you can't worry about self-actualization or growth or development.
You don't have a safe place to live.
So that's an area that I really would like to affect not only for returning citizens, just for anybody who's looking for affordable housing.
But I also don't know.
I mean, I didn't think I'd be here in New York.
And then all of a sudden, I'm here.
I didn't think I'd be at South by Southwest.
I didn't speak.
I'd be speaking in front of TikTok.
So I recognize that I have a limited perspective on what's coming.
And I just have to kind of have an open door to allow whatever's going to come to happen and not block myself off from an incredible opportunity.
I mean, two years ago when you were walking out of a Virginia state prison, did you ever think you would be doing this?
Like this would be the life you're living.
And you came out with nothing.
You didn't have anything.
Yeah.
Nothing.
And even a month after that or six months after that or a year after that, I didn't imagine this.
You know, when we had that first get-together at prison talk people, it seemed like a crazy idea.
What would do it?
And now everybody takes it for granted.
When are we doing the next one?
How are we going to do this?
When I first, you know, started the nonprofit, I was like, God, what am I going to do?
This feels crazy.
Like, how am I going to, like, responsibly steward this?
And now I feel comfortable.
I have conversations about it, you know, every day with people all over the country.
And then, you know, the venture thing.
Man, when I started talking to this guy, I didn't know who he was.
And that's been the biggest advantage I've had at each one of these conventions and conferences.
I don't know who anybody is.
This guy's a billionaire.
I don't know that.
He's just, he's some guy eating a taco.
Hey, you want to talk about tacos?
You want to talk about sports?
And I think that that's what's allowed me to build these relationships because everybody
goes to each one of these people pitching something.
And instead, I'm like, hey, let's talk about tacos.
And I think that that's probably refreshing because they actually get to have a genuine
human interaction.
and that's kind of, I guess, the value that I bring.
And I want to continue to, like, share that with other people, because what I've seen in all those worlds, and I saw this in prison too, you have people are transactional.
Like, everything is about making money.
Everything is about getting a return.
And you have people are non-transactional.
And they will help you out and they will introduce you.
And they just want to meet people.
And they've been by and far more successful than the transactional people.
These people like them.
They want to work with them.
They want to spend time with them.
And so I want to continue to be that person who can allow other people to support.
Like, hey, you need something.
How can I connect you with the resource you need?
or you need investment for a really good business idea.
Hey, let me connect you with an investor.
You've got a nonprofit idea.
You want to do a service thing.
Hey, let me connect you with this foundation that can give you money.
Because it doesn't cost me anything to use my time to somehow try to help somebody out.
And if I can continue to do that, I feel like that's going to somehow or another get me to a point where I feel even more comfortable than I am today.
Absolutely.
Well, Jesse, thank you for coming back for round two.
It's been an absolute pleasure talking to you about something different than we're used to talk it about.
We didn't talk about any ramen noodles or prison stabbings or anything.
So hopefully that gave you a bit of a refresh today.
And I appreciate our friendship, our relationship,
and just excited to see you grow and prosper
and continue to be that hope for individuals
because there are a lot of people that come out of prison with nothing
and they look and they see what you've been able to build with nothing.
I think that speaks wonders right there.
Thank you, man.
