Episode 226

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Episode Description

What happens when you worst fear becomes a reality? Even after telling yourself so many times that it will never happen to you. When an unexpected life event takes you from hero to zero, it can be hard to see any hope of bouncing back. For those of us who have hit rock bottom, it’s a feeling that we know far too intimately. But what happens when you pick yourself up and choose to make something great out of the ashes? And even better—what if you could use that experience as fuel for a more fulfilling life?

That’s exactly what happened to our guest, author and podcaster Brent Cassity. His life came to a sudden halt after an unexpected oversight in his business landed him at the Gates of Leavenworth Prison, ready to face a five-year sentence head on. This life experience offered him the chance to reevaluate his purpose and find hope in difficult circumstances. He’s taken these learnings of reflection with him on his journey out of prison – knowing that outside the prison walls, we are often imprisoned by our own thoughts.

In this episode, Brent unlocks the power of five life-changing tools he used to help him find resilience and inner strength to move forward during this difficult time. Brent hopes with these key tips at your disposal, you can discover how to make progress towards emotional freedom and fulfill your true potential!

About Brent

Brent Cassity was an innovative CEO of Forever Enterprises, which he grew from a regional company to a national company operating in over 22 states. Brent was recognized by the national media; TIME, Fortune, Wall Street Journal, to name a few. HBO even did a documentary that spawned the TV series “Six Feet Under.” Just when he thought he had it all, he lost it all and found himself serving a 5 year sentence. He has coined the phrase “Nightmare Success” because everything you want in life is on the other side of fear.

In his Book, Nightmare Success: Loyalty, Betrayal, Life Behind Bars, Adapting, and Finally Breaking Free, Brent shares survival tools that helped him adapt to prison that can be used in everyday life for those who are stuck and fearful of continuing to step forward.

Brent’s Book

Brent’s Podcast

You can also check out Brent’s podcast, Nightmare Success In and Out, where he explores the stories of inmates who were in and now out of prison. What was life like before they went in, life inside prison, and life now that they are back home. These conversations are deep, sad, often funny, but always interesting.

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Episode Transcription

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[00:00:00] Bob Wheeler: What happens when your worst fear becomes a reality, even after telling yourself so many times? That will never happen to you. When an unexpected life event takes you from hero to zero, it can be hard to see any hope of bouncing back. For those of us who have hit rock bottom, it’s a feeling that we know far too intimately.

But what happens when you pick yourself up and choose to make something great out of the ashes and even better, what if you could use that experience as fuel for a more fulfilling. That’s exactly what happened to our next guest, author and podcaster, Brent Cassidy. His life came to a sudden halt after an unexpected oversight in his business.

Landed him at the gates of Leavenworth prison, ready to face a five year sentence head on. This life experience offered him the chance to reevaluate his purpose and find hope in difficult circumstances. He’s taken these learnings of reflection with him on his journey out of prison, knowing that outside the prison walls, we are often imprisoned by our own thought.

In this episode, Brent unlocks the power of five life-changing tools [00:01:00] he used to help him find resilience and inner strength to move forward during this difficult time. Brent Hopes. With these key tips at your disposal, you can discover how to make progress towards emotional freedom and fulfill your true potential.

In his book, Nightmare Success: loyalty, betrayal, Life Behind Bars, Adapting and Finally Breaking Free . Brent shares survival tools that helped him adapt to prison that can be used in everyday life for those who are stuck and fearful of continuing to step forward. Also, check out Brent’s podcast where he explores the stories of inmates who are in and out of prison.

What was life like before they went in life, inside prison, and life? Now that they are back home. These conversations are deep, sad, often funny, but always interesting. I’m Bob Wheeler and this is Money You should Ask, where we explore why we do what we do when it comes to money.[00:02:00]

Brent Cassidy was an innovative CEO of Forever Enterprises, which he grew from a regional company to a national company operating in over 22 states. Brent was recognized by the National Media Time, fortune, wall Street Journal to name a few H B O. Even did a documentary that spawned the TV series six feet under just when he thought he had it all, he lost it all and found himself serving a five year.

He has coined the phrase nightmare success because everything you want in life is on the other side of. So exciting to have you on the show, Brent.

[00:02:43] Brent Cassity: Bob, thanks for having me. I am excited to be on your show. I’ve followed your show. It’s a great show. So here I am. So here

[00:02:50] Bob Wheeler: you are, and your story, man. It’s some success and as the name of your book, nightmare Success as well.

So you’ve got [00:03:00] all these different experiences. You’re a published author, you’re former C e O, your current vice president of development at Remax Gold, and a little bit of stuff in between. Can you tell us a little bit about your journey? Yeah.

[00:03:12] Brent Cassity: In your show, Bob, you know it intertwines with money. Yeah, and I had kind of an interesting life growing up cuz my, I had a dad that was, how do you explain him?

He was the guy, you know, everybody’s got their own relationship with their dad, but he was like bigger than life. He had won his state championship. He had gone to law school and graduated number one. His class sped out of there and started one big cases and got into businesses and. Doing well. I mean, I didn’t know anything any different and about the time I was about 14 years old, everything was great.

I kind of grew up in a Norman Rockwell city. And he called us in one night and he says, I’ve got a problem with the bank guys and it, my brother and Ma. And he said, I’m gonna plead guilty. I, I was seeing his mouth move, but I was thinking, you know what, how does the guy [00:04:00] that has the golden church, and, and by the time he got done with that, he said, and I’m gonna plead guilty and we’re gonna move out of town to St.

Louis. Which St. Louis was like a gigantic. I mean the unknown, and I was thinking this is the worst family meeting that could have ever have happened. But what I was thinking about that was at that time, as a kid moving to a big new place, dad ends up going to prison for six months and we lost everything.

Yeah. It was kind of a weird dynamic as a child because as a teenager, Having everything, losing everything. We had to kind of figure things out. The one thing that was really weird to figure out was we move into a neighborhood like, where’s the dad? Right? Did they get a divorce? Did he die? So our thing was, is that dad’s working out of town.

That was kind of true. He did have a prison job out of town. But , the, the crazy thing was, is dad came back and there was one business that survived this whole thing. I mean, we literally lost everything. We had so many different businesses. [00:05:00] I don’t even know what. One business, and it was a very unsexy business that was taking care of your funerals ahead of time, called prearranged funerals.

And he had put it in a family trust, so that’s why it survived, and he gets out and makes it all over again. So my feeling about. Money at that time. And what you could do at that time was, and dad always said, you know, if you’ve got a good plan and you stay focused and you’re not afraid of the unknowns, step into it.

You can make it whatever you want to make. So I grew up believing, wow, you could even go to prison and you can make it back. So I had kind of a weird feeling about money, success, loss, failure. Can you make it back? Because I had this dad that did that. So the crazy thing about it was that when we went to visit my dad in prison, that’s a very weird thing because you all of a sudden realize, Bob, that.

Oh my gosh. It’s going through your mind. We’re that family now. We’re that family that [00:06:00] goes and visits your dad in prison. And he was at the time where he went. It was a very respected guy. And now we’re going and he’s gonna enter the room with these prison clothes on. Strange. Yeah. Can’t even tell you how strange it is.

But the other thing that came into my mind after that first visit was, That’ll never happen to me. , whatever I do in my life, I will never find myself there. Well, , as the story goes, it certainly did. And it was years down the road and back with my dad and a few other people, it did happen again. So life is funny and how things happen is incredible.

But I just wanted to bring that up at the beginning is, is that my feeling about success? Failure loss, making it back. I believed that when I was in high school. I thought, you can do this. Yeah. You could actually lose everything and rebuild like

[00:06:55] Bob Wheeler: father, like son . Yeah. Do you remember though when [00:07:00] you moved and you had to present like dad was just outta town?

Was there any anxiety about like, I hope my friends don’t find out, or it was the family’s secret that was the cloak of shame or whatever?

[00:07:14] Brent Cassity: Yeah, that was really strange because almost all of my friends didn’t know anything about it. I was the new kid. Right. I was very lucky. I, I was a good athlete and so I was really involved in sports, playing basketball, so that was my release, that was my escape.

And so, Nobody really asked a lot of questions. I had one friend that had had issues with his own family on the legal side, so we became close and I was able to share with him. But it was very strange though, Bob, to have that secret, and I don’t think it’s healthy. Well, I had great parents growing up, but I don’t think that’s a healthy way to handle it.

I think it’s much more important to. The difference between victims and surviving. Be a survivor because victims takes away all your strength, [00:08:00] all your ability to fight. Yeah. Surviving gives you strength and gives you that mindset that you can get through anything. That’s what I did with my kids. I have three incredible daughters that are 30, 28, 25 now, and when we went through what I went through and we went through a gigantic public spect, It was covered on media, national media and whatever, but we were very open with, my daughters told them exactly what was going on, but we really locked in and said, Hey, we’re not gonna look at the news.

We’ve got great friends that are supporting us. We’ve got your teachers that are being supportive. We’ll gonna lock into that bubble and walk through this. And I look back on that now, and I look at my daughter. And how they went from a very privileged life. They were in private schools, they had a home in Nantucket.

There was nothing that could be not attained for them or I would give them, they went to birthday parties in a limousine, but when that world changed for them, They locked in. They worked in college. [00:09:00] All three of ’em worked at a popular bar that was at the University of Missouri. Made good money and I couldn’t have been prouder of how they changed it.

And I think a lot of that had to do with my wife. I met my wife when she was 13 years old. I was 15. So we had kind of gone through every life stage together. . Yeah. And she was really the glue that held all that together for us. And I don’t know how I got so lucky on that, but I really believe that that’s the thing that kept my world and my daughter’s world real normal.

Yeah. And in a very abnormal situation. Well,

[00:09:33] Bob Wheeler: and in your case, you had started this business that had stayed in the trust. Everything was good. You thought you were doing really good. Yes. And you brought your dad back and he was working for you, and you employed all these people. You’re out there doing good stuff.

Maybe you know the funeral business isn’t that sexy, but you grew it, found this market. You did all these Yeah. Amazing things. And people are coming to work. They’re super excited. To be a part of this vision [00:10:00] and then little compliance issue.

[00:10:02] Brent Cassity: Yeah, and here’s the thing. For people who want to make money, making money is fun.

There’s a couple of things as you want to find a passion. We had a passion, we got into the business. The unsexy part of our business was the prearranged communal business. We had kind of a sexy part of our company that we became known in the industry as the innovators because the business hadn’t changed very much in the last 150 years.

But we actually came up with an idea that we were going to become the filmmakers for everyone else. Famous people get it every time. When somebody dies, queen Elizabeth dies or whomever, and they get the highlights of their life and you expect it. If somebody dies today as a celebrity, then you’re gonna see that, that you’re gonna expect it.

Right? So we sat around the table one time when I was young and Tyler was young. We said, let’s become the filmmakers. Well, we did that and we actually created a company called Forever Enterprises, started buying cemeteries where we actually created a production company. And the cemetery was where people went to remember.

And there’s an old African proverb [00:11:00] that. When someone dies, a library burns. So we wanted to become a library of lives. Nothing had changed in the business in the last 150 years, so we started creating these life stories for people. So you could go to a touchscreen console and meet that great-grandmother or that grandmother or that uncle that you hadn’t met, and they introduced generations to each other.

Well, that became something that got a lot of positive press from the front page of the Wall Street Journal to Forbes to Fortune when we bought Hollywood Forever Cemetery out in in la. We were on the cover story of Entertainment Tonight. And then H B O decided they were gonna make a documentary called The Young and the Dead.

So we were on a fantastic role. Right, and in that momentum of that, you feel it and it feels good, and you think I’m following our passion, we’re changing things, we’re making a. Well, the one thing, Bob, that I wasn’t paying any attention to was that we had an insurance company and I never liked math and I loved sales.

So that insurance company funded these contracts for the prearranged [00:12:00] funerals, and I didn’t pay attention to it. And it was something that I thought, it’s all good. Dad’s got these people here. He’s a financial guy, and we’ve got a guy that’s been with us for. And I thought, if I take this money and I put it over there and everybody keeps paying, there shouldn’t be any problems.

And so we expanded from three states to 25 states and it was all good. And that’s when for people who have businesses, you can’t actually do that. That’s not smart. Now you can take somebody and pluck them out and say, that’s the best insurance guy out there that I can buy and put them in and have them do that.

And they report to you. We didn’t do. So exactly what happened to us was, is that we did get into a compliance issue. We got into an ugly situation with our reinsurance company, and when you get into a regulatory environment that’s tight as tightly as it is in insurance, there’s a lot of different missteps that you can make.

Not even intentionally, but you can make ’em, and it makes the whole world look. And that’s [00:13:00] what happened to us. And it took us six years. Six years that we went through fighting that battle and lost everything. I say. I lost everything. I really didn’t lose everything. They didn’t take my brain and they didn’t take my family.

Right. And one thing about hitting rock bottom, it can give you clarity and losing everything. You don’t have to worry about that anymore. Right. But one thing that I think that if you. One thing you never wanna lose is the ability to have your imagination, creativity, curiosity to figure it out. I think maybe I’m just wired that way.

Maybe I got it in my jeans, but I always think that there’s a way that it can be figured out. I always say this, nothing is as bad as your mind makes it out to be. Right. for sure. Not even prison, right? Not even prison. But

[00:13:46] Bob Wheeler: what was going through your mind when you’re standing at the gates of Leavenworth, like, here I am.

It’s time to pay the piper. Right? It’s like I’m stepping up. What goes through your mind? I can’t even imagine

[00:13:58] Brent Cassity: it was. I had had a [00:14:00] rock bottom moment before I ever stood at that gate. And thank God I’ll remember the day like it happened yesterday. I came to my grifts. I was being the victim. I was being poor me.

How am I ever gonna live as an ex-felon? How my kids, how I’m, all those things went through my my, and I wanted to end it, and it hit me like a lightning bolt. Like, oh my God, Brent, what are you doing? What in the world’s gone through your. You’re the glass half fool guy. You would look like an idiot. Your kids would see you as the biggest loser of no.

However you left your legacy, you weren’t that guy. So at that moment, I thought, no matter what happens from here on out, even if it scares me to death, I’m gonna step into this. I’m gonna try to make everybody proud of how I’m handling the situation, and I’m gonna figure this out even if it scares me to.

When I was standing at those gates, when I got that envelope, they just mail it to you. That was what’s so weird cuz I got to voluntarily sprint it. You open this envelope and it says Leavenworth Prison. I was like, oh my god, I’ve heard of that one. . I feel like I’ve seen that like in movies or something and Right.[00:15:00]

I was like, oh boy, this just goes, go bad to worse. I remember the night before that we went to the prison, my wife and I drove up and it was just kind of getting dusk and you could see the guys walking the fence with a bob wire and you could start to see the lights that were on and the inside there.

And I didn’t say anything to Julie, but I was thinking, oh my God, that’s gonna be me. Tomorrow for not just a few days, not a month. I’m sentenced for five years there. Yeah. And that feeling of that is, I’ve gotta get myself together. I gotta figure this out. So when I was standing into the gates of Leavenworth, I was thinking that everything behind me is everything.

I know everything I love. Everything in front of me is the unknown. How am I gonna handle this? What I found was, first of all, it was no matter what, it’s scary to walk through that gate. Yeah. I don’t care how much somebody says that they’re the biggest man in the world and they’re wearing a cape and all that.

It is humbling. [00:16:00] There’s nothing more humbling than going through the process of going through being prisoned. But my biggest surprise out of that though, Bob, was after I had gone through all that and I’m carrying my stuff, all bed rolled up and my new these clothes and boots and everything else, and I get to this big open room where there’s 50 bunk beds.

Everybody’s got a bunk bed, a locker and a plastic chair. And I was thinking as I was walking through there, my gosh, my. As big as it was has been reduced to a plastic chair, a locker and a bunk bed. Yeah. And immediately as I’m thinking this, this Hispanic guy walks up to me, kinda is shorter than me, but he’s real blocky.

And he says, boy, he says, you don’t look like you’ve been here before. I should, that’s true. I haven’t been here before you, so you’re gonna need some help. And he immediately says, okay, we gotta teach you how to do this bed military style uhoh. We can’t do anything with that locker. I gotta help you clean that out.

You’re gonna need some shower shoes, Watson, give him your shower shoes. And immediately he’s helping me. [00:17:00] And he walks me over across the room and there’s this guy standing there. He says, Clark b Cassidy, he’s one of you. Help him out. And strangely enough, Bob, I find that Jim Clark, eight years, my senior from St.

Louis went to my school of Dism, played basketball. What a weird connection, . And from that point forward, Jim was helping me out. Roma was helping me out, and I went down because Jim told me I could make a phone call to my family in the counselor’s. I get on the other line and it’s my family, and it was very emotional because I knew that they’d been waiting for me to call and I said, kids, Julie, I’m gonna be okay.

Don’t worry about me. There’s some people here helping me and I’m just fine. And from that point forward that night. I remember in my bed looking out and there was the big prison on the top of the hill all lit up. And I was looking out and I thought, you know what I need to do? I need to write down some goals like I’ve always done when I was in business [00:18:00] trying to figure out how I’m gonna get to the next step.

And so by the light of, we were close to the restroom there and it was coming through, I had some paper and a pen, and I started writing down what I wanted to accomplish. While I was in prison, and those are the things that steadied me, Bob, because it made me feel like me. The biggest thing that I was worried about going to prison was is I was gonna lose me.

I was gonna become ized, right? I was gonna become institutionalized. The old Shawshank Redemption movie, there’s a lot of interesting phrases that are in there that are so meaningful and so true. Get busy living. Get busy dying. That’s. The people that have given up and the people that are trying to make it work, there are no in-betweens.

Yeah. And so I knew that no matter what I had to do, I had to keep on the right side of this thing to keep myself busy, keep myself being me. So my biggest thing was most books I’ve ever read in my life and read a book a week, I got in the best shape of my life. I found a good prison job. I got into the program that earned me a year.

And I figured out how to [00:19:00] find people who were getting it right so that I could borrow that and get through my time better. Those were my basic goals. And then I had some tools that I used to get through prison that I talk about when you go into a new place, and I’m not talking about any place, I’m just talking about just prison.

Go into a new job. Yeah. First thing you wanna do is humble. You know, look around, see who’s getting it right, check it out and go talk to ’em. See how they’re doing it. I did that when I was a young 20 something in business and I did it in prison, and both of those things worked exactly the same. Humbling myself, looking around, seeing who’s getting it right and asking them questions.

Got me true. The next thing was, and I just told you this, was finding your Zay goals plans, you know, and the movie Shawshank. What kept him? Andy de frame chipping through the wall for 19 years. He had Zay in his head, the widest white stands, the bluest of the Blue Pacific, the place, the boat he was gonna fix out the little.

Andy was gonna have his friends over those things, and then he would let that wall [00:20:00] out into the yard every day as his daily reward. So I had to have that in prison. Day one, Teneo, what is it? Third one was, is when of the day. One day at a time. Unfair. Things happen. Make a difference regardless. And my daughter, my youngest daughter made me a calendar every year.

So part of my routine was that when I went to bed is I would ride in that little square on the calendar. and I looked for the win for the day. And if I couldn’t find a win for the day, I knew that I had had a bad day. But the one thing I didn’t let myself do is fill in two boxes of bad, because I knew that that would make the go down a slippery slope.

And once you’re in a slippery slope, that can turn into a weak a moth the year. And then you’re lost. Yeah. So the fourth thing was, is learn from your mistakes. I mean, that’s a big one for me. . Yeah, obviously. But the thing of it is in business is, is so many people in this day and age are so afraid of mistakes and so afraid of failure.

All the great people who have written books about business, they’ve all made mistakes. They just made them wiser. [00:21:00] Like Jack Nicholas says, you’re gonna make a bad golf shot. Just don’t make two bad golf shots in a row, cuz it really messes up the hole, right? . So it’s important to know, don’t get anxiety ridden on making mistakes.

Just know that when you make a mistake that you’ve learned and you, you’re gonna grow from that, and that’s gonna be the thing that’s gonna make you better. The fifth thing, the final thing that I worked on in prison at Can instead was, is don’t give in. Don’t give up. Keep being yourself regardless of the circumstances.

Otherwise, you will lose what makes you. That’s why a good prison job was important. That’s why reading was important. That’s why staying plugged into my family was important. The biggest fear was, is don’t become institutionalized. And then once you get out of prison, you start realizing that there’s a whole bunch of people that have built up prisons in their own mind that are institutionalized.

Bad marriage, bad job. Yeah. You know, a health crisis, whatever that is. And they get stuck and they don’t take that opportunity to set themselves free to whatever it is they’ve always wanted to do. I’ve always said, you don’t want to be the guy, the 85 year old sitting in your rocking chair thinking, wow, back when I was 35 [00:22:00] years old, I just wish I would’ve stepped out and made myself a little uncomfortable and done that, cuz I think I had the talent.

You don’t want that? No. Just do it.

[00:22:08] Bob Wheeler: You gotta do it. Well, let me ask you this. You gleaned these lessons and many of us are in our own internal prison, but before you got to the gates, and I don’t know when, like I know if it were me, I probably would’ve 800 times replayed everything in my mind to that critical moment, and I would’ve been like, But maybe if I had done this, or maybe if I had read this page.

Yeah. Or maybe if I had had the eggs or maybe, and maybe a little bit of spin out, but I just know me, I would’ve overthought like, how did I get here? Wait, how did I get here? Yeah. And I’m wondering if that happened for you, cuz I know a lot of people probably are like me. That would’ve just been like, wait a minute, if I hadn’t turned left, if I had Right.

Did that happen

[00:22:51] Brent Cassity: for. Absolutely. And the problem with that is that once you’ve gotten to that point, you can’t fix what happened in the past. What you [00:23:00] can do is be very aware that you don’t want that to happen again. So what it does for me is it gives me true perspective of business is something that you can’t get blindsided with.

And I think the one thing that happens in business, When your business becomes successful, it’s easier for you to get blindsided because things get easier. They don’t get easy. One thing I’ll also say about money and business is that a lot of people think that at a time, for a few years there, I didn’t even look at prices of things because I had reached that plateau.

Right, but it in no way took away all the rest of the problems in my life. I didn’t have that to worry about. Money wasn’t a problem that was beside, but everything else still comes out to you a thousand miles an hour, kids, schools, problems, all those things still happen and I think that’s one of the things that people can get really confused about.

And one thing that I can say now where I’m at, I’m doing this podcast now, nightmare Success in now, it’s, it’s about what happens when your worst fear becomes your reality. How do you adapt, survive, and. [00:24:00] And I talk to people who’ve experienced Prism and all these are different stories, but the one thing that I think is so important is no matter where you are in your life, make sure you’re doing your passion.

Like right now, what that does for me is when I was walking the fence in Leavenworth thinking, oh my God, like you’re saying Bob, Woo. This is really bad. What am I gonna do now? ? Yeah. This isn’t as bad, as bad as it could get. Yeah. What can I do? Cause I felt, and always growing up in my life, I wanna make a difference.

I always told my girls, whatever you do, girls make a difference with whatever you do. So I thought, what do I do? And so I decided that this has been such a journey. So unbelievable. But the biggest truth out of it was, is that you can survive, you can adapt, you can overcome just about anything. And I thought, I’m gonna use this experience and try to help others through their dark places, give them strategies to get to the next step.

And nightmare. Success is really about that. The book, the podcast, because there is no success unless you walk through your fears, [00:25:00] right? There is no success unless you walked through your unknowns and night. And that success is willing to go over, under a round climb, over the top, whatever that is, those are the people that find it.

And you have to have two things. One is, is the ability to have the confidence to walk into your fear. And then the passion is usually follows that, you know, the mindset’s so important. One of my favorite quotes is Henry Ford, whereas he says, whether you think you can or whether you think you can’t, you’re.

Isn’t that so true though? I mean, what you wire your mind to believe and it believes what you tell it. Whether you are in prison or whether you’re saying, I gotta jump for that job. I have gotta go for that promotion. I’ve gotta go out and start my own business. All those things. I always believe that there’s somebody out there that’s doing something very similar to what you want.

You just need to go figure out how they’re doing it. Yeah. Borrow the pieces that they’re using in their success and put it and implement it. [00:26:00] I did that over and over in our business and two or three times, the only original idea we had was filming people before they died. Everything else I literally borrowed from people and implemented in our, because I knew that they were already doing it.

Well. You don’t have to reinvent the wheel in business. You just gotta find it. You just

[00:26:18] Bob Wheeler: gotta find it. You know? You have this mindset that’s certainly helpful, and obviously having the support of a family that’s there for you is probably incredibly helpful. Did your relationship with money change when you came out?

Were you like, wait, I gotta get it together because everything’s gone. I have to reprove myself? What was that like when you got to walk out the gates of Leavenworth and now enter the world again? Re-entry

[00:26:44] Brent Cassity: is really tough because first of all, the most exciting thing that’ll ever happen in your life. The only thing I can compare walking out of prisoners is like when you’re five years old and you go downstairs and you see the Santa Claus has come and he is brought all these gifts time’s that by a thousand.

[00:27:00] Yeah. And that’s what it’s like walking back out to your family. But there’s some things that go on in your mind to get your feet back underneath you. One is, is if you’re gone for a while now, how’s everybody doing? And like, my wife is now taking care of the bills. I always took care of the bills. How do I fit back into this world by not interfering, but being a part of it.

It’s like jumping into a moving car and it takes a little bit of. To figure out. A lot of things are just sensory overload. I mean, I, I remember we stopped off at a gas station and it had all this stuff. Just, yeah, everything. And I was like, oh my gosh. And I didn’t want my kids and wife to think that I was freaking out, but it felt weird.

And then we got out there to pay for it and they were like, dad, you gotta pay. And I hadn’t paid for anything for three years. So , it took a little bit of time for me to adjust to that. As far as my money part of things, having money is definitely a great thing. It’s nice. And for people who say that money is not great, it is.[00:28:00]

But it’s not the thing that makes you happy. So what I had to do and find for myself was, is what’s gonna fill me up? Yeah. What’s gonna make me feel like I’m Brent and be the person that I was before I went in so I can keep doing things that make me feel good. And so it took me a little bit of time. But I found it.

And am I anywhere close to the type of wealth that I absolutely not. Will I ever get there? I don’t know. But I don’t need that. What I need is to know that I’m going to use everything that I have. I’m gonna make my kids proud that I’m working towards my own passion. And if they see that, then they also know they can do.

Money is a byproduct of we live in a society where that’s a scoreboard, right? If you’re doing well, then you’re making a lot of money. But there’s people who I see that do pretty well, not making a lot of money, but they love having that little lake that they go fish and they have the families and the Sunday [00:29:00] dinners and.

Whatever somebody’s success is is so different than someone else’s. And it doesn’t necessarily mean that that’s got a dollar signed to it. It’s what they’ve found for themselves.

[00:29:10] Bob Wheeler: Yeah. I think we have to find our passion. Money’s great. It’s wonderful. And our relationship with it, I think is more important than, and then how much we have the

[00:29:19] Brent Cassity: relationship.


[00:29:20] Bob Wheeler: And understanding that yes, it can certainly help make things easier. It doesn’t necessarily make things happier.

[00:29:28] Brent Cassity: And I had to come to grips with the fact. Did I miss some of the things that I had? Yes. I wouldn’t be honest to say that I don’t miss some of the things that I had, but were they the things that were making me happy?

No. What I would’ve really have been upset with is what I saw happen in prison were so many men that I was with lost their families. Right? To me, I don’t even know how. Cause if you gave me a million or $2 million and I lost my family, I would be a very sad. So I [00:30:00] came out of prison knowing that I had something that a lot of guys didn’t have, and I had a really strong family that stayed together and became stronger.

I always say when someone goes to prison, the family goes to prison. So each one of my kids and my wife had to handle. That time your own way. Right. But I will tell you something really weird. So my dad ended up going to prison a second time with all of us, and he got more time than me. So when I got out of prison, I went to visit him and.

Bob, that had to be maybe one of the strangest things that’s ever happened in my life because I went exactly back to the same prison. Oh wow. That I was at a 15 years old and walked through those doors. But now I had a little bit of P T S D because I know what he was walking when he walked around that corner.

I know what’s behind there. But to be there at 50 years old as opposed to 15 years old, but actually being in prison for three years to go visit my dad again in. Wow, that was something you [00:31:00] can’t make up or even analogize that to anything that I know that you could analogize to. It was just the most strange situation that I can imagine for the mind to deal with.

[00:31:10] Bob Wheeler: That’s pretty surreal. I mean, I think sounds like even through all these experiences, realizing the value of family, because I think we don’t always put a price on that. Yeah. And we sometimes take it for grant. Or assume it’ll always be there and things like prison and stuff like that can be a game changer.

Huge game

[00:31:29] Brent Cassity: changer. And I think, you know, you can put prison on all kinds of different lines. You have people who have health crisis and there’s people who lose their job. People who have bad marriages there kind of goes along a line of. Relativity. Right. How does that affect you and your life? Prison’s pretty devastating because you really do have to start over.

Well, I guess some people don’t. I mean, there’s some people I always would’ve figured out, but the most, the humbleness and what you go through, you definitely come out. The other thing I think you come out with a different perspective is, is you definitely don’t judge a book by its cover . [00:32:00] I met so many guys, Bob in prison, that were really thoughtful.

Caring, smart, really smart guys. And that is not something I would’ve ever have thought or said about people who went to prison because I didn’t know any different.

[00:32:17] Bob Wheeler: Right. Do you think you came out with more compassion or at least a little more empathy?

[00:32:22] Brent Cassity: Empathy is gigantically more of who I am because I can get down on so many different levels.

Understanding, you know, where people come from and their backgrounds and how they got there. Clearly different perspective too. I mean, when you kind of run into a wealthy world, your world gets smaller and smaller and. I think I would never want to wish what happened to me to happen, but I also think what happened to me makes me who I am today and who I am today is different than I was 10, 15 years ago before this happened.

So looking back on it. Wow. What a . [00:33:00] What a ride.

[00:33:01] Bob Wheeler: What a ride. . I wouldn’t have picked it. Interesting. Ride , . You know, sometimes the way it lands. Right.

[00:33:10] Brent Cassity: There was a story though. I was one to share with you, Bob, and it wasn’t my story. I wish it was my story, but is the story of the coffee bean where this guy, he’s a well known speaker, so he is Devin West and he was a football player in Texas.

Got tangled up in drugs and addiction and that he ended up in prison. He was getting in fights and hitting up in the hole, and he is had a really hard time doing his time, and this old man came up to him and he. Boy. He said, you’re not gonna make it in here if you keep doing it like you are. He said, this place is kinda like a boiling water, boiling pot of water.

I said, okay. He said, so, he said, if I put an egg in that water, he says, what’s the water do to the egg? And he said, well, makes it hard. He said, we can’t get hard in here. He said, you can’t lose your heart. He should not put a carrot in there. He says, what’s that? Do the charities and. Yep. Can get soft in here, is that people take advantage of it.

And he said, I put a coffee beam in that water. [00:34:00] He said, what’s the coffee beam doing to the water? You know, I’m not following you. You said that coffee beam changes the water, the coffee. He said, that’s what you gotta do. You gotta be the change in here. And I thought about that story and what an important way to look at.

How you tackle life, how you tackle business, how you tackle money. Don’t let that change you. You change it. Yeah. And from that point forward, he took a different stance on how he was looking at things. But I always love that story though. I think that’s be the coffee babe. Be

[00:34:30] Bob Wheeler: the Coffee Bean. I love that story.

I had not heard that. And yeah, that’s a great story. Love it. Thank you for sharing that. Well, Brent, we are at the fast five, so we’re gonna shift the energy a little bit. Yeah. I so appreciate everything you’ve shared. We’re at the Fast Five. The Fast Five is sponsored by Fam Zoo, preparing Kids for the Financial Jungle.

Prepaid Cards in a family finance app for kids, teens, and. Keep your kids on a budget. Track chores, automate allowances, and encourage savings. If you want your kid to learn more money, habits that match your values, [00:35:00] sign up for Fam Zoo. To learn more, check out the link in the show notes. All right, we’re gonna jump in, have a little bit of fun, some of it.

Let’s do it. All right. This one might not be so fun, but what was the biggest thing that you missed from your old life when you were in prison?

[00:35:12] Brent Cassity: Mm. having a TV clicker you, you couldn’t turn the channel in prison. ,

[00:35:23] Bob Wheeler: I guess it was majority wins. I couldn’t

[00:35:25] Brent Cassity: wait to give back. I couldn’t wait Bob to give back.

And my kids even joke about it today. Don’t take the clicker from Dad . You just had to watch what was on the guy that had the seniority. He had the click. He got to pick . Oh man. I know there were other things, but that popped to my . That

[00:35:42] Bob Wheeler: is too funny. How much was your country club membership prior to going to prison

[00:35:49] Brent Cassity: Well, it cost me $80,000 to join and I probably spent five, $10,000 a month. So it was a nice country club. It was a

[00:35:59] Bob Wheeler: nice [00:36:00] country club. How do you feel when you think about your bank account? What comes.

[00:36:05] Brent Cassity: Not enough . I need more. Doesn’t have

[00:36:10] Bob Wheeler: enough zeros. Doesn’t have enough zeros. Absolutely. . When do you feel most at peace with your money?


[00:36:18] Brent Cassity: I think when I feel most of peace of my money where I’m putting it towards something that I really believe in, you know that I’m not wasting it. It’s really something that I’m terrible about buying shoes. So what? , I’ve got an obsession. I never have lost that, but I feel good about my money when I know I’ve put it towards something and I like even to today, if I can do something for my daughters or something, I’d love to do that now.

That’s awesome.

[00:36:40] Bob Wheeler: What emotion do you experience most around. I would

[00:36:44] Brent Cassity: say money has a little bit of ptsd. T S D to me that I have a little anxiety with it. It doesn’t make me comfortable and it doesn’t make me uncomfortable, but I also feel a little bit of something like I’m gonna get T-boned. Yeah. ,

[00:36:59] Bob Wheeler: I hear you.

I [00:37:00] hear you. Oh man. Money, money, money,

[00:37:03] Brent Cassity: money, money, money. That’s what it’s all about. .

[00:37:05] Bob Wheeler: Speaking of money, we’re at the sweet spot of m and ms. Money and motivation. Do you have a practical financial tip or a piece of wealth wisdom, something that served you before, during, after the Leavenworth stint.

[00:37:19] Brent Cassity: Yeah. The one thing that I think is important is, if anybody’s listening out there is don’t be afraid to step out of your comfort zone, because with money, it involves risk for you to be able to get to where you want to be.

Don’t be afraid of the mistakes. Don’t be afraid of the failures. But if you step and you take another step, You will become more confident and the only way you become more confident is step out of your comfort zone. If you don’t, you know these ugly routines that you get into become the warden of your freedom.

And that is not something that you want because you always have regrets with that. Money, jobs, opportunities. So my biggest thing is, is it’s even made me more like this Bob, [00:38:00] as I’ve gotten out, is I don’t wanna waste any time. I don’t wanna waste an opportu. And I feel like if it’s there and I can do it, I’m not waiting for the right time either.

I’m not waiting for something to happen. I want it to happen because I feel like it, that I need to go do that. That’s what you’ve gotta do. However you live your life. Find your passion, take your steps, and it’s gonna be uncomfortable, but you’ll get there.

[00:38:22] Bob Wheeler: Absolutely. I think that’s so true for many people in our minds, the moving forward, the fear of that is bigger than the reality of it.

So move forward, scared, , move forward, uncomfortable,

[00:38:34] Brent Cassity: move forward, scared, and I can tell people this so confidently. Nothing is ever as bad as your mind makes it out to be, not even prison. So just go ahead and do it because it won’t be as bad as you think. Yeah, absolutely.

[00:38:45] Bob Wheeler: No, I so appreciate it. Well, Brent, I think the through line for me about this whole conversation has been the piece around humility.

Because the more we can be humble, the more I think we can be open to what’s out there. Yeah. And not think [00:39:00] that we’ve always got it done perfectly right. Like that. There’s always more to learn and the curiosity piece, right? This piece about saying, how are they doing that? How can I do that better? How can I make an impact?

And not letting yourself become the victim in all of. It would be so easy to say, well, the government, they added this extra rule and they were, yeah, okay. They did. Yeah. This is what happened. They did these things and here I am. Yeah. And I’m not a victim. And I think that’s inspiring that even using your daughters as the motivation to say, I’m gonna win this one.

It may not look pretty on paper completely, but I’m gonna win this and I’m gonna come back. And I think that’s the piece that’s really inspir. Is to say, yeah, it all happened not making your dad bad and wrong cuz he had that conviction prior, right? Yeah. It’s just taking it all in and just saying, wow, okay.

Not the right, I would’ve picked not the one , but it’s the right I got. Yeah. And I’m gonna take it and learn from that. And I think. All of us could learn to have a [00:40:00] little more empathy and be empathetic. And so that takeaway of really seeing people in a different light, because most of us don’t have to wonder what people are like in prison cuz we haven’t had to go there.

Exactly. And so we don’t even actually know what the truth of all that is. So I just appreciate your transparency. I appreciate you just laying it out there because it probably doesn’t present well for some families. to have to name all these things and Dad’s outta town working part-time, right. , it’s, uh,

It’s rough. Yeah, so I so appreciate it. Where can people find out more about you? Where can they find out about the book, your podcast, all

[00:40:36] Brent Cassity: that good stuff? Okay, so the book, you can get it at Amazon Bars and Noble Walmart, nightmare Success, loyalty, betrayal, life Behind Bars, adapting Finally Break and. And my podcast is Nightmare Success in Out What Happens When Your Worst Fear becomes Your Reality.

That’s on everywhere. Spotify, Amazon, music, apple, all that on Instagram. I’m AB Brent Cassidy, YouTube, Brent Cassy, nightmare [00:41:00] Success, and Facebook on Brent Cassidy and my website. I mean, you can find out a lot of bears broadcasty.com. Cassidy is spelled. It’s spelled with a T instead of a D. I’m not with Sean and David as much as I would like to have been when I was a kid.

They had the great hair and the whole deal, but no, I’m not done .

[00:41:17] Bob Wheeler: Well, we’ll make sure we spell it right in the show notes. So , I so appreciate it. Well, thank you again so much. This has just been such an awesome conversation and I just appreciate everything. Thank you. I really

[00:41:29] Brent Cassity: appreciate it, Bob, and really enjoy your podcast.


[00:41:39] Bob Wheeler: We hope you enjoyed this episode. Did you learn something new about your relationship to money today? Maybe you have a friend who has some financial blocks or beliefs that are holding them back. Please share this podcast so they too can get off the rollercoaster Ride of Financial Fears and journey towards financial.

To learn how to have a healthy relationship with money, visit the money [00:42:00] nerve.com. That’s nerve not nerd. We’ll be back next week with another perspective on money and the emotions that bind us.