AARON SMITH, FROM FREEDOM 2 FINANCIAL FREEDOM

AARON SMITH, FROM FREEDOM 2 FINANCIAL FREEDOM


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Lesson Plan
In the video "From Freedom 2 Financial Freedom" featuring Aaron Smith, co-founder and co-CEO of Stretch, a financial services company, discussing his journey as an entrepreneur after prison. The video transcript reveals that Aaron's time in prison allowed him to reflect on his life, learn about investing, and manage his money wisely. While in prison, he read The Wall Street Journal daily, networked with other investors, and took courses on finance and economics. He also developed good money management habits, such as budgeting and saving.
Objective
The objective of From Freedom 2 Financial Freedom is to listen to Aaron Smith's story of entrepreneurship after prison, discuss the importance of mindset in achieving financial freedom, analyze the role of networking in career development, and reflect on the impact of Aaron's experience on personal financial goals.
Group Discussion Questions

  • Listen to Aaron Smith's story of entrepreneurship after prison
  • Discuss the importance of mindset in achieving financial freedom
  • Analyze the role of networking in career development
  • Reflect on the impact of Aaron's experience on personal financial goals
Introduction
The document provides a lesson plan featuring Aaron Smith, co-founder and co-CEO of Stretch, a financial services company, discussing his journey as an entrepreneur after prison. The introduction sets the context for the episode, which is sponsored by Stretch, and introduces the host and guest. The selected text is the introduction section of the document.
Feature Video

FROM FREEDOM 2 FINANCIAL FREEDOM

https://youtu.be/xjZzG6-ggUw

This transcript was generated by an AI and may not be entirely accurate or free from errors.

Transcripts
(00:00)
Hear the stories of men and women switching hustles and escaping the odds through entrepreneurship after prison. Not only will these stories inspire you, but also unlock business tips for financial freedom.
(00:11)
Let's get it. Welcome to Escaping the Odds special episode sponsored by Stretch, and I'll explain a little bit who Stretch is, but you got Aaron Smith here in Dallas, Texas wow. Not in Chicago for once and in person, which is also quite cool during these turbulent times of the pandemic still.
(00:37)
So it's truly a pleasure to have you here in Dallas visiting us and doing this episode together. Aaron absolutely. Thank you a little bit. About me. I'm co founder and co CEO of Stretch. We are a financial services company helping formally incarcerated people get free banking services and find work fast.
(00:56)
I like that you know how important that is. Very honored to partnering up with you to talk about money, which is a bit of a different nuance to what you typically talk about entrepreneurship and having entrepreneurs as guests, but this is the so called money tracks, and the tables have turned.
(01:14)
So I get the chance to interview you for once and have a conversation so your listeners and audience can actually learn about you, what was your path to get to who you are today. Thank you for the opportunity for allowing me to do that.
(01:28)
So I want to start off a little bit about your background. If you can talk to us about when you got out and how many years you serve th and how was it when you first walked out of those gates on the first kind of, like, few days, few weeks out of the prison.
(01:47)
I would love to hear how your emotions were and how the world looked like to you. Yeah. You're taking me back, right? Those emotions are kind of coming back to me, reflecting a bit. Absolutely. Yeah.
(01:59)
Incarcerated for? I was sentenced to twelve years in federal prison. We'll go back a little bit further than that. I born and raised on the South Side of Chicago, always had this entrepreneurial spirit, always value education, my household value education.
(02:12)
However, I grew up in the city of Chicago, right? South Side, gangs, drugs, you name it, right. So that was around me. So as I look back, that influenced me. Right. Most of the people that were around me were involved in some kind of drug gang culture.
(02:26)
Yeah. Friends, family. Right. Close relatives. So that led me down that path to that whole drug culture. Not as a user, but I looked at it as just another product. Right. Although it was illegal, it was a way for me to make money, but also value education, too, at the same time.
(02:41)
So I knew that I would go to college and become this successful businessman, and so the drug trade for me was a way to get in and get out, so I thought right. But then I became addicted to the lifestyle and addicted to the money that came in, just as the addict or the user was addicted to the drugs that I was selling.
(02:58)
And so that eventually led to your Sub also use as well? No, I smoked marijuana every now and then, but like, drugs wasn't right. I think in our culture, like, where I grew up, like, the crack epidemic and the heroin epidemic was so big, we seen so many people that kind of succumbed to that, where I knew that, oh, drugs, that's not my thing, right.
(03:18)
Although I'll sell it, so it didn't make sense. But at the time, my mom was walking, so that's where I was at. So it led to that twelve year federal census as a first time offender myself and like 47 other people for a heroin operation in Chicago housing project.
(03:33)
And so that really changed definitely the trajectory of my life. Right. How old were you then? I was 25 when I got indicted and I was on bond. I went to prison when I was 27. I came home when I was like 37, so about nine and a half years of incarceration.
(03:50)
But that time away really got me back to the essence of who I was. I was just. Was this cool kid. You know what I mean? I was an entrepreneur, right? I wasn't driven, motivated. Right. Ambitious, right?
(04:02)
And my ambition just led me down the wrong path, and I got stuck in the game. I got stuck in the monies that we were making, and I didn't really see anything else for me to do, right? This was easy, and I was good at it, quote unquote.
(04:13)
Right. Not good enough not to get caught, but I was nevertheless, I was good at it. I did my job, quote, unquote, where I was innovative, right? And so, again, I didn't look at selling drugs as it was illegal because everybody was doing it, right?
(04:29)
And it was just so smooth, like the operation, everything couldn't go wrong, right? So I got arrogant. And so eventually, of course, I got caught. But while I was away, I got back to who I was to learn to dream again and got in my word, got my faith together in God.
(04:47)
And that really kind of helped change my life. But while I was away, I met so many great men, right? Great men of business and just character in general. And I learned business from another level because I had the opportunity to be mentored by a lot of white collar offenders that I was incarcerated with.
(05:05)
And so it allowed me to start thinking about money differently and my relationship to money and also business differently as well, too. So before we go into that inside prison, how you started shifting your mindset about money and maybe your future, was it ever just about money?
(05:25)
When you did the drug operations, did you save up the money? Did you spend the money? How did you think about the money aspect of it? Or was it also you felt productive, you were, like, working and we're seeing results and the money was just the results?
(05:39)
That's an excellent question. It was both. Initially it was the money, but after a while, it was the lifestyle that kind of came with it. You were busy. I was busy, right. And I was productive, and I had a, quote, unquote, great product.
(05:51)
And so we looked at it as business, right? Like. Brand names and everything, you know what I mean? Clientele everything, like full operation. So it was just another product to sell. We packaged it out, we ship it out, and that's what it was.
(06:07)
But the money was just like a byproduct of that for me. And so I felt accomplished. Yeah. And that's the interesting part. You always go initially for, oh, I want to make some money. And once you make some of it, then kind of it shifts.
(06:22)
Yeah, for sure. Get some basics, and then you get sort of the gist out of productive. And I'm good at this. Yeah. And you get greed. And I could have left the quote unquote game a long time ago, had enough money to do so, but it's like, why leave?
(06:36)
This is so easy. It's a hands off approach, operations running, hey, I can just sit back and collect. And so the Feds had another idea for me. Well, it got stopped. You went into prison. Yeah. Now, I want to understand those nine and a half years in prison.
(06:53)
Obviously, there is a period of time where you got to get used to this new environment. Absolutely. Quite an adjustment. All the constraints and good people, bad people get to meet them all. How did you start thinking about your future, specifically, once I come out, how do I get my life back on track financially?
(07:12)
Because I'm sure there is a lot of reflection, a lot of planning that already starts inside the prison walls. Yeah. Well, I always had a money mindset just getting in the wrong way. And so when I went to prison, I started preparing for my release day one.
(07:28)
Oh, wow. I was looking for the exit on day one. Now, mind you, I had spent a couple of years on bonds, so I had the opportunity to kind of change my mindset that and really know that I'm going in the wrong direction, even though I know I'm going to prison for a long time.
(07:40)
And so that was a whole nother thing to wrap my mind around. But once I was inside of prison, I said, okay, I have to work on myself, both all aspects of my life, spiritually, mentally, physically, emotionally.
(07:53)
Every day, I did something right to kind of help kind of train this new behavior that I wanted to be kind of create. And so even the environment kind of helped me do that. Like the men that I was around, I did not spend time with people that reminded me of anything that I came from.
(08:11)
Meaning, like, that whole illegal mindset. If you were talking about anything illegal, I got away from you, right, because I couldn't be influenced again. I had to be influenced by people that I wanted to emulate or at least take on their mindset.
(08:28)
And so I spent time around people. That were like, you naturally had that because it seems to me some people like, you come in and they immediately switch their mindset, and some it takes a while down that rabbit hole and don't come out of it very easily.
(08:41)
Yeah. And no doubt, like, I had my times where I wasn't always just like, straight and arrow in there, where I just like, you're going to slip up and fall. But for the most part, I was really planning to come home a better person and to think about money differently.
(08:59)
I went from a savings mindset like, okay, stack up all this money, right, to a mindset of, okay, I have to learn how to invest my money, not only make it, but also make my money grow for me. And so that's when I got into reading The Wall Street Journal every day, like, faithfully every day.
(09:20)
So that's why I say the environment was part of it was conducive for my growth. Because the prison I was located in, Minnesota Federal Prison, they had a lot of programs there, so it was considered like a program you are and so if you wanted to do better, you could do better, right?
(09:36)
Unlike some other prisons where you had, like, a whole lot of distractions. And not saying that it wasn't distractions there, because it was, but I just chose to kind of I found my lane, and I ran in it.
(09:45)
Right? And they had resources, and they had some resources there. Right. And then my resources were informal. I will meet people, and I will find out that this person was a white collar offender. Like, oh wow, okay, I need to pull up on him.
(09:59)
I need to pick his brain. And so that was my education, being around people like that and really grown me for the success that I'm having now because I prepared for it back there. I networked while I was in prison.
(10:11)
And so, as I was saying earlier, I read the Wall Street Journal every day. I learned about different aspects of the financial markets, stock options. I started charting the S and P 500. So I really immersed myself in the financial industry market, just learned everything I could about you.
(10:30)
Met a lot of people also inside prison who actually knew a lot about economics, money. Oh, wow. Absolutely. It was school all over for me. I've always been a learner. So they would teach classes about stocks, teach classes about real estate, you name it.
(10:46)
Economics from practitioners, from people that actually did it in real life. And so this is all more efficient. Than reading about it for years. Like, 20 minutes from someone who's the master of it. There you go.
(10:57)
Now I was able to take what I was reading in The Wall Street Journal and have a real conversation with an investment banker and say, okay, how true is this? What's to this? And then they took a liking it to me.
(11:09)
So we kind of built that relationship. And I really grew from a financial standpoint to the point now where I could trade in the market. Right. I can trade options, and I can be okay doing that and be well equipped, because I learned this stuff while I was away.
(11:26)
I prepared for it. So it wasn't like overnight I watched yeah, I was yeah, wasn't like a YouTube video. Not saying you can't learn from YouTube video, but this was like years in the making. Like, I was been waiting on this moment for nine years to actually do some of the things that I'm doing now.
(11:42)
So inside prison, how was your money management there? Did you have a strict budget, I understand. Families send money to their loved ones inside prison because everything costs money in prison, too.
(11:54)
What was your budget? Did you always use up your entire allowance per month or you actually saved? I would love to understand how you manage money inside prison. Oh, for sure. I think the way you money manage while you away is going to be pretty much predictable, what you want to do once you get out.
(12:11)
Powerful. Yeah, pretty much budget, like, we can spend. I believe at the time, it was $360 per month right. In your commissary. So that was like your that was. The balance you were legally allowed to have.
(12:25)
There you go. And I'm glad you said legally, because you could find ways to kind of go over your spending limit and still get other stuff in. Right. Stayed away from that. Yes, I stayed away from that.
(12:32)
Right. Plus, I had no need to try to spend 500, $600 per month. And so I budgeted my money like you would get a commissary sheet. Right. And this is a good practice for people to kind of continue to have once they get out of prison.
(12:46)
I will get a commissary sheet, and you know exactly how much you're going to spend. There's no going up to the counter like, oh, I don't have enough money for that. You know what I mean? So, you know, you're calculating to the cent how much this food commissary is going to cost you, and you know that you have that on your account already.
(13:05)
You're not going to walk up to the counter and not have the money in there because you're going to hold you can't overdraft there's no thing. So all these habits are kind of good to kind of keep up. Well, there is credit there.
(13:18)
Okay. I'll touch on that. Right? Yeah. Keep it in your thought out. Okay, cool. All right. So pretty much my management. I made sure that I stayed on, but I got, like $120 per month for my job, and I was, like, penitentiary rich.
(13:31)
Right. I had one of the most coveted jobs in prison I worked for, like truelinks. Which is like, the computer system. So I wiped down the computers, changed the cords and stuff. I was like, the lead in that.
(13:41)
Right. Got $120 a month. Easy money. Sweet. Right? Plus, I had a little money coming in, so probably about. 300 per month coming in, which is like, I was okay. And I didn't spend the whole $300 per month.
(13:54)
I would probably spend the phone at like $25 per month. You only got 300 minutes per month. So you have to learn how to budget your minutes as well, which is family members, right? So you get 15 minutes to call.
(14:08)
So I know, like, okay, I'm going to talk this person for seven minutes, talk this person for eight minutes. So learn how that's budgeting as well. And that's some of the things I would talk to the guys about, because I taught money management and budgeting while I was away inside.
(14:20)
And so like, hey, we're already doing this. We're already budgeting ourselves, right? We budget our menace. We budget our money. So we have to keep that mindset once we release. And so I did that. And so that kind of kept me with a habit, and I saved money.
(14:34)
The system allowed for you to save X amount of dollars, either per percentage or a round number that you wanted to kind of put to the side within the system to save your money. So if you had $300 coming in, you could say, okay, I want 30% of that to go into this commissary trust fund for yourself.
(14:51)
So when you leave, you have this money. And so that was one of the things I did. And so I was able to save up, which was a lot to me, but like $50 a month. And sometimes I would dip into it during Christmas time or whatever, but for the most part, I stay consistent with it.
(15:04)
And that's key being consistent in anything, especially like budgeting and saving. And so when I got out, I think I had around, I want to say, $1,100, and I was like, that was an accomplishment for me because I took a few years to save that up, you know what I mean?
(15:19)
And so I was like, okay, cool. I know if I can do this in there with a little bit, imagine what I can do with a lot. Because it doesn't matter the amount of money. It's just like that habit is the. Habit and the behavior.
(15:30)
It doesn't matter if you're making 300 or 3000. If you cannot put away $10 from $320, you're not going to put away money from 3000. You hit a dead on the head. So I do that, and I want to create these good habits and structure and routine and.
(15:48)
I extracted from prison. You know what I mean? I use prison as a training ground for myself. It wasn't like, Woe was me, I did the crime. Okay, man, it is what it is. Let me go ahead and knock this out and make the best of it.
(16:01)
There's no doubt. I had time. I was like, wow, I could be doing something else. But you accepted your situation. I accepted the situation where the difference comes in, where a lot of people have a hard time accepting that situation in the current moment time, and they're just fighting it and fighting it and not giving in and rather focusing on the future where it seems right away you accepted it and decided to look towards the future.
(16:24)
No, absolutely. And I think when you mentioned fighting, if you have a situation where you feel like it's unjust, I'm an advocate for, like, hey, look, fight for your freedom and not give up, but also at the same time, well, while you're doing that, continue to prepare for your release.
(16:41)
Make the best out of the situation. Like, if the worst case scenario comes, you have to do that time. You have to do that time. So I believe just early on, starting that bit off and like, okay, this is what I want to accomplish.
(16:53)
This is what I want my life to look like when I get out. And so I finally got out, and that was a whole lot of anxiety. Wow. Before we walk out of the gates, what is credit in prison? Oh, yeah. Well, credit in prison is like, ego.
(17:07)
Is it kind of behind the doors? Yes, it's behind the door, but it's part of the culture, right. People will run, like, stores, right? Like, for instance, you only go to Commissary, at least where I was at, like, once a week.
(17:21)
And in most places, you have a certain date when you go to Commissary. So in the meantime, between time, people run out of goods. So someone like myself, like, okay, I see opportunity there. There's a gap.
(17:32)
Okay, cool. Let me buy more. Let me open up this grocery store. Wow. And I can sell this snicker bar. If it cost me $0.85. I'm going to charge you $0.85 plus stamp. Right? And the stamp was like our form of currency inside, right?
(17:50)
Or it could be anything like stamp for letters. A stamp for letters, right? Because you could turn that in, it was money, right. Or you can use other goods that's like really popular in prison. It may be like a macro or soup, right, that was considered like a form of currency, right?
(18:05)
Like all in the old days, like bartering services. Like there's no cash. That's how money started getting invented in the old days. Days. And there you go, exchange, right? So it's all about that value, whatever the next person feel like that was valuable to them.
(18:16)
And so a person will have a store and then they may run up a bill again. That's bad money management, though, right? You're going to run up this debt with this person and now you can't pay it. And so now it creates problems for you.
(18:27)
Now you have to check in or go in the hole because now you got this $500 debt that you ran up for the month because you had bad money management. So even doing things, things like that, again, it's not conducive to a profession to proper your relationship with money once you get out.
(18:42)
Because if you're doing it in there, chances are you're going to do it when you get out with credit cards or whatever, right? So just making sure a person kind of stay away from those kind of vices and things and not saying I would go to the store at times, right?
(18:53)
Like, say it was like a sudden meal I had to maybe create for my birthday or something like that. I would go to the store, but I will immediately pay it back. I didn't rack up no crazy bills, right? And I had a hustle when I was in there as well, right?
(19:05)
At one point in time, I was like selling onions, right? Because I know people need onions, so I would just sell onions for a couple of Samsung piece. So that was like my little side hustle money, right?
(19:14)
And it kind of kept the entrepreneurial juices still flowing in me for sure, the business mindset. To different things. So just being able to just switch hustles and do something legal, like I said, it was good practice for me.
(19:32)
Very cool. So then nine and a half years later, yeah, you're walking out of those gates, you have close to $1,100 in. Savings, something like that. Walking out with. Feeling those first few days you're walking out?
(19:48)
How did you think? I'm sure there's so much going on in you. Things you have a plan, things you want to do right away versus longer term goals. But I just would like to understand what are the first few things you did right away, and how did you start thinking about, okay, I need to make money, but there's also spent involved here and there, paying for things.
(20:08)
Talk me a little bit about how you're was in those first few days. Well, I'll talk about the first few hours first. Right. That was probably, like, the most freedom that I had felt during probably the first six months after my release.
(20:21)
So I was released on a Friday, had an all white, and I was really intentional because I was like, this new being. I wanted to be, like, fresh and new. So I had my buddy Rashid. I'm like, Abraham, I need you to send me all white.
(20:33)
All white, everything, right? I'm starting over. Fresh pants, pants, shirt, everything. I felt like a million bucks. Seems like a Mexican wedding. Yeah. So I got out, caught the bus, and everything was just so new and fresh to me.
(20:45)
It's like I had walked out these gates in nine years. Even seeing cars on the highway, I'm like, I'm taking in everything. Wow. It was, like, overwhelming, too, at the same time. But I'm trying to be cool.
(20:58)
Right. A lot had changed. A lot of change. Right. And especially once I got back to Chicago, I was, like, just anticipating it. And so I took the butt. No, I'm walking through Minneapolis because that's why the bus came into I was in Minnesota, so I had a layover for like 6 hours, and I'm just like, what I want to do with this time?
(21:17)
So I'm just walking around downtown Minneapolis and just kind of, like, taking it all in. I sat down, think I ate me. Um, I think I ate, like, some buffalo wings from a rooftop bar. I even tip the lady.
(21:30)
So everyone on their smartphones said, bad. Yeah, everybody is with their heads down. You know what I mean? I find myself doing the same thing now. Right. So that habit, right? Everybody's kind of walking, and they're not paying attention to whatever right in their phone.
(21:42)
When I left, smartphones weren't. Really around. And so I'm in a restaurant. I'm eating. I'm feeling good. I even tipped the lady, like, $20, right? I'm like, wow, I'm just balling, right? I'm just feeling good.
(21:54)
I'm feeling good. You know what I mean? So I'm like, hey, look, let me make your day. Like, this is the best day of my life, so I want to kind of share that experience with somebody. And so just kind of taking it all in.
(22:05)
I left there, just kind of walked around. I went shopping, I don't think, went to Nordstrom Rack, bought me a pair of coal. Hans right? Were you modest, or you kind of went for oh, I was still mod wanted this brand.
(22:17)
Yeah, well, I wore that brand when I was out previously, and so when I walked in the store, and I said, let me get those, and so I bought them, treated myself, right? Treated myself like, okay, cool.
(22:30)
And so did that. Finally get on the bus, and I get home, and I had to report to the halfway house by a certain time, and so I'm really kind of, like, anxious about that because I don't want to show up late.
(22:42)
I want anything to happen that can jeopardize me potentially going back to prison. And so I made to the halfway house, and that's where the shock hit me. It was like, oh, you have to have an ankle monitor on.
(22:55)
You didn't know about that ankle monitor? Why? I'm not like, this threat. I just sold drugs, right? It was like, well, for some reason, the Bureau of Prisons felt like you're a safety risk. That was one of your parole conditions.
(23:09)
The federal system doesn't have parole, okay? So I got to the halfway house. They slapped his ankle monitor on me, and I'm like, wow, I was back in prison. Like, for real. I was saying to myself, like, you know what?
(23:23)
They can just send me back because I had a routine while I was in prison. I knew what I was going to do on a Wednesday at 02:00 P.m.. I don't know what my life is going to be like now for these next six months while I'm in this halfway house.
(23:34)
So they could just send me back, even though I didn't tell them that. But in the back of my mind, you have these self thoughts. It's like. Yeah, at least time will go back quick for me. I get out, and I'll be totally fully free, because I'm not fully free now as I expect it to be.
(23:49)
And so they're like, okay, you can't go here, you can't go there. You have to be with us every week. You have to give us a schedule to let us know where you're going to be going. You get, like, an hour free time once a week.
(24:01)
You only go to these designated areas. I'm like, oh, my God. I remember all those things. It was so it was more restricted when I was in prison, and so then I couldn't do some of the things that I wanted to do right.
(24:13)
Not anything nefarious. I just wanted to kick it. I wanted to go see this or see that or whatever. So I had to only go from A to B, b to C. Like there's no deviating. If you did potentially be sent back, that's the last place I wanted to go.
(24:27)
And so I had to learn to even shift my perspective as I looked at that, like, okay, all right, well, maybe this is a way for me to really stay focused, you know what I'm saying? So that's what I did.
(24:39)
I took that mindset that I had in prison, and I'm like, okay, I have to just kind of just focus and begin to get my credit right, look for a job, which I was going to do that anyway, but it really had me laser focused because I couldn't do anything else.
(24:51)
I couldn't. It's amazing that that knowledge was there, though, that I need to go build my at it. You had those things already listed up. Already, because when I came home, I had a list. I wish I had it with me today just to reflect on it.
(25:04)
It was a two list. Like, the first 30 days, what do you do? What do I need to get the first 90 days? What do I need to get within 180 days? What were those few things? I needed to get my ID. Didn't have a state ID.
(25:21)
That I needed to find a job or at least find some prospects on a job. Right. I also needed to make sure that I opened up a bank account. Right. I needed to pull did you have. A bank account before you went in, or you never had a bank account?
(25:38)
So I had a bank account while I was away. Maybe for like six months. It was a local bank that I was able to kind of set up a bank account with, but they ended up closing down. So I just used a commissary system inside a federal system to kind of save my money.
(25:53)
Right. Even though you could take it out when you want, just like a regular bank. It's the same problem we keep hearing as they open bank accounts, returning citizens. Some of them never had a bank account because of the nature of their activity.
(26:05)
There you go. Yeah. There's no need mistrust towards financial institutions and fees and charges. Yes, others had, but they, over the time when they were in prison were withdrawn because some of their subscriptions and services never got canceled.
(26:17)
And then the bank shut them down, basically. So I was able to open up this bank account. That was one thing I did. And I was like, okay, I have to get in some kind of a program to kind of be around the people that I was just around while I was away.
(26:32)
Right. Because I got so used to being around productive people. You wish you had stretch around. There you go. Right. And so I was able to find a bank to kind of work with, do a program. And so that was like my 1st 30 days that I had to do.
(26:44)
I think I got a job within the first 45 days because you didn't have any movement while you were in the halfway house. Because for the first two weeks, you have to go through all these different orientations.
(26:57)
So you're not leaving, at least while I was there. You're not leaving for the first two weeks. So get used to it. That part of it. You can't really do interviews either. Yeah, you really can't do a lot of stuff.
(27:07)
And this is pre pandemic. I can imagine what it's like now. That was my 1st 30 days. Was it a fair chance employer or just somebody who no necessarily was, but took a chance on you? They took a chance on me, like I sold myself was.
(27:21)
I like to say I was prepared, and I was prepared to tell my story too. I didn't kind of sway from it. I was straight up front. You applied Haphazardly or you knew you were going to go there. That was part of my 30 day plan.
(27:35)
I knew that I was going to work in logistics, and I knew I need to work Thursday. I was very specific. My plan. This is what the audience needs to hear. Like, you have to be specific, right? I was like, okay, I'm going to find a job in logistics.
(27:47)
I'm going to be a dispatcher. Because that was a little bit of experience I had before I was incarcerated. I was like, okay, that's a job that I know I can do. Right? Even though I got these entrepreneurial dreams, I need to find something I know I can do that I'm going to stick with until my entrepreneurial dreams kind of get off the ground.
(28:03)
I can fire that job. So is a factor how much you would get paid? Absolutely, for sure. I knew I needed to make $17 an hour, and I kind of came up under that. I started making like 16,000 an hour. Right?
(28:15)
But I said, I need to work third shift as well. I was like, I need my daytime to do the other things I want to do. And so I've been working third shift at a logistics freight broker since I came home.
(28:27)
And that has spawned into me starting my own trucking company, Uturn Transport, along with Escaping Odds podcast, like giving guys opportunities to have their own trucking company that's formally incarcerated.
(28:40)
So I'm happy to talk about that too. That's very cool. So getting that first job in a matter of 40 something days, a little over 40 days, we know in the industry, actually for a lot of people. It can take months yes.
(28:51)
Until they secure that first job. How inefficient it is because they don't know if the employer actually hires formally incarcerated or if they do. For my record. Right. These are, I think, the things that now are getting better because more fair chance employers are actually looking at this workforce and giving them a fair chance.
(29:09)
What we do, for example, is stretch partner up with honest jobs is individuals who come out, they can provide their conviction history and the opportunities they see is truly tailored. It towards their conviction history.
(29:22)
That means the job is open to them so you don't get these nasty surprises. Submit a resume, go through interviews, and then once a background check is done, then you hear the no. Okay. But I think it's still a very good record getting that first job in 40 days.
(29:38)
I would say 40 plus days, like, maybe under 50, but it was definitely under 60 days. 60 days? 2045. So you worked the first two weeks or first month, get that first paycheck. How did you feel getting that first paycheck?
(29:50)
Wow, felt like happy or more worried? No, I was happy because now I was like, okay. One of the main things a person is concerned about when they leave prison, at least for myself, and basically just like a job and want to make some money, and they want to have a place to stay, and they want a girlfriend.
(30:08)
Right. But the third thing wait, basics, right? Yes. That's the basics, though, right? You know what I mean? Company too, right? Yeah, they want a companionship. Right. But those first two things, that job and that place to stay, that's key.
(30:23)
I was concerned halfway house was just transitional. It was transitional. Like, one day you got to leave there and it's like, okay, I was willing to work anywhere. I was applying for almost applying.
(30:34)
I don't think I did it for, like, a manufacturing, labor intensive job, but I knew I wasn't going to stay that long. I was just like a job to get a better job, to get my career, which is entrepreneurship.
(30:45)
But I knew I had to find my way and work my way into it. Like steps. No? Yeah, I've got paychecks before. Yeah, but that was the first paycheck that I had gotten in the outside world in a long time. And so I got it, and I think I had to rec.
(31:08)
Yeah, I had to rectify it at the time. And so I'm like, wow, okay, what am I going to do? My expenses were really low because I was in a halfway house, but I had a door order, and so I was just really generous, you know what I mean?
(31:22)
I'm like, okay, they need this more than I need it. Like, me and my daughter mom, my daughter, right? So I had everything paid for me. I still had three hots in a cot, right. My cell phone bill. My buddy was paying that for me while I was incarcerated.
(31:36)
So I can get on my feet. So I had no expenses. So again, I started saving money because I knew, I'm coming out this halfway out soon, and I know that I won't immediately get into my own place because I had support of family.
(31:49)
Hey, you can stay with me until you get on your feet. And so I'm like, okay. I knew I didn't have to worry about an apartment right away for which. You typically need to put a secured deposit down, right?
(32:01)
Absolutely. Yeah. And in Chicago, I think it's like, double. How was transportation for you? Did you car public? Transportation? Transportation. Luckily, I live in Chicago, probably one of the best transit systems in the world.
(32:13)
Yeah. So I use that for a while. I wasn't even too bus, subway, buses. I wasn't too gun hole on getting a car because I knew that was an expense. I knew that, okay, if I got a car, you need insurance, I need insurance.
(32:27)
And I definitely didn't want to get a car note right away because I was again building my credit up, and I was like, okay, I need to kind of wait on that. And luckily, my brother, he was able to give me a car just to kind of get around with.
(32:40)
So I had a really great support network, and that's pivotal. Yeah, like, for a person to come home. So I had that so I didn't have to have a car. So I had this money saved up, and I was like, okay, cool.
(32:51)
This is what I want to save my money for, to get a property eventually and kind of start my entrepreneur endeavors. And so that's how I started. So I hear that already the longer term goals, I want to be able to rebuild my credit so I can afford a better auto loan and then get a proper car.
(33:07)
Right. Rather, right now, if I went, I would be overpaying. Overpaying. Absolutely. Lousy car anyways. Yes. Then I need housing, so I need some money for security. It to get my own place. Yeah. So did you have some goal in mind in terms of how much do I need to save up?
(33:23)
Were you saving towards, like 30 00 40 00 50 00 Was there a specific goal, or you were just saying as much as I can? No, it was a specific goal. Like, I wanted to save up within a year, like 15 grand.
(33:34)
15 grand? I need over a year. Yeah, over about a year. Right. 15 grand. And then, as I stated earlier, I had these aspirations to trade in the market, like to do option trading. So I was like, okay, I need a certain amount of money to kind of trade and do that.
(33:47)
That's just for that activity. That's for that activity. I knew that I wouldn't get a car note. That wasn't like, the first thing I wanted to do. And then my brother had gave me a car, so I was cool with that.
(33:57)
Just give me Ada BV vehicle. I'm not really trying to go get the flashy car eventually. That was the goal. Right. But it's like, I got my priority first, right? I want to be able to make necessity rather than necessity in desires.
(34:10)
Right. You know what I mean? I wanted to make sure that I had something else that was going to pay for that car note for that vehicle. Right. I wasn't going to turn that into, like, well, I'm stressing to make that car note.
(34:24)
So do you as you keep going in your daily life, in that phase, making money, saving away, finding, getting together with a woman, having a nice relationship, all these basics that we all need in our lives, did you kind of change your relationship to money, you think?
(34:43)
It seems like there was this behavior of, I want to collect and collect, but then was it also now towards specific goals that kind of creates more motivation, right, every day? Yeah, definitely. It went from saving to investing.
(34:58)
I wanted to make sure my money was making money for me because I knew that time was a commodity that we can't get back. And so I became really conscious of time, and I knew that I needed to make sure that if I had investments that was making money for me, passively income, then I could do all the things I wanted to do in life.
(35:25)
I can travel, I could spend time with my daughter. I didn't have to worry about punching that clock forever. And so that's like. Currently still my goal and having cushion. To absorb shocks, right? Absolutely.
(35:37)
Yeah. So it was more like it went from a savings mindset to an investment mindset. Like, okay, I need to learn how to make this money work for me. And so that's what I've been doing. So right now, fast forward.
(35:50)
You are working in logistics business. Your audience may or may not know. I know for sure. You're starting a trucking business, which is very admirable. You're really living your entrepreneurship now to the next level.
(36:01)
Yes. You're doing escaping the odds, which is kind of your creative side. So you got the real revenue generating streams in your life. You got the kind of like self indulgence and creative side when you think about money now, what is that goal for you?
(36:17)
So now you want to invest, you want to make your money put to work. Every month what you bring home, do you say 10% towards my investments and I'm going to keep putting that to work or is this the rest I want to save or spend?
(36:29)
I wonder how you kind of like organize it in your head and final guidance maybe for our audience of how you function. That could be a potential way for others. Yeah, for sure. Well, I got a couple of jobs that I work and basically I try to save like $1,000 a month, you know what I mean?
(36:49)
That's pretty much like a grand a month. And I just kind of I was saving up for an investment property eventually. The market like right now is not the best. So I was like, okay, how can I take this money that I have and again make it grow for me?
(37:05)
You don't just let it sit in a savings account. You actually invest. At first I was letting it sit in the savings account that I was saving up for this income property, but the market is not in the best time right now to buy the property.
(37:18)
So I'm like, okay, let me put this money in my Robin Hood account. And so that's what I've been doing. I've been selling options, which is a way where you can gain income off of your monies. So I've been doing that on the week to week and.
(37:32)
On top of that, I got the trucking company, which is allowing for me to kind of have even though it's in the beginning allows me to have some passive income, I don't have to be in a vehicle, actually joint venture with a buddy of mine who's formally incarcerated as well.
(37:46)
And that's the whole premise of Uturn transfer is to hire men and women who are formerly incarcerated to teach them how to have their own trucking company. So that allows me to have passive income that way as well, just so I can kind of do more of the things that I want to do and manage my time better.
(38:02)
So I'm getting to that point where I can have more passive income coming. In, more so than we call it the ultimate diversification. There are different paths to building financial wealth. One is I go get an amazing job in one company, make $100,000 a year.
(38:18)
If you don't have that yet, what are the other diversified streams that I can get into to still supplement? Absolutely. A full time job that I'm doing. I love that. Nowadays, I'm so excited about the different forms of income that a person can kind of generate.
(38:35)
Like toro airbnb. There's so many I'm always thinking Uber, DoorDash, I've done. DoorDash, I've done it all. You know what I mean? Just to kind of get me to a certain point where to supplement. To supplement.
(38:49)
Right. But at the end of the day, I'm always thinking passive income, right? Because I know passive income. Yeah, you have a goal, $1,000 to save. Right. But my number, as you asked about earlier, I would love to be able to make passively.
(39:05)
And I kind of battle with this number because I know that I've been around people that make way more and I have the capability to make way more. But I would say passively, 50 grand a month, that doesn't mean I'm going to spend 50 grand a month.
(39:18)
My lifestyle doesn't call for that at all. Right. No, I don't need the Ferrari. But if I wanted to get a Ferrari, I'm probably going to buy an investment that's going to pay for that Ferrari. It's never going to be from like, working earn income.
(39:30)
Like, to me, that doesn't make sense. Right. But I learned that in prison, right, from the people that were uber millionaires. Right. They was like, hey, you allow for your assets to pay for your liability.
(39:42)
So that's always my mindset. With that 50 grand a month, that's a nice number for me. Right. Am I going to spend 50 grand? No, I'll probably spend maybe ten grand per month. And that's with everything, right?
(39:54)
Like mortgages, the whole nine family, kids, travel. And so I always will have that cushion, and you better believe that 40,000 less leftover. I'll be investing. Knowing how ambitious and driven you are, I can guarantee you the 50K years ago was probably ten K.
(40:10)
It was. And I will have this on file. It's documented in five years. We're going to do a refresher of this same episode, and I will see what that 50K is and see what. It looks like, right? Yeah. But the thing is also to be able to kind of help others, right?
(40:22)
To be in a position like my ultimate goal is to be like this angel investor, right. So now I can invest in other people's ideas, right. Same way that people invest their time in me. I can say, okay, I like the idea.
(40:34)
I can connect you. Yeah. I connect the resources I've been able to gather and the money to say, okay, to be able to push your product or service and make your dream come true. And so that's like the ultimate goal for me.
(40:45)
Yeah. Like the next stretch founders, you could support them. Absolutely. That's what we got from our angels. One final bit before we say goodbye on this episode, which was such a fun, fun episode to do right here in Dallas.
(40:58)
What would you tell your younger self from three years ago? Or maybe others who are just coming out of the gates and starting the reentry? What is that one piece of advice you would tell them regarding their anxieties about money.
(41:10)
Oh, wow. Like, don't allow, like, money to consume your every thought, because when you allow for that to happen, you're probably going to do almost anything to get that money. Right. And that's what happened with me while I was on the streets.
(41:24)
There's probably one too many things that I wouldn't have done to Ascertain. Certain amount of money and get this money go. But now it's like I have a new perspective on it. Right. It's only a tool. Right?
(41:35)
Money is only a tool. Right? Just like when I was incarcerated, we didn't have money, but we value other things. Right. So make sure that you're placing the right proper value on money. Right. And understand this that price and value is two different things.
(41:51)
It's two different things. Thank you so much. Let's do this, and that. Okay. Great to have you here. Thank you. Thank you. Thank you. I appreciate it.

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