Failures Podcast
Failures Podcast is a raw, no-fluff self-development show for men navigating life without a manual.
Hosted by Rich and Justin, two lifelong friends with over 20 years of brotherhood, this podcast explores fatherhood, masculinity, legacy, discipline, regret, purpose, and generational healing through one unfiltered lens: failure.
Each week, they share real stories, hard lessons, and invisible influences that shaped who they’ve become, and how younger men can learn from it.
Whether you’re figuring out how to be a father, chasing financial freedom, trying to become more disciplined, or healing from the way you were raised, this show is for you.
We’re not gods. We’re not gurus.
Just two men who have lived, failed, grown, and learned the hard way so you don’t have to.
🎙️ New episodes every week
📲 Follow @FailuresMedia on all platforms
🧠 Join the movement: https://failuresmedia.com/subscribe
Failures Podcast
Why Failing in Your 20s Helps You Win in Your 30s
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You're approaching 30 and feel like you're falling behind in life. Your friends are getting married, buying houses, advancing in their careers, and making money while you're still trying to figure things out. Maybe you're broke, living at home, struggling with relationships, or wondering if you've wasted your 20s. But what if all those failures are exactly what you need to succeed in your 30s?
In this episode of Failures Podcast, Rich and Justin challenge the idea that men should have their lives figured out by 30. They unpack why so many men feel behind in life, how social media creates unrealistic expectations of success, and why the mistakes you make in your 20s can become your greatest advantages as you get older.
Rich shares how becoming a father at 24 with almost no savings made him believe his life was over, only to eventually buy his first home at 32. Justin opens up about accumulating over $70,000 in debt while trying to impress people in the music industry, chasing validation, and making financial decisions that nearly buried him. Together, they reflect on failed relationships, outgrowing friendships, career setbacks, and the painful lessons that helped them build confidence, financial stability, and a clearer sense of identity.
This conversation is about more than getting older. It's about understanding that personal growth takes time, that success isn't a race, and that feeling lost in your late 20s doesn't mean you'll stay lost forever. Your 30s aren't automatically better, but the experience you gain from failure can help you make smarter decisions about money, relationships, friendships, and your future.
If you're turning 30 and feeling behind in life, struggling to find your purpose, or comparing your progress to everyone around you, this episode is a reminder that your biggest mistakes don't have to define your future.
Your 20s gave you the lessons. Your 30s are where you find out if you actually learned them.
Failures Podcast 2026
We're not gods. We're not gurus.
Just two men in our 30s sharing what we’ve learned the hard way so you don’t have to.
🎙️ New episodes every week
📲 Follow @FailuresMedia on all platforms
🧠 Join the movement: https://linktr.ee/failuresmedia
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As you learn from the lessons and the mistakes that you've made that put you in a fucked up situation, this is a great opportunity to never make those mistakes again and change direction and learn from your mistakes. That's why life gets better. Because now you can start clearing the trail to get to where you always wanted to go. And that comes from learning from your past and learning from your 20s and learning from your 30s. Failures Podcast. Today we're talking about men feeling behind in their late 20s, going into their 30s. But the truth is, men actually start winning in their 30s. Don't believe me? That's fine. Stay tuned. Watch the episode. Rich and I are going to unpack embarrassing story after embarrassing story and lessons that we learned from our 20s that can prove to you that your 20s are nothing but a foundation for learning and improving. And you'll get the girl you want in your 30s. You'll get the money you think you deserve in your 30s, and you definitely get more experience because with that every ass whooping comes experience in your 30s. This episode is for the guy. Let's say he's pushing 28, pushing 29. He's kicking 30's door down. And he doesn't have the money he wants. He doesn't have the career that he wants. His friends are online. Some of them are even getting married, buying houses. Everyone that he follows on the internet is under 30 and they're making a lot of money. What is he doing wrong? And why the fuck would Rich and Justin make a podcast dedicated to telling him, slow down, man, you're not behind. You actually get better in your 30s. Men start winning in their 30s. Rich, when you were in your mid-20s, was there ever a moment where you genuinely thought to yourself, damn, I'm cooked. My life is done. This is who I'm going to be forever. And there's no way I can bounce back from this problem I'm having.
SPEAKER_01Yes, bro. I thought my whole 20s I was cooked, bro. I had a child at 24 years old, Juss. I was in my last year of Montclair State University. I barely had any savings. I had a bullshit job making like $35,000 a year. And I was about to have a child with a girl that I wasn't even with. My ex was pregnant. We weren't no longer together. And she was about to have a child while I was 24 years old. And I immediately thought to myself, like, my life is over. Like, I'm not going to finish college. I'm barely an adult. I have no savings. How am I going to provide for myself? Provide for my child? Am I even fit enough to be a good father, bro? Like I had all these negative thoughts just swirling in my head. And I just remember sulking in that moment, like, damn, I have ruined my life at 24 years old. Now, obviously, that's not what actually happened. But for that time period, just 24 years old, about to have a child, I thought that I just I ruined my life and there was no sort of like fixing it. Now, at 38, do you believe that when you think back and look back? Oh, absolutely not, bro. Like, that's the beautiful thing about hindsight. And that's the beautiful thing about being in your 30s, is that you could look back into your 20s and being like, oh, that's funny. I thought that was going to be the end of my life, but really it was just a change in my plans. And I think that's one of the biggest distinctions that we have to certainly unpack. It's like deviations to your life plan are okay. They're not the end of the world. And I think that's what happens to a lot of these young guys is they they've hit rock bottom. They have this impactful moment in their 20s, and they feel like, damn, this is the rest of my life. This is how things are going to play out for me. And what you really need to conceptualize is just like, no, man, this is a moment in time. This is just a moment in time. This failure, this mistake, this trials and tribulations, whatever you may be going through, it's just a moment in time. And things will get better. And I think over time, your 30s is proof that things do get better.
SPEAKER_00Yeah. And Rich, I have to say I was triggered, and the idea from this episode came from two places. One was a social post I read online. And it was a social post from a very sloppy social media account that it just like targets men and men for not being adequate or making enough money or not paying the most on a date or taking them to a $700,000 fucking home the first year they're together. Like all this bullshit you see online. But one post that I read, and it kind of triggered me, was is it just me or men are starting to peak in their 20s? And they fall off after the fall off is tragic. That was the post that I read. And it was just a whole bunch of people in the comment section debating whether or not men peak in their late 20s. And it hit me as a 40-year-old man thinking, damn, if I didn't have the luxury of hindsight and the ability to look back and think to myself, would Justin at 40 currently trade my life for Justin at 27? Would I swap right now for 13 years of more youthfulness, 13 years of me being young and having that like energy that I had when I was 27? Would I trade that for 40-year-old me? I thought about it and I was like, hell no, I wouldn't. Because from 27 to 40, all those ass whoopings I took in my 30s was the life experience that I needed. All the skills that I learned that made me a better executive, made me a high-earning executive, made me employable, got me every check that I got that allowed me to save money. I needed those 10 years in order to be where I'm at today. If I delete those 10 years and I go back to 27, I don't know if my life pans out the way it did. So you need that gap of time in order to improve. And that's where the origin of the episode came from. Why is it better in your 30s? Why does life start getting better in your 30s, Rich? Because you're talking to a young man that was probably where you were at when your son was just one year old. How old were you when your son was one or two years old? I was like 25, 26. Perfect. So at 26, would you trade your life with 38-year-old Rich right now?
SPEAKER_01No, I wouldn't. And to your point, I think your 20s are the time for you to fuck it up. Make mistakes, go through failures, right? Like figure things out. This notion that you peak at 20 is crazy to me, right? Because I am the epitome of fucking your life up in your 20s. But all those things that I fucked up in, all those failures ultimately gave me data points and information. And I gathered feedback and collect collected information to make more informed decisions in my 30s. And I actually created a little uh timetable just to like really go through it. So I was living at home with my mom at 24, new father, barely any savings. Last year of college. By 25, I get a roommate. I do the roommate thing for a couple years. By 28, I get my own place. By 32, I buy my first home. It's not a rocket ship up. It's a slow grind. It's not a rocket ship, bro. It's not a rocket ship. It took me eight years from the time that I had my kid to the time that I purchased my first home, you know, and everything in between. Everything that I learned along the way needed to happen. Who's to say that had I not had my child at 24, that I wouldn't have grinded so hard and saved so diligently to buy my first home in my early 30s, right? I probably would have fucked it all off, just traveling the world or, you know, doing crazy shit. So I think life has a unique way of teaching you lessons, even in your sort of darkest moments where you think your whole life is falling apart and things are not going according to plan. That may just very well be a setback and a teachable moment. And that's what you need to treat those moments as a teachable moment, gather information, take that gem, and apply it when you get to your 30s.
SPEAKER_00Yeah. I mean, listen, the easiest and the most clearest way that I could explain this to a young man that feels like he's behind in life in his 20s is you're not wrong. You probably are in a fucked up spot. You probably are behind right now in your life. But that doesn't mean it's permanent. If you stay there forever, that's because you decided you wanted to stay there forever. If you wanted to live it in your past, then you can stay in your past. But as long as you continue to move forward and take one slow step at a time, you're fine. That's what your 20s are for. And that's definitely what your early 30s are for. You're not a failure if you stop moving forward. I can tell you very clearly that I was the king of making the same mistake not just three times, not just four times. Rich, I would make the same mistake seven, eight, nine times. How do I know this? Because if I think back to my mid-20s, I would be in the same relationships with the same type of girls, and I would never learn a valuable lesson. A big butt and a pretty smile doesn't necessarily mean that this woman is a great woman to build a relationship with. That doesn't mean that this girl is wife material. That doesn't mean that this girl has a high IQ just because she's beautiful. This is the mistake that I made year after year, relationship after relationship, girl after girl. And you know what I kept doing, Rich? I did the opposite of what you just said. I didn't learn from my mistakes. I didn't make adjustments when I made these mistakes. I didn't change my habits or my actions after I made these mistakes. No, no, no. When you change your habits and your actions after you make a mistake, that's how you know you have the signs of an intelligent person. Oh, the stove is hot. Let me not touch it. Young Justin would walk to the same big butt, nice smile stove, and I would touch it every time. And I would be expecting a different result every time. Why is that, Rich? Because in my 20s, I was ignorant. In my 20s, I was young, dumb, and full with a lot of, I could prove it to the world, I'm gonna do it my way. And as I started getting older and I started learning, damn, how many times are you gonna touch this stove and burn your hand, Justin? How many women are you gonna date with the same body type, the same low IQ that are gonna wreak havoc on your life and drain your bank account? This was learning time for me. When I got into my early 30s, I started qualifying women a little bit different. I started qualifying my friends a little bit different. I started qualifying what the fuck I did with my free time a little bit different. And learning those lessons were so valuable. And if I didn't put my hand on the stove and burn myself 10, 20 times, I would have never learned these lessons that today I don't have to go through them anymore. The minute I see something that looks like a failure of my past, I immediately turn the other way. I don't even think about it. And without experience, you can't have the proof of life and the proof to move forward and learn from that experience. So when we say your life gets better in your 30s for every young man out there, it's not like this empty wish, this empty thing that we're telling you, hey, just relax, man. Don't worry about it. Don't do anything. Just relax in your mom's crib. Life will magically get better. No, no, we're not saying that. We're saying if you learn from the lessons and the mistakes that you've made that put you in a fucked up situation, this is a great opportunity to never make those mistakes again and change direction and learn from your mistakes. That's why life gets better. Because now you can start clearing the trail to get to where you always wanted to go. And that comes from learning from your past and learning from your 20s and learning from your 30s.
SPEAKER_01Yeah, bro. And in your 30s, when you reflect back on your 20s, it's sort of like pattern recognition. It's like, what are the things in my 20s that went positively? What are some of the things that went negatively? What mistakes did I make? Where can I improve, right? Like what information have I gathered throughout my 20s to inform myself to make better decisions in my 30s? That's where your 20s are, bro. When you reflect back, it's just like an aggregation of like a little bit taste of adulthood. I'm not gonna say full adulthood because you're still trying to figure out who you are, trying to figure out who your friend circle is, and trying to figure out what you want to do in life, right? I feel like you're very much still trying to figure life out, but it's a little taste of adulthood. And I think in your 20s, just you need to allow yourself to have the freedom to make mistakes. You have to be okay with wanting to try shit and fucking up. Like you said, you have to touch the stove multiple times and realize that it's hot before you're like, you know what? I don't think I'm gonna touch that stove anymore, right?
SPEAKER_00Yeah, I don't think I'm gonna date thick Dominican women anymore. I have to quit. At some point, at some point, I have to stop dating thick Latin women with low IQs because they are the demise. They are my demise. Rich, come on. We've known each other for a long time. I wasn't really qualifying for the right women from an intelligence standpoint.
SPEAKER_01Yeah, but listen, just in your 20s, you know how it is, bro. You're trying to have some fun. You know what I mean? It's go time. You're trying to close, you're trying to hit their base home runs, like you're not really thinking about your 30s and wifing somebody up and settling down or anything like that. So I think a lot is forgiven in your 20s. And I think you need to look at it in that manner, right? A lot of dudes are like, nah, bro, like this is my life, right? Like, I'm just meant to uh marinate and all the things that I've been fucking up in in my 20s. And it's just like, no, bro, it's okay to make mistakes. It's okay to have fun, it's okay to date women that you know that shit's not gonna go anywhere. But in the moment, it just feels like the right decision.
SPEAKER_00Yeah, Rich, I do want to get into friendships because we kind of discussed that friendships, relationships, jobs in your 20s. Before we move on to that, I do want to give one piece of actionable advice that has definitely worked for me for young men in their late 20s, going into their 30s, that feel like life is not moving forward or they're not making progress. Very simple phrase that I live by is fool me once, shame on you. Fool me twice, shame on me. What does that mean? If you allow somebody back in your life after they've made the same mistake more than two times, at some point you have to take the accountability for allowing that person back in your life. And I think the same goes for course correction. Course correction meaning, damn, I want to change my dieting habits so I can be more healthy, so I can look more attractive. I want to save more money so I can save up to move out of my mom's house. Take those two scenarios. That fool me once, shame on you, fool me twice, shame on me. That rule applies for yourself as well, not just other people. So whenever you make a mistake in your life that's not adding or moving you in the direction of your goal, the second or third time you make that mistake, you gotta stop and think to yourself, okay, why is my bank account at zero again? Why every time I step on the scale, or I put on an old pair of jeans, or I put on a shirt, I feel uncomfortable. That's the fool me once. The second time it happens and it keeps going in the direction that is opposite of your goal, you have to stop, circle the problem literally and figuratively. Give yourself 10 minutes and 15 minutes and think to yourself, damn, what am I getting wrong here? And if it bothers you and it feels like pain to think about it, then that's a good thing. You have to sit in a pool of blood sometimes when life doesn't go your way and really do yourself a service by writing down what it is that's going wrong and what steps, behaviors that you can change today to fix it. That is something that changed my life. And I didn't learn that until I got into my 30s, and it really helped me reroute a lot of the things in my life that would go in the wrong direction for too long, and I would have to course correct. So I I did want to say that, Rich, before we moved on to friends and friendship, because I struggled with my weight a lot when I was younger. And if you saw the shit I ate day to day, and if you saw how late I went to sleep and how late I would stay out with artists and managers and mob out in New York, it wasn't a proper indicator of my goal, what I wanted for myself. And if you looked at my bank account back then, your boy was definitely anywhere between $60,000 to $80,000 in debt, two credit cards maxed out. And I kept going out with artists and managers and my girlfriend at the time. And don't let one of the homies get bottle service because I'm chipping in half and putting my credit card down. I was always struggling with my credit score, with how much money I saved, how much money I wasn't paying off my credit cards, and how I was getting killed by interest. I wanted to save, Rich. I wanted to live a better life. But what I wasn't doing was sitting down for 15 minutes, circling my problem, and thinking to myself, damn, what actions and behaviors am I taking to really move in the right direction here? All my actions and behaviors were moving in the opposite direction of my goal. And until I did that, my life really didn't start changing. And that's what my 30s were dedicated to. Really sitting down in the pain, sitting down in the pool of blood and asking myself, do I want to live like this forever? And once you do that, that's when you can start making corrections because you could only stump your toe at the corner of the bed, but so many times before you realize I got to walk around this bed or I gotta fucking move this bed. But you can't keep making the same mistakes over and over. And with those mistakes comes with the people you surround yourself with. Rich, why were friendships and people you surround yourself with so important to you when you're talking about mistakes made in your 20s and your 30s being better?
SPEAKER_01Yeah, listen, I think your 20s, it's funny, right? In your 20s, I don't think you're really rationalizing too much, right? It's just like you're doing things that are fun, like you just want to have a good time. You're not really thinking about your 30s, you're not thinking about the future, you're thinking about the present, bro. And I remember in my 20s, like friends was very important to me. Like all my friendships meant everything to me. What I didn't know at the time was, bro, I had friends in the tech industry, I had friends in music, I had friends from college, I had high school friends, I had friends I partied with, right? And to me, I didn't bucket these people differently. They were just all my friends. What I later learned is once my interest changed, I started to see some friends not part of my circle anymore. Once I left college, stopped keeping in touch with my college friends, right? Once I got a career and I had children, everybody, you know what I'm saying? Like more people just started leave the friend circle. And what I realized, you know, now in my 30s is oh, everybody can't go. What does that mean? Everybody can't go to the next chapter of your life. And guess what? That's okay. It's okay. That doesn't mean you hate these people. That doesn't mean that you wouldn't hang out with them again, right? But understand that for that moment in time, for that snapshot, for your partying phase in your 20s, those five friends you used to go to the lounge with and smoke hookah with all the time, and you no longer do that, those were your party friends. But now they're no longer part of your day-to-day activities. So it's okay to put them on the burner. Not everybody can go to the next chapter. And just I had to learn that shit the hard way because when I got to my 30s and I looked around and I'm like, damn, I probably have only really three, maybe close friends. Wow, one to two, Justin included, right? Like maybe two that I could be like, all right, if shit hit the fan and I needed a phone a friend, like there's only two people in the world that I would call out of 30, 40 that I used to have in my 20s, and I think that is one of the realizations that you come to in your 30s. It's just everybody can't go and understand that your friends in your 20s are just a moment in time. But it's okay if that friend group in your 20s doesn't necessarily make it to your 30s.
SPEAKER_00Rich, I'm so happy you mentioned that. Because if you're a guy that is struggling with telling your closest friends from maybe high school, maybe college, that you're not interested in going out. You're not interested in doing the things that you guys used to do five or 10 years ago. It just doesn't excite you anymore. You just want to stay home and figure out your next steps. In your life. If that's you, then this is something that is a sign of progress in your life. A sign that you're just tired of doing the same old shit because you keep getting the same old results. If you do the same things, you get the same results. If nothing changes, nothing changes. So hanging out with friends from when you were a teenager in your 30s starts to hit a little different when they invite you out to do things you did as a teenager and it doesn't excite you anymore. Stay right there, my guy. That's perfect. That means that you're separating yourself from the pack and you're intuitively, your body is starting to tell you, man, we got to do some different shit if we want to change the formula, if we want a better future for ourselves. That's why the 30s are so important because if you're still living the dream of 17-year-old Rich or 17-year-old Justin at 31 years old, you have a problem. No teenager should design the life script of a 30-year-old man. But if you really think about it, a lot of 30-year-old men are still living in the idea of a 17-year-old version of themselves. That's fucking sad. I wouldn't let no teenager tell me how to live my life or tell me what to do. So why do you still live in the mind state and the dreams and the goals of teenage you? That is a clear sign that you haven't made any growth or progress or had any maturity in your life. I think about, I think it was like four years ago, it was BT weekend. I had close friends from back home come out here. And these are friends that I used to mob out with. Not my professional friends, not my college friends. I'm just talking about guys from high school, Rich, that we both know. And they came out here because they were following me on social media and they saw how fun my life looked. I played basketball, I went to award shows, I hung out with artists. They didn't get to see the amount of time and work that I spent in isolation and how much time I was at the office doing my job. So when they came out here, it was party and fun time, which I wasn't mad at because I was single when I first came out here and I wanted to show my friends a good time. But like you said earlier about old friends and their goals versus new you and your new goals, sometimes it's like oil and water. It doesn't mix. And I had to suffer that consequence, Rich. Because when my homies came out here, they were out here for four days. They stood at my crib for two days and they stood in an Airbnb for the other two days. BET weekend was a nightmare for me. Every venue we went to, these guys were harassing people for contact information, walking up to artists, asking them to take pictures with them. Every girl I was cool with that I worked with, these guys were shooting their shot, just being low-key disrespectful with them. And I was cool with it because these are the homies. I already know what type of time they're on. But what I couldn't deny was the feeling that I felt, Rich. The feeling that I felt that was like, damn, whatever these guys are on, I'm a little embarrassed for them. And I'm a little embarrassed for myself when I think about, damn, early 20-year-old Justin was on this type of time. And it would be sad if Justin in his mid-30s was still moving like this. And just that little BT weekend and being around the homies from back home, that showed me the progress that I was making. And it was even more clear, and it kills me to say it, but it was even more clear to me that I was happy with the progress I was making. And I was happy with the growth that I was making. And whatever these guys were doing that I was kind of annoyed by was a gap of where I used to be and where I'm at currently. And that is a good thing. That's not a bad thing. But in the moment I didn't feel like it was a good thing. I actually felt guilty for feeling the way I felt.
SPEAKER_01Yeah, listen, I think that's a great story, Justin. If you if you think of sometimes I view like friends and these phases that we go through in life as like a snake shedding its skin, right? Like you go through high school, and once you graduate, you shed skin, right? And hopefully, maybe you either enter the workforce and you go to college, but somewhere between 20 and 29, you're this specific person, right? Like you're trying to figure out life, you have this uh what you believe to be is your current identity, and then post 30, you shed new skin and you become a new person and you have new evidence of all the failures, all your wins of your 20s, and you start to apply them to your 30s, right? And that's why I think the 30s are such a crazy G code, right? Because you have this information, you know what worked in your 20s and what didn't work. But what do you do without that information, Jess? You know what I'm saying? Like you have to be able to shed that skin. And to your point, sometimes not all your friends are gonna be on the same time, not all your friends are gonna shed their skin of high school at the same time. Some motherfuckers are gonna go into 25 years old thinking they can still mob out like they used to back in high school. And we've had a whole episode on this where we've had friends, we've shared stories where we've had friends who still live in their glory days. They never matured after high school and they still want to be doing the same old shit that you used to do back in high school. But at some point, you have to figure out a way to sever those ties because those, like I said before, bro, not everybody can come to the next chapter of your life, and you need to be smart enough to identify when people are still on some old shit and when you're looking to progress and be on some new shit.
SPEAKER_00Yeah, Rich, you use the word identity, and I think that's a big one for this episode. Because you're talking about a guy that's 27, 28. He keeps thinking, damn, I'm gonna be 30 soon. Damn, I'm gonna be 30 soon. I'm gonna be old, I'm gonna be washed. All my dreams and hopes and aspirations, everything I wanted for myself is never gonna happen. This is it. I'm 28. This is it. This is gonna be me for the rest of my life. I'm broke. I lack confidence. I'm unhealthy. I'm single, I'm confused. I live with my mom. That's the headspace of the guy we're talking to right now, Rich. The numbers show it. That's where a lot of these guys are at. And I think what we are trying to help with in this episode is that we want to take that Ziploc bag of identity that you've given yourself, these words that are like fear-based. I am this thing permanently. That's wrong. Let me take that ziploc bag and open it up a little bit. Let some air in there. I am living with my mom. Dot, dot, dot. That's really what your life is. It's not a permanent identity, it's an evolution, it's a phase. You're just going through a phase of your life. As long as you keep going, you keep going. There are better and bigger milestones and better and bigger lessons ahead. There's better and bigger bags of money ahead. You have to keep going. This idea that you lock yourself into an identity, that's not true. You're not that forever. You what are you going to freeze at 28 years old? If you freeze at 20 years old all the way to 40 and you stop trying, then that's your identity. That's who you are. Rich and I can tell you from real life experience, our 20s weren't the most glamorous because we didn't have the best foundations growing up. So we struggled out the gate. The race started, and we were still inside of the locker room looking for our sneakers. The rest of our friend groups were out of here. I know kids that graduated college at 22 years old, and I was just getting into ruckers at 21 years old. I didn't graduate college till I was 24, 25. I was a delayed starter. I started my life maturity and started picking up the lessons that life had for me really late in my life. But I didn't accept this idea that if I was broke at 29, I was going to be permanently a broke person. I am a broke person. I never admitted that. I never waved the white flag. And I don't want our listeners to do the same because you're still young, you still have time, but you have to keep moving forward. Do not lock into your identity when you're young because you'll stay there forever if you believe that's who you are. Yeah, that's exactly right.
SPEAKER_01And sometimes just it's it's not really necessarily your fault. Like I don't want to put blame or shame on anyone else, but there is a sense of like the world swaying you one way or another. Meaning, mom is expecting you to go to college, become a lawyer, become a doctor, right? Your big brother who went to the military is expecting you to enlist in the military, right? So you have all these reference points of people who place expectations on you on what you should be doing or sort of how your life should be unfolding. And I think that really adds to the complexity for the 20-year-old guy who's really trying to figure out who he is. Where does he fit in the family dynamic? Like, is he gonna follow what mom is telling him to do, dad, brother, uncle, sister, right? Like, there's a lot of like figuring out that you have to do.
SPEAKER_00We said it earlier. If you're taking advice from people that decided at 18 that you were gonna be something, not only are you allowing yourself to live in an idea and a dream of your 18-year-old self, you're allowing people around you to tell you what you're gonna be based on what they know of you from 17 and 18. You're living in an identity of a teenager or the dream of a teenager. But you have real life proof at 28 that you can pivot, like you said earlier, which I thought was a great visual representation. You can shed old skin and turn it to whatever you're gonna become moving forward. But if you're listening to your mom, your mom keeps reminding you of everything you fell short on. Most of the time, those are her dreams. They're not even your dreams.
SPEAKER_01Great point. And that's one of the biggest mistakes I made in my 20s, just I outsourced my self-worth to people. When it came to work, I wanted my boss to feel like I was the best worker and I knew everything, right? When it came to friends, I wanted all my friends to view me as like a smart guy. When it came to girls, I wanted them to see me as this like amazing guy that they could date, right? And if I didn't get that positive feedback from the world, I would feel like shit. I would crumble. I really felt like a lost puppy in my 20s, bro. Like I was really trying to figure out who is rich? What are we about? What are our ambitions? What are our aspirations? Who are we? Who are we really? I really didn't start to get the answers to those questions until I hit my 30s. So I had to go through the painful reality of figuring out life in my 20s and making a lot of mistakes in order to derive at some unanswered questions of who is rich in his 30s. And I think you only get those answers by going through the fire, bro. Yeah. Yeah.
SPEAKER_00You know what's funny when you were talking about seeking validation. I kept thinking about this story. And then there's a part of the story that ends up in Starlitz at a at one of the most legendary strip club strip clubs in Queens. I need, I need to hear this. Yeah. I don't know. I mean, the best way I can say it is we're talking about a 27-year-old Justin. I had just started my first, probably my first three months at a new role at the first record label I worked at before my like entry-level jobs. This Justin was probably $50,000 salary, give or take, $60,000. So if you break that down after New York City and New Jersey taxes, I'm probably got like $800 in my pocket to move around with for the week. Then you add the fact that I had just graduated college late and I took a lot of loans while I was at Ruckers and when I was at community college. So I was probably sitting in about $70,000 to $80,000 in debt. And I had just gotten a Macy's credit card before my new job. So I maxed that credit card out so I could look good when I'm out with my artists and my managers and I'm hanging out at work. And then you know, I got another credit card to make sure that I can, when I go out with people, I can swipe my credit card and pay it later. This was normal to me. I didn't really know anybody that gave me any rules on how to be good with my finances. But that's not an excuse. So if you really think about my situation, $70,000 in debt, two maxed-out credit cards, and I'm only making $50,000 a year. I'm not the best at math, but that seems like I'm already 20 feet under the ground and with no way of getting out. But needless to say, you're probably asking, how the fuck did you end up in Starlet's in a strip club in Queens if you have no money? Well, that's what you said, Rich. And I was thinking about it. When I was younger, I had this insatiable appetite for other people's approval. I needed people in the music business to know that I was fucking lit because that's the only way you can win in my business. You have to be lit to be a part of the lit community. And then once you're a part of the lit community, then you start making more money. It's the most ass backwards, hustle backwards formula ever. I was hanging out with an artist manager that kept telling me, yo, I'm looking for someone to be my B person in my management team. And every time I meet up with you, I get the vibe that you know what's going on. I get the vibe that you know how to move around with my artists. I feel like everywhere you go in New York, you know everybody. I need a guy like you. I need a guy like you to move my artists around the city whenever we're in New York. So of course, I took the bait like a fucking idiot. These guys were in New York for a week. I'm not even gonna say where they're from, because if I did, you would know where the artist was. But I didn't even have a corporate card yet. So I didn't, I couldn't expense anything. But these guys kept telling me, yo, this is the boss, that insert label. Mind you, I'm only 27. So I'm not the boss of anything. I barely got enough money to get in and out of fucking the train station. Rich, we start the night off. Me, the artist, the artist manager, and a and a cameraman. Four grown men. We start off at a very nice restaurant. Everybody's ordering drinks, everybody's ordering food. Bill comes, bill's about $2,500. My fucking heart is beating out of my chest because I'm like, yo, I don't even have the money for this. So I slide off to the bathroom. I'm praying to God while I'm at the bathroom. I hope somebody covers this fucking bill. And I hope they don't notice that I slid off. I come back, bills paid. Whew. Fucking sweat off my forehead. I tell the manager, yo, what I owe you for this. He's like, nah, don't worry about it, but the next stop is on you because you slid off and don't think you're low. I said, it's cool, bro. Don't worry about it. Where are we going next? He said, One oak. You know what one oak is? One oak at that time was one of the most legendary clubs in all of Manhattan. Have you been to One Oak?
SPEAKER_01Never.
SPEAKER_00Rich, the who's who, fashion, finance, music, everybody. Little ass venue in Soho area. We go to One Oak. We get to the front door. They're like, bottle service line, regular line. Manager's like, let's go to the bottle service line. You know, the bouncer, super disrespectful. I can't have four dudes in here with no women. Y'all gotta pay 5,000. Rich, I was ready to slide. Right in the middle of that moment, I was like, I gotta get the fuck out of here. I'm out of my the manager's like, don't worry about it. We're rolling with El Presidente. This guy got us. I'm looking to see if he's talking about me. And then I look over my shoulder, like he might be talking about somebody else. Because I know he's not talking about me. This dude is talking about me. He gives the bouncer his credit card. We all go in. Now I'm at one oak rich, nervous, thinking to myself, like, yo, I gotta figure out a way to get the fuck out of here before this bill comes. Bro, we got the hookah popping, we got the bottles popping, we got the DJ shouting out the artists that we're with. And I'm sitting there thinking to myself, like, yo, I gotta figure out a game plan. Luckily, I ran into one of my senior level people from the label I was at at the club, and I ran over to him. I was like, yo, please, bro. I'm with said artist. This artist is a free agent. They're trying to sign our label. Please come over and take care of this bill because I don't have no money. He was like, Why would you go out with no money? I'm like, yo, please don't worry about it. So anyway, shout out to this human. Came over to our section, took care of the credit card situation. He actually gave it to the waitress and said I could sign for it. So when the bill came, I looked like a big dog. So I signed for it. So I'm over here looking for the executive to gave me the card, so I give him his card back. I run into him at the at the exit of the club. He's like, yo, I'm leaving for the night, but you can't have my card. Like, you better go home, bro, because I'm not, I can't help you. I'm like, nah, we're good, we're good. But I give him a dap, he leaves. While I'm at the exit, the artist, the artist manager, and his entourage, that is now five more people, walk out and they're like, yo, they're grabbing me by the shoulder. Yo, we're with this guy, we're with Justin, El Presidente. This guy is gonna take us to Starlet's in Queens. Rich, I dodged two bullets. Didn't spend one dollar at that moment. I find both of us in car service on our way to Queens. From Manhattan to Queens is a very long ride. So that whole ride, I was plotting on how I'm gonna get out of this one. Rich, when we got out of the car service and we got online for the strip club, I tell the manager and the artist, yo, I gotta take a call. I'll be right back. I took a call, I literally waved down a cab and took my ass right back to Crown Heights, Brooklyn, where I lived at. And I didn't pick up another phone call for the rest of the night. I dipped on an artist and artist manager right before we got into Starlitz because I knew for a fact that I wasn't gonna be able to finesse my way out of that because a strip club is all cash. If you don't have cash, you can't even be in the strip club. You can put it on a card, they'll give you cash, but the tax is crazy. I had to get out of there ASAP rich. That story is one of the most embarrassing stories of my life because you're talking about a guy that only made $50,000 a year, was $70,000 in debt, and had two maxed out credit cards. I had no business being outside. Why did I do it? Because I seeked approval from other people and I wanted to be more lit than I actually was. And the quickest way I could do it was by LARPing, by capping, by making it seem like I had more than what I had. And what happened was these big boys exposed me because I wasn't what I thought I was. Now, if I think about that story, looking back at 40 years old, I laugh because I survived that moment. But what came of that moment, Rich, was the biggest life lesson. Stop making pretend that you have a lifestyle that you can't afford. Start getting your money together so you never suffer that embarrassment ever again. Rich, never again do I go to a strip club with no money in my pocket or expect another man to pay for it because that's the lesson I learned in my 20s that made me a way better human in my 30s. Without that fucking experience, I would have not been here right now to share that story, and I probably wouldn't have gotten my finances together. I'm happy to say that I have zero debt currently. And that was one of the most embarrassing moments of my life that led me to wanting to solve that problem. That's real, bro.
SPEAKER_01Listen, your 20s will shame you into progress, bro. Like it'll test you. Say it again for anybody listening in the back, bro. That's facts. Your 20s will shame you into progress, you know? And I think that's exactly how you need to view it, bro. It's like it it's weird to say in hindsight, right? We're in our 30s, Charles, you're in your 40s. We have the advantage of looking back in time and being like, oh, that should actually worked out better than I thought it would, right? But when you're in it, bro, when you're 25, 26 and you're in the trenches and you're in the moment of a fuck up or a failure, it doesn't feel that way. It just feels like the world is ending and things are crumbling underneath you. And Justin and Rich are here to tell you, it's okay, bro. It's okay. Things are gonna get better. You're gonna be able to move forward from this. And once you reach your 30s, you will have the proof of all the fuck-ups that you had in your 20s to give you the ammunition that you need to have a successful 30s. Bro, I locked in my house at 32 years old. Never in a million years did I think I would be able to purchase a home at 32 years old when I filed for bankruptcy at 19. It was unfathomable to me. I just thought I was a financial screw up, you know. And fortunately, I course corrected. And post-30s, like all my decisions are based on a sound financial choice. I no longer make, you know, stupid mistakes with money because I know what going down to zero feels like. But that only happened in my 20s for me to have that piece of data, piece of information to influence my 30s. And, you know, just there was a concept that you shared with me that I think we definitely have to unpack because I think this speaks a lot to the identity of what you ultimately become when you reach your 30s, right? And I think a lot of it has to do with confidence. I think the failed reps, the trials and tribulations, all your failures in your 20s ultimately shape your identity in your 30s, and it really gives you confidence to operate in life, confidence to move forward, confidence to have the knowing and understanding of like, oh, I'm no longer guessing about who I am as a person. I think I know who I am. You really start to fill in your shoes as an individual when you hit. Your 30s.
SPEAKER_00Yeah. Rich. Buy a note to the young man listening to this episode. If you feel behind in your 20s or your 30s, I have some news for you. Millionaires under the age of 25 in the United States, it's like one in every 1,000. It's like 0.03%. You can't find a millionaire that's under 25 years old. But for some reason, they all live on your phone. Every time you open your phone, somebody's making a million dollars. Somebody's net worth is a million dollars. Somebody hit a 20x play and they're going to put you on it. That is what creates a lot of the dark mentality for a lot of these young guys, Rich, is they're sitting at home thinking, damn, everybody else is doing better than me. The average home purchased in the United States, oldest that it's ever been in recorded history. That age is 40 years old. Last data checked was 40 years old, the average home purchase. Rich, you bought your house at 32. You probably felt like you were behind when you bought it back then. People buying houses at 26, 27, 28 is an absolute anomaly. Don't feel like you're behind. You still have a lot of growth. You still have a lot of progress to make. Why do I share all that information, Rich? Because I feel like the reason why a lot of these people think their life is going to stay stuck is because at 28, you're seeing millionaires on your cell phone all day, guys that are young, making a lot of money, quote unquote, a lot of money. And then you're looking at your friends from high school and college getting married, buying houses. But they don't own the houses. They're getting insane mortgage rates. This is not the dream you want. Trust me, keep chipping away at your own dream and keep making edits and adjustments as you move forward. This envy that we have towards other people and their progress is what pollutes a lot of our own personal value. And I feel terrible for young men because Justin in his 40s would most definitely not trade my life for anybody in their 20s. Because if I trade my life, that means I have to trade my life experience. And that means I have to train all the life lessons I've learned to being a better man today. Mentally rich, I'm in a whole nother place at 40 years old because I've learned to deal with all the shortcomings that I felt like I had when I was younger. And it takes time to figure these things out. It takes time.
SPEAKER_01It takes time, Joseph. And I'm so glad that you mentioned that comparison trap because, bro, you really have to want to run your own race, bro. Like, sure, are there people your age that probably hit a lick and are millionaires or influencers or famous streamers? Sure, right? They're an anomaly in the fucking matrix. Cool. But that's not the reality for most folks, bro. You know what I'm saying? But you have to want to run your own race. Everybody's out there chasing a different goal. The streamer's goal is not going to be your goal, right? Like you have to want to run your own race. And to your point, Juss, I feel like all those fails reps in your 20s are proprietary to you. Think of it as like a divine fucking thing where like you had to go through those experiences in order to start winning in your 30s. Had I not fucked up so much in my 20s, I don't think I would be nearly as successful in my 30s as I am today. And I'm by no means a millionaire, right? But I'm much closer now than I was in my 20s. And I'm telling you, just all those trials and tribulations, everything that I thought was a fuck up in my 20s, influenced my 30s. And if I'm being quite frank, bro, I'm 38 today. I don't think I've hit my peak yet. So this idea that you're peaking in your 20s is crazy to me. I'm 38 and I don't feel like I've peaked yet.
SPEAKER_00So what's your response to the young man that says, damn, Unc been peaked? And now he's trying to tell us that being in his 40s is better than being in his 20s. I'm delusional, right? No, but that's pretty much what this episode is saying. If I really think about it, shout out to my barber. I just got a new barber. My haircuts are looking fucked up is because of him. My new barber is 23 years old. And he was someone that I kind of went back and forth on this episode topic about. I told him, he's 23 years old. I told him, man, like your 30s is when life starts clicking, when shit starts adding up. When the snowball of all the money you saved, the snowball of all the mistakes you made and all the corrections you made after making those mistakes, the snowball of all the good and positive and resourceful and helpful relationships, romantic and friendships of life, those three snowballs, they start going downhill. That's good momentum. That's positive momentum. And not only does it get go faster, the snowball starts getting bigger because it compounds. I had no clue that this was gonna happen in my 30s. And that's what I was trying to tell my barber, trying to give him this like perspective. Like, no, your 30s is when all this shit starts clicking together and it starts improving faster than you thought. You know what this dude tells me while he's cutting my hair? He tells me, yeah, but I'm not trying to be old and rich. I'm trying to be young and rich. I want to get there faster. I'm like, what's wrong with being rich in your 30s? Like, 30s is not like you're dying. He was like, nah, but most people that are 23, they fear what's happening in the world. They fear the housing situation. They fear AI taking all of their jobs. They fear that women are never gonna want to be with them because they're not rich. So they would much rather have it now rather than punting it into this future that they don't know about. Which when he said it that way, Rich, it made sense to me. Oh, they don't believe that this is gonna exist 10 years from now. So they're trying to lock it in right now. And I respect that. I respect that perspective. But I have to say, you're not right because you don't have the luxury of time to make that point.
SPEAKER_01Yeah, you're 100% right. And I do respect that point, but at the same time, I feel like a lot of young guys in their 20s, they all want to be on the rocket ship, bro. They all want to get the million dollars fast, they want to invest in crypto today and in two years, 100x their money. Like everybody's trying to get it fast. And I don't knock the hustle. Just you and I had our fair share of side hustles where we try to get it fast too. Guess what? None of them fucking work. But with all those side hustles, with all the failed business plans that me and Justin had was the birth of failures media and failures podcast. We had to fail in multiple different businesses to derive at this point, right? Only when you have that collection of data are you able to make that informed decision. So I say that, and I also share that there's a difference in ideology between somebody who's 20 and somebody who's a little older like us, in the sense that we subscribe to the marathon, right? Nipsey hustle, right? The the long game, the longevity. We understand that we're running a very long race. And part of this race, when you're running the marathon, you're looking at people to your left and your right, and you're looking at the distance, and you're looking how far you have left to go and who's behind you. In that marathon process, bro, you're collecting data points. You know what I'm saying? To ultimately try to win the fucking race of life. But if you try to try to, are you gonna get it on a Waymo and just like run the fucking marathon inside of a Waymo? Yeah, you're trying to cheat life. Like that shit doesn't work.
SPEAKER_00You can't cheat the game, you can't cheat the game, you can't cheat hard work. Rich, there's one question before we wrap up that I have to ask because it came up on the YouTube comment sections. What's one thing that 25-year-old Rich would have killed for? You wanted more than anything, but then you look back at 38 years old and you laugh and think to yourself, I am so grateful that I didn't get that thing. Because 25-year-old Rich is a fucking idiot. He didn't even know what he wanted.
SPEAKER_01I have the answer for this, and and it was women, bro. I thought every woman that I was pursuing in my 20s were like, Me and you both. I I hold on, I got the same answer. This is great. Yeah, I was like, nah, this has gotta be the girl that I marry. Like it's her, it's her. I said I had that thought with multiple women, by the way, which was extremely naive.
SPEAKER_00Just everyone after the other.
SPEAKER_01Like this, everyone was the one. Yeah, yeah, everyone was the one. And and every time those relationships were reaching a breakup point that were like, nah, I was like, nah, we can't break up. You're the one. Like, what do you what are you doing? You're breaking up destiny, right? Foolish. Absolutely foolish. I didn't find my person until I was 34 years old. And it wasn't until I had all those failed relationships and I got to experience what went right, what went wrong, and the qualities that I'm looking for in an individual that I derive at understanding who would be the right alignment for me. I didn't get that information until I reached 34, almost 35 years old. And now I'm in a happy relationship. So I think it's pivotal, bro, that like you really analyze. I'm struggling, Jess. I'm struggling because I remember how fucking naive I was at 25, 26 years old. Even the feedback that I'm sharing right now, my 25-year-old self would tell this 38-year-old self, shut the fuck up, bro. Like, let me live my life. You know what I'm saying?
SPEAKER_00But you would be like, trust me, gang, you don't want that woman. You don't want that woman. Maybe for a night, but not forever. Exactly. Now, if I can think with full clarity of a man 40 years old, and I could look back at the 25-year-old Justin, and if I could point that one thing and say, listen, 25-year-old Justin, you think you want this thing. But me at 40, I can tell you with the utmost clarity, you will regret keeping this thing in your life because it will ruin your life. There's two things that come to mind. One, the fucking Cadillac that I wanted to buy for $100,000 when I worked at a car dealership. I'll never forget it. It was like sliding doors moment. The difference between me signing that paperwork and putting my credit card down and me not doing it was just like one or two days where the car wasn't in the lot yet, and I had to come back the next day. And I decided the next day, you know what? I don't want that car anymore. I have the same situation with a young lady that I dated in my early 20s. Let's call her Sabrina. Sabrina was beautiful, great body. Sabrina didn't work out. Sabrina wasn't that bright. Sabrina was touched by the gods of genetics. And I used to hang out with this girl all the time. Me and her used to talk all the time. She cheated on me with my closest friend. I took her back. She was in between me and my closest friend for a minute, and then she decided she wanted to be with him permanently. I suffered for a cool year or two thinking about Sabrina. Damn, this was supposed to be the girl for me. She's beautiful, she's naturally attractive. She does it for me. This person is my everything. At 40 years old, Rich, I look back at the relationship with that woman and I think to myself, I would have risked it all to keep that girl in my life permanently. If she would have asked me for a marriage ring, I would have given it to her. If she would have asked me for a kid back then, I probably would have given it to her. The hindsight of looking back from my 30s, back to my 20s, that Cadillac and that woman are two things that I matrix bullet skimmed my forehead. I could have died a slow death of interest payments to that car and a life full of headaches and arguments with a woman that I would have never wanted to be with long term. So I'm very grateful when I look back and I think about my 30s and all the failed relationships that I had that led me to the relationship that I'm in now. I'm in a very happy relationship. But 24-year-old Justin was in no position to be making decisions for 40-year-old Justin. And I'm happy that that didn't happen. Because if I would have had to live with those decisions for the rest of my life, I would have been fucking sick. So that is a nice little bow to put on this episode because you think at 27, 28, damn, this is it. This is the only thing happening in my life. I am going to be this person forever. Rich and I have 60 minutes of conversation before this moment to prove to you, man. We're proving to you. Know the fuck this is not the end of your life. You're 28 years old. You're good. Keep marching forward, keep learning, keep making mistakes. Important that when you make your mistakes, you make edits, you make updates, you correct those mistakes, and then you keep moving forward. All that shit adds up when you get to your 30s. And there's a lot of beautiful things that happen later in your life that would never happen if you don't have the luxury of experience from your 20s. That's really what this whole shit is about. And if every embarrassing story that Rich shared and I shared is not proof, I don't know what to tell you. Fuck it, take the loan, do your thing.
SPEAKER_01Just man, I want to end on this quote: your 20s gave you the lesson. Your 30s are where you find out if you actually learn them. There you have it, man. Failures podcast. We out.