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
The Self-Improvement Loop: Why You Still Don’t Feel Ready to Date
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You’ve been going to the gym. You’re saving money. You’re working on your career, trying to build confidence, and becoming a better version of yourself. But somehow, you still don’t feel ready to date.
In this episode of Failures Podcast, Rich and Justin unpack the self-improvement trap, the point where personal growth stops helping you move forward and starts becoming a safe way to avoid rejection, dating anxiety, and failure. You tell yourself you’ll start dating when you lose more weight, make more money, move out, get the apartment, build more muscle, or finally feel confident. Then you reach the goal and move the goalpost again.
Rich opens up about spending six years in “Robot Rich” mode after a failed relationship, focusing on money, fitness, and work while avoiding another serious relationship. Justin talks about reaching 40 and realizing there was an opportunity cost to waiting until everything felt perfect before building a family.
They also break down fear of rejection, perfectionism, dating confidence, social skills, modern dating, and why being a work in progress doesn’t make you unworthy of love. Self-improvement matters, but you don’t have to finish becoming the man you want to be before you let someone get to know the man you are today.
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
If this episode helped you, share it. That’s how we grow.
You look great, champ. You got enough money. Go out there. Go ask a girl on a date. Go out there and get rejected. Who cares? Every no will eventually lead to the one yes that will make all the no's before that irrelevant. That's what we're saying on this episode. You are a part of a huge generation of people that have the same problem. Myself included, Rich included. So I don't want you to feel alone. We just want you to know stop fucking around with some mosquitoes and go out there and kill something. Kill a dragon. Failures podcast. Today we're talking about the man who keeps waiting until everything is perfect. All the T's are crossed, all the I's are dotted. He needs everything to be perfectly lined up just to get started. Self-improvement has become his identity. Self-improvement has become a generation's greatest delay tactic. Failures podcasts might be a part of the problem because we are a self-help platform. This is why these platforms are so big. So why are we talking about men wanting everything to be perfect just to start? Because it seeps into a lot of things. It seeps into dating, most importantly. Rich and I know this because a lot of our information and our engagement, our community is about how do I start? I've already done the work. I have a low body fat. I've been going to the gym for two years. I have X amount of money saved up. I'm about to get my own apartment. How do I start? Well, that's what today's episode is about. If you really want to know how to start, just start. I know that's not great advice. You could end the podcast right now, but all it really is is a matter of removing the fear from starting. Imagine if you had a Porsche 9-11 or the rarest Ferrari in the world, and it just sat in your garage and you never took it out for a drive. That's essentially what young men are doing today. We have research that tells us 65% of men under the age of 40 report as single. That means healthy, young, thriving, ambitious, charming, charismatic men are sitting at home, not taking the leap of fate, denying themselves rejection, denying themselves friction. You need rejection. You need friction in order to get what you want. And that's what Rich and I are going to talk about today. Don't be the Porsche Cayenne, the Porsche 9-11 sitting in a garage. Be the guy who's on the road figuring it out. And if you're in a Toyota, who gives a fuck? As long as you're figuring it out. Rich, honestly, why do you think men are addicted to improvement as a delay tactic? And is this something you can relate to? Because I know I can.
SPEAKER_01Just I've definitely been this guy, bro. And like if you think about the guy that's self-improving, right? He's going to the gym, he's saving money, he's stacking his bread. And you think that because you're progressing and you're moving forward, that you're doing the right things. And you in fact are. But I think the problem is these guys are self-improving and they're getting prepared. And I'm getting ready and I'm getting fit and I'm getting strong and I'm getting fly and I'm getting my money up. And you know what happens after a while? You stay stuck in that loop of getting prepared. You're just always getting prepared all the time. But at some point, you have to take action. At some point, you have to execute. At some point, you have to use those muscles that you've been working to get for all these years. At some point, you have to spend some of this money that you've been stacking for many years. And I think that's the core thesis of this episode. It's like this is about the young man who's constantly just getting prepared, just over-optimizing himself to the point where he's delaying the ass whooping that life is prepared to give him when he has to take action on something.
SPEAKER_00Rich, you said something that comes up a lot in the self-help space, more on the nerdier side, more on the tech side, where a lot of people are good at like analysis paralysis, where you do so much research before you actually take a shot. And a lot of this language is comes from business. It comes from startups, it comes from starting your own business, being a solo entrepreneur. And it's funny how it relates to dating. And what you said before about over-optimizing is actually a term I had to look up. What is optimizing? And what is over-optimizing? So you're saying these guys are not lazy. They're very motivated. These guys don't lack ambition. They go hard. You give them a goal. If you tell them they have to solve for it, they'll solve for it. But what they fear is rejection. And that word over-optimizing, I want you to speak on that a little bit because I think that is the guy who's listening to this episode. He's not completely down bad. He has his life together, but he's afraid to jump off the porch.
SPEAKER_01Yeah, that's exactly right. And I think what happens to this guy in that over-optimizing cycle that he's in, you know what happens, just the goalpost keeps moving. So you tell yourself, I need to save 60K and have an apartment and have a stable career before I start dating. Then you know what happens when you reach that 60K salary when you get the apartment, when you get the stable career, the goalpost moves. And now you're like, nah, nah, nah, I actually need 100K. I need 100K saved instead of an apartment. I actually need to have a house and I need to be six years into my stable career, right? You just move the goalpost. Yep. And that's part of the delay that these young men create when they're getting prepared, right? Because you continue to move the goalposts and you never actually get to go into the dating scene to figure out your worth in the open market, right? To figure out like if girls find you funny or interesting or handsome, because you're always getting prepared.
SPEAKER_00Rich, I relate to this guy, and I have a quote that I pulled from our community, and I also have a story I want to share that relates to this quote. This one was powerful. I wanted to say it in the intro because I think it hit me in the heart. It's something that when I read it, I thought about myself. Don't spend your whole life transforming yourself into a man worthy of love and companionship, but you forget to let anybody love you or fall in love with the man you're becoming. And I think what's powerful about that quote is don't forget to let anybody fall in love with you or fall in love with the man you're becoming. And I think that's the pain point in this episode, Rich. It's not necessarily the guy listening to this episode that is the villain. It's not your fault. The real problem is that you're not allowing yourself to be loved as a work in progress. And maybe an idea of your old self still dominates your brain and you still feel in fear of being judged as your old self. But give yourself credit, man. You're making progress. Allow someone to learn who you are, flaws and all. Allow someone to love you while you're in progress. And the truth is, Rich, I'm curious to hear your feedback. The progress never ends when you're someone that's constantly chasing self-development, self-improvement. You want to build your bank account, you want to build your body, you want to be a better you. I know you personally, Rich. You still strive for excellence. But should that stop people from loving you how you are today?
SPEAKER_01No, it shouldn't. And I'm not speaking on high, bro. Like I definitely relate to this young guy. I was 24 years old when uh I had my first child, and my first relationship with my baby mom didn't work. And I was so hurt by that situation not working that, bro, I went into full optimized mode for the next six years. You became robot rich, straight optimized, robot rich, yeah. Just save money, go to the gym, work as much as possible. And yeah, I would date here and there, but I never got into a formal relationship with any woman. And it got to a point, exactly what you just said, Jess, I had fear of having another failed relationship. I had fear of being rejected by a woman, right? I had fear of not being enough for the opposite sex. So I felt like I needed to just self-improve to the point where there was no ending to that self-improvement, right? So, Brian, I went on a six-year run of just that. And it wasn't until I reached my 30s that I was like, well, wait a minute. I learned this very valuable lesson, and I forgot where I read this from, but it was like, you have to go through heartbreak in order to push through in every relationship, like just numbing yourself and avoiding the terrible feeling of heartbreak is not a healthy way to operate. And I had to reprogram and reframe my mind to view relationships as like, okay, this is something that I just need to enter in and build with someone. And if it doesn't work, and if that building collapses and you know we don't succeed in this relationship, you heal, right? You hurt, you heal, and then you move on to the next one. And I had to learn that, bro.
SPEAKER_00Rich, can you relate to the guy that is in the group chat or out with his friends for drinks or at the gym with his new gym friends? And he's always saying, No, no, I'm gonna start when? I'm gonna start when? I'm gonna start when I can bench press this much. I'm gonna start when, I'm gonna start when I feel more comfortable taking off my shirt in front of a woman because you know I've always been a little a little overweight. I'm gonna start when I officially move out of my mom's house and I get a one-bedroom apartment in insert big city. I can't do that in this small town. Are you relating to that guy? And the six years that you were in that transition, what advice can you give to that guy right now?
SPEAKER_01You gravitate to what's safe, right? Like if you're just always in the getting prepared mode, right? Like that is a situation and a strategy that you have a hundred percent control over. And there's no way that you can get rejected if you're getting prepared, right? And if you think about it, you're protecting your ego too, alongside of that, right? So if you're always going to the gym, no one's gonna ridicule for being the guy that always goes to the gym. If you're saving money aggressively, no one's going to ridicule you because you're saving money aggressively. These are all positive things that you're doing for yourself, right? But it's a very safe, controlled environment, one that protects your ego and one that protects you from any rejection of the outside world, right? So it's weird, right? Because in one end, you're in this like positivity loop, but at the same time, you're in this growth chamber, right? Like you're it's sort of incubating yourself. Yeah, yeah, right. But at some point at some point, this egg has to hatch and you have to go out and and fly and get food and fend for yourself.
SPEAKER_00And I think that's what we're trying to say. Rich, I can't find the guy who said it, but one of my favorite quotes is what does one have to be to be ready? And that shoots an arrow right in the heart of the over-optimizer, of the guy that's always tinkering, the guy that writes up a business plan, but never puts the product out. The guy who buys all the best outfits, watches all the TikTok videos on what's the best cologne to wear on the first date, has a dresser full of colognes, has a closet full of clothes, but never actually takes the step forward to start the business or go on a first date. This is for that guy. My question to you is what does one have to be to be considered ready? What does ready mean? Ready means you're willing to try and fail, you're willing to learn some shit by doing, you have to be in it to win it. The only way you can grow is by hitting go. These things are old phrases for a reason. A lot of people get caught in preparation and they like to live in the incubation of preparation. Why is that, Rich? We've had so many episodes. It's the fear of friction, it's the fear of pushback, it's the fear of denial. And I'm no different. I have a lot of fear of denial in me, but you learn quickly once you fail a few times, once you get rejected a few times, once you get left on red, it's the worst shit in the world, a few times, you kind of get over it and you just text the people who want to text you back. We've been there before. We both have said many times we've played the dating app game, we've done the social circle game, we've made friends because our friends have pretty friends, girls that are beautiful, and you work it. But there are a lot of days where you just go out and nothing happens. There's a lot of nights on hinge where you swipe, swipe, swipe and nothing happens. There's a lot of days on Instagram where you DM old friends who are now single and nothing happens. But what's the rule, Rich? The rule is one yes makes every no worth it. But you have to go through the no's to get to one yes. And we should unpack that phrase, Rich, because you have a happy family because you went through a lot of no's to get to a yes, right?
SPEAKER_01Yeah, bro, that's exactly right. And listen, this is the entire thesis of our brand and our business and our podcast, right? It's like this is why we named their failures, because we feel like, bro, this is such a huge unlock, is when you're able to deal with failure and friction and use it to your advantage, use it to improve and not let it dehabilitate you. I feel like that makes a young man move and navigate the world a lot easier than if you just face the fear of rejection, the fear of failure, and then you crumble and then you hide and you go into the shadows and you're just like, oh man, I'm paralyzed, like I don't know what to do. This girl said no to me. This job rejected me. I didn't get the promotion, I got laid off, right? Like, life is gonna throw a lot of shit your way. And if you don't know how to deal with this friction and the failure that comes from life, it's gonna be hard for you to just navigate these different situations. I literally just got off the phone with my son, where he was like, Man, I'm starting school tomorrow and I'm like, I'm nervous. I'm nervous about joining the JV soccer team. I'm nervous because I'm going to high school with contacts instead of glasses for the first time. So he has all this anxiety about like how he's going to be perceived in high school for the first time on the first day. And my advice to him was at the end of the day, you have to look at yourself in the mirror and be happy with what you see. So any changes that you're making should be for you and not for the external world. I'm gonna expect you to do certain things, your mom's gonna expect you to do certain things, your friends are gonna have certain expectations for you, but ultimately it comes down to you and what makes you happy. And like I said, you have to be happy with what you see when you look at yourself in the mirror, and that's the only thing that matters. And he was like, damn, dad, like you're right. So I think he has a little bit more confidence going into the first day of school. That's the same advice I would share with our failures listener, man. It's just like unlock the superpower that is dealing with failure because it's going to give you a lot of positive things for you to move forward.
SPEAKER_00All glory should go to the man who takes the risk. All glory goes to the man who tries to see what's on the other side of friction. All glory should go to the man who asks the young lady out on a date. You get all the glory. You have to be in it to win it. Your son didn't call you, Rich. His first year of school, where he's gonna be on the JV soccer team. He didn't call you and ask you, hey, maybe I should start next year. Maybe I should start soccer next year. We should get a trainer. You know what? I don't want to wear contacts. I'm gonna keep the glasses because I feel more comfortable. And you know, I have that issue with my left eye, and I don't want to do the contacts in yet. I want to wait. What would be your response to him, given everything you know as a man and everything you know about our community, about people that love to hide in their progress?
SPEAKER_01Yeah, listen, this is exactly what I told him is like you have to do the things that make you happy in order for you to move forward, right? Like, I think a lot of guys they're dealing with a lot of deep-rooted issues, right? There's some deal with trauma, some have anxiety and fear of rejection, uh, some are not happy with their appearance or the way they look or have social anxiety or deal with loneliness or deal with depression. Like, there's a lot of things that young men are going through today. And I don't think we, you and I just ain't have a blanket answer to solve everyone's problems. But what we do know is if you adopt these basic principles of learning how to deal with rejection, dealing with failure, dealing with being told no, and you're able to eat that, gobble that bitch up, bro. Eat a no and be like, all right, cool. I'll try again next year, or I'll try again in six months, or you're telling me no now. I actually think you made a mistake. You'll see what I'm gonna come back with, right? Like, I feel like that's the way you should receive failure, right? It's not necessarily a rejection, it's a learning lesson. Yeah, it's an area of improvement, it's uh ammunition that you can take to propel yourself forward.
SPEAKER_00This is a note for all my high IQ know it all viewers. There is an opportunity cost that comes with delay in decision making. Our viewers are smart enough to know that opportunity cost is what comes with not taking action. These guys are smart enough to understand that when we're talking about crypto, when we're talking about NVIDIA, when we're talking about Tesla and their investment portfolio. It's a very smart community. But for whatever reason, Rich, they won't apply the delay in decision making and the opportunity cost that comes with never being ready. They don't apply those two. I gotta be honest with you, I'm 40 years old. I still don't have a family, I don't have a kid, but I sunk a lot of time and energy in preparing for this moment. If it was up to me, I would have started my family five years ago. But I delayed so long in giving myself a true deadline to a final number of savings, or me feeling comfortable like a real professional, because I have conflict in how I see myself. A lot of it is narrative-based. I used to see myself as someone that was poor, incompetent, someone who failed seventh and eighth grade, someone who rebounded from hundreds of thousands of dollars in debt. But that was the old story I used to tell myself. And as I got back into the dating market, Rich, I never really value myself the way I was currently. I didn't allow people to love me and accept me in the version of myself that I was currently because I kept looking backwards and seeing myself as my old self. And the way I used to give myself comfort was like, hey, I'm not gonna start a family until I find the perfect girl. I'm not gonna go on a date until I have all the money I need in order to take this girl out on the nicest dates ever. And you know what I learned, Rich, the last time I went dating and I'm happily in a relationship now? It's a messy process. There is no perfect answer. The same way there is no perfect answer in investing, there is no perfect answer in dating and finding your person. And saying finding your person is not even the right way to frame it. It's being comfortable to know that you have to align with somebody that's willing to align with you. And that time you waste trying to make it perfect, trying to make yourself perfect is bullshit because there is no perfect. No human on this planet, including your hero, including me and Rich, two people that you listen to weekly for advice, is not perfect. Your dad is not perfect, my dad is not perfect, no one is perfect. I have a rule. Everyone on the planet averages out of the seven. If she's beautiful, she's probably dumb as rocks. If she's ugly, she's probably got the best personality in the world. If she got a nice ass, probably God didn't give her good teeth. God is netting everybody out of the seven. Nobody is perfect. So this idea that you have to show up perfect, you have to be perfect in order to start something is a false illusion. And I know it better than anybody else, Rich. I really do. I took the path of least resistance to start a family. And now I'm in my 40s, living with a little bit of regret because I don't have the time to get back that I wasted. So just think about that for a second when you're listening to this episode. I have regrets at 40 years old, and I wish I could have used the time I had when I was young to simultaneously get started in my career, my savings, my health, my fitness, and also put myself out there to start a family. I didn't do that. I live with that regret. So I want our listeners to know we're not people that are trying to like shame you into progress. We're saying you have to get in the water if you want to learn how to swim. There's no other way around it.
SPEAKER_01Yeah, I agree with you. And you know, just I think the irony about getting prepared, especially when we're talking about the dating world, it's like you're getting fit, right? You're saving money, you're getting the stable career, you're getting the apartment. Feeling good. You're feeling good. You're feeling great, right? And then you go and date, right? You're on dating apps, you go out on the dates, and then you find that the women that you're dating, or maybe the one that you're most attracted to, doesn't care about any of the things that you've been self-improving on. She's actually looking for you to be a good person. Oh yeah. And be honest and be humble.
SPEAKER_00Yeah, she says, You got nice forearms, you got a nice smile. You're like, what? Yeah. What about my six-pack?
SPEAKER_01Yeah, exactly. But to your point, like that's why the alignment is so important, right? You work on all these things, you self-improve, you're in this mashing out self-improvement loop, and then you go into the dating world, and then you find that these women are actually not necessarily looking for the things that you've been self-improving on for the last couple years. So there's a disconnect there, right? Because they're looking for like the guy with the good personality, right? Like the guy with the good morals, the guy with the good family dynamics. And you're like, really? Like that's what you're looking for. I had that all along. I had that all along, right? But this is what happens when you don't get started, right? You had the thing that women were looking for all along. So I would highly encourage someone who is in that self-improvement loop to like just get started or do it in parallel, bro. Get fit, get your money, get your apartment, get your house. But in parallel, go out into the dating world and find your match.
SPEAKER_00Rich, I remember working at my first record label job, and he's currently still my manager. So this is about 60 years ago. And he's my mentor to this date. And he told me something that made me think about the young man in this episode. I was hired as a marketing manager to help artists roll out their albums and try to gain as much visibility as possible so people can know their music is coming out. And I remember I was so excited about being helpful to my manager that I wound up working on a spreadsheet for ticket buys, meaning an artist was on tour and I was collecting everybody's email in the company, and I was counting how many tickets that they ordered and how much money we spent. And anyway, long story short, my manager asked me, like, hey, I asked you for these five things three days ago. Why are they not done? And I showed him this spreadsheet of nonsense, something that had nothing to do with my job. But I was like excited about working on some non-consequential shit because I wasn't gonna get judged for it. And he told me something that stuck with me to this day. Do me a favor, stop working on shit that doesn't matter to the greater company. Stop swatting at mosquitoes and go and kill you a dragon. The dragon is the thing that needs to be done now. You know it, I know it. You're hiding in the garden fucking around with mosquitoes. This is not important. This is not gonna move the business forward. This is not gonna get you a promotion. This is not gonna get you more money. This is not gonna get you the apartment that you want to get. It's not gonna get you laid. Stop fucking around with mosquitoes and go and kill you a dragon. And I thought about this guy and the tinkerer and the over-optimizer and the guy that's like, uh, it's almost perfect. I can't wait to show everybody my business. The time it took you, two years, to put together the perfect business plan, the opportunity in that business is probably already left because your business plan is old. You're fucking around with mosquitoes, you're doing things that are not really important. Go and kill you a dragon. Go out there and do the thing that you know needs to be done. If you hate your job, quit your job, go do job interviews. If you hate your job, go work on your resume. Go get you a professional advisor. Take an action that's really gonna move this shit forward. You know what you're doing. You're fooling yourself. You're fooling yourself. You're confusing productivity as avoidance. You know it, we know it, Rich knows it, I know it, your mom knows it, everybody knows it. You look great, champ. You got enough money. Go out there, go ask a girl on a date. Go out there and get rejected. Who cares? Every no will eventually lead to the one yes that will make all the no's before that irrelevant. That's what we're saying on this episode. And you're not to blame. You are part of a huge generation of people that have the same problem, myself included, Rich included. So I don't want you to feel alone. We just want you to know stop fucking around with some mosquitoes and go out there and kill something, kill a dragon.
SPEAKER_01Yeah, that's exactly right. And you know, just when you think about the the guy that's over-optimizing himself, sometimes it's not necessarily his fault, right? Like in the sense that sometimes it's the content that you consume, right? Like we've spoken about this on many episodes where it's the comparison trap, right? You look at your current circumstances and where you're at, and then you go online and you look at your your feed, and it's just all dudes making more money than you with the sports car, with the hot girl, and you're like, nah, but I want that life. I need to work hard until I can have what he has, right? But you don't know how many times that man has been rejected or what circumstances he's had to get to his level, or more importantly, you don't know what illusion this man is selling online that you're digesting and thinking that that's real life. There's so much like misinformation and disinformation in the self-help productivity space, and I think these guys create a false sense of like a North Star. Like, this is what I need to be working towards, right? Because this is what every fitness influencer on TikTok is looking like. So I need to look like that too, right? And I think that that also becomes a trap.
SPEAKER_00Yeah, I mean, it's really you've created a cycle of avoidance, and that's really who we're speaking to. The guy that has normalized avoidance in his life. And what happens is you always hit reset because you're looking at the 0.001% of the internet that is doing the thing that you want to do at the highest level. Rich, if we're being honest, and I would love you to respond to this in the most honest way. How much does it annoy you that we started our self-development platform, our self-help platform called Failures a year ago? And when you're online, now that you can see the content of the number one through five in our category, it bothers me. I'm sure it bothers you. And it creates this unnecessary pressure to make you feel like we're never gonna get there and we're incomplete.
SPEAKER_01That's a natural emotion. I think once you start anything and you put a lot of effort into something and you don't really see the results that you're looking for or you're expecting, like naturally is discouraging. But I think the the reframe that I would share is just you gotta keep going, bro. You gotta keep going. There's gonna be so many uh pivots and iterations and changes and improvements and tinkering that you're going to make if you're going down the rabbit hole of creating a business that if you're looking at year one and year two, when you're 10 years in, you're gonna be laughing at these moments. You're gonna be like, damn, I didn't know shit when I first got started. Look at where I'm at now, right? Like the guy who started the car salesman job went a year without selling a damn car, or he sold like one used car off the lot to his best friend. But by year 10 in that business, when he's the top seller, when he's the top performer, he's laughing at that moment that he had to sell the hoopti to his best friend, right? So you have to have the ability to push through and persevere through things that don't necessarily feel like are moving in the direction that you would like it to. Yep. Because, like I said, hindsight is 2020, right? When you look 10 years out, 15 years out, the only thing that you hold on to is like, man, I'm glad I got started and I'm glad I didn't quit.
SPEAKER_00Yeah. Yeah, Rich, I do want to zoom into a community that exists in the self-help space. And I believe it's parasitical what they're doing to a lot of these young men. And Rich and I are not the prescription platform that is gonna keep selling you Tylenols and Advils, meanwhile, your leg is broken and you need surgery. We're not gonna keep serving prescriptions on failures. We're gonna give you a strong solution so you never have to come back to this platform. That is the business that me and Rich are in. And the reason why I say that is because I've identified a small pocket of the internet that lives and thrives off of giving our young men prescriptions. And this sector of the internet is 100% self-improvement before dating. That's the name of this category. And it's targeting men, convincing them that they have to be at 100%, whatever the fuck that means, self-improvement before dating. My response to that, Rich, is how can you be 100% self-improved when every human is a work in progress? This feels like someone that's capitalizing on this endless loop that you're never going to close, and they'll constantly be able to sell you something as long as you feel like you're not done. Exactly.
SPEAKER_01If you're viewed as this unfinished man, if you're viewed as this terminally ill man, then I could just keep selling you prescriptions, right? To help you numb your pain for a little bit. I can never cure you, but as long as I keep you ill enough and unfinished enough, you will keep buying this prescription and I will have a successful business because I'm the one that's selling you the prescription, right? It's extremely predatory at the end of the day. And I think even on the news, it just came out the Tate brothers are in jail. And when the courts looked into their businesses, they were like, Oh shit, the yacht was rented, the Bugatti was rented, oh, you actually borrowed the Lamborghini from another wealthy person. Really? Is that real? That's real, bro. Their whole like online internet image is a facade, like they don't have as much money as they're portraying to have. And if you're a young man who was following that lifestyle and following the Tate brothers, then you fell into the social media matrix of thinking that that's who you need to be. I need to be more like these guys, right? When in fact they were living a facade the entire time. So you gotta pick and choose what to follow, right? Yeah. This is what I was talking about earlier with like the comparison trap. You look at people that are selling a fake lifestyle and thinking that that'll make you the finished man if you reach that. But that's that's not necessarily the case.
SPEAKER_00Yeah. Rich, if we identify the Tate brothers as our North Star for someone who is selling a product, let's say they're not wrong. Let's say they were being genuinely helpful. And I I do believe some of the things they did say were helpful to a generation of young men. That aside, if I told you, hey, you need to be like me if you want to be successful and happy. And then naturally, what's the next question the person on the other end is gonna ask? Well, how do I become more like you? And what do I say? Buy this, and then you become more like me. But here's the news I'm gonna keep selling you a prescription. I'm never gonna solve your problem. Because if I solve your problem, I can't give you the be more like me advil. This is a loop that you have to recognize that you're in. And Rich and I have covered this topic in so many ways, but it's more relevant here because the young man that is ready to go, he's done the self-improvement, he's watched all the videos, he's read all the books, he's lost some weight, he's built his confidence, he took some communications classes online, he's built his confidence. What happens now? It's time to go out there and let the belt of life whip your ass into reality. And that's fine. Everybody has to expose themselves to friction. The biggest issue here, even if you remove dating, is why do I avoid friction? Because it's synonymous with a negative feeling that I have for when I was younger. And I don't want to feel the feeling of no. I don't want to feel the feeling of failure. I don't want to be embarrassed. I don't want somebody to know that I don't have the best car or an apartment. So I'm using it as a cope to keep improving so I never go and jump off the porch and try to take a risk. Rich, I do want to ask you a few questions that came up, and I think it's right in line with what we're talking about right now. Here are the top questions that come from a community of men that are suffering from trying to be perfect. Question number one What's the big problem? I'm just focusing on myself. I'm trying to get myself prepared before my opportunity presents itself.
SPEAKER_01Yeah, there's nothing wrong with that, bro. There's nothing wrong with that. I think to your point, just like we don't want you guys to be like us. We're sharing our failures, we're sharing all the things we fucked up in so that you don't make the same mistakes, right? So we're not speaking on high, we're speaking as two flawed individuals. Right now. Yeah. Yeah, right now, late 30s, early 40s, that have made a lot of mistakes. And we're hoping that in sharing these stories, you guys can extract the teachable moments from our failures, right? But going back to your question, just like there's nothing wrong with improving and spending time with yourself and like really locking in. Shit, I encourage that. I know family members who were weighing in at 350 pounds and just lost 100 pounds. And I just saw them at like a dinner and I was like, oh shit, like you locked in, right? There is nothing wrong with locking in and working on yourself. But we're strictly speaking to the guy who stays in that bubble and doesn't go out into the world and test this preparation. You've been getting prepared the whole time. But when are you gonna actually try to use these muscles? When are you actually gonna try to spend some of this money? When are you actually gonna go to the job interview to see if you're qualified? Yes. That would be my rebuttal.
SPEAKER_00Ask yourself the question. Think about it. What do I have to be to be ready? What is ready? Tell me more about this word. You keep moving the goalpost, you keep moving the finish line because you want to delay the friction that life has for you. If you are a young man that keeps waiting until things are perfect in order to ask someone on a date, until downloading a dating app, going outside and trying to meet people, if you keep waiting and waiting and waiting and waiting, just know that you're on a treadmill of endless self-improvement. Rich and I are saying there's nothing wrong with self-improvement, but when the self-improvement loop is endless, you're never gonna get off that treadmill. Keep in mind 40-year-old men right now, 2026, going into 2027, 65% of them took a survey and said, I am single. That is a crisis. That is not something you just move on from. When you read something like that, you fact-checked it four more times because you you can't believe it's real. Seven out of every 10 men walking around under the age of 40 are single. So where the fuck are all the other women at? Who are the other women dating? That's the real problem here. You have to hop off the porch. There are women available. There are women that want to meet you. If you're trapped in your room, how the fuck does anybody know if you're good or not? Are you the Ferrari in the garage? How does anybody even know your capabilities? How does anybody even know how fast you go? How does anybody even know how unique or funny or charming or charismatic you are? If you're sitting in a garage collecting dust, it's a tough spot to be in. And I just want you guys to know you're not alone. 65% of men are experiencing this, but you have to get out of the garage. You have to hit the road. You got to start showing people who you are.
SPEAKER_01You're the Ferrari in the garage with no gas in it. Because you ain't going nowhere.
SPEAKER_00You know what I'm saying? Like straight up. Yeah. You're perfect, but you're hiding.
SPEAKER_01Bro, I I think about the woman's perspective, ironically enough, right? And I could see her seeing this like what looks to be this perfect man, this perfect individual, very strong, financially stable man, right? But like, man, this dude fucks up all the time and never apologizes. Like, oh man, he leaves the dishes dirty all the time, never helps out with the chores, right? Tell me more. Sounds like a guy I know. And I'm saying, like, just a laundry list of things. And it was like, yeah, no, I am that guy. Yeah. I mean, shit, I'm that guy too, bro. But that's my point, right? Like, you spend all your time working to be this finished quote unquote man so that you could arrive to the date, a final product, or arrive to the relationship, the best boyfriend in the entire world. But guess what, bro? You're still a flawed individual. There's still gonna be things about you that your girl doesn't like, there's still gonna be mistakes that you're gonna make in the relationship, right? So all this over optimizing is great in the sense that you're improving, but when you're delaying the ass whooping of real life, like real life dating has nuances, bro. Like you can't just sit at home in your bedroom swiping on Tinder or watching fucking real world or any reality TV and be like, oh yeah, that's probably how relationships work. Like, mm-hmm. Nah, bro. Like, you gotta get in the field, you know, to understand like how these dating social dynamics work and how a woman is going to receive you and what she perceives you as, essentially.
SPEAKER_00Rich, I have another question. I'm 28 years old. I've gotten a lot healthier in the last two years, I've dropped 30 pounds. I just started the gym six months ago. I want to have some muscle and mass on me before I feel confident enough to go and date a woman because my last relationship ended very poorly and she made me feel terrible for my body, my weight, and how I took care of myself. So I'm a little bit nervous, but in your most honest opinion, why do you think I keep putting off dating until I'm ready? And have you ever experienced anything like this?
SPEAKER_01I have, bro. And I've made this mistake so many times. I could reflect on a moment just where I rented my house and I moved to a luxury apartment building, right? Mind you, I was dating my girlfriend when I had the house, but I was also dating her when I moved into the luxury apartment. And what I found was like I didn't need to move locations to ultimately end up with the person that was going to be my person.
SPEAKER_00You thought if you did this, everything would magically change, yeah.
SPEAKER_01Yeah. And I had the person with me the entire time, right? So I think it's important for you to certainly work on yourself and certainly do things that increase your confidence, right? Like, because you want to show up to a dating situation as a confident man, right? Like you feel good about yourself. But I think holding on to past trauma and saying, like, this is why I'm XYZ, I think that's naturally uh a negative headspace that a young man enters, right? Ultimately, like you said earlier, just I think people should receive you where you're at. And I think a woman believes that there's nothing more attractive to a woman than seeing a man that's work in progress, than seeing his discipline of waking up at 5 a.m. going to the gym every morning, right? Like that signals to the woman, like, hey, I might not have it all together yet, but I'm working on it. I'm working on myself. And not only are you saying that you're doing it, she's visually seeing you doing it, which is a completely different thing. I believe that the woman is more attractive to the guy that she sees working on himself than the guy who shows up with a six-pack and steroid up in quote unquote the final version of his uh appearance.
SPEAKER_00Yeah. If you're a guy out there that is obsessed with everything being perfect before you do anything, I want to teach you something about this word called work in progress. Let's break it down. Work in progress, not a guy that is just sitting at home letting life happen to him. You are working and you're in progress. Give yourself the grace of being a work in progress. Most fellow people who put work in and know it takes time to get to their destination will respect that. They will love you because you're a work in progress. They're not looking for you to be finished. And to be honest, most human beings that are alive and not six feet under the ground or in a pine box, we're all works in progress. That is the fear that you have. You think being perfect is the only way people are gonna love you, but it's not true. You're working and you're progressing. That's all life is. So once you can show someone that you have potential and you have a North Star and you have a goal, you have a one month goal, a three month goal, a six month goal, a five year goal, most humans. Most beautiful humans that are single and ready to fucking mingle or respect your gangster when they meet you and they see that you are doing something that has more ambition later. Because humans are humans, man. We see potential that we see in ourselves, we see it in others. If you're somebody that's a fucking lambong and you sit at home all day, you smoke weed, you play video games, you gamble, you're begging your mom for money, that is the guy that needs to be concerned. That guy we've spoken on in other episodes, he don't need to concern himself with dating or being in a relationship because he's not working and he's not in progress of anything. You, my friend, the guy who's afraid that the world is gonna hate you because you're not perfect, it's not true. It's a lie. What does one have to be to be ready? Ready doesn't mean perfect. If I had to share one piece of actionable advice, Rich, it would be to go out there not perfect and play the game even when you're scared, because that's when you improve, when everything is happening in real life and you're taking action and you're in motion. It's okay to play the game a little scared. That's a good thing. That means you respect the reward on the other end. And when everything is perfect, it's not worth it because it's perfect, and there is no perfect. That's the last thing I can say. Just take everything I just said and really think about it. You're a work in progress, and that's okay. I think most people who have achieved things will respect someone who's a work in progress.
SPEAKER_01Yeah, I agree. And I think a lot of the guys that are a work in progress feel embarrassed that they're a work in progress, right? And I think what we're saying is like, it's okay. It's okay to be a work in progress. It's okay to be uh self-improving and making yourself better. What we're saying is just understand that you can do that in parallel while you're also dating, while you're also working on your social life, right? Because I feel like it's almost like a scale, just if you look at it, if we try to visualize it, look at it as a scale, right? You self-improve, right? The muscles, the money, the house, the career, right? And the scale tips. And the lower end of the scale is like your social skills, right? Your charm, you're you're being charismatic, right? Now you're lacking in all of these avenues because you never get to flex those muscles, right? So we're just saying, even that scale out, right? Still continue to self-improve, but also work on other things that are gonna help you in the dating world because otherwise you will show up, not necessarily a complete man.
SPEAKER_00You know what I mean? Muhammad Ali has a great quote. I don't remember it, but the the thesis of it was I sparred in an empty gym for 10 years by myself, and it only took one minute in a ring to make up for all the time that I sparred by myself. That one minute in the ring with another person punching back changes everything because now you're not just dealing with the perfect plan, you're dealing with reality, you're dealing with life. You can watch people swim all day. You can listen to podcasts by Michael Phelps on how to become the best swimmer, but there's nothing more educational than getting in the water. Rich, I have one last question, which I feel really sad for this young man, and I feel like we have to answer it. Hey, got a question for you guys. Is it normal to feel like you're not good enough, especially when you're dating? I always go on dates and feel really bad about myself after the date. And I feel like the girl hates me or she's never gonna text me back, and I have a pit in my stomach until she texts me back. Second question: how do I stop being scared of rejection when I'm dating? That's a good question.
SPEAKER_01I think you have to remove all expectations when you're showing up in a relationship at the end of the day, or like a dating situation. I think naturally men carry anxiety when they enter the dating scene. Hell yeah.
SPEAKER_00I remember it. I remember getting ready. It's like you're meeting with somebody you don't know.
SPEAKER_01Yeah. Bro, you're going through, you're doing the works. You're getting a haircut, you're putting your best fit on. Should I text her now? Should I text her when we're closer to the date time? Yeah, making sure you got no food in your beard, like you're just going through all the checklists. And then you're hoping that when you get to the date, that it goes well, right? That you don't get to a car accident on the way to the date, that like um the food is good, the vibes are right, the drinks are flowing, right? Like, there's all these checkpoints that you're trying to check off, but you also have to remove the idea that, like, damn, I'm I'm trying to get laid after tonight. Obviously, that's the end goal. And if you're like serious about the woman, a relationship is the end goal, right?
SPEAKER_00Yeah, yeah. But if you spent $250, you're trying to fuck, but carry on.
SPEAKER_01Let me tell you something, bro. This reminds me of a very specific situation. You know, when you raise your eyes like that, I know you're about to lock in on a real nah, because I'm still tight about this to today, but when I was dating, I was dating this girl, and I was the quote unquote fit guy, stable job, had the money. And one of the things that I did because I felt like I wanted to show this girl that hey, you're with a guy that has money. Was we would go double date, triple day, you know, just group activities. She would bring her best friends and we would hang out, be at like six of us. Go out to drinks. Bill comes out to 300, 350. I got it. They're looking at me like, you got it. Like, the whole bill? Are you sure? Yeah, I got it. Don't worry about it. 350, boom. I'm that guy. I'm that guy, bro. I did that twice. Negative 700 in two weeks, and guess what? I'm not with that woman. What was I flashing for? What was I trying to prove? That's what we're telling this young man.
SPEAKER_00Like, I know it's late in the episode, but we actually stumbled and unlocked something we have to talk about, Rich. When you spend so much time in private building up your new version of yourself, something really terrible happens. While you aim for perfection, you start building a false identity around a lot of these things that could be a negative when you start dating. Because if you get your money up, you get your fitness up, you expect people to validate these things you work so hard on. But in your example, when it's not appreciated or validated and you don't get to be with the girl, it makes you angry because now you've built your whole identity on this false illusion that people are supposed to appreciate you as this money guy, as this fit guy. And if you don't get a compliment, it's fuck them, right? Yeah, I mean, that's my point. Your ego is weak, right?
SPEAKER_01You're sick. My ego was like, damn, bro, you spent $700 on this girl that you're just dating, and you didn't even end up with her, right? Like, and you don't even talk to the people who you bought drinks for anymore, right? So it's like, think about it. I feel like you don't want to say the names, but this is a real story. No, this is a real story, but yeah, man, that's my cautionary tale to the young guy that's over-optimizing, right? Like, you over-optimize, you show up to the dating scene, then you feel like you need to pretend to be this guy, but because bro, you over-optimize. So, like you convinced yourself you're perfect. Now everyone thinks you're perfect. You're gonna do the most, you're gonna show up to the day and start doing push-ups, and she's looking at you like, what the fuck are you doing? Like, I just want to fit. Look at me. I'm doing pull-ups in the fucking light post on the corner by the bar.
SPEAKER_00Like, like, what are you doing? Or you define yourself by your car, and all you want to do is, hey, let me give you a ride. Yeah, you're right. This is a very nuanced topic to begin with, but that's even deeper into it. I know because I've definitely been there before. You know what sucks when you go home, you clean your whole apartment, you tidy up your room, you wash the covers, and nobody comes back home with you.
SPEAKER_01Yeah, you just walk into a clean house by yourself.
SPEAKER_00You did all that for what? That's what we're saying. If you're a guy who's aiming for perfection in order to take the step in your life, it's a false illusion. Because in all that perfection is reality, and sometimes it's not gonna go the way you think it's gonna go because you assume everything is perfect. Rich, you didn't answer this part, which I think is important we should get to. This guy said he feels like he's not good enough to date. And I think that that's important that we have to address that. Do you think that in the trying to be perfect and taking years and years to get yourself right as a man, the core issue is that he just doesn't believe he's good enough.
SPEAKER_01I think all men naturally have something that they carry that makes them them. Some guys are the funny guys, some guys are the charismatic guys, some guys are just really smart, some guys love Jeopardy, right? Like whatever that nuanced thing about you that makes you special, I feel like that's what you need to show up as in any relationship or any friendship, right?
SPEAKER_00Yeah, what is good enough? What is good enough? What does that mean?
SPEAKER_01Yeah, yeah. And I think that for those guys that lack that self-confidence, I would say to them, it's like, bro, lean into who you are and present that to the world. Because, like we've said in earlier episodes, that's how you find your tribe, that's how you find the people that are attracted to who you are and the things that you like and your hobbies and interests, right? Like, that's who you need to be around. I think you have a false sense of reality when you're the nerdy guy and you're like, oh man, I'll never have a six-pack. It's like, yeah, bro, you're not the six-pack guy.
SPEAKER_00Be the nerdy guy. Also, you lied to yourself and you assumed. You know what's funny? We actually had a comment in our comment section that is exactly this. We did an episode that said, You need to move out of your parents' house if you really want to get some motion in your dating life. You want to put that shit in overdrive, you want to capitalize on all your dates. And what did the guy tell us, Rich? He's like, Do you know how much rents are today? And then he said, I got an apartment and I never got laid, so it's not worth it. And I think what we're saying in this episode is, who said that once you get to this level of perfection, that you're guaranteed to unlock everything? There's still more work after you lose weight, there's still more work after you get the apartment. And me and Rich have news for you. I'm 40. Rich is 38. We're in long-term relationships. Rich got a whole ass family. There's more work after that. It never goes in autopilot, it never goes into cruise control. So if a young man is asking us, hey, I never feel like I'm good enough, not even good enough to other people, let alone good enough to date, I would say this episode is actually not for you, young man. If you don't feel like you're good enough, you have a foundational issue you have to address. And the question I have for you is good enough for who? Who is this person that you want to be good enough for? Good enough means that you're trying to live up to something. To Rich's point, if the people you're around and the girls you want are expecting this much from you and you only have this much, then maybe you need to find yourself some people that are in this area, not in terms of money or status. We don't want you to shrink yourself. We're saying you're around the wrong people. You're not good enough for them, but you need to find the people that you're good enough being you. Show up as yourself, a work in progress, somebody that's improving, but good enough. That means that you lack the confidence of being in a group of people that don't even see any value in you. Bro, fuck those people. Find people who you are good enough for, people that like you for being you. And I know that can get weird when we start talking to our community because there are some underachievers, but be someone who's working that's finding people who love you for you.
SPEAKER_01Yeah, man. And that's exactly what this whole episode is about. It's just don't be the guy that's over-optimizing to the point where you're never ready to take the plunge and go out into the dating world or going out and trying to get that new job or seeking that new promotion, right? Like self-improvement is great, it's fantastic. We'll never tell our viewers to shy away from that. But when you're stuck in that bubble of getting prepared and you never actually go out and execute, and you never put gas in that Ferrari, you're never gonna move forward. You're never gonna get out of the garage. And that's what we're saying.
SPEAKER_00Imagine, just imagine, you spent your whole life, you spent your whole motherfucking life working to get yourself a six-pack, and you never get invited to any party where you get to take your shirt off, or you never get invited to a pool party or the beach. So you're just a lonely ass guy with abs in your crib. That's what we're saying. Metaphorically, the business plan guy has a six-pack worth of a business plan. It's perfect, but no one has experienced it. You have a lot of money, but you have no social skills. What good is that money? What is it gonna get you if you lack social skills? All these things in the world, they're nuanced and they all intermingle. They all complement each other. They're all symbiotic, they all have a purpose for different reasons. Don't try to perfect one thing and then be mad that the other 99 things about the world are not going in your favor. Here's the problem 99% of the world is not gonna go in your favor. It's gonna do what it's gonna do. Just show up as your best self. And like we said in the beginning of the episode, which I think is worth bringing back, Rich, don't spend your whole life becoming a man worthy of love and forget to let anybody love the man you're becoming. It's a double-edged sword. You gotta be sure that if you're gonna be worthy of love, keep yourself open for some love. Don't hide in your room. There's no gain there. There you have it, man.
SPEAKER_01Failures podcast.