What If “I’m Proud Of You” Is The Legacy?

Father’s Day is coming up, and we start where a lot of families start: socks, ties, and the jokes about low expectations. Then we get into what’s underneath the humor, because fatherhood is not a punchline. As a father and son, we talk candidly about what it feels like to carry provision and protection, and why dads often do the most while getting talked about the least.

We also dig into the father you have versus the father you want to be, especially through the lens of a Black family and a baby boomer generation shaped by survival, war, and history. That context does not excuse every gap, but it helps explain the restraint, the discipline, and the “stay power” that kept many homes together. We ask a hard question about discipline too: would you rather have your father correct you, or the police? That one point reframes fatherhood as protection, not just punishment.

Then we shift into what a father’s love looks like in real life. We talk about approval, sacrifice, and why “I’m proud of you” can hit different when it comes from your dad. From there, we go practical: building a financial legacy, creating ownership, and developing systems so money does not disappear with one generation. We even connect it to mindset and leadership, because the first CEO job is being the CEO of your household.

If this conversation hits home, listen all the way through and share it with someone who needs it. Subscribe, leave a review, and tell us: what’s one thing you wish you could hear from your father today?

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Transcript

Father’s Day Weekend And Gifts

SPEAKER_02 0:06

Welcome to another amazing episode of Pops and Son Conversations. And as always, your favorite father and son duo. It's me, Robalooy, favorite hill fox.

SPEAKER_01 0:18

And it is me, Daven, aka Trajectory Times.

SPEAKER_02 0:24

And here we are.

SPEAKER_01 0:26

Here we are.

SPEAKER_02 0:27

Okay. So we're going into the weekend of Father's Day. Yeah. And uh I look forward to my socks and ties. Come on now. At least give me a pack of draws, man. Yeah. But listen, Jay, we I I personally I don't mind those type of gifts. Give me the draws. Give me some socks. Give me some V-necks, some T's. Like I'm gonna make the best out of it. And it's a shame that you know we have low expectations for Father. Is that fair to say, Jay, that we have low expectations on gifts?

SPEAKER_01 1:11

Uh is it fair to say? I would say so. Yeah, I I I think it's fair to say that. Um because I never seen a lot of extravagant Father's Day gifts. It's just not happening.

SPEAKER_02 1:28

Now look, now look, Jay, but but keep in mind, so even in the celebrity world or the or the extremely wealthy world, it's almost like okay, if they get an extravagant gift, they kind of bought it, right? It kind of came out the account.

SPEAKER_00 1:46

Hey. That's a great point.

SPEAKER_02 1:50

Who is buying uh a father uh a house for Father's Day? Like who's doing that? Who's buying land? Nah. Nobody doing that. Okay, I I was waiting. I was waiting for a legitimate answer, man. Maybe maybe. I mean, I'm sure it's out there somewhere, man, but it is definitely not advertised. And uh, I think it's very rare. However, let's uh let's give people what they want. So we're here, pops and son, having a conversation. We're talking about what is it like being a father, um, grandfather, grandson, just just the whole realm of uh the manhood attachment or the malehood attachment of being a father. And uh again, you know, uh owe you guys 10 minutes uh of uh non-rant, of rant-free conversation.

SPEAKER_00 2:47

Honey, yeah.

SPEAKER_02 2:48

Rant-free. So uh so Jay, let's let's just kind of jump right in because uh we we also have a few questions that we got uh from our our our listeners that we want to address before this episode is over. So uh let's pick up where we left off.

SPEAKER_01 3:04

Okay, yeah, let's do it. So where where exactly did we leave off? Um oh yeah, we kind of talked about uh you know the father you have versus the father you want to be. Pop, she didn't really answer that question, though. I guess you know, I didn't.

SPEAKER_02 3:24

Uh well, you know, that's a really touchy subject for me because um, you know, my dad, your grandfather is uh he's 82, so we're blessed to have him. You know, but he he's that baby baby boomer generation, and you know, uh especially as a black man, as a black family, you know, the baby boomers, they they were born in the 40s, Jay. Can you imagine that in the 40s? I can't imagine it to be real. So when you think about the 40s and you think about history, when you think about civil rights, when you think about Jim Crow law, I mean I'm I'm gonna go all over the place. You know, when you start thinking about uh those type

The Father You Have Versus Want

SPEAKER_02 4:09

of things, you know, that generation has endured so much. Yes, from an historical standpoint, from a traumatic standpoint, uh spiritual, emotional, physical. You know, these are the the fathers that were drafted in the war. You know, they wasn't like, hey, let me go get the GI Bill, let me go get these benefits and come on back to my family, you know, unscathed. They were drafted. So you gotta think about the the mentality and the emotional uh aspect of that. When I said all that to say that uh, you know, my pops is an amazing man. He's given me what I would consider the um the uh consistent, disciplined, hardworking man. You know, he's shown me what that is like. Uh he showed me the bandwidth to to be with uh you know his bride, my mom, for uh over 50 years. You know, last month they celebrated uh 50 years of of marriage. And you know, they've been together you know over 60 years. And so, you know, that's a very loyal generation. Yeah. But but what comes with that what comes with that is uh a lot of sacrifice. You know, they had to sacrifice uh, you know, their their freedom. You know, they had to sacrifice uh I'm I'm sure uh restraint, you know, uh just for the story.

SPEAKER_01 5:50

Right a lot of restraint.

SPEAKER_02 5:53

Yeah, and so I mean these are things that that you and I probably wouldn't be able to do. We just don't just wouldn't have the bandwidth to be able uh to do that, um, being in the era and generation that we're that we're in and knowing what we know. Um, but you know, back then it's like uh straight survival mode. It's uh that's kind of what it was. So I say all that to say um, you know, I take so much honor and uh pride of of my dad and everything that he has you know endured. Um you know, being somebody that has uh that was in you know wartime. We're talking about Vietnam War, you know, being able to uh survive that and come back to you know a family and still you know raise a family. Um it's extremely remarkable. Um so so there's some things that I know that he desires to impart uh with me, uh with your uncle, my brother, and uh, but I I just don't know if you know he he can articulate it because you have to suppress some things back then in order to survive. You have to suppress some things, right? Like you you can't express all your experiences, all your feelings, um with without um you know just just knowing that it may be some things that emotionally and spiritually you can't control on on how you are gonna respond and react. So uh that's why it's it's such a emotional thing to say, but um I I feel like you know my dad showed stay power, which is rare. Stay power in the family is is rare, and we had talked about that last episode because you know, sometimes for the betterment and the overall safety of the dynamic, yeah, you know, the fathers were sliding. You know, they they were sliding, and um, you know, each each situation is different. You can't really judge somebody's situation because you don't know you know what it took and uh how they got to where they did, but you know, things uh things happen to work out and and you make those adjustments. So uh, you know, very very special generation when we start talking about the boomers. And so uh they had the stay stay together power. Uh as far as a father, they're they're very traditional in the disciplinary. They there was more of kind of like the fear factor, Jay. Like, you know, mom can say some things, right? Uh and and of course, you know, mom's first line of defense. But when they start saying, hey, you know, your granddad or your dad, I'm gonna let them know, then that kind of that kind of changes things, man. And so that's kind of how it was for me, you know. Uh we wouldn't try mom often, but uh just being kids, you're gonna try your mama, right? We all just try right, it's just the nature of uh of uh the kids, and so yeah, man. I remember Pops, man, being the reinforcer, and you know, he he'll come in and hey, lay the law down, man, whatever that means. You know, good things there's not a statute of limitations, man, because a lot of fathers be locked up.

SPEAKER_00 9:29

Jeez, Louise, it's like that, and that's the way it is.

SPEAKER_02 9:35

Well, but you gotta think about it too, Jay. So would you rather have your father disciplining you,

Discipline, Fear Factor, And Protection

SPEAKER_02 9:40

or would you rather have uh the local police?

SPEAKER_01 9:43

Nah, definitely father, you know.

SPEAKER_02 9:45

You know what I'm saying? Like at least you know keep it in house. Your dad don't want you to get in any worse trouble, and and he still wants you to live through it.

SPEAKER_01 9:56

Yeah. It's hurting him more than it's hurting you.

SPEAKER_02 10:01

It it does, right? It does. So uh, you know, um, you know, I'm thankful for you, you know, and your sisters. You know, I I I was a parent. I was a parent early on, and so um, you know, there was no cookie cutter approach. I didn't know what was going on, but I knew that there needed to be provision. Yeah, right. Uh so I never ran from responsibility or provision. Uh, if anything, I I just wish that I had more resources, younger, and more tools to pass down to my kids so that when you when you guys was, you know, by the time you guys was 18, man, you had you had a nice little stash. That's kind of one of my regrets, is uh not knowing or not researching or not really being aware um how to set the the family up um financially. And you know, obviously uh that wasn't passed down to me either, and it wasn't passed down to my parents. And so, you know, thankfully, you know, we have the capability, the resources, and tools now to rewrite the legacy. So, um, you know, those will be the main things, Jay, um, that uh that that I look at between, you know, my father, that that uh child rearing, and me now is just just uh building a stronger uh resource and tool um opportunity. And I think that's something that even in our community, something we can always do better.

SPEAKER_01 11:33

Yeah. Yeah, no, that's that's definitely good. That's good, Pops. Um yeah, you know, when when we talk with these subjects. You know what I mean? It's it is kind of tough sometimes to talk about in comparison. Because even now, when I was doing my my comparisons, it was kind of, you know, I don't know. This is kind of tough when you when you get to, you know, thinking about because one one thing that I have learned though is always consider your parents and the life, you know, they lived or what, because you never know. Like I think a lot of times, like is as kids, we can be kind of selfish about you know what they did

Provision First And Financial Regrets

SPEAKER_01 12:19

or what they didn't do. But then you grow up and you start living life and you have your own kids, and then it's like, oh, okay. It's not that easy, you know what I mean? So it's not that cut and drop. Exactly. You know what I mean? So it just gives you that better understanding of you know how things could have gone down or you know what I mean, just how tough and difficult it can be. Uh so grace is always uh that grace is always there.

SPEAKER_02 12:48

Yeah.

SPEAKER_01 12:50

Um but yeah, well, Sue, what what what what can we go from from there though? What you want to talk about?

SPEAKER_02 12:56

Yeah, um, you know, uh I always like to make sure that we mention uh the the uh the love, you know, the the love, the care, the support. Um, you know, we we talk about a mother's love, and and a mother's love is extremely important. Uh it's nothing like it. But I want to talk about the power of a father's love, Jay. Because when you when you think about a father's love, you know, it's one of those things that number one doesn't get mentioned a whole lot. No, not at all. No, uh they talk about absentee fathers all the time, deadbeat fathers. Like you hear more about deadbeat fathers than active fathers. Am I right or wrong?

SPEAKER_01 13:48

You're right. On which one you're right.

SPEAKER_02 13:51

Right. So uh I think when we talk about a father's love, there's a lot of sacrifice that comes with that because you have to you have to think about it. When you think about it, a father is uh he's a provider, you know, he makes provision, he's a protector. And these are things that he can do independently on his own. He doesn't necessarily have to have a family. You know what I'm saying? Like he will still be a provider, he will still be a protector. Yeah you know, it may be of uh you know his family. It doesn't necessarily have to be, you know, wife and kids. It could be of his parents, it could be of people close to him. He's always still gonna be uh a protector and a provider. There's no days off from that, right? And so I think that the sacrifice of uh you know just knowing what he has to do and knowing that he has to be accountable at all times. You know, um, I think that

The Power Of A Father’s Love

SPEAKER_02 14:50

you know, children more so look at a father's love for approval. I I think more so uh of approval because you know moms innately are uh nurturing. You know, they're always gonna make sure that you're good, they're gonna, you know, make sure that your spirits are high. And they don't even know the outcome or the results uh to come. But they're always gonna give you that cheerfulness, that joyfulness, and sometimes even on the other end of it, they're gonna give you that emotional stuff that you know uh can take you know different turns. But a father's love, man, uh I think is is so amazing because it affects a son and it affects a daughter differently. But at the same time, I feel like it also can literally change the uh trajectory, you know, of their attitude, of their spirit person, of their emotions, even from the physical aspect. Like it literally can be just that powerful. So um, you know, that's my state. So how do you feel, Jay, about, you know, uh the importance of a father's love and how it affects his family?

SPEAKER_01 16:03

Yeah, I think it's super important. Um just like you said, it it manifests differently. Um uh the father just has different ways of showing it. I will say one thing that I noticed, I don't know why it's like this. I I haven't found the explanation for it, but I I found that like, for instance, like when you say stuff like I'm proud of you, you know what I'm saying, just that one simple phrase, I don't know why it hits so much different. Like that phrase doesn't sound any better. It sounds the best coming from your pops, you know what I'm saying? I don't know the science behind it, you know what I'm saying? My mom has told me that she's, you know, different family members, yo, I'm proud of you, Jay, friends, all that. Why? I don't know why it hit different when it comes from your pops, man. Um and I think that's because um, you know, as men, we don't, uh, you know, a lot of us we don't say I love you like that, or we don't, or we just not like overly emotionally like, you know what I'm saying? Your mom is gonna, oh, that's my baby. You know, she gonna do all that. Your pop's not gonna do all that. But, you know, that phrase right there, that to me is like um, I don't know, that's that's the the phrase that kind of makes me feel like, yo, like it's a lot of love in that phrase, you know, even even more so than the than an I love you. I don't know, it's it's weird. I don't know, I don't know how to explain it. I don't know how to explain it with that. That's good. Um when I think about it, and you know, as I'm raising my son, like how do I like show show him love? And it's like I'm still trying to, I'm still even trying to figure that out for myself. Like, because you know, right now he's six, and you know, I mean, you know, I I tell him, you know, I love him. We, you know, he do that, daddy. I love you. I love you too, so whatever. But um I think the best way that I can actually show it is um, and I hate to say, you know, sacrifice is a big part of it. You know, that's just a big part of being a uh a man and a father in general. But I hate to say that that's my, you know, my waiters for love is just making all these sacrifices, but at the end of the day, it kinda is, you know, it it kind of is. Like the things that I that I sacrifice, um, it's all out of love. Like it's it's 100% because I love you. You know what I'm saying? Like, it's it's just no way around it. Like I I make all these sacrifices for you. And um I guess you know, you really just hope that it translates because you know, like I said, like you said, like we don't get that um just just the same, the same way moms that that that that they do it, is just it's just different, man. I don't I don't know. I don't know. But like I said, like for me, I I it's it's in the sacrifice, and then you know, just that I'm proud of you, it's just uh I guess how I would say um how I show, you know, how I showed up. Um but you know, I'm it's a work in progress. I'm still figuring that out.

SPEAKER_02 19:36

Yeah, that's that's the beauty of it though, is to you know, navigate, you know, take the things that you've learned, take the things that you're learning, and discover, you know, new ways and uh adopt new tool tools and and resources because you know when we start looking at our community, we start looking at our generations, I mean, one of the biggest things we have to take into account is uh just the economical impact.

SPEAKER_00 20:05

Yeah.

SPEAKER_02 20:05

Right. Like if if uh the generations before us have been broke or rich, then you know, we need to uh literally carry the torch and and make sure that uh not only do we scale, but we just make sure that you know we don't regress, you know, as our generation comes in and makes impact. And uh, you know, I'm thankful that you know, a strong work ethic. We we uh our lineage have a strong work ethic and um you know uh can stay pretty focused on task. But we're in an era to where we have uh an opportunity to do some loop supernatural stuff, like literally change the trajectory, you know, of the of the legacy. And you know, I've been you know focused on you know just finding different ways to for ownership, you know, not so much of a financial situation because I know that'll come. And you know, we can we can hit a lick and get you know 100k, 150k, but at the same time, we can run through that if there's no game plan and and if there's no system in place to where you know our uh generations to come don't have any type of turnkey

Ownership Mindset And CEO Of Home

SPEAKER_02 21:30

systems that we put in place to make sure that money stays, the money grows, and and and that we enjoy the fruits of our labor while I'm here. Because I I don't want to be the type to uh bust my butt, uh live as a minimalist just just for you guys to live as a millionaire. Nah, it's hey, we all gonna live good, man. We all enjoying the fruits of our labor, man. And even and even for you know the our parents and you know, your grandfather. Grandparents.

SPEAKER_01 22:00

Right, right.

SPEAKER_02 22:02

Yeah, we have we have an opportunity to do pretty good. Now, I would say one of the biggest challenges is having everybody on the same page. Not everybody's gonna feel it. You know, your your mama, your auntie, you know, your uncles, they they may not be accustomed to you know true ownership. They may not be accustomed to entrepreneurship, being small business owners, you know, and finding ways to uh you know build enterprises. Like when you think about it, Jay, these large corporations, Apple, IBM, uh, Amazon, and all that stuff, man, these are people that started this stuff. These aren't businesses that just popped out the blue. These were folks that was in their garage, in their living room, living out their cars, whatever the case was, and they built these empires. So there's there's no reason why we can't do that or at least strive to do that. At least give it a shot.

SPEAKER_01 23:00

Yeah, yeah, 100%.

SPEAKER_02 23:02

Right? Because small businesses don't have to stay small. If you're an entrepreneur, you don't have to stay an entrepreneur. You can be a part of a large corporation, you could be a CEO, CFO, you could be a vice president like that. That is not far-fetched, you know, and I think in our community, we really have to step up that uh belief system. You know, um, it's great to have a job, it's it's even great to be uh an entrepreneur and a business owner, but there's also levels. There's above that. And uh and Jay, when you think about it, and I always wanted to share this, uh, just from a business aspect. Um, you know, when people become CEOs of a Fortune 500 or Fortune 5000 or 500 Inc. uh corporation, they move from business to business. They're not the vice president for 30 years, they're not the CEO of a corporation for for 50 years. They once you're a CEO, that is your title. Yeah, so your your applications for another position at another company is gonna be CEO, right? Right, right. So right, you so you're not you're not gonna be the CEO of ABC Inc. and then go over here and apply for uh a management position, a manager.

SPEAKER_01 24:30

Nah, yeah, nah, you CEO.

SPEAKER_02 24:32

So so that's the power of it. And when we think about it, the the first CEO position is the CEO of our household, right? So let's take care of home first and then build uh from out there. And I think that's the play, Jay.

SPEAKER_01 24:49

Yeah, nah, profound, profound. I hope the listeners pick that gym up because I definitely did. It's a it's all about perspective and mindset, like you said, it's the belief system. Yeah, I think that's a big key about it.

SPEAKER_02 25:04

I think so too. Matter of fact, I think uh I think we should go ahead and drop uh a part three, man. Let's wrap this up and uh and let's let's make sure that you guys know and understand that. As we go into Father's Day, it's so important to honor our fathers. And then we and we know and we understand that there are some fathers not available, you know, whether they uh aren't here anymore, whether they're incarcerated, whether they are um deployed overseas, um maybe at your stepsister house this year. Oh not yours, but nevertheless, uh, you know, have some grace. You know, it's it's not easy, it's not simple. Um, and there's no cookie-cutter approach to being a father, but just know that you know there's a lot of love there, there's a lot of sacrifice, you know, there's a lot of major decisions that had to be made that you might not like right now, but it's it's for the greater good, you know, long term. So if you have to make those sacrifices as not as much time as you want, or you know, an additional day, or if they're out of town, you have to make up or listen, if your father's still around, man, just find a way. You know, find a way to to uh you know get past some things and because you you're gonna wish that you did if if you uh if they're no longer available, or you're no longer available to have those conversations for whatever reasons. So uh cherish those moments, man. Yeah, that's it. And uh that being said, look, we'll see you guys next episode, as always. Uh Hops and Sun Conversations. If you need to catch up on some episodes, handle that. But we will see you guys next episode as we finish up June, Men's Health Month,

Honoring Fathers And Closing Thoughts

SPEAKER_02 27:04

uh, Happy Father's Day from uh from your favorite father and son duo. It's your favorite still Fox Rob Malloy. We gone. Happy Happy's Day.