Why Being Right Could Cost You Your Marriage

Summary

Podcast Summary: Earn Your Leisure – "Why Being Right Could Cost You Your Marriage"

Hosts: Rashad Bilal, Troy Millings (with frequent co-host Ian)
Episode Date: February 11, 2026

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Overview

In this episode, Earn Your Leisure delves into the intricate balance between success in business and success at home—the central focus being how the drive to "be right" can cost you in your most important relationship: your marriage. Co-host Troy Millings opens up about his personal journey as a husband, exploring the evolving nature of marital communication, vulnerability, financial partnership, and trust. The conversation moves seamlessly between practical money management in a marriage, lessons from family history, and the deeper, more nuanced aspects of love, support, and partnership, especially as wealth increases.

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Key Discussion Points and Insights

1. The Real “Keys” to Successful Marriage (02:35 - 05:25)

• Communication:
  • Troy emphasizes how he had to learn that communication isn't just about talking—it's about actively listening and truly hearing his partner.
  • "Every key doesn't open the same door. I think for me, the number one thing is communication... Early on in marriage, I realized that you winning means somebody's losing, and if you do that long enough, that person is going to start to feel a resentment." (Troy, 03:13)
• Transparency and Vulnerability:
  • Emotional and financial transparency are identified as foundational.
  • Being openly vulnerable is presented as a sign of maturity.
  • "Financial transparency, but emotional transparency, man, I think being vulnerable is something that shows maturity, and I've grown into that." (Troy, 03:50)
• Family Legacy:
  • Both hosts touch on the impact of observing long marriages in their own families, shaping their values and expectations.
  • "We've watched 50, 100 plus years of marriage combined between both of us... I was very cognizant of that. And it takes work." (Troy, 04:40)

2. Handling Joint Finances in Marriage (05:25 - 07:41)

• Practical Structure:
  • Troy details his personal and joint banking strategies: individual accounts for autonomy, a joint account for family/household, and business accounts as needed.
  • "I have a few bank accounts... I got a main account, but I have business accounts inside of that. And then we have, yeah, we have a joint account." (Troy, 05:38)
• Depositing System:
  • He describes a discipline of putting a fixed sum (e.g., $10,000/month) into a joint account for bills and family needs.
• Financial Trust & Frugality:
  • A notable dynamic: Troy's wife is notably conservative, often reluctant to dip into family funds even when her personal balance is low.
  • "She was like, I don't know. I didn't want to take money. I'm like, I love that about her because that she's super conservative..." (Troy, 07:15)

3. The Downside of Needing to “Win” in Marriage (07:41 - 09:09)

• No One Really Wins:
  • Arguments in marriage are different from debates with friends; winning can mean hurting, embarrassing, or building resentment with your spouse.
  • "Nobody really wins a debate because even if you win, you embarrass the other person." (Ian, 07:48)
  • "In a partnership, like in a marriage, the way I argue with you, I can't have that type of tone with my wife. I got to realize, like, how I'm coming across." (Troy, 08:00)
• Self-Reflection and Growth:
  • Troy highlights the importance of introspection—asking "why do I need to be right?" and prioritizing empathy.

4. Marriage Before and After Financial Success (09:09 - 12:18)

• Marriage Timing:
  • Ian prompts Troy to discuss whether getting married before achieving business success affected his approach versus what he’d do now.
• Prenuptial Agreements and Modern Realities:
  • The question arises: would Troy demand a prenup if he married today? His answer depends on the partner’s character and timing rather than money alone.
  • "If I meet her during the earn your leisure success, man. That's a good question. I probably still wouldn't, bro. Just the character of the person..." (Troy, 10:18)
• The Dating Struggle in Modern Times:
  • Both acknowledge the increased difficulty and skepticism in finding genuine connections in today’s environment—highlighting why his marriage feels even more fortunate.
  • "It's tough out here, man. I feel for my brothers. I feel. And for females, too..." (Troy, 11:21)

5. Trust and Support in High-Stakes Business Partnerships (12:18 - 14:32)

• The Need for Trust:
  • Troy explains that his wife’s support—even through risky business moves—was possible only because of deep trust established over years.
  • "This doesn't happen without, you know, the trust of my partner... The fact that she's involved in it, it makes it a lot easier." (Troy, 12:40)
• Encouragement through Failure:
  • She never doubted him, even after unsuccessful ventures, and the confidence this builds is invaluable.
  • Memorable Moment/Quote:
    • "[When I told her I was investing $100,000:] She looked at me like, okay. Like, no questions asked. Not like, yo, that's a lot of money, yo. You sure you want to do that?... She was like, yo, I, I watch how you work. I trust what you're gonna do. Like, I know if you're doing it, it's gonna happen." (Troy, 13:29)

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Notable Quotes & Memorable Moments

• On Communication:
  • "I've learned to become an active listener, and that's helped me out tremendously." (Troy, 03:30)
• On Marriage Not Being for Everyone:
  • "I don't say marriage is for everyone. It definitely is for me." (Troy, 04:30)
• On Arguments:
  • "If I win, at what cost? And why do I need to win?" (Troy, 08:40)
• On Transparency and Trust:
  • "After I had made the move [to invest $100k], I was like, 'yo, why you ain't have no feedback?' She was like, 'yo, I watch how you work. I trust what you're gonna do.'" (Troy, 13:35)

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Important Timestamps

• [03:01] – Troy’s personalized marriage advice
• [05:38] – The couple’s bank account setup
• [07:41] – On arguments and winning debates in marriage
• [09:42] – Would Troy do it differently post-success?
• [12:30] – The critical importance of support and trust in business and marriage
• [13:29] – Story of investing $100,000 with wife’s full trust

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Tone and Atmosphere

Laid-back and authentic, blending practical business talk with deeply personal anecdotes and hard-earned wisdom. The episode is filled with “friend to friend” candor and genuine self-reflection—balancing humor, warmth, and real talk about love, ego, and money.

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In this episode, the central message is clear: Being right in marriage is less important than being connected, open, and supportive. Real partnership, especially as entrepreneurs and public figures, is built on mutual trust, vulnerability, and a willingness to grow together.

Transcript

[Host]

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[Troy]

Right?

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[Ian]

Let's talk about, you know, like I said, you know, me and Ian, we. We have these conversations that's very controversial, a lot of different times, but they always say, like, why don't you talk to somebody that's actually married, right? So from a relationship started off a relationship standpoint, because people have been wanting to hear your perspective on a variety of different topics that me and Ian talk about. What is the key to having a successful marriage?

[Troy]

Ah, man, I think my key. I think everybody's key is going to be different. And that's one of those things. I see people giving advice all the time, and I'm like, every key doesn't open the same door. I think for me, the number one thing is communication is something that I've had to learn, you know, especially like us, we Pisces. So when we get in conversation, we debate and we go back and forth, we always trying to figure out who going to win the conversation. And early on in marriage, I realized that you winning means somebody's losing, and if you do that long enough, that person is going to start to feel a resentment toward even having conversation or having dialogue. And so what I learned about communication is that there's one way to listen. There's one way to actively listen. And so some people will say, like, oh, you listen to me, but you're not hearing me. And so I've learned to become an active listener, and that's helped me out tremendously. So communication is important. Transparency is another one. I know. I remember when we had the conversation, I'm like, yo, I'm get a joint account. And you were kind of like, yeah, yeah, I'm going to get a joint account. Obviously, I have my own account, and she has her own account. But I wanted to have something that's solidified that we can always look forward to. It's not who's doing this and who's doing that. It's like, yo, we're doing this together. So financial transparency, but emotional transparency, man, I think being vulnerable is something that shows maturity, and I've grown into that. You know, it's not something that we see in our community too much. It's not something that a lot of men talk about, but I feel very comfortable and very confident in that. And that's been some of, like, the easy keys to success, man. It's. I don't say marriage is for everyone. It definitely is for me. And I've watched it, right. Like, I feel like between us, like, Our parents, we've watched 50, 100 plus years of marriage combined between both of us. So we've seen the ups and downs of it, we've seen the goods and we see what a family unit could look like. And so I was very cognizant of that. And it takes work. I think every day I get to learn Danielle a little bit more and I take a challenge to learn even more about her because that's what life is about. We're going to grow, we're going to change, we're going to evolve. But I want to be part of that process with her and she's been part of that process with me. So. Yeah, man, that's some of it. I wonder how you look at it, man, as you, you've seen this relationship since the beginning, man, how we've been making this thing look.

[Ian]

Well, let's peel back the layers a little bit.

[Troy]

Yeah.

[Ian]

So let's talk about, okay, you. So the finance, that's it, That's a big topic. So you do. Okay, so you have all your, you have all your money in one bank account.

[Troy]

I have a few bank accounts. So I have a few bank accounts. Same kind of the, the method I deal with when I was investing, it was like I got something for options, I got something for long term and I got something just for ETFs and indexes. And so I got a, a main account, but I have business accounts inside of that. And then we have, yeah, we have a joint account.

[Ian]

So okay, you have your own personal account and then you have a joint account, right?

[Troy]

Absolutely.

[Ian]

She has a bank account. You have a bank account and then you have a family account.

[Troy]

Absolutely.

[Ian]

How do you decide how, what goes into the family account?

[Troy]

Oh, I put money in there every month. So let's just take a raw number. Right. And it may sound crazy, but let's say it's $10,000 a month. That money goes in there and it doesn't matter what happens, that money's going in there. That takes care of the bills, that takes care of kids needs, that just goes in there. That's been something I've been practicing even prior to getting married. I always, you actually taught me that early. It was like, yo, you gotta have reserves. And so that method of just having reserves has always been something that's been deep in my nature since my early 20s. And so as I got more money, I just increased the reserves. And so that, that savings account is something that just goes, money goes into there and we don't have to look at it, like, if she needs to pull from there, she pulls from there. She needs to pull money from another account. One of our. Because we have a business account together as well. If she needs to pull from there, it actually is not even an issue. You know, the crazy part is that she's super conservative when it comes to money. I think that's something that I take it for granted, but I'm truly grateful for it. Like, she won't pull from the account. Like, there have been times, and she gonna kill me for saying this, but she'll be like, Yo, I got $4 in my account. Like, why you got $4 in your account? Like, there's. There's no need for this. And she was like, I don't know. Like, I, I. I didn't want to take money. I'm like, I love that about her because that she's super conservative. But I asked him like, yo, you don't, you know, you don't have to do that. And she's like, yo, it's just this mentality that she's growing up with. Like, yo, make it. You know, that dollar stretch, right? You gotta be conservative with your money. You gotta be careful what you spend it. So even as we've accumulated more wealth, she still has that mentality.

[Ian]

Yeah. You said also about you can't win an argument because you. That's one thing when you learn in debates, like, nobody really wins a debate because even if you win, you embarrass the other person.

[Troy]

So that's it, though. But you use the word embarrass. I didn't even say that. I just said lose. But the way you do it. And I've learned this about myself, and probably we got this in common, right? Because we go back and forth, and nobody ever wins. We just kind of like, all right, conversations over. But like, in a partnership, like, in a marriage, like, the way I argue with you, I can't. I can't have that type of tone with a female. Like, I can't have that with my wife. I got to realize, like, how I'm coming across. And I think a lot of times people don't do that, right? Like, it's that retrospective. Like, you know what? All right, if I win, at what cost? And why do I need to win, right? Let me just see the perspective, because maybe I could be wrong. A lot of times I'm like, yo, I could have done that better, right? And there's times I'm like, you know what? Nah, I'm standing on ground on this. Like, I'm firm on this. I believe in this. But actually hearing it and having, like, that introspective moment to say, like, yo, you don't need to win this. Like, listen to this person's perspective. Because at the end of the day, I take that, J. Like, we not supposed to sleep with our backs turned, right? Like, we're not supposed to do that. Like, who wants to go to sleep with that? Because we're just going to wake up with the same issue. So, yeah, man, and being transparent and having that maturity to say, you know what? Let me hear what you got to say, right or wrong, and let's figure this out.

[Ian]

So you got married before, you know.

[Troy]

All this shit, a high level of.

[Ian]

Success and, you know, wealth and things of that nature. If you were to get married today, would you do things differently? Like, would you be more paranoid? Would you demand a prenup? Would you. Like, it's one thing to get married when at the beginning of your career. Yeah, it's nothing to get married when you've already worked 20 years and you've reached a certain level of success and you got a lot more to lose.

[Troy]

It's tricky, man. I watch my peers and I often wonder, like, yo, damn, man. Like, this shit is crazy out here. Would I do anything differently. With my wife now? I don't think so, because she. Because she's. She's been here before all this, right?

[Ian]

Like, well, that's what I'm saying. I mean, I'm talking about.

[Troy]

Not if I was. If I was today trying to get married. You asking?

[Ian]

Yes.

[Troy]

Oh, yeah. If it was her, I don't think I'd do anything differently. And the circumstances were the same. Like, I had known her, right? Like, we grew up and then we got married during the earn your leisure success. I don't think I do any. If I meet her during the earn your leisure success, man. That's a good question. I probably still wouldn't, bro. Just the character of the person, because I would have met her at a different stage of life if she would have matured and had life experiences. I don't know if I do anything different specifically, if it's her. If it's somebody else, yeah, man, things are going to look different. I'm watching some of these stories and I'm watching some of these relationships that a lot of my peers have, and I'm just like, yo, this shit is crazy, right? Like, even encounter having encounters with. With females, it's like, yo, there's a lot going on, but where's the Substance, you know what I'm saying? Like, I always say that to you. Like, it. It's tough for me to have conversations a lot of times because, number one, I don't want anything from anyone, right? And I think a lot of times I get missed. It can get misconstrued. Like, if you talk to the opposite sex, oh, he wants something from me, or, oh, you know, I need to get some from him. And I'm like, no, I'm just trying to pass time. And if you can, you know, stimulate my mind with the educational conversation, that'd be great. But other than that, I'm good. And I've seen it over and over. It's like 10 minutes into, like, a casual conversation. It's like, all right, this is going to go left. In fact, this is not even worth entertaining any further. So it's tough out here, man. I feel for my brothers. I feel. And for females, too. I feel for females. It's not easy to date. It's not easy to find someone that's your companion saying, it's not easy to find a life partner. It takes work. And the work is getting harder, man, because we grew up in a generation where, like, a lot of the girls, you know, we grew up around, watch their mothers especially, you know, my wife is Jamaican. So you watch that culture. You watch how your mother treats your dad, you watch how they take care of their dad or they take care of their family. It's a different environment. And then that just gets, you know, matured, and that just grows into how they're going to treat, you know, their future mate. So we. I'm pretty lucky, man. I'll be honest. I'm really lucky.

[Ian]

How important is it for a significant other not to be overly bearing and question somebody that they're with? If they with somebody that's. That's in business.

[Troy]

It'S important. I think it comes with trust, though, I think. And that's something that's developed over time, I think, you know, having that. That level of security and what, you know, your significant other is doing is vitally important. I always say, like, this. This doesn't happen without, you know, the trust of my partner. You know, I imagine if she said, yo, we, you know, I don't feel comfortable with y' all recording in the dining room, like, you know what I mean? Like, what do we do? And the fact that she's involved in it, it makes it a lot easier because she understands the tugs and the pulls and the gives and takes that have to go on inside of the business. And so, you know, I, I, I would encourage everybody to support. I know it's a lot of times, like, yo, he tried this thing and it didn't work, or he, he's trying something again and it's not working. Yo, hey, you gotta stay with him. You gotta figure it. Like, if, if you ride it with him, you gotta stay with him because you gotta believe in his, in his vision wholeheartedly. And I'm living the living proof of that, right? Like, we've tried a couple of businesses, right? Like, it didn't work. And she never looked and said, yo, Troy, stop trying. She was like, yo, I support it, even to the the point I'll tell the story about when I invested. And I was like, yo, babe, I'm going for it. She's the first person I told we were staying in LA in, in July 2020, and I forget it was me. And you sat down at the table, it was like 6:30 in the morning. I told her right before I came downstairs that I'm going for it. She was like, what? I'm like, I'm putting a hundred thousand in the market today. And she looked at me like, okay. Like, no questions asked. Not like, yo, that's a lot of money, yo. You sure you want to do that? It was like, okay. And after I had made the move, I was like, yo, why, why you ain't have no feedback? She was like, yo, I, I watch how you work. I trust what you're gonna do. Like, I know if you're doing it, it's gonna happen. Every time you say you're gonna reach a goal, you reach it. And so that level of trust, that little support, it builds confidence, right? Like, it feels like, yo, I don't care what anybody says. She believes in it. And like, her life is going to be impacted by it the most. Let's go. Let's rock.

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[Host]

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