Podcast Summary: Earn Your Leisure

Episode: “How Do You Bring Up The Conversation of Prenups”

Hosts: Rashad Bilal & Troy Millings
Date: November 24, 2025
Podcast: Earn Your Leisure (iHeartPodcasts)

Episode Overview

This episode explores the often-taboo topic of prenuptial agreements (“prenups”), focusing on how to bring up the conversation with a partner. The hosts delve into the personal, financial, and emotional complexities that come with considering a prenup, drawing on high-profile examples and their own outlooks. They discuss strategies, pitfalls, and the underlying motives behind such conversations, blending practical advice with their signature, unfiltered humor.

Key Discussion Points & Insights

1. Why Prenups Are a Hard Subject to Raise

Uncomfortable Comparison: The hosts liken bringing up prenups to asking about STD testing—nobody enjoys the conversation, but it’s important.
- “It's like asking somebody if they have an STD. Nobody wants to. It's an uncomfortable conversation.” — [05:38]
Social Stigma: Most people don’t have prenups because they don’t want to address the discomfort or feel it takes love out of marriage.

2. Making Difficult Financial Conversations Normal

Upfront Honesty: The hosts argue that hard conversations should happen early in the relationship, emphasizing that openness builds trust.
- “All the tough conversations you got to have in the beginning, though, for sure.” — [08:54]
Setting Boundaries: Discussing boundaries and expectations is vital, whether it's for finances or other aspects like conflict management during marriage.

3. Boundaries and Dealbreakers

“Three Strikes Rule”:
- One host jokes about reducing argument tolerance from five to three times (“three strikes and you out”) as a way to emphasize clear boundaries and dealbreakers in a relationship. [15:10]
No Arguments Policy:
- “I don’t believe in arguments. … We can have a discussion, but an argument… Public embarrassment or clout—gotta go.” — [15:30]

4. Framing the Prenup Conversation

Ask, Don’t Tell: Approach is important; the hosts recommend asking about opinions on prenups instead of announcing a demand to sign one.
- “I’ll ask a question. How do you feel about prenups? Your response will tell me what I need to know.” — [16:56]
Watch for Red Flags: Someone who strongly refuses prenups might raise concern about ulterior motives.

5. Personal Stakes and Asset Protection

Beyond Money: The hosts note prenups are about protecting meaningful assets, not just financial ones—like a cherished family home, car collection, or a company built from scratch.
- “My company could not be worth anything, but it’s still my company. … I have a house in West Virginia that my grandmother left me and I never go there, but that means something to me. I want to just protect that.” — [18:13]
If You Built Together: If a partner helped grow wealth, sharing is fair. But safeguarding individually earned or inherited assets is also reasonable.

6. Reframing: Protection for Both Parties

Mutual Protection: Emphasize that a prenup can protect both spouses—not just the wealthier one.
- “I want you to be protected as well. It’s in the best interest of both of our love. That's a fact.” — [19:01]

7. Celebrity Examples

Stephen Jackson Story: Recalls former NBA player Stephen Jackson’s wedding collapse over a last-minute prenup refusal, highlighting why clarity is crucial before the wedding day.
- “Remember he was about to get married to that girl, she said he wanted a prenup. Oh, yeah. She waited up until the day of the wedding.” — [17:42]

Notable Quotes & Memorable Moments

“Bringing up a prenup conversation is almost like...It ain't that hard if you...” — [05:12]
“If we argue more than these amount of times, you gotta go. These are rules. You gotta have boundaries.” — [14:37]
“For me, the prenup is not necessarily so much about money. It's basic principles and things I've worked for.” — [18:34]
“If we start from the bottom together, of course…we’re business partners at that point in time.” — [19:07]
“The grace, the time, and my tonality be fucked up. I’m like, no, you gonna sign a prenup?” — [19:33]
“You have earned my love—beside this paperwork. Baby, please, please. Hey. Respectfully, Earnest.” — [19:54]

Structured Timeline with Timestamps

[05:12] — Initial analogy: Prenup talk is like asking about STDs; addressing the awkwardness.
[08:54] — Importance of having difficult conversations early; setting the tone for honesty.
[14:37] — Outlining personal boundaries; humorous “three strikes rule” on relationship arguments.
[15:30] — Arguing vs. discussing; preference for calm communication.
[16:56] — How to broach the prenup topic: ask rather than tell.
[17:42] — Case study: Stephen Jackson’s failed marriage due to prenup timing issues.
[18:13] — Discussion on the emotional value of assets and the importance of their protection.
[19:01] — Emphasizing mutual protection in prenup agreements.
[19:33] — Acknowledging the sometimes blunt delivery and need for tact.

Tone and Style

The tone is conversational, candid, and often humorous, in true Earn Your Leisure fashion. The hosts approach financial topics with honesty and a touch of irreverence, making complex or “taboo” subjects accessible.

Conclusion

This episode navigates the “when” and “how” of discussing prenuptial agreements with a partner, highlighting that the core is not just about finances—it's about openness, mutual protection, and respect. Through anecdotes, practical advice, and real-world examples, Rashad and Troy encourage listeners to normalize tough relationship conversations for the health of both love and wealth.

Transcript

A (0:00)

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Bringing up a prenup conversation is almost like. It ain't that hard if you. I do everything back. It's like. It's like asking somebody if they have an std. Nobody wants to. It's an uncomfortable conversation. And most of the time, you're gonna. I like the hard question, though. You just gonna say, fuck it, Roll the dice. And don't say, look, listen, guys. Y' all don't say because condom rates have gone down drastically. Yeah. Like, it's almost non. Existent. Non existent. Yeah. Right. Yeah. I mean, we have the stats. They gave us the numbers. They gave us the numbers. So puts on condoms. Oh, heavy, heavy. Puts on feet. Put on latex. The latex and shambles. Y' all thought dogecoin fell apart. Boy, I ain't seen a dude with a condom in his wallet in 15 years. For real. That is a pause ring. But I was. See, I was seeing what he was. That's another narrative thing to you was going with you was like, I ain't see a dude with a condom. I was hoping you didn't say on. No, that would have been what we doing. The show Blackout has. Has been discontinued now. That would have been the season. I ain't been. Well, yo, I was hoping. I'm like, yo, nah, he ain't going to go there. He ain't going to go there. You in the wallet. You tried to clean it. You tried to clean it real quick. For entertainment purposes only. Damn. I ain't been in the freak off stuff. Damn. Damn. Oh, man. But no, so bringing up the. Bringing up the conversation of a prenup, right? It's a very. Cause everybody says, like, you know, yeah, I want a prenup. I don't want a prenup. Very few people have prenups, which means that you're not even thinking about the conversation. You're not going through it. Because some people will say, like, it takes the love out of it, right? Like, if we madly in love. And it's like, hey, look, we need to have this conversation. I need you to sign this contract. And, you know, this is, you know, my lawyer. You know, look over it. See you comfortable with this. All the tough conversations you got to have in the beginning, though, for sure I may post mine too early, but I get to the Ernest, what's up? Look. Every now and then a tool pops up that makes you wonder why wasn't this around when I was struggling? That's Framer. If you've ever tried to design a website and felt like you need a coding degree, a design degree, and maybe a therapist, yeah, Framer said don't even worry about it. Framer already built the fastest way to publish beautiful production ready websites and is now redefining how we design for the web with the recent launch of Design Pages, a free canvas based design tool. Framer is more than a site builder. It's a true all in one design platform. From social assets to campaign visuals to vectors and icons, all the way to a live site, Framer is where ideas go live, start to finish. And here's my favorite part. Framer is a free full feature design tool. 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I don't believe in arguments. Oh my God. See on the same page like if I'm being good, you being good. We're loving each other. What is up? We can have a discussion. Hey, tell me. Hey Ian, I don't like when you know that girl was flirting with you at Invest Fest and you didn't clean it up. Okay, cool. I'll fix it. It won't happen again. But an argument or like public embarrassment or like clout, baby. Clout, baby. Gotta go. So I think for me, but you gotta have a conversation up front and be like, hey, for sure. For me it's not so much of like, I don't necessarily. I wouldn't say like, I say like, yo, if I get married, I want a prenup. And this is what I expect. I'll ask them, like, what's your views on prenup? So I'm actually. So if you get married, you get in the prenup or no. Was it mandatory? At this point in my life, of course. Okay. I mean, I've worked my whole entire life to get here. Right. To get here. Can't throw it away, so. I know, of course. But I, I, like I said, I bring it like. I'll ask a question. How do you feel about prenups? Your. Your response will tell you. Tell me what I need to know. Yeah. Cuz sometimes you could, you could tell somebody like, hey, I want to get a pre number if I get married. And they'll go along with it just because now you've already told them what you want. Right. So now they thinking, okay, let me just say whatever I got to say. And then just the Stephen Jackson move. Like what he went through. Stephen Jackson, What'd he do? Remember he was about to get married to that girl, she said he wanted a prenup. Oh, yeah. She went up until the day of the wedding. Yeah. For sure. So that's my thing. So I'm going to ask you how you feel about it. And I feel like, you know, if you say something to the effect of like, no, prenups are terrible. I'm not doing a prenup. Okay. That lets me know, you know. Yeah. Where you stand. But if you say something that I feel is a little bit more reasonable as far as like, yeah, I think that, you know, both people should be protected. You know, why should anybody be entitled to something that you haven't contributed to? Then that lets me know you're a rational person and you're not just in it. Could that be a finesse too? Well, it's not a finesse if you, when you sign the paperwork, there's no exception to that rule. Like, what if you met someone who maybe had more than you? Would you still force the prenup or. No, I just think that for me, the prenup is not necessarily so much of just money. It's like it's basic principles and it's things that I've worked for. So prenup could be like, they could take part of your company. Yeah. Your company could not be worth anything, but it's like, it's still my company. Yeah. It means something. You know what I'm saying? It might not mean anything to you, but it means something to me. Yeah. Right. I might have an old school car that, that was just my dream to get a Corvette. A 57 Corvette. That might not mean nothing to you, but out of spite in the divorce, you might take it. Right. Happened to Scottie Pippen. Exactly. So it's like, nah. Like this something, this means something to me. A card collection or whatever. Like, I have a house in West Virginia that my grandmother left to me and I never even go there, but that means something to me. I want to just protect that. Like, you know what I'm saying? So I feel like now if we start from the bottom together and we never had nothing and you help me get to where I am, of course. Like, you know what I'm saying? Like we business partners at that point in time. You, like, you've helped me, I helped you. Like, I'm not going to leave you stranded out. That's not good, yo. The grace, the time and my tonality be fucked up. I'm like, no, you gonna sign prenup? He asked the question. Then like, well, what do you think about. 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