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.