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

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.

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)

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)

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

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.

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.