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Home  >  Investing & Finance • Life Lessons • Money • Podcast • Self-Development • Sports • Travel  >  Lil’ Bro Got Hitched! (from Charleston, SC)
Posted inInvesting & Finance Life Lessons Money Podcast Self-Development Sports Travel

Lil’ Bro Got Hitched! (from Charleston, SC)

Posted By Jackielyn Posted on June 6, 2026
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My guest is Michael Loomis aka Lil Bro! He returns to the podcast after making his first appearance  last year at the Man Overseas Retreat in Costa Rica. This time we’re in Charleston for an even more special occasion—Michael & Elyse got married!

In this episode, we get into wedding preparations and the emotional rollercoaster that comes with that. Michael talks about his excitement as the big day approaches. Also his biggest concerns. We cover why they chose to wed in Charleston, South Carolina, and the balance they’ve struck between traditional ceremony and personal touches.

We discuss why Michael loves his job, the NBA, and his new bride (but not in that order—on the pod or irl).

Michael shares how he thinks about investing and the future of real estate. He also talks about the possibility of the newlywed couple moving to Charleston.

This conversation is full of insights on love, life, and God’s plan—he holds back, sometimes he don’t.

The lil bro I never had fills me with pride. And I hope you enjoy this conversation as much as we did.

Topics discussed:
  • Michael’s wedding weekend in Charleston
  • Wedding vows excitement & nervousness
  • Why Charleston was chosen for the wedding
  • Plans to possibly live in Charleston temporarily post-wedding
  • Michael’s work flexibility & spouse’s career as a realtor
  • Challenges of the Charleston real estate market
  • Future family planning & balancing work with parenting
  • Advantages & challenges of working with a spouse
  • Importance of separation & personal time in marriage
  • Concept of “PTO” or paid time off in relationships
  • Logistics of moving in together & renting out property
  • Spouse’s financial mindset & investment approach
  • Appropriate compliments for meeting someone’s spouse
  • Premarital counseling & marriage mentoring experiences
  • Conflict resolution & taking breaks during arguments
  • Value of affirmations & addressing underlying emotional triggers
  • How Michael & Elyse met
  • Spending money on first dates
  • Cultural, political, and religious contrasts between Portland & Nashville
  • Reason for moving from Portland to Nashville
  • Dating app usage & height advantages
  • Phone communication & maintaining friendships
  • Preparation for being present during wedding weekend
  • NBA playoffs
  • Victor Wembanyama
  • Top 5 all-time NBA players lineup choices
  • Biggest NBA draft disappointments
  • Portland’s history with Greg Oden & Sam Bowie
  • Meeting Danny Ainge & Kobe Bryant
  • Honeymoon plans in San Diego & Maui
  • Benefits of journaling
  • Michael’s creation of a 1200-day journal project for Elyse as wedding gift
  • Custom supplement manufacturing & personalization
  • Role of functional medicine in identifying root causes
  • Peptides & its health benefits
  • Traditional healthcare vs functional medicine
  • Peptide examples: LL37, SS31, KLOW, BPC 157, TA1
  • PRP, stem cells, and peptide production
  • Diversification with real estate, 401k, VTSAX, and money market accounts
  • Elyse’s investment in nuclear ETF & financial situation
  • Marrying someone with debt
  • Real estate investing & market conditions
  • Interest rates, BlackRock, and housing trends
  • House hacking strategy
  • AI & future of leisure time and work
  • Tech stock investing
  • Advice for young people on finding a spouse
  • Importance of personal growth & timing in relationships
  • Online dating advice for men
  • Marrying high school sweethearts vs dating widely
  • Costs of weddings in 2026 & personal wedding expenses
  • Michael’s favorite movie: “I Love You Man”
  • NBA arena & college arena dream attendance choices
  • Traveling to Eastern Europe
  • Cooper Flagg’s potential & playing style
  • Next Man Overseas Retreat locations
Books mentioned:
  • Rich Dad, Poor Dad by Robert Kiyosaki
  • The Compound Effect by Darren Hardy
Listen here:
https://www.manoverseas.com/wp-content/uploads/2026/06/michael-loomis-full.mp3

 

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Hi there! I’m the Man Overseas, a thirty-something-year-old from Houston, TX, who in 2015, took a year-long sabbatical from a lucrative sales job in the States to travel the world on passive real estate income.
After one year abroad, I discovered the FIRE (financial independence retire early) community, and have since become a proverbial card-carrying member.
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