The Unplanned Podcast with Matt & Abby

Episode: Breaking up, The Bachelor & growing up billionaire w/ Madi Prewett Troutt

Release Date: August 13, 2025
Guests: Madi Prewett Troutt & Grant Troutt

Overview

In this episode, Matt & Abby welcome newlyweds and first-time parents Madi Prewett Troutt and Grant Troutt. The conversation covers their whirlwind romance, the early joys and struggles of parenting, navigating public scrutiny, living with unusual privilege (Grant is the son of billionaire Kenny Troutt), and reflections on social expectations, faith, and finding purpose. Madi shares insights from her Bachelor experience, their breakup and makeup, and how they've grown as individuals and as a couple.

Key Discussion Points & Insights

1. New Parenthood: Early Struggles & Joys

• Adjustment to Parenting:

  • Madi and Grant discuss milestones with their six-month-old daughter, Hosanna.
  • Madi describes achieving a sense of deeper purpose as a mom:

    "For me as a mom, I feel like I've stepped into a level of purpose that I just didn’t even know was possible. ... stepping into motherhood was like a whole new level." (06:00, Madi)

  • Grant admits the early days were tough for him:

    "I feel like I’m struggling a little bit... Early on, the biggest struggle was, like, I would get her when she’s crying or to change her diaper. ... It’s so different for the dad." (06:21, Grant)

• Sleep & Travel Challenges:

  • The guests share stories about baby sleep regressions, travel mishaps (blowouts, getting puked on during flights), and how quickly things can change with young kids.
  • Madi shares a relatable mom mishap:

    “She had a blowout all over me on the plane. Didn’t bring extra clothes for myself... I was covered in poop.” (04:25, Madi)

  • Grant finds travel with a baby to be “humbling” and “good for character development.” (05:30, Grant)

• Parenting Hacks:

  • “The Happy Song” is a go-to for soothing their daughter mid-scream:

    "Literally, mid scream, she hears this beat come on... She's quiet. It's unbelievable." (13:46, Grant)

2. Love Story: Blind Date to Parenthood

• Timeline of Relationship:

  • Met on a (not-quite-blind) date: December 3, 2021
  • Engaged after seven months; three-month engagement; married in October 2022
  • First child born in early 2025

• How They Met:

  • Set up by mutual friends, but Madi found out who Grant was in advance through Instagram stalking:

    "I peer pressured my friend... She told me, and then I stopped him on Instagram." (25:45, Madi)

  • Grant had seen Madi at his church months earlier:

    "I look at her, she's wearing these Jordans. ... My friend was like, 'That's Maddie. She went on the show, like, don't even bother.'" (25:58, Grant)

• First Date Vibes:

  • Both were nervous; Grant was so anxious he forgot to open Madi’s car door—an immediate faux pas for her southern family’s standards.
  • Madi recalls knowing Grant was “the one” an hour into their date:

    "I literally texted my mom... 'I’m gonna marry him.' Like, this is my husband. And this was like, an hour into the date." (28:43, Madi)

• Quotes on Knowing the Right Partner:

  "In every relationship that I had been in prior to Grant, there would have been some little thing in me that felt like I was gonna settle... With Grant, it just felt like full confirmation of, like, you're not gonna have to settle." (53:19, Madi)

3. Breakups, Makeups, and Getting Real

• Why They Broke Up (Temporarily):

  • Grant admits feeling intimidated by Madi's platform and public image, and wrestling with his own insecurities related to both wealth and fame.

    "There was some pride in me... that was like, 'Hey, mine’s the more honorable route, which is like, not a platform, choosing what’s not flashy.' And so I think when we were starting to come together, I was just intimidated by the platform." (55:15, Grant)

• The 12-hour Breakup:

  • The breakup happened right before Madi was to introduce Grant to her family at a movie premiere. Both families already knew about the split—awkward introductions ensued!

    "So I'm meeting everybody, like, hey, mama... They're looking at you like, who's this? ... a hole that just broke up with my sweet girl." (58:06, Matt & Grant)

  • After counsel from Madi’s mentor and an emotional night, they were back together by the next morning.

4. The Bachelor & Public Perceptions

• Madi’s Bachelor Experience:

  • She explains how intense public scrutiny and televised drama were deeply difficult.

    "I think there was maybe a moment where just essentially the conversation was like, I don't think the two of you make sense and you belong together. ... I very much remove myself from all things Bachelor. Even still to this day, like, I really don't talk about it a ton." (50:09, Madi)

  • A memorable on-air confrontation with a contestant’s family made a major impact.

• Grant's Perspective:

  • Grant has never watched Madi’s season:

    "I want to know this Maddie right here... I just want to know this, Maddie." (52:01, Grant)

5. Wealth, Generosity, and Identity

• Grant’s Upbringing:

  • Grant is open about being the son of billionaire Kenny Troutt and how that influences (and complicates) his identity and how others see him.

    "I forget that at times I walk in a room and that's attached to me. ... People will misassign things. ... When we meet people, at times it feels like we start down here, and it's almost like, 'Hey, prove to me that you're legit.'" (35:19, Grant)

• Lessons from His Father:

  • Grant recalls his father’s journey from homelessness to billions and what it did/not do for his happiness:

    "He said, 'Grant, I was homeless at the park with my mom. I went home after selling my company for $3 billion. The feeling didn’t change. ... Money and success only allows for you to look for happiness in a better neighborhood.'" (30:32, Grant relaying his father’s words)

• Counteracting Stereotypes:

  • Madi emphasizes how Grant intentionally seeks out and serves the overlooked:

    "He finds the person in the room that everybody else overlooks and he loves on them... He genuinely lives his life to serve people and to help people..." (39:09, Madi)

• Giving: Money vs. Time:

  • Both Grant and Madi discuss the greater challenge—and joy—of serving in person, not just financially.

    "When you have money, it's actually a lot easier to write the check and send it and not deal with any of it. It's another thing to give your time and go be with somebody and sit and get dirty." (44:12, Grant) "The most beautiful part of giving is when there's sacrifice... we're continuously processing... continuing to pray through that." (45:03, Madi)

6. Navigating Public Rumors and Criticisms

• Managing Public Misconceptions:

  • The couple has dealt with wild rumors (e.g., reports of a $4 million wedding) and inaccurate assumptions about their lives.

    "People even thought our wedding, we dropped like $4 million on our wedding. ... Was not our story, but we were blessed to like be able to do the wedding at his parents house." (41:12, Madi)

• Staying Grounded:

  • The importance of authentic friendships, advisors, and staying focused on what really matters amidst public attention.

7. Faith & Purpose

• Faith is a central theme—how it keeps them grounded, informs how they process hardship and privilege, and guides their life decisions.

Notable Quotes & Memorable Moments (w/ Timestamps)

• On Parenting:

  • "I think it's just been like, the best thing ever." (05:41, Madi)
  • "It’s hard to see that when you’re in the newborn stage... but it just keeps getting better." (07:45, Matt)

• On Relationship Clarity:

  • "From the beginning, I felt, you know, this is someone that I want to partner with..." (54:33, Madi)

• On Wealth & Fulfillment:

  • "My dad says, 'Grant, you can have the whole world and be so empty. ... Money and success only allows you to look for happiness in a better neighborhood.'" (30:32, Grant quoting his father)

• On Giving:

  • "That's the most beautiful part of giving is when it comes with a cost." (45:03, Madi)

Important Segments by Timestamp

• Parenting experiences: 01:32 – 10:27
• Relationship timeline & blind date: 24:03 – 29:29
• First split & reuniting: 54:45 – 59:16
• Grant’s background & beliefs about wealth: 30:02 – 40:23
• Public scrutiny, rumors, Bachelor experience: 50:09 – 53:19

Where to Connect with Madi & Grant

• Madi's Instagram: @MaddiePru
• Stay True Podcast: Madi’s own podcast
• Book: "Dare to Be True" by Madison Prewett Troutt (launch September 23)
• Grant: Off social media for a year

Tone & Takeaway

This episode is warm, authentic, and deeply reflective. The couples’ playful teasing and vulnerability about insecurity, setbacks, and privilege set a relatable and welcoming tone. Both Madi and Grant are candid about their joys and struggles, offering reassurance and insight for anyone navigating relationships, faith, and family—regardless of their bank balance or their past on national television.