Win With Paid Ads, Ep. 84: The Hardest Parts of Running Businesses in Our Marriage

Host: Ashley Brock
Guest: Kyle Brock (Ashley’s Husband)
Date: September 4, 2025

Overview

In this honest, behind-the-scenes episode, Ashley invites her husband Kyle onto the podcast to discuss the realities and toughest parts of running businesses as a married couple. They candidly share their journey from broke college students to successful business owners, exploring money struggles, evolving roles, emotional growth, and how building businesses has affected their relationship and family life. Their conversation is relatable, humorous, and packed with hard-earned insights.

Key Discussion Points & Insights

1. How They Met & Early Relationship Dynamics

• College Basketball & First Impressions ([01:28]-[03:23])

  • Met playing basketball in college; Ashley jokes about being the better player.
  • Early dates involved humble offerings like PB&J and (rock-hard) biscuits.
  • Fun, playful chemistry, with a focus on family values.

• Financial Struggles & Contracts ([03:59]-[08:33])

  • Both started their relationship with little money and debt.
  • Ashley helped Kyle pay off debt but made him sign a contract (with interest!).
  • Story illustrates their practical approach and the importance of clear agreements.

  Quote:
  "I'll pay off your debt, but we're going to write a contract, and I want interest, baby."
  —Ashley ([04:51])

2. Money Tension and Frugal Beginnings

• Extreme Budgeting ([10:43]-[13:07])

  • Early jobs paid ~$30-36k/year; they lived together due to financial need.
  • Intense focus on saving, including couponing and fighting over $3 guac at Chipotle.
  • Money stress was a central source of conflict.

  Quote:
  "I remember getting so mad at him because he paid $3 to put guacamole on my Chipotle bowl. And I was like, I did not want that. That was $3."
  —Ashley ([11:42])

  • Humor about Ashley’s “crazy couponing” and embarrassing Kyle at the grocery.
  • Both agree: financial stress tested their relationship—but also built their resourcefulness.

3. Growth, Therapy, and Evolving Expectations

• “You Marry Two People” ([13:07]-[13:54])

  • Acknowledgement that people change after the wedding, and marriage is about growing together.
  • Recap of nine years of marriage, plus four years of dating, highlighting change and growth.

• Therapy and Emotional Intelligence ([13:54]-[14:25], [26:41]-[27:24])

  • They went to therapy at a pivotal point in their marriage; Kyle has continued weekly therapy.
  • Both have become more emotionally aware and communicative.

  Quote:
  "You come into a marriage with expectations ... If you get blindsided with the ‘holy crap, this is not what I expected,’ it's either going to cause a fight, divorce, or a deep conversation. And that's what we decided to do."
  —Kyle ([17:41])

• Role Reversal and Identity ([15:46]-[18:56])

  • Initially, Kyle’s career was the focus; once his insurance agency was stable, Ashley started her business—which grew rapidly and became the family’s primary focus.
  • Kyle opens up about grieving the loss of a “traditional” family role and feeling the need to adapt as Ashley’s business soared and she "out-earns" him.

4. Balancing Parenting, Business, and Guilt

• Delegating and Family Time ([18:56]-[22:47])

  • Ashley shares her struggle to juggle motherhood and business growth, including guilt about missing time with kids.
  • Practical solutions: delegating, creating “no phone zones,” and regular family routines.
  • Both stress that sacrifice and communication are ongoing necessities.

  Quote:
  "There's no person that has an eight-figure business that did it in two years, that didn't have to make some huge sacrifices and stress."
  —Ashley ([21:25])

• Challenges of Non-traditional Roles

  • Kyle handles more morning parenting; they have help to get kids up.
  • Adjusting expectations and resisting comparison to more traditional families.
  • Ongoing dialogue about time management and presence with the children.

5. Business Ownership: Freedom and Resentment

• Time vs. Money—What Motivates Each? ([24:39]-[26:03])

  • Kyle says his business goal was flexibility and time for golf, hunting, and family.
  • Admits occasional guilt when Ashley works long hours and he pursues leisure.
  • Ashley confesses resentment, knowing that she’s working to eventually “buy back her time.”

  Quote:
  "I think I was honestly just resentful because ... I'm working so hard ... and, like, he did the whole point of why we start a business so that he could have that time. And I think I was a little resentful that I couldn't be there already."
  —Ashley ([26:03])

• Self-awareness as a Relationship Tool ([26:21]-[26:56])

  • Therapy (“Dr. Phil”) has helped Kyle articulate feelings; both partners practice self-awareness and respectful communication.
  • Frequent, honest check-ins and knowing when to “take five” during heated moments.

6. Recurring Arguments & Lasting Priorities

• The Biggest Recurring Argument ([28:10]-[29:22])

  • It’s about time: How much they spend with kids and presence as parents.
  • Kyle’s top priority is making sure the kids feel their mom’s presence, not just “know” her.

  Quote:
  "I don't want to get to the point ... we have a net worth of $100 million, and my kids don't want to hang out with me. I would rather ... have the kids."
  —Kyle ([29:15])

• Money Can’t Buy Time ([29:22]-[30:10])

  • Both believe time with kids is more valuable than money, and are consciously designing their lives to balance both.

Notable Quotes & Memorable Moments

Hilarious & Heartfelt:

• “She charged me interest, too. … I'm like, is this how it's gonna be?” —Kyle ([04:57])
• “Just look at him, he's hot. The car, I just — I barely saw it.” —Ashley ([06:57])
• “She would have an envelope full of coupons ... stand there for 15 minutes ... I’d already go start loading the groceries in the car, like, ‘this is ridiculous.’” —Kyle ([12:03])

Deepest Insights:

• “You marry two people: the person you marry at the altar, and the person they become.” —Ashley ([13:07])
• “It came to a point where I had to grieve the loss of not having a traditional role family. Probably ego and pride takes a little bit of hit.” —Kyle ([16:39])
• “You can't buy your historical time back. That ain't gonna happen ... I don't want to give that up.” —Kyle ([30:10])
• “How can we have both? How can we be great parents, have great relationship and help a bunch of people?” —Ashley ([30:18])

Timestamps for Key Segments

• [01:28] – Story of how they met, basketball banter.
• [03:59] – Early money issues and debt contracts.
• [10:43] – Low-income beginnings, first jobs.
• [11:42] – Guacamole fight, money stress.
• [12:21] – Extreme couponing stories.
• [13:54] – Therapy enters the picture.
• [15:46] – Shifting business roles and expectations.
• [17:41] – Confronting nontraditional gender roles.
• [18:56] – Parenting struggles and delegation at home.
• [22:47] – The toll (and rewards) of business growth.
• [24:39] – Real discussion about time, freedom, resentment.
• [26:41] – Therapy’s impact and communication skills.
• [28:10] – Recurring arguments: The importance of time with kids.
• [29:22] – Closing thoughts on money and what really matters.

Tone & Language

The tone is casual, humorous, heartfelt, and deeply genuine. Both Ashley and Kyle are candid about their past mistakes and vulnerabilities, frequently joking about themselves and each other. The language is warm, conversational, and relatable—never preachy.

Summary Takeaway

This episode offers a rare, unfiltered look at how the realities of entrepreneurship impact marriage and family. Ashley and Kyle’s willingness to share their messy financial history, evolving roles, therapy journey, and emotional challenges makes for an engaging and highly relatable listen. It’s a reminder that behind every “picture-perfect” business owner is a whole lot of hard work, uncomfortable conversations, and growth—both personal and professional.

For entrepreneurial couples (or anyone juggling business and family), this episode is a must-listen for its honesty, humor, and practical insights about partnership, growth, and the things money can’t buy.