Zach sits down with Adam Roach and Dana Gentry, a married couple from Charleston, South Carolina, who have spent nearly a decade building what might be the most strategically intentional relationship he has ever heard described on the show. Both are high-achieving entrepreneurs on their second marriages, and they arrive with real tools, real failures, and a refreshing lack of pretense about how hard it was to get here.

The conversation opens with Dana sharing that her first book, Restore: 90 Days to Intentional Living, just landed at number 14 on the USA Today bestseller list, which sets the tone for everything that follows. These are people who do not drift. From their annual January planning retreat to vision boards presented to the whole family, their approach to marriage looks less like a feeling and more like a decision they make over and over again. Adam, a communication-focused coach who played tennis in college, describes how they identified early on, with the help of a therapist, that they were both alphas and would need to figure out who takes the lead and when. That single insight has shaped the way they handle conflict, celebrate each other's wins, and divide the emotional labor of their relationship.

Some of the richest material surfaces around what it actually means for two competitive, driven people to stop trying to win and start trying to keep the ball moving. Adam draws a vivid parallel from the tennis court: in a match between two alphas, one will always dominate. But if the goal becomes keeping the rally alive, the whole game changes. Zach builds on this with his own framework for conflict, noting that the problem is never really about winning the point but about whether the relationship is the court or the casualty. The episode closes with two practical tools that listeners can use immediately: the feel it or fix it check-in before someone unloads on their partner, and Zach's version, do you want to be helped, hurt, or hugged.

Key Takeaways

Second marriages can thrive when both partners are honest about what went wrong the first time and intentional about not repeating it
When two alpha personalities share a relationship, they need to decide who leads in which lane. Defaulting to whoever is more passionate or skilled in a given area works better than trying to win every room
The seven-day rule: no more than seven days apart without one of you flying to the other. Proximity protects connection, especially when both partners travel
Before your partner starts venting, ask: do you want me to feel this with you or help you fix it? That one question changes the entire conversation
Zach's version: do you want to be helped, hurt, or hugged? The alliteration is easy to remember and the question is hard to skip
"Vegetable soup" conversations, where grievances from five different fights get stirred into one, are a sign you did not release the last point before serving the next one
Vision boards are not just personal. Adam and Dana make them as a family, present them to each other, and stay genuinely invested in each other's goals, not just their own
Seeing your partner as a true equal, not just a legal partner, is a prerequisite for the kind of mutual support that makes ambitious two-career marriages work

Guest Info

Adam Roach is a communication-focused entrepreneur and relationship coach based in Charleston, South Carolina. He is the founder of I Love Coaching Co., a coaching community, and brings a background in competitive tennis to his frameworks for conflict, communication, and resilience in relationships.

Instagram: @adamrroach Website: https://ilovecoachingco.com/

Dana Gentry is an entrepreneur, speaker, and newly minted USA Today bestselling author. Her first book, Restore: 90 Days to Intentional Living, published February 3rd and hit number 14 on the USA Today bestseller list during launch week. Her work centers on helping people stop drifting and start living with intention across faith, business, and relationships.

Instagram: @danaggentry

Book: Restore: 90 Days to Intentional Living, available on Amazon and wherever books are sold. https://restoredevotional.com/

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