"Never stop talking about what feels fair or doesn't feel fair. It really should be an ongoing conversation that doesn't stop. That's just part of the dynamic of a living relationship." Our hosts, Natalie and Dan Slagle, chat with Kaylin Dillon. Getting married at 21 with a prenup she barely understood is what turned Kaylin into one of the leading voices on financial agreements between couples. What started as her husband's request to protect an inheritance became, years later, the foundation of her book, her course, and a practice built around helping couples have better money conversations before they say "I do." The word "prenup" still lands with a thud in most relationships. Kaylin reframes it not as a hedge against divorce, but as a Plan B that lets you sleep easier while fully committed to Plan A. Most couples skip it entirely, jumping straight to attorneys without first agreeing on what they actually want, which is where things tend to go sideways. A postnup, she explains, is available to married couples who want to address what a prenup never covered: a stay-at-home parent's vulnerability, a sudden large inheritance, or financial patterns that have quietly felt unfair for years. Infidelity, she notes, is actually one of the most common triggers, not as a prelude to divorce, but as a bid to stay married on more honest terms. For couples navigating family-mandated agreements, Kaylin introduces the "outlaw", meaning the partner entering a family structure. But there's often more middle ground available than the two options being presented. Never stop talking about what feels fair, because that conversation is the ongoing work of a living relationship. Key Topics: Kaylin's Own Prenup: What They Did Right and Wrong at 21 (04:15)What a Prenup Actually Is and What It Can Cover (11:13)Postnups: Who Gets One and Why (13:23)Stay-at-Home Parents, Inheritances, and When Married Couples Revisit Finances (17:15)Step One: The Ideal Path Before You Call an Attorney (22:07)How to Bring Up a Prenup Without Blowing Up the Relationship (23:25)The "Outlaw": Marrying Into Wealth and Family Requirements (37:47)Never Stop Talking About What Feels Fair (41:23) More About the Guest: Kaylin Dillon is a Certified Financial Planner who specializes in working with couples with separate assets, prenups, or blended families. She wrote the book Prenup Partnership and founded The Prenup Coach to help engaged couples have better money conversations before they say "I do." If she's not talking about money and marriage, she says she entertains herself by following real-time court cases involving spouses. Resources: For Kaylin’s Book and Coursework, visit https://kaylindillonfinancial.com/Kaylin’s Instagram: https://www.instagram.com/theprenupcoach Schedule a Free Consultation: Go to https://www.fyoozfinancial.com and click the button in the upper right-hand corner Join our newsletter to stay up to date on the latest financial resources: https://www.fyoozfinancial.com/signup Natalie Slagle, CFP® and Dan Slagle, CFP® are the founding partners and lead financial planners at Fyooz Financial Planning https://www.fyoozfinancial.com/ — an independent firm dedicated to helping high-earning couples in their 30s and 40s confidently navigate the complexities of managing money together. At Fyooz, they specialize in turning financial stress into strategy, guiding couples through everything from cash flow and investing to aligning money with shared goals. Disclaimer: For updated disclosures, please visit https://www.fyoozfinancial.com/
