The Bailey Way Podcast

Durelle & Samantha Bailey
  • 5.0 (15)
  • Relationships
  • Updated Weekly

Hosted by Durelle and Samantha Bailey — married for nine years and building life side by side — this show is a real, unfiltered look at what it takes to grow together intentionally. We believe marriage should be aspirational. Structured. Strategic. Not accidental. Each week, we share honest conversations about relationships, financial alignment, business, faith, personal growth, and the systems that have helped us move from instability to ownership — and from survival to vision. This isn’t about pretending to have it all figured out. It’s about choosing alignment, choosing growth, and building on purpose — the Bailey Way.

  1. 1d ago

    How to Fight Fair in Marriage: Communication, Conflict Resolution & Lessons From 10 Years of Being Married

    The marriage you see today isn't the marriage Samantha and Durelle always had.  After nearly 10 years together, this The Bailey Way episode shares some of the hardest seasons of their marriage, from trust issues and anxiety to explosive arguments, communication breakdowns, and moments that tested their commitment. They discuss fights they don't post, the personal healing they had to do, and how relationship coaching helped them learn to fight fair, rebuild trust, and stop treating each other like the enemy. This conversation reveals that a healthy marriage isn't one without conflict, but rather one where both people are willing to grow through it. KEY POINTS:  The reality of navigating difficult seasons after nearly 10 years of marriage. When finally living together exposed unexpected challenges and trust issues. Why unrealistic expectations can make the early stages of marriage harder. Learning that honesty without healthy communication can do more harm than good. How anxiety, past trauma, and unresolved hurt affected their marriage. The Beverly Hills trip that turned into one of their worst arguments. Why walking away was never their solution, even during their toughest seasons. How individual healing and emotional safety transformed their marriage. Learning to fight fair: listening, extending grace, and tackling problems together. How relationship coaching, accountability, and apologies helped rebuild trust. Avoiding resentment, protecting your partner's vulnerabilities, and knowing when to take a break. QUOTES:  “We were definitely honest with each other about how we were feeling in certain seasons and different things like that. And I think that was definitely hard because [those are] the moments where you realize marriage really is a mirror." – Durelle Bailey “A big thing for us was relationship coaching, like calling in somebody to actually help us learn how to fight fair." – Samantha Bailey  "I see it as making a deposit into the bank of resentment when you say things that is going to hurt your person." – Durelle Bailey RESOURCES:  Follow Samantha: IG: @samanthacassandra TikTok: @samanthacassandra_  Follow Durelle: IG: @durellebailey TikTok: @durellebailey The Bailey Way is produced by EPYC Media Network

  2. Oct 14

    Why Couples Should Travel Together: Marriage, Memories & Seeing the World

    From Dubai at 19 to the Swiss Alps, Japan, Singapore, and one unforgettable trip to Bali that went completely wrong, Samantha and Durelle look back on the adventures that shaped their relationship.  In this episode of The Bailey Way, they share their favorite destinations, their very different travel personalities, the hilarious moments that never made the highlight reel, and why they believe some experiences are worth intentionally planning and budgeting for. More than the places themselves, this conversation is about making memories with your person, seeing life beyond your everyday routine, and giving the next generation a bigger world to experience.  KEY POINTS:  Pregnancy update at 21 weeks Why travel has become part of their life together Dubai, nostalgia and traveling there together at 19 Why St. Moritz became one of their favorite trips Samantha relaxes; Durelle goes into survival mode. Why Japan became Durelle’s favorite destination The 12-storey Japan shopping adventure Why they choose to spend money on memories The Bali trip that went completely wrong Budgeting tips and why new experiences strengthen their relationship QUOTES:  “Traveling with your person is just so special. All of these are memories that I will always cherish and value, and there's really nothing like it.” – Durelle Bailey “I had been to 12 countries by the time I was like 15. I learned to ski in Austria, so my parents just always had me around the world, and that's the same thing I want for our daughter.”  – Samantha Bailey  “With the time that we have on this earth, there's no price you can put on memories. And so we don't hesitate to book the trip, book the hotel, and get our butt over in another country and have a good time.” – Durelle Bailey RESOURCES:  Follow Samantha: IG: @samanthacassandra TikTok: @samanthacassandra_  Follow Durelle: IG: @durellebailey TikTok: @durellebailey The Bailey Way is produced by EPYC Media Network

  3. Oct 7

    How to Use a $0 Down VA Loan to Buy a Home and Start Building Wealth

    Samantha and Durelle didn’t start building wealth because they already had money. They started because one taco night introduced them to a military benefit they didn’t even know they had. In this episode, they sit down with Veterans United loan officer Katie Rose to unpack how VA loans work, why $0 down can create an earlier path to homeownership, and how veterans can use the benefit strategically over time. From turning a starter home into rental income to buying a fourplex, refinancing when rates change, and understanding benefits many service members overlook, this conversation is about knowing what you have access to and using it with intention.  If interested in the VA loan with Veterans United: https://www.veteransunited.com/lp/the-bailey-way/?src=dbailey KEY POINTS:  How one overlooked military benefit changed their financial life The taco night that introduced them to VA loans How their first home later brought a $100K profit Why you can use a VA loan more than once How quickly you can find out if you qualify Why renting can feel safer but leave you with nothing Turning a starter home into rental income What higher interest rates mean for VA borrowers VA loan myths, assumable loans, and overlooked benefits How veterans can use a VA loan to buy up to a fourplex How homeownership became part of their wealth-building strategy QUOTES:  “A lot of people have to build some type of wealth to be able to even afford a home. But this is like kind of reverse. It's like: ‘okay, no, we're gonna help you build wealth and build equity.’”  – Samantha Bailey  “You could probably rent that house for double what your mortgage payment is. And then you can purchase a new house and have this producing income on the side.” – Katie Rose “You're essentially building your financial portfolio by doing this because you can use it as a way to supplement other income to your owning something. You get to say when you want to sell it or keep it or rent it or whatever case may be. And the third thing is you get to leave something behind.” – Durelle Bailey RESOURCES:  Follow Samantha: IG: @samanthacassandra TikTok: @samanthacassandra_  Follow Durelle: IG: @durellebailey TikTok: @durellebailey The Bailey Way is produced by EPYC Media Network

  4. Sep 23

    How We Built Our Life Together: Money, Career Pivots & Walking Away From the “Safe” Path

    The life we built required us to stop treating “safe” like the ultimate goal. In this Best of The Bailey Way episode, we revisit the money decisions, career pivots, sacrifices, and leaps of faith that changed our future, from combining finances to walking away from medicine and retiring Samantha at 31. Ultimately, building a life together sometimes means trusting God, trusting each other, and having the courage to leave the path that looks safest on paper. KEY POINTS:  3: Why Marriage Is the Biggest Business Decision You’ll Ever Make 10: Should Married Couples Combine Finances? Money, Boundaries and Building a Life Together 4: Is Cohabitation Replacing Marriage? Why Fewer People Are Getting Married 11: Making Scary Pivots: Why I Walked Away From Medicine to Become an Entrepreneur 1: I Retired My Wife at 31: How We Left Corporate & Military Life RESOURCES:  Follow Samantha: IG: @samanthacassandra TikTok: @samanthacassandra_  Follow Durelle: IG: @durellebailey TikTok: @durellebailey The Bailey Way is produced by EPYC Media Network

  5. Sep 16

    What 9 Years of Marriage Taught Us About Love, Partnership & Choosing Each Other

    Nine years of marriage have taught us that love is only the beginning. The real work is learning how to keep choosing each other through change, conflict, distance, money, expectations, and growth. In this Best of The Bailey Way episode, we revisit the lessons that shaped our marriage, from choosing the right partner and surviving long-distance to building a healthy partnership without expecting your spouse to complete you. Lasting love is not about perfection. It is about intention, growth, and choosing each other again and again. KEY POINTS:  3: Why Marriage Is the Biggest Business Decision You’ll Ever Make 9: How We Survived Long Distance & Built a Life Together | How We Met Part 2 7: Is Your Spouse Supposed to Make You Happy? Lessons After 9 Years of Marriage 10: Should Married Couples Combine Finances? Money, Boundaries and Building a Life Together 7: Is Your Spouse Supposed to Make You Happy? Lessons After 9 Years of Marriage RESOURCES:  Follow Samantha: IG: @samanthacassandra TikTok: @samanthacassandra_  Follow Durelle: IG: @durellebailey TikTok: @durellebailey The Bailey Way is produced by EPYC Media Network

  6. Sep 9

    Don’t Let Your Past Dictate Your Future: Healing Childhood Trauma & Breaking Generational Cycles

    What happens when everything you grew up around tells you what your life is supposed to look like, but you decide to build something different? In this episode of The Bailey Way, Durelle opens up about growing up without stability, moving 12 times by age 12, living in motels, navigating a difficult relationship with his mother, and having no blueprint for the marriage, family, education, or success he wanted for himself. He shares the people who gave him his first glimpse of stability, why Samantha’s family made the life he imagined feel tangible, and the mindset that helped him stop seeing his circumstances as a reason he couldn’t move forward. Samantha and Durelle also unpack the cost of breaking generational patterns, including outgrowing relationships, learning healthier communication in marriage, healing without waiting for an apology, and making sure the pain you experienced doesn’t become pain your children inherit. This is a conversation about faith with action, doing it afraid, and making the decision to build what you may have never been given.  KEY POINTS:  Growing up without stability or a blueprint for success The woman who showed Durelle what consistency looked like Seeing Samantha’s family and realizing, “This is what I want” Why your circumstances don’t have to become your excuses Becoming the person who changes your family’s lineage “Don’t let what happened to you happen through you” Why growth sometimes costs you relationships Unlearning unhealthy communication in marriage Doing it afraid, hurt, scared, and without all the answers Why faith still requires you to do the work QUOTES:  “God will replace whatever relationships you thought you needed with people that are so much healthier, so much better, so much more like you. But you have to be willing to let go of some people.” – Samantha Bailey  “I want every child that comes after me—that’s a Bailey after me—to hear about Grandpa’s story, but never have to experience it for themselves.” – Durelle Bailey  “Somewhere in every bloodline of like the successful people that you see on Martha's Vineyard, someone in that bloodline decided that they weren't going to make excuses.” – Samantha Bailey  “You owe it to yourself to do it afraid – to do it scared, to do it without all the answers; to do it with the anxiety, with the fear, with the hurt, with the pain.”  – Durelle Bailey  RESOURCES:  Follow Samantha: IG: @samanthacassandra TikTok: @samanthacassandra_  Follow Durelle: IG: @durellebailey TikTok: @durellebailey The Bailey Way is produced by EPYC Media Network

  7. Sep 2

    Making Scary Pivots: Why I Walked Away From Medicine to Become an Entrepreneur

    What happens when the life you worked years to build is no longer the life you believe you’re supposed to live? In this episode of The Bailey Way, Samantha and Durelle unpack one of the biggest pivots of their marriage: walking away from Durelle’s path to becoming a doctor and betting on the unexpected opportunity God was placing in front of them. They share the years of sacrifice it took to get Durelle into a highly competitive military medical program, the strain that season placed on their marriage, and why letting go of that dream initially felt like everything they had endured had been for nothing. But while medical school remained the safe and predictable plan, their content and businesses were quietly becoming something neither of them could ignore. From their first $13,000 brand deal to making six figures from digital products in two months, Samantha and Durelle explain why they didn’t simply “take a leap of faith.” They built proof of concept, prepared financially, paid attention to the opportunities in front of them, and ultimately trusted God enough to change the plan. This is a conversation about knowing when persistence becomes rigidity, why preparation gives you the freedom to take risks, and how sometimes the path you thought was the destination was actually preparing you for what came next. KEY POINTS:  The dream of becoming a doctor and what it took to get there How medical school strained their marriage The unexpected opportunity that changed their plans Why walking away felt like wasting years of sacrifice Knowing when it’s time to pivot Why preparation matters before taking a leap How past experiences prepare you for what’s next Choosing faith over the safety of the original plan How the pivot gave them more time, freedom, and family QUOTES:  “I was so married to this plan, like, oh my god, I have sacrificed so much. Like we, our relationship had been through it. Like the only thing that was gonna make that feel worth it to me was you becoming a doctor.” – Samantha Bailey  “Desire shouldn't give you permission to pivot into something. It really should be [a] desire mixed with skill and opportunity that gives you the permission to pivot into something.” – Durelle Bailey  “God has more for you, and when He gives you that opportunity, I think it takes a level of faith to actually make that leap and make that pivot.” – Samantha Bailey  “Failure is not failure; it's actually data… It gives you the opportunity to analyze what you did and what you can do better to try again.” – Durelle Bailey  “It is okay to change your mind.  As long as you have a foundation and you're not leaping into something completely new, but you've laid a foundation. It is okay to change your mind.” – Samantha Bailey  RESOURCES:  Follow Samantha: IG: @samanthacassandra TikTok: @samanthacassandra_  Follow Durelle: IG: @durellebailey TikTok: @durellebailey The Bailey Way is produced by EPYC Media Network

  8. Aug 26

    Should Married Couples Combine Finances? Money, Boundaries and Building a Life Together

    Should married couples combine their finances, or is it healthier to keep some things separate? In this episode of The Bailey Way, Samantha and Durelle get real about the system they use to manage money in their marriage, why they believe financial transparency builds trust, and how they balance joint finances with individual freedom. They also unpack prenups, financial habits, getting married before you “have it all,” and why the goal of marriage isn’t independence or codependence, but healthy interdependence. From building together when they were both making less than $50K to creating a life where every financial decision is about moving the family forward, the Baileys share why money should never become more valuable than the marriage itself. KEY POINTS:  Why financial transparency builds trust in marriage The Bailey system for combining finances while keeping “fun money” When a prenup may make sense Why alignment matters more than one “right” way to manage money Financial habits matter more than how much someone earns Why you don’t need to “have it all” before marriage Independence vs. codependence vs. healthy interdependence How weekly planning keeps their marriage and money aligned Why money should remain a tool, not become the goal Using wealth to create peace, generosity, and a fulfilling family life QUOTES:  “You put so much emphasis on how much the man makes, not enough on what his financial habits are.” – Samantha Bailey  “If you're sharing a life, you're sharing bodies, you're sharing a home, you're sharing a bed. Why aren't you sharing your resources? Because money is a resource.” – Durelle Bailey  “It's not about the money itself. It's how do you use the money as a tool to create a life that feels fulfilling.”  – Samantha Bailey  “We need to start putting emphasis more on peace, contentment, happiness, and potential, rather than the full package.” – Durelle Bailey RESOURCES:  Follow Samantha: IG: @samanthacassandra TikTok: @samanthacassandra_  Follow Durelle: IG: @durellebailey TikTok: @durellebailey The Bailey Way is produced by EPYC Media Network

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Ratings & Reviews

5
out of 5
15 Ratings

About

Hosted by Durelle and Samantha Bailey — married for nine years and building life side by side — this show is a real, unfiltered look at what it takes to grow together intentionally. We believe marriage should be aspirational. Structured. Strategic. Not accidental. Each week, we share honest conversations about relationships, financial alignment, business, faith, personal growth, and the systems that have helped us move from instability to ownership — and from survival to vision. This isn’t about pretending to have it all figured out. It’s about choosing alignment, choosing growth, and building on purpose — the Bailey Way.

Information

  • Creator
    Durelle & Samantha Bailey
  • Years Active
    2026
  • Episodes
    18
  • Rating
    Clean
  • Copyright
    © All rights reserved.

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