MILMO Show

Money decisions can feel a lot heavier in military life. Between deployments, PCS moves, and the uncertainty that often comes with service, it's easy for stress, fear, and past experiences to shape how you spend, save, or avoid money altogether. In this episode, Tyler West and I discuss why money feels so emotional and how financial therapy can help. We get into how past experiences influence money habits, how stress can show up in financial decisions, and ways military families can start having healthier conversations about money. Tyler is an Army veteran, financial planner, and financial therapist who works with military and veteran families. Tyler brings both professional expertise and lived military experience to this conversation, helping break down the emotional side of money in a practical, relatable way.

There's a VA benefit available to eligible SGLI and VGLI survivors that almost no one seems to know about. It's the Beneficiary Financial Counseling Service. It gives free financial planning during one of the hardest times a military family can face, yet too many people miss it entirely. In this episode, Certified Financial Planner Brian O'Neill and I, are talking about what this benefit is, who it's for, where the process is breaking down, and why better awareness could help protect survivors from costly mistakes and predatory financial products. Brian is a retired Air Force Colonel, former F-16 and F-35 pilot, and founder of Winged Wealth Management and Financial Planning. He has worked directly with this program for years, helping survivors navigate major financial decisions. Today, he's sharing what families need to know and how we can help spread the word. For more information, visit the full show notes at https://milmo.co/podcast/beneficiary-financial-counseling-service For more MILMO, follow at: MILMO.co ItsMILMO on YouTube @itsmilmo on X @itsmilmo Instagram @itsmilmo LinkedIn @itsmilmo Facebook

You can know exactly what you should be doing with your money and still not do it. Maybe you know you need to save more, pay down debt, or finally sit down and plan for retirement. But somehow, life, stress, and emotions get in the way. Sometimes the story you're telling yourself gets in the way. In this episode, military spouse, Ashley Quamme and I discuss the real reason there's often a gap between knowing and doing when it comes to money. We also talk about the psychology behind financial avoidance, how uncertainty can shape your money behavior, and practical ways to start changing habits that keep you stuck. Ashley is a Licensed Marriage and Family Therapist, Certified Financial Therapist™, and a Financial Behavior Specialist®. She's the Chief Behavioral Officer for advisory firms and host of the Planning & Beyond® podcast. She helps bridge the gap between financial knowledge and the human side of behavior change. For more MILMO, follow at: MILMO.co ItsMILMO on YouTube @itsmilmo on X @itsmilmo Instagram @itsmilmo LinkedIn @itsmilmo Facebook For more information, visit the full show notes at https://milmo.co/podcast/why-you-know-what-to-do-with-money

Money decisions are getting harder, not easier. There's more information, more tools, and now, more artificial intelligence telling you what you should do. It can feel like you finally have answers at your fingertips, but that doesn't always mean those answers are right. In this episode, I'm talking about AI and your money, where it can actually help, where it can get you into trouble, and how to use it without letting it make decisions for you. https://milmo.co/podcast/ai-financial-advice For more MILMO, follow at: MILMO.co ItsMILMO on YouTube @itsmilmo on X @itsmilmo Instagram @itsmilmo LinkedIn @itsmilmo Facebook

Many in the military community see a problem and feel called to fix it. Maybe it's childcare, employment, or support services. One of the first questions that comes up is: Should this be a nonprofit or a business? The reality is that the decision isn't always clear, and choosing the wrong path can cost you time, money, and momentum. In this episode, Kayla Corbitt and I discuss how to decide between a nonprofit and a for-profit business, and what it really takes to run a nonprofit. We also talk about the realities of funding and impact, so you can make the right choice before you get started. Kayla is the Founder and CEO of Operation Child Care Project, a national nonprofit delivering data-informed solutions for military families navigating childcare and support services. She's also a military spouse who has built both a nonprofit and a business, giving her a unique perspective on what it actually takes to create meaningful change. Through her work, Kayla has helped turn real family challenges into practical, community-based solutions, earning national recognition, including Military Spouse of the Year and a spot on the Mighty 25 list of changemakers. https://milmo.co/podcast/nonprofit-vs-for-profit-what-to-know For more MILMO, follow at: MILMO.co ItsMILMO on YouTube @itsmilmo on X @itsmilmo Instagram @itsmilmo LinkedIn @itsmilmo Facebook

Starting a business can feel empowering, especially if you're looking for control over your earning ability. But a lot of entrepreneurs figure out that instead of building a business that gives them freedom, they've built an extremely demanding job that depends entirely on them. In this episode, Diana Jaquith shares how entrepreneurs can build a business that has real value beyond the owner. We talk about the financial signals that show whether a business is healthy, and why systems and delegation matter more than most founders realize. We also discuss exit planning and why thinking about the end of your business early can help you build something stronger today. Diana is a CEO, CFO, angel investor, and Certified Exit Planning Advisor (CEPA). She is the CEO of WISE Advise + Assist Team, a virtual growth agency she founded to empower military spouses and veterans, and a managing partner at Cor Leo Advisors, an exit planning firm. Diana has spent more than fifteen years helping entrepreneurs grow, scale, and prepare their businesses for long-term value. https://milmo.co/podcast/build-a-scalable-business For more MILMO, follow at: MILMO.co ItsMILMO on YouTube @itsmilmo on X @itsmilmo Instagram @itsmilmo LinkedIn @itsmilmo Facebook

A lot of people are curious about investing in individual stocks but were never taught how to do it, and want to learn. But trying to figure out where, how, and when to buy and sell stocks can feel overwhelming. There are charts, numbers, and unfamiliar terms everywhere. Even basic questions like where to open an account, how to fund it, or how to place a trade can feel confusing. In this episode, we are going to talk about what paper trading is, who it is helpful for, how it can build your confidence in the stock market, and how you can use it to explore individual stock investing while keeping the foundation of your retirement plan exactly where it should be. https://milmo.co/podcast/paper-trading For more MILMO, follow at: MILMO.co ItsMILMO on YouTube @itsmilmo on X @itsmilmo Instagram @itsmilmo LinkedIn @itsmilmo Facebook

Running a business can feel like emotional whiplash. One minute you're celebrating a win, and the next you're questioning everything. Add in a military transition, a new identity, or the pressure to succeed, and it's easy to tie your worth to outcomes you can't control. In this episode, I talk with Ken Davenport about how Stoicism gives military entrepreneurs and service members a framework for navigating uncertainty, rejection, and identity shifts. Ken is a San Diego–based entrepreneur, author, and co-founder of Mission Edge, where he supports nonprofits, social entrepreneurs, and underserved founders. Drawing on decades as a CEO and startup founder, he teaches how ancient virtues can help modern leaders manage emotions, handle rejection, and build resilient, mission-driven work. For more MILMO, follow at: MILMO.co ItsMILMO on YouTube @itsmilmo on X @itsmilmo Instagram @itsmilmo LinkedIn @itsmilmo Facebook For more information, visit the full show notes at https://milmo.co/podcast/stoicism-for-military-entrepreneurs

I've had a hypothesis sitting in the back of my mind for a while. Buy Now, Pay Later has become normal. Sports betting is legal in more states than ever. OnlyFans subscriptions are private, easy, and a click away. None of these things automatically ruins your finances. But I keep wondering what happens when they start stacking. In this episode, Josh Bannerman, Marine veteran and Certified Financial Planner, and I pressure-test my hypothesis: are Buy Now, Pay Later, gambling, and subscription spending creating a perfect storm for military finances? Josh breaks down the difference between investing and binary bets, how leverage and small payments eat into your paycheck, what "fun money" should really look like, and how to build discipline without losing your ability to enjoy life. Josh is a fee-based financial planner and co-founder of the Stacking Benjamins podcast. With over 25 years of experience in financial planning and entrepreneurship, he helps clients create clear plans that balance long-term wealth with real life. https://milmo.co/podcast/financial-perfect-storm-gambling-military For more MILMO, follow at: MILMO.co ItsMILMO on YouTube @itsmilmo on X @itsmilmo Instagram @itsmilmo LinkedIn @itsmilmo Facebook

Estate planning is one of those things most people know they should do, but it often feels overwhelming, expensive, or easy to put off. Between our busy lives and discomfort around death, even responsible adults delay it far longer than they want to admit. In this episode, we break estate planning down into what it really is, a practical way to reduce stress for the people you love and make sure your wishes are clear. We talk about when estate planning actually starts, the small steps that matter most, and how to get started without feeling overwhelmed. My guest is Sasha Grabenstetter, an Accredited Financial Counselor® and financial educator whose work focuses on the intersection of money, behavior, and lived experience. For more MILMO, follow at: MILMO.co ItsMILMO on YouTube @itsmilmo on X @itsmilmo Instagram @itsmilmo LinkedIn @itsmilmo Facebook

Student loans can feel overwhelming. Repayment plans change, headlines create confusion, and it's hard to know what actually applies to your situation or what to do next. In this episode, student loan expert Robert Farrington breaks down what's really happening with student loans right now, what borrowers need to pay attention to, and how to take strategic action instead of staying stuck. We also talk about his journey building a successful media business from the ground up, what he'd repeat, what he'd change, and what he believes matters most if you want to build something that lasts. Robert is a student loan expert and the founder of The College Investor, a leading news organization focused on the intersection of personal finance and education. https://milmo.co/podcast/state-of-student-loans For more MILMO, follow at: MILMO.co ItsMILMO @itsmilmo @itsmilmo @itsmilmo @itsmilmo

Being busy can feel responsible and productive, but if you've ever found yourself working all the time and still wondering why the money doesn't reflect the effort you're putting in, you are in good company. In this episode, I'm talking about why busy is not a revenue strategy, how easy it is to get pulled into work that feels productive but doesn't actually bring in income, and how to think about the different hats you wear in business, especially when you're building something new, and nothing feels certain yet. https://milmo.co/podcast/busy-is-not-a-revenue-strategy For more MILMO, follow at: MILMO.co ItsMILMO on YouTube @itsmilmo on X @itsmilmo Instagram @itsmilmo LinkedIn @itsmilmo Facebook

So many people in the military community carry hard-earned knowledge from their careers, side hustles, and lived experiences, but aren't always sure how to turn it into consistent income aligned with their lives. Here is the encore airing of Transforming Your Knowledge into Profitable Memberships with Stu McLaren, a standout episode that reminds us your expertise has value, and that building something meaningful doesn't have to mean burning yourself out. It's a motivating listen as you reflect on what you know, what you've learned, and what might be possible next.

Feeling behind can sneak up on you. It's not always about the numbers. It's that constant sense that you should be further along, more caught up, more on top of things than you are. And for military families, that feeling can hit even harder when life keeps moving, whether you're ready or not. In this episode, I'm sharing a quick financial reset. Not a full overhaul or a long to-do list. Just a steady way to pause, get your footing, and decide what actually deserves your attention right now. https://milmo.co/podcast/financial-reset

Saving money is something most people want to do or are already doing, but where that money sits often gets overlooked. A lot of service members and spouses are doing the right thing by spending less than they make and saving money, but your savings might not be working to its fullest potential for you. And that can slow your progress, even when you're trying hard. In this episode, I'm talking about high-yield savings accounts, what they are, how to choose the right one for your life, and how to maintain it. I'm going to share some strategies you can use and stick with, especially during military life. https://milmo.co/podcast/high-yield-savings-account For more MILMO, follow at: MILMO.co ItsMILMO on YouTube @itsmilmo on X @itsmilmo Instagram @itsmilmo LinkedIn @itsmilmo Facebook

The start of a new year brings a lot of pressure. Pressure to fix everything, do more, be better, and somehow come up with a brand-new version of yourself at the stroke of midnight. And for many military families and others who feel financially or personally behind, that pressure can feel overwhelming instead of motivating. In this episode, I want to share a more straightforward approach to goals, one that I personally use, especially as I head into 2026. It's not about doing more. It's about creating space, trusting your gut, and taking steady action on the things that will actually bring you peace and joy. https://milmo.co/podcast/choosing-peace-over-pressure-new-year For more MILMO, follow at: MILMO.co ItsMILMO on YouTube @itsmilmo on X @itsmilmo Instagram @itsmilmo LinkedIn @itsmilmo Facebook

As we close out the year and look ahead to what's possible, this felt like the right moment to revisit a meaningful conversation on the show. Building wealth in the military isn't about quick wins. It's about clarity, confidence, and playing the long game, even when life gets unpredictable. Here is the encore airing of Building Wealth for Military Families with Jerry Quinn, one of my top episodes of 2025 and a powerful reminder that consistent, values-driven decisions can shape a strong financial future. A fitting note of inspiration as we head into 2026. https://milmo.co/podcast/building-wealth-for-military-families For more MILMO, follow at: MILMO.co ItsMILMO on YouTube @itsmilmo on X @itsmilmo Instagram @itsmilmo LinkedIn @itsmilmo Facebook

Most of us spend years chasing success without ever stopping to ask what "living well" really means. We talk about building wealth or hitting financial milestones, but often overlook the two resources that matter most: our time and our health. In this episode, Navy pilot Zach Rodriguez shares about how a near-fatal helicopter mishap pushed him to rethink everything from what success looks like to how we care for our bodies and our finances. Zach shares the journey that led him from aviation to helping people align their money with their well-being. https://milmo.co/podcast/purposeful-financial-planning For more MILMO, follow at: MILMO.co ItsMILMO on YouTube @itsmilmo on X @itsmilmo Instagram @itsmilmo LinkedIn @itsmilmo Facebook

For many veterans, the hardest part of leaving the military isn't the transition, it's figuring out what to do with the physical and mental wear-and-tear of service. Too many walk away without documenting injuries, without understanding the claims process, or believing they don't "deserve" benefits because someone else had it worse. But overlooking a VA disability claim can affect your health, your income, and the opportunities you. In this episode, Jex Roach, a Marine Corps veteran, Army spouse, financial counselor, and founder of FinanciFI Coaching shares practical guidance to help veterans move from uncertainty to financial and personal stability. We talk about how VA disability really works, why the process is more legal than medical, and what to do when you receive back pay or have delays that create financial stress. Show notes can be found here: https://milmo.co/podcast/va-disability-claim For more MILMO, follow at: MILMO.co ItsMILMO on YouTube @itsmilmo on X @itsmilmo Instagram @itsmilmo LinkedIn @itsmilmo Facebook

The financial risks facing service members today look nothing like they did 10 or 15 years ago. There used to be real barriers. A literal base gate stood between you and companies that didn't have your best interests at heart. Commanders could keep bad actors out. The Department of War could set policies and say "nope, not on installations." But that world is gone. Today, the enemy isn't standing at the gate trying to get in. The enemy is already in your pocket. It's in your phone, your apps, and the ads. It's also the algorithms, the late-night scrolling, and the "veteran-recommended" investment opportunities that sound legit but are, in most cases, not. In this episode, I'm talking about why service members and military spouses must take ownership of their financial safety in a world where financial predators don't need physical base access anymore, and how you can build your own gate since the old one doesn't exist. https://milmo.co/podcast/protect-your-money For more MILMO, follow at: MILMO.co ItsMILMO on YouTube @itsmilmo on X @itsmilmo Instagram @itsmilmo LinkedIn @itsmilmo Facebook