MILMO Show

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 on YouTube @itsmilmo on X @itsmilmo Instagram @itsmilmo LinkedIn @itsmilmo Facebook  

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. For more MILMO, follow at: MILMO.co ItsMILMO on YouTube @itsmilmo on X @itsmilmo Instagram @itsmilmo LinkedIn @itsmilmo Facebook

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 For more MILMO, follow at: MILMO.co ItsMILMO on YouTube @itsmilmo on X @itsmilmo Instagram @itsmilmo LinkedIn @itsmilmo Facebook

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

Most people think about taxes one stressful season at a time, but that mindset can cost you opportunities. Especially if you're in the military, planning for early retirement, or navigating years when your income swings up and down. When you don't understand how the rules work across your whole financial life, it's easy to miss out on the strategies designed to help you keep more of what you earn. In this episode, tax expert and financial planner Sean Mullaney breaks down the difference between annual tax prep and true lifetime tax planning. We talk about how early retirement opens unexpected tax advantages, why "the compelling three" savings tactics matter, where Roth conversions actually make sense, and when they don't. Also, how military-specific situations like pensions and combat-zone income change the equation. https://milmo.co/podcast/lifetime-tax-planning For more MILMO, follow at: MILMO.co ItsMILMO on YouTube @itsmilmo on X @itsmilmo Instagram @itsmilmo LinkedIn @itsmilmo Facebook

Too many service members begin their careers already on their heels, navigating debt and financial confusion. And for many, lack of early financial readiness awareness doesn't just stress their wallets, it limits their options. In this episode, retired Army Colonel Michael Tremblay shares what he witnessed across the full spectrum of service, from onboarding new recruits to transitioning soldiers after decades in uniform, and why financial freedom is one of the most powerful readiness tools a service member can have. https://milmo.co/podcast/financialreadiness-from-day-one   For more MILMO, follow at: MILMO.co ItsMILMO on YouTube @itsmilmo on X @itsmilmo Instagram @itsmilmo LinkedIn @itsmilmo Facebook

The holidays can be a special time full of connection with coworkers, friends, and family, but they can also be a season when money feels out of control. Between travel, gifts, parties, food, and "just one more present" moments, it's easy for two months of spending to undo months of progress. For many military families, the pressure hits even harder with long travel distances, family expectations, and the feeling that memories have to come at a price tag. In this episode, I'm breaking down how to prepare for the holiday season in a way that keeps your financial goals front and center, so you can enjoy all the celebrations going into debt or starting the New Year stressed out and behind. https://milmo.co/podcast/holiday-spending-tips For more MILMO, follow at: MILMO.co ItsMILMO on YouTube @itsmilmo on X @itsmilmo Instagram @itsmilmo LinkedIn @itsmilmo Facebook

Veterans are built different. We've learned to push when others quit, to focus on the big picture instead of getting caught up in small stuff, and to adapt when things change. We've mastered discipline, resilience, and teamwork —the same qualities that drive financial success.  In this episode, I'm breaking down why veterans have what it takes to rule the world—financially speaking. Because when you combine our strengths with the resources and benefits available to us, the path to financial freedom becomes shorter, smarter, and stronger. Veterans already know how to make short-term sacrifices for the greater good, and that gives them a huge advantage in building wealth. https://milmo.co/podcast/veterans-should-rule-the-world For more MILMO, follow at: MILMO.co ItsMILMO on YouTube @itsmilmo on X @itsmilmo Instagram @itsmilmo LinkedIn @itsmilmo Facebook

In this episode, we revisit the timeless lessons from The Millionaire Next Door, how ordinary habits create extraordinary wealth, and explore the difference between managing money day to day and truly planning for the long term. Kirk also shares practical guidance on paying off debt, saving for the future, and building flexibility into your financial life, especially for military families facing uncertainty. Kirk Kinder, Director of Financial Planning at Bastion Fiduciary, a fee-only financial planning firm built on the military ethos. Kirk's path to finance started in the U.S. Coast Guard, took a detour through The Motley Fool, and eventually led him to help others chart their financial course. https://milmo.co/podcast/learn-from-the-millionaire-next-door For more MILMO, follow at: MILMO.co ItsMILMO on YouTube @itsmilmo on X @itsmilmo Instagram @itsmilmo LinkedIn @itsmilmo Facebook

Right now, there's a lot of anxiety, confusion, and information floating around. The U.S. government has been shut down since October 1st, and we're now in the last week of the month. It's one of the longest shutdowns in modern U.S. history. If you've been feeling uneasy or just plain tired of the uncertainty, you're not alone. It's totally normal to feel that way. But there's also good news and today, I want to help you focus on that. In this episode, I'm breaking down what's really going on with the government shutdown, what it is, why it's happening, and how it's impacting military pay and benefits. We'll talk about what's open and what's not, what you can do if pay is delayed on November 1st, and where you can find real help right now. And because this show is all about uplifting others, not panic, I'm also sharing steps you can take to stay on track financially, protect your credit, and support one another. https://milmo.co/podcast/government-shutdown-military-pay-benefits-2025

Life is so precious, and I'm squeezing my family a lot tighter this week. Last week, I lost my grandmother. I'm recording this on the morning of her funeral, as I get ready to celebrate her life and say goodbye. I feel incredibly blessed that she lived to be over 98 years old and that I was able to spend so much time with her. And even more thankful that I was able to sit down and record this conversation with my Grandmother. Having her voice, her stories, and her laughter captured in this episode is something I'll cherish. When I meet listeners in person, this episode is something people frequently mention. It's a special episode for me, and I wanted to share it again, both for those who've never heard it and for those who loved it the first time. Here's the encore airing of My Grandma's Story, originally released on March 22, 2021.