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

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 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

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.

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

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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.

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

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