Money Penney

Welcome to Money Penney. After realizing the traditional 9-to-5 grind wasn’t the life I wanted, I escaped the rat race at 35 and became work optional so I could live life on my own terms. Now I’m dedicating my time and energy to helping others have the option to do the same. On this show we’ll talk about financial education, investing, money psychology, real estate, and lifestyle design so you can build freedom and live your best life. Because once you buy back your freedom, you’re free to make the world a better place.

Money Penney is a business podcast hosted by Ryan Penney, with 34 episodes on record and a Required Pod Score of 80.

Ryan Penney hosts Money Penney, a business show with 34 episodes published.

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  Episode #32

  Episode 32: How long should you plan on holding Real Estate?

  Sep 23, 202621 min

  One of the biggest mistakes you can make in real estate? Being forced to sell too soon. My general rule is simple: Plan to hold for at least 5 years. Ideally, 10+. Why? Because real estate has friction. When you buy and sell, you can face closing costs, commissions, repairs, financing costs, taxes, and other expenses. A few years of appreciation can disappear quickly when you factor everything in. But as your holding period gets longer, you give more time for the different parts of the investment to potentially work: Appreciation can compound Rents can grow Your mortgage balance gets paid down Equity can build Cash flow can accumulate And most importantly, you give yourself time. Time to ride through a bad market. Time to recover from an expensive repair. Time to wait instead of accepting a bad offer. Trying to perfectly time real estate means getting two decisions right: When to buy AND when to sell. I'd rather buy an asset I believe in, maintain enough reserves to survive the difficult years, and give myself the flexibility to hold. Because in real estate, sometimes the biggest advantage isn't predicting what happens next. It's being able to stay in the game long enough for the investment thesis to play out. Think in decades, not months. #RealEstateInvesting #BuyAndHold #RealEstate #WealthBuilding #FinancialFreedom #LongTermInvesting #CashFlow #FinancialIndependence #MoneyPenney #WorkOptional

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  Episode #31

  Episode 31: The FI path I chose and why

  Sep 17, 202630 min

  I spent years trying to figure out the “best” path to financial independence. Eventually, I realized something: I didn’t need to do everything. I needed to find one thing that fit me and get really good at it. For me, that was real estate. It started with a simple house hack. Then came bigger properties, renovations, mistakes, bad partnerships, years away from investing, and eventually short-term rentals. Over time, I figured out what I actually wanted from an investment: Cash flow Appreciation Leverage Loan paydown Tax advantages Control over creating additional value Short-term rentals checked those boxes—and they also fit my personality. I like hosting. I like creating experiences. I like designing properties. And I like having control over the outcome. But this episode isn't about convincing you that my path should be your path. It's about finding the investment strategy that fits your skills, goals, and lifestyle well enough that you're willing to stick with it for years. Because one of the biggest enemies of compounding is constantly chasing the next opportunity. Stocks. Crypto. Real estate. Businesses. The latest side hustle. You don't have to win at all of them. Pick your lane. Get good at it. Keep improving. Let it compound. That's the path I chose—and it's ultimately what helped me become work optional. ️ Episode 37 of the Money Penney Podcast: My Path to FI #FinancialIndependence #RealEstateInvesting #ShortTermRentals #WorkOptional #FinancialFreedom #MoneyPenney #WealthBuilding #HouseHacking

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  Episode #30

  Episode 30: The Many Paths to FI

  Sep 9, 202632 min

  You don’t need millions of dollars to become work optional. You need enough money, assets, or income to create the level of freedom you actually want. And there isn’t just one path to get there. Invest consistently in index funds House hack and reduce your biggest expense Build cash-flowing real estate Flip properties to generate capital Start a business or side hustle Invest passively when appropriate Move somewhere your money goes further Intentionally reduce your lifestyle expenses The mistake is thinking financial independence has to mean: “I never work another day in my life.” Maybe your version means working three days a week. Maybe it's leaving a high-paying job for something you actually enjoy. Maybe it's spending summers in Europe. Maybe it's simply having enough income outside your W-2 that you're no longer terrified of losing your job. That's why I prefer the term work optional. The goal isn't necessarily to stop working. It's to stop needing to work. Once you know what freedom looks like for you, you can reverse-engineer the income, assets, and lifestyle required to create it. You don't need to follow my exact path. Build the version of freedom that fits your life. ️ In this episode of the Money Penney Podcast , I break down multiple paths to financial independence—and how to start designing yours. What would being work optional look like for you? #FinancialFreedom #WorkOptional #FinancialIndependence #MoneyPenney #RealEstateInvesting #PersonalFinance #WealthBuilding #HouseHacking #FIRE #LifestyleDesign

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  Episode #29

  Episode 29: How it possible to buy one property per year?

  Sep 1, 202613 min

  What if you bought one investment property every year for the next 10 years? It sounds crazy at first. But when you actually break down the strategy, it becomes a lot more realistic. You don't necessarily need to save another 20% down payment from scratch every single year. You can use different strategies along the way: House hack to get started with less money down Buy traditional rentals when you have the capital Flip properties to generate cash for future investments Explore owner financing when the deal makes sense Increase your income and savings rate ♻️ Reinvest cash flow and equity into the next property The first property might be the hardest. But over time, you're potentially building cash flow, equity, experience, relationships, and access to capital. And eventually, the portfolio starts helping fund its own growth. The goal isn't necessarily to own exactly 10 properties. The goal is to create enough income and assets that your W-2 becomes optional instead of necessary. In this episode of the Money Penney Podcast, I break down the roadmap I'd use to try to buy one property every year for the next decade. A crazy goal becomes a lot less crazy when you turn it into a plan. Would you try to buy 10 properties in 10 years? #RealEstateInvesting #FinancialFreedom #RentalProperties #HouseHacking #MoneyPenney #CashFlow #FinancialIndependence #RealEstate #WealthBuilding #WorkOptional

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  Episode #28

  Episode 28: What drives real estate appreciation?

  Aug 26, 202626 min

  What actually makes real estate appreciate? It's not just luck. In Episode 28, Ryan Penney breaks down the forces that drive property values higher—and explains how investors can position themselves to benefit from appreciation instead of simply hoping for it. You'll learn: • Natural appreciation vs. forced appreciation • How renovations can increase property value • Why adding square footage can create significant equity • How location and land scarcity influence prices • Why population and job growth matter • How to identify path-of-progress neighborhoods • The impact of zoning and government regulations • Why local fundamentals matter more than national averages Ryan also shares examples from Denver and Austin to show how dramatically different markets can perform—and why understanding where your control ends is critical. One of the biggest lessons from the episode: Cash flow can create income. Appreciation can create enormous wealth. But the smartest investors understand how to pursue both. If you're trying to grow your net worth through real estate, this episode gives you a framework for understanding where appreciation actually comes from—and how to identify opportunities before everyone else does. ️ Money Penney Podcast — Episode 28 What matters more to you when buying real estate: cash flow or appreciation? #RealEstate #RealEstateInvesting #Appreciation #FinancialFreedom #Investing #MoneyPenney #WealthBuilding #CashFlow #FinancialIndependence

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