Money Penney

Ryan Penney
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  • Investing

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.

  1. 23h ago

    Episode 38: Working Construction to out of the rat race at 35. My story to Financial Independence

    What if you could break free from the rat race and achieve financial freedom before 35? Ryan Penney shares his journey to financial independence, the lessons he learned along the way, and why taking action today can change your financial future. His mission? Help 1,000 people get on the path to financial independence. Your journey starts with a goal. What's yours? 🎧 Watch the full episode on YouTube and Spotify. Follow Ryan on Instagram: @MrMoneyPenny #FinancialFreedom #FinancialIndependence #RealEstateInvesting #WealthBuilding #EscapeTheRatRace

  2. Oct 27

    Episode 37: What is Financial Independence & why is it the most important thing to pursue in life?

    What does financial independence really mean? Is it about retiring early—or having the freedom to choose how you spend your time? In Episode 37 of the Money Penney Podcast, Ryan Penney shares his journey toward financial freedom, how real estate investing shaped his future, and the experiences that changed his perspective on money, work, and success. 🎙️ In this episode: What financial independence really means Why “work optional” matters more than early retirement How real estate investing helped shape Ryan’s journey The Sydney experience that changed his view of success Why meaningful work still matters when money is no longer the main motivation Financial independence isn’t just about not working. It’s about having the freedom to choose. 💬 What would you do if work became optional? Share your thoughts in the comments! #FinancialIndependence #RealEstateInvesting #MoneyPennyPodcast

  3. Oct 23

    Episode 36: I've studied every Investment, and here is the best one

    Stocks, real estate, crypto, bonds, or starting a business—which investment is actually BEST for you? In this episode of the Money Penney Podcast, Ryan Penney breaks down the different ways to build wealth and explains why choosing the right investment isn't just about chasing the highest returns. It's about finding an investment strategy that fits your goals, skills, risk tolerance, and the lifestyle you want to create. After years of investing and working toward financial independence, Ryan ultimately chose short-term and mid-term rentals as his primary wealth-building strategy. But that doesn't mean real estate is the best investment for everyone. In this episode, you'll learn: 📈 Stocks & Index Funds — The benefits of long-term growth, diversification, and relatively hands-off investing. 🏦 Bonds & Cash — How lower-risk investments can support stability, liquidity, and capital preservation. ₿ Cryptocurrency — The potential upside, volatility, and risks associated with digital assets. 🚀 Business Ownership — Why building a business can create wealth but often requires significant time and effort. 🏠 Real Estate Investing — How cash flow, appreciation, leverage, mortgage paydown, and potential tax advantages can work together. Ryan also explores different real estate strategies, including: Buy-and-hold rentalsFix-and-flip investingBRRRR (Buy, Rehab, Rent, Refinance, Repeat)Short-term and mid-term rentalsCommercial real estateSpecialty propertiesHe shares why short-term rentals aligned with his personal strengths, interests, and financial independence goals—and why the same strategy might not be right for someone else. The biggest takeaway? The best investment isn't necessarily the one with the highest potential return. It's the one you understand, can manage through difficult periods, and that helps you build the life you actually want. For Ryan, that meant building enough cash flow through real estate to become work optional at 35. For you, it might look completely different. 💬 If you could only invest in ONE asset class for the next 10 years, what would you choose? Let me know in the comments! Subscribe to the Money Penney Podcast for weekly conversations about investing, financial independence, real estate, and escaping the corporate rat race. Disclaimer: This episode is for educational purposes only and is not financial or investment advice. All investments involve risk, and past performance does not guarantee future results. #MoneyPenney #RealEstateInvesting #FinancialFreedom #Investing #FinancialIndependence

  4. Oct 14

    Episode 35: The Major upside of STRs. How to manage an STR remotely

    What if owning just a few short-term rentals could give you the freedom to design your entire life? In this episode of the Money Penney Podcast, Ryan Penney explains why he chose short-term rentals (STRs) as his path to financial independence—and why the biggest reward isn't necessarily the money. It's the freedom to control your time. Ryan shares his journey from working in corporate America to becoming work optional at 35, including the financial challenges, investing lessons, and experiences that led him to real estate. He explains why short-term rentals became his preferred investment strategy and how a small portfolio of well-positioned properties can potentially generate meaningful cash flow while building long-term wealth. In this episode, you'll learn: 🏠 Why Short-Term Rentals? — What makes STRs different from traditional long-term rentals and multifamily investing. 💰 Cash Flow + Appreciation — How rental income, property appreciation, mortgage paydown, and potential tax advantages can work together. 📈 Quality Over Quantity — Why a few high-performing properties may be more valuable to your lifestyle than managing dozens of average rentals. 🎨 Creating Value Through Experience — How location, design, amenities, and guest satisfaction can influence STR performance. 💻 Managing Properties Remotely — How technology, automation, and reliable teams can help you operate rentals without being physically present. ⏳ The Real Goal: Time Freedom — Why financial independence is about designing a life you enjoy, not just accumulating more money. Ryan also shares what becoming work optional has allowed him to do: ✈️ Travel internationally for months at a time ⛷️ Take spontaneous weekday ski trips 💪 Work out whenever he wants 🥗 Cook healthy meals and prioritize his health ❤️ Spend more time with friends and family 🚀 Work on projects he's genuinely passionate about The biggest takeaway? The goal isn't to own the most properties. The goal is to build enough income-producing assets that you can spend your time doing what matters most to you. Short-term rentals aren't passive, and they come with real challenges, including regulations, maintenance, guest management, and operating costs. But with the right properties, systems, and strategy, they can be a powerful vehicle toward financial independence. Don't build a business that consumes your life. Build one that supports the life you want. 💬 Would you rather own 3 high-performing short-term rentals or 20 traditional long-term rentals? Let me know in the comments! Subscribe to the Money Penney Podcast for more lessons on real estate investing, building wealth, and becoming work optional. This episode is for educational purposes only and is not financial or investment advice. Investment results vary, and cash flow and appreciation are not guaranteed. #ShortTermRentals #AirbnbInvesting #FinancialFreedom #RealEstateInvesting #MoneyPenney

  5. Oct 8

    Episode 34: How much work are STR’s?

    Are short-term rentals really passive income? Or are you just buying yourself another job? In Episode 40 of the Money Penney Podcast, Ryan Penney breaks down the REAL workload behind owning and managing short-term rentals (STRs). From finding and renovating properties to managing guests, coordinating cleaners, handling repairs, and optimizing pricing, there's a lot more work involved than most Airbnb investors realize. But here's the good news: With the right systems, automation, and team, STRs can become significantly less hands-on over time. In this episode, you'll learn: 🏠 The 5 Categories of STR Work — What actually goes into running a successful short-term rental business. ⏰ Startup vs. Ongoing Work — Why acquiring, renovating, furnishing, and launching a property typically require the most effort. 💻 Automation & AI — How tools like PriceLabs, Hospitable, and automated guest messaging can reduce repetitive tasks. 🧹 Building the Right Team — Why dependable cleaners, contractors, and maintenance professionals are essential. 📍 Location Matters — How rural properties, mountain homes, and urban rentals create different management challenges. 📈 Scaling Your Portfolio — How to build systems that allow you to manage multiple properties without doing everything yourself. Ryan also shares lessons from building and operating his own short-term rental portfolio, including mistakes, unexpected challenges, and why the first 12 months can be the hardest. The biggest takeaway? Short-term rentals aren't truly passive. But if you're willing to put in the work upfront, build reliable systems, and delegate effectively, they can become a powerful tool for generating cash flow and working toward financial independence. The goal isn't to create another full-time job. It's to build assets that eventually give you more freedom—not less. 💬 Would you rather self-manage your Airbnb for higher potential profits or hire a property manager to save time? Let me know in the comments! Subscribe to the Money Penney Podcast for more conversations about real estate investing, financial independence, and becoming work optional. #ShortTermRentals #AirbnbInvesting #RealEstateInvesting #PassiveIncome #MoneyPenney

  6. Sep 29

    Episode 33: How much appreciation should I expect?

    How much appreciation should you actually expect when buying a rental property—and how much does choosing the right market matter? In Episode 39 of the Money Penney Podcast, Ryan Penney breaks down the numbers behind real estate appreciation, from long-term U.S. averages to the much stronger growth some individual markets have experienced. Ryan explains why appreciation isn't the same everywhere and explores the factors that can potentially drive property values higher, including job growth, rising wages, population migration, housing demand, and constraints on new supply. In this episode, you'll learn: • Why long-term U.S. home appreciation has historically averaged roughly 3–4% • Why Ryan uses different assumptions when analyzing future deals • How markets like Denver and Austin performed during periods of rapid growth • What to research before investing in a new market • How dramatically different appreciation rates can change the value of a $500,000 property over time • Which large and smaller U.S. markets Ryan is currently watching Ryan also shares lessons from his own investments and discusses markets including Dallas–Fort Worth, Raleigh, Charlotte, Phoenix, Austin, Tampa, Charleston, Myrtle Beach, St. George, Ogden, and Boise. The biggest takeaway? Don't assume every property will appreciate at the same rate. Where you buy—and the economic fundamentals supporting that market—can have a massive impact on your long-term results. What market do you think has the strongest long-term potential? Drop it in the comments. 👇 This episode is for educational purposes only and is not financial or investment advice. Real estate markets vary, and past performance does not guarantee future results. #RealEstateInvesting #RentalProperty #RealEstateAppreciation #FinancialIndependence #MoneyPenney

  7. Sep 24

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

    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

  8. Sep 17

    Episode 31: The FI path I chose and why

    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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About

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.

Information

  • Creator
    Ryan Penney
  • Years Active
    2026
  • Episodes
    39
  • Rating
    Explicit
  • Copyright
    © 2026 Ryan Penney
  • Show Website
    Money Penney