Money Penney

About 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.

Publisher

Ryan Penney

Category

business

Language

en

Explicit

Yes

First episode

17 Mar 2026

Latest episode

14 Oct 2026

Latest episodes

36 episodes in the feed.

1. 

   14 Oct 2026

   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

2. 

   8 Oct 2026

   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

3. 

   29 Sept 2026

   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

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Guest appearances

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