3 Real Estate Investing Lessons I Wish I Knew

Matt Bowles | Maverick Investor Group
  • 5.0 (10)
  • Investing
  • Updated Biweekly

Experienced real estate investors reflect on their journeys and share the 3 most important lessons they wish they knew when getting started. Hosted by Matt Bowles of Maverick Investor Group, this show draws out practical lessons about turnkey rental properties, financial freedom, portfolio growth, tax strategy, and building long-term wealth through real estate. Each episode breaks down the specific strategies, mistakes, mindset shifts, and investing principles that helped guests scale their portfolios and create more freedom in their lives. Topics include long-term rental properties, short-term rentals, medium-term rentals, passive income, self-directed IRAs, bonus depreciation, financing, leverage, market selection, asset protection, and remote real estate investing. Guests also share candid stories about overcoming fear, analyzing deals, managing risk, and using real estate investing to create more flexibility, location independence, and lifestyle freedom. Whether you are buying your first rental property or growing a large portfolio, this podcast is designed to help you learn faster, avoid costly mistakes, and make smarter investing decisions.

Episodes

  1. 4d ago

    How Sarah Weaver Used Medium-Term Rentals to Fund a Life of World Travel (Ep 6)

    Hear how Sarah scaled medium-term rentals remotely, built passive income, and designed a life of full-time travel. 👉 Want to build a cash-flowing rental property portfolio from anywhere? Watch my Free Training on How To Buy Turnkey Rental Properties in the most investor-advantaged U.S. real estate markets Sarah Weaver shares how she built a 20-unit rental portfolio across four states while traveling full-time to 56 countries on all seven continents. Sarah breaks down how she transitioned from traditional long-term rentals into medium-term rentals, why furnished rentals became a powerful cash flow strategy, and how she learned to invest remotely without being tied to a single location. She also explains the systems she uses to self-manage properties from abroad, the importance of deal analysis and investor networking, and how she overcame fear and analysis paralysis while scaling her portfolio. Along the way, Sarah shares insights on digital nomad life, location-independent entrepreneurship, remote real estate investing, and how she designed a lifestyle built around freedom, travel, and intentional living through cash-flowing rental properties. → Full show notes with direct links to everything discussed are available here.

  2. Jul 14

    How Scott Saunders Built an 82-Property Portfolio Through Turnkey Real Estate Investing (Ep 5)

    Learn how turnkey rentals, strategic tax planning, and investor networking can accelerate real estate portfolio growth. 👉 Want to build a cash-flowing rental property portfolio from anywhere? Watch my Free Training on How To Buy Turnkey Rental Properties in the most investor-advantaged U.S. real estate markets Scott Saunders shares how he built an 82-property portfolio through turnkey real estate investing, strategic tax planning, and long-term wealth building systems designed to create financial freedom. Drawing on more than 37 years in the 1031 exchange industry and over 100,000 transactions, Scott explains why he prefers single-family rental homes over large apartment complexes, how investors can scale portfolios through repeatable systems and market diversification, and why positive cash flow matters for staying in the game long term. He also breaks down the importance of surrounding yourself with a community of like-minded real estate investors, leveraging the tax code to accelerate portfolio growth, and using a “vault” strategy to store capital and create additional liquidity for future investments. → Full show notes with direct links to everything discussed are available here.

  3. Jun 30

    How Dr. Rachel Gainsbrugh Retired at 41 with Short-Term Rental Properties (Ep 4)

    Hear how Rachel escaped burnout, paid down debt, and replaced her pharmacist salary with short-term rental income. 👉 Want to build a cash-flowing rental property portfolio from anywhere? Watch my Free Training on How To Buy Turnkey Rental Properties in the most investor-advantaged U.S. real estate markets Dr. Rachel Gainsbrugh shares how she transitioned from working exhausting pharmacy shifts with massive student loan debt to achieving financial freedom through short-term rental properties and cash flow. A first-generation Haitian American raised in Miami, Rachel explains how she and her husband used strategic real estate investing to replace their earned income, pay down debt, and retire early through a portfolio of high-performing short-term rentals. She breaks down the lessons she learned scaling from her first property into an 18-door portfolio generating significant monthly cash flow.  She explains how she leveraged AI-powered pricing tools, corporate housing demand, and insurance-funded temporary housing to maximize rental income. Rachel also discusses the mindset shifts that helped her stop “playing small,” why she believes investors should start before they feel ready, and how tax strategy, passive income, and focused execution can accelerate wealth building for busy professionals. In addition, she shares insights from coaching healthcare professionals through her program at Short Term Gems. → Full show notes with direct links to everything discussed are available here.

    How Dr. Rachel Gainsbrugh Retired at 41 with Short-Term Rental Properties (Ep 4)

  4. Jun 16

    How Ryan Lee Built a 10-Year Retirement Plan with Rental Properties (Ep 3)

    Hear how Robert Allen inspired Ryan Lee to use rental properties and passive income to build wealth outside Wall Street. 👉 Want to build a cash-flowing rental property portfolio from anywhere? Watch my Free Training on How To Buy Turnkey Rental Properties in the most investor-advantaged U.S. real estate markets Ryan Lee shares how losing much of his retirement savings during the 2008 financial crisis pushed him to rethink traditional retirement planning and build wealth through rental properties, passive income, and real estate investing. Inspired by Robert Kiyosaki’s Rich Dad Poor Dad and Robert Allen’s “retire in 10 years” framework, Ryan explains how he transitioned from the corporate world into building a real estate portfolio designed to generate financial freedom through cash flow rather than dependence on Wall Street. He shares the lessons he learned scaling from his first single-family rentals into a long-term passive income strategy, why he believes financial freedom must be measured in time rather than just net worth, and how systems, leverage, and investor mindset helped him accelerate his results. Ryan also breaks down his approach to using life insurance, turnkey rental properties, and real estate cash flow as part of his broader “wealth outside Wall Street” philosophy and discusses his book: Retire In 10 Years or Less. → Full show notes with direct links to everything discussed are available here.

  5. Jun 2

    How Women Real Estate Investors Succeed Through Focus, Systems and Community with Liz Faircloth (Ep 2)

    Hear why the right market selection, mentorship, community & disciplined scaling system matter more than chasing deals. 👉 Want to build a cash-flowing rental property portfolio from anywhere? Watch my Free Training on How To Buy Turnkey Rental Properties in the most investor-advantaged U.S. real estate markets Liz Faircloth shares the lessons she learned scaling from buying a single duplex to building and managing a large multifamily real estate portfolio across multiple states.   She explains why market selection matters more than chasing individual deals, how the right systems can prevent investors from “scaling chaos,” and why mentorship and community can dramatically shorten the learning curve for real estate investors. Liz also reflects on the mistakes she made early in her investing journey, including overextending into too many asset classes at once.  She discusses how disciplined scaling, multifamily investing, and intentional networking helped her build long-term wealth. In addition, she shares the mission behind InvestHER and how her team supports women real estate investors through education, mentorship, live events, and community. → Full show notes with direct links to everything discussed are available here.

    How Women Real Estate Investors Succeed Through Focus, Systems and Community with Liz Faircloth (Ep 2)

  6. May 26

    Stop Looking at Properties: Keith Weinhold’s Contrarian Strategy to Build Real Estate Wealth (Ep 1)


    Learn why you should stop looking at properties, use good debt to grow faster, and invest based on supply and demand. 👉 Want to build a cash-flowing rental property portfolio from anywhere? Watch my Free Training on How To Buy Turnkey Rental Properties in the most investor-advantaged U.S. real estate markets How do you build real estate wealth without starting with the property? In this episode, Keith Weinhold breaks down the contrarian investing framework he’s developed over 20+ years, beginning with why most investors get it backwards by focusing on properties first. He explains how to clarify your investment goals, choose the right market, and build a team before ever selecting a deal—especially when investing in out-of-state rental property markets. Keith also shares how he used leverage and other people’s money to scale from his first fourplex into a larger portfolio, why “good debt” can dramatically increase returns in real estate investing, and how supply and demand fundamentals—particularly the shortage of entry-level housing—continue to shape rental property opportunities today. Along the way, he offers practical insights for avoiding early mistakes and building long-term wealth through strategic, scalable real estate investing. → Full show notes with direct links to everything discussed are available here.

  7. May 26

    3 Real Estate Investing Lessons That Changed Matt Bowles' Life & Built Maverick Investor Group (Ep 0)

    Hear how positive cash flow, turnkey rentals, and investor-advantaged markets transformed Matt’s entire investing approach. 👉 Want to build a cash-flowing rental property portfolio from anywhere? Watch my Free Training on How To Buy Turnkey Rental Properties in the most investor-advantaged U.S. real estate markets Matt Bowles shares his personal journey from working a nonprofit office job and buying rental properties on the side to co-founding Maverick Investor Group. Matt reflects on the early investing mistakes that cost him money and stress during the 2008 financial crisis and explains the three core real estate investing lessons that ultimately transformed his strategy: prioritizing positive cash flow, mitigating risk through turnkey rental properties, and buying in investor-advantaged real estate markets. He also breaks down how these lessons shaped the long-term investment philosophy behind Maverick Investor Group and how his clients now build their rental property portfolios across the United States based on the same core principles.  Matt also introduces the podcast and explains how each subsequent episode will be asking experienced real estate investors to reflect on their journey and identify the 3 real estate investing they wish they knew when they were starting out.  Whether you are new to real estate investing or already growing your portfolio, this podcast will provide insights and wisdom that can help you avoid mistakes, mitigate risk, and get ahead faster. → Full show notes with direct links to everything discussed are available here.

  8. May 25

    Trailer: 3 Real Estate Investing Lessons I Wish I Knew


    Welcome to 3 Real Estate Investing Lessons I Wish I Knew, hosted by Matt Bowles of Maverick Investor Group. In each episode, experienced real estate investors reflect on their journeys and share the 3 most important lessons they wish they knew when getting started. Conversations cover turnkey rental properties, financing, tax strategies, portfolio scaling, passive income, mindset, financial freedom, and building long-term wealth through real estate investing. Whether you are buying your first rental property or growing an existing portfolio, this show is designed to help you make smarter decisions, avoid costly mistakes, and get ahead faster. New interviews drop every other Tuesday. Follow the show so you never miss an episode.

Trailer

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About

Experienced real estate investors reflect on their journeys and share the 3 most important lessons they wish they knew when getting started. Hosted by Matt Bowles of Maverick Investor Group, this show draws out practical lessons about turnkey rental properties, financial freedom, portfolio growth, tax strategy, and building long-term wealth through real estate. Each episode breaks down the specific strategies, mistakes, mindset shifts, and investing principles that helped guests scale their portfolios and create more freedom in their lives. Topics include long-term rental properties, short-term rentals, medium-term rentals, passive income, self-directed IRAs, bonus depreciation, financing, leverage, market selection, asset protection, and remote real estate investing. Guests also share candid stories about overcoming fear, analyzing deals, managing risk, and using real estate investing to create more flexibility, location independence, and lifestyle freedom. Whether you are buying your first rental property or growing a large portfolio, this podcast is designed to help you learn faster, avoid costly mistakes, and make smarter investing decisions.

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