Real Estate Investor Podcast

Gary Lipsky
  • 5.0 (19)
  • Investing
  • Updated Weekly

The Real Estate Investor Podcast, powered by Break of Day Capital, brings you in-depth conversations with the top minds in real estate investing. Each episode uncovers proven strategies and lessons learned across multifamily, commercial, and other alternative asset classes. Whether you’re a seasoned investor or just starting out, you’ll gain practical tools and real-world wisdom to help you invest smarter, avoid pitfalls, and build long-term wealth through passive income. 

  1. 1d ago

    Episode #268 - Understanding Delaware Statutory Trusts

    If you’re wondering how to defer taxes and diversify wealth on your stock in a meaningful way, this episode is for you. Brett Swarts builds capital gains tax exit plans. He is a real estate investment advisor, podcaster, best-selling author, and a California multi-family broker, and the founder of Capital Gains Tax Solutions and EXB Commercial Multi-Family Broker. Each year, he equips hundreds of millionaires and business professionals with the deferred sales trust tools to help solve capital gains tax deferral limitations. First, the conversation covers the basics of 1031 exchanges and Deferred Sales Trusts, including how they benefit SpaceX employees and support long-term wealth preservation. Next, it explores tax-saving strategies, the value of layering financial solutions, and how Brett uses DSTs to solve challenges like partnership dissolutions. Lastly, we unpack the power that passive income can unlock and what that might look like for you. Thanks for listening!  Key Points From This Episode: Background on Brett Swarts.How Brett’s business helps people create capital gains tax exit plans.The basics of a 1031 and Deferred Sales Trust.How this works for former or current SpaceX employees.Why this strategy is such a valuable option.Adopting a mindset of layering, sequencing, and compilation. Different strategies to offset income tax. Using a DST as a lifeline.How Brett provides smooth solutions to dissolving partnerships.The power of passive income. Links Mentioned in Today’s Episode: Brett Swarts Brett Swarts on LinkedIn Brett Swarts on Instagram Capital Gains Tax Solutions Building a Capital Gains Tax Exit Plan Asset Management Mastery Facebook Group Invest Smart Break of Day Capital Break of Day Capital Instagram Break of Day Capital YouTube Gary Lipsky on LinkedIn 🙏 Special thanks to our sponsor, Bromley Palamountain of Northwestern Mutual — helping professionals and business owners build financial plans that support long-term freedom. To book your complimentary consultation, click the link.

  2. Jul 17

    Episode #267 - The Insurance Playbook with Ryan Thomas

    Insurance can make or break a multifamily deal, especially when markets are volatile, lender requirements are tightening, and prior claims can affect pricing for years. In this episode of the Real Estate Investor Podcast, Gary Lipsky sits down with Ryan Thomas, a commercial insurance advisor specializing in multifamily real estate, to discuss what investors need to know before buying, refinancing, or renewing coverage. Ryan explains what has changed in the commercial insurance market, why the property market is softening, and why liability coverage is becoming harder to navigate. He breaks down how Fannie Mae and Freddie Mac requirements are affecting coverage for claims, why some investors may face large retainers, and how lender requirements can create challenges. Ryan shares why working with an experienced broker matters, how underwriter relationships can influence outcomes, and how a master policy can help investors manage coverage across a portfolio. Tune in to learn how to get ahead of insurance issues before they become problems with Ryan Thomas. Key Points From This Episode: Background about Ryan and how he became a commercial insurance advisor.What has changed in the insurance market for acquisitions and refinances.Discover why Arizona remains a more favorable insurance market than other states.Understand how agency requirements are affecting coverage.Uncover what smaller investors need to consider before using agency debt.Explore how prior claims and five-year loss runs can impact insurance pricing.Hear why a strong insurance broker can make a major difference during acquisitions.Find out what investors should review before making an offer.Learn the difference between admitted and non-admitted insurance carriers.Unpack the role of broker commissions, fees, and underwriter relationships.How master policies work and why they can benefit multifamily portfolios.Advice on what investors should look for when choosing an insurance broker.Links Mentioned in Today’s Episode: Arcstone Insurance Advisors Email Ryan Thomas  Call Ryan Thomas Fannie Mae Freddie Mac  Asset Management Mastery Facebook Group Invest Smart Break of Day Capital Break of Day Capital Instagram Break of Day Capital YouTube Gary Lipsky on LinkedIn 🙏 Special thanks to our sponsor, Bromley Palamountain of Northwestern Mutual — helping professionals and business owners build financial plans that support long-term freedom. To book your complimentary consultation, click the link.

  3. Jul 3

    Episode #266 - Weathering the Storm

    The last multifamily cycle exposed some hard truths—and the investors who learn from them will be better positioned for whatever comes next. In this episode, Gary Lipsky breaks down the five biggest underwriting lessons from the recent downturn, explaining why refinancing is a risk, not a strategy, why rent growth can't rescue a weak business plan, and why break-even occupancy, conservative leverage, and healthy reserves matter more than ever. He also challenges the mindset behind "Survive until '25" and "Persist until '26," explores what truly separates great operators from the rest, and shares the critical questions every passive investor should be asking before investing in a deal. If the market is repricing risk, not just real estate, this conversation will help you adapt your investment strategy and position yourself to thrive when the next cycle begins. Key Points From This Episode:  Introduction to today’s topic of discussion.Why the sayings “Survive until ’25” or “Persist until ’26” won’t do you any good.The true test of an operator.Why not all deals were bad deals.Lesson one: refinancing is a risk, not a strategy.What happens if refinancing is not available?Lesson two: rent growth cannot beat the business plan.An uncomfortable truth from the last cycle.Important questions investors should consider.Lesson three: break-even occupancy matters more than projected returns.Critical questions for investors regarding break-even occupancy.Lesson four: maximum leverage doesn't always maximize returns.Lesson five: reserves are not dead money.What investors should be asking regarding reserves.The biggest lesson we learned from this cycle: the market isn't just repricing real estate, it’s repricing risk.The good news after the downturn.The biggest mistakes investors can make today.Where will you be positioned when the storm ends?Links Mentioned in Today’s Episode: Asset Management Mastery Facebook Group Invest Smart Break of Day Capital Break of Day Capital Instagram Break of Day Capital YouTube Gary Lipsky on LinkedIn 🙏 Special thanks to our sponsor, Bromley Palamountain of Northwestern Mutual — helping professionals and business owners build financial plans that support long-term freedom. To book your complimentary consultation, click the link.

  4. Jun 26

    Episode #265 - Dr. Peter Linneman - Reality vs. Narrative: A Midyear Market Check

    What if the story investors are reacting to isn’t the one the data is actually telling? This episode is a value-packed Town Hall with Dr. Peter Linneman, one of the most respected voices in finance, investing, and real estate. He shares incredible insights on a range of essential topics, including what investors are missing about the US economy, the political and economic factors shaping the market, and where he sees the best opportunities today. We also discuss the surprising strength of the latest jobs report, where interest rates may be headed, the state of commercial real estate, the outlook for multifamily housing, and the risks that could drive a future recession. Dr. Linneman also shares his biggest concerns, what could change his perspective this year, and his number one piece of advice for investors waiting for clarity. Don’t miss this deep dive. Key Points From This Episode: Dr. Peter Linneman’s background as a leader in finance and investments.What investors miss about the US economy.Predicted drivers of a future recession. How the political landscape is impacting the economy.Why the most recent job report had surprisingly positive results. Where Dr. Linneman predicts interest rates will go in the year to come.The state of commercial real estate. Dr. Linneman’s concerns and what would change his perspective this year.The country’s education problem and why it is a threat to the economy. Why there is hope for multifamily going forward.Advice for investors who are stuck and waiting for clarity.Links Mentioned in Today’s Episode: Dr. Peter Linneman on LinkedIn Linneman Associates Real Estate Finance & Investments: Risks and Opportunities, Second Edition REFAI Certification The Great Age Reboot Asset Management Mastery Facebook Group Invest Smart Break of Day Capital Break of Day Capital Instagram Break of Day Capital YouTube Gary Lipsky on LinkedIn 🙏 Special thanks to our sponsor, Bromley Palamountain of Northwestern Mutual — helping professionals and business owners build financial plans that support long-term freedom. To book your complimentary consultation, click the link.

  5. Jun 12

    Episode #264 - Building Investor Trust with Pat Zingarella

    How can passive investors distinguish trustworthy real estate operators from those who simply know how to market themselves? In this episode of the Real Estate Investor Podcast, host Gary Lipsky sits down with Pat Zingarella, CEO of Invest Clearly, a public directory and review platform for private real estate investments. In their conversation, Pat explains how his experience working for a fraudulent real estate investor showed him the need for greater transparency across the industry. He shares how Invest Clearly verifies that reviewers have invested with the sponsors they evaluate, why communication breakdowns remain the most common investor complaint, and how verified reviews can help responsible GPs stand apart. Gary and Pat also discuss the importance of evaluating the operator before the deal, reporting unsuccessful investments honestly, and the LPs’ responsibility to conduct proper due diligence. Tune in to explore the changing capital-raising environment, the growing cost of converting prospective investors, and why more leads cannot replace trust, with Pat Zingarella. Key Points From This Episode: Background about Pat and why he founded Invest Clearly.Learn how verified reviews help strong operators stand out.Discover why communication matters more than a perfect record.Find out what makes Invest Clearly stand out from other companies.Hear how sponsors should address poor-performing deals.Uncover the sponsor red flags investors often overlook.Understand why LPs must take ownership of due diligence.Explore what Pat is planning next for Invest Clearly.Get insights into how transparency fosters trust with investors.Unpack why and how investor conversion has changed.Links Mentioned in Today’s Episode: Pat Zingarella on LinkedIn Pat Zingarella Email Invest Clearly Asset Management Mastery Facebook Group Invest Smart Break of Day Capital Break of Day Capital Instagram Break of Day Capital YouTube Gary Lipsky on LinkedIn 🙏 Special thanks to our sponsor, Bromley Palamountain of Northwestern Mutual — helping professionals and business owners build financial plans that support long-term freedom. To book your complimentary consultation, click the link.

  6. May 29

    Episode #263 - The New Investment Landscape

    What does today’s economic uncertainty mean for real estate investors trying to make smart decisions? In this episode of the Real Estate Investor Podcast, host Gary Lipsky sits down with J Scott, entrepreneur, investor, advisor, author, and partner at Bar Down Investments, for a timely conversation recorded during the 2026 Virtual Invest Smart Summit. J shares his perspective on the Federal Reserve, inflation, interest rates, lending conditions, and the broader market signals investors should be watching. He explains why mortgage rates do not always move with the Fed rate, how inflation expectations influence borrowing costs, and why he believes investors should prepare for a weaker economy and tighter lending environment. They discuss opportunities across single-family, multifamily, and commercial real estate, as well as the importance of choosing lenders carefully in a changing market. They also explore AI’s potential impact on inflation, jobs, education, wages, and long-term real estate values. Tune in to learn why investors should return to fundamentals, build conservative pro formas, secure longer-term debt, and focus on buying right with J Scott. Key Points From This Episode: Hear J’s view on Kevin Warsh, Federal Reserve policy, and possible changes to inflation.Explore how inflation projections drive mortgage and other market-based interest rates.Find out why J sees signs of economic softening, tighter lending, and a possible recession.Learn why J believes inflation could still support single-family and residential real estate.Understand why multifamily may be near the bottom after several difficult years.Why he expects mortgage rates to remain in the 6% to 7% range for the next few years.How higher interest rates can create buying opportunities but make selling more difficult.J shares what economic data points he watches most closely as a real estate investor.Advice on using online tools, government reports, and AI to understand market data.Unpack why J thinks AI will be inflationary in the short term and deflationary in the long term.Discover why the fundamentals, conservative underwriting, and longer-term debt are key.Links Mentioned in Today’s Episode: J Scott J Scott on LinkedIn J Scott on Linktree Bar Down Investments BiggerPockets Books MarketWatch Economic Calendar Invest Smart Summit Asset Management Mastery Facebook Group Invest Smart Break of Day Capital Break of Day Capital Instagram Break of Day Capital YouTube Gary Lipsky on LinkedIn 🙏 Special thanks to our sponsor, Bromley Palamountain of Northwestern Mutual — helping professionals and business owners build financial plans that support long-term freedom. To book your complimentary consultation, click the link.

  7. May 22

    Episode #262 - Kathy Fettke — 2026 Economic Outlook

    This special episode of The Real Estate Investor Podcast was recorded for the 2026 Virtual Investment Summit. Host Gary Lipsky interviews returning guest, Kathy Fettke, to break down the 2026 economic outlook and what it means for real estate investors navigating today’s shifting market. Kathy shares why the single-family housing market remains more resilient than many expect, while multifamily assets are entering a major reset driven by rising delinquencies, distressed debt, and changing market fundamentals. Just as it seems that a sense of fear is rising in this sector, so too is there a tremendous amount of opportunity. Furthermore, they discuss why affordability is becoming the defining trend in U.S. housing, how migration toward Midwest and Sunbelt markets is creating new opportunities, and why disciplined underwriting and long-term cash flow strategies are more important than ever. They reflect on lessons from the 2009 financial crisis, break down a practical 1031 exchange strategy, and Kathy explains how investors can build wealth by providing attainable housing solutions during a time of nationwide housing shortages. Key Points From This Episode: What listeners can expect from today’s episode.Kathy explains why the state of U.S housing is important. Buying in bubble markets.Why so many people love the steady states in the Midwest.The bubble market reset and why it’s an opportunity to make money.Will there be an inevitable crash ahead in the one-to-four-unit world?How debt and equity in 2026 differ from 2009 (in one-to-four-units).Kathy highlights a distinct difference in mortgages between 2009 and 2026.The real distress today: U.S. renters.How the Trump Administration is attacking Wall Street-owning homes.What we are seeing: people choosing affordability.How buy-and-hold investors can solve the affordability problem.Kathy shifts from the single-family to the multi-family economic outlook for 2026.Finding the best deals and investing where people are moving toward.They unpack a practical 1031 exchange strategy.What it was like investing in 2009.The importance of knowing how to underwrite.Links Mentioned in Today’s Episode: Kathy Fettke Kathy Fettke on LinkedIn Kathy Fettke on Instagram Real Wealth Network Kathy Fettke Real Wealth Podcast Kathy Fettke Real Wealth Network on YouTube Raising & Investing 2026 Virtual Investment Summit Robert Kiyosaki: Financial Literacy, Investing & Big Money Ideas! Asset Management Mastery Facebook Group Invest Smart Break of Day Capital Break of Day Capital Instagram Break of Day Capital YouTube Gary Lipsky on LinkedIn

  8. May 8

    Episode #261 - Gary Lipsky – Invest Smart Summit Takeaways and Closing a Deal

    How can investors make smarter decisions in a market that looks very different from just a few years ago? In this solo episode of the Real Estate Investor Podcast, host Gary Lipsky shares key takeaways from the Invest Smart Summit and breaks down Break of Day Capital’s recent closing of Icon on Broadway. Gary begins by explaining why today’s market should be viewed as a reset rather than a collapse, why investors need to understand individual markets, and why staying on the sidelines too long can become its own risk. He breaks down important considerations around tax planning, investment strategy development, interest rates, inflation, and AI. Gary also walks listeners through the Icon on Broadway deal, how the team evaluated the asset, and what they aim to achieve with the new business plan. Tune in to hear how disciplined investing and market knowledge can help investors navigate uncertainty and identify opportunities that are built on fundamentals, not speculation. Key Points From This Episode: Why the summit focused on investing, taxes, wellness, and market insights.Learn why today’s market is going through a reset rather than a collapse.Understand why real estate investors need to evaluate markets individually.Hear why it is critical to follow the fundamentals and not the headlines.Discover why your tax strategy should be planned before investing.Insights into how higher rates affected different real estate asset classes.Explore why a clear investing approach helps avoid reacting to every deal.Find out how the Federal Reserve influences rates and market expectations.Gary details the Icon on Broadway deal and why it was compelling. The power of scale and how Break of Day Capital mitigates risk.Links Mentioned in Today’s Episode: The Invest Smart Summit Kathy Fettke Dean Indot on LinkedIn Bronson Hill on LinkedIn Ryan Kennedy Amanda Han Matt MacFarland on LinkedIn Matt King on LinkedIn Asset Management Mastery Facebook Group Invest Smart Break of Day Capital Break of Day Capital Instagram Break of Day Capital YouTube Gary Lipsky on LinkedIn 🙏 Special thanks to our sponsor, Bromley Palamountain of Northwestern Mutual — helping professionals and business owners build financial plans that support long-term freedom. To book your complimentary consultation, click the link.

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5
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About

The Real Estate Investor Podcast, powered by Break of Day Capital, brings you in-depth conversations with the top minds in real estate investing. Each episode uncovers proven strategies and lessons learned across multifamily, commercial, and other alternative asset classes. Whether you’re a seasoned investor or just starting out, you’ll gain practical tools and real-world wisdom to help you invest smarter, avoid pitfalls, and build long-term wealth through passive income. 

Information

  • Creator
    Gary Lipsky
  • Years Active
    2021 - 2026
  • Episodes
    267
  • Rating
    Clean
  • Copyright
    © 2026 Real Estate Investor Podcast
  • Show Website
    Real Estate Investor Podcast

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