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. Aug 28

    Building Wealth Beyond the Deal with Bromley Palamountain

    What does it take to turn a growing net worth into lasting financial freedom? In this episode of the Real Estate Investor Podcast, host Gary Lipsky sits down with Bromley Palamountain, RICP®, Wealth Management Advisor at Northwestern Mutual, to explore how thoughtful financial planning can help investors make more of what they earn and keep more of what they build. Bromley explains why tax and investment strategies should work together, how fad investing can pull portfolios off course, and what investors should consider when balancing traditional and alternative assets. He also shares his approach to liquidity, the role real estate can play in a diversified portfolio, and why a long-term mindset matters during periods of volatility. They also discuss the habits Bromley sees among his most successful clients and one simple strategy for moving closer to financial independence. Tune in to learn how clarity, coordination, and consistency can help you build wealth beyond the deal with Bromley Palamountain. Key Points From This Episode: Meet Bromley Palamountain and hear how his team helps clients manage their finances.Explore why aligning tax and investment strategies can change what investors keep.Learn about the costly financial mistakes that high-net-worth investors repeatedly make.When alternative investments may make sense alongside traditional stocks and bonds.Hear how to balance liquidity and opportunity without being forced into the wrong strategy.Consider the role real estate can play in building a well-rounded portfolio.Practical steps to navigate uncertainty without losing sight of the bigger financial picture.Uncover the habits that set Bromley’s most successful clients apart.He breaks down his best strategy for achieving financial independence.Links Mentioned in Today’s Episode: Bromley Palamountain Bromley Palamountain on LinkedIn Email Bromley Palamountain Northwestern Mutual Schedule your Complimentary Financial Planning Call Tom Wheelwright Invest Smart Summit Who Not How GoBundance 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. Aug 21

    Tim Fergestad — Think Better. Invest Better.

    What happens to your wealth when you stop earning an income? For Dr. Tim Fergestad, true wealth comes from owning assets rather than relying solely on earned income. In this episode, Gary Lipsky sits down with Dr. Tim Fergestad, a neuroscientist turned real estate investor and the Founder and Managing Partner of Oak Street Assets. Dr. Fergestad shares his journey from traditional investments and hands-on real estate to syndications, and how his scientific background shapes the way he evaluates opportunities. He unpacks the “earned income trap,” why capital ownership matters, and what he looks for when vetting syndications, including why evaluating the operator should come before evaluating the deal. Dr. Fergestad also explores how market cycles, fear, negativity bias, and herd behavior influence investors and explains how having a framework can help reduce the impact of emotions when making decisions under uncertainty. Listen in for insights on building wealth through ownership and becoming a more disciplined investor! Key Points From This Episode: Introducing Dr. Tim Fergestad and his transition from neuroscience to real estate.His move from hands-on real estate investing to passive syndications.How his scientific background shapes his approach to evaluating investments.The “earned income trap” and why asset ownership is key to building wealth.Top things Dr. Fergestad looks for when evaluating a syndication.The importance of strong operators who can adapt and pivot through challenges.Why market downturns can create opportunities for real estate investors.The role of negativity bias and herd behavior in investment decisions.Why successful investors need to question the herd rather than follow it.Using experience and a framework to make better decisions under uncertainty.Links Mentioned in Today’s Episode: Dr. Tim Fergestad on LinkedIn Dr. Tim Fergestad Linktree Oak Street Assets Oak Street Assets on YouTube Oak Street Assets on Facebook Oak Street Assets: The Real Estate Syndication First-Pass Scorecard Phoenix Prosperity Podcast Good to Great: Why Some Companies Make the Leap...and Others Don't Great by Choice: Uncertainty, Chaos, and Luck--Why Some Thrive Despite Them All 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. Aug 7

    Episode #269 - The Data Behind Multifamily with Jeff Adler

    What does the latest multifamily data reveal about where the next real estate opportunities lie? In this episode of the Real Estate Investor Podcast, host Gary Lipsky welcomes Jeff Adler, Lead Executive at Yardi Matrix, for a data-driven conversation on the forces shaping multifamily real estate. Jeff shares his perspective on today's market, breaking down the impact of new supply, shifting apartment demand, and why rent growth is entering a new phase. He also explores the broader economic backdrop, including what some are calling a "silent recession,” and discusses how institutional capital is positioning itself as investors wait for greater market clarity. The conversation concludes with Jeff's outlook on the markets best positioned for growth over the next three to five years and the biggest risk he believes multifamily investors should be monitoring over the next 24 months. Tune in for valuable market insights to help you navigate today's evolving investment landscape with greater confidence. Key Points From This Episode: An introduction to today’s guest, Jeff Adler. More about Yardi Matrix.Jeff’s thoughts on where multifamily stands today.The trickle-down effect and how it’s affecting the demand for apartments.Jeff dives into some predictions regarding rent growth.Explaining the broader economic backdrop and the silent recession.His take on “the big capital” sitting on the sidelines, waiting for the bottom.Emerging markets: those best positioned for the next 3-5 years.The single biggest risk Jeff is keeping an eye on over the next 24 months.Where to learn more about Jeff and Yardi Matrix. Links Mentioned in Today’s Episode: Jeffrey W. Adler on LinkedIn Jeffrey W. Adler Yardi Matrix Yardi Matrix Ray Dalio 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.

  4. Jul 31

    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.

  5. 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.

  6. 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.

  7. 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.

  8. 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.

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5
out of 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
    270
  • Rating
    Clean
  • Copyright
    © 2026 Real Estate Investor Podcast
  • Show Website
    Real Estate Investor Podcast

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