Real Estate Investor Podcast

Hosted by Gary Lipsky

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Episodes

273

Latest episode

Oct 2026

Language

EN-US

About the show

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.

Listen to episodes

60 recent

October 23, 2026Episode 27515 min

Refinance or Sell: Navigating the Multifamily Reset with Gary Lipsky

One of the most difficult decisions to make in multifamily real estate is whether to refinance, sell, or hold onto a property! Today on the Real Estate Investor Podcast, host Gary Lipsky is helping listeners to navigate the multifamily reset. In this conversation, you’ll hear all about how financing has changed over the years, the challenges investors are facing, when selling a property is the best option, the danger of selling in a weak market, and more! We delve into different refinancing options, the pros and cons of each, and how to know if it’s right for you before discussing why a good property and a good investment aren’t always the same thing. Gary also breaks down the three things he is most focused on when it comes to investments. Finally, he shares why he is still very optimistic about the future of multifamily real estate and how investors can mitigate risk. Thanks for tuning in! Key Points From This Episode: Today’s topic: the multifamily reset. Understanding today’s refinancing challenges. What happens when a loan matures in this scenario. When selling a property is the best financial option. A breakdown of the pros and cons of refinancing options. The difference between a good property and a good investment. Three things Gary focuses on when he invests in multifamily. What Gary thinks the future holds for multifamily. The importance of managing today’s risks. 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 .

October 2, 2026Episode 27446 min

Nathan Sosa – Year End Tax Strategies

Tax planning is one of the most powerful things you can do to save money as a real estate investor. Today on the Real Estate Investor Podcast, we are joined by the manager of both the National Tax Department and the Audit Defense Division at Hall CPA, Nathan Sosa, to discuss some end-of-year tax strategies. Tuning in, you’ll hear why passive tax planning is so problematic, the power of using tax strategies as a method of saving, Hall CPA’s tax philosophy, and more. We delve into key tax strategies that can be employed to help real estate investors better prepare for taxes and hear all about potential tax dangers and what to avoid. Nathan also shares one of his most powerful tax strategies: ‘buy, borrow, die.’ From strategies for investors with real estate professional status to using oil and gas investments to offset your taxes, this episode is jam-packed with helpful tips that will prepare you for the next tax season. You don’t want to miss this one, so be sure to press play now! Key Points From This Episode: Welcoming today’s guest, Nathan Sosa. The problem of passive tax planning. Nathan explains Hall CPA’s tax philosophy. Real estate professional status tax strategies. What the short-term rental loophole is. The benefits of using a cost segregation study. Tax strategies for people selling a property. Lazy 1031: the bonus depreciation strategy. Using oil and gas investments to offset tax. How employing your children can be beneficial. When Nathan does and doesn’t recommend S corps. Home office deduction as an advanced tax strategy. What opportunity zones are and how to leverage them. Some retirement tax strategies that can be utilized. A breakdown of the ‘buy, borrow, die’ tax strategy. Tax dangers with solar tax credits and equipment rentals. Strategies you can employ before the tax year ends. What to avoid when it comes to real estate tax. Links Mentioned in Today’s Episode: Nathan Sosa on LinkedIn Nathan Sosa Email Hall CPA Tax Smart Real Estate Investors Podcast Major League Real Estate Podcast 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 .

September 18, 2026Episode 27315 min

Darshit Shah — Beyond the Property Management Report

In this episode, Gary Lipsky interviews Darshit Shah, founder of Orizon Asset Management, on how fractional asset management can help multifamily operators uncover overlooked opportunities and improve NOI. Darshit shares how he combines AI tools like Claude and Obsidian with human oversight to analyze property reports, benchmark expenses, and identify missed revenue from items such as pet fees, late fees, and utility reimbursements. He also explains why economic occupancy can be more revealing than physical occupancy, particularly when evaluating distressed assets, and highlights key metrics investors should monitor, including actual rent rolls, going-in cap rates, and DSCR. Tune in for another insightful episode of the Real Estate Investor Podcast. Key Points From This Episode: Introducing today’s guest, Darshit Shah. More about Darshit Shah and Orizon Asset Management. He unpacks the reports they provide to operators. Darshit sheds light on the stack he uses behind the management company. He explains why he uses Obsidian. How they ensure tight, clean, and efficient data ingestion for clients. Darshit shares common mistakes operators are making in the current market. How they are identifying small misses and the necessity of having a human in the loop. Real-world examples of how occupancy metrics can be misleading. Key indicators passive investors should monitor when investing in a deal. The primary metrics operators should not overlook. Learn more about Darshit and Orizon Asset Management. Links Mentioned in Today’s Episode: Darshit Shah on LinkedIn Orizon Asset Management Claude Obsidian 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 .

September 11, 2026Episode 27242 min

Your Investment North Star with Matt King

What keeps a compelling opportunity from pulling you off course? In this episode of the Real Estate Investor Podcast, host Gary Lipsky welcomes back Matt King, CEO of GoBundance and leader of DRO Investments, for a session recorded at the 2026 Virtual Invest Smart Summit. Matt shares a practical framework for defining a family investment thesis, evaluating risk more intentionally, and making disciplined decisions about where capital does and does not belong. They also explore using artificial intelligence as a thinking partner, teaching the next generation to invest, and balancing long-term conviction with changing market conditions. Tune in to find your investment north star and approach the next opportunity with a clearer lens. Key Points From This Episode: Learn why a clear investment thesis separates disciplined investors from reactive ones. Discover how defining your investment goals brings greater intention to every decision. Find out how to reframe risk as a lack of knowledge or as a calculated bet. Steps to build a clear investment thesis and how to apply it to every deal. Explore why sophisticated family offices are slow to say yes. Hear how theRide aims to raise $1 million for overlooked communities. The role of AI tools and why effective prompt engineering is essential. Explore how to teach and explain investing through guided practice. Consider what it takes to become a disciplined investor and build generational wealth. Understand how conviction can coexist with a flexible risk appetite. Find out how Matt keeps up to date on the latest investment news and trends. He provides a review of IRR, MOIC, liquidity, and other metrics for returns. Links Mentioned in Today’s Episode: Matt King on LinkedIn Matt King GoBundance theRide Invest Smart Summit All-In Podcast Episode 213: Living a Life of Abundance with Matt King Rich Dad Poor Dad The Richest Man in Babylon 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 .

August 28, 2026Episode 27124 min

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 .

August 21, 2026Episode 27017 min

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 .

August 7, 2026Episode 26933 min

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 .

July 31, 2026Episode 26818 min

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 .

July 17, 2026Episode 26723 min

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 .

July 3, 2026Episode 26614 min

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 .