Real Estate Investor Podcast
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.
Episodes
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 savi...
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...
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 capita...
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 toge...
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...
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 ...
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 pro...
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 explain...
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 matt...
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...
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 hi...
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,...
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 res...
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 t...
How do family offices think about real estate, relationships, and market timing when the rest of the market is still waiting for certainty? In this episode of the Real Estate Investor Podcast, host Gary Lipsky sits down with DJ Van Keuren to unpack how family offices really approach real estate investing. DJ is s a Harvard-trained strategist, the Co-Founder of Evergreen Property Partners, President of the Harvard Real Estate Alumni...
Building a real estate deal today feels like solving an increasingly complex puzzle, as investors face a more selective market. They must now work harder than ever to assemble a capital stack that truly pencils. Returning to the show is Andrew Westling, Director of Capital Markets at Walker & Dunlop in Los Angeles, joining Gary to share deep insights into today’s financing landscape. Together, they break down the current ...
Do you want to get rich beyond belief? Today on the Real Estate Investor Podcast, master coach and real estate investor, Trevor McGregor, joins us to talk about how you can achieve high-performance and true success! Tuning in, you’ll hear all about his investment background and career, what the investor wealth architect identity shift is, stepping into your sage mindset, and so much more. He delves into the five reasons why p...
When we hit rock bottom, the only place to go is up! Today on the Real Estate Investor Podcast, we welcome real estate entrepreneur, author, host of the top-rated podcast, Investing in the U.S., and founder of Accounting First Group, Reed Goossens, to discuss his stance in the erratic real estate investing world at the moment and to learn about his CPA firm rollup! Tuning in, you’ll hear all about Reed’s impressive care...
What does it look like to switch from closing deals to building communities with real long-term impact? In this episode of the Real Estate Investor Podcast, host Gary Lipsky sits down with Ian Tudor, partner at JIK Holdings, to discuss Ian’s career path from corporate finance to mobile home parks and into land development. Ian shares how institutional underwriting influenced his investing mindset, how he and his partners buil...
In this episode of the Real Estate Investor Podcast, Gary Lipsky welcomes back Joseph Fang of Break of Day Capital to unpack the current real estate market signals and how those signals are shaping new opportunities on the acquisition side. Joseph shares why basis and buying below replacement cost matter in today’s environment, what a value-add plan looks like when it’s focused on deferred maintenance, and how targeted ...
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