Real Estate Investor Podcast

Hosted by Gary Lipsky

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Episodes

263

Latest episode

Jun 2026

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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.

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June 12, 2026Episode 26422 min

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 LinkedInPat Zingarella EmailInvest ClearlyAsset Management Mastery Facebook Group Invest SmartBreak of Day Capital Break of Day Capital InstagramBreak of Day Capital YouTubeGary 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.

May 29, 2026Episode 26343 min

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 ScottJ Scott on LinkedInJ Scott on LinktreeBar Down InvestmentsBiggerPockets BooksMarketWatchEconomic CalendarInvest Smart SummitAsset Management Mastery Facebook Group Invest SmartBreak of Day Capital Break of Day Capital InstagramBreak of Day Capital YouTubeGary 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.

May 22, 2026Episode 26237 min

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 FettkeKathy Fettke on LinkedInKathy Fettke on InstagramReal Wealth NetworkKathy Fettke Real Wealth PodcastKathy Fettke Real Wealth Network on YouTubeRaising & Investing 2026 Virtual Investment SummitRobert Kiyosaki: Financial Literacy, Investing & Big Money Ideas!Asset Management Mastery Facebook Group Invest SmartBreak of Day Capital Break of Day Capital InstagramBreak of Day Capital YouTubeGary Lipsky on LinkedIn

May 8, 2026Episode 26112 min

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 SummitKathy FettkeDean Indot on LinkedInBronson Hill on LinkedInRyan KennedyAmanda HanMatt MacFarland on LinkedInMatt King on LinkedInAsset Management Mastery Facebook Group Invest SmartBreak of Day Capital Break of Day Capital InstagramBreak of Day Capital YouTubeGary 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.

May 1, 2026Episode 26019 min

Episode #260 - DJ Van Keuren - How Family Offices Really Invest

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 Association, and Founder of the Family Office Real Estate (FORE) Institute. He has held senior real estate positions at several prominent family offices where his work has focused on helping families invest in real estate. In this conversation, DJ explains what a family office actually is, how single-family and multifamily offices differ, and why real estate remains such a meaningful part of many family office portfolios. He discusses why family offices are paying attention to the current market reset, how they are preparing to deploy capital, and why multifamily remains one of their preferred asset classes. DJ also shares advice for operators who want to build relationships with family offices and uncovers why leading with a deal is usually the wrong approach. Tune in to learn why patience matters, why communication becomes even more important when things do not go perfectly, and how family offices think, invest, and build generational wealth through real estate with DJ Van Keuren.Key Points From This Episode:DJ’s background in family office real estate and how he got into the space.He explains the definition of a family office and how many offices exist in the US. Learn why DJ uses USD 250 million as a key threshold for a single-family office.Why family offices typically allocate around 24.5% of their portfolios to real estate.Get an overview of the investment and tax benefits of family real estate.Hear why DJ thinks the next 18 months could create major opportunities for investors.Understand the difference between retail investors and experienced investors.The 18.6-year real estate cycle and why downturns can be strong buying periods.Find out how much work happens behind the scenes in real estate investing.Uncover where family offices are focusing their attention in the current market.Discover why and when operators should build relationships with family offices.Advice for attracting family office capital and quality investors.Links Mentioned in Today’s Episode:DJ Van KeurenDJ Van Keuren EmailDJ Van Keuren on LinkedInEvergreen Property PartnersFamily Office Real Estate (FORE) InstituteThe Harvard Real Estate Alumni Organization (HREAO)Asset Management Mastery Facebook Group Invest SmartBreak of Day Capital Break of Day Capital InstagramBreak of Day Capital YouTubeGary 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

April 10, 2026Episode 25922 min

Episode #259 - Andrew Westling - Inside the Capital Stack

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 lending environment, explore the differences between preferred and common equity, and examine where market sentiment is shifting. Andrew also highlights the most aggressive lenders across asset classes, explains how swaps work, and provides updates on HUD and CMBS lending. Tune in now to learn more about the complexities of completing a successful capital stack and how to get creative with raising capital. Key Points From This Episode:Listeners are introduced to Andrew Westling.Andrew delves into his thoughts on the current lending environment.Preferred equity versus common equity, and what Andrew is seeing in the markets.He sheds light on the current most aggressive lenders in different asset classes.The range of rates that aggressive lenders are providing.He explains what a swap is.Andrew speaks to the latest from HUD and CMBS lenders, and what they are.They discuss the complexities of completing your cap stack.Getting creative with raising capital. Links Mentioned in Today’s Episode:Andrew Westling on LinkedInAndrew Westling Phone Number: +1 310 979 5756Walker & DunlopAsset Management Mastery Facebook Group Invest SmartBreak of Day Capital Break of Day Capital InstagramBreak of Day Capital YouTubeGary 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.

March 27, 2026Episode 25825 min

Episode #258 - Trevor McGregor – How to Achieve High Performance

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 people fail to scale consistently before discussing how he maximizes his time. Trevor also touches on what he believes is the secret to living: sharing our success with beginners, and tells us how he went from losing everything to having a large, cash-flowing portfolio. Finally, our guest shares his favorite quote of all time and tells us where we can find his special free gift for listeners. If you want more success, wealth, and freedom, then this episode is for you, so be sure to press play now! Key Points From This Episode:Introducing Trevor McGregor.A brief overview of our guest’s career and investment journey. The investor wealth architect identity shift. Moving away from a saboteur mindset to a sage one. The five reasons people fail to scale consistently. Trevor tells us how he maximizes his time using AI. How he went from losing everything to where he is now. Trevor shares his favorite quotes with listeners. Links Mentioned in Today’s Episode:Trevor McGregorRich Beyond BeliefTrevor McGregor on LinkedInWho Not How Think and Grow RichAsset Management Mastery Facebook Group Invest SmartBreak of Day Capital Break of Day Capital InstagramBreak of Day Capital YouTubeGary 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.

March 13, 2026Episode 25721 min

Episode #257 - Reed Goossens – Opportunity in the Reset

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 career, his move from Australia to America, and how he’s adapted to survive in these difficult times in this industry. He goes on to talk about his opinion of the current state of investing and when and how he feels it will improve. We even chat about his new CPA firm rollup, Accounting First Group, what inspired him to start it, and his goals for the company. This is a thought-provoking and inspiring conversation that you don’t want to miss, so be sure to press play now! Key Points From This Episode:Welcoming Reed Goossens to the show. His thoughts on the real estate industry at the moment. Changes he’s made to push through this tough investing cycle. Where Reed will be investing in the near future and why. Reed tells us about his CPA firm rollup and his goals for it. Links Mentioned in Today’s Episode:Reed GoossensReed Goossens on LinkedInReed Goossens Email Address Reed Goossens on InstagramReed Goossens on FacebookInvesting in the U.S.Accounting First Group Asset Management Mastery Facebook Group Invest SmartBreak of Day Capital Break of Day Capital InstagramBreak of Day Capital YouTubeGary 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.

March 6, 2026Episode 25623 min

Episode #256 - Ian Tudor – The Pivot to Purpose

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 built a portfolio by buying smaller mobile home parks, and what he learned from living on-site to stabilize a large property. He breaks down land development for investors who are new to the space, the entitlement timeline, the upfront costs, and why development can sometimes feel slow and risky. Ian also shares details about his current work in Los Angeles County and his goal to create more attainable homeownership opportunities. To hear how Ian evaluates risk across strategies, what it takes to move from value-add to development, and why he believes this is a golden age for small developers, tune in now!Key Points From This Episode:Ian’s background and why he shifted from mobile home parks to land development.Hear how Ian’s start in corporate finance prepared him for real estate investing.Discover what got him interested in mobile home parks and why he went all-in.Learn how Ian and his partners built a mobile home park portfolio from scratch.What Ian learned from living on-site while helping turn around a large mobile home park.Unpack what changed in mobile home parks and why he decided to exit.Explore what land development involves and why the timeline is much longer.He shares how many deals he works on at once and why the pace can feel slow.Details about a big project Ian is currently working on and what it is trying to solve.Find out what the four-unit plan looks like in size, layout, and lot design.Insights into the progress of the project and the kinds of challenges he faces.Links Mentioned in Today’s Episode:Ian Tudor on LinkedInAsset Management Mastery Facebook GroupInvest SmartBreak of Day CapitalBreak of Day Capital InstagramBreak of Day Capital YouTubeGary 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.

February 13, 2026Episode 25518 min

Episode #255 - Joseph Fang – Market Signals and New Opportunities

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 fixes can improve resident experience, reduce turnover, and increase rent growth. They also discuss rate expectations, liquidity, lender behavior, and what Joseph and Gary are hearing across the market about timing, cap rates, expenses, and why strong asset management execution is becoming essential again. Tune in to learn what it takes to buy and operate confidently in an uncertain cycle with Gary Lipsky and Joseph Fang!Key Points From This Episode:Welcome back to Joseph Fang, Director of Investor Relations at Break of Day Capital.Hear about an exciting new deal that Break of Day Capital has closed on. Find out how deferred maintenance reduces retention and the associated costs.Why deferred maintenance is essential and increases the value of a property.Discover what investors should do after a typical investment cycle. Why Joseph likes investing when multifamily sentiment is driven by fear and uncertainty.Unpack Trump’s Fed pick and how policy direction could impact real estate investing.Overview of the current financing landscape and how it is expected to change.Gary shares highlights from the recent NMHC Annual Conference in Vegas.Explore how lender behavior has shifted and why buying now could pay off in the long term.Joseph shares his opinion about the future of real estate and why he has a positive outlook.Links Mentioned in Today’s Episode:Joseph Fang on LinkedInNational Multifamily Housing Council (NMHC)Asset Management Mastery Facebook Group Invest SmartBreak of Day Capital Break of Day Capital InstagramBreak of Day Capital YouTubeGary 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.