Gary Lipsky

Real Estate Investor Podcast

Business EN ↓ 265 episodes

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. 

Author

Gary Lipsky

Category

Business

Podcast website

www.breakofdaycapital.com

Latest episode

Jul 3, 2026

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Episodes

Episode #190: Investor Engagement with K. Trevor Thompson 22.03.2024

Networking is more than just a few handshakes and pockets full of business cards; it’s about creating lasting, mutually beneficial relationships. For today’s impactful episode, we are in conversation with the VP of Investor Engagement at Massive Capital, K. Trevor Thompson to discuss some best practices for working with investors. Trevor has almost half a century of experience in entertainment and...

Episode #189: Michael Scherer – Creating Change in Detroit 15.03.2024

In this episode, we sit down with Michael Scherer, founder of Atlante Capital Group, to discuss the importance of affordable housing and community development in Detroit. The mission of Atlante Capital Group is to acquire, renovate, and lease clean, safe, and accessible housing solutions for individuals facing significant housing challenges. With over three decades of operational expertise spannin...

Episode #188: Todd Dexheimer – Scaling from $20k to $500M 08.03.2024

Jumping between asset classes can be tricky if you don’t know what you’re doing, but it can also give you the foundational knowledge to go on and scale at will! Todd Dexheimer is the Co-Founder and Principal of Endurus Capital as well as the Principal of VitaCare Living, and he joins us today to share his methods for scaling from $20,000 to $500 million. We learn about how Todd got into real estat...

Episode #187: Brian Boyd – Real Estate Tax Tips 01.03.2024

What if there was a loophole in the tax code that you could use to not only earn more from your real estate investments but also pay less tax? Well, you need look no further, as Brian Boyd joins us today to share some incredible real estate tax tips! Tuning in, you’ll hear all about our incredible guest’s career as a lawyer, what got him interested in real estate, how he got started, exactly how t...

Episode #186: Adam Dresher - From Wall Street to Real Estate 23.02.2024

In this episode, we delve into the intriguing journey of Adam Dresher, a former Wall Street expert who made a successful transition into the dynamic realm of real estate investing. Adam is a seasoned professional with a diverse background spanning over two decades in the financial services industry. Currently, Adam channels his expertise in real estate and plays a pivotal role in assisting clients...

Episode #185: Neal Bawa – Less Distress 16.02.2024

There is so much talk of distress in the real estate world so today on the Real Estate Investor Podcast, we are getting an incredible breakdown of it from Neal Bawa. Tuning in, you’ll hear all about Neal’s career, how you can ‘do the math’ for multi-family properties in distress, a breakdown of distress and debunking of myths, and more! Our guest reminds us that bad investments are inevitable befo...

Episode #184: Tom Zeeb – Getting Started in Real Estate Investing 09.02.2024

Are you eager to get into real estate, but need help figuring out where to start? Then you won’t want to miss today’s conversation with best-selling author, speaker, real estate entrepreneur, and President of Traction Real Estate Investors Association, Tom Zeeb. His podcast, The Art & Science of Real Estate Negotiation is an indispensable resource for anyone looking to get into real estate, an...

Episode #183: Peter Linneman – Interest Rates, the Economy and Multifamily 02.02.2024

Today we are joined, once again, by esteemed guest and friend of the show, Peter Linneman, to discuss his take on interest rates, the economy, and multifamily. In addition to being the Founding Principal of Linneman Associates, Peter is also a former Wharton professor, distinguished author, and co-creator of the highly regarded Real Estate Finance and Investment Certification Course by REFAI. We l...

Episode #182: Being Diligent with Joseph Fang 26.01.2024

Joseph Fang is the Director of Investor Relations at Break of Day Capital and he revisits the podcasts to share his insider’s perspective, reflections, and projections from 2023 going into 2024. Kicking things off, we share the details and challenges of closing on Icon on Spanish Trail in December 2023 and explore what is behind the lack of investor liquidity in today’s landscape. We then discuss...

Episode #181: DJ McClure – Flood Zones 19.01.2024

Buying property in flood zones is a daunting prospect for many investors, with high insurance premiums being the main deterrent. But there are ways to reduce insurance costs for flood zone investors, it’s all about doing your due diligence and understanding the options that are available to you. Walking us through the ins and outs of flood zone insurance is the VP of Business Development at Nation...

Episode #180: Anthony Vigilante – Investing as a Busy Professional 12.01.2024

Do you want to get into real estate investing but are worried that you don’t have enough time to juggle your job, family, personal life, and investing? Then this episode of the Real Estate Investor Podcast is for you! Today we are joined by the incredible Anthony Vigilante to discuss investing as a busy professional. Anthony is a seasoned CTO, experienced real estate investor, and investor coach,...

Episode #179: Mauricio Rauld – 6 Layers of Asset Protection 15.12.2023

Asset owners often feel that having insurance on their properties is enough to protect them from any liability but that is simply not the case! Today we are joined by Real Estate Syndication Attorney, Mauricio Rauld to discuss the six layers of asset protection he has created for his clients. Tuning in, you’ll hear about Mauricio’s career, why he believes having more than one layer of asset protec...

Episode #178: Building a Great Team with Brandon Turner 08.12.2023

Today’s guest has done a remarkable job of growing his company in a very short amount of time and joins us to shed light on how he successfully managed to do this. Brandon Turner is the founder and managing member of Open Door Capital. He is also a best-selling real estate author and a past host of the BiggerPockets podcast with over 100 million downloads. Brandon has a strong track record of inve...

Episode #177: Andrew Westling – Current Lending Environment 01.12.2023

As an investor, it’s easy to get overwhelmed with the wealth of information that you’re required to sift through to make a good financial decision. It’s always wise to employ the services of a good broker, and Andrew Westling is here to explain why his firm is one of the best in the business!  Andrew is a Director of Capital Markets at Walker & Dunlop, one of the largest commercial real estate...

Episode #176: Gary Lipsky – Bullish or Bearish 24.11.2023

Striking a balance between a bullish and bearish attitude toward the real estate market is a skill that is imperative for success in multifamily real estate. In this episode of the Real Estate Investor Podcast, we are discussing the future of the market and our conversation on the multifamily panel at the recent MFIN conference. Tuning in, you’ll hear about the unknowns in the market, what our pla...

Episode #175: Epic Grit with Clay Speakman 10.11.2023

Grit is a personality trait or quality beyond talent or intelligence. It is about having the determination and resilience to overcome obstacles and stay committed to a task or objective. In this episode, we take a unique turn as we dive into the world of epic grit with special guest Clay Speakman. Clay, a distinguished entrepreneur who has navigated the complexities of building technology companie...

Episode #174: Dave Foster – 1031 Exchange 03.11.2023

A 1031 exchange provides the opportunity of deferring taxes by swapping one investment property for another. However, the nuances of 1031s can be tricky to understand, so we’ve asked Mr. 1031 himself, Dave Foster, to join us and help explain the basics of a 1031 exchange. We discuss why the time constraints of 1031s are unattractive to investors, some solutions for deferring tax and maximizing a 1...

Episode #173: Peter Eberhardt – The Athlete Mindset 27.10.2023

Competitive sports require a certain tenacity, discipline, and focus to succeed, and it’s one of the best teachers for embracing failure. Joining us today is BMX rider-turned real estate investor, Peter Eberhardt, and he explains how he was able to buy his first property at the tender age of 21. Then, we dive into the rest of his real estate journey as he shares the lessons he’s learned by being h...

Episode #172: Joseph Fang – Fear & Macro 20.10.2023

Every investment is accompanied by some element of risk. Seasoned investors know this, but for many, there is still a lot of fear around economic instability, market volatility, and more. Today, Joseph Fang, Director of Investor Relations here at Break of Day Capital, returns to the show to share his big-picture take on the current macro environment, the perks of being a contrarian, the dangers of...

Episode #171: Alan Underwood - An Entrepreneur's Journey into Real Estate 13.10.2023

The entrepreneurial path is rarely a straight line, and it is often only upon reflection that you uncover the throughline beneath all the challenges and obstacles that you experienced along the way. Joining us today is Alan Underwood, a dynamic entrepreneur whose adventures range from launching a pizza chain at the tender age of 22 to navigating the stresses of managing a car dealership amidst the...

Episode #170: Christina Suter – Grit and Education 06.10.2023

Just like anything else in life, real estate investing is filled with ups, downs, and many twists and turns. However, the real problem is when times of financial tribulation fill you with dread and feelings of inadequacy. But if you can push through those feelings and persevere through moments of doubt and financial downturns, then what awaits on the other side is a life of true financial freedom....

Episode #169: Colm McEvilly – Investor Decision-Making Process 22.09.2023

When it comes to investing in real estate, the decision-making process is of unparalleled importance. This is where you, as the investor, will ascertain whether to get involved in a project or look elsewhere for more viable options. To help us make sense of the decision-making process for investors, we are joined by real estate sponsor and developer, and our dear friend, Colm McEvilly. After comin...

Episode #168: Ryan Kennedy — Health is Wealth 15.09.2023

Welcome to this special edition of the Real Estate Investor Podcast, where we bring you everything that happened in our recent Health is Wealth webinar with Ryan Kennedy. Ryan is a functional medicine practitioner, traditional naturopath, and board-certified clinical nutritionist who helps people improve their health through lifestyle and dietary changes. In Health is Wealth, Ryan breaks down ever...

Episode #167: Corey Peterson – What Could Possibly Go Wrong from LOI to Close? 08.09.2023

Most real estate investors relax once the LOI period is over but that is a huge mistake! Loads of things can go wrong between LOI and the close of the deal, and joining us today is Corey Peterson to tell us all about possible bumps in the road. Tuning in, you’ll hear all about our guest’s remarkable career, why Corey works with an attorney in certain instances, his personal LOI timeline, why you n...

Episode #166: Jordan Berry — Investing in Laundromats 01.09.2023

Laundromats may have the stigma of being boring, tiresome places where no one truly wants to be, but they should not be dismissed by willing investors outright, because buying into a laundromat may bring you faster returns than most real estate ventures. We are thrilled to be joined today by Jordan Berry, the Founder of Laundromat Resource, an education and community platform dedicated to current...

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