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 #90: Critical Lending Environment Updates with Andrew Westling 28.01.2022

It’s critical to stay on top of the current lending environment. Joining us today to update us on everything we may have missed is Andrew Westling. Andrew is the Associate Director of Capital Markets at Walker & Dunlop and is well-versed in the world of lending, to say the very least! In this episode, we pick Andrew's brain and discover the effect that the shift from LIBOR to SOFR has had...

Episode #89: Backstage Guide to Real Estate with Matt Picheny 21.01.2022

Today's guest is the legendary Matt Picheny, real estate syndicator (including syndication for Broadway) and the author of Backstage Guide to Real Estate . Tuning in, year how Matt turned a potentially devastating situation into the success story of his first buy, how he made the switch to full-time real estate investing, and the huge amount of learnable advice and hard-won experience that is...

Episode #88: Repositioning Rent Controlled Assets with Quentin D’Souza 14.01.2022

In this episode of the Real Estate Asset Management Podcast, we are joined by Quentin D’Souza, a schoolteacher turned prolific real estate investor. Quentin has over 80 million dollars in assets under management across Canada and the US has transacted over 80 properties since 2004 and is the author of four real estate books. In our conversation with Quentin, he sheds light on the differences betwe...

Episode #87: Vertical Integration to Overcome Obstacles with Steven Ludwig 07.01.2022

In today's climate of supply chain issues and labor cost hikes, being vertically integrated is a one-way ticket to being successful in a time that can be devastating to smaller businesses. Today on the show we have real estate powerhouse Steven Ludwig, who's vertically integrated and has purchased over 1.2 billion dollars worth of real estate in Southern California. In this conversation,...

Episode #86: Asset Management Tips and Tricks with Ryan Christopher Nunes (Rerun) 24.12.2021

On today’s episode, we host Ryan Christopher Nunes, president and founder of Life Changing Capital. He shares three macro tips he has learned during his successful career on Wall Street to help listeners up their asset management game. You’ll also hear about his background before entering the world of multifamily asset management and how he met his partner with whom he has since underwritten 300 d...

Episode #85: Asset Disposition the Right Way with Gene Trowbridge 17.12.2021

Today on the Real Estate Asset Management Podcast we are joined by former syndicator turned lawyer, Gene Trowbridge, to talk about voting rights, 1031s, and closing an entity. Gene shares his journey of moving from commercial real estate to syndication, and finally to law at the age of 45. Despite his predictions of retiring from law after 15 years, he’s still deep in it 27 years later and, along...

Episode #84: Investment Strategy with Juan Vargas 10.12.2021

Thanks for tuning in to another episode of the Real Estate Asset Management Podcast! Today we welcome Juan Vargas, a multi-family investor with over five years of experience under his belt. During our conversation, we ask him about the most important factors he looks for in an investment opportunity, why he is moving his focus to A and B products instead of C, and what his rule of thumb is when it...

Episode #83: Sell or Refi: The Multimillion-Dollar Question with Omar Khan 03.12.2021

Welcome to the Real Estate Asset Management Podcast brought to you by Break of Day Capital! In today’s episode, we talk to Boardwalk Wealth syndicator, Omar Khan, about the multimillion-dollar question: sell or refi? Omar shares his thoughts on whether he thinks it’s best to recapitalize, sell, or refinance properties and shares examples from his own career experience. We discuss the pros and cons...

Episode #82: Business Plan Execution with Tyler Chesser 26.11.2021

Welcome back to the Real Estate Asset Management Podcast. Thanks for joining us! In conversation with us today is Tyler Chesser, who hosts the Elevate podcast, which is all about mindset, mind expansion, and personal development for high-performing real estate investors. Our topic today is big picture investment strategy, and Tyler Chesser shares some amazing pearls of wisdom with us, all underpin...

Episode #81: Managing Risk with Dustin Miles and Hayden Harrington 19.11.2021

Today on the Real Estate Asset Management Podcast, we talk to Dustin Miles and Hayden Harrington of Momentum Multifamily about managing risk in the asset management sphere. We discuss the differences when it comes to managing a C-class versus an A-class or a B-class deal, as well the pros and cons of each class respectively. Dustin and Hayden share the ways in which COVID has affected their choice...

Episode #80: Going Full Cycle with Gary Lipsky 12.11.2021

Welcome back to another episode of the Real Estate Asset Management podcast! The conversation today centers around a recent deal we sold, covering the whole cycle of ups and downs we faced along the way! We kickstart the conversation with some numbers up front and move through each step from the initial site inspection of this true value-add to the challenges. We talk about taking over just a few...

Episode #79: Real Estate Tax Changes with Brandon Hall 05.11.2021

With each change in administration, come new changes to the U.S. tax bill. This week’s guest on the Real Estate Asset Management Podcast is Brandon Hall, CPA and managing partner of The Real Estate CPA. In our conversation with Brandon, he breaks down some of the tax changes that have been implemented by the Biden administration thus far, what we can anticipate in the coming years, and how the cha...

Episode #78: Stepping Outside Your Comfort Zone with Chris Bystriansky 29.10.2021

Mindset, preparation, and mentorship aren’t necessarily the first words that come to mind when referring to asset management and multifamily real estate. Today’s guest, multifamily real estate investor and author, Chris Bystriansky, is here to prove otherwise. In today’s episode, Chris shares a bit about his professional background and how changing his mindset changed his life. He speaks about the...

Episode #77: Building a Business with Gino Barbaro 22.10.2021

Today’s guest went from running a family-owned pizzeria to being one of the top mentors in multifamily investing. Join us as Gino Barbaro takes us through his 10-minute MBA, and gives us key advice on how to build your business. From defining your core values, to how to structure your business goals and meetings, this episode is a masterclass! Find out how to make your first hire less daunting, an...

Episode #76: Interior Decorating to Boost NOI with Lisa Landry 15.10.2021

As a multifamily syndicator, your return on investment does not solely rely on your ability to increase rents. There are numerous ways that you can boost your NOI and, in this episode, we cover how interior design can help you do just that! Today’s guest is Lisa Landry, President of Landry Designs and Landry Staging and CEO of Above & Beyond Holdings, a multifamily investment company with over...

Episode #75: Underwrite Like A Pro with Rob Beardsley 08.10.2021

Hello and welcome back to the Real Estate Asset Management Podcast! Today we talk all things underwriting, with co-founder and principal of Lone Star Capital, Rob Beardsley. In this episode, Beardsley shares some of his vast knowledge on all the components that make up the underwriting process, and guides us through the ins and outs of using the analytical tools at your disposal to create a solid...

Episode #74: Getting Deals Done with Gary Lipsky 01.10.2021

Thank you for joining us for another episode of the Real Estate Asset Management Podcast! During today’s conversation, Gary Lipsky shares all the details of a deal he closed in early 2021. You’ll hear how, when you focus on a few markets, you can become an expert in those markets, what it was like to close a deal within the seller’s tough time constraints, and how a zoning attorney can be useful....

Episode #73: Multifamily Outlook with Andrew Rybczynski 24.09.2021

Welcome back to another episode of the Real Estate Asset Management Podcast, today’s guest is Andrew Rybczynski. Andrew is a management consultant at CoStar Advisory Services, which is built on top of CoStar, the largest data provider for commercial real estate in the US. They utilize the data to advise institutional clients, banks, pension funds, REITs, hedge funds on investment and commercial re...

Episode #72: DST to Unlock Capital for Deals with Brett Swarts 17.09.2021

Today we welcome Brett Swarts to the show, the founder of Capital Gains Tax Solutions. Brett is also a commercial real estate broker, multi-family expert, and he and his company strive to help people who feel trapped by capital gains tax when selling highly appreciated apartment buildings. They like to refer to themselves as the Netflix way of deferred taxes! Joining in today, listeners will hear...

Episode #71: Protesting Property Taxes with Darin Batchelder 10.09.2021

If you’re not protesting property taxes, you’re more than likely missing out on savings you can earn! Today we welcome a good friend, Darin Batchelder, a successful businessman and real estate syndicator. Darin is a man with a great skill set, especially with regards to building relationships and setting expectations, particularly with people in the real estate world where the 'know, like, an...

Episode #70: Asset Management Tips and Tricks with Ryan Christopher Nunes 03.09.2021

On today’s episode, we host Ryan Christopher Nunes, president and founder of Life Changing Capital. He shares three macro tips he has learned during his successful career on Wall Street to help listeners up their asset management game. You’ll also hear about his background before entering the world of multifamily asset management and how he met his partner with whom he has since underwritten 300 d...

Episode #69: Adaptive Reuse with Gary Lipsky 27.08.2021

The idea of adaptive reuse has been gaining more and more traction in the last year and shows no signs of slowing down. We particularly believe in the value of getting familiar with the adaptation of office space to multifamily and to help introduce our listeners to its potential benefits, in this episode Gary breaks down a recent example of this model, and a particular property in Youngtown, Ariz...

Episode #68: Jumping in with a Development Deal with Dallon Schultz 20.08.2021

In today’s episode of the Asset Management Mastery Podcast, we speak with Dallon Schultz, Cofounder and Managing Partner in Empire Assets, about the value of jumping into development deals, learning by doing, and leveraging the experience of others. Dallon specializes in investor relations, market research, and analyzing properties. He is also a licensed Realtor in the state of Arizona and is cont...

Episode #67: Raise More, Save Time With a Portal 16.07.2021

Today’s guest, Perry Zheng, founder of Cash Flow Portal, a real estate syndication software, tells us about his own journey with real estate investment, and how he came to develop a tool to raise money, and resolve some of his own pain points. Perry kickstarts our conversation by telling us a bit about his background, working in software engineering and management at Silicon Valley. Next, he tells...

Episode #66: Boost Credibility with a Pro Website 09.07.2021

Websites are a key piece in establishing credibility. It is not just enough to have an online presence though; your website should reflect who you are professionally. Todd Heitner’s company, Apartment Investor Pro, helps GPs create fantastic websites, leaving them more time to focus on things like deal sourcing and fundraising. In today’s episode, Todd walks us through the importance of a website,...

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