Real Estate Investor Podcast

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

December 19, 2025 22 mins

With AI transforming nearly every industry, today’s guest is helping property investors supercharge their front-end sales funnels through intelligent chatbot systems. Kevin Brenner, Founder of PropertyBots™, is a true trailblazer at the intersection of real estate and artificial intelligence, bringing cutting-edge tech solutions to the investment world. In this episode, Gary and Kevin explore the future of AI in business, how Kevin...

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Welcome to the 250th episode of the Real Estate Investor Podcast! Today, Gary is joined by Joe Fang and Andy Huang to discuss the lessons we’ve learned throughout this experience. Tuning in, you’ll hear all about the history of the show, our favorite episodes, what we’ve experienced this year, and so much more! We delve into our outlook for 2026 before touching on what we expect the market will do. Finally, we talk about what it lo...

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Behind every successful property turnaround is a set of choices that shape the outcome. In this solo episode of the Real Estate Investor Podcast, Gary Lipsky walks listeners through a detailed case study of Icon on Spanish Trail, the 256-unit Tucson property he acquired in December 2023. He explains why the deal stood out (an institutional-quality asset purchased at a discount during a period of low transaction volume) and how his ...

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Joining Gary on the show today is Break of Day Capital's Director of Asset Management, Tim Chui. With over a decade of experience in institutional real estate, Tim Chui has held senior roles at leading firms including JRK Properties, Essex Property Trust, and American Realty Advisors. He began his career analyzing equity and fixed income opportunities before moving into acquisitions, portfolio management, and asset management....

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Today on the podcast, Gary sits down with Joe Rinderknecht, founder of Upgrade Partners Capital, a fund of funds, and Cowboy Capital, a real estate investment firm specializing in value-add multifamily properties. With nearly a decade of experience in commercial real estate, Joe has owned and invested in roughly 600 apartment units across Montana, Idaho, Utah, Texas, and Ohio. His background spans property and construction manageme...

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So much investing advice sounds convincing until the market shifts and the assumptions break. In this episode of the Real Estate Investor Podcast, we sit down with Chad Ackerman to unpack common myths that trap limited partners (LPs) and explore how to replace them with a disciplined, strategy-first approach to passive real estate investing. Chad is the founder of CARE, a coaching practice helping busy professionals unlock the pote...

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What do poker strategy and mobile home investing have in common? More than you might think! In this episode of the Real Estate Investor Podcast, we sit down with Pasha Esfandiary to dig into the secret behind his success in real estate and how he is shaking up the mobile home space. Pasha is the CEO and Managing Partner of Evoke Capital, a real estate investment firm specializing in high-upside mobile home communities. After a succ...

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What does it take to steer a multi-million-dollar property through one of the toughest lending environments in decades? In this episode of the Real Estate Investor Podcast, we welcome longtime friend and investor Gody Khambatta. Gody is a research scientist working on cancer treatments, but for over 25 years, he has also been quietly building a substantial real estate portfolio. In our conversation, Gody shares how he grew from hou...

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1031 exchanges are incredibly valuable for investors and are often underutilized and ignored. Today on the Real Estate Investor Podcast, co-founder and CEO of 1031 Specialists, Jon Hilley, joins us to share a play-by-play of 1031 deals. Tuning in, you’ll hear all about Jon’s career and what his company does, the structure of a 1031 deal, a definition of a few 1031 terms, and so much more! We delve into Jon’s thoughts on Delaware St...

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What happens when a former engineer and Shark Tank entrepreneur applies a product developer’s mindset to real estate? Alvin Uy has been focused on real estate in Los Angeles for 22 years, doing construction, fix-and-flips, short-term rentals, ADUs, SB9, and most recently, senior living. In this episode, Alvin shares how he built wealth by treating real estate like a product, creating solutions that attract tenants instead of chasin...

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What does it mean to operate at peak performance, and how can entrepreneurs and real estate investors learn from this principle that athletes adopt? From the NFL field to real estate and beyond, today’s guest, Larry English, knows what it takes to perform at the highest level. In this episode, Larry shares his journey from retiring from football to building success in real estate and founding MindBody Mastery, a program dedicated t...

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The commercial real estate market is shifting quickly, and in order to keep up and ensure you can finance your investments, you need to be able to adapt. In this episode of the Real Estate Investor Podcast, Anton Mattli from Peak Financing joins us to share his insights on today’s market trends and what lending is like in commercial real estate today. Tuning in, you’ll hear all about why lenders are tightening their scrutiny on loa...

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There are always investment opportunities; you just have to be patient enough to look for them! Today, we welcome the founder of the passive real estate investment educational platform, CARE, Chad Ackerman, to the show to discuss everything you need to know about investor syndication! Tuning in, you’ll hear all about Chad’s career and how investing led him to leave his corporate job, some big limited partner mistakes to avoid, and ...

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Today, we take a look at what happens when you narrow your focus to a single area, choosing to go a mile deep. We’re joined by Daniel Casey, President and CEO of North40 Capital, a local property developer, and BlackRock Construction Group, a commercial general contractor specializing in multifamily, senior living, and income-producing products. To start, Daniel introduces himself and the companies he runs before explaining how his...

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Once you truly understand what a wealthy life means to you, you can go out and take action to build that life, and you’re much more in control of your whole life than you may think! Today, we’re joined by Sahil Bloom, Managing Partner of SRB Ventures, writer of the Curiosity Chronicle, and bestselling author of The Five Types of Wealth: A Transformative Guide to Design Your Life, to explore how we can live more holistically wealthy...

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With rising debt, shifting prices, and mounting investor uncertainty, what’s really going on in the US economy? In this episode, real estate expert Kathy Fettke joins us to break down key trends shaping the housing and rental markets today. From the rise in multi-family loan delinquency to the surprising stability in home defaults, Kathy explains what these signals mean for investors. We also explore the impact of the potential Big...

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The dust has barely settled on the Invest Smart Summit 2025, curated by Break of Day Capital, and today, fellow colleagues Andy Huang and Joe Fang join Gary to unpack everything that happened in our third major summit (after the first two focused on real estate and asset management). Andy begins the conversation by explaining why he was more excited about his own panel than others before Joe shares some love for Gary and Ryan Kenne...

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Many first-time investors assume they need a 20% down payment to get started, but that’s not the case! Joining us to break it all down is Joseph Shalaby, founder and CEO of E Mortgage Capital, a national brokerage supporting nearly 900 loan officers across 48 states. He sits down with host Gary Lipsky to discuss the business model behind EMC’s success, key mortgage lessons for investors and loan officers, and financing options that...

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May 16, 2025 6 mins

Too many high earners look successful on paper but still feel stuck when it comes to building lasting wealth. In this special episode, host Gary Lipsky steps into the guest seat as his daughter, Arielle Lipsky, takes the mic to interview him about the upcoming Invest Smart Summit. Designed for busy professionals, this free virtual event brings together top minds in real estate, business, and personal development, including Sahil Bl...

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AI is rapidly becoming an essential tool across industries, but for real estate and asset management, it’s no longer optional. In his fourth appearance on the podcast, Neal Bawa returns to deliver a powerful masterclass on AI in real estate. Neal is the CEO and Founder/Cofounder of Grocapitus, Multifamily University, and Mission10K. Known as “the Mad Scientist of Multifamily,” his insights have helped him build an asset portfolio n...


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