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 #241: Larry English – Former NFL Player Talks Peak Performance 22.08.2025

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 Mind...

Episode #240: Anton Mattli – Financing in a Tight Market 15.08.2025

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 a...

Episode #239: Chad Ackerman – Investor Syndication Need to Knows 18.07.2025

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 limi...

Episode #238: A Mile Deep – Daniel Casey 11.07.2025

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 companie...

Episode #237: Sahil Bloom: The 5 Types of Wealth 04.07.2025

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...

Episode #236: Kathy Fettke – Navigating the Economic Landscape and Rental Market Trends 20.06.2025

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 expl...

Episode #235: Invest Smart Takeaways & Behind the Scenes with Joe Fang and Andy Huang 13.06.2025

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 share...

Episode #233: Joseph Shalaby: Running A Mortgage Company 23.05.2025

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 o...

Episode #232: Invest Smarter 16.05.2025

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 perso...

Episode #231: Neal Bawa: AI Masterclass for Real Estate 02.05.2025

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 he...

Episode #230: Ben Reinberg – Hard Assets for Hard Times 25.04.2025

Hard assets are time-proven as one of the best ways to build sustaining wealth. Joining us today is Ben Reinberg, the CEO of Alliance Consolidated Group of Companies and author of Hard Assets and Hard Money for Hard Times . We begin with Ben’s background and journey into real estate before diving into what he thinks about the current state of the real estate market. Then, we discover the dangers o...

Episode #229: Aleksey Chernobelskiy: What to Know as a Limited Partner 11.04.2025

What does it mean to vet a real estate deal as a limited partner? In this episode of The Real Estate Investor Podcast, host Gary Lipsky welcomes Aleksey Chernobelskiy, Principal at Centrio Capital Partners and Founder of GP-LP Match. Aleksey previously ran Store Capital’s lucrative real estate portfolio and underwriting team before shifting his focus to educating and advocating for limited partner...

Episode #228: Kevin Bupp: MHP's and Parking Lots 04.04.2025

Open land rarely garners the same attention as developed properties due to their perceived value discrepancies. But as today’s guest, Kevin Bupp explains, there are many ways to generate significant income from open spaces like mobile home parks and parking lots. Kevin is a seasoned commercial real estate investor, a top podcast host, and author of The Cash Flow Investor, a practical step-by-step...

Episode #227: Joe Fang: Navigating Uncertain Times 21.03.2025

Uncertainty in the real estate market can create both risk and opportunity. Long-term success belongs to those who know how to navigate it wisely! In this episode, we welcome back investor, macroeconomics expert, and Director of Investor Relations at Break of Day Capital, Joseph Fang, to break down key market trends, interest rate predictions, and investment strategies that matter right now. Gary...

Episode #226: Passive Investing Master Class with Jeremy Roll 14.03.2025

Is now the right time to invest in real estate, or are we on the verge of a market downturn? In this episode of the Real Estate Investor Podcast, we sit down with seasoned investor Jeremy Roll to unpack the state of real estate investing in today's economic climate. Jeremy began investing in 2002 and left the corporate world in 2007 to pursue financial freedom through passive income. He now m...

Episode #225: Advanced Class on Asset Management with Mike Taravella 28.02.2025

What separates top-performing real estate investors from those who struggle? In this episode, we sit down with Mike Taravella, an experienced real estate investor and asset manager with a background in accounting and corporate finance. Mike is the founder of Niche Holdings, where he manages millions of dollars in assets and provides third-party asset management consulting to optimize client portfo...

Episode #224: What You Must Know About the Economy and Real Estate Investing in 2025 14.02.2025

What’s going to be good and bad for the economy in the next year? Dr. Peter Linneman is a renowned real estate expert and economist with nearly 45 years of experience, and he joins us today to share his keen insights into the current and future state of the US economy. Combining academic excellence from Wharton and the University of Chicago with a successful business career as Founding Principal o...

Episode #223: Finding the Best Real Estate Locations with Austin Hair 07.02.2025

Joining Gary on the podcast today is Austin Hair. Austin is a real estate developer specializing in identifying prime locations that help clients scale quickly and provide investors with secure, compounding returns. With over a decade as a professional wakeboarder and a finalist on American Ninja Warrior , Austin combines discipline and calculated risk-taking to excel in real estate investment. He...

Episode #222: George McCleary – Overcoming Squatters and Title Fraud 31.01.2025

One of the great pains of being a homeowner is dealing with squatters and even worse, title fraud. Today, with the help of George McCleary, we learn how to protect ourselves against would-be squatters and how to be prepared when someone tries to rob you of your equity. George is the CEO of Defender Networks, a company dedicated to protecting their users from squatters, title fraud, and other real...

Episode #221: Hannah Hammond — Breaking Barriers and Rising to Success 24.01.2025

Hannah Hammond is a resilient entrepreneur who overcame a challenging childhood to build a remarkable career, founding and leading multiple successful companies across real estate, lending, construction, and property management. During this episode, she joins us to share her story and to offer insights on entrepreneurship, financial success and personal growth. From the book that started it all to...

Episode #220: Ruben Ortiz – Multifamily Capex Projects 10.01.2025

What makes a successful relationship between operators and general contractors? In today's episode, we speak with Ruben Ortiz, founder of Sayan Renovations & Construction. Based in Dallas, Ruben and his team tackle complex multifamily Capex projects with a focus on quality, innovation, and authenticity. In our conversation, Ruben shares his journey from working alongside his father in con...

Episode #219: Gary Lipsky- Closing Deals in Today's Environment 03.01.2025

Welcome back to a new year and another episode of The Real Estate Investor Podcast with your host, Gary Lipsky of Break of Day Capital. In this episode, Gary dives into today’s topic: finding and closing deals in the current market. He shares insights from their most recent deal, recaps the capital trends of 2024, and offers actionable tips to help you prepare for when deals come to market. Tune i...

Episode #218: Year End Tax Strategies with Brandon Hall 13.12.2024

Taxes don’t have to be daunting, especially when you know the strategies to make them work for you. In today’s episode, we welcome back Brandon Hall, a practicing CPA and the founder and managing partner of Hall CPA, to unpack powerful tax-saving strategies every investor should know. Brandon delves into key topics for year-end tax, like how to handle bonus depreciation and the best ways to naviga...

Episode #217: Multi-Family Marketing with BeSwifty CEO Jon Simpson 06.12.2024

Jon Simpson is passionate about helping multi-family investors turn leads into leases. Founder of Criterion. B and BeSwifty, Jon is a multifamily marketing expert with over 20 years of experience in digital solutions and AI-driven property marketing and he joins us in conversation to share key insights from his extensive experience. He has worked with top brands like AG Spanos Corporation and RPM...

Episode #216: Multifamily Market Update with J Scott 22.11.2024

What’s the current state of the multifamily real estate market, and how can investors navigate today’s economic challenges? In this episode, we welcome J Scott, a partner at Bar Down Investments and an acclaimed real estate investor. He’s also the author of five books published by BiggerPockets and co-host of the very popular Drunk Real Estate Podcast. In our conversation, J delves into the impact...

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