Real Estate Investor Podcast

Gary Lipsky
  • 5.0 (19)
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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. 

  1. 7H AGO

    Episode #248 - Asset Management Mastery with Tim Chui

    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. Tim has overseen 54 multifamily assets across Southern California totaling more than 12,000 units and $5 billion in value, and has successfully navigated complex, over-leveraged portfolios through challenging market cycles. In today’s conversation, Tim shares what first drew him to the asset management space, the path that led him to his current role, and the skill set needed to excel in the field. He opens up about the toughest property he’s ever managed, the lessons learned, and his proudest accomplishments to date. They also dive into the tools and metrics that drive effective asset management, the industry’s evolving landscape, and where Tim believes the future of asset management is headed. Thanks for tuning in! Key Points From This Episode: Introduction to today’s guest and topic of conversation.What first grabbed Tim’s interest in the asset management space.The path to becoming an asset manager.Tim breaks down the basic skillset required in asset management. He shares about the hardest property he’s ever had to asset manage.What he learned from his most challenging property.His biggest accomplishment so far, in the asset management space.Tim sheds light on some of the biggest challenges he faces. Asset management tools and resources Tim can’t live without. A typical day as an asset manager; from Tim’s perspective. What he hopes to achieve when visiting properties on a monthly basis.Key metrics he focuses on.Tim shares his thoughts on the changes he’s witness and where the industry is heading.  Links Mentioned in Today’s Episode: Tim Chui on LinkedIn EliseAI Asset Management Mastery Facebook Group Invest Smart Break of Day Capital Break of Day Capital Instagram Break of Day Capital YouTube Gary 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.

    17 min

  2. OCT 31

    Episode #247 - Joe Rinderknecht — The Work Behind Operational Success

    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 management, asset management for large portfolios, and capital raising for a range of projects. In this conversation, Joe shares his approach to overcoming analysis paralysis through actionable steps like 10-minute napkin underwriting, dives into his strategies for investment and market selection, tells us how he honed his skills in asset management, and shares why understanding every part of the process matters. He also opens up about Tiny’s Tribe, the nonprofit he founded in memory of his brother and grandmother. Tune in for an inspiring and insightful discussion packed with practical advice, personal stories, and lessons on taking action even when fear stands in the way. Key Points From This Episode: We’re introduced to today’s guest, Joe Rinderknecht.Joe shares his real estate journey and how he got into commercial real estate.He recounts his first encounter with LIHTC section 42. Joe’s advice on overcoming analysis paralysis.His strategy for potential investment properties and market selection.How Joe got into and learned the ropes of asset management. He sheds light on Tiny’s Tribe nonprofit work.How to get in contact with Joe.  Links Mentioned in Today’s Episode: Joe Rinderknecht on LinkedIn Joe Rinderknecht on Instagram Joe Rinderknecht on Email Cowboy Capital Tiny’s Tribe on Facebook Obsidian Capital Levi Allen on LinkedIn Asset Management Mastery Facebook Group Invest Smart Break of Day Capital Break of Day Capital Instagram Break of Day Capital YouTube Gary 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.

    31 min

  3. OCT 24

    Episode #246 - Chad Ackerman - 7 Myths of Passive Investing

    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 potential of passive real estate investing without becoming landlords or leaving their careers. After co-founding Left Field Investors (now PassivePockets) and learning through both wins and mistakes, he now coaches others on how to define their investor identity, vet deals, and take confident, informed action. In this conversation, you will hear a practical walkthrough of the seven core myths of passive investing and hear advice for newer investors on distributions, accreditation, advisor incentives, and more. He also explains why emotions derail even seasoned investors, shares real-world lessons from his own portfolio, and offers practical tips to set clear goals, navigate deals with confidence, and take action without fear. Tune in now! Key Points From This Episode: Find out why education beats the analysis paralysis.Hear why defining your goals and developing a strategy is essential. Tips for creating an investor identity sheet and how it can help.Explore why past sponsors should always be re-vetted. Discover why big projected returns are not a guarantee of a good deal. Private Placement Memorandum (PPM) and why it is important.Unpack what people get wrong regarding investment distributions.Why you should always do your own research and not rely on others.Important aspects of diversification and why it needs to be intentional.Uncover common myths about investing and learn the value of community. Links Mentioned in Today’s Episode: Chad Ackerman Real Estate CARE Coaching Services Chad Ackerman on LinkedIn Tribevest PassivePockets Asset Management Mastery Facebook Group Invest Smart Break of Day Capital Break of Day Capital Instagram Break of Day Capital YouTube Gary 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.

    28 min

  4. OCT 10

    Episode #245 - From Poker to Mobile Home Communities with Pasha Esfandiary

    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 successful career as a professional poker player, Pasha transitioned into real estate, flipping more than 50 homes in Las Vegas before expanding into multifamily and development projects. Guided by his resilience, emotional intelligence, and a long-term vision, he has built Evoke Capital around creating win-win opportunities for both investors and residents. In our conversation, Pasha explains how skills honed at the poker table, such as long-term thinking, risk mitigation, and disciplined decision-making, have guided his success in real estate. He also shares why he prefers mobile home communities, what operational levers he pulls to maximize performance, and the investing philosophy that continues to shape his approach today. Join us to discover how you can turn an overlooked real estate niche into long-term wealth with Pasha Esfandiary! Key Points From This Episode: Hear about Pasha’s journey from professional poker player to real estate investor.What skills from his time as a poker player have helped him be successful in real estate.Learn about his approach to investing and why he focuses on long-term holds.Find out why his focus is on mobile homes instead of conventional real estate investments.The average length of a mobile home tenant and the operational costs of mobile communities. Discover what Evoke’s typical buy box is and why the company avoids vacant lots.Explore why being overly optimistic is the biggest downfall of real estate investors.Hear what most real estate investors get wrong and the cyclical nature of real estate.Pasha shares the two qualities that every real estate investor needs to be successful. Links Mentioned in Today’s Episode: Pasha Esfandiary Pasha Esfandiary on LinkedIn Pasha Esfandiary on Instagram Evoke Capital Raising the Stakes Think and Grow Rich Asset Management Mastery Facebook Group Invest Smart Break of Day Capital Break of Day Capital Instagram Break of Day Capital YouTube Gary 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.

    19 min

  5. SEP 26

    Episode #244 - Gody Khambatta – Riding the Refinance Rollercoaster to Success

    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 house hacking in San Diego to managing more than 400 units across Texas, and talks about his recent battle to recapitalize a 240-unit portfolio. He also discusses the realities of navigating bridge debt, rising interest rates, property tax exemption programs, and the tough decisions that ultimately led to a successful refinance. Join us for insights into pragmatic strategies on debt, asset management, and staying resilient through market swings, with Gody Khambatta. Tune in now! Key Points From This Episode: Welcoming Gody Khambatta, his background, and why he started investing in real estate.Hear how Gody was able to build his real estate portfolio from one property. His experience with recapitalization and what to consider about a bridge loan. Gody outlines how tax exemption programs in Texas can add significant value.The difference between local property tax exemptions and roamer property tax exemptions.Politics and regulatory hurdles he faced when trying to leverage the tax exemptions.Find out how Gody was able to find financing even though the tax exemption route failed.Discover why matching debt structure with long-term business plans is crucial. Learn about fixed-rate financing and how it can reduce exposure to market volatility.  Links Mentioned in Today’s Episode: Gody Khambatta on LinkedIn Gody Khambatta Email            Asset Management Mastery Facebook Group Invest Smart Break of Day Capital Break of Day Capital Instagram Break of Day Capital YouTube Gary 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.

    27 min

  6. SEP 12

    Episode #243 - Jon Hilley – The 1031 Playbook

    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 Statutory trusts before he stresses the importance of hiring a qualified intermediary for 1031 exchanges. He even discusses the fee structures and reminds us why proper planning is key in these kinds of deals. Finally, our guest touches on some common mistakes he sees being made in 1031 exchanges. Thanks for listening in!  Key Points From This Episode: A warm welcome to today’s guest, Jon Hilley. What Jon and his company, 1031 Specialists, do.The structure of a 1031 deal and why it’s important. Jon explains basis, equity, and net investment goal. His thoughts on DSTs (Delaware Statutory Trusts). The importance of hiring a qualified intermediary. Jon explains his fee structures for 1031 deals. The importance of proper planning in 1031 exchanges. Common mistakes investors make in 1031 deals.  Links Mentioned in Today’s Episode: Jon Hilley on LinkedIn 1031 Specialists Call 1031 Specialists on 631-438-1031 National Association of REALTORS Asset Management Mastery Facebook Group Invest Smart Break of Day Capital Break of Day Capital Instagram Break of Day Capital YouTube Gary 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.

    23 min

  7. SEP 5

    Episode #242: Alvin Uy – Real Estate Product Developer

    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 chasing them. From maximizing returns through ADUs and rent-by-the-room strategies to developing co-living and senior housing models inspired by personal experience, Alvin reveals the creative approaches that have allowed him to thrive in one of the nation’s toughest markets. He also opens up about today’s challenges with capital raising and investor expectations, while offering an optimistic outlook on Los Angeles real estate as the city prepares for global events and a new wave of growth. Key Points From This Episode: Alvin Uy’s pursuit of real estate after seeing his immigrant parents lose everything.How Alvin transitioned from aerospace engineering and design into real estate by leveraging creativity and side hustles like flipping homes.What appearing on Shark Tank taught him: the value of betting on himself instead of selling out early.How viewing real estate as a product helped Alvin by shifting his focus from chasing deals to creating solutions people chase.Building ADUs in Los Angeles to force appreciation and cash flow.Boosting his returns by pivoting to rent-by-the-room models that maximized market rents and tenant turnover benefits.Partnering with a construction team that allows scalable, cost-efficient builds.Diversifying by experimenting with co-living models like student housing, assisted living, and sober living.Managing investor expectations and navigating market uncertainty with high-end flips. Links Mentioned in Today’s Episode: Alvin Uy on LinkedIn Alvin Uy on Instagram Alvin Uy on X AARK Investments Rich Dad, Poor Dad Asset Management Mastery Facebook Group Invest Smart Break of Day Capital Break of Day Capital Instagram Break of Day Capital YouTube Gary 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.

    29 min

  8. AUG 22

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

    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 to helping people unlock peak performance. He breaks down common misconceptions about high achievement, the critical role mindset plays, and more! Larry also reflects on what he wishes he knew about peak performance in his youth, offers advice for anyone stuck in a plateau, and reveals how anyone can reach new levels of growth and performance. You don’t want to miss this one, so be sure to tune in now! Key Points From This Episode: A brief overview of today’s guest, Larry English.What led him to retire from football and get into real estate.How he became a peak performer not only in football, but real estate too.What led Larry to start MindBody Mastery and what they do. Some misunderstandings about achieving peak performance. How mindset plays a role in the effectiveness of peak performance. Larry shares his favorite piece of equipment he uses every day. What he would tell his younger self about peak performance. Larry’s advice for anyone who has hit a plateau and feels stuck.  Links Mentioned in Today’s Episode: Larry English on LinkedIn Larry English on Instagram Larry English on X MindBody Mastery Asset Management Mastery Facebook Group Invest Smart Break of Day Capital Break of Day Capital Instagram Break of Day Capital YouTube Gary 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.

    30 min
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5
out of 5
19 Ratings

About

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. 

Information

  • Creator
    Gary Lipsky
  • Years Active
    2021 - 2025
  • Episodes
    247
  • Rating
    Clean
  • Copyright
    © 2025 Real Estate Investor Podcast
  • Show Website
    Real Estate Investor Podcast

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