Real Estate Investor Podcast

Gary Lipsky
  • 5.0 (19)
  • INVESTING
  • UPDATED WEEKLY

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. JAN 30

    Episode #254 - Omar Khan - Navigating Legacy Properties with a Long View

    What does it take to protect your deals when the market turns? In this episode, we sit down with Omar Khan, founder of Boardwalk Wealth, to discuss the challenges currently facing the real estate industry. Omar explains the overall state of the market, the impact distressed assets have caused, and why transparent communication with investors during these times is vital. He unpacks the potential opportunities in acquiring distressed assets in the coming years, the value of consistent performance, and why creative problem-solving is essential during market turns. Omar breaks down how to navigate loan terms, the value of agency loans in the current market, the effect of rising interest rates on the market, and how to show investors they can trust you. We also delve into the challenges of raising capital, the impact of geopolitical factors on occupancy and collections, and the importance of effective asset management. Tune in to learn how disciplined operations, lender-savvy strategy, and clear investor communication can help you navigate downturns and position yourself for opportunities, with Omar Khan! Key Points From This Episode: Introduction to Omar and his company, Boardwalk Wealth.Hear why Omar regards the last few years as a broad “basis reset.”Learn how Omar approaches agency loans and why agency requirements matter.Discover why clear communication with investors is vital during a market turn.Find out why extending hold periods is sometimes the best outcome.Unpack his approach for finding distressed deals and opportunities.Why doing what you promise builds trust with brokers and lenders.Uncover how Boardwalk Wealth has navigated the market upheaval.His outlook for the market and why he thinks it will stabilize rather than improve.Explore why raising capital for multifamily investments has become challenging.Final takeaways and how to contact Omar. Links Mentioned in Today’s Episode: Omar Khan on LinkedIn Boardwalk Wealth Episode 83: Sell or Refi Family Office Club 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

  2. JAN 23

    Episode #253 - Kevin Kim — Creative Capital Structuring

    Today on the podcast, host Gary Lipsky welcomes Kevin Kim. Kevin leads Fortra Law’s corporate and securities practice, where he and his team have advised on and prepared hundreds of securities offerings, including mortgage funds, structured debt offerings, real estate syndications, crowdfunding offerings, EB-5 projects, and qualified opportunity funds. In this episode, Gary and Kevin explore how Kevin has helped clients navigate recent challenges in the multifamily space from a legal perspective, including a deep dive into one of the more complex deals Kevin has closed. Kevin also breaks down Employment-Based 5 (EB-5) visas and their best use cases in real estate, explains what an UPREIT is and the structuring involved, and outlines how non-UPREIT structures differ. They wrap up the conversation discussing Kevin’s thoughts on the evolution of the legal side of the real estate business and how listeners can learn more about Kevin and Fortra Law. Thanks for listening in.  Key Points From This Episode: Listeners are introduced to our guest, Kevin Kim.How they’ve helped clients navigate the multifamily struggle, from a legal perspective. Kevin talks through one of the more intricate deals he’s had to close recently. He unpacks Employment-Based-5 (EB-5) visas and their best use case in real estate.Kevin breaks down what UPREIT is and the structuring involved.He explains what a non-UPREIT situation would look like.How Kevin sees the legal side of the business will evolve: navigating nuances.Where you can learn more about Kevin and his company, Fortra Law.  Links Mentioned in Today’s Episode: Kevin Kim on LinkedIn  Kevin Kim on Email Kevin Kim, Esq Fortra Law Fortra Law on YouTube One, Big, Beautiful Bill provisions Regulation D  Regulation A 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.

    26 min

  3. JAN 9

    Episode #252 - Dallon Schultz – Capital Raising

    Returning to the podcast after four and a half years is Dallon Shultz. Now a seasoned fund manager, Dallon is also the co-founder of Capitallyst Pro, an automated CRM platform designed to help real estate investors raise capital more efficiently and effectively. In this episode, Dallon shares what inspired the creation of Capitallyst Pro, the company’s vision and mission, and his insights on the three most common mistakes capital raisers make. The conversation also explores how capital raising is likely to evolve in the coming years, why the power of association may be the biggest check writer of all, and the exciting updates ahead for Capitallyst Pro. Tune in now to hear it all. Key Points From This Episode: Introduction to today’s guest and topic.What inspired him to start Capitallyst Pro and their vision and mission.The three most common mistakes Dallon sees capital raisers make.His thoughts on how capital raising might evolve over the next few years.The power of association: the biggest check writer.What most influenced Dallon on capital raising. Dallon shares some exciting changes they’re implementing. Where to learn more about Dallon Shultz and Capitallyst Pro. Links Mentioned in Today’s Episode: Dallon Shultz on LinkedIn Capitallyst Pro Capitallyst Pro on YouTube Episode #68: Jumping in with a Development Deal with Dallon Schultz Best Ever Apartment Syndication Book Best Real Estate Investing Advice Ever, Volume 1  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. 12/19/2025

    Episode #251 - Kevin Brenner — AI for Real Estate Marketing

    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’s military experience shaped his path to entrepreneurship, and the journey that led him to master the world of AI. Kevin also breaks down the five essential elements of effective chatbot prompts, explains how AI can support raising capital, and shares how PropertyBots™ is leveraging these tools to drive meaningful results. To discover how AI is reshaping real estate, the potential it unlocks, and how you can prepare for an AI-driven future, tune in now! Key Points From This Episode: Who is Kevin Brenner: our guest’s introduction and background.Kevin’s thoughts on AI and the future of the business world.How he translated his military experience into a foundation for business success.Kevin shares how he ventured into the world of AI, and ultimately mastered itHe sheds light on the easiest way to get started in AI.The 5 elements of an AI prompt.Raising capital with the help of AI.Kevin explains how they utilize AI at PropertyBots™ and the potential applications of AI.How to prepare for the AI-driven workforce of tomorrow. Find out more about PropertyBots™. Links Mentioned in Today’s Episode: Kevin Brenner on LinkedIn Property Bots™ Active Duty Passive Income Rich Dad Poor Dad BiggerPockets Date With Destiny Event Tony Robbins ChatGPT Claude Gemini Geoff Woods on LinkedIn AI-Driven Leader 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.

    22 min

  5. 12/12/2025

    Episode #250 - Lessons Learned with Joe Fang and Andy Huang

    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 looks like to walk away from a deal. Thanks for listening, and be sure to stay tuned for more from the Real Estate Investor Podcast!  Key Points From This Episode: Welcoming Joe Fang and Andy Huang to the show. A brief overview of the history of this podcast. We share our favorite episodes from this year. A summary of what we’ve experienced in 2025. Expanding on our outlook for the year ahead.We discuss what it’s like to walk away from a deal. Links Mentioned in Today’s Episode: Joe Fang on LinkedIn Andy Huang 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.

    23 min

  6. 11/28/2025

    Episode #249 - Behind the Numbers- Wins, Struggles & Creatively Growing NOI

    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 team crafted a business plan centered on water savings, staff optimization, and cost-effective upgrades. Gary breaks down the improvements that delivered the biggest impact, from high-efficiency plumbing fixtures and privacy fences to selective painting and smart amenity additions. He also shares the early challenges, including occupancy dips and renovation difficulties, and how focusing on controllables helped stabilize the asset and lift NOI (Net Operating Income) by 36% in the first year. Tune in for a transparent look at the wins, struggles, and strategic pivots behind this value-add execution! Key Points From This Episode: Why Gary chose to spotlight Icon on Spanish Trail as a case study.How limited deal flow in Tucson in 2023 created a rare buying opportunity.What was appealing about the deal: scale, quality, and discounted pricing.An overview of the business plan’s focus on water savings and operational efficiencies.Targeted upgrades, including low-flow fixtures and privacy fences.Selective repainting and amenity improvements to enhance the property.How cost controls and efficiencies lifted NOI by more than 36% in year one.Navigating early struggles with occupancy and constraints on pushing rents.Capital-raising challenges due to tight liquidity and investor uncertainty.Washer-dryer additions as a controllable income-generating upgrade.Refinancing the property to lower-rate debt and greater savings.Community-building as a driver of retention and resident satisfaction.Gary’s key lessons for focusing on controllables, efficiency, and stability.Current investment opportunities, from Class A and C options to Icon on Headley. Links Mentioned in Today’s Episode: Icon on Spanish Trail Icon on Headley Email Andy Huang, Investor Relations Manager Andy Huang 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.

    23 min

  7. 11/14/2025

    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

  8. 10/31/2025

    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
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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 - 2026
  • Episodes
    253
  • Rating
    Clean
  • Copyright
    © 2026 Real Estate Investor Podcast
  • Show Website
    Real Estate Investor Podcast

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