Real Estate Investor Podcast

Gary Lipsky
  • 5.0 (19)
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  • 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. 2D AGO

    Episode #258: Trevor McGregor – How to Achieve High Performance

    Do you want to get rich beyond belief? Today on the Real Estate Investor Podcast, master coach and real estate investor, Trevor McGregor, joins us to talk about how you can achieve high-performance and true success! Tuning in, you’ll hear all about his investment background and career, what the investor wealth architect identity shift is, stepping into your sage mindset, and so much more. He delves into the five reasons why people fail to scale consistently before discussing how he maximizes his time. Trevor also touches on what he believes is the secret to living: sharing our success with beginners, and tells us how he went from losing everything to having a large, cash-flowing portfolio. Finally, our guest shares his favorite quote of all time and tells us where we can find his special free gift for listeners. If you want more success, wealth, and freedom, then this episode is for you, so be sure to press play now!  Key Points From This Episode: Introducing Trevor McGregor.A brief overview of our guest’s career and investment journey. The investor wealth architect identity shift. Moving away from a saboteur mindset to a sage one. The five reasons people fail to scale consistently. Trevor tells us how he maximizes his time using AI. How he went from losing everything to where he is now. Trevor shares his favorite quotes with listeners.  Links Mentioned in Today’s Episode: Trevor McGregor Rich Beyond Belief Trevor McGregor on LinkedIn Who Not How  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.

    25 min

  2. MAR 13

    Episode #257 - Reed Goossens – Opportunity in the Reset

    When we hit rock bottom, the only place to go is up! Today on the Real Estate Investor Podcast, we welcome real estate entrepreneur, author, host of the top-rated podcast, Investing in the U.S., and founder of Accounting First Group, Reed Goossens, to discuss his stance in the erratic real estate investing world at the moment and to learn about his CPA firm rollup! Tuning in, you’ll hear all about Reed’s impressive career, his move from Australia to America, and how he’s adapted to survive in these difficult times in this industry. He goes on to talk about his opinion of the current state of investing and when and how he feels it will improve. We even chat about his new CPA firm rollup, Accounting First Group, what inspired him to start it, and his goals for the company. This is a thought-provoking and inspiring conversation that you don’t want to miss, so be sure to press play now!  Key Points From This Episode: Welcoming Reed Goossens to the show. His thoughts on the real estate industry at the moment. Changes he’s made to push through this tough investing cycle. Where Reed will be investing in the near future and why. Reed tells us about his CPA firm rollup and his goals for it.  Links Mentioned in Today’s Episode: Reed Goossens Reed Goossens on LinkedIn Reed Goossens Email Address Reed Goossens on Instagram Reed Goossens on Facebook Investing in the U.S. Accounting First Group  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

  3. MAR 6

    Episode #256 - Ian Tudor – The Pivot to Purpose

    What does it look like to switch from closing deals to building communities with real long-term impact? In this episode of the Real Estate Investor Podcast, host Gary Lipsky sits down with Ian Tudor, partner at JIK Holdings, to discuss Ian’s career path from corporate finance to mobile home parks and into land development. Ian shares how institutional underwriting influenced his investing mindset, how he and his partners built a portfolio by buying smaller mobile home parks, and what he learned from living on-site to stabilize a large property. He breaks down land development for investors who are new to the space, the entitlement timeline, the upfront costs, and why development can sometimes feel slow and risky. Ian also shares details about his current work in Los Angeles County and his goal to create more attainable homeownership opportunities. To hear how Ian evaluates risk across strategies, what it takes to move from value-add to development, and why he believes this is a golden age for small developers, tune in now! Key Points From This Episode: Ian’s background and why he shifted from mobile home parks to land development.Hear how Ian’s start in corporate finance prepared him for real estate investing.Discover what got him interested in mobile home parks and why he went all-in.Learn how Ian and his partners built a mobile home park portfolio from scratch.What Ian learned from living on-site while helping turn around a large mobile home park.Unpack what changed in mobile home parks and why he decided to exit.Explore what land development involves and why the timeline is much longer.He shares how many deals he works on at once and why the pace can feel slow.Details about a big project Ian is currently working on and what it is trying to solve.Find out what the four-unit plan looks like in size, layout, and lot design.Insights into the progress of the project and the kinds of challenges he faces. Links Mentioned in Today’s Episode: Ian Tudor 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

  4. FEB 13

    Episode #255 - Joseph Fang – Market Signals and New Opportunities

    In this episode of the Real Estate Investor Podcast, Gary Lipsky welcomes back Joseph Fang of Break of Day Capital to unpack the current real estate market signals and how those signals are shaping new opportunities on the acquisition side. Joseph shares why basis and buying below replacement cost matter in today’s environment, what a value-add plan looks like when it’s focused on deferred maintenance, and how targeted fixes can improve resident experience, reduce turnover, and increase rent growth. They also discuss rate expectations, liquidity, lender behavior, and what Joseph and Gary are hearing across the market about timing, cap rates, expenses, and why strong asset management execution is becoming essential again. Tune in to learn what it takes to buy and operate confidently in an uncertain cycle with Gary Lipsky and Joseph Fang! Key Points From This Episode: Welcome back to Joseph Fang, Director of Investor Relations at Break of Day Capital.Hear about an exciting new deal that Break of Day Capital has closed on. Find out how deferred maintenance reduces retention and the associated costs.Why deferred maintenance is essential and increases the value of a property.Discover what investors should do after a typical investment cycle. Why Joseph likes investing when multifamily sentiment is driven by fear and uncertainty.Unpack Trump’s Fed pick and how policy direction could impact real estate investing.Overview of the current financing landscape and how it is expected to change.Gary shares highlights from the recent NMHC Annual Conference in Vegas.Explore how lender behavior has shifted and why buying now could pay off in the long term.Joseph shares his opinion about the future of real estate and why he has a positive outlook. Links Mentioned in Today’s Episode: Joseph Fang on LinkedIn National Multifamily Housing Council (NMHC) 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. 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

  6. 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

  7. 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

  8. 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
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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
    257
  • Rating
    Clean
  • Copyright
    © 2026 Real Estate Investor Podcast
  • Show Website
    Real Estate Investor Podcast

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