Real Estate Investor Podcast

The Real Estate Investor Podcast, hosted by Gary Lipsky.

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Latest Episodes

Episode #218: Year End Tax Strategies with Brandon Hall

Episode #218: Year End Tax Strategies with Brandon Hall

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 navigate the short-term rental loophole. He breaks down some of the pitfalls of trying to save money in the short term and the benefits of thinking long-term and reducing your effective tax rate, offering a clear breakdown of how to save money in the long run. Discover different long-term tax saving strategies, like the BRRRR method, and how to approach mechanisms like a 1031 exchange. Brandon also breaks down how to deal with passive activity netting, qualifying as a real estate professional, and why it’s essential that you master documentation and admin work to successfully utilize the short-term rental loophole. Don’t miss out on this must-listen for investors aiming to leverage tax advantages wisely and avoid costly pitfalls!


Key Points From This Episode:

  • Expected upcoming tax changes with the new Republican administration.
  • Advice for handling bonus depreciation at the end of the year.
  • When and how to get your cost segregation (cost-seg) study done.
  • How audits have increased and why you should document all receipts.
  • Thinking long term with your taxes and how to reduce your effective tax rate with tax planning.
  • The tax benefits of investing in oil and gas (and whether it’s worth it).
  • How to successfully use the BRRRR strategy: buy, rehab, rent, refinance, repeat.
  • The benefits and drawbacks of a 1031 exchange, like the swap and drop method.
  • Discerning between passive and non-passive activities and how to use them.
  • Passive activity netting: what it is and how to leverage it.
  • The requirements for qualifying as a real estate professional.
  • A breakdown of how to navigate the short-term rental loophole.
  • Taking on the administrative burden of the short-term rental loophole.
  • A cautionary tale from a 2020 tax court case, Lucero vs. Commissioner.


Links Mentioned in Today’s Episode:

Brandon Hall on LinkedIn

Hall CPA

Hall CPA on X

Hall CPA on Facebook

Episode 120: Real Estate Tax Changes with Brandon Hall

Asset Management Mastery Facebook Group

Break of Day Capital

Break of Day Capital Instagram

Break of Day Capital YouTube

Gary Lipsky on LinkedIn

Joseph Fang on LinkedIn

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

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

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 helping property managers streamline processes and convert leads into leases. Tuning in, you’ll hear how Jon approaches website builds for clients, property photography, and marketing spend. He shares his thoughts on having a digital presence you can control, why ILS is a great place to prioritize this, and why, although it is the most expensive place to advertise, he recommends Google above all other options. Finally, we discuss the importance of getting the most out of AI to optimize marketing efforts and what you can really do with the data that it provides. Thanks for tuning in. 

Key Points From This Episode:

  • Introducing Jon Simpson and his journey to multi-family.
  • His client onboarding process and where he begins to work with them. 
  • How he approaches building a website when a client has an existing site.
  • Understanding photography rights and partnering with the appropriate companies. 
  • Using Google Business and Google Ads to maximize marketing efforts and drive visits to the site. 
  • How much you should actually be spending on marketing. 
  • Why you need to have some presence on ILS. 
  • Understanding why Google is the best place to spend your money even though it is expensive.
  • How Jon leverages the power of AI to optimize his marketing efforts.
  • Why he is a big believer in geofencing for apartments. 
  • Understanding the lead time of your marketing efforts. 


Links Mentioned in Today’s Episode:

Jon Simpson on LinkedIn

Jon Simpson on X

Swifty

Criterion.B

RPM Real Estate

NRE Developments

A.G. Spanos Companies

AMLI Residential

Zumper
HomeJab

Apartments Geofencing

Asset Management Mastery Facebook Group

Break of Day Capital
Break of Day Capital Instagram

Break of Day Capital YouTube

Gary Lipsky on LinkedIn

Joseph Fang on LinkedIn

Episode #216: Multifamily Market Update with J Scott

Episode #216: Multifamily Market Update with J Scott

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 of the recent interest rate cuts on mortgage and cap rates, explains trends in housing supply and demand, and examines how inflation and economic shifts are influencing multifamily properties. He also shares advice on overcoming rising expenses, navigating distressed debt opportunities, and avoiding common mistakes as a real estate investor. Join us to gain insights on managing multifamily investments in a rapidly evolving market with J Scott. Tune in now!


Key Points From This Episode:

  • The influence of recent rate cuts on mortgage rates and the multifamily market.
  • Cap rates and why current conditions create a buyer’s market.
  • Navigating market volatility and why buying during downturns is a good strategy.
  • Key economic indicators that J tracks to uncover industry trends. 
  • How inflation has capped rent growth while increasing operating costs.
  • Perspectives on the most common mistakes real estate investors make.
  • J’s advice: invest for the long term and avoid selling assets prematurely.


Links Mentioned in Today’s Episode:

J Scott

J Scott on X

J Scott on LinkedIn

Bar Down Investments

Drunk Real Estate Podcast

BiggerPockets 

BiggerPockets Books by J Scott

Asset Management Mastery Facebook Group

Break of Day Capital
Break of Day Capital Instagram

Break of Day Capital YouTube

Gary Lipsky on LinkedIn

Joseph Fang on LinkedIn

Episode #215: The 7 Levels of Wealth with Aaron West

Episode #215: The 7 Levels of Wealth with Aaron West

Ever wonder what it truly takes to reach financial freedom? In this episode, Aaron West breaks down the mindset and steps behind his "7 Levels of Wealth" concept. Aaron is the owner of The West Experience Real Estate Group and has built a successful career in real estate, including fix-and-flips and wealth-building strategies. He is passionate about helping entrepreneurs achieve financial freedom and live fulfilling lives. In our conversation, Aaron delves into his journey from growing up in poverty to building a successful real estate portfolio and creating wealth. He discusses the common lessons learned from interviewing successful entrepreneurs and the importance of deciding to be wealthy, persevering through struggles, and the power of relationships. Aaron shares actionable advice on how entrepreneurs can transform failures into successes, stay focused on their niche, and leverage the concept of "stewardship" over their finances. Join us to discover the secret to living in abundance and learn why giving back is vital to building long-term wealth with Aaron West!


Key Points From This Episode:

  • Aaron's background, his life growing up, and his journey into real estate.
  • The 7 Levels of Wealth concept and how to build a foundation for future wealth.
  • Why true wealth involves a holistic approach and is not just about financial success.
  • Shifting from a mindset of instant gratification to long-term stewardship of money.
  • Explore the importance of focusing on your niche and avoiding distractions.
  • Steps for navigating the personal transformations needed for long-term success.
  • Find out why fostering authentic relationships with people is vital for success.
  • How living in abundance through helping others brings more wealth and fulfillment.


Links Mentioned in Today’s Episode:

Aaron West on Instagram

Aaron West on TikTok

Aaron West on Facebook

The West Experience Real Estate Group

Gobundance

Rich Dad Poor Dad

Rich Dad

Asset Management Mastery Facebook Group

Break of Day Capital
Break of Day Capital Instagram

Break of Day Capital YouTube

Gary Lipsky on LinkedIn

Joseph Fang on LinkedIn

Episode #214: Robert Helms – Finding Investment Opportunities

Episode #214: Robert Helms – Finding Investment Opportunities

Real estate investing is not about numbers or transactions, it’s a relationship business! This is the opinion of today’s incredibly successful guest, real estate investor, and host of the podcast, The Real Estate Guys, Robert Helms. He joins us today to discuss his career and all things investment opportunities. Tuning in, you’ll hear all about Robert’s impressive career, why he tries not to sell property and instead collect it, the importance of narrowing your market focus, and why you need a personal investment philosophy. We delve into Robert’s experience in international investment, his favorite markets, and the benefits of investing outside the US before discussing where the biggest investment opportunities lie in real estate. Our guest even shares the two biggest contributors to his success. Finally, Robert walks us through the biggest mistake he made in his career and the lessons he learned from it. Thanks for listening! 


Key Points From This Episode:

  • Introducing today’s illustrious guest, Robert Helms. 
  • Robert tells us about his incredible career and why he sees himself as a real-estate ‘collector’.
  • Why he doesn’t think a good investor can focus on too many markets at once. 
  • The importance of having a personal investment philosophy. 
  • Robert tells us where he sees real estate investment evolving in the future. 
  • A few benefits of investing outside of the US and Robert’s favorite international markets.
  • Where Robert thinks the biggest opportunity in real estate lies. 
  • The two biggest factors that have contributed to Robert’s success. 
  • Robert shares the most difficult lesson he’s learned throughout his career. 


Links Mentioned in Today’s Episode:

Robert Helms

Robert Helms on Instagram

Equity Happens: Building Lifelong Wealth with Real Estate

The Real Estate Guys

Asset Management Mastery Facebook Group

Break of Day Capital
Break of Day Capital Instagram

Break of Day Capital YouTube

Gary Lipsky on LinkedIn

Joseph Fang on LinkedIn

Episode #213: Living a Life of Abundance with Matt King

Episode #213: Living a Life of Abundance with Matt King

Living in abundance starts with cultivating the right mindset, and it is a consistent effort to stay motivated to live up to your full potential. To explain how a mentality of abundance improved his life, we are joined today by the CEO of GoBundance, Matt King. GoBundance is a member-led mastermind built for hardworking overachievers, and Matt describes what his role as CEO entails and how he finds joy at work. We unpack ways of escaping the mental prison of imposter syndrome, how the people and places around you influence your success, why hard work is the only true path to prosperity, and why Matt’s 29029 Everesting challenge experience is the perfect example of the benefits of dedication and perseverance. To end, Matt explains why even the worst life experiences are still a gift and a blessing, the value of building relationships with like-minded people, how to build a mindset of abundance, and helpful resources to help you unlock your full potential.  


Key Points From This Episode:

  • GoBundance CEO, Matt King explains who he is and what he does. 
  • How Matt knows when he’s limiting himself, and how he escapes this mental prison.
  • The people and places that paved his road to success. 
  • Why hard work is the only route to prosperity, and how to avoid taking the easy road. 
  • Matt’s reasons for taking on the 29029 challenge, and what he gained from the experience. 
  • Why he believes that every life experience—even negative ones—is a gift.
  • What he means when he says “eagles fly with eagles.”
  • How living with intention and creating a vision helps to build a mindset of abundance. 
  • Helpful resources for living a life with purpose and fulfilling your potential. 


Links Mentioned in Today’s Episode:

Matt King

Matt King on LinkedIn

Matt King on Instagram 

Matt King on YouTube 

Matt King Email

GoBundance  

David Osborne on LinkedIn 

29029 Everesting 

Rock Thomas 

Ego is the Enemy 

As a Man Thinketh

Asset Management Mastery Facebook Group

Break of Day Capital
Break of Day Capital Instagram

Break of Day Capital YouTube

Gary Lipsky on LinkedIn

Joseph Fang on LinkedIn

Episode #212: Raising Capital with Ryan Miller

Episode #212: Raising Capital with Ryan Miller

What does it take to successfully raise capital and build lasting investor relationships? In this episode of The Real Estate Investor Podcast, we’re joined by Ryan Miller; Founder and CEO of Pentium Capital Partners and host of the global top 2% podcast, Making Billions with Ryan Miller, who shares his 15 years of experience navigating the world of finance and capital raising. Ryan takes us through his journey from humble beginnings to managing multimillion-dollar portfolios, outlining his approach to leveraging reputation, relationships, and results. He offers actionable advice for getting started; including the importance of building a network using his Triple F rule, refining your pitch, and practicing generosity when networking. If you’re looking to elevate your fundraising game, this episode provides invaluable strategies for attracting investors and ensuring that deals come your way. To learn how to build a strong capital pipeline and achieve long-term success in real estate investing, don’t miss this inspiring conversation with visionary finance leader, Ryan Miller!


Key Points From This Episode:

  • The story of how Ryan built his first venture capital portfolio and never looked back.
  • Three Rs and Triple F: best practices for raising capital.
  • Practical tips to help you find investors and refine your pitch.
  • Common mistakes that many fundraisers make and how to avoid them.
  • How joining boards and associations can boost your network and success.
  • Key disciplines of capital raisers: never eat alone, always learn their story, and more.
  • Why you must be willing to give in order to receive.


Links Mentioned in Today’s Episode:

Pentium Capital Partners

Making Billions with Ryan Miller Podcast

Ryan Miller on LinkedIn

Ryan Miller on Instagram

Ryan Miller on YouTube

Ryan Miller on X

Ryan Miller Email

Fund Raise Capital

Never Eat Alone: And Other Secrets to Success, One Relationship at a Time

Asset Management Mastery Facebook Group

Break of Day Capital
Break of Day Capital Instagram

Break of Day Capital YouTube

Gary Lipsky on LinkedIn

Joseph Fang on LinkedIn

Episode #211: Shane Thomas – Quality Asset Management

Episode #211: Shane Thomas – Quality Asset Management

Asset management requires constant forward-thinking to ensure long-term success. Today we are joined by the co-founder of Catalyst Equity Partners, Shane Thomas, to discuss quality asset management. Tuning in, you’ll hear about Shane’s business, why he decided to open an in-house construction business, the biggest asset management struggles at the moment, how he overcomes them, and more! We also dive into the importance of effective communication, playing the long game in asset management, and how Shane’s CPA background has contributed to his success. Plus, Shane shares valuable advice on hiring earlier in your asset management business. Press play now to catch it all!


Key Points From This Episode:

  • Introducing today’s guest, Shane Thomas. 
  • A brief overview of his business, Catalyst Equity Partners. 
  • What inspired him to start CEP Construction. 
  • Shane’s biggest, and most recent, struggles with asset management. 
  • The importance of effective communication in good and bad times. 
  • Playing for the long game in asset management. 
  • How Shane’s CPA background helped him in property management. 


Links Mentioned in Today’s Episode:

Shane Thomas on LinkedIn

Shane Thomas Email Address

Catalyst Equity Partners

Asset Management Mastery Facebook Group

Break of Day Capital
Break of Day Capital Instagram

Break of Day Capital YouTube

Gary Lipsky on LinkedIn

Joseph Fang on LinkedIn

Episode #210: Assisted Living 101 with Isabelle Guarino

Episode #210: Assisted Living 101 with Isabelle Guarino

As a nation, we know very little about residential assisted living (RAL) compared to other real estate categories. So today, we welcome the two-time bestselling author and COO of Residential Assisted Living Academy (RALA), Isabelle Guarino, who sheds more light on the importance of RAL and how you can get involved. Named as one of the “Top Influencers of Senior Housing” and a two-time recipient of "The Future Leader of Assisted Living" title, Isabelle is undoubtedly America’s top coach and trainer for all things RAL. She begins with a detailed breakdown of RALA before diving into the common pitfalls of operators new to RAL, the qualifications and hires that are required to run an assisted living facility, the limitations that RAL administrators have to work around, and how a residency care plan differs entirely from a tenant/landlord agreement. We also unpack proper ways to go about RAL research, helpful tools and technologies that are currently available, how scaling works in RAL, and everything else that you need to know to kick-start your residential assisted living venture. 


Key Points From This Episode:

  • RAL guru Isabelle Guarino explains the work of the Residential Assisted Living Academy (RALA). 
  • Common mistakes that operators make when joining the RAL space. 
  • The qualifications and key hires necessary to run a residential assisted living facility. 
  • Understanding the limitations placed on RAL administrators. 
  • Diving deeper into the numbers and economic implications. 
  • The differences between a tenant/landlord agreement and a residency care plan. 
  • How to find the right data when doing RAL research.  
  • A closer examination of how RALA trains its students to be successful. 
  • The future of RAL, and helpful technologies and tools to use. 
  • How scaling transpires in rental assisted living.
  • Everything else that you need to know before joining RAL. 


Links Mentioned in Today’s Episode:

Isabelle Guarino on LinkedIn

Isabelle Guarino on Instagram 

Residential Assisted Living Academy | RALA 

RAL101

The Young Boss Podcast 

Living Legacy 

Young Boss

The Silver Tsunami of Seniors 

Residential Assisted Living National Association | RALNA 

Genworth 

CarePredict

Asset Management Mastery Facebook Group

Break of Day Capital
Break of Day Capital Instagram

Break of Day Capital YouTube

Gary Lipsky on LinkedIn

Joseph Fang on LinkedIn

Bio of Real Estate Investor Podcast

The Real Estate Investor Podcast, hosted by Gary Lipsky of Break of Day Capital, is a valuable resource for investors seeking to build wealth and make a positive impact in communities. 

With over 30 years of operations and management experience, including more than 20 years in real estate investments totaling over $1/4 Billion, Gary brings a wealth of knowledge and expertise to the show.

In each episode, Gary engages in insightful conversations with leading experts in the real estate industry. Together, they cover a wide range of subjects, providing listeners with best-in-class practices and strategies to navigate the world of real estate investing. 

The podcast offers practical advice and actionable insights that can help investors achieve their financial goals and create a lasting legacy.

Gary's no-nonsense approach ensures that listeners receive 100% straight talk. The conversations on the Real Estate Investor Podcast are transparent, honest, and geared towards empowering investors with the information they need to make informed decisions.

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