Real Estate Investor Podcast

The Real Estate Investor Podcast, hosted by Gary Lipsky.

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Latest Episodes

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

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

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 partners (LPs). Through his daily posts, newsletter, and investing partner platform, he helps LPs avoid costly mistakes and spot opportunities others miss. During the conversation, Aleksey explains the difference between REITs and funds and how return profiles compare across REITs, funds, and syndications. Discover why the Internal Rate of Return (IRR) metric is flawed, Aleksey’s “three pillars” of LP investing, why investors should vet General Partners (GPs), and the biggest mistakes to avoid. Join Gary and Aleksey to learn why downside risk matters, what distorts deal projections, and why honesty, not perfection, builds investor trust. Tune in now!


Key Points From This Episode:

  • Background about Aleksey and how he helps LPs evaluate real estate deals.
  • Hear what got him interested in educating LPs to make better investment decisions.
  • The difference between a Real Estate Investment Trust (REIT) and a real estate fund. 
  • Find out how return profiles compare across REITs, funds, and syndications.
  • Issues with the Internal Rate of Return (IRR) metric and why it should be avoided.
  • Discover Aleksey’s “three pillars” of LP investing and what makes it effective.
  • Learn why educating yourself (or sitting out) is better than gambling on a deal.
  • Unpack the biggest and most common mistakes Aleksey sees from both GPs and LPs.
  • How to approach capital calls and why your best investors are your existing ones.
  • Explore what is often missing from investment decks and what to include instead.
  • Aleksey’s key advice for LPs: study 100 deals and trust the reps.


Links Mentioned in Today’s Episode:

Aleksey Chernobelskiy on LinkedIn

Aleksey Chernobelskiy on X

Centrio Capital Partners

GP-LP Match

Limited Partner (LP) Investing Lessons Newsletter

‘10 reasons why deal flow rules the world’

Invest Smart

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

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

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 framework for creating financial freedom by investing in commercial real estate. Kevin begins our conversation by explaining who he is, what he does, and how he got into the world of real estate. Then, we discover what piqued his interest in mobile home parks, how he invested before stumbling upon this revenue stream, the challenges he’s overcome and lessons learned since and because of The Great Recession, and the importance of discipline and planning for the worst when entering new investments or developments. To end, we unpack parking lots and why this is a crucial business model to take note of, and we explore why seasoned real estate professionals appreciate the value of longer holds.    


Key Points From This Episode:

  • Kevin Bupp explains who he is, what he does, and how he got into real estate. 
  • Understanding what drew him to mobile home parks and how he invested before this venture.
  • The lessons he learned from The Great Recession of 2008.
  • Challenges he and his company have faced and ultimately, overcome. 
  • The power of discipline, planning for the worst, and being secure in real estate fundamentals. 
  • Parking lots: Why this relatively underexplored business model deserves a second look.  
  • How real estate experience reveals the value of longer holds. 


Links Mentioned in Today’s Episode:

Kevin Bupp

Kevin Bupp on LinkedIn

Kevin Bupp on Instagram

Kevin Bupp on Facebook

Kevin Bupp on YouTube 

The Cash Flow Investor 

The Passive Investors Guide to Parking Lot Profits

Real Estate Investing for Cash Flow | Mobile Home Park

Sunrise Capital Investors  

Invest with Sunrise Capital Investors

Brian Spear on LinkedIn

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 #227: Joe Fang: Navigating Uncertain Times

Episode #227: Joe Fang: Navigating Uncertain Times

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 and Joe discuss their recent acquisition of Icon on Headley, the importance of strategic staffing and property synergies, and how macroeconomic forces (like tariffs and inflation) impact real estate. Joe also shares his insights on interest rate trends and why he believes rates will begin to drop in 2025. For a deeper understanding of market shifts and how to position yourself for success in an unpredictable economy, don’t miss this thought-provoking conversation with Joe Fang!


Key Points From This Episode:

  • Insight into a recent acquisition: Icon on Headley and its strategic benefits.
  • How sister properties create cost savings and efficiency.
  • The state of the multifamily real estate market and deal flow trends.
  • Interest rate trends: why Joe predicts rates will drop in the second half of the year.
  • The real impact of tariffs on real estate and material costs.
  • Strategies for increasing NOI through operational efficiencies.
  • Choosing the right type of financing and structuring deals effectively.
  • Lessons from market volatility: avoiding overleveraging and maintaining liquidity.
  • Why institutional investors are preparing to jump back into real estate.


Links Mentioned in Today’s Episode:

Invest Smart: Spotting Red Flags in Real Estate Syndications

Joseph Fang on LinkedIn

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 #226: Passive Investing Master Class with Jeremy Roll

Episode #226: Passive Investing Master Class with Jeremy Roll

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 manages a network of investors and is also a co-founder of For Investors By Investors (FiBi), where he shares his extensive knowledge of low-risk, predictable investment strategies. In our conversation, we discuss market cycles, risk management, and the strategies that have kept him ahead of economic downturns. He talks about the warning signs he saw in 2020, why it was an overheated market, and the dangerous reliance on floating-rate bridge loans. We explore the role of economic cycles, the impact of interest rates, and why sticking to a disciplined investment framework is crucial. We also delve into how multifamily construction trends might delay a recession, what asset classes have the most future potential, and much more. Join us to discover how passive investors should educate themselves, avoid common pitfalls, and navigate market uncertainty with Jeremy Roll. Tune in now!


Key Points From This Episode:

  • Jeremy's background in corporate America before transitioning to full-time investing.
  • He explains the early warning signs in real estate he noticed during the early 2020s.
  • Unpack the current challenges in real estate investing and how he overcame them. 
  • Uncover the pros and cons of exiting deals early versus staying in the market longer.
  • How money printing causes market distortions and how this impacted real estate.
  • Learn about a set investment “box” and how to stick to a strategy despite market hype.
  • Why investors should avoid deals that don’t fit a disciplined investment framework.
  • Hear why his biggest win for the year was avoiding floating-rate bridge loan investments.
  • Jeremy shares his outlook for real estate in 2025 and beyond. 
  • Explore the role of interest rates and the cautious approach to managing inflation.
  • Acceleration of an economic slowdown due to government job cuts and policy changes.
  • Find out about what asset classes to invest in and valuable resources for passive investors.
  • Tools and strategies that help Jeremy be a better investor and to contact him. 


Links Mentioned in Today’s Episode:

Jeremy Roll on LinkedIn

Jeremy Roll Email

FiBi Capital

Episode 96: Bullish or Bearish, with Jeremy Roll

Invest Smart

Calculated Risk Blog

ShadowStats

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 #225: Advanced Class on Asset Management with Mike Taravella

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

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 portfolio performance. In our conversation, Mike shares his journey from corporate accounting to real estate and explains how he leveraged financial systems, automation, and AI tools to streamline asset management. We delve into the benefits of structured asset management practices and the concept of Net Promoter Scores. We uncover the power of secret shopping, the importance of financial oversight, and how to overcome CapEx mismanagement hurdles. Mike also unpacks 2024’s real estate market challenges, explores why high-impact KPIs are essential, and explains his approach to handling property managers. Join us to learn how to avoid common mistakes, streamline operations, and maximize portfolio performance in a rapidly shifting market with Mike Taravella! Tune in now!


Key Points From This Episode:

  • How Mike transitioned from corporate accounting to real estate portfolio.
  • Find out how AI can streamline financial reviews and reporting in real estate.
  • Explore how Net Promoter Scores and tenant surveys reveal hidden property issues.
  • Learn how to effectively communicate and work with property managers. 
  • Mike's method for tracking and monitoring assets and the power of secret shopping.
  • Why consistent tracking and monitoring improves performance and accountability.
  • Uncover the various challenges and trends in the asset management landscape. 
  • The biggest struggle he faced in 2024 and how he was able to overcome it.
  • Hear how CapEx mismanagement can negatively impact investment returns.
  • Fraud in property management and ways to prevent it.


Links Mentioned in Today’s Episode:

Mike Taravella 

Mike Taravella on LinkedIn

Mike Taravella on X

Mike Taravella on Instagram

Mike Taravella on YouTube

Niche Holdings

ChatGPT

Claude

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

Episode #224: What You Must Know About the Economy and Real Estate Investing in 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 of Linneman Associates, Dr. Linneman is an advisor to leading corporations and multiple published authors. Join us for an informative discussion and a fascinating growth forecast for the coming year in light of productivity, population growth, and geopolitical events. We also discuss tariffs and inflation, the impact of natural disasters on the housing market, and the potential of the build-to-rent market. Don’t miss today’s enriching conversation. 


Key Points From This Episode:

  • Welcome to leading economic expert and author of Real Estate Finance and Investments, Dr. Peter Linneman. 
  • Dr. Linneman’s thoughts on economic, real estate, and employment growth in 2025.
  • How the economy has developed following the 2020 pandemic. 
  • Peter’s opinions on USAID and its impact in Africa. 
  • His predictions on how the price of single-family housing and apartments will change in the coming years. 
  • How tariffs will affect inflation. 
  • Advice for lenders on how to put their money to work. 
  • How the LA fires may affect the LA inventory market. 
  • His thoughts on where student housing is reliable.
  • Insurance rates and expenses in the future. 
  • The build-to-rent market and how it affects the market. 
  • Peter’s thoughts on AI.


Links Mentioned in Today’s Episode:

Peter Linneman on X

Peter Linneman on LinkedIn

SAM Elimu Charity
Linneman Associates

Real Estate Finance Textbook

The Great Age Reboot

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

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

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 focuses on finding low-risk, high-return opportunities that benefit both tenants and investors. Tune in to hear how Austin got into the business of real estate and the key data points they look at when choosing their locations. He even highlights risk return ratios they analyze to make investments safer. For all this, and more, start listening now. 


Key Points From This Episode:

  • Listeners are introduced to today’s guest, Austin Hair.
  • More about what he does and how he got into the business of real estate.
  • Key data points they look for when choosing locations. 
  • Why they haven’t tried their approach on any other asset class.
  • He highlights other risk-return rations they look at to make investments safer.
  • The pros and cons of the medical retail asset class.
  • Austin shares his thoughts on what he’s seeing (geographically) for 2025 and the markets he is looking at for the medical field.


Links Mentioned in Today’s Episode:

Austin Hair on LinkedIn

Austin Hair on Instagram

Austin Hair on X

Austin Hair on Facebook

Austin Hair on YouTube

Leaders Real Estate

Helping Healthcare Scale

Rich Dad Poor Dad: What The Rich Teach Their Kids About Money That the Poor and Middle Class Do Not! 

The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich

Entrepreneurial Leap: Do You Have What it Takes to Become an Entrepreneur? 

Pitney Bowes

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 #222: George McCleary – Overcoming Squatters and Title Fraud

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

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 estate scams, and he gained viral fame by exposing how effortlessly a house can be stolen in his social media video, “I stole a House.” We begin with George’s professional background and how he reacted to his new-found fame before he shares some incredible squatting stories from his experience. Then, we unpack squatting legalities, the costs to homeowners when squatters take over, common character traits among most squatters, and how squatting can lead to investment losses. To end, George unpacks title fraud and the many details we may not know about equity being stolen, and he shares crucial solutions for preventing squatting and title fraud.   


Key Points From This Episode:

  • Defender Network’s CEO, George McCleary explains who he is and what he does. 
  • How he was stunned by his viral fame before embracing it. 
  • Crazy, unbelievable, and sensational squatting stories. 
  • How to legally remove squatters from your home. 
  • The eyewatering costs of squatting, and common squatter characteristics.
  • How squatting ruins investments. 
  • The ins and outs of title fraud. 
  • How to prevent squatting and title fraud. 


Links Mentioned in Today’s Episode:

George McCleary

George McCleary on LinkedIn

George McCleary on Instagram

George McCleary on Facebook

George McCleary on X

George McCleary on TikTok

George McCleary on YouTube 

I Stole a House | George McCleary on X

Title Fraud Defender- 20% off Promo Code: BODC

Squatter Defender- 20% off Promo Code: BODC  

Gobundance 

David Greene on LinkedIn

American Land Title Association

Gobble Gobble Give Thanksgiving Charity

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

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

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 the evolution of her business, we discuss Hannah’s self-education and the key insights that have shaped her career. We also unpack the role of fear and why a little bit of trepidation can be a good thing for entrepreneurs, what Hannah sees as her greatest achievement, and what changes when you realize that although finances are important, there is much more to life than money. Join us today to hear all this and more. 

Key Points From This Episode:

  • Introducing guest, Hannah Hammond, a serial entrepreneur in property management, lending and construction. 
  • The book that sparked her interest in finding financial success.
  • What being an entrepreneur is truly about: freedom. 
  • How her debt fund began and what it has evolved into in 2025. 
  • Some of the books that have been pivotal to Hannah’s self-education. 
  • The basis of real estate and how she came to realize what it truly is. 
  • Hannah’s relationship with fear. 
  • Why she believes in building slowly and steadily.
  • What Hannah sees as her greatest achievement: personal growth. 
  • Embracing the perspective that happiness is more important than money.
  • Hannah’s upcoming podcast. 


Links Mentioned in Today’s Episode:

Hannah Hammond on LinkedIn
Hannah Hammond on Instagram

Hannah Hammond on YouTube

Hannah Hammond on X

The Hannah Hammond Show

Rich Dad, Poor Dad

Dan Sullivan
The Millionaire Real Estate Investor

Rich Dad’s Guide to Investing

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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