Real Estate Investor Podcast

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 it
• He 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.

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.

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.

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.

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.

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.

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.

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.

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.