Real Estate Investor Podcast

Break of Day Capital
Break of Day Capital Instagram

Hannah Hammond on LinkedIn
Hannah Hammond on Instagram

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 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

Break of Day Capital
Break of Day Capital Instagram

Sayan Renovations & Construction

Episode #220: Ruben Ortiz – Multifamily Capex Projects

What makes a successful relationship between operators and general contractors? In today's episode, we speak with Ruben Ortiz, founder of Sayan Renovations & Construction. Based in Dallas, Ruben and his team tackle complex multifamily Capex projects with a focus on quality, innovation, and authenticity. In our conversation, Ruben shares his journey from working alongside his father in construction to leading a nationwide team transforming multifamily properties. We discuss how Sayan Renovations & Construction builds strong GC-operator relationships, hear practical advice on value-add projects, and uncover actionable insights to help investors optimize their Capex strategies. Join us to learn how to create lasting impact, improve ROI, and streamline construction processes in your multifamily investments with Ruben Ortiz. Tune in now!

Key Points From This Episode:

Ruben’s journey from laborer to founder of Sayan Renovations & Construction.
How Ruben’s team tackles large-scale multifamily Capex projects with precision.
Learn why honesty and transparency are vital in building GC-operator relationships.
Discover the common pitfalls operators face when selecting a GC.
The importance of early GC involvement in budgeting and planning.
Ways branding and first impressions can transform leasing success.
Cost-effective upgrades that significantly enhance multifamily properties.
Uncover the ROI potential of exterior renovations and amenity improvements.
Advice on how operators can work with GCs effectively and the pitfalls to avoid.
Hear about Ruben’s standout projects and his approach to nationwide coordination.

Links Mentioned in Today’s Episode:

Ruben Ortiz on LinkedIn

Sayan Renovations & Construction on Instagram

Sayan Renovations & Construction on Facebook

Sayan Renovations & Construction on LinkedIn

Disrupt Equity

Momentum Multifamily

Break of Day Capital
Break of Day Capital Instagram

National Multifamily Housing Conference NMHC

Episode #219: Gary Lipsky- Closing Deals in Today's Environment

Welcome back to a new year and another episode of The Real Estate Investor Podcast with your host, Gary Lipsky of Break of Day Capital. In this episode, Gary dives into today’s topic: finding and closing deals in the current market. He shares insights from their most recent deal, recaps the capital trends of 2024, and offers actionable tips to help you prepare for when deals come to market. Tune in to discover what made this a challenging year for investors, why understanding your market is crucial, and hear Gary’s important public service announcement. Thanks for listening!

Key Points From This Episode:

The focus of today’s episode: finding and closing deals in today’s environment.
Gary shares details about their most recent deal and their plans for the property.
A quick recap of last year’s capital side of things.
What you can do to remain ready for when deals are eventually put out.
What made this year, as an operator, a rough year.
The importance of knowing the market well, and running real estate as a real business.
A public service announcement from Gary.

Links Mentioned in Today’s Episode:

Invest Smart: Spotting Red Flags in Real Estate Syndications

Break of Day Capital
Break of Day Capital Instagram

Episode 120: Real Estate Tax Changes 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

Break of Day Capital Instagram

Break of Day Capital

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

A.G. Spanos Companies

AMLI Residential

Zumper
HomeJab

Apartments Geofencing

Break of Day Capital
Break of Day Capital Instagram

Drunk Real Estate Podcast

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:

BiggerPockets

BiggerPockets Books by J Scott

Break of Day Capital
Break of Day Capital Instagram

The West Experience Real Estate Group

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

Gobundance

Rich Dad Poor Dad

Rich Dad

Break of Day Capital
Break of Day Capital Instagram

Robert Helms on Instagram

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

Equity Happens: Building Lifelong Wealth with Real Estate

The Real Estate Guys

Break of Day Capital
Break of Day Capital Instagram