On this episode of Zen and the Art of Real Estate Investing, Jonathan welcomes back multifamily investor, financial educator, and newly certified money coach Gino Barbaro. Known for his work with Jake & Gino and his educational focus on long-term wealth, Gino joins Jonathan to unpack the deeper connection between money, mindset, family values, and building a legacy. The discussion moves beyond real estate strategy into the emotional and psychological frameworks that shape financial behavior across generations.

As the conversation unfolds, Jonathan and Gino explore how childhood experiences influence adult money patterns, why transparency within families matters, and how parents can introduce financial literacy without pressure or fear. Gino also breaks down his philosophy on treating households like businesses, teaching kids financial stewardship, and why thinking like your own "family office" can radically change long-term outcomes.

Listeners will come away with a clearer understanding of how to build a mindful, value-driven approach to wealth that supports both personal growth and multigenerational stability. Whether you're raising kids, investing for the first time, or rethinking your relationship with money, this episode offers practical wisdom and grounded inspiration.

• How early memories form unconscious money patterns that affect adult decision-making.

• Why teaching kids autonomy, financial literacy, and values matters more than pushing real estate.

• The importance of transparency around wealth, planning, and tax strategy within families.

• Gino's framework for thinking like a "family office" at any net worth level.

• How real estate fits into long-term legacy building beyond just assets and cash flow.

• Why aligning values, mindset, and financial systems creates more stable generational wealth.

If you enjoy the show, please follow Zen and the Art of Real Estate Investing on Apple Podcasts and leave a rating and review. It helps other listeners discover these conversations and supports the show's growth.

Connect with Gino:

Website: https://barbaro360.com

Youtube: https://www.youtube.com/@barbaro-360

Facebook: https://www.facebook.com/JoinGinosFamily

LinkedIn: https://www.linkedin.com/in/gino-barbaro-03973b4b/

Connect with Jonathan:

Website - www.streamlined.properties

YouTube - www.youtube.com/c/JonathanGreeneRE/videos

Instagram - www.instagram.com/trustgreene

Instagram - www.instagram.com/streamlinedproperties

Zillow - www.zillow.com/profile/streamlinen​j

Bigger Pockets - www.biggerpockets.com/users/jonathangreene

Facebook - www.facebook.com/streamlinedproperties

Email - info@streamlined.properties

This episode was produced by Outlier Audio.

Jonathan Greene welcomes interior designer, real estate investor, and New York State licensed agent Mackenzie Grate to the show for a conversation about design-forward investing, building a rental portfolio from scratch, and choosing the right strategy for your lifestyle. Mackenzie, known as "Mac of All Trades," shares how she shifted from working as an assistant principal to becoming a full-time investor and designer, starting with her first long-term rental in Kingston and eventually expanding into short-term rentals, multifamily properties, and design consulting.

Jonathan and Mackenzie explore mindset, risk tolerance, and how every investor evolves over time. Mackenzie explains why being clear about your investor identity matters, how to avoid overspending on design choices, and why community and local knowledge are essential for success. Her experience highlights the balance between creativity, practicality, and long-term planning.

Listeners will learn what it truly takes to build a sustainable portfolio, from selecting the right first property to managing guest expectations and making design decisions that enhance both functionality and profitability. Mackenzie's combination of design expertise and hands-on investing experience offers thoughtful guidance for anyone looking to build a portfolio that performs.

• How Mackenzie bought her first long-term rental while working full-time in education

• The most common design mistakes investors make and how to avoid unnecessary spending

• Why knowing your investor identity should guide every strategic decision

• How local market knowledge and relationships support short-term rental success

• What realistic scaling looks like for new investors

• Why your first property does not need to be your dream property

If you enjoy the show, please follow Zen and the Art of Real Estate Investing on Apple Podcasts and leave a rating and review. It helps other listeners discover these conversations and supports the show's growth.

Connect with Mackenzie:

Website: www.moatinteriordesigns.com

Instagram: @Mackofalltrades

Connect with Jonathan:

Website - www.streamlined.properties

YouTube - www.youtube.com/c/JonathanGreeneRE/videos

Instagram - www.instagram.com/trustgreene

Instagram - www.instagram.com/streamlinedproperties

Zillow - www.zillow.com/profile/streamlinen​j

Bigger Pockets - www.biggerpockets.com/users/jonathangreene

Facebook - www.facebook.com/streamlinedproperties

Email - info@streamlined.properties

This episode was produced by Outlier Audio.

Jonathan Greene sits down with Chris Grenzig, founder of JAG Property Management and JAG Capital Partners, a vertically integrated multifamily firm focused on Jacksonville and Orlando. Chris walks through his evolution from working at Toro to moving markets, taking on a 16-unit value-add deal, and learning property and construction management by doing. He and Jonathan explore what it's been like to operate through COVID, explosive rent growth, and then a sharp pullback in Florida.

As the conversation unfolds, Chris breaks down how he approached that first 16-unit acquisition, the role his prior asset management experience played, and why local market knowledge became his unfair advantage. He speaks candidly about Florida's recent "perfect storm" of falling rents, rising insurance, and higher interest rates, and how those forces have impacted his portfolio and his investors. Chris and Jonathan also get tactical on out-of-state investing, the limits of BRRRR and flipping in today's environment, and the differences between property management and true asset management.

Listeners will come away with a grounded understanding of what it really looks like to buy, renovate, refinance, and hold in a shifting market—and how to keep investor trust when the numbers don't go as planned. Chris's experience navigating tough cycles in Florida offers real-world lessons on conservative underwriting, staying honest with investors, and building a property management business that serves both accidental landlords and more sophisticated owners.

• How Chris transitioned from working at Toro to moving to Jacksonville and taking on his own 16-unit value-add property

• Why he chose to self-manage and oversee construction on a deal he'd never managed at that level before

• How COVID, rent drops, rising insurance, and interest rate hikes combined into a "perfect storm" for Florida multifamily

• Why local market knowledge and conservative underwriting matter more than ever in today's environment

• The realities and limitations of flipping and BRRRR strategies in higher-rate, higher-cost markets

• What investors should look for in a property manager—and why asset management and property management are not the same thing

If you enjoy the show, please follow Zen and the Art of Real Estate Investing on Apple Podcasts and leave a rating and review. It helps other listeners discover these conversations and supports the show's growth.

Connect with Chris Grenzig:

Website: https://orlandoproperty.management/

Facebook: https://www.facebook.com/chris.grenzig

Instagram: https://instagram.com/chris.grenzig

LinkedIn: https://www.linkedin.com/in/chris-grenzig/

Connect with Jonathan:

Website - www.streamlined.properties

YouTube - www.youtube.com/c/JonathanGreeneRE/videos

Instagram - www.instagram.com/trustgreene

Instagram - www.instagram.com/streamlinedproperties

Zillow - www.zillow.com/profile/streamlinen​j

Bigger Pockets - www.biggerpockets.com/users/jonathangreene

Facebook - www.facebook.com/streamlinedproperties

Email - info@streamlined.properties

This episode was produced by Outlier Audio.