Jake & Gino: Real Estate Investing & Multifamily

Jake & Gino
  • 4.9 (830)
  • INVESTING
  • UPDATED DAILY

Real estate investing, multifamily, and apartment investing—where real estate meets real business ownership. Hosted by investor-entrepreneurs Jake Stenziano and Gino Barbaro, the show goes beyond buying apartments to teach you how to build a durable, well-run real estate business. Each episode blends deal analysis, market insights, leadership lessons, and hard-earned operating experience from owning and managing thousands of units. Whether you’re just starting out or scaling a portfolio, Jake & Gino deliver practical education, honest conversations, and proven frameworks to help you grow cash flow, build systems, and create long-term wealth—without losing sight of family, values, and purpose. Also included under The Jake & Gino umbrella: How To: From real estate underwriting and asset management to organizational structure and owner mindset, How To delivers clear frameworks and actionable guidance for investors who want to build and operate a real estate business with clarity, discipline, and control.

  1. understanding market dynamics in real estate

    10H AGO

    understanding market dynamics in real estate

    Navigating the Current Multifamily Market: Insights from Matt Frazier In this episode, Jake and Gino host Matt Frazier, founder and CEO of Jones Street Investment Partners, to discuss the nuances of the multifamily real estate landscape amid shifting market dynamics. Matt shares his journey, investment strategies, and predictions for the coming year, providing valuable lessons for both new and seasoned investors. Timestamps 00:00 - Introduction and guest background: 25+ years in real estate and finance 02:21 - Current state of the multifamily market and interest rate outlook 03:51 - The fundamental problem: capital deployment and investor psychology 05:39 - Matt's origin story: From venture capital to real estate 07:42 - Early deals: Boston triplexes and market evolution 09:11 - Transition from small assets to larger, institutional-scale properties 12:24 - The regional focus: Northeast's resilience and supply-demand fundamentals 14:14 - Investment criteria: Value-oriented strategies in changing environments 15:48 - How vintage and location influence value-add opportunities 17:55 - What defines true value in multifamily investments? 19:10 - Market risks: Supply constraints, regulatory hurdles, and volatility 20:54 - Rent growth and market dynamics: Northeast vs. Sunbelt 22:48 - Mistakes in dealing with bridge debt and deal selection 24:56 - Advice for new investors entering today’s market 27:37 - Market diversity: Geographic reach from Maine to Virginia 28:23 - Secondary markets: Population thresholds and niche opportunities 30:37 - The psychology of investor appetite in smaller markets 33:33 - How investor psychology affects market segmentation and compression 36:42 - Market fundamentals: The importance of barriers to entry and supply constraints 37:17 - Building a scalable property management operation 39:49 - Challenges and opportunities in property management industry 42:37 - Emerging role of AI and technology in property operations 44:41 - Avoiding pitfalls: personnel and organizational mistakes 45:32 - Bold predictions for 2024: Market thaw and interest rate declines 47:07 - Connecting with Matt and closing remarks   Contact Matt Frazier: Jonesstreet.com Ready to dive into multifamily real estate? Start your journey at wheelbarrowprofits.com For more content and coaching, visit jakeandgino.com We're here to help create real estate entrepreneurs...   About Jake & Gino: Jake & Gino are multifamily investors, operators, and owners who have created a vertically integrated real estate company. They control over $350M in assets under management. Connect with Jake & Gino here --> https://jakeandgino.com. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    49 min
  2. starting a business from scratch? : Here´s exactly what i´d do

    5D AGO

    starting a business from scratch? : Here´s exactly what i´d do

    00:00 Introduction 01:05 Why starting a business today is different 02:30 The mindset you need before launching a business 04:10 Identifying the right opportunity 06:05 Why most people start businesses the wrong way 08:00 The importance of learning before scaling 09:45 Building the right network and partnerships 11:30 Taking action instead of waiting for perfect conditions 13:20 Avoiding common beginner mistakes 15:00 Long-term thinking vs quick money 16:40 Final advice for new entrepreneurs 17:40 Closing thoughts   • Starting a business begins with mindset and clarity • Focus on solving real problems • Build relationships and partnerships early • Take consistent action instead of waiting for perfection • Think long term when building wealth and business More episodes on How To with Gino Barbaro and insights from Gino Barbaro and the Jake & Gino Podcast network. If you're looking to learn more about multifamily real estate investing and how to build long-term wealth, check out the resources, education, and community created by Gino Barbaro and Jake Stenziano. Learn more here:https://wheelbarrowprofits.com We're here to help create real estate entrepreneurs...   About Jake & Gino: Jake & Gino are multifamily investors, operators, and owners who have created a vertically integrated real estate company. They control over $350M in assets under management. Connect with Jake & Gino here --> https://jakeandgino.com. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    18 min
  3. From Zero to $694M in Real Estate Development | Evan Holladay

    MAR 9

    From Zero to $694M in Real Estate Development | Evan Holladay

    In this episode of the Jake & Gino Podcast, hosts Jake Stenziano and Gino Barbaro sit down with real estate developer and investor Evan Holladay. In this conversation, Evan shares his journey into real estate development, the challenges of breaking into the industry, and the key lessons he learned while scaling large projects. He also explains how aspiring developers can get started, what it really takes to succeed in this space, and how real estate development can become a powerful path to building long-term wealth. 00:00 Intro 01:12 Introducing Evan Holladay 03:05 Evan’s Background and How He Got Into Real Estate 07:18 First Challenges Breaking Into Development 11:42 Understanding Affordable Housing Development 16:05 How Real Estate Developers Actually Make Money 20:34 The Complexity of Development Deals 24:10 Lessons From Leading $694M in Projects 28:20 How Beginners Can Enter Real Estate Development 32:15 Common Mistakes New Developers Make 36:05 Workforce & Affordable Housing Opportunities 40:10 Mentoring the Next Generation of Developers 43:20 Advice for Aspiring Real Estate Developers 46:10 Final Thoughts and Where to Connect With Evan 48:34 Outro Beyond development, Evan is passionate about mentorship and education. Through programs like Affordable Development Mastery, he helps guide the next generation of real estate developers looking to enter the affordable housing space. Connect with Evan Holladay 🌐 Affordable Development Masteryhttps://www.affordabledevelopmentmastery.com/ 📸 Instagramhttps://www.instagram.com/evanholladay/ 💼 LinkedInhttps://www.linkedin.com/in/evanholladay/Join the premiere multifamily community www.wheelbarrowprofits.com 🎧 Listen to more episodes of the Jake & Gino Podcast for insights on real estate investing, business, and wealth building. We're here to help create real estate entrepreneurs...   About Jake & Gino: Jake & Gino are multifamily investors, operators, and owners who have created a vertically integrated real estate company. They control over $350M in assets under management. Connect with Jake & Gino here --> https://jakeandgino.com. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    49 min
  4. How To Create Multiple Streams of Revenue - How To Show

    MAR 4

    How To Create Multiple Streams of Revenue - How To Show

    In this episode of the Jake and Gino Podcast – How To Show, we discuss how to create multiple streams of revenue without sacrificing focus or stability. True growth doesn’t come from chasing opportunities. It comes from mastering your core business, building repeatable systems, and expanding strategically. Timestamps 00:00 Introduction 02:10 The Truth About Multiple Income Streams 05:05 Why Most Entrepreneurs Diversify Too Early 08:20 The Importance of a Strong Foundation 11:40 Active vs Leveraged Revenue Explained 14:50 Signs You’re Ready to Expand 17:30 Systems Create Scalable Growth 20:10 Avoiding Shiny Object Syndrome 22:30 A Smarter Approach to Long-Term Growth 23:40 Closing Thoughts If you’re ready to grow inside a proven multifamily framework, join our premier community: 👉 www.wheelbarrowprofits.com Learn more about Jake & Gino here: 👉 https://jakeandgino.com We're here to help create real estate entrepreneurs...   About Jake & Gino: Jake & Gino are multifamily investors, operators, and owners who have created a vertically integrated real estate company. They control over $350M in assets under management. Connect with Jake & Gino here --> https://jakeandgino.com. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    24 min
  5. Navigating the Affordable Housing Landscape

    MAR 2

    Navigating the Affordable Housing Landscape

    In this episode, Jake Stenziano and Gino Barbaro sit down with Evan Holladay, a developer focused on affordable housing. Evan shares how he broke into the industry, the realities of managing complex development projects, and the critical role strong partnerships play in bringing deals to life. The conversation explores the growing demand for affordable housing in the U.S., the financial structure behind these projects, including the use of tax credits, and the many layers involved in navigating approvals and construction. Evan also offers practical advice for investors and developers looking to enter the space while creating meaningful, community-focused impact. Chapters: 00:00 Introduction and Guest Introduction 00:48 Evan's Journey into Affordable Housing 05:09 The Development Process and Challenges 10:28 Understanding Affordable Housing and Tax Credits 15:55 The Buy Right, Operate, Exit Framework 21:11 Partnerships and Risks in Development 22:52 Future of Affordable Housing Development 25:09 Uncovering the Hidden Opportunities in Development 26:54 Financial Rewards and Developer Fees 29:26 Understanding the Long-Term Benefits and Risks 31:05 Navigating the Complexities of Affordable Housing 34:28 Scaling and Systematizing Development Projects 38:38 Lessons Learned from Development Challenges 41:09 Future Opportunities in Affordable Housing 43:02 Logo-animation-JG-New Intro-Sanddunes.mp4   We're here to help create real estate entrepreneurs...   About Jake & Gino: Jake & Gino are multifamily investors, operators, and owners who have created a vertically integrated real estate company. They control over $350M in assets under management. Connect with Jake & Gino here --> https://jakeandgino.com. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    43 min
  6. ACTIVE VS PASSIVE REAL ESTATE INVESTING: Which one is right for you?

    FEB 25

    ACTIVE VS PASSIVE REAL ESTATE INVESTING: Which one is right for you?

    Are you investing in real estate the right way to achieve your financial goals?  There are two ways to invest in real estate: 👉 Active 👉 Passive But here’s the real question — are you truly generating passive income, or just hoping you will? Many investors jump into deals without fully understanding the risks, the operator, the numbers, or the exit strategy. Real estate can create life-changing wealth — but only if you understand how the game works. If you're unsure whether active or passive investing is the right fit for your goals, time, and capital, we’re here to help. 📅 Book a strategy call with our team today and gain clarity on the best path forward. Your clarity today determines your wealth tomorrow. 🔗 Learn more and access additional resources:https://jakeandgino.com/ We're here to help create real estate entrepreneurs...   About Jake & Gino: Jake & Gino are multifamily investors, operators, and owners who have created a vertically integrated real estate company. They control over $350M in assets under management. Connect with Jake & Gino here --> https://jakeandgino.com. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    20 min
  7. From Flipping to Multifamily: A Journey

    FEB 23

    From Flipping to Multifamily: A Journey

    In this episode, Jake and Gino welcome investor Axel Ragnarsson for an in-depth conversation on building and sustaining success in real estate. Axel reflects on his path from small entrepreneurial ventures to owning multifamily properties, underscoring the importance of long-term thinking, disciplined execution, and surrounding yourself with the right people. The discussion covers market shifts, operational efficiency, financing approaches, and how technology is reshaping property management. Axel also shares practical lessons on overcoming today’s market challenges, offering actionable guidance for investors at every stage of their journey. Chapters: 00:00 Introduction  01:05 The Shift in Real Estate Investing 03:08 Axel's Journey into Real Estate 05:12 Transitioning from Flipping to Long-Term Investing 09:52 Understanding Deal Criteria and Value-Add Opportunities 13:37 Financing Strategies for Multifamily Properties 18:47 Operational Excellence in Property Management 26:21 The Importance of Exit Strategies 28:56 Challenges in Real Estate Investing 31:01 Wrap-Up and Key Takeaways 55:02 Logo-animation-JG-New Intro-Sanddunes.mp4     We're here to help create real estate entrepreneurs...   About Jake & Gino: Jake & Gino are multifamily investors, operators, and owners who have created a vertically integrated real estate company. They control over $350M in assets under management. Connect with Jake & Gino here --> https://jakeandgino.com. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    55 min
  8. What’s Really Holding Back Your Business?

    FEB 18

    What’s Really Holding Back Your Business?

    In this conversation, Gino Barbaro explores the behavioral side of business coaching—an area he believes is often ignored. While most coaching programs focus on strategies, systems, and models, Gino argues that real success is driven by the beliefs, habits, and emotional patterns operating beneath the surface. Drawing from his experience in both the restaurant and real estate industries, he reflects on how early family influences and childhood experiences shaped his mindset around money and risk. Gino emphasizes the importance of combining practical business strategy with deep behavioral awareness, advocating for a more holistic approach that addresses both execution and mindset to create lasting growth and meaningful success. We're here to help create real estate entrepreneurs...   About Jake & Gino: Jake & Gino are multifamily investors, operators, and owners who have created a vertically integrated real estate company. They control over $350M in assets under management. Connect with Jake & Gino here --> https://jakeandgino.com. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    19 min
See All (1.3K)

Hosts & Guests

4.9
out of 5
830 Ratings

About

Real estate investing, multifamily, and apartment investing—where real estate meets real business ownership. Hosted by investor-entrepreneurs Jake Stenziano and Gino Barbaro, the show goes beyond buying apartments to teach you how to build a durable, well-run real estate business. Each episode blends deal analysis, market insights, leadership lessons, and hard-earned operating experience from owning and managing thousands of units. Whether you’re just starting out or scaling a portfolio, Jake & Gino deliver practical education, honest conversations, and proven frameworks to help you grow cash flow, build systems, and create long-term wealth—without losing sight of family, values, and purpose. Also included under The Jake & Gino umbrella: How To: From real estate underwriting and asset management to organizational structure and owner mindset, How To delivers clear frameworks and actionable guidance for investors who want to build and operate a real estate business with clarity, discipline, and control.

Information

You Might Also Like