Jake & Gino: Real Estate Investing & Multifamily

Jake & Gino
  • 4.9 (842)
  • 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. 2d ago

    You Still Need a Real Estate Attorney in the Age of AI

    AI can be an incredible tool for organizing your thoughts—but can it replace an experienced real estate attorney? Richard Crouch, a commercial real estate attorney with more than two decades of experience, explains why experience still matters when navigating complex real estate transactions. AI can help review information and suggest language, but it doesn't have the real-world experience of seeing deals go wrong, understanding the practical consequences of contract language, or recognizing the nuances that can create problems later. In commercial real estate, a provision that looks perfectly clear on paper can have very different consequences in practice. That's why having an experienced attorney who understands the business—not just the legal language—can make a major difference. For real estate investors and sponsors, the goal isn't to avoid technology. It's to know where technology can help—and where experience, judgment, and expertise are still essential. Watch the full conversation for more insights on commercial real estate, syndications, investing, legal strategy, and what successful investors need to know before putting capital into a deal. 00:05 - Welcome and introduction of guest Richard Crouch 00:35 - Teasing Richard about attorneys killing deals; asking why he became a lawyer 00:51 - Richard's path to becoming an attorney and entering commercial real estate 01:42 - What Richard loves about commercial real estate compared to litigation 02:20 - Discussing the difficult aspects and fast pace of commercial real estate 04:13 - Discussing AI/ChatGPT, its limits, and the value of a seasoned attorney 06:05 - The evolution of syndications from 2001 to today 08:00 - Impact of capital raisers and market cycles on pricing and valuations 09:01 - Challenges of exiting the market or finding replacement assets 10:05 - Common habits, skills, and disciplines of successful long-term investors 13:16 - Discussion on asset classes (industrial, medical office, multifamily) 14:35 - Current investor pain points, interest rate impacts, and loan covenants 17:30 - Advice for passive investors: warning signs, red flags, and performance metrics 21:14 - Importance of sponsors having skin in the game 22:06 - Value of having an attorney review deal documents before investing 24:10 - Essential legal documents for investors (PPM, Subscription Agreement, Operating Agreement) 25:59 - The three-step framework for passive investors (Jockey, Saddle, Horse) 27:56 - Common misconceptions about legal fees and the complexity of CRE transactions 30:34 - Differences in financing (local bank vs. CMBS loans) and reading the fine print 31:46 - Case study: A deal saved through creative structuring and seller financing 📚 Learn more about Wheelbarrow Profits Looking to invest in multifamily real estate or connect with experienced investors? 👉 https://wheelbarrowprofits.com 👉 bit.ly/zenAI_bpp_jandg 👉www.trudiagnostic.com code JAKEAND GINO. for 20% off 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.

    You Still Need a Real Estate Attorney in the Age of AI

  2. 6d ago

    The Real Reason Your Business Won’t Scale

    What if the biggest thing holding your business back… is you? When a business stops growing, we often look for better strategies, systems, processes, marketing, or sales tactics. But sometimes, the real bottleneck is much more personal: the unconscious behaviors and beliefs of the person running the business. In this episode, Gino Barbaro breaks down four business archetypes that can either limit your growth or help you scale: The key isn't simply identifying your archetype. It's asking yourself three questions: Where does this archetype show up in my business? Is it empowering me or limiting me? What needs to change? As Gino explains, scaling a company isn't only about learning better strategies. At some point, you have to look at yourself, challenge your limiting beliefs and behaviors, and develop the mindset required to lead the company you're trying to build. Your business can only grow as much as you're willing to grow. Watch the full conversation for a deeper look at business archetypes, leadership, mindset, and what may really be standing between you and your next level of growth. 🎁 Free Resource: Understand Your Business Archetype Discover your business archetype and gain a deeper understanding of how you naturally approach your business. Download the free PDF here:https://drive.google.com/file/d/1DG3V... 📚 Learn more about Wheelbarrow Profits Looking to invest in multifamily real estate or connect with experienced investors? 👉 https://wheelbarrowprofits.com 👉 bit.ly/zenAI_bpp_jandg 👉www.trudiagnostic.com code JAKEAND GINO. for 20% off 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.

    The Real Reason Your Business Won’t Scale

  3. Aug 17

    How to Spot Bad Real Estate Deals Before You Lose Your Capital

    Are the days of "go bigger, faster" in real estate over? In this episode of the Jake & Gino Podcast, Jake Stenziano and Gino Barbaro sit down with commercial real estate investor and host of Invest Beyond Multifamily, Ash Patel. Together, they pull back the curtain on why syndicators are losing tens of millions of dollars in the current market cycle, the danger of overpaying for deals based on speculative pro formas, and why cash-on-cash return—not IRR—is the ultimate metric for long-term wealth. Plus, Ash breaks down why retail and suburban office space are quietly offering massive, low-risk returns while everyone else is fighting over multifamily. Timestamps: 00:00 - Introduction: Ash Patel (Invest Beyond Multifamily) 02:18 - The Fall of "Go Bigger, Faster" & Overpaying for Deals 06:37 - Why Big Syndicators Are Losing Millions 10:13 - Red Flags to Look Out For Before Investing with a Syndicator 14:41 - The Truth About Retail: Lowest Vacancy in History 20:03 - Why Buying Blue-Collar Businesses Is Overhyped 25:05 - Cash-on-Cash Return vs. IRR 📚 Learn more about Wheelbarrow Profits Looking to invest in multifamily real estate or connect with experienced investors? 👉 https://wheelbarrowprofits.com 👉 bit.ly/zenAI_bpp_jandg 👉www.trudiagnostic.com code JAKEAND GINO. for 20% off We're here to help create multifamily entrepreneurs... Here's how: Brand New? Visit our website for more resources👉https://jakeandgino.com/ About Jake & Gino Jake & Gino are multifamily investors, operators, and mentors who have created a vertically integrated real estate company. They control over $350M in assets under management. They have created the Jake & Gino Premier Multifamily Community to teach others a simple three-step framework for investing in multifamily real estate. Connect with Jake & Gino on the social media platform you are most active on: https://jakeandgino.com/link-tree/ #RealEstateInvesting #MultifamilyInvesting #CommercialRealEstate #PersonalFinance #passiveincome 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.

    How to Spot Bad Real Estate Deals Before You Lose Your Capital

  4. Aug 12

    What Type of Business Owner Are You?

    What if the biggest problem in your business isn’t marketing, sales, or finance—but the way you think and behave? In this episode, Gino Barbaro explores the concept of business archetypes and how unconscious patterns, beliefs, and emotional responses can influence the way you lead, make decisions, and grow your business. There are 10 different business archetypes, including the Rebel, Warrior, Servant Leader, Gambler, Novice, Inventor, Dictator, Conservator, Entrepreneur, and Master. None of them are inherently good or bad. The key is understanding how each archetype shows up in your behavior—and recognizing when one may be helping you or holding you back. Gino shares personal examples from his restaurant and real estate journey, including how the Conservator and Novice archetypes affected his ability to grow and scale. He also explains how activating the Warrior mindset helped him develop a growth mindset, learn new systems, and move beyond the limitations of his previous experience. Ask yourself: • Which business archetype sounds most like you? • Where has this archetype helped you succeed? • Where has it become a liability? • What behavior do you need to change to take your business to the next level? The goal isn't to become a different person. It's to become more self-aware—so you can recognize the patterns influencing your decisions and consciously choose how you want to respond. Want to discover all 10 business archetypes? Email Gino at Gino@JakeandGino.com to receive the full list and characteristics of each archetype. Watch the full episode to dive deeper into business behavior, leadership, self-awareness, and the mindset required to grow your business. 00:00 – What If the Biggest Problem in Your Business Is You? 00:45 – What Are Business Archetypes? 02:00 – How Unconscious Behaviors Affect Your Business 03:00 – Gino’s Personal Experience With Business Archetypes 05:00 – The Rebel Archetype 07:00 – The Warrior Archetype 08:30 – The Servant Leader Archetype 09:30 – The Gambler Archetype 11:00 – The Novice Archetype 13:00 – The Inventor Archetype 14:30 – How Archetypes Impact Business Decisions 15:30 – The Dictator Archetype 17:00 – The Conservator Archetype 18:30 – The Entrepreneur Archetype 20:00 – The Master Archetype 22:00 – How the Archetypes Work Together 23:00 – 4 Questions to Identify Your Business Archetype 25:00 – What Behaviors Are Holding Your Business Back? 26:30 – Your Business Isn’t the Problem—Your Patterns Are 27:30 – Final Thoughts & Next Episode 🎁 Free Resource: Understand Your Business Archetype Discover your business archetype and gain a deeper understanding of how you naturally approach your business. Download the free PDF here:https://drive.google.com/file/d/1DG3V... 📚 Learn more about Wheelbarrow Profits Looking to invest in multifamily real estate or connect with experienced investors? 👉 https://wheelbarrowprofits.com 👉 bit.ly/zenAI_bpp_jandg 👉www.trudiagnostic.com code JAKEAND GINO. for 20% off 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.

    What Type of Business Owner Are You?

  5. Aug 10

    How to Turn Marketing Into Real Estate Wealth

    What happens when you combine digital marketing with real estate investing? Bryan Driscoll started in digital marketing, working in areas like SEO, e-commerce, and health insurance. After buying his first property from a wholesaler, he realized he could potentially generate those real estate leads himself—and that experiment eventually grew into a marketing business focused on real estate investors. In this episode of the Jake & Gino Podcast, Bryan breaks down how real estate investors can use marketing to find better leads, build their brand, raise capital, and ultimately acquire more real estate. Bryan also explains why one of the biggest problems investors face isn't a lack of tools—it's not taking action. And his approach to real estate is simple: use the income you generate today to build assets that can create wealth for your future. If you're a real estate investor looking to generate more leads, find better deals, build your personal brand, or use AI to improve your marketing, this episode is for you. ⏱️ Timestamps 00:00 Intro & Meet Bryan Driscoll 01:07 Bryan's Real Estate Investing Strategy 01:43 From Digital Marketing to Real Estate Lead Generation 02:49 Why Real Estate Investors Struggle With Marketing 03:48 Who Should Handle Your Leads? 05:04 Outbound vs. Inbound Marketing 05:32 Facebook Ads & Lead Quality 06:56 Facebook Native Leads Explained 08:07 Who Should You Target? Finding Your Ideal Avatar 09:38 Why Website Leads Can Be Higher Quality 10:29 What Should a Real Estate Lead Cost? 11:45 Google Ads vs. Facebook Ads 13:02 How to Get Started With Google PPC 14:39 How to Choose the Right Marketing Agency 16:46 What to Look for in a Marketing Company 18:18 The KPIs Every Investor Should Track 19:15 How Much Should a Real Estate Deal Cost? 20:26 Bryan's First Marketing-Generated Leads 21:58 What's Working in Real Estate Marketing Right Now? 23:39 How Often Should You Adjust Your Facebook Ads? 25:35 Don't Fix What Isn't Broken 27:11 When Should You Hire a Marketing Agency? 27:47 Marketing vs. Real Estate: Which Does Bryan Prefer? 28:03 Using Real Estate to Build Long-Term Wealth 29:23 Why Real Estate Investors Need to Build Their Personal Brand 29:36 Sponsor Break 29:52 How Marketing Helped Build Bryan's Real Estate Portfolio 30:18 How Bryan Built 14 Properties Using the BRRRR Strategy 31:27 Bryan's Long-Term Wealth Strategy 33:30 Marketing for Multifamily Real Estate 35:30 Building Relationships With Property Managers 37:18 Phone, Text & Direct Outreach for Multifamily 39:38 Building an Investor List With Facebook & Google 40:13 How to Turn Social Media Followers Into an Email List 42:07 The Biggest Mistake Real Estate Investors Make 43:24 Building Websites With AI 44:40 The CRM Bryan Recommends 45:25 How to Start Your Marketing Strategy 46:59 Using AI to Find Your Ideal Customer 47:32 AI Tools for Creating Marketing Ads 48:05 The Future of Real Estate Marketing 48:56 Why Your Marketing Message Matters 49:21 Where to Find Bryan Driscoll 📚 Learn more about Wheelbarrow Profits Looking to invest in multifamily real estate or connect with experienced investors? 👉 https://wheelbarrowprofits.com 👉 bit.ly/zenAI_bpp_jandg 👉www.trudiagnostic.com code JAKEAND GINO. for 20% off 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.

    How to Turn Marketing Into Real Estate Wealth

  6. Aug 5

    Which Metric Actually Matters? IRR vs. Cash-on-Cash

    Is a higher IRR always a sign of a better real estate deal? Not necessarily. In this video, Gino Barbaro breaks down one of the most important questions real estate investors need to ask when analyzing a deal: Should you focus on IRR, or should you be looking at cash-on-cash return and yield? IRR (Internal Rate of Return) can be a useful metric for comparing investments, but it relies heavily on future assumptions — including rent growth, expenses, exit cap rates, financing, and the eventual sale of the property. Small changes in those assumptions can dramatically change the projected IRR. That’s why Gino and Jake focus heavily on yield and cash-on-cash returnwhen evaluating their own investments. The bigger lesson? Don’t confuse projected returns with realized wealth. When analyzing a real estate deal, ask yourself: • Would I still buy this property if it never appreciated? • Can the property’s cash flow survive higher interest rates? • How long could the property operate if rents softened? • Will this investment help fund my next acquisition? • Am I buying projected wealth or actual, verifiable income? • Is the higher return worth the additional effort and risk? Gino also introduces another important concept: ROE — Return on Effort. A property with a slightly lower projected return may ultimately be the better investment if it requires less management, has fewer problems, better tenants, stronger fundamentals, and greater long-term potential. 📚 Learn more about Wheelbarrow Profits Looking to invest in multifamily real estate or connect with experienced investors? 👉 https://wheelbarrowprofits.com 👉 bit.ly/zenAI_bpp_jandg 👉www.trudiagnostic.com code JAKEAND GINO. for 20% off 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.

    Which Metric Actually Matters? IRR vs. Cash-on-Cash

  7. Aug 3

    Will AI Replace Property Managers? Here's the Truth

    Artificial Intelligence is changing every industry—but what does that actually mean for property management? In this episode, IT expert Lara Hamilton joins Jake & Gino to break down how AI is already transforming property management operations, software, reporting, maintenance, and customer service. Rather than replacing people, AI is helping teams eliminate repetitive work, reduce operational friction, and spend more time on the tasks that actually generate value. In this conversation, you'll learn: • How AI is improving property management today • Why automation won't replace great employees • The biggest operational bottlenecks hurting property managers • The future of property management software • AppFolio vs. Yardi vs. RealPage • How AI can streamline reporting and business operations • Why human relationships still matter in an AI-driven world • The importance of using AI securely and responsibly • How maintenance teams could become dramatically more efficient with AI • Practical ways operators can begin implementing AI immediately Whether you're a property manager, multifamily investor, business owner, or simply curious about how AI is changing the workplace, this conversation is packed with actionable insights. If you enjoyed this episode, be sure to Like, Subscribe, and hit the Notification Bell so you never miss future interviews with industry leaders. TIMESTAMPS: 00:00 Intro & Meet Lara Hamilton 01:24 What Help Desk Realty Actually Does 03:41 Lara's Journey into IT 06:41 AI, Phone Systems & Customer Support 08:33 Will AI Replace Jobs? 10:23 The Reality of AI Adoption 12:00 How AI Eliminates Operational Friction 13:08 AppFolio vs. Yardi vs. RealPage 14:41 Jake's Vision for Fully Automated Leasing 17:42 Which Property Management Software Is Best? 20:53 How Property Managers Can Start Using AI Today 24:17 The Future of AI in Property Management 25:49 RealPage vs. AppFolio 29:08 Why Maintenance Teams Matter Most 31:11 Jake's AI Body Cam Idea for Maintenance Techs 33:21 AI Leasing Assistants & Chatbots 35:22 Real-World Success Stories 37:14 How to Contact Help Desk Realty 37:45 Final Thoughts: Don't Fear AI—Use It 40:03 Outro 👇 What task would you let AI handle in your business first? Let us know in the comments! 📚 Learn more about Wheelbarrow Profits Looking to invest in multifamily real estate or connect with experienced investors? 👉 https://wheelbarrowprofits.com 👉 bit.ly/zenAI_bpp_jandg 👉www.trudiagnostic.com code JAKEAND GINO. for 20% off 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.

    Will AI Replace Property Managers? Here's the Truth

  8. Aug 1

    The Biggest Lie in Multifamily Investing

    Are you trusting the seller's numbers... or verifying the truth? One of the fastest ways to lose money in multifamily real estate isn't overpaying—it's believing a pro forma that doesn't reflect reality. In this episode, Gino Barbaro explains why experienced investors never rely solely on seller projections and how verifying operating expenses can be the difference between a profitable investment and financial disaster. You'll learn why so many multifamily deals fail, which expenses are commonly underestimated, and how professional investors build conservative underwriting models that protect both their capital and their investors. In this video you'll learn: ✔ Why seller pro formas can be dangerously misleading ✔ The difference between revenue growth and true profitability ✔ The most commonly underestimated operating expenses ✔ How to verify insurance, taxes, payroll, utilities, maintenance, and property management costs ✔ Why experienced investors create their own pro forma instead of trusting the broker's ✔ Red flags that can expose a bad apartment deal before you buy ✔ How to evaluate deals based on cash flow—not hope ✔ Why reducing expenses often creates more value than increasing income Whether you're investing in your first apartment building or already own a portfolio, this episode will help you underwrite smarter, avoid costly mistakes, and make better investment decisions in today's market. One of the biggest lessons from this episode: A seller's pro forma tells a story. Verified expenses tell the truth. If you want to become a disciplined multifamily investor, this conversation is essential. 📚 Learn more about Wheelbarrow Profits Looking to invest in multifamily real estate or connect with experienced investors? 👉 https://wheelbarrowprofits.com 👉 bit.ly/zenAI_bpp_jandg 👉www.trudiagnostic.com code JAKEAND GINO. for 20% off 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.

    The Biggest Lie in Multifamily Investing
See All (1.4K)

Hosts & Guests

4.9
out of 5
842 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