Money Behind the Deal

Michael Gabriel
  • 5.0 (2)
  • Investing

Money Behind the Deal takes investors beyond the headlines and into the real numbers, strategies, and financing decisions that make deals happen. Each episode features honest conversations with investors, lenders, brokers, developers, and industry professionals who break down real deals, loan products, challenges, mistakes, and lessons learned along the way. From DSCR loans and private money to fix-and-flips, multifamily, commercial real estate, and creative financing, this podcast helps investors better understand how deals are structured, funded, and brought across the finish line. No hype. No confusing industry talk. Just practical conversations designed to help you make smarter decisions, avoid costly mistakes, and understand the money behind the deal.

Episodes

  1. Oct 10

    300+ Flips; 1 Mistake

    In this conversation, Mark Sestilio shares his extensive experience in real estate, detailing his journey from wholesaling to flipping over three hundred properties. He emphasizes the importance of teamwork, learning from mistakes, and the value of retaining properties for long-term success. In this conversation, Mark Sestilio reflects on his journey in real estate, discussing past mistakes and current strategies. He emphasizes the importance of focusing on multifamily investments and explores creative financing options for generating income. Takeaways Teamwork drives successLearning from mistakes is crucial Learn from past mistakesFocus on multifamily investments Chapters 00:00 The Journey into Real Estate03:01 First Deals and Partnerships06:06 Scaling the Business08:50 Lessons from Bad Deals12:13 The Importance of Team Dynamics15:02 Reflections on Past Mistakes17:53 The Value of Retaining Properties22:29 Reflecting on Past Decisions27:30 Current Focus on Multifamily Investments30:55 Strategies for Starting Over36:30 Creative Financing and Lease Options

  2. Sep 29

    How a $17,000 Deal Turned Into $83,000 in 35 Days

    In this conversation, Michael and Taylor discuss the challenges of parenting, particularly when it comes to allowing children to take risks. They also delve into Taylor's journey in real estate, sharing insights on his first successful deal and current strategies in the market. In this conversation, Taylor Walls discusses his current real estate strategies, emphasizing the importance of acquisition and the shift towards multifamily investments. He shares valuable advice for new investors, the significance of personal connections, and the hustle required to succeed in the real estate market. Takeaways Fatherly advice on safetyImportance of critical thinking Focus on acquisition strategiesEmbrace risk and ask questions Chapters 00:00 Navigating Parental Concerns05:59 Taylor's Journey into Real Estate12:07 The First Deal: A Unicorn Experience19:55 Current Strategies in Real Estate25:32 Current Real Estate Strategies29:25 Advice for New Investors33:31 Leveraging Resources for Success39:07 The Importance of Door Knocking45:00 Understanding ARV and Investor Needs49:36 The Hustle Behind Real Estate Success

  3. Sep 14

    Why He Moved to Cleveland Blind to Build a $10 Million Net Worth

    What does a real estate portfolio need to look like to grow your net worth from $2.5 million to $10 million? In this episode, Gualter Amarelo joins Michael Gabriel to break down the deal math, investment strategy, and scaling principles he uses to buy bigger properties, create equity, and continuously grow his real estate portfolio. Gualter moved to Cleveland without knowing the market, but he had one clear goal: find deals with enough upside to change his family’s financial future. He explains how he looks for roughly a 20% discount at purchase, then targets another 20% in value-add opportunities. Through renovations, rent growth, refinancing, and mortgage paydown, some of his properties have reached 40% to 50% equity in just a few years. In this conversation, you'll learn: • Why Gualter doesn't buy properties with the intention of holding them forever • How his “pyramiding” strategy helps him trade smaller properties for larger multifamily assets • Why he now refuses to buy anything under 80 units • The acquisition rules he follows before considering a property • Why he stays within five minutes of his team • Why he avoids studios and one-bedroom units • How he evaluates whether existing tenants can support a property's mortgage • Why newer investors should talk to a mortgage broker early • Why buying the smallest deal you can afford today may beat waiting years for the “perfect” opportunity • How speed and relationships can give investors an advantage when deals hit the market Gualter also shares how he built his network from scratch, turned early relationships into capital partnerships, and established credibility by simply getting his first deal done. And if he had to start completely over? He explains exactly how he would approach the challenge of having little money, no credit, and only 30 days to find 200 doors. This episode is for real estate investors who want to think bigger, move faster, build equity, and create a portfolio that scales by design instead of by accident.

  4. Aug 24

    Why Most Fix-and-Flip Deals Fail Before Funding

    The conversation covers Brett Fair's background in lending, his experience with fix and flip loans, and the challenges and strategies involved in financing real estate deals. It also delves into the importance of teamwork, borrower responsiveness, and the key factors for successful real estate investments. The conversation covers the importance of customer service, risk assessment, and myths in real estate lending. It also delves into the significance of realistic expectations and the value of problem-solving in the lending process. Takeaways Teamwork is crucial in real estate financing and involves collaboration between the lender, broker, and borrower.Borrowers need to be financially prepared with reserves and a solid credit score before seeking financing for real estate investments. Customer service and coaching are key to retaining repeat borrowers.Realistic expectations and problem-solving are crucial in the lending process. Chapters 00:00 Introduction and Lending Products01:40 Brett Fair's Background and Career Journey03:23 Challenges in Real Estate Financing04:32 Teamwork and Borrower Responsiveness06:40 Investor Struggles and Financing Considerations09:38 Dealing with Tough Deals and Creative Approaches13:33 Key Factors for Successful Real Estate Investments18:11 Working with First-Time Investors19:29 The Importance of Customer Service20:06 Risk Assessment in Real Estate Lending21:01 Realistic Expectations and Myths in Lending23:02 The Value of Problem-Solving in Lending29:09 The Significance of Repeat Borrowers

  5. Aug 20

    24 Hours to Foreclosure

    A real estate crisis unfolds as an investor is faced with an urgent situation involving an elderly lady at risk of losing her home to auction. The investor explores various solutions, weighs options, and strategizes a financial commitment to resolve the crisis. The final negotiations and decision-making process determine the fate of the property. Takeaways Urgency in real estate investingImportance of exploring multiple solutions Chapters 00:00 Urgent Real Estate Crisis03:09 Exploring Solutions05:30 Options and Decision Making10:15 Financial Strategy and Commitment13:10 Final Negotiations and Decision

  6. Aug 11

    Never Buy a House Before Checking These 10 Things

    Before buying a property, it's crucial to consider the location and potential issues that cannot be fixed with renovations. This includes evaluating the neighborhood, traffic, flood risks, and the property's marketability. Investors and homebuyers should focus on the right property, financing, and have a clear exit strategy. Takeaways Location is a critical factor in property investment.Consider potential issues that cannot be fixed with renovations. Chapters 00:00 The Importance of Location03:17 Evaluating Neighborhood and Traffic07:43 Assessing Property Characteristics09:35 Avoiding Overpriced Properties10:05 Managing Flood Risks11:26 Understanding Renovations and Inspections14:16 Multiple Property Visits and Neighbor Interaction17:05 Investor's Perspective and Exit Strategy

  7. Jul 27

    Interviewed: How a 20-Year Friend Turned Scam Artist Taught Me the Value of Protecting Your Money

    Most entrepreneurs and marketers focus on the wrong thing — chasing results without truly understanding the human behavior behind success.  In this raw, unfiltered conversation, Michael Gabriel reveals the secrets he’s learned from nearly two decades of navigating the world of marketing, entrepreneurship, and personal growth. From explosive poker nights that launched him into a decade-long career and the lessons learned from high-stakes scams to the importance of protecting your investments and reputation, Michael shares concrete insights that can save you from costly mistakes.  Discover how understanding the psychology of human behavior, identifying who’s a giver versus a taker, and guarding your energy and resources can dramatically alter your success in business and life. You'll uncover: The powerful lesson that "design without results is just art" — and how this mindset can transform your marketing strategy.The true value of aligning with genuine givers and avoiding toxic relationships that drain your energy and growth.The eye-opening story of a scam that cost millions, and the critical lessons on protecting yourself, trusting your instincts, and the importance of airtight contracts.Practical tips to analyze human behavior, recognize red flags, and strengthen your decision-making in any relationship or deal.How resilience, integrity, and continuous learning help you bounce back from setbacks and turn adversity into exponential growth. This episode isn't just about marketing — it's about mastering your mindset, safeguarding your investments, and forging authentic relationships. Perfect for entrepreneurs, business owners, or anyone tired of the noise and ready to focus on what truly matters: results that last, and a life built on integrity. Michael Gabriel is a marketing strategist and entrepreneur known for his results-driven approach and deep understanding of human psychology.  He's helped clients grow their businesses, avoid scams, and build sustainable legacy wealth. Get ready to see your business—and your life—with new clarity. When you understand who you're really dealing with, your success becomes inevitable.

  8. Jul 23

    No Money Down : Primary Home

    Michael Gabriel shares a compelling story of helping a young couple achieve their dream of homeownership, despite financial and logistical challenges. His expertise and determination lead to a successful outcome, highlighting the complexities of real estate transactions and the emotional journey of first-time homebuyers. Takeaways Navigating financial hurdles in real estate transactionsThe emotional journey of first-time homebuyers Chapters 00:00 The Dream of Homeownership02:53 Navigating Financial Hurdles06:08 The Complexity of Closing Costs09:05 Time Constraints and Real Estate Transactions11:54 Portfolio Loans and Property Sales15:10 Negotiating Closing Delays18:04 Overcoming the Fear of the First Step

  9. Jul 23

    From Zero 2 Closing Deals

    The conversation delves into Tashin Collins' journey as a real estate investor, from his early fascination with real estate to his impactful mission of reentry housing. Tashin shares insights on his first real estate deal, mistakes made, and the importance of serving others. He also provides a 30-day action plan for securing a property with minimal resources. Takeaways Fascination with real estate sparked by history and the desire to own assetsThe journey to the first real estate deal involved mentorships and learning from mistakesThe first real estate deal involved creative financing and a successful wholesale subject-to transactionMistakes and lessons learned include the importance of holding onto profitable propertiesThe bigger mission involves reentry housing and serving marginalized populationsA 30-day action plan for securing a property with minimal resources was outlined by Tashin Collins Chapters 00:00 The Fascination with Real Estate03:01 The Journey to the First Deal07:04 The First Real Estate Deal11:03 Mistakes and Lessons Learned17:03 The Bigger Mission29:14 30-Day Action Plan

  10. Jul 23

    The High Stakes Fight - Multifamily Deal

    Michael Gabriel shares the journey of working on a deal to convert a multifamily unit into a sober living facility and the challenges faced in the process. From lender requirements to appraisal issues, the persistence and commitment to client success shine through in this story. Takeaways Vision and passion drive real estate investmentNavigating lender requirements is crucial for deal success Chapters 00:00 The Vision of a Sober Living Facility01:55 The Challenges of Converting to Condos03:49 Navigating Lender Requirements06:12 The Appraisal Process07:59 The Persistence of Closing the Deal09:52 Negotiating the Appraisal Value11:50 The Final Hurdle and Closing the Deal13:48 The Commitment to Client Success

  • 10 Episodes

Ratings & Reviews

5
out of 5
2 Ratings

About

Money Behind the Deal takes investors beyond the headlines and into the real numbers, strategies, and financing decisions that make deals happen. Each episode features honest conversations with investors, lenders, brokers, developers, and industry professionals who break down real deals, loan products, challenges, mistakes, and lessons learned along the way. From DSCR loans and private money to fix-and-flips, multifamily, commercial real estate, and creative financing, this podcast helps investors better understand how deals are structured, funded, and brought across the finish line. No hype. No confusing industry talk. Just practical conversations designed to help you make smarter decisions, avoid costly mistakes, and understand the money behind the deal.

Information

  • Creator
    Michael Gabriel
  • Years Active
    2026
  • Episodes
    10
  • Rating
    Explicit
  • Copyright
    © 2026 Michael Gabriel
  • Show Website
    Money Behind the Deal