First Deal Podcast

Keith Gillispie
  • 0.0 (0)
  • Investing

Your first deal is the hardest - until you know what actually works. I'm Keith Gillispie, Marine veteran, real estate investor across 34 states, and coach to 400+ students with a 99.3% success rate. Each episode delivers the playbook I wish I had when I started: creative financing strategies, private capital raising, and systems that don't require perfect credit or massive cash reserves. Plus, we bring in questions from our listeners and answer them live! So if you're stuck, you're getting real solutions, not generic advice.

  1. 1 day ago

    #34 - How To Know When You're Ready To Invest In Real Estate (The Harsh Truth)

    Keith gets honest about the parts of real estate investing that never make it into the books — the emotional weight, the relentless learning curve, and the reality that most people aren't built for entrepreneurship. Then he breaks down the single family vs. multifamily debate and ends with a blunt answer to the question every new investor secretly asks: how do I know when I'm actually ready? Takeaways Learn how real estate and entreupenuerhsip will push you to your limits (and what you can do to overcome them).Discover what it really takes to survive and thrive in this industry.Understand how your feelings betray you and sabatoge your success. Chapters 00:00 Introduction00:48 Accidental Live Episode01:44 The Harsh Realities of Real Estate06:10 Mindset and Education for Success09:33 Building a Strong Foundation12:06 Navigating the Real Estate Landscape18:00 Knowing When You're Ready to Invest20:50 Outro 📜FREE Purchase & Sales Agreement: https://go.reiautomated.io/strongest-psa-lm  📊FREE Deal Analyzer + Repair Estimator: https://go.reiautomated.io/deal-analyzer     📃FREE Joint Venture Agreement: https://go.reiautomated.io/jv-agreement-flm  🏠FREE Facebook Community: https://www.facebook.com/groups/realestateinvestingandwholesaling   🧑🏻‍💻FREE COURSE (watch 5 min first): https://playbook.reiautomated.io/?source=Keith&campaign=OFC  🌟CLIENT RESULTS: https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb  WHAT WE OFFER: https://youtu.be/JbV0LqjdhJ8  SOCIALS Instagram: https://www.instagram.com/keithg_rei/  Facebook: https://www.facebook.com/Keith.Gillispie

    21 min

  2. 5 days ago

    #33 - How You Can Get Into Real Estate Investing With Almost Zero Dollars

    Keith tackles four foundational questions every beginner real estate investor eventually asks: Is house hacking actually worth it? What do you do with $100K starting out… and what if you have nothing? How many units does it take to go full-time? And should you buy your first home or keep renting and invest elsewhere? His answers are direct, occasionally controversial, and grounded in a decade of real-world experience. Takeaways House hacking can be a viable option for beginners in real estate investing.Starting with limited funds is possible, but it requires time, energy, and mental bandwidth.Family values and personal priorities should guide financial decisions. Chapters 00:00 Introduction00:37 Cold Open01:31 The Concept of House Hacking04:34 House Hacking: Pros and Cons05:24 Starting with $100,000: Investment Strategies08:33 Getting into Real Estate with No Money11:51 Exploring Key Themes and Insights12:07 How Many Units for Full-Time Income?20:41 Reflecting on Past Real Estate Decisions22:39 Buying vs. Renting: Family First27:24 Building Long-Term Success in Real Estat 📜FREE Purchase & Sales Agreement: https://go.reiautomated.io/strongest-psa-lm  📊FREE Deal Analyzer + Repair Estimator: https://go.reiautomated.io/deal-analyzer     📃FREE Joint Venture Agreement: https://go.reiautomated.io/jv-agreement-flm  🏠FREE Facebook Community: https://www.facebook.com/groups/realestateinvestingandwholesaling 🧑🏻‍💻FREE COURSE (watch 5 min first): https://playbook.reiautomated.io/?source=Keith&campaign=OFC  🌟CLIENT RESULTS: https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb  WHAT WE OFFER: https://youtu.be/JbV0LqjdhJ8  SOCIALS Instagram: https://www.instagram.com/keithg_rei/  Facebook: https://www.facebook.com/Keith.Gillispie

    28 min

  3. 26 Jun

    #32 - How To Go From The Corporate Grind to Financial Freedom with Michael B.

    Keith sits down with Houston-based real estate investor Michael H. to trace his full journey — from traveling every week for a soul-draining corporate telecom job to building a portfolio across multiple strategies. Michael shares why the BRRRR method no longer works in his market, how he stumbled into mobile home land packages with 60–90K profit margins, and what he actually believes generational wealth means for his kids. Guests Michael Hoang is a real estate investor, operator, and agent Where to find Michael @michaelbesomeone across all platforms (YouTube, Instagram, Threads, etc.) Takeaways Transitioning from a corporate job to real estate successThe significance of house hacking and adapting to market changes Mobile home land package deals offer high margins and simplified development processes.Success is defined by the ability to do what you want, when you want, with the people you want. Chapters 00:00 Michael's Journey into Real Estate06:41 The House Hacking Experience12:40 Challenges with the BRRRR Method15:46 Adapting to Changing Real Estate Strategies16:59 Exploring Land Home Packages18:33 Transitioning to Multifamily Investments20:25 The Evolution of Mobile Homes25:08 Remote Real Estate Management30:22 Defining Personal Success33:16 Building a Legacy Beyond Wealth39:37 Building Long-Term Success in Real Estate 📜FREE Purchase & Sales Agreement: https://go.reiautomated.io/strongest-psa-lm  📊FREE Deal Analyzer + Repair Estimator: https://go.reiautomated.io/deal-analyzer    📃FREE Joint Venture Agreement: https://go.reiautomated.io/jv-agreement-flm  🏠FREE Facebook Community: https://www.facebook.com/groups/realestateinvestingandwholesaling   🧑🏻‍💻FREE COURSE (watch 5 min first): https://playbook.reiautomated.io/?source=Keith&campaign=OFC  🌟CLIENT RESULTS: https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb  WHAT WE OFFER: https://youtu.be/JbV0LqjdhJ8  SOCIALS Instagram: https://www.instagram.com/keithg_rei/  Facebook: https://www.facebook.com/Keith.Gillispie

    40 min

  4. 24 Jun

    #31 - Cold Call Scripts That Work, The "If vs When" Trap & How Keith Traded a Truck For a House

    Keith breaks down the single most common mistake that kills deals in negotiations, shares his exact cold-call opening line, and explains why the word "if" is quietly sabotaging your seller conversations. Plus a real story about a seller who wouldn't budge on price — until Keith stopped trying to get him money and got him the two things the seller actually desired.  Takeaways The #1 mistake that kills deals in negotiationHow language shapes the battlefield of seller negotiationsWhy you should stop making offers Chapters 00:00 Introduction00:44 Negotiation Pitfalls in Real Estate02:34 The Art of Cold Calling06:41 Utilizing Technology in Real Estate Calls10:30 Effective Call Scripts and Approaches15:31 Understanding Seller Motivations20:59 Creative Solutions in Negotiation24:58 Conclusion and Key Takeaways27:02 Building Long-Term Success in Real Estate 📜FREE Purchase & Sales Agreement: https://go.reiautomated.io/strongest-psa-lm  📊FREE Deal Analyzer + Repair Estimator: https://go.reiautomated.io/deal-analyzer    📃FREE Joint Venture Agreement: https://go.reiautomated.io/jv-agreement-flm  🏠FREE Facebook Community: https://www.facebook.com/groups/realestateinvestingandwholesaling   🧑🏻‍💻FREE COURSE (watch 5 min first): https://playbook.reiautomated.io/?source=Keith&campaign=OFC  🌟CLIENT RESULTS: https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb  WHAT WE OFFER: https://youtu.be/JbV0LqjdhJ8  SOCIALS Instagram: https://www.instagram.com/keithg_rei/  Facebook: https://www.facebook.com/Keith.Gillispie

    27 min

  5. 19 Jun

    #30 - How To Handle Difficult Sellers And The "Three Offer" Myth

    Dayton and Keith go deep on the human side of real estate investing — what to do when a seller call goes sideways, why the popular "present three offers" strategy is actually a mistake, and Keith's framework for closing deals without ever making an offer himself. This episode is less about numbers and more about psychology, communication, and process. Takeaways Why presenting three offers is a waste of your timeUnderstanding seller psychologyWhy empathy is the most important sales skill of all Chapters 00:00 Introduction01:42 Navigating Difficult Seller Calls06:39 Understanding Seller Emotions and Reactions11:39 The Importance of Empathy in Sales12:49 Presenting Offers: The Three-Offer Debate21:00 The Perfect Presentation: Closing Deals Effectively35:12 Building Long-Term Success in Real Estate 📜FREE Purchase & Sales Agreement: https://go.reiautomated.io/strongest-psa-lm  📊FREE Deal Analyzer + Repair Estimator: https://go.reiautomated.io/deal-analyzer    📃FREE Joint Venture Agreement: https://go.reiautomated.io/jv-agreement-flm  🏠FREE Facebook Community: https://www.facebook.com/groups/realestateinvestingandwholesaling   🧑🏻‍💻FREE COURSE (watch 5 min first): https://playbook.reiautomated.io/?source=Keith&campaign=OFC  🌟CLIENT RESULTS: https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb  WHAT WE OFFER: https://youtu.be/JbV0LqjdhJ8  SOCIALS Instagram: https://www.instagram.com/keithg_rei/  Facebook: https://www.facebook.com/Keith.Gillispie

    36 min

  6. 16 Jun

    #29 - How To Overcome A Competing Cash Offer With "The Seedling Method"

    Dayton tries to stump Keith with the "one magic question" myth — and Keith explains why no single question makes a seller want to sell to you, but a specific negotiation sequence will move more money than anything else. Plus: how to overcome a competing cash offer using the "Seedling" method, and Keith's three-wave defense for stopping family members, attorneys, and other third parties from killing a deal after the contract is signed. Takeaways The negotiation sequence to turn a skeptical seller into a raving fanThe power of negotiation questionsHow to deal with third parties trying desperately to rob ypu of your rewards Chapters 00:00 Introduction00:55 The Power of Questions in Real Estate Negotiation07:37 Establishing Trust and Process with Sellers16:44 Handling Competing Offers and Seller Doubts24:06 Managing Third-Party Influences in Real Estate Deals31:53 Building Long-Term Success in Real Estate 📜FREE Purchase & Sales Agreement: https://go.reiautomated.io/strongest-psa-lm  📊FREE Deal Analyzer + Repair Estimator: https://go.reiautomated.io/deal-analyzer    📃FREE Joint Venture Agreement: https://go.reiautomated.io/jv-agreement-flm  🏠FREE Facebook Community: https://www.facebook.com/groups/realestateinvestingandwholesaling   🧑🏻‍💻FREE COURSE (watch 5 min first): https://playbook.reiautomated.io/?source=Keith&campaign=OFC  🌟CLIENT RESULTS: https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb  WHAT WE OFFER: https://youtu.be/JbV0LqjdhJ8  SOCIALS Instagram: https://www.instagram.com/keithg_rei/  Facebook: https://www.facebook.com/Keith.Gillispie

    32 min

  7. 11 Jun

    #28 - Finally Putting An End To The Great Wholesale Vs. Flipping Debate?

    Dayton and Keith tackle three meaty topics: whether investors should chase assignment fees or take title for bigger profits, when buyer loyalty actually matters (and when it doesn't), and the three deal structures that investors think are safe — but often aren't. Keith pulls no punches on the legal landmines hiding inside sub-2, wholesaling assignments, and sub-3 transactions. Takeaways Assignment Fees vs. Taking Title: Which is the Smarter Play?Buyer Loyalty: When It Matters and When It Doesn'tThe 3 Most Dangerous Deal Structures Right Now as of This Recording Chapters 00:00 Introduction00:44 Wholesaling vs. Flipping: The Great Debate06:48 Navigating Nationwide vs. Local Business Models12:46 Understanding Sub 2 Transactions and Their Risks18:54 Legislation and the Future of Wholesaling26:21 Building Long-Term Success in Real Estate 📜FREE Purchase & Sales Agreement: https://go.reiautomated.io/strongest-psa-lm  📊FREE Deal Analyzer + Repair Estimator: https://go.reiautomated.io/deal-analyzer    📃FREE Joint Venture Agreement: https://go.reiautomated.io/jv-agreement-flm  🏠FREE Facebook Community: https://www.facebook.com/groups/realestateinvestingandwholesaling   🧑🏻‍💻FREE COURSE (watch 5 min first): https://playbook.reiautomated.io/?source=Keith&campaign=OFC  🌟CLIENT RESULTS: https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb  WHAT WE OFFER: https://youtu.be/JbV0LqjdhJ8  SOCIALS Instagram: https://www.instagram.com/keithg_rei/  Facebook: https://www.facebook.com/Keith.Gillispie

    27 min

  8. 4 Jun

    #27 - Building A Social Presence For Lead Gen, And Why Speed To Lead Matters

    Dayton and Keith break down three high-leverage topics for real estate investors: how to find the most motivated sellers using hyper-specific lists, why speed to lead is the single most important metric in your business, and how to choose the right deal structure for any situation. Keith also shares a behind-the-scenes look at the suite of tools he's building to help investors do more deals in less time. Takeaways Real estate as a long-term wealth-building strategyImportance of speed to lead in real estate investingLeveraging social media for lead generation Chapters 00:00 Introduction00:44 Real Estate Investing Strategies03:33 Leveraging Technology in Real Estate06:38 The Importance of Speed to Lead09:35 Transitioning from Outbound to Inbound Marketing12:53 Building a Social Media Presence for Lead Generation15:45 Understanding Deal Structures and Strategies35:05 Building Long-Term Success in Real Estate 📜FREE Purchase & Sales Agreement: https://go.reiautomated.io/strongest-psa-lm  📊FREE Deal Analyzer + Repair Estimator: https://go.reiautomated.io/deal-analyzer    📃FREE Joint Venture Agreement: https://go.reiautomated.io/jv-agreement-flm  🏠FREE Facebook Community: https://www.facebook.com/groups/realestateinvestingandwholesaling   🧑🏻‍💻FREE COURSE (watch 5 min first): https://playbook.reiautomated.io/?source=Keith&campaign=OFC  🌟CLIENT RESULTS: https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb  WHAT WE OFFER: https://youtu.be/JbV0LqjdhJ8  SOCIALS Instagram: https://www.instagram.com/keithg_rei/  Facebook: https://www.facebook.com/Keith.Gillispie

    35 min
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About

Your first deal is the hardest - until you know what actually works. I'm Keith Gillispie, Marine veteran, real estate investor across 34 states, and coach to 400+ students with a 99.3% success rate. Each episode delivers the playbook I wish I had when I started: creative financing strategies, private capital raising, and systems that don't require perfect credit or massive cash reserves. Plus, we bring in questions from our listeners and answer them live! So if you're stuck, you're getting real solutions, not generic advice.

Information

  • Creator
    Keith Gillispie
  • Years Active
    2k
  • Episodes
    34
  • Rating
    Clean
  • Copyright
    © 2026 Keith Gillispie