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. 18h ago

    #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

  2. 3d ago

    #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

  3. Jun 11

    #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

  4. Jun 4

    #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

  5. Jun 3

    #26 - Learn How To Stand Out In A Crowded Market And The Lifespan Of Lead Sources

    Dayton and Keith cover real estate investment strategies, lead generation, and ethical considerations in real estate marketing. It emphasizes the importance of planning for the future and the significance of multi-touch marketing approaches. Takeaways Real estate is a simple way to build long-term wealthLead sources require consistent effort and multi-touch marketingPlanning for the future is crucial for personal and financial well-being Chapters 00:00 Introduction00:44 Reconnecting After a Break03:45 The Lifespan of Lead Sources in Real Estate06:56 Strategies to Stand Out in a Crowded Market12:39 Engagement Metrics and Multi-Channel Marketing18:56 Generational Differences in Communication Preferences24:58 Ethics in Real Estate Marketing and Lead Generation31:02 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

    31 min

  6. May 28

    #25 - The Mandatory Clauses Essential To Investor Protection In Any Deal

    The conversation covers the key clauses that investors need for protection in almost any scenario and the innovative deal structuring strategies in the real estate industry. It delves into the importance of real estate as a long-term wealth-building strategy and explores the use of novations as a go-to deal structure in the current market environment. Takeaways Real estate as a wealth-building strategyInnovative deal structuring in real estate Chapters 00:00 Introduction00:44 Keith Can't Choose A Color01:46 Unusual Lead Generation Strategies06:50 The Power of Curiosity in Marketing12:50 Emerging Deal Structures: Novations19:03 Key Clauses in Contracts for Investors29:27 The Skill of Real Estate Investing29:28 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

    30 min

  7. May 27

    #24 - The AI Takeover Of Real Estate Investing

    The conversation covers the impact of AI on real estate and marketing. It delves into the significance of real estate as a long-term wealth-building method and the ways in which AI is transforming the real estate industry and marketing practices. Takeaways Real estate as a wealth-building strategyThe impact of AI on real estate and marketing Chapters 00:00 Introduction00:44 The Impact of AI on Investment Strategies11:45 Creative Financing in Real Estate18:39 Improving Seller Communication20:16 Challenging Conventional Wisdom in Negotiation25:46 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

    26 min

  8. May 24

    #23 - Learn To Multiply Your Profits With Different Financing Options

    Dayton and Keith pull back the curtain on the gritty challenges investors face when chasing funding... and reveal the creative, battle-tested lead generation strategies that actually move the needle. From alternative financing hacks to untapped lead sources, we're showing you how to thrive in any market. Takeaways Real estate financing optionsCreative lead generation strategiesMarketing techinques Chapters 00:00 Introduction00:44 Introduction to Creative Financing03:47 Navigating Hard Money Lenders06:36 Exploring Alternative Financing Options09:44 Utilizing Retirement Accounts for Investments12:30 Innovative Lead Generation Strategies15:59 Creative Direct Mail Techniques18:58 Leveraging Obituaries for Lead Generation21:45 The Role of Virtual Assistants in Real Estate24:57 Conclusion and Final Thoughts34:52 Building Long-Term Success in Real Estate

    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
    30
  • Rating
    Clean
  • Copyright
    © 2026 Keith Gillispie