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. 2d ago

    #41 - Creative Financing Explained And How To Find Lenders Who Won't Scam You

    Keith breaks down why creative financing is his favorite strategy in today's market, shares a real story about a client who got scammed out of $27,000 by a fake hard money lender, and ends with a mindset shift that redefines what "safe" actually means in real estate — and it has nothing to do with the price of the house. Takeaways Is Creative Financing Real or Internet Hype?How to Find Real Lenders (And Avoid Getting Scammed)How Keith Got 100/100 FinancingCash Reserves: Keith's 35% RuleSafety Is Not Found in the Purchase Price Chapters 00:00 Introduction to Real Estate Investing00:48 Creative Financing: Strategies and Insights06:32 Building Relationships with Lenders12:14 Cash Reserves: Philosophy and Practice20:23 Risk Management in Real Estate Investing29:18 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 Music from #Uppbeat (free for Creators!): https://uppbeat.io/t/monobox/backbone License code: OZZJFTOT1V6EYPPY

  2. Jul 24

    #40 - Keith Offered More Than Asking Price And Here's Why It Made Perfect Sense

    Keith does a live walkthrough inside Deal Labs to show exactly how he's finding and underwriting deals in a high interest rate environment — including the counterintuitive strategy of offering sellers more than their asking price. Then he shares the exact leverage percentage he never crosses in his portfolio, backed by 30 years of metro-level data going all the way back to 2008. Takeaways How to Underwrite Deals When Interest Rates Are HighLive Deal Labs WalkthroughHow Much Leverage Is Too Much — Keith's 55% Rule Chapters 00:00 Introduction00:48 Navigating Elevated Interest Rates21:59 Understanding Leverage in Real Estate Investment28:40 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 Music from #Uppbeat (free for Creators!): https://uppbeat.io/t/monobox/backbone License code: OZZJFTOT1V6EYPPY

  3. Jul 22

    #39 - Wholesaling, Biggest Regrets, And What A Great Deal Looks Like in 2026

    Keith gives his most honest take yet on wholesaling — what it actually is, what it isn't, and who it's right for. Then he breaks down the cash flow vs. appreciation debate using order of operations logic, shares the embarrassing truth about how many houses he kept in his first eight years, and defines what a good deal looks like in today's uncertain market. Takeaways Wholesaling offers quick cash but may not lead to long-term wealth The choice between cash flow and appreciation depends on 2 factors Chapters 00:00 Introduction00:48 Wholesaling: A Quick Path to Wealth?09:35 Strategies for Real Estate Investment12:30 Cash Flow vs. Appreciation: Investment Goals19:26 Defining a Great Deal in 202627:21 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 Music from #Uppbeat (free for Creators!): https://uppbeat.io/t/monobox/backbone License code: OZZJFTOT1V6EYPPY

  4. Jul 18

    #38 - How Investors Can Lose Up To $60K, Without Even Realizing It

    Keith draws from over 1,500 deals underwritten in office hours alone to break down the three numbers that consistently destroy fix and flip profits — and shares a real client story about a contractor who used AI to fake renovation photos to siphon off $15,000 out of a deal. Takeaways Underestimating repair costsOverestimating ARVIgnoring holding costs Chapters 00:00 Introduction02:19 Common Underestimations in Fix and Flip Calculations05:14 The Impact of Time on Real Estate Deals08:23 Real-Life Case Study: Lessons Learned from a Failed Deal11:05 Conclusion and Call to Action14:28 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 Music from #Uppbeat (free for Creators!): https://uppbeat.io/t/monobox/backbone License code: OZZJFTOT1V6EYPPY

  5. Jul 15

    #37 - The One System That 10x'd My Leads Without Spending More Money

    Keith opens up his actual portfolio and breaks down what he'd sell, what he's keeping forever, and what he's aggressively buying more of. Then he calls out the tax trap most investors don't see coming on whole tails, and reveals the single system that had a bigger impact on his business than anything else he's ever implemented. Takeaways Real estate investment strategiesImportance of lead connection rate Chapters 00:00 Introduction00:41 Cash Flowing Rentals: The Key to Success04:42 Understanding Notes: Passive Income Explained08:21 Easy Flips: The Whole-Tail Strategy10:23 Tax Strategies for Real Estate Investors14:02 Scaling Through Systems and Processes22:29 Conclusion and Key Takeaways22:50 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 Music from #Uppbeat (free for Creators!): https://uppbeat.io/t/monobox/backbone License code: OZZJFTOT1V6EYPPY

  6. Jul 10

    #36 - Stop Using the 70% Rule... It's Costing You Deals

    Keith reflects on what he'd do differently if he were rebuilding his portfolio from scratch, calls out the most dangerous piece of conventional wisdom still circulating in real estate investing, and gives an honest, personal answer to what financial freedom actually looks like in his day-to-day life — and whether it matched what he imagined when he started. Takeaways Why inbound marketing is worth the expense.What the crucial components are for long-term success in real estate investing. Chapters 00:00 Introduction00:48 Building a Portfolio: Lessons Learned07:25 The Importance of Team Building11:09 Challenging Conventional Wisdom in Real Estate16:32 Redefining Financial Freedom23:25 Final Thoughts24:03 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 Music from #Uppbeat (free for Creators!): https://uppbeat.io/t/monobox/backbone License code: OZZJFTOT1V6EYPPY

  7. Jul 8

    #35 - How Keith Made $30,000/mo From Rentals (And Lost It All)

    Keith lays out his three-step deal analysis framework — the same process he uses on every property regardless of location, price point, or condition. Then he breaks down where short-term rentals actually stand right now and what killed his own STR business in Hawaii. He closes with the two numbers investors almost always underestimate on a fix and flip, and why getting them wrong is so costly.  Takeaways What it takes to accurately estimate repairs in real estate dealsWhat you can do to decrease your time investment into real estate Chapters 00:00 Introduction00:48 Analyzing Deals in Under 10 Minutes12:23 Short-Term vs Long-Term Rentals21:18 Understanding Fix and Flip Math26:01 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 Music from #Uppbeat (free for Creators!): https://uppbeat.io/t/monobox/backbone License code: OZZJFTOT1V6EYPPY

  8. Jul 4

    #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

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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
    2026
  • Episodes
    41
  • Rating
    Clean
  • Copyright
    © 2026 Keith Gillispie