First Deal Podcast
Claim This Podcastby Keith Gillispie
Podcast Overview
<p>Your first deal is the hardest - until you know what actually works. <br /><br />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. <br /><br />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.</p>
Language
🇺🇲
Publishing Since
2/26/2026
1 verified contact email on file for First Deal Podcast
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Recent Episodes
July 22, 2026
#39 - Wholesaling, Biggest Regrets, And What A Great Deal Looks Like in 2026
<p>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.</p><p></p><p>Takeaways</p><ul><li>Wholesaling offers quick cash but may not lead to long-term wealth </li><li>The choice between cash flow and appreciation depends on 2 factors</li></ul><p></p><p>Chapters</p><ul><li>00:00 Introduction</li><li>00:48 Wholesaling: A Quick Path to Wealth?</li><li>09:35 Strategies for Real Estate Investment</li><li>12:30 Cash Flow vs. Appreciation: Investment Goals</li><li>19:26 Defining a Great Deal in 2026</li><li>27:21 Outro</li></ul><p></p><p>📜FREE Purchase & Sales Agreement: <a rel="noopener noreferrer nofollow" href="https://go.reiautomated.io/strongest-psa-lm" target="_blank">https://go.reiautomated.io/strongest-psa-lm</a> <br /></p><p>📊FREE Deal Analyzer + Repair Estimator: <a rel="noopener noreferrer nofollow" href="https://go.reiautomated.io/deal-analyzer" target="_blank">https://go.reiautomated.io/deal-analyzer</a> </p><p> </p><p>📃FREE Joint Venture Agreement: <a rel="noopener noreferrer nofollow" href="https://go.reiautomated.io/jv-agreement-flm" target="_blank">https://go.reiautomated.io/jv-agreement-flm</a> <br /></p><p>🏠FREE Facebook Community: <a rel="noopener noreferrer nofollow" href="https://www.facebook.com/groups/realestateinvestingandwholesaling" target="_blank">https://www.facebook.com/groups/realestateinvestingandwholesaling</a><br /></p><p>🧑🏻💻FREE COURSE (watch 5 min first): <a rel="noopener noreferrer nofollow" href="https://playbook.reiautomated.io/?source=Keith&campaign=OFC" target="_blank">https://playbook.reiautomated.io/?source=Keith&campaign=OFC</a> </p><p></p><p>🌟CLIENT RESULTS: <a rel="noopener noreferrer nofollow" href="https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb" target="_blank">https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb</a> </p><p></p><p>WHAT WE OFFER: <a rel="noopener noreferrer nofollow" href="https://youtu.be/JbV0LqjdhJ8" target="_blank">https://youtu.be/JbV0LqjdhJ8</a> </p><p></p><p><b>SOCIALS</b></p><p>Instagram: <a rel="noopener noreferrer nofollow" href="https://www.instagram.com/keithg_rei/" target="_blank">https://www.instagram.com/keithg_rei/</a> </p><p>Facebook: <a rel="noopener noreferrer nofollow" href="https://www.facebook.com/Keith.Gillispie" target="_blank">https://www.facebook.com/Keith.Gillispie</a></p><p></p><p>Music from #Uppbeat (free for Creators!):</p><p><a rel="noopener noreferrer nofollow" href="https://uppbeat.io/t/monobox/backbone" target="_blank">https://uppbeat.io/t/monobox/backbone</a></p><p>License code: OZZJFTOT1V6EYPPY</p>
July 18, 2026
#38 - How Investors Can Lose Up To $60K, Without Even Realizing It
<p>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.</p><p></p><p>Takeaways</p><ul><li>Underestimating repair costs</li><li>Overestimating ARV</li><li>Ignoring holding costs</li></ul><p></p><p>Chapters</p><ul><li>00:00 Introduction</li><li>02:19 Common Underestimations in Fix and Flip Calculations</li><li>05:14 The Impact of Time on Real Estate Deals</li><li>08:23 Real-Life Case Study: Lessons Learned from a Failed Deal</li><li>11:05 Conclusion and Call to Action</li><li>14:28 Outro</li></ul><p></p><p>📜FREE Purchase & Sales Agreement: <a rel="noopener noreferrer nofollow" href="https://go.reiautomated.io/strongest-psa-lm" target="_blank">https://go.reiautomated.io/strongest-psa-lm</a> <br /></p><p>📊FREE Deal Analyzer + Repair Estimator: <a rel="noopener noreferrer nofollow" href="https://go.reiautomated.io/deal-analyzer" target="_blank">https://go.reiautomated.io/deal-analyzer</a> </p><p> </p><p>📃FREE Joint Venture Agreement: <a rel="noopener noreferrer nofollow" href="https://go.reiautomated.io/jv-agreement-flm" target="_blank">https://go.reiautomated.io/jv-agreement-flm</a> </p><p></p><p>🏠FREE Facebook Community: <a rel="noopener noreferrer nofollow" href="https://www.facebook.com/groups/realestateinvestingandwholesaling" target="_blank">https://www.facebook.com/groups/realestateinvestingandwholesaling</a> </p><p>🧑🏻💻FREE COURSE (watch 5 min first): <a rel="noopener noreferrer nofollow" href="https://playbook.reiautomated.io/?source=Keith&campaign=OFC" target="_blank">https://playbook.reiautomated.io/?source=Keith&campaign=OFC</a> </p><p></p><p>🌟CLIENT RESULTS: <a rel="noopener noreferrer nofollow" href="https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb" target="_blank">https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb</a> <br /></p><p>WHAT WE OFFER: <a rel="noopener noreferrer nofollow" href="https://youtu.be/JbV0LqjdhJ8" target="_blank">https://youtu.be/JbV0LqjdhJ8</a> <br /></p><p><b>SOCIALS</b></p><p>Instagram: <a rel="noopener noreferrer nofollow" href="https://www.instagram.com/keithg_rei/" target="_blank">https://www.instagram.com/keithg_rei/</a> </p><p>Facebook: <a rel="noopener noreferrer nofollow" href="https://www.facebook.com/Keith.Gillispie" target="_blank">https://www.facebook.com/Keith.Gillispie</a></p><p></p><p>Music from #Uppbeat (free for Creators!):</p><p><a rel="noopener noreferrer nofollow" href="https://uppbeat.io/t/monobox/backbone" target="_blank">https://uppbeat.io/t/monobox/backbone</a></p><p>License code: OZZJFTOT1V6EYPPY</p>
July 15, 2026
#37 - The One System That 10x'd My Leads Without Spending More Money
<p>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.</p><p></p><p>Takeaways</p><ul><li>Real estate investment strategies</li><li>Importance of lead connection rate</li></ul><p></p><p>Chapters</p><ul><li>00:00 Introduction</li><li>00:41 Cash Flowing Rentals: The Key to Success</li><li>04:42 Understanding Notes: Passive Income Explained</li><li>08:21 Easy Flips: The Whole-Tail Strategy</li><li>10:23 Tax Strategies for Real Estate Investors</li><li>14:02 Scaling Through Systems and Processes</li><li>22:29 Conclusion and Key Takeaways</li><li>22:50 Outro</li></ul><p></p><p>📜FREE Purchase & Sales Agreement: <a rel="noopener noreferrer nofollow" href="https://go.reiautomated.io/strongest-psa-lm" target="_blank">https://go.reiautomated.io/strongest-psa-lm</a> </p><p></p><p>📊FREE Deal Analyzer + Repair Estimator: <a rel="noopener noreferrer nofollow" href="https://go.reiautomated.io/deal-analyzer" target="_blank">https://go.reiautomated.io/deal-analyzer</a> </p><p> </p><p>📃FREE Joint Venture Agreement: <a rel="noopener noreferrer nofollow" href="https://go.reiautomated.io/jv-agreement-flm" target="_blank">https://go.reiautomated.io/jv-agreement-flm</a> </p><p></p><p>🏠FREE Facebook Community: <a rel="noopener noreferrer nofollow" href="https://www.facebook.com/groups/realestateinvestingandwholesaling" target="_blank">https://www.facebook.com/groups/realestateinvestingandwholesaling</a><br /></p><p>🧑🏻💻FREE COURSE (watch 5 min first): <a rel="noopener noreferrer nofollow" href="https://playbook.reiautomated.io/?source=Keith&campaign=OFC" target="_blank">https://playbook.reiautomated.io/?source=Keith&campaign=OFC</a> </p><p></p><p>🌟CLIENT RESULTS: <a rel="noopener noreferrer nofollow" href="https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb" target="_blank">https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb</a> </p><p></p><p>WHAT WE OFFER: <a rel="noopener noreferrer nofollow" href="https://youtu.be/JbV0LqjdhJ8" target="_blank">https://youtu.be/JbV0LqjdhJ8</a> <br /></p><p><b>SOCIALS</b></p><p>Instagram: <a rel="noopener noreferrer nofollow" href="https://www.instagram.com/keithg_rei/" target="_blank">https://www.instagram.com/keithg_rei/</a> </p><p>Facebook: <a rel="noopener noreferrer nofollow" href="https://www.facebook.com/Keith.Gillispie" target="_blank">https://www.facebook.com/Keith.Gillispie</a></p><p></p><p>Music from #Uppbeat (free for Creators!):</p><p><a rel="noopener noreferrer nofollow" href="https://uppbeat.io/t/monobox/backbone" target="_blank">https://uppbeat.io/t/monobox/backbone</a></p><p>License code: OZZJFTOT1V6EYPPY</p><p></p>
39 total episodes available
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- What is First Deal Podcast?
<p>Your first deal is the hardest - until you know what actually works. <br /><br />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. <br /><br />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.</p> - How often does this podcast release new episodes?
This podcast updates daily.
- Where can I listen to this podcast?
This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
- Does this podcast accept guests?
Information about guest appearances is not available.
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