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.
#53 - I Wrote Off Everything and It Cost Me a House Now Worth $1 Million
In this episode of The First Deal Podcast, Dayton Lindsey sits down with Keith Gillispie to talk about taxes, capital gains, and how to stay bankable while paying as little as legally possible.
Keith shares the story of a five-unit property on five acres that he had under contract for around $750,000. The numbers showed he could live for free and cash flow $4,000 to $5,000 a month, but his CPA had written off so much that the lender saw him as broke on paper. The deal fell apart, and that property is now worth about $1 million.
From there, Keith explains how he now keeps his taxes low while still qualifying for loans, why he meets with his CPA every month instead of rushing in April, what he looks for in a great CPA, and why business owners should set a clear goal and let their experts lead.
Takeaways:
Writing off everything can cost you your next deal.
You can pay almost nothing in taxes and still stay bankable.
Meet with your CPA every month instead of scrambling in April.
The right CPA gets excited about tax code and specializes in real estate.
Give your team clear direction and then let the experts lead.
Chapters:
00:00 Introduction
00:48 Strategies for Capital Gains Tax Reduction
05:06 Real Estate Investment Insights
10:04 Navigating Tax Legislation Changes
17:56 Choosing the Right CPA
27:55 Handling Depreciation and Selling Properties
33:10 Outro
🎁Carter Lane’s Office Hours recording + Business Start-up: https://knowledge.reiautomated.io/courses/business-startup (https://knowledge.reiautomated.io/courses/business-startup)
📜FREE Purchase & Sales Agreement:
https://go.reiautomated.io/strongest-psa-lm (https://go.reiautomated.io/strongest-psa-lm)
📊FREE Deal Analyzer + Repair Estimator:
https://go.reiautomated.io/deal-analyzer (https://go.reiautomated.io/deal-analyzer)
📃FREE Joint Venture Agreement:
https://go.reiautomated.io/jv-agreement-flm (https://go.reiautomated.io/jv-agreement-flm)
🏠FREE Facebook Community:
https://www.facebook.com/groups/realestateinvestingandwholesaling (https://www.facebook.com/groups/realestateinvestingandwholesaling)
🧑🏻💻FREE COURSE (watch 5 min first):
https://playbook.reiautomated.io/?source=Keith&campaign=OFC (https://playbook.reiautomated.io/?source=Keith&campaign=OFC)
🌟CLIENT RESULTS:
https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb (https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb)
SOCIALS
Instagram: https://www.instagram.com/keithg_rei/ (https://www.instagram.com/keithg_rei/)
Facebook: https://www.facebook.com/Keith.Gillispie (https://www.facebook.com/Keith.Gillispie)
Music from #Uppbeat (free for Creators!):
https://uppbeat.io/t/monobox/backbone (https://uppbeat.io/t/monobox/backbone)
License code: OZZJFTOT1V6EYPPY
18 Sept 2026
#52 - The $10,000 Decision That Could Save You a YEAR Of Suffering
In this episode of The First Deal Podcast, Dayton Lindsey sits down with Keith Gillispie to break down how his acquisition process evolved from an inconsistent, overcomplicated system into a repeatable process built around principles.
Keith explains how taking multiple courses early in his career actually led him to combine several different systems into one bloated process, why it took him years to develop repeatability, and why every system he uses today exists because of a problem he has already experienced firsthand.
From there, the conversation moves into mentorship, paying for shortcuts, the true value of time, and the mistakes Keith made while building his first team.
Takeaways:
Why overeducation can sometimes lead to overanalysis
How combining several good systems can create one terrible system
Whether it's better to pay a mentor or learn everything through trial and error
Why Keith views time as a more valuable currency than money
How coaching can shorten the path to your first deal
Chapters:
00:00 Introduction to Real Estate Investing
00:48 Evolution of Acquisition Processes
10:38 The Value of Mentorship vs. Experience
22:36 Building a Team for Success
34:04 Outro
🎁FREE Goal Setting Masterclass:
https://knowledge.reiautomated.io/courses/self-mastery (https://knowledge.reiautomated.io/courses/self-mastery)
📜FREE Purchase & Sales Agreement:
https://go.reiautomated.io/strongest-psa-lm (https://go.reiautomated.io/strongest-psa-lm)
📊FREE Deal Analyzer + Repair Estimator:
https://go.reiautomated.io/deal-analyzer (https://go.reiautomated.io/deal-analyzer)
📃FREE Joint Venture Agreement:
https://go.reiautomated.io/jv-agreement-flm (https://go.reiautomated.io/jv-agreement-flm)
🏠FREE Facebook Community:
https://www.facebook.com/groups/realestateinvestingandwholesaling (https://www.facebook.com/groups/realestateinvestingandwholesaling)
🧑🏻💻FREE COURSE (watch 5 min first):
https://playbook.reiautomated.io/?source=Keith&campaign=OFC (https://playbook.reiautomated.io/?source=Keith&campaign=OFC)
🌟CLIENT RESULTS:
https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb (https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb)
SOCIALS
Instagram: https://www.instagram.com/keithg_rei/ (https://www.instagram.com/keithg_rei/)
Facebook: https://www.facebook.com/Keith.Gillispie (https://www.facebook.com/Keith.Gillispie)
Music from #Uppbeat (free for Creators!):
https://uppbeat.io/t/monobox/backbone (https://uppbeat.io/t/monobox/backbone)
License code: OZZJFTOT1V6EYPPY
9 Sept 2026
#51 - Avoid Early Hires, The Golden Portfolio Leverage Percentage, & Property Management Tips
Keith starts by sharing how he brought on both a partner and a virtual assistant almost immediately after launching his investing business in 2016 — and why he now believes hiring that early was a mistake.
He then walks through the 55% maximum leverage rule he personally uses across his rental portfolio and explains how he built that number by studying major historical market downturns.
Finally, Keith explains why investors managing rentals in multiple markets should stop trying to do everything themselves and hire an exceptional property management company instead.
Takeaways:
Why partnering on your first deal will help you “earn while you learn”
The difference between hiring a generalist and hiring a specialist
Why every recurring task should have a documented SOP
Why you shouldn't expect an employee to create your business systems for you
How Keith developed his personal 55% maximum portfolio leverage rule and how you can use it too
Why Keith believes paying 10% for excellent property management is worth it
Why websites and five-star reviews aren't enough when choosing a manager
Chapters:
00:00 Introduction
00:48 The Relentless Pursuit of Success
01:58 Starting Out in Real Estate Investing
06:39 The Importance of Leadership and Team Dynamics
11:35 Understanding Market Cycles and Financial Safety
15:50 Leveraging Real Estate Investments Wisely
20:58 Choosing the Right Property Management Company
24:12 Outro
🎁FREE Goal Setting Masterclass:
https://knowledge.reiautomated.io/courses/self-mastery (https://knowledge.reiautomated.io/courses/self-mastery)
📜FREE Purchase & Sales Agreement:
https://go.reiautomated.io/strongest-psa-lm (https://go.reiautomated.io/strongest-psa-lm)
📊FREE Deal Analyzer + Repair Estimator:
https://go.reiautomated.io/deal-analyzer (https://go.reiautomated.io/deal-analyzer)
📃FREE Joint Venture Agreement:
https://go.reiautomated.io/jv-agreement-flm (https://go.reiautomated.io/jv-agreement-flm)
🏠FREE Facebook Community:
https://www.facebook.com/groups/realestateinvestingandwholesaling (https://www.facebook.com/groups/realestateinvestingandwholesaling)
🧑🏻💻FREE COURSE (watch 5 min first):
https://playbook.reiautomated.io/?source=Keith&campaign=OFC (https://playbook.reiautomated.io/?source=Keith&campaign=OFC)
🌟CLIENT RESULTS:
https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb (https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb)
SOCIALS
Instagram: https://www.instagram.com/keithg_rei/ (https://www.instagram.com/keithg_rei/)
Facebook: https://www.facebook.com/Keith.Gillispie (https://www.facebook.com/Keith.Gillispie)
Music from #Uppbeat (free for Creators!):
https://uppbeat.io/t/monobox/backbone (https://uppbeat.io/t/monobox/backbone)
License code: OZZJFTOT1V6EYPPY
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