Keith Gillispie
First Deal Podcast
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.
Where to listen?
Podcasts in the app Replaio Radio Coming soonPodcasts are coming to the app soon. Install now and be the first to see a whole new take on podcasts
Episodes
#11 - How To Properly Systematize Rehab Work 31.03.2026 29:44
The conversation delves into the significance of debt-to-income ratio (DTI) in loan approval, the impact of DTI on different loan types, and the importance of a simplified and detailed scope of work for effective communication with contractors. Takeaways Debt-to-income ratio (DTI) is a critical factor in loan approval Different loan types have varying DTI requirements Simplified and detailed scope...
#10 - The Different Loan Types And How They Impact Investors 26.03.2026 26:03
The conversation covers different types of loans, including FHA, VA, DSCR, conventional, and portfolio loans, and their impact on real estate investing. It also delves into the significance of interest rates and their influence on investment strategies. Takeaways Loan types serve different purposes Interest rates impact investment strategies Chapters 00:00 Understanding Different Loan Types 10:14...
#9 - The Worst Deal Keith Has Ever Done 26.03.2026 29:13
This conversation delves into the challenges of real estate investing, focusing on a deal gone wrong and the subsequent legal battles. It also explores the contractor hiring process and the importance of thorough pre-screening. The discussion provides valuable insights into the complexities of real estate investment and the need for meticulous planning and execution. Takeaways Dealing with a deal...
#8 - Why The Worst Red Flags Are The Best Green Flags 26.03.2026 24:18
This conversation covers the identification of bad real estate deals, the importance of professional inspections, evaluating risk in real estate, a lucrative real estate deal, and understanding red flags in inspections. Takeaways Identifying bad deals based on financial loss and problematic sellers The importance of professional inspections for risk mitigation Evaluating risk in real estate based...
#7 - The 3 Contingencies All Investors Need In Their Contracts 14.03.2026 24:54
This conversation covers the importance of effective communication and the power of asking questions in sales, specifically in the context of real estate deals. Keith delves into the use of contingencies for beginners, core contingencies for real estate deals, and negotiating with sellers without being pushy or salesy. Takeaways Effective communication in sales The power of asking questions Chapte...
#6 - Why You Should NEVER Make Offers 12.03.2026 29:45
The conversation delves into the process of deciding offer prices (and why making them is killing your close rate), emphasizing the importance of understanding the seller's situation and being personable and empathetic. It also highlights the significance of proper deal analysis and risk assessment in real estate investing. Takeaways Understanding the seller's situation Importance of being persona...
#5 - Why Sales Isn't About Selling 03.03.2026 47:37
In this conversation, Keith Gillispie discusses the art of sales and emphasizes that sales is effective communication. He also explains the concept of wholesaling and the evaluation process involved. Additionally, he provides insights into the importance of tracking KPIs for real estate investors, demonstrating the impact of KPIs on business success. Takeaways Deal sourcing depends on individual c...
#4 - Mastering Deal Analysis 27.02.2026 39:21
In this conversation, Keith discusses the key numbers needed to analyze a rental property quickly, emphasizing the importance of rent, property value, loan details, and operating expenses. He also shares insights on cash flow and property types, highlighting the challenges of negative cash flow. Additionally, he provides valuable tips on estimating rent accurately using Rentometer and emphasizes t...
#3 - Where The Next Real Estate Boom Will Start 26.02.2026 29:35
The podcast episode covers the key aspects of real estate investing, including market selection, price range considerations, and property type recommendations. Keith Gillespie provides valuable insights into market trends, network influence, and the impact of federal policies on real estate. He emphasizes the importance of understanding market dynamics and choosing investment properties based on m...
#2 - The Principles Of Real Estate Investing Success 26.02.2026 37:03
In this podcast, Keith Gillespie, a real estate expert with 10 years of experience, shares insights on real estate investing, deal strategies, and common mistakes. He emphasizes the importance of consistency and provides practical steps for beginners to kickstart their real estate journey. - 📜FREE Purchase & Sales Agreement: https://go.reiautomated.io/strongest-psa-lm 📊FREE Deal Analyzer +...
#1 - Your First Deal Isn't About Making Money 26.02.2026 18:28
Keith Gillispie is a 10+ year, seasoned real estate investing veteran who has closed 400+ deals across the United States and is the owner/CEO of Crowne Properties and REI Automated. What is the outcome you should be aiming for for your first real estate deal? Is it to make as much money as you can from the property like a greedy goblin? Or is it about proving to yourself that you can go down this...
Similar podcasts
Replaio is not a podcast publisher; show names, artwork and audio belong to their authors and are distributed through public RSS feeds.