First Deal Podcast

#29 - How To Overcome A Competing Cash Offer With "The Seedling Method"

Keith Gillispie — Tue, 16 Jun 2026 20:15:46 GMT

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 fan
The power of negotiation questions
How to deal with third parties trying desperately to rob ypu of your rewards

Chapters

00:00 Introduction
00:55 The Power of Questions in Real Estate Negotiation
07:37 Establishing Trust and Process with Sellers
16:44 Handling Competing Offers and Seller Doubts
24:06 Managing Third-Party Influences in Real Estate Deals
31:53 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

#28 - Finally Putting An End To The Great Wholesale Vs. Flipping Debate?

Keith Gillispie — Thu, 11 Jun 2026 00:23:46 GMT

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't
The 3 Most Dangerous Deal Structures Right Now as of This Recording

Chapters

00:00 Introduction
00:44 Wholesaling vs. Flipping: The Great Debate
06:48 Navigating Nationwide vs. Local Business Models
12:46 Understanding Sub 2 Transactions and Their Risks
18:54 Legislation and the Future of Wholesaling
26:21 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 - Building A Social Presence For Lead Gen, And Why Speed To Lead Matters

Keith Gillispie — Thu, 04 Jun 2026 15:26:10 GMT

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 strategy
Importance of speed to lead in real estate investing
Leveraging social media for lead generation

Chapters

00:00 Introduction
00:44 Real Estate Investing Strategies
03:33 Leveraging Technology in Real Estate
06:38 The Importance of Speed to Lead
09:35 Transitioning from Outbound to Inbound Marketing
12:53 Building a Social Media Presence for Lead Generation
15:45 Understanding Deal Structures and Strategies
35:05 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

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

Keith Gillispie — Wed, 03 Jun 2026 00:56:29 GMT

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 wealth
Lead sources require consistent effort and multi-touch marketing
Planning for the future is crucial for personal and financial well-being

Chapters

00:00 Introduction
00:44 Reconnecting After a Break
03:45 The Lifespan of Lead Sources in Real Estate
06:56 Strategies to Stand Out in a Crowded Market
12:39 Engagement Metrics and Multi-Channel Marketing
18:56 Generational Differences in Communication Preferences
24:58 Ethics in Real Estate Marketing and Lead Generation
31:02 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

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

Keith Gillispie — Thu, 28 May 2026 18:48:23 GMT

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 strategy
Innovative deal structuring in real estate

Chapters

00:00 Introduction
00:44 Keith Can't Choose A Color
01:46 Unusual Lead Generation Strategies
06:50 The Power of Curiosity in Marketing
12:50 Emerging Deal Structures: Novations
19:03 Key Clauses in Contracts for Investors
29:27 The Skill of Real Estate Investing
29:28 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

#24 - The AI Takeover Of Real Estate Investing

Keith Gillispie — Wed, 27 May 2026 04:01:11 GMT

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 strategy
The impact of AI on real estate and marketing

Chapters

00:00 Introduction
00:44 The Impact of AI on Investment Strategies
11:45 Creative Financing in Real Estate
18:39 Improving Seller Communication
20:16 Challenging Conventional Wisdom in Negotiation
25:46 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

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

Keith Gillispie — Sun, 24 May 2026 00:34:05 GMT

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 options
Creative lead generation strategies
Marketing techinques

Chapters

00:00 Introduction
00:44 Introduction to Creative Financing
03:47 Navigating Hard Money Lenders
06:36 Exploring Alternative Financing Options
09:44 Utilizing Retirement Accounts for Investments
12:30 Innovative Lead Generation Strategies
15:59 Creative Direct Mail Techniques
18:58 Leveraging Obituaries for Lead Generation
21:45 The Role of Virtual Assistants in Real Estate
24:57 Conclusion and Final Thoughts
34:52 Building Long-Term Success in Real Estate

#22 - In-Person Vs. Virtual Teams (Which Is Best For You?)

Keith Gillispie — Fri, 22 May 2026 04:43:30 GMT

The guys cover the topics of real estate as a means of long-term wealth building and the comparison between building in-person and virtual teams. It provides insights into the challenges and advantages of each approach, offering valuable perspectives for real estate investors and entrepreneurs.

Takeaways

Real estate for long-term wealth
Building in-person vs virtual teams

Chapters

00:00 Introduction
00:44 Overview of Real Estate Questions Investors Have
12:45 Building Teams: In-Person vs. Virtual
25:00 Wholesaling and Pre-Foreclosure Properties
25:49 Building Long-Term Success in Real Estate

#21 - Understanding The Ins And Outs Of Cash-Savvy PPL Budgeting

Keith Gillispie — Wed, 20 May 2026 03:56:51 GMT

Keith and Dayton dive into the highly debated topic of PPL marketing and budgeting. Keith explains not just the essential principle you must follow for effective budgeting, but also pulls back the curtain on how providers work and what their policies are. They also converse over affiliated topics like navigating LLC ownership, contacting owners

and building an effective cash buyers list.

Takeaways

Real estate for long-term wealth
Building a buyer's list

Chapters

00:00 Introduction
00:44 Introduction to PPL Budgeting
03:36 Understanding PPL Providers and Their Policies
06:54 Navigating LLC Ownership and Contacting Owners
09:45 Building a Cash Buyers List Effectively
12:45 The Importance of Having a Deal First
16:00 Conclusion and Next Steps
27:22 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

#20 - Lead Generation Secrets Of A 10+ Year Investor

Keith Gillispie — Thu, 14 May 2026 18:02:32 GMT

The guys cover the topics of lead generation strategies, the importance of accurate data for lead generation, marketing, and data quality. It provides invaluable insights into the world of the critical role that data accuracy plays in lead generation.

Takeaways

Real estate as a wealth-building strategy
Importance of accurate data for lead generation

Chapters

00:00 Introduction
00:44 Understanding Lead Generation In Real Estate
13:36 Navigating Different Marketing Strategies
20:54 The Importance of Accurate Data in Real Estate
31:02 Conclusion and Future Insights
31:08 The Skill of Real Estate Investing

#19 - Learn To Master The Art Of The Double Close (And Avoid The Pitfalls)

Keith Gillispie — Wed, 13 May 2026 03:29:17 GMT

The guys cover the wealth-building potential of real estate, including how simple it is to build long-term wealth through real estate. They also dive deep into the strategies for earnest money deposit, transactional funding, and addressing challenges and providing virtual and in-person strategies for sourcing private money lenders.

Takeaways

Real estate as a wealth-building strategy
Strategies for sourcing private money lenders

Chapters

00:00 Introduction and Wealth Building
04:48 Earnest Money Deposit and Transactional Funding
14:57 Sourcing Private Money Lenders

📜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

#18 - The Insider Secrets Of Transactional Funding

Keith Gillispie — Sat, 09 May 2026 03:56:16 GMT

The guys cover long-term wealth, proof of funds as a wholesaler, the gray area of proof of funds, transactional funding and its risks, challenges with proof of funds, renegotiation and backing out, ethical considerations in real estate, selecting a hard money lender, green flags and red flags in lenders, and transactional funding companies.

Takeaways

Real estate as a means of building long-term wealth
Ethical considerations in real estate transactions

Chapters

00:00 Real Estate and Long-Term Wealth
07:14 Challenges with Proof of Funds
13:04 Selecting a Hard Money Lender
26:13 Transactional Funding Companies

🎯DealBase - The Only CRM Built For Real Estate Investors: https://www.reiautomated.io/dealbase
🌐Our Website: https://www.reiautomated.io
📜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
Keith Gillispie is a real estate investor, coach, and CEO of Crowne Properties and REI Automated.
In this podcast-style series, you can expect to learn the ins and outs of real estate investing, why the modern approach of “making offers” is a ludicrous idea, and commentary on the current state of markets, trends, and strategies.
Join your host, Dayton Lindsey, as he extracts 10+ years of investing knowledge from Keith for your listening/viewing pleasure.
New here? Start below. Ready to scale? We'll show you how.
❤️ FOLLOW ME ON SOCIALS:
✅Instagram: https://www.instagram.com/keithg_rei/
✅Facebook: https://www.facebook.com/Keith.Gillispie

#17 - How To Raise Rentability While Keeping A Happy Tenant

Keith Gillispie — Wed, 06 May 2026 02:30:54 GMT

The guys cover the intersection of nature and technology, the purpose of the show, selecting the right tenant, property management and turnover, upgrades to improve rentability, sizzle features and rentability, catering to women and men in renovations, the impact of quality photos on rentability, yearly plan to increase NOI, quality issues with decreasing expenses, controlling insurance costs, understanding insurance coverage, and value vs. cost in insurance.

Takeaways

Nature and technology intersect in real estate
Catering to women and men in renovations
Understanding the impact of quality photos on rentability
Controlling insurance costs for increased NOI

Chapters

00:00 The Intersection of Nature and Technology
06:32 Catering to Women in Renovations
14:30 Quality Issues with Decreasing Expenses
21:37 Value vs. Cost in Insurance

#16 - The Wealth-Building Secrets For Rental Investors

Keith Gillispie — Sat, 02 May 2026 22:49:22 GMT

Keith covers a vast number of topics including: real estate wealth building, estate planning, rent increases and inflation, property management and profit leakage, utility, insurance, and tax levers for NOI, and the importance of shopping around. Keith and Dayton discuss strategies for long-term wealth building, legacy protection, rent increase management, profit leakage prevention, and the impact of utilities, insurance, and taxes on net operating income.

Takeaways

Long-term wealth building through real estate
Importance of estate planning and legacy protection

Chapters

00:00 Real Estate Wealth Building
08:35 Property Management and Profit Leakage
18:24 Utility, Insurance, and Tax Levers for NOI

#15 - Maximizing Rental Income

Keith Gillispie — Wed, 22 Apr 2026 02:14:24 GMT

The conversation covers the KPIs of a good property manager, the components of a property manager agreement, strategies for preventing maintenance costs from impacting cash flow, and the determination of appropriate reserves for maintenance costs and vacancy. Keith Gillispie provides insights and recommendations for property management and investor protection.

Takeaways

Defining KPIs and metrics for evaluating property manager performance
Setting aside appropriate reserves for maintenance costs and vacancy

Chapters

00:00 Introduction and Property Manager KPIs
09:04 Property Manager Agreement and Investor Protection
17:49 Preventing Maintenance Costs from Impacting Cash Flow

#14 - The Essential Non-Negotiable Clauses You NEED For Leases

Keith Gillispie — Sat, 18 Apr 2026 13:00:00 GMT

The conversation delves into the discussion of non-negotiable lease clauses and exit strategies, followed by a comparison of lease options vs. leases and the associated responsibilities. The conversation then explores voiding the option and tenant reliability, move-in processes, and dispute prevention, concluding with a focus on formal written agreements and communication.

Takeaways

Lease Clauses and Non-Negotiables
Move-In Process and Preventing Disputes
Formal Written Agreements

Chapters

00:00 Introduction and Setting the Stage
06:26 Voiding the Option and Tenant Reliability
13:20 Move-In Process and Dispute Prevention

#13 - Why You Should Use Property Management If You Have Tenants

Keith Gillispie — Fri, 17 Apr 2026 23:36:56 GMT

Keith Gillespie shares insights on tenant screening criteria, rent pricing strategies, and property management systems. He also discusses the importance of finding the right property management company and shares a unique perspective on entrepreneurship.

Takeaways

Tenant screening criteria: Job stability and rental affordability are key indicators of a good tenant.
Rent pricing strategies: Section 8 rent is determined by government subsidies, while fair market rent is influenced by local market conditions.
Property management systems: Effective showings and lead collection are crucial for leasing success.
Finding the right property management company: Seek referrals from experienced investors with a large portfolio of properties.
Entrepreneurship insights: Keith shares unconventional insights on the entrepreneurial skills learned from the drug trade.

Chapters

00:00 Introduction and Audience Engagement
06:00 Rent Pricing Strategies
14:11 Property Management Systems
23:58 Entrepreneurship Insights

#12 - How To Stop Tenant Disputes Before They Happen

Keith Gillispie — Thu, 09 Apr 2026 20:42:26 GMT

The conversation begins with an introduction and small talk, leading into a discussion about common rehab overruns and how to prevent them. Keith shares insights on the aspects of rehab that typically run over budget and the importance of contingency planning. He also discusses the challenges of remote rehab management and the need for proactive measures to prevent unforeseen expenses. The conversation provides valuable insights into the world of real estate rehab and the strategies for successful property renovation.

Takeaways

Rehab Overruns
Preventing Overruns

Chapters

00:00 Introduction and Small Talk

#11 - How To Properly Systematize Rehab Work

Keith Gillispie — Tue, 31 Mar 2026 15:00:00 GMT

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 of work is essential for effective communication with contractors

Chapters

00:00 Understanding Debt-to-Income Ratio (DTI) and Loan Approval
03:09 Navigating Loan Types and Financing Strategies
05:58 Structing Finance Plans for Properties
08:51 Building Effective Rehab Scopes of Work

#10 - The Different Loan Types And How They Impact Investors

Keith Gillispie — Thu, 26 Mar 2026 21:10:37 GMT

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 Insights on Portfolio Loans
17:08 Impact of Interest Rates on Investment Strategies

#9 - The Worst Deal Keith Has Ever Done

Keith Gillispie — Thu, 26 Mar 2026 20:25:25 GMT

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 gone wrong
Challenges of real estate investing

Chapters

00:00 The Worst Deal Ever
06:59 Navigating Legal Battles
21:59 Contractor Hiring Process

#8 - Why The Worst Red Flags Are The Best Green Flags

Keith Gillispie — Thu, 26 Mar 2026 20:24:11 GMT

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 on market analysis and property value
The potential for lucrative real estate deals through strategic investments
Understanding red flags in inspections as opportunities for negotiation and risk assessment

Chapters

00:00 Identifying Bad Deals
05:24 Evaluating Risk in Real Estate
15:19 Understanding Red Flags in Inspections

#7 - The 3 Contingencies All Investors Need In Their Contracts

Keith Gillispie — Sat, 14 Mar 2026 22:02:36 GMT

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

Chapters

00:00 Introduction
11:04 Negotiating with Sellers in Real Estate Deals

#6 - Why You Should NEVER Make Offers

Keith Gillispie — Thu, 12 Mar 2026 15:44:16 GMT

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 personable and empathetic
Proper deal analysis and risk assessment

Chapters

00:00 The Simplest Way to Decide Offer Price
16:35 The Role of the Investor in Seller Interactions

#5 - Why Sales Isn't About Selling

Keith Gillispie — Tue, 03 Mar 2026 15:38:56 GMT

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 circumstances
Effective communication with real estate agents is key Sales is effective communication
Wholesaling involves assigning a contract
Tracking KPIs is crucial for real estate investors

Chapters

00:00 Best Deal Sources for Beginners
07:28 Lead Routine and Follow-Up
15:54 Effective Communication with Real Estate Agents
23:32 The Art of Sales
36:24 Tracking KPIs for Real Estate Investors

#4 - Mastering Deal Analysis

Keith Gillispie — Fri, 27 Feb 2026 23:43:19 GMT

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 the ethical use of multiple accounts for analysis. The conversation delves into the underestimated expenses in real estate, the applicability of cash on cash return, and the minimum deal standards and exit strategy in real estate investing.

Takeaways

Rental property analysis
Estimating rent accurately Maintenance and repairs are underestimated expenses
Cash on cash return may not be applicable with no money in the deal

Chapters

00:00 Analyzing Rental Property Numbers
06:30 Cash Flow and Property Types
16:52 Estimating Rent Accurately
28:24 Cash on Cash Return and Misleading Metrics

#3 - Where The Next Real Estate Boom Will Start

Keith Gillispie — Thu, 26 Feb 2026 19:52:10 GMT

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 market-specific factors.

📜FREE Purchase & Sales Agreement: https://go.reiautomated.io/strongest-psa-lm

📊FREE Deal Analyzer + Repair Estimator: https://go.reiautomated.io/deal-analyzer

🖥️FREE First Deal Fast-Track Webinar: https://www.firstdealfasttrack.com/register

📃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

Takeaways

Market selection is influenced by population growth, transaction volume, and months of inventory.
The price range for real estate investing should be based on the median sales price point of the average house in the area, with a focus on the 35th to 50th percentile for safety and stability.

Chapters

00:00 Property Type Recommendations

#2 - The Principles Of Real Estate Investing Success

Keith Gillispie — Thu, 26 Feb 2026 19:45:45 GMT

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 + Repair Estimator: https://go.reiautomated.io/deal-analyzer

🖥️FREE First Deal Fast-Track Webinar: https://www.firstdealfasttrack.com/register

📃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

Takeaways

Consistency is key to success in real estate investing.
Practical steps for beginners include using bandit signs, getting a VOIP phone number, and joining a local Real Estate Investor Association (REIA).

Chapters

00:00 Introduction and Podcast Overview
08:12 Acquiring Assets and Market Trends
15:26 Establishing a Buy Box and Mistakes Beginners Make
25:35 Biggest Mistakes in the First 90 Days of Real Estate Business

#1 - Your First Deal Isn't About Making Money

Keith Gillispie — Thu, 26 Feb 2026 19:38:41 GMT

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 path that has led millions of people to finacial and time freedom?

Expect to learn what your starting goals should look like so that you avoid as many investing pitfalls as possible and who you need to become in order to play the real estate game for the longer term.

📜FREE Purchase & Sales Agreement: https://go.reiautomated.io/strongest-psa-lm

📊FREE Deal Analyzer + Repair Estimator: https://go.reiautomated.io/deal-analyzer

🖥️FREE First Deal Fast-Track Webinar: https://www.firstdealfasttrack.com/register

📃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

Chapters

00:00 Introduction to Real Estate Investing Podcast
07:31 The Significance of Proof in the First Deal