Keith Gillispie: From Marine Corps to Real Estate Empire Builder
In this episode of Better Business, Better Life, host Debra Chantry-Taylor is joined by Keith Gillispie, co-founder of REI Automated, who shares his powerful journey from serving in the Marine Corps to building a multi-state real estate empire.
Keith opens up about the discipline and systems mindset he developed in the military, and how that foundation shaped his approach to business. From investing in 34 states to raising over 10 million dollars and helping more than 400 students pursue financial freedom, Keith credits much of his success to one thing: simple, clear, documented systems.
The conversation explores the critical role of Standard Operating Procedures in scaling a business, why clarity beats complexity, and how strong systems create both freedom and resilience. He also shares the reality of overcoming significant personal debt, the pressure of entrepreneurship, and how coaching and accountability helped him turn things around.
This episode is a practical and inspiring look at how structure, principles, and leadership discipline can transform both business and life.
Keith also generously offers his real estate courses free to podcast listeners, making this an episode packed with both insight and opportunity.
CONNECT WITH DEBRA:
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►Debra Chantry-Taylor is a Certified EOS Implementer | Entrepreneurial Leadership & Business Coach | Business Owner
►Connect with Debra: debra@businessaction.com.au
►See how she can help you: https://businessaction.co.nz/
►Claim Your Free E-Book: https://www.businessaction.co.nz/free-e-book/
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GUEST’s DETAILS:
► LinkedIn Profile: https://www.linkedin.com/in/keith-gillispie/
► Website: www.reiautomated.io
Episode 260 Chapters:
00:00 – Keith Gillispie’s Journey from Marine Corps to Real Estate Empire
06:24 – Transition to Real Estate and Building Systems
12:17 – The Role of Systems in Personal and Business Life
24:23 – Challenges and Successes in Business Growth
29:32 – Implementing EOS and Principle-Based Decision Making
47:41 – Keith’s Free Real Estate Courses for Listeners
She is based in New Zealand but works with companies around the world.
Her passion is helping Entrepreneurs live their ideal lives & she works with entrepreneurial business owners & their leadership teams to implement EOS (The Entrepreneurial Operating System), helping them strengthen their businesses so that they can live the EOS Life:
- Doing what you love
- With people you love
- Making a huge difference in the world
- Bing compensated appropriately
- With time for other passions
She works with businesses that have 20-250 staff that are privately owned, are looking for growth & may feel that they have hit the ceiling.
Her speciality is uncovering issues & dealing with the elephants in the room in family businesses & professional services (Lawyers, Advertising Agencies, Wealth Managers, Architects, Accountants, Consultants, engineers, Logistics, IT, MSPs etc) - any business that has multiple shareholders & interests & therefore a potentially higher level of complexity.
Let’s work together to solve root problems, lead more effectively & gain Traction® in your business through a simple, proven operating system.
Find out more here - https://www.eosworldwide.com/debra-chantry-taylor
