First Deal Podcast

Keith Gillispie
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  • Investing

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.

  1. Sep 9

    #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 specialistWhy every recurring task should have a documented SOPWhy you shouldn't expect an employee to create your business systems for youHow Keith developed his personal 55% maximum portfolio leverage rule and how you can use it tooWhy Keith believes paying 10% for excellent property management is worth itWhy 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  📜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  SOCIALS Instagram: https://www.instagram.com/keithg_rei/  Facebook: https://www.facebook.com/Keith.Gillispie Music from #Uppbeat (free for Creators!): https://uppbeat.io/t/monobox/backbone License code: OZZJFTOT1V6EYPPY

  2. Sep 4

    #50 - The Real Reason Your Real Estate Business Stops Growing

    In this episode of The First Deal Podcast, Dayton Lindsey sits down with Keith Gillispie to break down the progression from residential real estate into multifamily and commercial investing. They discuss the different paths investors can take after single-family properties, economies of scale in multifamily, why commercial brokers matter, how commercial deals are underwritten, seller financing, and why Keith believes parts of commercial real estate can actually be simpler than residential investing. Keith also breaks down what happens operationally as a real estate business grows. He explains how managing too many direct reports became a major bottleneck, why Traction and the EOS framework changed the way he managed his teams, how automation helped reduce his sales team from 18 reps to three while increasing throughput, and why every period of “stabilization” may actually be a sign that you've hit your next core constraint. Takeaways Transition from residential to commercial real estateThree types of real estate investors Effective communication is crucial for scaling a businessIdentifying and addressing core constraints is essential for sustained growth Chapters 00:00 Introduction00:48 The Transition from Residential to Commercial Real Estate04:11 Understanding Multifamily Investments09:44 The Learning Curve in Commercial Real Estate15:31 The Collaborative Nature of Commercial Real Estate20:44 Operational Challenges in Scaling Investments21:33 Navigating Team Dynamics and Communication28:00 The Importance of Stabilization in Growth39:51 Identifying and Overcoming Core Constraints43:10 Outro 📜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  SOCIALS Instagram: https://www.instagram.com/keithg_rei/  Facebook: https://www.facebook.com/Keith.Gillispie Music from #Uppbeat (free for Creators!): https://uppbeat.io/t/monobox/backbone License code: OZZJFTOT1V6EYPPY

  3. Sep 2

    #49 - The Real Estate Deal Keith Couldn't Save

    In this episode of The First Deal Podcast, Dayton Lindsey sits down with Keith Gillispie to talk about the real estate deals and business decisions that don't go according to plan. They break down a foreclosure deal Keith couldn't save, what “passive income” actually looks like with rentals and promissory notes, the role of property and note management, the moments that nearly took Keith out of entrepreneurship, and why financial management matters as your business grows. Keith also opens up about spending more than $250,000 on mentorship during his first four years, carrying as many as 22 credit cards, and later spending roughly $25,000–$30,000 per month on advertising while scaling a business whose numbers he couldn't properly see. He explains how poor execution, unchecked expenses, and high-interest debt became some of his most expensive lessons—and why taking action on what you learn matters more than endlessly consuming more information. Takeaways Real estate investing challengesPassive income from real estateDealing with bad debt Chapters 00:00 Introduction00:48 Real Estate Challenges09:48 Understanding Passive Income in Real Estate14:40 Overcoming Obstacles in Real Estate Investing29:38 Final Thoughts and Key Takeaways31:01 Outro 📜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  SOCIALS Instagram: https://www.instagram.com/keithg_rei/  Facebook: https://www.facebook.com/Keith.Gillispie Music from #Uppbeat (free for Creators!): https://uppbeat.io/t/monobox/backbone License code: OZZJFTOT1V6EYPPY

  4. Aug 28

    #48 - How to Build a Business With Your Spouse Without Destroying Your Marriage

    In this episode of The First Deal Podcast, Dayton Lindsey sits down with Keith Gillispie to talk about working with your spouse in real estate, dividing responsibilities inside the business, getting aligned on goals and risk, choosing the right mentors and books, and avoiding productivity habits that make you feel busy without actually making progress. Keith shares lessons from working alongside his wife, Miranda, during the early years of his real estate career — including why cross-training matters, how they divided responsibilities based on strengths, and the one rule he believes has to stay above everything else Takeaways: When considering real estate investing with a spouse, it's crucial to align visions, communicate effectively, and prioritize the marriage over the business.Recommended books, mentors, and communities can provide valuable insights and guidance for personal and professional development.Why spouses should be cross-trained even when they have separate primary roles  Chapters: 00:00 Introduction 00:48 Sickness Stories and Resilience 01:04 Mindset in Real Estate Investing 02:09 Working with Spouses in Business 08:03 Aligning Visions and Goals 12:15 Influential Books and Mentorships 21:06 Prioritizing Productivity Over Routine 25:27 Outro 🎁Goal Setting For Couples:  https://knowledge.reiautomated.io/courses/self-mastery  📜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  SOCIALS Instagram: https://www.instagram.com/keithg_rei/  Facebook: https://www.facebook.com/Keith.Gillispie Music from #Uppbeat (free for Creators!): https://uppbeat.io/t/monobox/backbone License code: OZZJFTOT1V6EYPPY

  5. Aug 26

    #47 - Financial Freedom Isn't About Money... It's About THIS

    In this episode of The First Deal Podcast, Dayton Lindsey sits down with Keith to talk about what financial freedom looks like after a decade of investing, why people get stuck preparing to invest for years without taking action, and how Keith thinks about real estate within a much larger wealth-building strategy. Keith explains why he now thinks of financial freedom as “choice freedom” — the ability to decide what to do, when to do it, who to do it with, and how long to do it. From there, the conversation moves into family, entrepreneurship, investing, sales, diversification, and the three things Keith believes almost every struggling new investor is missing: education, systems, or support. Takeaways Mindset is key to achieving financial freedomFinancial freedom is about choice freedom, not just moneyReal estate is a key wealth-building asset Chapters 00:00 Introduction00:48 The Essence of Financial Freedom08:41 Evolving Perspectives on Wealth15:53 Taking Action in Real Estate Investing17:25 Integrating Real Estate with Broader Wealth Strategies24:27 The Path to Millionaire Status25:32 Outro 📜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 Music from #Uppbeat (free for Creators!): https://uppbeat.io/t/monobox/backbone License code: OZZJFTOT1V6EYPPY

  6. Aug 21

    #46 - Which Retirement Account Is Best For Real Estate Investors To Invest With?

    In this episode of The First Deal Podcast, Dayton Lindsey and Keith Gillispie break down how Keith thinks about self-directed retirement accounts, Solo 401(k)s, DSCR loans, private money, leverage, and funding your next several deals without waiting years to stockpile cash. Keith explains why he strongly prefers a self-directed Roth Solo 401(k) over an IRA for his own investing, how he has used retirement-account funds for earnest money deposits, and why he believes investors need qualified professionals in their corner before making decisions involving retirement accounts or taxes. Takeaways Self-directed IRAs and solo 401(k)s offer benefits for real estate investmentDSCR loans and private money raising strategies are crucial for funding real estate deals Chapters 00:00 Introduction00:48 Understanding Self-Directed IRAs and Solo 401(k)s05:39 The Benefits of Solo 401(k)s Over IRAs11:26 Exploring Health Savings Accounts (HSAs) and Tax Benefits17:21 The Importance of Debt Service Coverage Ratio (DSCR) Loans23:42 Capital Stacking Strategies for Real Estate Investing28:39 Outro 📜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 Music from #Uppbeat (free for Creators!): https://uppbeat.io/t/monobox/backbone License code: OZZJFTOT1V6EYPPY

  7. Aug 19

    #45 - The $1.8M Deal Keith Walked Away From (And Why It Was the Right Call)

    In this episode of The First Deal Podcast, Dayton Lindsey sits down with Keith Gillispie to talk about risk, leverage, passive investing, and the importance of knowing when not to force a deal. Keith starts with the story of a massive oceanfront property in Kailua, Hawaii that he had under contract for roughly $1.8 million, with a potential ARV north of $3 million. On paper, the spread looked incredible. In reality, uncertain comps, structural problems, mold and water damage, and potentially hundreds of thousands of dollars in renovations made the downside impossible to ignore. Takeaways Risk AversionPassive Investing Chapters 00:00 Introduction00:48 The Biggest Deal Keith Has Ever Walked Away From11:54 Understanding Real Estate Syndications16:54 Refinancing Properties for Equity24:52 Tax Strategies and Real Estate Investing33:04 Outro 📜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  🌐Our Website: https://www.reiautomated.io  🎯DealBase - The Only CRM Built For Real Estate Investors: https://go.reiautomated.io/dealbase-reia   🌟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 Music from #Uppbeat (free for Creators!): https://uppbeat.io/t/monobox/backbone License code: OZZJFTOT1V6EYPPY

  8. Aug 14

    #44 - How To Make MORE Money WITHOUT Buying More Houses

    In this episode of The First Deal Podcast, Dayton Lindsey sits down with Keith Gillispie to break down several real estate strategies investors may overlook — including co-living and rent-by-the-room rentals, choosing the right market, and investing in mobile and manufactured homes. Takeaways Rent by room strategy increases cash flow significantlyMobile homes offer high cash on cash return and financing opportunities Chapters 00:00 Introduction00:48 Exploring Rent by Room Strategies09:05 Market Evaluation for Real Estate Investments16:01 Insights on Mobile Home Parks and Manufactured Housing23:00 Outro 📜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  🌐Our Website: https://www.reiautomated.io  🎯DealBase - The Only CRM Built For Real Estate Investors: https://go.reiautomated.io/dealbase-reia   🌟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 Music from #Uppbeat (free for Creators!): https://uppbeat.io/t/monobox/backbone License code: OZZJFTOT1V6EYPPY

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About

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.

Information

  • Creator
    Keith Gillispie
  • Years Active
    2026
  • Episodes
    51
  • Rating
    Clean
  • Copyright
    © 2026 Keith Gillispie