First Deal Podcast

Keith Gillispie
  • 0.0 (0)
  • 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. 4d ago

    #56 - Retired After 32 Years, Then Said Yes to a $1M Raise with Stacey & Ja’el T.

    Stacey T. spent 32 years at a Fortune 50 company, managing customer care centers of more than 300 people with the federal government as her client. After retiring, she built Eminent Estates with her daughter, Ja’el T., who runs the numbers while Stacey finds the money. They share the hard lessons from a 2006 Baltimore triplex, the $10K creative finance deal that came from one Facebook post, and how a BiggerPockets conference led to their first capital raise, when an operator came up $1M short on an 87-unit student housing deal and they said yes to bringing it. They also explain why they now focus on residential assisted living. Guests * Stacey Thomas is a co-founder of Eminent Estates, a capital raiser, and a retired corporate leader with 32 years at a Fortune 50 company. * Ja’el Thomas is a co-founder of Eminent Estates, a licensed real estate agent, and the one who underwrites their deals. Where to find Stacey and Ja’el * Website: https://eminentestates.net * Eminent Estates YouTube: https://youtube.com/@_eminentestates * Eminent Estates LinkedIn: https://www.linkedin.com/in/eminentestates/ * Ja’el’s YouTube: https://youtube.com/@_jael.thomas * Ja’el’s Instagram: https://instagram.com/_jael.thomas * Stacey’s Instagram: https://instagram.com/sta_exclusive Takeaways * Research the location and partner with someone experienced before you buy your first property. * Keep your job until your real estate income can replace it. * When a deal goes wrong, keep taking action instead of getting stuck. Chapters * 00:00 Introduction * 01:06 32 Years in Corporate America * 04:14 The 2006 Baltimore Triplex * 10:12 Ja’el’s Path to Real Estate * 12:09 Starting Eminent Estates * 13:59 A $10K Deal From One Post * 17:43 Saying Yes to a $1M Raise * 20:07 Lessons From the Early Years * 26:25 Systems That Do the Work * 27:22 Why Assisted Living * 29:38 Why Pay for a Mentor * 34:25 Advice for Every Stage * 39:42 Lightning Round * 45:46 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

  2. Oct 19

    #55 - Before Any DSCR Loan, Run This Stress Test with Lorillia P.

    Lorillia P. started her career as an auditor at Deloitte, one of the biggest accounting firms in the world, and not long after college she had debt collectors calling. Today she advises real estate investors on financing, and she sat down with Keith to talk about how much debt is too much. Lorillia explains how to stress test a deal before you borrow, using a three-unit example where $9,000 in expected rent drops to $3,000 against an $8,000 debt payment. She also shares why using business funding for your down payment is the worst advice gurus keep repeating, why chasing the lowest rate can cost you in fees, and how she started out wholesaling bank-owned homes in 2008. Guests * Lorillia Phillips is a former Deloitte auditor, tax firm founder, real estate investor, and the financing advisor behind Never Lose a Deal. Where to find Lorillia * Website: https://neverloseadeal.com/ * Financing Term Sheet: https://funds.neverloseadeal.com * Facebook: https://www.facebook.com/lorilliaphillips/ * LinkedIn: https://www.linkedin.com/in/lorilliabrownphillips/ * YouTube: https://www.youtube.com/user/lorilliabp * TikTok: https://www.tiktok.com/@lorilliabphillips Takeaways * Before you borrow, run a worst case where tenants leave or stop paying, and make sure you can still cover the debt. * Using short-term, high-interest debt for a down payment can wipe out the cash flow on a long-term rental. * Choose a lender who asks about your goals, because a lower rate can come with higher fees elsewhere. Chapters * 00:00 Introduction * 00:54 From Rutgers to Deloitte * 03:02 How the Debt Piled Up * 06:46 Starting Her Own Tax Firm * 12:37 Her First Wholesale Deal * 17:03 The Lender Who Never Asked * 20:08 Ally or Archenemy * 21:48 Buying When Rates Are High * 25:01 The Debt Stress Test * 29:58 Copying Guru Financing * 33:52 Advice for First-Time Buyers * 36:21 Lightning Round * 38:16 Final Takeaway * 39:15 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

  3. Oct 19

    #54 - He Only Works 2 Hours a Week on 43 Short-Term Rental Units with Kirby A

    In 2006, a young Army officer at Fort Bliss saw a for-sale sign across the street and walked over in his uniform to buy the house before the owners had even set a price. Twenty years later, Kirby A. runs 43 short-term rental units from a hobby farm in northern Indiana while working about two hours a week, and he sat down with Keith to explain how he got there. Kirby shares why he traded the gross 1% rule for a property that nets 1% of the purchase price every month, walks through the real numbers on a $425K three-unit he expects to net just over $4,000 a month, and explains why flipping about 70 houses in Chicago left him right where he started. Guests * Kirby Atwell is a West Point grad, former Army officer, short-term rental investor, and host of Living Off Rentals. Where to find Kirby * Free Web Class: https://livingoffrentals.com/start * Facebook Page: https://www.facebook.com/LivingOffRentals * YouTube: https://www.youtube.com/channel/UCRpWXe2mWqBm5vvbO2R2AdA * Instagram: https://www.instagram.com/kirbyatwell/ Takeaways * Run every deal on net cash flow, because gross rent can hide a property that costs you money. * Small multi-units outside big cities can out-earn vacation homes in tourist markets. * Get clear on the life you want 10 years from now, with your spouse, before you pick a strategy. Chapters * 00:00 Introduction * 02:18 His First Rental on Active Duty * 05:28 From El Paso to Flipping in Chicago * 07:30 Why 70 Flips Weren't Enough * 09:29 From 1% Gross to 1% Net * 13:39 The Real Numbers on a Three-Unit * 17:04 Self-Managing With a Virtual Team * 19:01 Saving for Repairs and CapEx * 20:28 43 Listings From a Hobby Farm * 23:27 Advice for Active Duty * 28:11 Vision Casting With Your Spouse * 30:57 Lightning Round * 35:28 Final Takeaway * 36:56 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

  4. Sep 22

    #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 📜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. Sep 18

    #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 systemWhether it's better to pay a mentor or learn everything through trial and errorWhy Keith views time as a more valuable currency than moneyHow 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  📜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

  6. 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

  7. 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

  8. 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

See All (56)

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
    56
  • Rating
    Clean
  • Copyright
    © 2026 Keith Gillispie