business
Hosted by Keith Gillispie · business · EN
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.
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Contact path
Verified email
Booking probability
33%
Guest openness
Selective
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Signup to Generate a PitchYour 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.
First Deal Podcast is hosted by Keith Gillispie. The show has published 56 episodes to date.
Recent episodes include "#56 - Retired After 32 Years, Then Said Yes to a $1M Raise with Stacey & Ja’el T." (26 October 2026, 69 minutes), "#55 - Before Any DSCR Loan, Run This Stress Test with Lorillia P." (19 October 2026, 39 minutes), and "#54 - He Only Works 2 Hours a Week on 43 Short-Term Rental Units with Kirby A" (19 October 2026, 38 minutes).
First Deal Podcast publishes roughly weekly, with episodes averaging 32 minutes across 56 episodes.
Booking probability for First Deal Podcast is 33%, and the host is rated Selective on guests. First Deal Podcast requires a Pod Score of 80 or higher. First Deal Podcast's contact route on record: verified email.
The strongest fits for First Deal Podcast are Property Management & Appraisal and Landlords & Property Leasing. First Deal Podcast has a business audience and around 240 subscribers on YouTube.
Keith Gillispie hosts First Deal Podcast, a business podcast with 56 episodes published.
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Episode #56
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...
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...
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...
Episode #53
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...
Episode #52
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...
First Deal Podcast
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...
Episode #50
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...
Episode #49
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...
Episode #48
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...
Episode #47
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...
Episode #46
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...
Episode #44
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...
Episode #43
Keith breaks down portfolio diversification across three dimensions — strategy, geography, and asset class — and explains why most people get the order completely wrong. Then he gives his most nuanced answer yet on...
Episode #42
Keith breaks down the two learning curves that hit every new investor — information overload and the character trait nobody warns you about. Then he shares exactly when and why you need an investor-friendly realtor, and...
Episode #41
Keith breaks down why creative financing is his favorite strategy in today's market, shares a real story about a client who got scammed out of $27,000 by a fake hard money lender, and ends with a mindset shift that...
Episode #40
Keith does a live walkthrough inside Deal Labs to show exactly how he's finding and underwriting deals in a high interest rate environment — including the counterintuitive strategy of offering sellers more than their...
Episode #39
Keith gives his most honest take yet on wholesaling — what it actually is, what it isn't, and who it's right for. Then he breaks down the cash flow vs. appreciation debate using order of operations logic, shares the...
Episode #38
Keith draws from over 1,500 deals underwritten in office hours alone to break down the three numbers that consistently destroy fix and flip profits — and shares a real client story about a contractor who used AI to fake...
Episode #37
Keith opens up his actual portfolio and breaks down what he'd sell, what he's keeping forever, and what he's aggressively buying more of. Then he calls out the tax trap most investors don't see coming on whole tails...
Episode #36
Keith reflects on what he'd do differently if he were rebuilding his portfolio from scratch, calls out the most dangerous piece of conventional wisdom still circulating in real estate investing, and gives an honest...
Recent guests on First Deal Podcast. Study who booked and why before you pitch.
PitchCentric classifies First Deal Podcast under these industries. Guests from them are the closest fit, and each links to the best podcasts in that industry.
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