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Hosted by Keith Gillispie · 🇺🇸 US · EN · 44 episodes
Established thought leaders with verified media credentials.
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.
Keith Gillispie hosts First Deal Podcast, a business show with 44 episodes published.
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 t
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 mid-t
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
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 redef
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 ask
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 emba
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
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, and
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, pers
Keith lays out his three-step deal analysis framework — the same process he uses on every property regardless of location, price point, or condition. Then he breaks down where short-term rentals actually stand right now
Keith gets honest about the parts of real estate investing that never make it into the books — the emotional weight, the relentless learning curve, and the reality that most people aren't built for entrepreneurship. Then
Keith tackles four foundational questions every beginner real estate investor eventually asks: Is house hacking actually worth it? What do you do with $100K starting out… and what if you have nothing? How many units does
Keith sits down with Houston-based real estate investor Michael H. to trace his full journey — from traveling every week for a soul-draining corporate telecom job to building a portfolio across multiple strategies. Micha
Keith breaks down the single most common mistake that kills deals in negotiations, shares his exact cold-call opening line, and explains why the word "if" is quietly sabotaging your seller conversations. Plus a real stor
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,
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
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 a
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 industr
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 fin
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,
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First Deal Podcast is hosted by Keith Gillispie. The show is categorised under business (investing) and has published 44 episodes.
First Deal Podcast has published 44 episodes.
First Deal Podcast regularly covers business, investing. It sits in the business category, with a investing focus.
First Deal Podcast is accessible for guests with genuine business expertise. A personalised, episode-aware pitch will still outperform a generic one every time.
First Deal Podcast hasn't explicitly signalled guest openness in recent episodes. That doesn't rule out pitching. your hook just needs to be especially compelling and relevant to their recent content.
Episodes of First Deal Podcast average 29 minutes. a focused format where a clear narrative arc and tight preparation matter most.
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