First Deal Podcast

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 ho...

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 exp...

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...

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 h...

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...

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, K...

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, an...

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 en...

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 h...

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 abi...

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 r...

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 in...

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 significantly Mobile homes offer high cash on cash return and f...

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-term rentals, admitting it stumped him more than almost any question Dayton has asked. Takeaways Diversify in the right order: strategy first, geography second, asset class last. Ge...

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 makes a bold case for why 99% of investors should be investing somewhere other than where they live Takeaways The Two Learning Curves Nobody Warns You About How to Find an Investor...

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 redefines what "safe" actually means in real estate — and it has nothing to do with the price of the house. Takeaways Is Creative Financing Real or Internet Hype? How to Find Real Lende...

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 asking price. Then he shares the exact leverage percentage he never crosses in his portfolio, backed by 30 years of metro-level data going all the way back to 2008. Takeaways How to U...

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 embarrassing truth about how many houses he kept in his first eight years, and defines what a good deal looks like in today's uncertain market. Takeaways Wholesaling offers quick cash...

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 renovation photos to siphon off $15,000 out of a deal. Takeaways Underestimating repair costs Overestimating ARV Ignoring holding costs Chapters 00:00 Introduction 02:19 Common Und...

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 reveals the single system that had a bigger impact on his business than anything else he's ever implemented. Takeaways Real estate investment strategies Importance of lead connect...

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, personal answer to what financial freedom actually looks like in his day-to-day life — and whether it matched what he imagined when he started. Takeaways Why inbound marketing is worth...

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 and what killed his own STR business in Hawaii. He closes with the two numbers investors almost always underestimate on a fix and flip, and why getting them wrong is so costly.  Ta...

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 he breaks down the single family vs. multifamily debate and ends with a blunt answer to the question every new investor secretly asks: how do I know when I'm actually ready? Takea...

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 it take to go full-time? And should you buy your first home or keep renting and invest elsewhere? His answers are direct, occasionally controversial, and grounded in a decade of r...

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. Michael shares why the BRRRR method no longer works in his market, how he stumbled into mobile home land packages with 60–90K profit margins, and what he actually believes generational...