Real Estate Rookie

Real Estate Rookie

Ready to build your real estate empire… but not sure where to begin? Think of us as your personal trainer. From detailed breakdowns of real-world deals… to one-on-one coaching sessions and a warm, welcoming community… hosts Ashley Kehr and Tony J Robinson bring on a wide range of guests to tackle the “newbie” questions you've wondered about but might be afraid to ask. Looking to 10X your real estate investing business this year? This show isn’t for you. Looking for your first, second, or third deal -- or envisioning a more modest portfolio? Step right up. Every Monday, Wednesday and Friday, we’ll arm you with the tips, tools, and roadmaps you'll need as you embark on your journey toward financial freedom.

Episodes

Making $25,000/Year Cash Flow by Buying the Worst Rental on the Best Block

January 12, 2026 • 51 mins
Getting laid off from your W2 job can be a crushing blow, but for today’s guest, it was the push she needed to finally bet on herself. Her first “real” rental property wasn’t the perfect deal, but it didn’t need to be. Today, it cash flows over $25,000 a year and has become her favorite creative outlet! Welcome back to the Real Estate Rookie podcast! Where you invest is often just as important as the property itself, so when Ale...
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How to Buy Cash-Flowing Rentals in 2026 (Despite High Rates) (Rookie Reply)

January 9, 2026 • 33 mins
Is real estate investing still worth it? High mortgage rates and home prices can make buying a rental property seem challenging, if not impossible at times, particularly for a rookie investor with zero experience. But not to worry—in this episode, we’re sharing beginner-friendly tips that will help you find and fund cash-flowing deals in 2026!   Welcome to another Rookie Reply! We’re back with three questions from the BiggerPocke...
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Why Landlord Insurance Premiums Are Skyrocketing in 2026 (And How to Stop It)

January 7, 2026 • 34 mins
Landlord insurance premiums are rising fast in many markets across the U.S., and if you’re not careful, this expense could be a dealbreaker on your next rental property. Fortunately, we know an expert on this topic, and in this episode, he’ll help you navigate these challenges so you buy the right policy without sacrificing your cash flow! Welcome back to the Real Estate Rookie podcast! Today, we’re joined by Darren Nix, CEO of ...
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She Quit Her W2 to Stay Home, Now This Mom of 3 Makes $6K/Month from 1 Rental

January 5, 2026 • 56 mins
“Cancer.” One word would change this mom’s life forever, requiring her to drop her career and become a full-time caregiver. But little did she know that real estate investing would bring her more time, flexibility, and freedom than she had at any W2 job. Today, she owns several rentals, including one that brings in over $6,000 in monthly cash flow! Welcome back to the Real Estate Rookie podcast! Jane Ng and her husband had been ...
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Deal of a Lifetime? How to Structure a Win-Win Seller Financing Deal (Rookie Reply)

January 2, 2026 • 24 mins
Money is often the biggest barrier standing between a rookie investor and their first deal, but there’s a creative way to buy a rental property that doesn’t require draining your savings or putting much down at all. We’re talking about seller financing. In today’s market, you may have even more leverage to negotiate these kinds of deals. Tune in as we break one of them down!   Welcome to another Rookie Reply! We’re back with more...
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How to Buy Your First Rental Property (7 Steps)

December 31, 2025 • 38 mins
Tired of spending your money on rent or stashing it in a traditional savings account? You could make your money work harder for you and get on the path to financial freedom with real estate investing. Today, we’re going to show you exactly how to buy your first rental property in 2026, step by step!   In this episode, Ashley and Tony are going to show you seven steps that will get you off the sidelines and into the game! First, w...
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How to Build Your 2026 Real Estate Investing Plan

December 29, 2025 • 39 mins
By the time you finish this episode, you’ll have your exact plan for financial freedom through real estate, starting in 2026.  See if you can answer these questions right now: How much money do you want to make every month? When do you (realistically) want to retire? How much real estate will it take to get there? And which strategy will actually get you to the finish line? If you can’t answer all four of those questions, you...
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The 4 Best Types of Rental Properties for NEW Investors to Buy

December 26, 2025 • 40 mins
So, you want to invest in real estate…but where should you start? What’s the best type of rental property for a beginner? It’s easy to become overwhelmed by all the options, but in this episode, we’ll provide the four-step framework you need to make the right choice! Welcome back to the Real Estate Rookie podcast! First, we’ll share four steps that will help you pin down the right investing strategy for your budget, lifestyle, a...
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Redfin: The Great Housing Market “Reset” Starts in 2026

December 24, 2025 • 40 mins
Redfin just called it. The housing market will “reset” in 2026…or at least it’ll be the start of it. Chen Zhao, Redfin's head of economics research, has 11 predictions she and her team have formulated for the 2026 housing market. A long, slow period of progress could be upon us, as buyers get what they’ve been asking for: better affordability, a more normal market, and the chance to own where there’s work.  But what does this...
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Waiter to Financial Freedom with 5 Rentals and $5,000/Month Cash Flow

December 22, 2025 • 35 mins
Think you can’t create cash flow in this housing market? Think again! Today’s guest will introduce you to a strategy that can take a regular rental property and maximize its profits. It’s allowed him to net $5,000 each month and quit his W2 job in just 18 months! Welcome back to the Real Estate Rookie podcast! Just two years ago, Andres Martinez was waiting tables and saving every penny possible for a house. But when he was told...
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Buying a “Cheap” Rental Property: What 99% of Rookies Miss (Rookie Reply)

December 19, 2025 • 27 mins
We’ve all come across that property—the one with the irresistibly low price in the bad area of town. The numbers make it look like a home-run real estate deal, but are there too many red flags to ignore? We’ll show you exactly what to do when analyzing this type of rental property!   Welcome back to another Rookie Reply! We’ve pulled three new questions from the BiggerPockets Forums, and first up, an investor wants to know whethe...
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This Online Side Hustle Pays for My Rentals (And Could Fund Your First Deal)

December 17, 2025 • 53 mins
Many rookies would invest in real estate if only they had the money. Well, we’re about to share a simple, scalable side hustle that could help you save money and buy your first rental property much faster. Today’s guest has built up this type of small business multiple times over the last six years, and in this episode, he’ll show YOU how to do the same! Welcome back to the Real Estate Rookie podcast! Cody Berman had dabbled in ...
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Making $1,200/Month by Turning His Home Into a Cash-Flowing Rental

December 15, 2025 • 30 mins
Think you need a big bank account to invest in real estate? You don’t! There are several ways to either buy a rental property with low money down or turn an existing property into a rental with even less money out of pocket. Just ask today’s guest, whose first property now gives him an extra $1,200 in monthly cash flow! Welcome back to the Real Estate Rookie podcast! For years, Alex Bozzy had wanted to get into real estate inves...
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How to Find Great Real Estate Deals in 2026 (Before Anyone Else) (Rookie Reply)

December 12, 2025 • 25 mins
Not knowing the difference between a “good” real estate deal and a “bad” one keeps many rookies on the sidelines. If this is the one hurdle preventing you from buying your first rental property, don’t worry—today’s episode will give you the confidence to find, analyze, and buy a great deal in 2026!   Welcome back to another Rookie Reply! We’ve got three new questions from the BiggerPockets Forums, the first of which comes from so...
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I Built a Real Estate Business That Replaced My High-Paying W2 (Here’s How)

December 10, 2025 • 37 mins
Many rookies assume it’s easier to buy a rental property in their own market, but today’s guest proved you don’t need to by taking down his first deal in another area of the country, sight unseen. And good thing he did, because it not only pocketed him $250,000 but also gave him the confidence to leave his W2 job, move to another country, and go all in on real estate investing! Welcome back to the Real Estate Rookie podcast! Ste...
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He “Stacked” 5 Properties in 6 Years: Now He Lives and Travels for Free!

December 8, 2025 • 45 mins
Most rookies buy rental properties for monthly cash flow or long-term appreciation, but for today’s guest, the enormous tax benefits were the biggest driver. Whether you’re looking to achieve true financial freedom, leave your W-2 job, or keep more of your hard-earned money from the tax man, this episode is for you! Welcome back to the Real Estate Rookie podcast! Ross Alcorn was very good at his medical sales job, but he was slo...
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Inheriting Tenants: Instant Cash Flow or Huge Headache? (Rookie Reply)

December 5, 2025 • 30 mins
Forming a real estate investing partnership could help you scale your real estate portfolio faster, but if you’re not careful, you could just as easily find yourself in hot water. Want to make sure you structure your partnership in a way that protects you and your assets? Then you won’t want to miss this episode!   Today’s Rookie Reply features more questions from the BiggerPockets Forums and answers from your trusted hosts, Ashl...
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How to Find High-Cash-Flow Vacation Rentals Using “Secret” Airbnb Data

December 3, 2025 • 66 mins
Are we seeing a short-term rental resurgence? Since Airbnb’s big boom in 2021, many investors have shied away from the “oversaturated” short-term rental industry. But is now actually the ideal time for you to buy vacation rentals? Today’s guests believe there’s more opportunity than you might think! Welcome back to the Real Estate Rookie podcast! Today, we’re joined by Jamie Lane of AirDNA and John Bianchi of STR Search, who are...
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45 Rentals and $0 Debt: The Money Mindset Shift That Made Me Financially Free

December 1, 2025 • 39 mins
Worried you’ll never be able to buy rental properties because you’re “bad” with money? Today’s guest was in the same boat until a much-needed mindset shift set her on the path towards financial freedom. Since then, she has built a debt-free, 45-property portfolio that gives her more than enough cash flow to live on! Welcome back to the Real Estate Rookie podcast! Liz Carroll didn’t always have a healthy relationship with money. ...
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Local vs. Out-of-State Investing: Where to Buy Your First Rental (Rookie Reply)

November 28, 2025 • 28 mins
Before you buy a rental property, you’ll need to decide where to invest. Some rookies feel more comfortable investing in their own backyards, while others prefer to handpick a market that will give them enough cash flow or appreciation to reach their long-term goals. But which one will give YOU an advantage?   Welcome to another Rookie Reply! Today, Ashley and Tony are tackling more questions from the BiggerPockets Forums. First,...
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