What’s the right investing strategy for YOU? In this episode, we’re going to hear from an investor who has scaled their real estate portfolio to twenty rentals in just TWO years! Despite their rapid success, they feel “stuck” and aren’t sure which strategy to use moving forward. Stay tuned as we show you how to choose the right strategy while helping them get unstuck!

Welcome back to another Rookie Reply! Today, Ashley and Tony are diving into the BiggerPockets Forums and Real Estate Rookie Facebook group to answer more of your recent questions. After showing you how to nail down an investing strategy, we’ll get into landlord anonymity and provide you with several creative ways to protect your personal information from tenants. But that’s not all. We’ll also discuss short-term rental rates and share the dynamic pricing tools we use to find the “sweet spot” for ANY property or market!

Looking to invest? Need answers? Ask your question here!

In This Episode We Cover:

How to nail down the perfect real estate investing strategy for YOU

Creative ways to hide your personal information from tenants

How to return security deposits to tenants (while staying anonymous!)

Determining the ideal nightly rate to charge (for your short-term rental and market!)

Maximizing your Airbnb revenue with the BEST dynamic pricing tools

And So Much More!

Links from the Show

Ashley's BiggerPockets Profile

Tony's BiggerPokckets Profile

Join BiggerPockets for FREE

Real Estate Rookie Facebook Group

Real Estate Rookie YouTube

OpenPhone

Google Voice

PriceLabs

Beyond Pricing

Wheelhouse

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Don’t have a ton of money to invest in rental properties? No problem! You don’t need hundreds of thousands of dollars to start building wealth. Chris Young, a (not-so) rookie investor from Southern California, started with just five percent down. He bought a $500,000 home in pricey Los Angeles for just $25,000 out-of-pocket. Now, Chris has four rental properties, one of which he uses as a vacation home, and hundreds of thousands in equity! Plus, he did it all while working a W2!

Chris knew he wanted to invest in real estate early on. So, when he started his full-time job, he also got his real estate agent license, allowing him to have a backup source of income in case his career didn’t work out. But, thankfully, his real estate has been doing more than alright! He performed a “live-in BRRRR” (buy, rehab, rent, refinance, repeat) on his first property, making him hundreds of thousands in equity, then bought another one!

But, after attending BPCon, Chris knew he needed a true investment property. What gets you monthly cash flow and a vacation home to use whenever you want? A short-term rental! But not everything went as planned—one unlucky event put his entire house out of commission for months! However, Chris is still thrilled that he has bought this property. He shares why he picked its specific market, how he dodged local competition, and did it all with just ten percent down!

In This Episode We Cover:

How to start building your real estate portfolio with just five percent down!

The “live-in BRRRR” strategy that made Chris hundreds of thousands of dollars 

Picking your vacation rental market and why you DON’T want to go where everyone else is

Using a ten percent down second home loan to buy your first short-term rental 

The one very unlucky event that cost Chris $40,000 (you CAN’T avoid it!) 

And So Much More!

Links from the Show

Ashley's BiggerPockets Profile

Tony's BiggerPokckets Profile

Join BiggerPockets for FREE

Real Estate Rookie Facebook Group

Real Estate Rookie YouTube

Grab the Book, “Short-Term Rental, Long-Term Wealth”

Find Investor-Friendly Lenders

Real Estate Rookie 486 - Quitting His Job with Real Estate After Cracking the Cash Flow Code w/Miller McSwain

Connect with Chris

(00:00) Intro

(02:24) 5% Down First Property

(06:57) Property 2 (Rent-by-Room)

(11:04) Finding 1st Short-Term Rental

(19:36) 10% Down Sequoia Vacation Rental

(29:26) Losing $40K!

(30:01) Setting Yourself Apart

(39:44) Connect with Chris!

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You can make money in real estate—with or without owning rentals! How? There’s a growing segment of the industry that rookies NEED to know about. It’s more lucrative than long-term rentals, more consistent than short-term rentals, and today’s guest is bringing in $1 million a YEAR with it!

Welcome back to the Real Estate Rookie podcast! Jesse Vasquez has mastered the medium-term rental strategy, bringing in over $1 million in revenue each year from twenty-two rentals. But here’s the thing. You don’t need a huge real estate portfolio to use this investing strategy and repeat his success. In fact, you don’t need to own ANY rentals to get started, making it the perfect option for new investors. But make no mistake—you’ll need to roll up your sleeves and get your hands dirty to build this type of real estate business!

In today’s episode, Jesse will show you how to tap into this emerging segment of the market. You’ll learn how to build your network, land your first contract, and become a trusted “broker” for human resource and recruiting companies throughout your market. You’ll also learn the ins and outs of setting up medium-term rentals and how to convert an existing rental property into a thirty-day stay!

In This Episode We Cover:

The corner of the real estate industry that investors are still overlooking

How to set up your own medium-term rental property in 2025

How to build your network, land your first contract, and earn money from referrals

The clients that make the BEST guests (and how to find them!)

Must-have amenities to include with your medium-term rental property

How Jesse makes over $1 million in annual revenue from twenty-two rentals

And So Much More!

Links from the Show

Ashley's BiggerPockets Profile

Tony's BiggerPokckets Profile

Join BiggerPockets for FREE

Real Estate Rookie Facebook Group

Real Estate Rookie YouTube

Buy the Medium-Term Rental Guide “30-Day Stay”

Find an Investor-Friendly Agent in Your Area

How to Invest in Medium-Term Rentals

Connect with Jesse

Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-497

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Are you looking to grow your real estate portfolio and build wealth faster? There’s a tax “loophole” that allows you to sell your property and roll your equity (and profits) into a bigger and better rental property—all while deferring thousands of dollars in taxes. Stay tuned to learn how to use a 1031 exchange to your advantage!

Welcome back to another Rookie Reply! Today, Ashley and Tony are answering some of your recent questions from the BiggerPockets Forums. After discussing 1031 exchanges and “like-kind” properties, we’ll help an investor determine if they should sell or rent a property that, despite the potential to bring in decent monthly cash flow, has some costly capital expenditures looming. Next, is it better to stabilize a rental property by making home improvements that help you raise rent or use the same funds to buy another property? We’ll dive into the numbers and show you which option gives you the highest return!

Looking to invest? Need answers? Ask your question here!

In This Episode We Cover:

The tax “loophole” that allows you to defer thousands of dollars in capital gains tax

Building wealth and growing your portfolio with a 1031 exchange

Whether you should rent or sell a property that needs major repairs

When to stabilize your current portfolio versus buying another property

Prioritizing renovations that increase home value and allow you to raise rents 

And So Much More!

Links from the Show

Ashley's BiggerPockets Profile

Tony's BiggerPokckets Profile

Join BiggerPockets for FREE

Real Estate Rookie Facebook Group

Real Estate Rookie YouTube

Ask Your Question on the BiggerPockets Forums

Put Your Vacation Rental on Autopilot with Hospitable

Ask Your Question for a Future Rookie Reply

Buy “The Book on Tax Strategies for the Savvy Real Estate Investor”

Find Investor-Friendly Lenders

What Is a 1031 Exchange in Real Estate? How to Guide & Examples

(00:00) Intro

(00:46) 1031 Exchanges

(11:50) Should I Rent or Sell?

(18:43) Making Home Improvements

(23:59) Ask Your Question!

Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-496

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Burned out at your W2 job? Tired of climbing the corporate ladder? Starting a real estate business could give you financial freedom, but is it worth giving up the security of a biweekly paycheck? This entrepreneur thinks so, and today, she’ll give you the blueprint for forging your own path in real estate!

Welcome back to the Real Estate Rookie podcast! Melissa Shelton is not only an investor, but also the founder of Dear Valentine, a business that blends luxury, hospitality, development, and management. Quitting her nine-to-five job to become a full-time entrepreneur wasn’t an easy decision since she had worked tirelessly for many years to reach the top of her field. But, in the end, her “why” won out, and she mustered up the courage to go all-in on her dream!

In this episode, Melissa will show you how to launch a “small and nimble” real estate business. You’ll learn how to set goals, grow your clientele from scratch, and build a business plan that keeps you afloat. But that’s not all. Melissa also has tips for limiting overhead costs, finding deals that give the highest returns, and hiring people who propel your business forward!

In This Episode We Cover:

How to start a real estate business that gives you financial freedom

How to get your “foot in the door” and land your first client

Creating multiple income streams that insulate your new business venture

Crafting the perfect “pitch” that gets new investors and partners on board

How to overcome the fear of failure when pursuing entrepreneurship

And So Much More!

Links from the Show

Ashley's BiggerPockets Profile

Tony's BiggerPokckets Profile

Join BiggerPockets for FREE

Real Estate Rookie Facebook Group

Real Estate Rookie YouTube

Ask Your Question on the BiggerPockets Forums

Melissa’s Instagram

Canva

Buy the Book “The Quitter’s Manifesto”

Find Investor-Friendly Lenders

Stay-at-Home Mom to “Accidental” Investor with a $600K/Year Business

Connect with Melissa

(00:00) Intro

(01:40) Catching the Real Estate “Bug”

(04:59) Leaving Her W2 Job

(09:42) Preparing for Entrepreneurship

(21:51) A Day in the Life

(23:37) Melissa’s Business Model

(27:04) How to Find Clients

(35:56) Staying “Small and Nimble”

(39:36) Connect with Melissa!

Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-495

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$50,000 cash flow from ONE rental!? Not many properties will give you this kind of return in today’s housing market, but this investor beat his competition to an innovative investing strategy, and it’s paying huge dividends. Want to find out what it is and how he did it? You don’t want to miss this one!

Welcome back to the Real Estate Rookie podcast! Garrett Brown envisioned himself running restaurants or operating hotels before real estate investing took him down a different path. He got his real estate agent license, flipped a few houses, and then, in a full circle moment, put his background in hospitality to good use—buying three condos at a discount and converting them into short-term rentals. But when Houston, Texas, like many Airbnb markets, became oversaturated in 2021, Garrett landed on a new strategy that would allow him to stand out. It gives vacationers a taste of the great outdoors without sacrificing the luxuries and comfort of a cozy home!

If you want to know how to earn five-figure cash flow from a single rental and keep your vacation rentals booked year-round, stay tuned. We’ll also get into why you should document your investing journey online (even if you’re just starting) and the trick to finding discounted properties!

In This Episode We Cover:

How this investor makes $50,000 in annual cash flow from one rental “unit”

The innovative rental property that blends luxury and the outdoors

How to stand out in any market by offering “unique stays”

Where most short-term rental bookings are coming from in 2025

Why every rookie should document their investing journey on social media

Scoring a deep discount on property by knowing a seller’s motivation

And So Much More!

Links from the Show

Ashley's BiggerPockets Profile

Tony's BiggerPokckets Profile

Join BiggerPockets for FREE

Real Estate Rookie Facebook Group

Real Estate Rookie YouTube

Ask Your Question on the BiggerPockets Forums

Pre-Order the Book “Smarter Short-Term Rentals”

Find Investor-Friendly Lenders

Real Estate Rookie 91 – 8 Units, 10 Wholesale Deals, and $0 Spent on Marketing w/ @liliinvests

Connect with Garrett

(00:00) Intro

(00:53) Agent to Investor

(04:00) Garrett’s FIRST Deal

(09:59) The Motivation to Sell

(14:21) Creating “Unique Stays”

(21:54) Land Hacking 101

(28:04) Permitting Challenges

(32:28) Funding the Dome

(35:42) Cash Flow & Bookings

(44:31) Connect with Garrett!

Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-494

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Many people invest for appreciation. Others invest for tax benefits. But some investors want enough monthly cash flow to replace their W2 income and help them quit their nine-to-five jobs. When can you go full-time with real estate investing? How many rentals do you need? Stay tuned!

Today, Tony and co-host Garrett Brown are diving into the BiggerPockets Forums, and our first question comes from someone who has launched six vacation rentals in just five years. Should they diversify their portfolio? Are they ready to become full-time investors? We’ll share our thoughts! We’ll also hear from someone who’s thinking about selling an equity-rich property to pivot to short-term rentals in the Midwest. Listen in as we show them how to choose a market and set up their Airbnb business. But that’s not all. One investor has bought a rental property that is already booked months in advance. Can they cancel those bookings? Raise their nightly rates? Stick around to find out!

Looking to invest? Need answers? Ask your question on the BiggerPockets Forums!

In This Episode We Cover:

When to leave your W2 job to focus on real estate investing full-time

How to diversify your real estate portfolio without changing your strategy

When to sell your rental property and tap into your home equity

The top factors to consider when analyzing a short-term rental market

How to manage your vacation rental portfolio in five hours per week (or less!)

And So Much More!

Links from the Show

Ashley's BiggerPockets Profile

Tony's BiggerPokckets Profile

Join BiggerPockets for FREE

Real Estate Rookie Facebook Group

Real Estate Rookie YouTube

Ask Your Question on the BiggerPockets Forums

Pre-Order the Book “Smarter Short-Term Rentals”

Find an Investor-Friendly Agent in Your Area

Real Estate Rookie 297 – Traveling the World Thanks to One $6,500/Month Rental Property

Connect with Garrett

(00:00) Intro

(00:36) Diversification & Leaving Your W2

(08:40) Choosing a Vacation Rental Market

(17:52) Managing Short-Term Rentals

(24:58) Airbnb Fees & Using Home Equity

(27:58) Occupancy Rates & Pricing

(33:32) Connect with Garrett!

Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-493

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Do you want to buy a rental property in 2025 but fear money could get in the way? Putting 15%-20% down is a huge hurdle for new investors, but there are several strategies you can use to limit your expenses, grow your income, and even put LESS money down. If you want to know how to save for a down payment as quickly as possible, you need these money-saving tips!

Welcome back to the Real Estate Rookie podcast! Before you can invest in real estate, you need to lay a solid financial foundation, and today, personal finance expert, master live-in flipper, and co-host of the BiggerPockets Money podcast, Mindy Jensen, joins the show to weigh in on this crucial topic. Do you have your spending in check? Are you finding ways to grow your income? How’s your credit score looking?

Whether you’re starting from scratch or looking to level up your finances, we’ll share some actionable steps you can take toward buying property in 2025. We’ll also talk about ways to leverage your retirement accounts to buy real estate, whether you should pay down debt before investing, and other investments (that aren’t real estate) that could help you build wealth!

In This Episode We Cover:

ow to go from ZERO dollars saved to a full down payment for a rental property

Whether you should pay off your debt before investing in real estate

Creative ways to grow your income so that you can save money faster

How to avoid a 20% down payment when buying your first property

Leveraging your retirement accounts to buy passive real estate investments

How to build wealth with other investment vehicles (beyond real estate)

And So Much More!

Links from the Show

Ashley's BiggerPockets Profile

Tony's BiggerPokckets Profile

Join BiggerPockets for FREE

Real Estate Rookie Facebook Group

Real Estate Rookie YouTube

BiggerPockets Money 97 – Intentionally Choosing the Path to Financial Independence with Financial Mechanic

BiggerPockets Money 35 – Hacking Your Life to Live for (Almost) Free with Craig Curelop

Qube Money

Buy the Book “Real Estate Rookie”

Find Investor-Friendly Lenders

BiggerPockets Money 110 – Systematically Increasing Income and Intentionally Decreasing Spending with A Purple Life

Connect with Mindy

(00:00) Intro

(01:13) Laying a Financial Foundation

(06:10) Saving for a Down Payment

(12:58) How to Grow Your Income

(22:59) Other Investment Avenues

(28:24) Leveraging Retirement Accounts

(31:58) Paying Off Debt vs. Investing

(41:07) Connect with Mindy!

Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-492

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When interest rates rose, many investors stopped buying. But not Ryan Irwin. This rookie doubled down on real estate, choosing whichever investing strategy made the numbers work. Even in a tough housing market, Ryan’s big bet on real estate paid off, as he’s now up to seven deals and earns a solid chunk of cash flow each month!

Welcome back to the Real Estate Rookie podcast! It can take a new investor months, sometimes years, to find their first deal. But when Ryan was just starting out, he did the two things every rookie should do: he told everyone he was investing in real estate, and he started attending networking events. Building these relationships has allowed him to buy multiple rental properties, flip houses, and invest in syndications—all in just five years!

But Ryan doesn’t aspire to build his own real estate “empire.” He just wants a small real estate portfolio that gives him financial freedom. Now that he has several deals under his belt, he plans to stabilize his portfolio and squeeze even more cash flow out of his rental properties by refinancing and paying off his mortgages one by one!

In This Episode We Cover:

Why Ryan is doubling down on real estate (even in a tough housing market!)

The number one thing you can do today to fast-track your investing journey

Why a virtual assistant should be your first hire as you scale (and where to find one!)

Two things you can do to increase your rental property cash flow

Chasing financial freedom with a “small and mighty” real estate portfolio

How to scale faster by automating and delegating low-level tasks

And So Much More!

Links from the Show

Ashley's BiggerPockets Profile

Tony's BiggerPokckets Profile

Join BiggerPockets for FREE

Real Estate Rookie Facebook Group

Real Estate Rookie YouTube

Set for Life

The House Flipping Framework

Shop the BiggerPockets Black Friday Sale and Get Up to 60% Off Your Next Book Purchase

Buy the Book “The Small and Mighty Real Estate Investor”

Find Investor-Friendly Lenders

Achieving FI with Fewer Doors: The Small and Mighty Real Estate Portfolio

Connect with Ryan

(00:00) Intro

(01:31)Discovering Real Estate

(07:07) Ryan’s “Lightbulb Moment”

(12:49) Current Portfolio & Funding

(19:03) Key Systems & Processes

(28:56) Cash Flow Numbers

(35:27) Advice for New Investors

(36:23) Connect with Ryan!

Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-491

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Are you leaving cash flow on the table? Even if you own a single rental property, there are all kinds of strategies you can use to generate more rental income, whether it’s house hacking, renting by the room, or converting your long-term rentals to short-term rentals. And we’re just scratching the surface!

Welcome back to another Rookie Reply! Today, we’re diving back into the BiggerPockets Forums to answer some more of your recent questions. First, we’ll hear from someone who’s at a crossroads with their property. This house has paying tenants and consistent monthly cash flow, but the investor would need to sell the property this year to claim it as their primary residence and dodge capital gains taxes. Stay tuned to find out if they should sell or hold! Then, after a few cash-flow-boosting strategies, we’ll discuss using a HELOC (home equity lines of credit) for a down payment and the potential pitfalls you could run into!

Looking to invest? Need answers? Ask your question on the BiggerPockets Forums!

In This Episode We Cover:

How to determine if you should hold or sell your rental property

How to reach your cash flow goals with the fewest properties possible

Creative ways to maximize your rental income on a single property

How to set realistic cash-on-cash return goals for 2024 and beyond

Potential pitfalls to avoid when getting a home equity line of credit (HELOC)

And So Much More!

Links from the Show

Ashley's BiggerPockets Profile

Tony's BiggerPokckets Profile

Join BiggerPockets for FREE

Real Estate Rookie Facebook Group

Real Estate Rookie YouTube

Real Estate Rookie 447 – Making $300K+ Profit Per Rental and Scaling FAST with “DADUs”

Real Estate Rookie 375 – Making $160K/Year From ONE “Rare” Property Thanks to Seller Financing

Protect Your Properties with an LLC Through Corporate Direct

Ask Your Question on the BiggerPockets Forums

Buy “The Book on Rental Property Investing”

Find an Investor-Friendly Agent in Your Area

Real Estate Rookie 195 – Financially Free in 2.5 Years by Buying “Low Risk” Rental Properties

(00:00) Intro

(01:01) Should I Hold or Sell?

(10:13) Maximizing Rental Income

(20:43) What’s a “Good” Cash-on-Cash Return?

(23:40) Should I Get a HELOC?

(32:36) Ask Your Question!

Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-490

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