Real Estate Rookie

Real estate bookkeeping might not be the most thrilling part of owning a rental property, but it’s often the difference between bleeding money each month and earning cash flow you can count on. Today’s guest will show you exactly how to get your books in check so you can make your properties even more profitable!

Welcome back to the Real Estate Rookie podcast! Grace Wills is a CPA, a homeschooling mom, and a self-described “risk-averse” investor. So, when her husband suggested they buy an investment property back in 2018, she was skeptical. However, it didn’t take long for that first property to start generating plenty of cash flow, at which point Grace saw that real estate investing was far less “risky” than many other investments.

Fast forward to today, and Grace owns a real estate portfolio that’s creating long-term wealth for her family, despite losing money on three different house flips. In this episode, she shares the importance of having a mentor to help you navigate the ebbs and flows of real estate, why bookkeeping is one of the most underrated skills, and some of her favorite tools and software for new investors!

In This Episode We Cover

Why Grace never gave up on real estate (even after three “failed” house flips)

The four people every real estate investor needs in their corner

The two-part software “stack” every new investor should have

The biggest challenges when going into real estate investing with family

What to know before putting your rental property in an S corporation

Why you should always speak to multiple lenders before getting financing

And So Much More!

Check out more resources from this show on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠BiggerPockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠h⁠t⁠⁠tps://www.biggerpockets.com/blog/rookie-731⁠⁠⁠.

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Thinking about self-managing your rental property? Then, you’ll need property management software to help with things like processing applications, collecting rent, and managing maintenance requests. In this episode, we’re sharing our favorite tools so you can pick the right one for your portfolio!

 

Welcome back to another Rookie Reply! There are dozens of property management tools floating around, but which ones are best for new landlords? Ashley breaks down the different categories of landlord software and shares four steps to finding the right option for you. Next, are regulations slowly killing the short-term rental industry? The short answer is no. However, there are two things every investor should do before committing to a short-term rental market, and Tony’s going to tell you what they are!

 

Finally, we’ll get into wholesaling, a strategy that could help kickstart your real estate investing journey without having thousands of dollars to deploy. We’ll show you how the entire wholesaling process works and three easy ways to find deals today!

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

In This Episode We Cover

The best property management tools for beginner landlords

Four steps to finding the right property management software for you

What heightened regulations mean for the future of short-term rentals

Whether short-term rentals are still a viable investing strategy in 2026

Three ways to start wholesaling today (with low money!)

And So Much More!

Check out more resources from this show on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠BiggerPockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠h⁠t⁠⁠tps://www.biggerpockets.com/blog/rookie-730⁠⁠.

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Many rookies think things become easy once you’ve built a large real estate portfolio, but that’s far from true. Even with 26 short-term rentals, a 13-unit hotel, and a few house flips under his belt, Tony deals with many of the typical rookie challenges. In today’s episode, he’s sharing the lessons he’s learned and the rental pivots he’s making so YOU can grow and scale like him!

Welcome back to the Real Estate Rookie podcast! Last time we checked in with Tony about his real estate business, he was in the process of stabilizing his new hotel. Now, with an entire calendar year in the books, we’ll revisit the property and how it’s performing today. We’ll also hear about Tony’s next hotel investment and how he’s approaching it differently now that he has proof of concept.

Tony also outlines the best course of action for new investors who want to break into the short-term rental space in 2026. Finally, what does a day in the life of a full-time real estate investor look like? Tony gives you an inside look at the flexibility he enjoys by owning rental properties that you don’t get with a nine-to-five job!

In This Episode We Cover

Rental pivots Tony’s making in 2026 for even bigger returns

Updates on Tony’s rental portfolio and his 13-unit hotel investment

The biggest pain points when investing in a smaller real estate market

What Tony’s average week looks like as a full-time real estate rental investor

First steps for rookies looking to invest in short-term rentals in 2026

How to build a real estate business that gives you more freedom and flexibility

And So Much More!

Check out more resources from this show on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠BiggerPockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠h⁠t⁠⁠tps://www.biggerpockets.com/blog/rookie-729⁠.

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The real estate investing moves you make today could change your life. Those in their 40s, 50s, and 60s often look back and regret not starting sooner. Today’s guest isn’t letting that happen, and in this episode, she’ll show YOU how to take advantage when that next rental property comes your way!

Welcome back to the Real Estate Rookie podcast! When Megan Chou’s father challenged her to read the personal finance classic, Rich Dad Poor Dad, little did she know it would completely alter her life’s trajectory. The book’s lessons on building wealth inspired her to stash her money away in a brokerage account and, at just 20 years old, buy her very own rental property—a townhome she house hacked with her best friend.

Then, only two years later, right as she was graduating from college, she took down a fourplex—renovating each unit while living in it, one by one. Stay tuned as Megan shares how she leveraged her home equity to buy it, what went wrong after buying the property, and how she stayed resilient when her property started fighting back!

In This Episode We Cover

How Megan bought her first two rental properties (while still in college!)

How to fund your next investment property using your existing home equity

What Zillow, Redfin, and the MLS can’t tell you about properties or neighborhoods

Bouncing back from ice, raccoons, and plumbing failure on the same property

Two crucial things to do when experiencing a setback with your property

And So Much More!

Check out more resources from this show on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠BiggerPockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠h⁠t⁠⁠tps://www.biggerpockets.com/blog/rookie-728.

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Do you have home equity sitting in your primary residence? You could use it to buy your first or next rental property! There are several ways to do this, and in today’s episode, we’re sharing them so you can make your money work harder!

 

Welcome back to another Rookie Reply! Whether it’s a home equity line of credit (HELOC) or a cash-out refinance, there are multiple ways to access the equity in your home. But which option is best? Stay tuned and we’ll help you determine the right move for your situation.

 

Next, if you’re preparing to open an Airbnb, the days leading up to launch can be nerve-wracking. Thankfully, our resident short-term rental expert, Tony, has some game-changing tips that will help you create the best possible guest experience and bring in plenty of five-star reviews!

 

Finally, what do you do if your investment property hasn’t appreciated at all over the last one, two, or even five years? Should you hold or cut it loose? The answer is more nuanced than you might think, but we’ll help you reach the right decision for your real estate investing goals!

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

In This Episode We Cover

How to use your primary residence to buy your first rental property

Three ways to access your home equity (and fund your next property)

How to create a five-star Airbnb experience (and get more reviews!)

What every rookie should know before launching a short-term rental

When to sell a rental property that has low or negative cash flow

Whether a rental property with low (or no) appreciation is a bad investment

And So Much More!

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