Real Estate Rookie
BiggerPockets
0
Real Estate Rookie is a podcast for beginners in real estate investing. Hosts Ashley Kehr and Tony J Robinson break down real-world deals, offer one-on-one coaching, and build a supportive community. They answer common newbie questions and provide tips, tools, and roadmaps for building a modest portfolio. The show releases episodes every Monday, Wednesday, and Friday.
Επεισόδια
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Making $3,000/Month Cash Flow (Per Property) with This Scalable Rental Strategy 22.07.2026 42λOne of the biggest mistakes new investors make is analyzing rental properties for the best-case scenario. Today’s guest does the opposite. He plans for the worst, and it’s the reason his deals consistently outperform others. In this episode, he’s sharing his secret for getting maximum cash flow with the least work possible! Welcome back to the Real Estate Rookie podcast! Luke Frizzell went from owning a primary residence that was draining his bank account, to converting his garage into an ADU and getting a 25% cash-on-cash return. But then, he did an “about face” and pivoted into residential assisted living, where he generates $3,000 in monthly cash flow, per property, without ever dealing with operations! Tune in to learn how Luke uses the military “SMEAC” framework to turn every deal into a planned mission, why the best next investment might be the property you already own, and how the lease-to-operator model makes assisted living one of the most “hands-free” cash flow strategies available today. If you've been chasing unit count and wondering why the effort never matches the returns, Luke's story is your permission to think differently. In This Episode We Cover How to make more cash flow with the residential assisted living strategy How to create extra income streams on the property you already own How Luke generated a 25% cash-on-cash return with his first ADU The SMEAC framework—what it is and how to apply it to real estate How to make your investment more “hands-free” with the lease-to-operator model Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-747. Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com. Learn more about your ad choices. Visit megaphone.fm/adchoices
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She Bought the Property No One Wanted. It Had a Hidden Income Stream ($3K+/Month). 21.07.2026 32λPeople think you need a dozen rental properties to achieve financial freedom. You don’t. Buy the right property in the right location, and it may only take one. Just ask Hana and Easton Jones, whose tiny back unit pays their entire mortgage and then some—allowing Hana to quit her W-2 job and live out her dream of being a stay-at-home mom! Welcome back to the Real Estate Rookie podcast! Hana and Easton were a couple of 25-year-olds with regular jobs. How could they possibly afford real estate around Los Angeles? Driven by the dream of homeownership, they sacrificed, they saved, and when the time came, they bought the house no one wanted. It wasn’t perfect. It needed work. But it also had its own hidden income stream—a small ADU (accessory dwelling unit) that now covers their $3,300 mortgage each month! In this episode, they break down their exact savings strategy, what it looks like to house hack an Airbnb, and how Hana was able to buy back time with her kids. Whether you live in an expensive city or want a way out from your nine-to-five, this story delivers the inspiration you need to take the next step in your real estate journey! In This Episode We Cover: The ADU (accessory dwelling unit) that makes $3,000-$5,000+ per month How to save aggressively for a down payment (even on a normal salary) Why Hana and Easton chose to put more money down on their house hack The “overlooked” property that allowed Hana to step away from her W-2 job How this frugal couple got creative on a $30,000 renovation budget And So Much More! Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-746. Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com. Learn more about your ad choices. Visit megaphone.fm/adchoices
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The Housing Market Is Shifting. Here’s What Rookies Should Do. (Rookie Reply) 17.07.2026 15λThe housing market looks very different than it did just a year or two ago. Home prices are softening, rates have eased slightly from the highs of 2023 and 2024, and sellers are more willing to negotiate than they've been in years. But rookie investors still want to know: Is 2026 actually the right time to buy? Welcome back to another Rookie Reply! Today we’re answering three pressing questions from the BiggerPockets Forums. You just got your first rental property under contract–what’s the next step? Is out-of-state investing the answer to areas that don’t cash flow, and if so, how do you manage a property from afar? But perhaps most importantly, does it even make sense to invest in real estate in 2026? Ashley and Tony break down the 2026 market, the contract-to-closing checklist every rookie investor needs, and the exact steps Tony took to build an investing team over 1,000 miles away! Looking to invest? Need answers? Ask your question here! In This Episode We Cover Whether it still makes sense invest in real estate in 2026 The one data point that tells you whether a real estate deal is worth it The full contract-to-closing checklist you need to get your keys on time What to do when you can’t find cash flow in your own market How to build your team (from scratch) when investing out-of-state And So Much More! Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-745. Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com. Learn more about your ad choices. Visit megaphone.fm/adchoices
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Long-Term Rentals vs. Short-Term Rentals: Which Is Best for Beginners? 15.07.2026 39λWhen buying your first rental property, everyone gives you the same advice: play it safe, get a long-term tenant, and collect the rent. But that same house, run as an Airbnb, can often make two or three times the cash flow. So which investing strategy should you actually use for your first deal? Welcome back to the Real Estate Rookie podcast! Today, we’re settling this debate once and for all: short-term rentals or long-term rentals? We both grabbed a real, middle-of-the-road property from our own portfolios, put them head to head, and broke down the three things that actually matter for rookie investors: the money, the workload, and the risk. Ashley’s long-term rental might have the edge when it comes to ease of management, but Tony's short-term rental tax loophole gives certain investors a way to (legally) slash their tax bills by thousands. There is no one-size-fits-all answer here. But by the end of this episode, you'll know exactly which strategy fits your investing goals! In This Episode We Cover Real properties with real numbers from Tony and Ashley's portfolios Why measuring your cash-on-cash return is crucial when comparing these strategies How much time it actually takes to manage a long-term or short-term rental The biggest risks to consider before committing to either strategy How to potentially slash your tax bill by thousands with the short-term rental loophole And So Much More! Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-744. Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com. Learn more about your ad choices. Visit megaphone.fm/adchoices
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She Built a 3-Property Portfolio in 5 Years While Working Her 9-5 13.07.2026 37λYour first rental property rarely comes from sitting back and waiting. It usually comes when you put yourself out there, talk to others about what you're building, and stay in the game long enough for the right moment to show up. That’s exactly what today’s guest did, and it led to a wild deal that kickstarted her real estate portfolio! Welcome back to the Real Estate Rookie podcast! Stephanie Wagner spent nearly 20 years in a full-time job, putting her real estate dreams on hold through a marriage that wasn't working. Then, she used her divorce as the starting line. Six months later, she closed on her first real estate deal, a duplex she was able to house hack. Today, she owns five rental units and even has her real estate licence! Stephanie shares about the everyday moment that led to buying an off-market deal, the second deal that involved a tricky tenant situation, and the mindset shift that separates the investors who start from the ones who never do. If you've been holding out for the “perfect” moment to invest in real estate, Stephanie's story is proof that you just need to take action! In This Episode We Cover How Stephanie bought three rental properties while working nine-to-five The pivotal moment that led to Stephanie’s first property (an off-market duplex!) The benefits of using a real estate agent on an off-market deal Why the quality of your rentals matters more than your number of doors Raising rent on long-term tenants with fixed incomes And So Much More! Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-743. Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com. Learn more about your ad choices. Visit megaphone.fm/adchoices
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How to Find and Fund Your First Real Estate Deal (From Scratch) (Rookie Reply) 10.07.2026 20λYou've got very little savings, almost no credit history, and you want to buy a rental property. Most people would tell you to wait, but today, we’re giving you clear, actionable steps you can take toward getting that first property under contract! Welcome back to another Rookie Reply! Today, we’re answering three questions that cover the anatomy of a first deal: where the money comes from, where the deal comes from, and what it will really cost you. First, suppose you have no money or credit. Can you still invest in real estate? Another investor wants to know if wholesalers are worth using, and finally, we’ll hear from an actual wholesaler who’s looking for the best ways to estimate rehab costs so he can deliver deals investors actually want to buy! Tony explains why finding great real estate deals is the number one tool every rookie needs in their toolbelt, and Ashley shares a wholesale real estate strategy that nobody in the industry is using yet!! Looking to invest? Need answers? Ask your question here! In This Episode We Cover How to invest in real estate when you have low money and no credit How to save for your first down payment (fast!) The best investing strategy for buying rentals with low money down The wholesaling strategy explained (and how to buy a wholesale deal) How to estimate rehab costs as a complete beginner And So Much More! Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-742. Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com. Learn more about your ad choices. Visit megaphone.fm/adchoices
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The Exact Investment “Stack” We’re Using to Retire Early (Not Just Rentals) 08.07.2026 30λDon’t want to wait until 65 to retire? With a combination of rental properties and some of the other investments we’re covering on today’s show, you may not have to. Whether you’re starting from zero or diligently building your nest egg, use these eight steps to build a diversified portfolio and reach financial freedom much faster! Welcome back to the Real Estate Rookie podcast! Today Ashley and Tony are pulling back the curtain on their actual retirement plans—what they're doing, why they're doing it, and what they wish they'd known sooner. They share how they first got into real estate investing and how they’ve adjusted their portfolios over time. They also break down the investment “order of operations,” a sequence of financial moves that will help you build long-term wealth! Along the way, we’ll get into things like the 401(k) employer match, the triple-tax-advantaged HSA account, and the often-misunderstood 529 college savings plan. Whether you want to gradually step away from your W-2 job or simply have “enough” when you reach traditional retirement age, this episode gives you a clear roadmap for achieving your long-term financial goals! Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-741. Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com. Learn more about your ad choices. Visit megaphone.fm/adchoices
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She Bought Her First Rental Property with $0 Down (Her Exact Playbook) 06.07.2026 38λWhat if the one thing stopping you from buying your first rental property isn’t money, or connections, but the belief that it’s just not possible for someone like you? Today’s guest is proof that with the right game plan, real estate investing offers a path that can set anyone free, including YOU, from the nine-to-five grind! Welcome back to the Real Estate Rookie podcast! Crystal Lloyd didn't have connections, a trust fund, or a head start. What she had was a two-hour daily commute and a willingness to do what most people won't. She volunteered at BPCON to get in, and walked out with the relationships that led to her first deal! And in this episode, she breaks down exactly how she bought it, including the grant “stack” that helped her pay zero out of pocket and the “layered” house hacking strategy most rookies don’t want to try. But that’s not all. Crystal also shares lessons from a bad contractor experience, and the tenant screening process every rookie needs. If you've ever felt like real estate was out of reach, Crystal's about to show you that anyone can start today! In This Episode We Cover The exact moment that sparked Crystal’s real estate investing journey The grant “stack” Crystal used to buy her first deal with $0 out of pocket How Crystal pays just $50 a month to live in the house she owns The tenant pre-screening questionnaire every new investor needs Lessons learned from a bad contractor experience (that you can avoid!) And So Much More! Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-740. Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com. Learn more about your ad choices. Visit megaphone.fm/adchoices
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How to 2X Your Cash Flow (or More) on the Property You Already Own (Rookie Reply) 03.07.2026 25λWhat if you could take the rental property you already own and make 2-3 times more? Whether you’re in the red, barely breaking even, or wanting more from your rentals, we’re showing you multiple ways to boost your cash flow! Welcome back to another Rookie Reply! Today, we’re answering three questions from the BiggerPockets Forums that cover some of the most searched and most overlooked strategies in real estate investing right now. Is co-living actually realistic, and how do you pivot to the model without losing your mind? Don’t think you have enough for a down payment? The good news is that there are several loans and strategies that require much less than you think. Stick around until the end because we’ve got a couple of strategies most rookies never consider that could make you $10,000 from just one house! Whether you're trying to squeeze more cash flow from a property you already own, get into your first deal with limited savings, or find an investing strategy that most beginners overlook, this episode has something for every stage of the journey! Looking to invest? Need answers? Ask your question here! In This Episode We Cover Four ways to double your rental income (or more) on the property you already own How to pivot from a single-tenant property to a room-by-the-room model How to buy your first rental property without a big bank account The loan that could help you get into real estate with as little as $0 down How the co-living strategy works and why demand is growing Why assisted living and sober living are some of the most overlooked, win-win strategies And So Much More! Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-739. Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com. Learn more about your ad choices. Visit megaphone.fm/adchoices
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3 Ways to Fund Your First Real Estate Deal Without 20% Down 01.07.2026 37λWhat’s stopping you from buying your very first rental property? For most rookies, it’s rarely ever the market, the interest rates, or even the competition–it's a number in their head. Today, we’re breaking down that barrier with real rookie use cases that will inspire you to take that next step in your real estate investing journey! Welcome back to the Real Estate Rookie podcast! In this episode, we’re sharing three ways to fund real estate deals that have actually worked for past Rookie guests. None of these creative financing options require 20% down, none of them require a traditional bank, and one of them doesn't involve a lender at all! We dive into how hard money loans work and when they make sense, how to find a seller who'll say yes to seller financing, and the levers you can pull to structure your deal. Ashley also shares her hard money horror story so you don't have to learn those lessons the expensive way! If you've been sitting on the sidelines because you don't think you have enough money to invest, this conversation will give you the knowledge and confidence to get started today! In This Episode We Cover Hard money—what it is, how lenders make money, and when it actually makes sense for a rookie Ashley's hard money horror story and the exact questions you need to ask How to structure a seller financing deal as a complete beginner Real seller financing case studies (from past Rookie guests!) The right (and wrong) reasons to bring in an equity partner on your real estate deal And So Much More! Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-738. Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com. Learn more about your ad choices. Visit megaphone.fm/adchoices
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He Started Investing in His 40s, Now He’s on Track to Retire with Rentals 29.06.2026 30λNot everyone gets into real estate investing when conditions are perfect. Some, like our next guest, get in because they have no other choice. The path Brent Beard was on just wasn’t cutting it anymore–especially when people were depending on him. If your back’s against the wall and you want to build a better life for your family, rental properties could be the answer! Welcome back to the Real Estate Rookie podcast! Brent is a real estate agent in training and investor in the Kansas City area who bought his first duplex in 2025. He did it while working a full-time W-2 job, serving in the National Guard, studying for his real estate licence, and raising his granddaughter. Owning rental properties wasn’t always on Brent’s radar, but last July, he picked up a book that changed his whole philosophy. Despite starting in his 40s, Brent has closed on his first deal and is aiming to retire in 10 years! Brent isn't here with a polished success story, but a real one. He dives into the property tax mistake nobody warned him about that nearly doubled his bill overnight, the buy box he had to abandon to find a deal that actually cash flowed, and the one thing he wishes someone had told him before he closed! If you have a full schedule, real responsibilities, and every reason to keep putting real estate on the back burner, Brent's story is proof that the biggest mistake is simply not starting! In This Episode We Cover What finally pushed Brent to take action on his first real estate deal Juggling a W-2 job, military service, and real estate without dropping the ball The rookie-friendly tools and processes Brent used to analyze his first duplex The property tax mistake that nearly doubled Brent’s bill (and what to check before you close!) The huge investing advantages you get by becoming a real estate agent And So Much More! Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-737. Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com. Learn more about your ad choices. Visit megaphone.fm/adchoices
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My Property Is Losing Money: Should I Sell or Pivot? (Rookie Reply) 26.06.2026 18λThe property you spent months working on is about to lose you money. What should you do? Sell? Pivot? Invest for long enough and you’re bound to run into this scenario at some point. But not to worry—today, we’re showing you exactly what to do when things go south! Welcome to another Rookie Reply! We’re back with three more questions from the BiggerPockets Forums. One investor is about to lose money flipping a house and needs a way out or a reason to stay in. Another is about to form a real estate investing partnership but is missing one critical element that could change the entire deal. And if you’re in the exciting final stages of closing on a rental property, or you're already sitting with the keys, wondering what on earth to do now that you're a landlord, we’ve got the answers! Ashley and Tony have been in all three of these situations, and Tony’s in one of them right now! Looking to invest? Need answers? Ask your question here! In This Episode We Cover When to sell a struggling flip (at a loss) or convert it to a rental property The one thing almost nobody considers before creating a real estate partnership Why a 50/50 equity partnership is actually fairer than it feels when one partner brings all the money The biggest differences between a joint venture and an LLC (limited liability company) Why forming an LLC on your first partnership deal might be a mistake What to tackle in your first 30 days after closing (and what can wait!) And So Much More! Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-736. Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com. Learn more about your ad choices. Visit megaphone.fm/adchoices
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Making $29,000/Month from One “Boring” Property (1,000 Miles Away) 24.06.2026 46λWhat if the best real estate investment isn’t the one with tenants, toilets, or employees, but the low-maintenance property everyone else is ignoring? Today’s guest is making thousands each month from one of these properties, and there are many more just like it. She’ll show you exactly how to find them! Welcome back to the Real Estate Rookie podcast! Today we're sitting down with Bree Hartman, who went from one “accidental” rental property to building a $6 million self-storage portfolio–all while pregnant, working her W-2 job as a personal trainer, and cold calling self-storage owners on her lunch breaks. She did all of this as a complete newbie to commercial real estate from the other side of the country! Bree breaks down how she finds off-market self-storage facilities using a single tool, the exact cold calling script she uses to get baby boomer owners talking, and how she structured her very first seller financing deal. She even shares the five-point blueprint that shows YOU exactly where to invest. If you've been sleeping on self-storage, our conversation with Bree will wake you up to one of the most underrated assets right now! Looking to invest? Need answers? Ask your question here! In This Episode We Cover How Bree finds off-market self-storage deals hiding in plain sight The exact cold calling script that gets bored retirees to sell (and a live example!) Buying a $3.1 million facility with zero commercial experience The seller financing trick that got an owner to say yes–it's not what you'd expect The five-point blueprint for finding markets where you'll never compete with the big players And So Much More! Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-735. Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com. Learn more about your ad choices. Visit megaphone.fm/adchoices
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How to House Hack Your Way Out of $200K in Student Loan Debt! 22.06.2026 38λAt 31, James sat down at a kitchen table with his wife Aida, ran the numbers on the next 30 years, and didn't like what he saw—$200,000 in student loans and a retirement plan neither of them believed in. So they stopped waiting for a change, and built something instead. Welcome back to the Real Estate Rookie podcast! Our guest, James Doren, and wife, Aida, didn't have a trust fund or an obvious path forward. They had a spreadsheet, a private money lender, and an empty space above their garage. This accessory dwelling unit (ADU) solution added 50% value on their equity, wiped out their student loans, and set them on a path that most investors never consider: intentionally shrinking their portfolio from 10 doors to 4. But the deal that surprised them most didn't come from an agent or Zillow. It came from a tenant who knocked on their door with a problem the bank couldn't solve! James breaks down the house hack that started it all, how he convinced a private money lender to fund the build, and the rent-to-own agreement he structured for his tenant that gave both sides exactly what they needed. If you've ever sat at your own kitchen table and wondered if there's a better way…James's story is your proof that there is! In This Episode We Cover How James and Aida used weekly money dates to align on their financial goals and take their first step into real estate The ADU build that created $160K in equity How to approach a private money lender and handle the tough questions Why James intentionally sold 6 properties and why owning fewer doors actually made him more money! The rent-to-own agreement a tenant brought to them: how it works, what an option fee is, and why it removed all their risk And So Much More! Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-734. Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com. Learn more about your ad choices. Visit megaphone.fm/adchoices
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The Real Estate LLC Mistake That Could Cost You Thousands (Rookie Reply) 19.06.2026 26λDo you need a real estate LLC, and should you form one before or after buying a rental property? This is a very common rookie question, and liability protection is one of the most misunderstood topics in real estate investing. But not to worry—today we’re setting the record straight and showing you how to build bulletproof protection for you and your assets! Welcome back to another Rookie Reply! Does a rental property have to make positive cash flow for it to be considered a “good” deal? If you’re using the house hacking strategy, maybe not! In today’s episode, we’ll share exactly why this is often the exception to the rule. Finally, what’s the best way to fund rental renovations? In most cases, lenders will help you finance the purchase of a rental property, but you’ll have to scrounge up the money for your renovations—except if you use an FHA 203(k) loan. How do these loans work, and what are the pros and cons? Stick around to find out! Looking to invest? Need answers? Ask your question here! In This Episode We Cover Whether a rental property needs to cash flow if you’re house hacking LLCs, umbrella policies, and other types of liability protection explained Whether you need to form an LLC before buying a rental property What to know before transferring ownership from your personal name to an LLC How to fund your purchase and renovations with a 203(k) loan And So Much More! Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-733. Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com. Learn more about your ad choices. Visit megaphone.fm/adchoices
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The Easiest Ways to Find Off-Market Properties in 2026 (Our Exact Playbook) 17.06.2026 32λMany rookies assume the best real estate deals are already listed on the market, but what if that’s not the case? The truth is, it’s getting harder and harder to find rental properties on the MLS that actually pencil out. Thankfully, there are dozens of ways to find profitable off-market properties that can make you more money, and today, we’re sharing our exact playbook! Welcome back to the Real Estate Rookie podcast! The term “off market” is thrown around as an easier way to buy real estate, but most rookies don’t actually know where to start. In this episode, we’re breaking down how we found, funded, and closed our very first off-market deals—as complete beginners. You’ll hear about Ashley’s 12-unit acquisition that doubled in value and Tony’s very first wholesale real estate deal that made him $30,000! But that’s not all. Beyond driving for dollars and direct mail, we’re sharing our favorite strategies to use in 2026. With all kinds of tips for sourcing deals, structuring offers, and negotiating with sellers, there’s no reason why you can’t go out and buy your first off-market property this year! In This Episode We Cover How Ashley bought six duplexes (12 units), off-market, from ONE seller How Tony pocketed $30,000 on his very first wholesale deal The one major advantage rookies have when buying off-market properties How to use the driving for dollars strategy to uncover “hidden” real estate deals Why you should always make multiple offers on an investment property The main difference between assumable mortgages and subject-to deals And So Much More! Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-732. Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com. Learn more about your ad choices. Visit megaphone.fm/adchoices
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She Lost $85,000, Then Made It All Back with a Single Rental Property 15.06.2026 39λReal 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. Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com. Learn more about your ad choices. Visit megaphone.fm/adchoices
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The Best Property Management Software for Small Landlords (Rookie Reply) 12.06.2026 22λThinking 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. Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com. Learn more about your ad choices. Visit megaphone.fm/adchoices
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Big Changes I’m Making to My Portfolio This Year (That Will Make Me Richer) 10.06.2026 40λMany 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. Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com. Learn more about your ad choices. Visit megaphone.fm/adchoices
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She Started Investing in College and Already Has 5 Rental Units (And Counting) 08.06.2026 43λThe 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. Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com. Learn more about your ad choices. Visit megaphone.fm/adchoices
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