Buying rental properties wasn't Jenny Brown's dream at first. It was her husband's. In fact, Jenny got pulled into real estate investing because her husband kept handing her paperwork to complete. But once she got involved, she discovered a passion for building wealth through rental properties. Today, she and her husband own a portfolio of rental homes in solid rental neighborhoods. On this episode, Jenny shares the story of buying her first rentals, renovating them, and renting to students atte...
Jun 09, 2026•26 min•Ep. 577
Many real estate investors avoid C- and D-class neighborhoods due to crime, older housing stock, and management challenges. Mike Bonadies sees opportunity where others see problems. On this episode, Mike explains why he focuses on lower-income neighborhoods and how those properties have allowed him to build and scale a large portfolio. We look at the types of properties he's buying, what he's paying, how much rehab they're typically needing, and the numbers that make these deals work. With a low...
Jun 02, 2026•23 min•Ep. 576
Steve Whetzel has tried real estate investing three different times over the last 30 years, and the first two attempts didn’t end the way he hoped. On this episode, we look back at each chapter of his investing journey to see what went wrong, what went right, and whether it would have been possible to hold onto the properties instead of selling. Steve shares how each experience shaped the investor he is today. Steve bought his first rental properties back in 1996, long before podcasts, YouTube c...
May 26, 2026•26 min•Ep. 575
Ryan Thomson has gone all in on house hacking and believes it’s one of the fastest ways to build a rental portfolio. Ryan loves house hacking because of the favorable financing. Instead of putting 20–25% down like a traditional investment property, he was able to buy properties with as little as 5% down while also getting some of the best interest rates available. Today, Ryan generates over $30,000 a year in profit from just 5 rentals that all started as house hacks. On this episode, Ryan explai...
May 19, 2026•30 min•Ep. 574
When a rental sits vacant, landlords lose money every single day. In the past, many investors waited for the “perfect” tenant, but today, many renters who may look risky on paper could end up being great long-term tenants. The challenge for landlords is figuring out how to reduce the risk of a tenant stopping payment or damaging the property. On this bonus episode, we talk to Jamison Theander from TheGuarantors about how landlords can rent properties faster while reducing risk. Jamison explains ...
May 14, 2026•20 min
Ari Rubin has been investing in rental properties long enough to know that eventually, something is going to go wrong. Really wrong. But despite dealing with nightmare situations that would make a lot of investors quit, Ari says it’s all been worth it. On this episode, Ari shares some of the craziest situations he’s dealt with as a landlord and investor. He talks about a contractor he didn’t hire who broke into one of his properties, demolished the kitchen, and planned to move into the house him...
May 12, 2026•23 min•Ep. 573
Davethought he was making the smart move. By paying off several of his rental properties, he figured he’d lower his expenses, boost his cash flow, and simplify his portfolio. But after doing it, he started to feel like he made a mistake. Today, Dave believes he would have been better off keeping the debt and using that money to buy more properties. He shares why he thinks a larger portfolio with leverage could have outperformed a smaller, paid-off portfolio over the long run, and how losing the ...
May 05, 2026•25 min•Ep. 572
Bianca Barcelos has built her portfolio using both long-term and mid-term rentals, and on this episode, we break down what that actually looks like in the real world. Bianca walks through her experience with both strategies, comparing the pros and cons side by side. We dig into the income differences, the downtime between tenants, and the added effort required to furnish and manage mid-term properties. She shares what she typically spends to furnish a unit, the rent premium she can get, and how ...
Apr 28, 2026•23 min•Ep. 571
Greg Hall did what a lot of investors dream about, he scaled fast. In just three years, Greg built a portfolio of more than 100 rental properties, buying mostly single-family homes in a market about three hours from where he lived. His strategy was simple and effective: buy low, renovate smart, and create quality rentals in solid neighborhoods. He wasn’t slapping lipstick on properties, he was turning distressed homes into places good tenants actually wanted to live. On paper, everything worked....
Apr 21, 2026•22 min•Ep. 570
Ryan is using a simple but powerful strategy to build his rental portfolio, and it all starts with a HELOC. Instead of going through traditional financing, Ryan uses a line of credit to buy properties, using what appears to be cash. That gives him a huge advantage when making offers. After closing, he funds the renovations with the same credit line, focusing on cosmetic upgrades like flooring, fixtures, and paint to dramatically increase value. Once the property is stabilized, Ryan completes a c...
Apr 14, 2026•30 min•Ep. 569
Mike Thompson isn’t trying to build a massive rental empire. His goal is simple: a handful of solid properties that generate income for retirement and create something he can pass down to his kids. Mike started by buying a 4-unit property in Ohio, where he was living at the time. He self-managed and handled his own maintenance. He enjoyed the hands-on approach and quickly learned the business. But after relocating to South Carolina, everything changed. Turning the property over to a property man...
Apr 07, 2026•24 min•Ep. 568
On this episode, Tom McGreevy might not sound like your typical landlord. He doesn’t raise rents, doesn’t charge late fees, and even admits he might be “too nice” to his tenants. In fact, Tom says he’d give himself a failing grade as a landlord. But despite that, he’s built a portfolio that generates over $200,000 a year in rental income. Tom breaks down how his strategy actually works. His long-term rentals provide steady, reliable cash flow that covers all of his fixed expenses, giving him a s...
Mar 31, 2026•23 min•Ep. 567
On this episode, Kaycee Miller shares the real story behind building new construction rentals, including the wins and the unexpected challenges. Kaycee started out buying foreclosures and rehabbing them, but began to wonder if building from the ground up could be more profitable. She walks us through her transition into new construction, why it can sometimes be more cost-effective than buying existing properties, and how building new can lead to higher rents and better long-term returns. Kaycee ...
Mar 24, 2026•25 min•Ep. 566
Anna Mendoza started investing out of state because she believed it would produce better returns. Living in an expensive market, the $60,000 she had saved wasn’t enough to buy anything locally. But in other parts of the country, that same money could buy multiple rental properties. It seemed like a great way to build cash flow and start growing a portfolio. Instead, things quickly went off the rails. What looked like a promising investment turned into a nightmare. Anna dealt with unreliable cont...
Mar 17, 2026•26 min•Ep. 565
On this episode, Carlo Finotti explains why owning just one rental property can actually be riskier than owning several. When you only have one property, a major repair or a few months of vacancy can wipe out your cash flow for years. Carlo shares how building a portfolio of multiple rentals creates a safety net, where income from other properties can help cover unexpected expenses. Carlo also talks about the two challenges investors face when buying their second rental. The money side and the m...
Mar 10, 2026•26 min•Ep. 564
On this episode, Seamus Nally shares a powerful lesson every investor eventually faces: if it’s not working, pivot. Seamus originally set out to build a portfolio of student rentals. The plan made sense. The numbers worked. The demand was there. Then the university expanded its own housing and the student demand he was counting on dried up. Instead of digging in and hoping things would turn around, Seamus made a bold move. He pivoted and began renting rooms to residents in an addiction recovery ...
Mar 03, 2026•27 min•Ep. 563
Jacob Martinez is five years into a 10-year plan to build long-term wealth with rental properties, and he’s thinking much bigger than just next month’s cash flow. Jacob believes a decade gives neighborhoods time to improve, properties time to appreciate, and rents time to rise. While every property he buys must be cash flow-positive, he doesn’t treat rental investing as a short-term game. For him, steady growth and smart positioning matter just as much as the monthly numbers. On this episode, Ja...
Feb 24, 2026•26 min•Ep. 562
Thomas lives in a high-cost area where buying rentals locally simply didn’t make sense for cash flow, especially as a newer investor with limited capital. Instead of forcing a bad deal in his backyard, Thomas made the decision to invest out of state. On this episode, he walks us through how he chose the markets he invested in and whether he physically visited the areas before buying. Thomas didn’t just pick one market and hope for the best. Diversification was important to him, so he invested in...
Feb 17, 2026•23 min•Ep. 561
Mary spent years on the road as a travel nurse, living in mid term rentals across the country. After seeing firsthand how well these properties served traveling professionals, she decided to become an investor herself. We break down exactly what Mary looks for when buying a mid term rental, including location, and the best bedroom count to look for. She shares how much she typically spends to furnish a property, how long her tenants usually stay for, and how much of a rent premium she gets vs if...
Feb 10, 2026•24 min•Ep. 560
On this episode, I’m joined by Jeremy Smith, an investor who proves you don’t need hundreds or thousands of rental properties to be successful. Jeremy owns just a few rentals, but they generate enough monthly cash flow to cover all of his living expenses. Jeremy still works a full-time job, but his rentals give him a powerful safety net. If his income dips in a slow month or an unexpected expense pops up, the extra cash flow from his properties helps absorb the hit and keeps stress low. We talk ...
Feb 03, 2026•25 min•Ep. 559
This bonus episode features Caeli Ridge from Ridge Lending Group, breaking down what’s happening right now with DSCR loans and why they’re getting so much attention from rental property investors. Caeli explains how DSCR loan rates have been coming down and are now very close to Fannie Mae and Freddie Mac rates. We talk about why DSCR loans are often simpler than conventional mortgages, how they qualify based on the deal instead of the investor’s personal income, and why that makes them especial...
Jan 29, 2026•26 min
Joel has been investing in rental properties for 48 years and has figured out how to increase rental income without buying more properties. On this episode, Joel shares practical strategies he uses to get more cash flow from the rentals he already owns. We talk about how he keeps up with rent increases to make sure his properties stay profitable, along with inexpensive upgrades that help units look better and command higher rent. Joel explains his approach to flooring, including LVP vs. carpet, ...
Jan 27, 2026•24 min•Ep. 558
Tim Delaney has built a diversified real estate portfolio that includes long-term rentals, a short-term rental, and a strip mall. What makes his story especially interesting is that his very first deal was the strip mall, and he bought it with zero money out of pocket. On this episode, Tim breaks down how that deal came together and how a simple conversation with his banker introduced him to the BRRRR strategy. Tim knew he wanted to rehab properties, but he also knew his limits. He wasn’t a cont...
Jan 20, 2026•26 min•Ep. 557
Ron took an unconventional path to financial freedom. He was living a comfortable life in California when he realized his money would go a whole lot farther if he bought rentals somewhere else. So he packed up, moved across the country to Connecticut, and got to work building a rental portfolio from the ground up. Over the next several years, he bought properties, self-managed tenants, handled maintenance, and slowly created the income stream he needed .But after plenty of tenant phone calls, tu...
Jan 13, 2026•25 min•Ep. 556
Terry Kerr didn’t get it right when he first started buying rental properties. In fact, he made just about every mistake you can make. He bought in the wrong areas, took on rehabs himself to “save money,” hired the wrong people, and bought properties that were either too big or too small to work as profitable rentals. Over time, Terry figured out what actually matters. He found the sweet spot for the ideal rental property and built a system around it. On this episode, Terry breaks down what he l...
Jan 06, 2026•21 min•Ep. 555
Greg Thompson’s story is proof that your past financial mistakes do not get the final say. In his 20s, Greg admits he had no idea how to manage money. A string of bad financial decisions eventually left him homeless. Fast forward to today, and Greg owns a portfolio of 37 rental units and has built more than $1 million in equity. On this episode, Greg walks us through how he completely turned his life around and, more importantly, how he came up with the money to start buying rentals when he had ...
Dec 30, 2025•22 min•Ep. 554
Alana Kern is proof that you can build a rental portfolio while working a busy full-time job She has steadily grown her rentals by being intentional with her time and systems. On this episode, we break down how many hours Alana actually spends managing her rentals, the platform she uses to advertise vacancies, and the processes that help her stay organized. Alana also shares a tough lesson from a tenant she didn’t thoroughly screen, what went wrong, and what she does differently now. We also tal...
Dec 23, 2025•24 min•Ep. 553
Matt McCurdy had a solid 9–5 job on paper, but the corporate life wasn’t for him. Long days indoors and a lack of control over his time pushed him to ask a simple question: there had to be a better way. Matt set out with a clear plan to replace his W-2 income with rental income, and he made it happen. On this episode, Matt breaks down exactly how he did it. He shares how many doors it took to replace his paycheck, how he financed his properties, and how he continued buying rentals after walking ...
Dec 16, 2025•26 min•Ep. 552
Zach started buying rentals at 21 with no family money, no partners, and no roadmap. He didn’t come from a real estate background, but he taught himself creative financing and pushed forward deal by deal. In just two years, he built a large rental portfolio that now includes more than 100 properties. On this episode, Zach walks us through exactly how he did it. He shares how he built a trustworthy team to handle construction and property management, and why setting clear goals played a huge role...
Dec 09, 2025•27 min•Ep. 551
On this episode, we walk step by step through how Derek Harris built his rental portfolio from the ground up. Derek has been buying rental properties for five years, and today he owns 10 doors. He takes us through each acquisition, explaining how he found the properties, their condition, and the work he did to fix them up. Derek also breaks down how he financed every deal. He talks about where he found the money for his down payments, how he structured his loans, and why he started using DSCR lo...
Dec 02, 2025•24 min•Ep. 550
