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 solid financial foundation. Then his Airbnb properties, which are more unpredictable, become the upside and drive his profit. He also shares why having those short-term rentals located three hours away has turned out to be an advantage rather than a drawback.

We also talk about the role his W2 job plays in his investing strategy, and how it’s allowed him to take bigger risks without relying on rental income to live.

Tom shares how he’s sold properties along the way and how working with a knowledgeable CPA helped him legally avoid a massive tax hit. 

https://rentalincomepodcast.com/episode567

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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 breaks down her experience developing an 8-unit property in the downtown area of her small town, including how she found the lot.

We also dive into a unique deal where she purchased an old church that had been converted into a single-family home, but was zoned for multifamily use. That opportunity came with its own hurdles, including navigating historic district regulations and working through the approval process with the historic commission.

But not everything went according to plan. Kaycee shares the reality of lease-up, including the mistake of expecting full occupancy right away and the challenges she faced in targeting the high end of the rental market. She talks about what she learned when demand didn’t match her expectations, how she adjusted her strategy, and what she would do differently next time.

https://rentalincomepodcast.com/episode566

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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 contractors, break-ins, unexpected repairs, and tenants that required far more time and money than she anticipated. The expenses piled up and the cash flow she expected never materialized.

On this episode, Anna walks through exactly what she bought, why the properties didn’t perform the way she expected, and the hard lessons she learned from trying to manage rentals from a distance.

But the story has a happy ending. Anna eventually sold those properties and used the money to pivot into a completely different strategy.

Instead of chasing cash flow in distant markets, she began buying properties closer to home and focusing on appreciation. That shift changed everything.

Today Anna has built a portfolio that has made her millions in real estate. We also talk about how she’s able to come up with the down payments for more expensive properties and the strategy she’s using to continue growing her portfolio today.

https://rentalincomepodcast.com/episode565

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 mental side.

He explains how he overcame both and how adding more properties allowed him to benefit from economies of scale and reduce risk across his portfolio.

We also talk about how many doors Carlo had before he finally felt comfortable with repair risk, how his perspective has changed as his portfolio has grown, and the worst thing that has happened to him as a rental property investor.

https://rentalincomepodcast.com/episode564

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 program. When new challenges surfaced with that strategy, he adjusted again, eventually transitioning the property into a traditional long term rental. By then, market rents had risen and the deal that once struggled was suddenly producing strong, stable cash flow.

We also talk about what it’s like investing alongside family, as Seamus partners with his brothers on their properties.

Plus, we get into one of the most overlooked investing advantages: building strong relationships with neighbors. Seamus explains how being proactive and communicative has not only protected their properties, but has also led to off-market deals and neighbors acting as extra eyes and ears. 

https://rentalincomepodcast.com/episode563