I Built a Rental Portfolio That Gives Me “Boring,” Steady Cash Flow

10/11/2025 34 min
I Built a Rental Portfolio That Gives Me “Boring,” Steady Cash Flow

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Episode Synopsis

Don’t think you have enough time, money, or energy to invest in real estate? Living in an expensive and highly competitive market, today’s guest had every reason not to invest, yet has been able to build her own rental portfolio in just a few years—all while working a normal W-2 job. If she can do it, YOU can, too!



Welcome back to the Real Estate Rookie podcast! Esther Simeone was stuck in a pricey market, and after submitting over a dozen offers and missing out on every one, she could have put real estate investing on the back burner and waited for the market to turn. But hell-bent on house hacking and building wealth with real estate, Esther kept looking. Finally, the perfect deal fell in her lap—an “overlooked” listing that now helps pay her mortgage!



Since then, she has snagged a second property, used the Airbnb arbitrage strategy for more cash flow, and even designed an ADA-accessible vacation rental—a passion project that has given her a fresh perspective on what can be achieved through real estate. In this episode, Esther will show you how to get in the game today, no matter how little time or money you’re working with!



In This Episode We Cover

How to build and scale a real estate portfolio while working a W-2 job

Using other people’s rentals to make money with rental arbitrage

How to make “boring,” steady cash flow with medium-term rentals

Covering your mortgage (or part of it) with the house hacking strategy

Finding discounted investment properties by scouring old listings

And So Much More!





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