Most rookies buy rental properties for monthly cash flow or long-term appreciation, but for today’s guest, the enormous tax benefits were the biggest driver. Whether you’re looking to achieve true financial freedom, leave your W-2 job, or keep more of your hard-earned money from the tax man, this episode is for you!

Welcome back to the Real Estate Rookie podcast! Ross Alcorn was very good at his medical sales job, but he was slowly burning out. His breaking point? Paying over $175,000 in taxes (in one year!) and still getting hit with a surprise $33,000 tax bill. He knew there had to be a better way to not only make a living but also build long-term wealth, and after a few conversations, he plunged headfirst into real estate investing—taking down five deals in just six years!

In this episode, you’ll learn how real estate tax benefits often outweigh cash flow, appreciation, and loan paydown in many cases—especially if you’re a high-income earner or full-time investor. But that’s not all. Stick around, and Ross will also share the real estate side hustle he uses to furnish and renovate his rentals and travel for free!

In This Episode We Cover

How Ross went from job burnout to building a five-property portfolio

How to potentially save thousands on taxes with rental properties

The real estate side hustle that could help pay for your next vacation

The biggest keys to a successful real estate investing partnership

How to drastically reduce your living expenses with the house hacking strategy

And So Much More!

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Annie Kagan

The AI-powered Podcast Player