5 Properties in 6 Years After Extreme Job Burnout & HUGE Tax Bills

Episode #650

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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!

00:00 Intro
00:54 Paying $175K in Taxes?!
04:36 Ross’s Big Mindset Shift
11:58 Taking Down His First Deal
15:14 “Stacking” Rental Properties
21:44 Ross’s Portfolio (5+ Deals!)
25:56 Travel Hacking 101
30:38 BEST Credit Card Tracking Tools
41:10 Connect with Ross!