From Job Burnout to “Stacking” 5 Properties in Just 6 Years

Real Estate Rookie December 9, 2025
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Real Estate Rookie

@realestaterookie

About

Ready to buy your first rental property and start making passive income? We're here to help. On the Real Estate Rookie channel, we highlight the stories of investing newbies getting their first, second, third, or tenth real estate deal. Rental properties? We've got you covered. Fix and flips? That's our thing! Wholesaling? Rental arbitrage? Short-term rentals? We've got videos for you too! Tune in on Tuesdays for in-depth interviews with rookies, just like you, taking their first steps to build wealth. Then join us on Thursdays as we answer YOUR real estate investing questions in our weekly Rookie Reply Q&As! Don't know where to start? Click the link below!

Video Description

Episode #650 Get Fast, Affordable Landlord Insurance with Steadily: https://steadily.com/?utm_source=biggerpockets&utm_medium=youtube Episode Show Notes: https://lnk.to/realestaterookieYT Join BiggerPockets for FREE 👇 https://www.biggerpockets.com/signup?utm_source=owned_media Buy the Book, _Rich Dad Poor Dad_ : https://store.biggerpockets.com/products/rich-dad-poor-dad?utm_source=youtube&utm_medium=description&utm_campaign=none Sign Up for the Real Estate Rookie Newsletter: https://www.biggerpockets.com/email-subscribe?utm_source=youtube&utm_medium=description&utm_campaign=none Find an Investor-Friendly Agent in Your Area: http://biggerpockets.com/agentmatch _Real Estate Rookie_ 286 – Rookie Reply: Real Estate “Travel Hacks” We Use to Score FREE Vacations: https://www.biggerpockets.com/blog/rookie-286?utm_source=youtube&utm_medium=description&utm_campaign=none Connect with Ross: https://www.biggerpockets.com/users/rossa61?utm_source=youtube&utm_medium=description&utm_campaign=none Connect with Ashley and Tony: Ashley: https://www.biggerpockets.com/users/ashkehr?utm_source=youtube&utm_medium=description&utm_campaign=none Tony: https://www.biggerpockets.com/users/tonyr75?utm_source=youtube&utm_medium=description&utm_campaign=none 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!

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