He “Stacked” 5 Properties in 6 Years: Now He Lives and Travels for Free!

Real Estate Rookie

BiggerPockets

How To, Education, Business, Investing, Entrepreneurship

4.8 • 1.7K Ratings

🗓️ 8 December 2025

⏱️ 50 minutes

🔗️ Recording | iTunes | RSS

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Summary

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! 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! In This Episode We Cover Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	A $12,000 tax bill and 200 hotel nights later, Ross Elkhorn swore he'd never trade time for commissions again.
0:08.4	Five years later, his house hacks fund his freedom and his side hustle pays for his first class flights.
0:15.1	Today's guest proves that getting started really isn't as complicated as you think.
0:24.2	This is the Real Estate Rookie Podcast. I'm Ashley Care.
0:27.7	And I'm at Tony J. Robinson. And let's give a big warm welcome to Ross. Ross.
0:31.1	Thanks for joining us today, brother. Hey, thanks for having me, Ashley and Tony. This is a pretty
0:35.5	surreal moment. Got to listen to both your podcasts from
0:38.9	past five years. And, you know, I know we connected out at a in-person event. And I would have
0:44.9	been kicking myself if I didn't come say what's up. So yeah, really excited to dive into kind of how
0:49.6	you guys helped as well as just some strategies that I learned along the way. So excited to be here.
0:54.6	Yeah. And we're excited to learn from you too, Ross. I want to start off with, you've said that
0:59.4	2018's tax bill was your breaking point. What was going through your mind then? And what did
1:05.4	that moment teach you about actual wealth building? Yeah, absolutely. So I was a, just for some background, I was for 10
1:12.4	plus years of medical device and healthcare software sales rep. And as a lot of people know,
1:18.2	you're very high commission based. And in 2018, had a really good year, was renting with
1:25.0	three other guys in the Northern Virginia, D.C. area.
1:28.1	And yeah, at the end of the year, saw how much I made, saw how much I owed in taxes.
1:33.2	And then when January came around, realized I still had to stroke a massive check to the IRS.
1:38.1	And I was like, okay, what's going on here?
1:40.6	Like I invest in stocks.
1:41.9	I invest right in index funds. I have the, you know,
1:45.7	foundation in place from the beginning, but I had heard a long time that real estate was a
	...

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