Financial Freedom with Rentals After 3 Years of Pure Hustle

BiggerPockets Real Estate Podcast

BiggerPockets

Education, Business, Investing

4.8 • 16.5K Ratings

🗓️ 14 July 2025

⏱️ 41 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

After hearing this episode, you’ll have no excuse not to reach financial freedom in under a decade. Today’s guest did it in even less time, scaling up to income-replacing cash flow in just a matter of years, even with a very demanding full-time job and constantly moving around the country. Through pure hustle, Taylor Wing is now financially independent in his late twenties with a sizable rental property portfolio that spits out cash flow to pay for his South Florida lifestyle. He’s got so many tricks to reach financial freedom faster, but his best piece of advice? The number of rentals you own doesn’t matter. Taylor was a full-time military member, serving in the Army for the first five years of his career, bouncing between North Carolina, South Dakota, and beyond. Wherever he was stationed, he began buying houses as soon as possible. That meant Taylor spent almost every hour of the day working, either at his job or on his rental property portfolio, for years straight. Was it a grind? Yes. Was it worth it? 100%. Now, fast forward seven years after graduating from West Point, and his family is financially free. He has his beautiful house on the water in Florida and is spending more time with his new (and growing!) family. Through “rebalancing” his rental portfolio, strategically using “reverse 1031 exchanges,” and other savvy strategies, Taylor is now in complete control of his time. He’s teaching you how to do the same today! In This Episode We Cover Why “unit count” doesn’t matter for financial freedom, but cash flow does Buying rentals in multiple markets and how to maximize your profit with medium-term rentals Why every real estate investor MUST review and “rebalance” their rental portfolio (or it’ll cost them) How to do a “reverse 1031 exchange” and move your headache rentals into better cash-flowing real estate The $140,000 properties Taylor is buying today that make $300-$400/month cash flow! And So Much More! Check out more resources from this show on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠BiggerPockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.biggerpockets.com/blog/real-estate-1147 Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠[email protected]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	This investor started with a single house hack.
0:03.5	Three years later, he had more than 30 rental properties and was able to transition out
0:08.0	of his demanding military career and into the life he always envisioned for his family.
0:13.9	Now he's acquiring multiple new properties per year, but he spends most of his time leaning
0:18.5	into what he calls the Florida lifestyle.
0:21.5	This isn't some secret formula that you can't execute.
0:24.8	It's the result of following a reliable, sustainable path to invest it.
0:29.1	Let's hear how it works.
0:35.3	What's up, everyone? I'm Dave Meyer.
0:37.3	I've been buying rental properties for 15 years, and on this
0:40.7	podcast, we teach you how to achieve financial freedom through real estate investing.
0:46.0	Today's guest is investor Taylor Wing. Taylor started his investing career when he was an
0:51.7	active duty army officer looking for the financial security
0:55.3	that would allow him to leave the military when his service commitment was up.
0:59.8	He started with just a single house hack and was able to grow his portfolio to more than 30
1:05.6	units across three different markets in just three years. That real estate investing has allowed him now to
1:12.7	prioritize his family's lifestyle, live where he wanted, and to find a new career that's
1:18.6	fulfilling for him at this stage of life. Taylor shared some of his story a few years back on this
1:24.8	podcast on episode 677, but I wanted to have him back on the show
1:29.3	because a lot has changed in his investing since then.
1:32.6	He still has around 30 units, but many of those properties have turned over as he's looked
1:38.7	to simplify his investing so he can spend more time with his growing family.
	...

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