BiggerPockets Real Estate Podcast — He Bought His First Rental at 20. Now at 29, He Cash Flows $20K/Month.

SCOUT· 60%34m·2026-04-27·Money

He Bought His First Rental at 20. Now at 29, He Cash Flows $20K/Month.

BiggerPockets Real Estate Podcast

At 20 years old, Jefferson Simmons was kicked out of his frat house. The entire property was getting remodeled, so he and 47 other college kids needed a place to live. Time to rent…right? After being discouraged by the rentals in his area, he switched his Zillow tab from “Rent” to “Buy” and saw a $250K house for sale.…

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He Bought His First Rental at 20. Now at 29, He Cash Flows $20K/Month.

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