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

BiggerPockets Real Estate Podcast · Apr 27, 2026 · 34m

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.

He was a sophomore in college. Could he really buy his first house?

Thankfully, he had been saving up for tuition since high school, but an academic scholarship now put the entire down payment in his hands. He pitched his parents on cosigning, and next thing you know, he was…