He Bought His First Rental at 20. Now at 29, He Cash Flows $20K/Month.
BiggerPockets Real Estate Podcast
BiggerPockets
4.8 • 16.6K Ratings
🗓️ 27 April 2026
⏱️ 38 minutes
🧾️ Download transcript
Summary
Transcript
Click on a timestamp to play from that location
| 0:00.0 | At 20 years old, Jefferson Simmons was kicked out of his frat house. |
| 0:04.2 | The entire property was getting remodeled, and so he and 47 other college kids needed a place to live. |
| 0:11.0 | After being discouraged by the rentals he saw in his area, he switched his Zillow tab from rent to buy and saw a $250,000 house for sale. |
| 0:20.7 | But he was a sophomore in college. Could he really buy his first house? and saw a $250,000 house for sale. |
| 0:22.5 | But he was a sophomore in college. |
| 0:24.9 | Could he really buy his first house? |
| 0:27.4 | Thankfully, he had been saving up since high school. |
| 0:29.2 | He pitched his parents to co-sign. |
| 0:34.4 | And next thing you know, he was renovating a basement to put as many frat friends in there as possible. |
| 0:35.6 | Suddenly, he was cash flowing $300 a month as a college kid. |
| 0:40.4 | And now, just nine years later, Jefferson is financially free with a rental portfolio of |
| 0:46.3 | 17 properties, cash flowing $20,000 a month. He even ditched law school to go all in on rentals. He built partnerships on a low |
| 0:56.6 | salary and he did everything he could to scale. Today, we're going to get the full story with exact |
| 1:02.7 | numbers, strategies, and techniques that Jefferson used to become a rental millionaire |
| 1:07.4 | before 30 years old and he's not done yet. |
| 1:16.4 | Music rental millionaire before 30 years old, and he's not done yet. Jefferson, welcome to the Bigger Pockets podcast. |
| 1:19.0 | Thanks so much for being here. |
| 1:20.5 | Dave, thanks for having me. |
| 1:21.7 | This has been a longtime dream of mine. |
| 1:24.1 | Well, we're excited to hear about your story. |
| 1:26.1 | This should be a lot of fun. |
| 1:27.2 | So start by |
... |
Please login to see the full transcript.
Disclaimer: The podcast and artwork embedded on this page are from BiggerPockets, and are the property of its owner and not affiliated with or endorsed by Tapesearch.
Generated transcripts are the property of BiggerPockets and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.
Copyright © Tapesearch 2026.

