Uploaded April 2026 | Updated September 2026, 2 weeks ago
Episode #1270
Baselane: Automate your real estate finances with banking and AI-powered bookkeeping. Claim your $100 bonus!
baselane.com/lp/bigger-pockets/?utm_source=bigger_pockets&utm_campaign=bigger_pockets&utm_medium=YT-M
*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 *renovating a basement to fit as many frat friends as possible.*
Now, *just nine years later, Jefferson is financially free,* with a rental portfolio generating *$20,000/month in cash flow,* all before the age of thirty. Today, Jefferson shares why he ditched law school to invest, the *one thing that helped him scale his portfolio way faster,* and how he’s consistently found *underpriced deals* that give him stellar returns.
Episode Show Notes:
lnk.to/biggerpocketsYT
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5 Things College Students Can Do Right Now To Reach Financial Freedom Faster:
biggerpockets.com/blog/things-college-students-can-do-to-reach-financial-freedom?utm_source=youtube&utm_medium=description&utm_campaign=none
Connect with Jefferson:
biggerpockets.com/users/jeffersons12?utm_source=youtube&utm_medium=description&utm_campaign=none
Connect with Dave:
biggerpockets.com/users/davem27?utm_source=youtube&utm_medium=description&utm_campaign=none
00:00 Intro
01:16 First Rental at 20!
05:28 Cash Flowing in College
06:35 Out of Money…Now What?
10:32 Sponsor: Baselane!
11:27 $200,000 Renovation (SECOND Deal)
14:12 Dropping Out of Law School
16:14 Look for These Deals Now
20:12 Selling Stocks for Single-Family Rentals
22:51 Current Portfolio
24:05 Secret to Scaling Faster?
28:37 Best Real Estate Resource
Episode #1270
Baselane: Automate your real estate finances with banking and AI-powered bookkeeping. Claim your $100 bonus!
baselane.com/lp/bigger-pockets/?utm_source=bigger_pockets&utm_campaign=bigger_pockets&utm_medium=YT-M
*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 *renovating a basement to fit as many frat friends as possible.*
Now, *just nine years later, Jefferson is financially free,* with a rental portfolio generating *$20,000/month in cash flow,* all before the age of thirty. Today, Jefferson shares why he ditched law school to invest, the *one thing that helped him scale his portfolio way faster,* and how he’s consistently found *underpriced deals* that give him stellar returns.
Episode Show Notes:
lnk.to/biggerpocketsYT
Join BiggerPockets for FREE 👇
biggerpockets.com/signup?utm_source=owned_media
🎉Join us at the BiggerPockets Conference October 2-4 in Orlando. Buy tickets: biggerpockets.com/bpcon2026
Let Us Know What You Thought of the Show!
BiggerPockets.com/Podcastfeedback
Grab _The Book on Investing in Real Estate with No (and Low) Money Down_ :
store.biggerpockets.com/products/investing-in-real-estate-with-no-and-low-money-down?utm_source=owned_media
Sign Up for the BiggerPockets Real Estate Newsletter:
biggerpockets.com/email-subscribe?utm_source=youtube&utm_medium=description&utm_campaign=none
Find an Investor-Friendly Agent in Your Area:
biggerpockets.com/agentmatch
5 Things College Students Can Do Right Now To Reach Financial Freedom Faster:
biggerpockets.com/blog/things-college-students-can-do-to-reach-financial-freedom?utm_source=youtube&utm_medium=description&utm_campaign=none
Connect with Jefferson:
biggerpockets.com/users/jeffersons12?utm_source=youtube&utm_medium=description&utm_campaign=none
Connect with Dave:
biggerpockets.com/users/davem27?utm_source=youtube&utm_medium=description&utm_campaign=none
00:00 Intro
01:16 First Rental at 20!
05:28 Cash Flowing in College
06:35 Out of Money…Now What?
10:32 Sponsor: Baselane!
11:27 $200,000 Renovation (SECOND Deal)
14:12 Dropping Out of Law School
16:14 Look for These Deals Now
20:12 Selling Stocks for Single-Family Rentals
22:51 Current Portfolio
24:05 Secret to Scaling Faster?
28:37 Best Real Estate Resource
