Uploaded March 2026 | Updated September 2026, 2 weeks ago
Episode #1258
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
*Six figures in cash flow per year from nine paid-off properties.* That’s the definition of a small, powerful, profitable rental property portfolio. And today’s guest, *Greg Roedersheimer, did it all within the last five years* by buying the type of property every tenant truly wants.
Back in 2007, Greg’s agent told him it was time to buy. Little did he know that in just a year, he would be unable to sell that property and would be *forced to become an accidental landlord.* 13 years later, after having his *pre-40s “midlife crisis,” Greg knew he needed a way out of corporate* with cash flow to replace his salary. He settled back into real estate, but this time the market was very different.
Through smart *partnerships, savvy saving, and targeting the exact type of property* that has the *most demand potential,* Greg has built a small, *financially freeing portfolio* that has allowed him to regain his time with his kids, dedicate hours to his hobbies, and partner up to make win-win deals for him, his partner, and his tenants!
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 Henry’s Book, _Real Estate Deal Maker_ :
store.biggerpockets.com/products/real-estate-deal-maker?utm_source=youtube&utm_medium=description&utm_campaign=none
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
_BiggerPockets Real Estate_ 1231 - Paycheck to Paycheck in His 40s, Millionaire in His 50s with “Boring” Rentals w/Neil Whitney:
biggerpockets.com/blog/real-estate-1231?utm_source=youtube&utm_medium=description&utm_campaign=none
Connect with Greg:
biggerpockets.com/users/gregoryr109?utm_source=youtube&utm_medium=description&utm_campaign=none
Connect with Henry:
biggerpockets.com/users/henryw22?utm_source=youtube&utm_medium=description&utm_campaign=none
00:00 Intro
02:12 Buying RIGHT Before the Crash
03:24 Cash-Flowing Condo in 2021
06:59 Repeating His First Rental
09:40 Buying What Tenants Want
11:13 Sponsor: Baselane!
19:12 Serious Value-Add (Equity Boost!)
24:35 Watch Before Partnering
28:37 Current Portfolio
30:33 Best Beginner Advice
Episode #1258
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
*Six figures in cash flow per year from nine paid-off properties.* That’s the definition of a small, powerful, profitable rental property portfolio. And today’s guest, *Greg Roedersheimer, did it all within the last five years* by buying the type of property every tenant truly wants.
Back in 2007, Greg’s agent told him it was time to buy. Little did he know that in just a year, he would be unable to sell that property and would be *forced to become an accidental landlord.* 13 years later, after having his *pre-40s “midlife crisis,” Greg knew he needed a way out of corporate* with cash flow to replace his salary. He settled back into real estate, but this time the market was very different.
Through smart *partnerships, savvy saving, and targeting the exact type of property* that has the *most demand potential,* Greg has built a small, *financially freeing portfolio* that has allowed him to regain his time with his kids, dedicate hours to his hobbies, and partner up to make win-win deals for him, his partner, and his tenants!
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 Henry’s Book, _Real Estate Deal Maker_ :
store.biggerpockets.com/products/real-estate-deal-maker?utm_source=youtube&utm_medium=description&utm_campaign=none
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
_BiggerPockets Real Estate_ 1231 - Paycheck to Paycheck in His 40s, Millionaire in His 50s with “Boring” Rentals w/Neil Whitney:
biggerpockets.com/blog/real-estate-1231?utm_source=youtube&utm_medium=description&utm_campaign=none
Connect with Greg:
biggerpockets.com/users/gregoryr109?utm_source=youtube&utm_medium=description&utm_campaign=none
Connect with Henry:
biggerpockets.com/users/henryw22?utm_source=youtube&utm_medium=description&utm_campaign=none
00:00 Intro
02:12 Buying RIGHT Before the Crash
03:24 Cash-Flowing Condo in 2021
06:59 Repeating His First Rental
09:40 Buying What Tenants Want
11:13 Sponsor: Baselane!
19:12 Serious Value-Add (Equity Boost!)
24:35 Watch Before Partnering
28:37 Current Portfolio
30:33 Best Beginner Advice
