November 3, 2025
I Bought 3 Rentals Then Ran Out of Money…Now I Have 50 Units
BiggerPockets Real Estate PodcastAbout this episode
Retirement seemed way too far away for Jessie Dillon . She was burnt out , in physical pain every day, and tired of working so hard. What could get her to the semi-retired lifestyle she wanted faster? Rental properties , of course. Now, just four years later, Jessie has thousands of dollars in monthly cash flow and over a million dollars in real estate equity . Her dreams of location-independence are coming to fruition soon, and she’s sharing how you can do it, too , even if you have less money than you need to invest. Jessie was hooked on real estate from the start, buying rentals while she was renting herself. But after three property purchases, she was strapped for cash —but she didn’t give up. By creating an ingenious partner-finding system , she found her money partner and bought a rental that changed her life (and made them $1,000,000 in the process). Now, she’s repeated the system multiple times, with 50 units on a 50/50 partnership . And she did it all while in her thirties. She’s giving away her exact system so anyone can take it, repeat it, and retire early! In This Episode We Cover How to invest in real estate after you’ve run out of money (you don’t have to wait to save up) The one rental property that made Jessie and her partner over $1,000,000 How much cash flow you should be making on every rental property you buy Jessie’s ingenious system for finding a real estate investing partner in your network Stop self-managing : why Jessie (and Dave) think you should hire a property manager And So Much More! Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/real-estate-1195 Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com . Learn more about your ad choices. Visit megaphone.fm/adchoices