I Bought 3 Rentals Then Ran Out of Money…Now I Have 50 Units

BiggerPockets Real Estate Podcast

BiggerPockets

Education, Business, Investing

4.8 • 16.5K Ratings

🗓️ 3 November 2025

⏱️ 37 minutes

🔗️ Recording | iTunes | RSS

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Summary

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 ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠[email protected]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	This investor acquired 50 units and only put 1% down all since 2021.
0:06.6	No tricks, no scams, not even extreme leverage.
0:10.5	Just a lot of hustle to find the right deals and the courage to seek out partnerships within her network.
0:16.4	Stick around to hear how she went from a demanding job running a makeup salon onto the path towards
0:21.7	early retirement.
0:27.6	Hey everyone, I'm Dave Meyer. I've been investing in rental properties for 15 years now, and I am
0:33.7	the head of real estate investing here at Bigger Pockets. Our guest on the show today is investor Jesse Dillon.
0:40.3	Jesse lives in Massachusetts and had a hands-on day job owning a small business in 2021,
0:45.9	when she discovered real estate investing.
0:47.3	And now, less than five years later, she's completely transformed her financial future
0:53.1	with a portfolio of only seven properties.
0:56.3	In this episode, Jesse will tell us how sending a few awkward text messages completely changed
1:01.1	her investing trajectory, why her partners are excited to bring all the necessary cash to acquire
1:07.6	new properties, and why she's now pivoting back to cash flow after accomplishing
1:12.1	her biggest investing goal. This is a truly inspiring story that really emphasizes the power
1:18.9	of finding like-minded people you might already know within your own network. Let's bring on Jesse
1:24.8	to hear how she does it. Jesse, welcome to the Bigger Pockets podcast.
1:29.2	Thank you for being here. Yes, thank you for having me. I'm excited to have this conversation with
1:34.0	you. Start by telling us a little bit about yourself and where were you in life when you first
1:41.9	started thinking about real estate investing? So I'm Jesse Dillon. I live in central Massachusetts.
1:47.0	Half of my time I spend in real estate and the other half I spend working in and operating
1:53.0	my permanent makeup studio.
	...

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