Preview Mode Links will not work in preview mode

Welcome to Target Market Insights. A podcast to help real estate investors navigate neighborhoods through the lens of local experts. In each episode, we speak to local specialists to learn about their market, useful tips, and the latest trends and developments. This show is designed to help you with the insights you need to win your target market.

Sep 22, 2023

Meet Jessie Dillon, the entrepreneur rewriting the rules of real estate. Hailing from Hopedale, MA, Jessie's journey is a testament to relentless ambition. From Beauty to Real Estate: In 2021, Jessie transitioned from beauty to real estate, driven by a hunger for financial independence. Her timeline reads like a whirlwind - closing her first duplex in 2022, followed by a lucrative short-term rental deal and a savvy househack. In July 2023, she secured a 13-unit multifamily property and launched a profitable joint venture deal.


In this episode we talked to Jessie about her transition into real estate, her first deal in today’s tight market, partners and the vetting process, what her portfolio looks like today, and the power of social media.


Announcement: Join the Invest Beyond Multifamily Fall Conference here.




00:00 A transition into real estate investing;

05:29 A first deal in a tight market;

08:24 Partners & The vetting process;

13:28 Jessie’s portfolio today;

14:34 The power of social media;



Announcement: Join our Apartment Investing Mastermind



19:15 Round of Insights


Apparent Failure: Not being as profitable with her short-term rental as expected.

Digital Resource: Social media

Most Recommended Book: Discovering Your Dharma

Daily Habit: Sleeping a lot.

#1 Insight for Diving into Partnerships: Treat it like dating. You wouldn’t get engaged on the second phone call.

Best Place to Grab a Bite to Massachusetts: Monahan's Clam Shack


Contact Jessie:

You can find Jessie on Instagram.


Thank you for joining us for another great episode! If you’re enjoying the show, please LEAVE A RATING OR REVIEW,  and be sure to hit that subscribe button so you do not miss an episode.