WIIRE 250: How Much Do Investors Really Invest In Their Business?

We’re sitting down with our friend and WIIRE founding member Jessie Dillon (Hofstra) to have a real, numbers-on-the-table conversation about what it actually looks like to invest in yourself as a female real estate investor.

In this episode, we walk through Jessie’s journey from overbooked permanent makeup artist in Central Massachusetts to owning around 50 residential units—including house hacks, value‑add multifamily, and short‑term rentals. We talk about the “golden handcuffs,” why index funds alone weren’t enough, and how real estate became her path out of being tied to the chair.

Together, we break down:

How Jessie decided when to stop DIY‑ing and start paying for speed through coaching, bootcamps, and retreatsThe mindset shift from “I should figure this out alone” to “someone else already solved this problem”Why women especially struggle with fear of failure and how mentorship, accountability, and community shorten the learning curveReal numbers from Jessie’s 2024 business investments—from $10K on STR deal sourcing to legal, software, events, and team supportHow we (Grace and Amelia) have invested five and six figures into masterminds, mentors, and our team—and the trade‑offs behind those decisions

Listen to Jessie's previous episodes below:

Episode 22Episode 149Episode 197Episode 212

If you’re a woman in real estate wondering when to hire help, join a community, or invest in a mentor—and whether it’s “worth it”—this episode will challenge your excuses and expand your idea of what’s possible.

Resources:

Join our free webinar on October 7Follow Jessie on InstagramGet in touch with Envy Investment GroupGet on the waitlist for the WIIRE CommunityLeave us a review on Apple PodcastsLeave us a review on SpotifyJoin our private Facebook CommunityConnect with us on Instagram