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

FinancingProperty ManagementBehind-The-ScenesMid-Term RentalsLong-Term RentalsShort-Term RentalsThe Community
Written By Amelia McGee
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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 retreats

  • The 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 curve

  • Real numbers from Jessie’s 2024 business investments—from $10K on STR deal sourcing to legal, software, events, and team support

  • How 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:

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:

Amelia McGee
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EP 249: 4 Ways To Make More Money With Your Portfolio Before Year End