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

Podcast: Women Invest in Real Estate · Amelia McGee & Grace Gudenkauf

Opublikowano: 2026-09-28

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 bre...