This week, we sit down with our friend and community leader Emily Karasek, founder of Extend Your Stay. Emily spent 13 years as a nurse before realizing she couldn’t see herself in that role until 65, and she turned to real estate, starting with a flip in 2021, to create a different path. We talk with Emily about how she moved from a long-term rental she hated, self-managing, into mid-term rentals serving travel professionals, and how that “one deal” snowballed into a full-blown MTR management company now overseeing 40+ doors.

Together, we dig into what it really looks like to scale: buying imperfect deals, making mistakes, and relying on local meetups, community, and word of mouth instead of having everything perfectly planned. Emily opens up about hiring and leadership—from failed VA hires to finally finding the right one with Airbnb experience, and how she onboarded slowly, with clear expectations and guardrails, instead of dumping everything on her at once. She also walks us through the systems and tools behind her lean operation: Hospitable, Furnished Finder, Notion, Slack, OpenPhone/QO, and Relay. Plus, she dives into how she’s using AI and a custom GPT internally to house SOPs, property quirks, and FAQs so her team isn’t dependent on her brain 24/7.

If you’re a female investor, nurse, or mom who wants to build mid-term rentals, protect your time, and step into true leadership, you’re going to love this conversation with Emily.

Resources:

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WIIRE 224: How I Manage 40+ Midterm Rentals With a Team of 3 (Without Burning Out)