How to Build a 5 Star Business with a Fully Remote Team - with Hailie Marie Anderson

The Boostly Podcast

🎙 Welcome back to the Episode 797 of Boostly Podcast! 🎙👋

Welcome to Boostly, where we give STR and MTR owners and managers the tools, strategies, and support to win more direct bookings — no fluff, no ads.

In this Boostly Bootcamp session, Mark Simpson is joined by Hailey Marie Anderson, a 22-year-old Airbnb entrepreneur who built a 7-figure arbitrage business with 58 properties — all fully remote. Hailey reveals how she went from high school side hustles to running an empire by mastering three key steps: automate, delegate, and scale.

She breaks down the difference between CEO vs operator mindset, how to run time audits to spot your biggest time wasters, and why burnout, micromanaging, and limited scalability disappear once you hire a remote team. You’ll discover the exact roles she outsourced first (VAs, cleaners, handymen, runners), where to find them, and how to train and retain them with SOPs and checklists.Hailey also shares her tech stack — Hostaway, PriceLabs, Turno, Truvia, TouchStay, Bestie AI, and Discord — and explains how she integrates teams and tools to keep occupancy above 90% while traveling the world as a digital nomad. From guest communication automations to video guidebooks and guest verification, every process is systemized for five-star consistency.

Let's jump in.

💡 This video is part of our free training series to help you grow your short-term rental business and take control away from OTAs.

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