How to Build a 5 Star Business with a Fully Remote Team - with Hailie Marie Anderson
The Boostly Podcast
Mark Simpson
5.0 • 302 Ratings
🗓️ 21 September 2025
⏱️ 70 minutes
🧾️ Download transcript
Summary
🎙 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.
Connect with Boostly
https://Boostly.co.uk
https://Boostly.co.uk/5steps
https://instagram.com/boostlyuk
https://Boostly.co.uk/podcast
Transcript
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| 0:00.0 | Can we all just say hi Haley? |
| 0:02.0 | We can show some love because I'm really looking forward to this session today. |
| 0:07.0 | We've got 45 slides, four five slides to really crack on with today. |
| 0:14.0 | Feddy had 44 yesterday, so we're beating it by two. Well done, Haley. |
| 0:20.0 | We're going to absolutely flow through. |
| 0:23.2 | What I realized yesterday is sometimes you take a little bit to get going with the questions in |
| 0:30.1 | the Zoom. So please don't be shy. There's no silly questions. This is such an important topic because, |
| 0:35.9 | again, so many people struggle when it comes to building a business that is truly one that they feel like, can we run like clockwork? |
| 0:43.9 | And I've gone through the presentation and it is unbelievably good. |
| 0:47.8 | I'm so glad that we're able to put this to the world. |
| 0:49.9 | So Haley, thank you very much. |
| 0:52.0 | So I'm going to pass the floor over to your good self. |
| 0:55.1 | Before we do, can everybody please let me know where you are tuning in from around the world? |
| 0:59.7 | We've had Saudi Arabia. |
| 1:01.6 | We've had Dominican Republic. |
| 1:04.4 | We've had, obviously, the US, the UK. |
| 1:07.5 | I'm looking for those lovely, we had Kenya. |
| 1:10.2 | So worldwide audience. Worldwide audience. Rob's those lovely. We had Kenya. So worldwide audience, worldwide audience. |
| 1:13.3 | Rob's in Florida. Hey, Rob. Uh, Anne's in Southwest Scotland. Matt's in Michigan. |
| 1:20.1 | We've got New York, North Carolina, Dallas. Um, somebody's also dropping in their website domains. |
| 1:25.1 | I love that. All right. Miss Haley Marie Anderson, |
| 1:29.1 | the floor is yours. Thank you for doing this. I'll let you go. Yeah. Well, thanks for having me. |
... |
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