The Boostly Podcast

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

Date: September 21, 2025
Host: Mark Simpson
Guest: Hailie Marie Anderson

Episode Overview

In this action-packed workshop episode, Mark Simpson is joined by hospitality entrepreneur Hailie Marie Anderson for a deep dive into building a high-performing, fully remote short-term rental business. At just 22 years old, Hailie shares how she scaled from 0 to 58 properties worldwide, all without owning a single one—and without ever being tied to a location.
The episode lays out her blueprints for automation, delegation, and scaling. Hailie details her journey, the systems and tech stack powering her operations, and the critical mindsets and processes necessary for hosts wanting to reclaim their time while delivering impeccable 5-star guest experiences.

Key Discussion Points & Insights

1. Who Is Hailie Marie Anderson? (02:18–04:27)

• Hailie started Airbnb arbitrage at 19, now operates 58 remotely managed units, traveling constantly as a digital nomad.
• "I rent all of my properties. I don't own any...I'm not physically required to be anywhere except where my laptop or my phone is." – Hailie (02:26)
• She’s run every aspect of her business remotely, thanks to robust systems and a fully remote team.

2. CEO vs. Operator Mindset (04:27–09:28)

• Many hosts fall into the trap of being an operator—stuck in daily tasks—rather than leading their businesses as true CEOs.
• Recognizing when you’re micromanaging is the first step to delegating and automating for growth.
• "To reach those new levels, you need a team. Every single big company has teams." – Hailie (05:51)

3. Time Audits: Identify & Eliminate Time Wasters (09:28–12:15)

• Conduct regular time audits to see where your hours go.
• "If you spent 40 minutes within this one hour doing guest communications, that is a red flag that...you can delegate this out for cheaper than what it would cost you per your hour." – Hailie (08:45)
• Most common time wasters: guest communications, cleaning coordination, pricing optimization, maintenance requests.

4. Remote Team Structure & Key Roles (13:14–15:13)

• Four core remote roles: Virtual Assistants (VAs), cleaning teams, handymen/runners, and revenue managers.
• VAs handle everything from guest comms to pricing, cleaners maintain quality, handymen handle fixes, runners manage tasks like last-minute supplies.
• "My team is 100% remote. We run a seven-figure business every single day." – Hailie (07:39)

5. Hiring, Training, and Retention (12:27–21:16)

• Hire VAs from platforms like Onlinejobs.ph, prioritize those with hospitality or OTA experience.
• Cleaners: use Turno for sourcing, ensure they have STR-specific experience.
• Handymen/runners: Thumbtack or cleaner’s networks; community Facebook groups as a secret weapon.
• Essential onboarding: document your processes from day one with Loom and written SOPs.
• "The goal is to take your brain and put it into someone else’s head...train them to basically be you." – Hailie (24:02)

Memorable Moment: The 'Husband and Wife Team' Phenomenon (15:55)

• Mark highlights that many find cleaning/handyman teams through husband-and-wife duos—a global short-term rental staple.

6. Managing a Scaling Team & Operations (17:49–25:45)

• Six VAs currently manage 58 properties, with expansion based on team feedback and workload, not strict formulas.
• Leadership structure: one head VA oversees the others, providing escalation support.
• Know when to add team based on transparency and honest communication about stress, workload, and capacity.
• Weekly team calls for connection and feedback; daily communication via Discord.

7. Processes, Systems & Task Management (25:45–41:21)

• Task and process documentation:
  • Training checklists (AM/PM/daily), guest journey workflows, FAQ/file systems
  • Track claims, bad reviews, and response strategies
• Tools: Asana (task/project management), Google Drive (documentation), Discord (team communications), TimeDoctor (performance tracking).
• "I track everything. Every claim, we track when we submit the claim, when it’s received, if we need to follow up..." – Hailie (32:03)
• Ongoing upgrades: transition legacy tracking from sheets to Asana for greater efficiency.

8. Tech Stack for Remote Hospitality Success (45:22–55:08)

• Property Management System: HostAway (centralizes calendars, comms, cleaning, etc.)
• Pricing: PriceLabs for data-driven, dynamic pricing.
• Cleaning: Turno for scheduling, checklists, and image verification.
• Guest Verification: Truvy (ID checks, automated workflows).
• Guest Experience: TouchStay virtual guidebooks (with videos/captions for accessibility).
• Automation/AI Messaging: Bestie AI (handles 50%+ of guest communications).
• Finance: TrueBooks (specialized hospitality bookkeeping/CPA), Payoneer (international payments).
• Team Communications: Discord across all roles/projects.

Notable Quote

"If you’re not using a PMS, I don’t know how you’re doing this – it centralizes literally everything." – Hailie (46:56)

Tech Stack Wisdom

• Mark: “There are loads of alternatives—what matters is finding what fits your flow and your team." (55:10)

9. Scaling Without Sacrificing Experience (58:27–61:46)

• Documented SOPs (Standard Operating Procedures) for every process ensure seamless onboarding and guest experience at scale.
• "With SOPs, you and your team can scale without adding stress...you need it." – Hailie (60:59)
• VAs are empowered to train new hires independently with SOPs and Loom recordings.

10. Lifestyle, Autonomy, and Community (61:46–62:45)

• Hailie’s system allows true location freedom—last year she ran her business from Japan, Thailand, and Greece.
• 857+ coaching students; open invitation to connect and learn.

11. Audience Q&A: Business, Outreach, and Opportunities (64:38–67:01)

• On finding landlords for arbitrage: “It’s really a volume game...100 outreaches a day outrun your competition.” (65:07)
• On management/PM invites: More legacy owners are seeking out nimble operators like Hailie for better guest experience and modern systems.

Notable Quotes & Memorable Moments

• On mindset:
  “Delegating and automating is not a reflection of my inability to do something...to reach those new levels, you need a team.” – Hailie (05:51)

• On guest standards:
  “If your guest pushes back on sharing their ID, you don’t host them.” – Hailie (56:54)

• On SOPs:
  “Without SOPs, adding more properties means adding more work...With SOPs, you rent and repeat.” – Hailie (60:45)

• On scaling and lifestyle:
  “I have the full-blown confidence I won’t be stressed onboarding 35 new properties...everything is seamless.” – Hailie (59:34)
  “I went to Southeast Asia, went to Europe, literally all with my laptop and my phone.” (62:36)

• Mark's admiration:
  “22 years old! I didn't know my ass from my elbow at 22. Look at you go. Which is amazing. Well done." – Mark (20:06)

Timestamps for Important Segments

• Hailie’s Introduction & Business Overview: 02:18–04:27
• CEO vs. Operator Mindset: 04:27–09:28
• Time Audits & Identifying Time Wasters: 09:28–12:15
• Remote Team Structure: 13:14–15:13
• Hiring, Training, and Retaining Team: 12:27–25:45
• SOPs & Operations Management: 25:45–41:21
• Managing Tasks and Performance: 39:00–41:21
• Tech Stack Deep Dive: 45:22–55:08
• Scaling, SOPs & Lifestyle: 58:27–62:45
• Q&A & Arbitrage Insights: 64:38–67:01

Actionable Takeaways

• Audit your time regularly; categorize and delegate low-value tasks.
• Build a remote team with clear roles and empower them with strong systems.
• Document all processes (video + written) for painless onboarding and scaling.
• Use a modern PMS and complementary tech stack to streamline operations.
• Embrace automation & AI as you scale, but don’t neglect personal touch in guest experience.
• Retain your team with daily communication, a supportive environment, and clear SOPs.
• Outsource everything that doesn’t require your personal involvement—and do more of what moves your business forward.

Connect With Hailie Marie Anderson

• Instagram: @hailiemaarie
• Coaching & Community: See Hailie’s Popple link (shared during the episode) for all contact details.
• Open to DMs for questions, collaboration, and coaching.

Missed the live session? Want to build a 5-star hospitality brand and enjoy real location independence?
Listen to the full episode and access supporting resources via the Boostly Podcast Facebook Group (recordings available for 7 days post-broadcast).