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Discussion – 


Discussion – 


Scaling a Remote Co-Hosting Business While Maintaining a 5-Star Guest Experience – with Sean McGregor (Ep390)

The best business strategy is a satisfied customer. And if you host one or two short-term rental properties, it’s fairly easy to earn five-star reviews on Airbnb. But how do you maintain a high-quality guest experience at scale? How do you rack up 2,000-plus reviews and keep a 4.99 rating?

Sean McGregor is the Founder and CEO (Chief Experience Officer) of Stay Work and Play Co-Hosting, otherwise known as SWAP Lofts. Sean and his wife Lindsey have been hosting on Airbnb since 2012, garnering 2,212 reviews and a 4.99 rating overall. Sean pivoted to the cohosting model during the pandemic, and so far, he has built a portfolio of 15 listings in five states. He is also an active member of our Legends X community.

On this episode of Get Paid for Your Pad, Sean joins me to explain how he pivoted his STR business during COVID, sharing what he did to connect with property owners and build his management portfolio. He discusses using Thumbtack to find good team members in a new location and walks us through his plans to scale SWAP. Listen in for Sean’s top four strategies for maintaining a five-star guest experience—even as you grow your STR business!

Topics Covered

How Sean got his start with short-term rentals

  • Helped then-girlfriend Lindsey host on Airbnb
  • Managed remotely during family trip to Europe

How Sean pivoted to cohosting during COVID

  • Draw on experience managing family property 
  • Find property owners in Facebook groups

How Sean uses Thumbtack to find team members

  • Hire photographer, cleaners, handyman, etc.
  • Narrow down by reviews, they bid on job

Why Sean pays for a photographer to do a 3D tour

  • Makes it easier for cleaners to bid on job
  • Help guests and team members find things

How Sean maintains a high guest satisfaction score

  • Make it as easy as possible to check in
  • Personal connection via text throughout stay
  • Make it right when things go wrong

Sean’s top strategy for getting a 5-star review

  • Write detailed, friendly review for guest
  • Text screenshot and they reciprocate

Sean’s plans to scale SWAP Co-Hosting 

  • Document processes through Legends X
  • Build team so business can run without him

What Sean did before he got into short-term rentals 

  • College VIP discount cards for students
  • Golf VIP (access to/discounts on courses)

Why Sean recommends the Legends X program

  • Accountability pods to stay engaged
  • Community going through similar things

Connect with Sean

Stay Work and Play Co-Hosting


The 4-Hour Workweek: Escape 9-5, Live Anywhere and Join the New Rich by Timothy Ferriss

‘Alive Time or Dead Time. What Will It Be?’ in the Daily Stoic


Matterport Virtual 3D Real Estate Tours


Julie George on Clubhouse

Legends X

Get Paid for Your Pad on YouTube

Email jasper@getpaidforyourpad.com 

Hostfully [Discount Code PAD]