Into the Weeds of the Operations of an Airbnb Business, Part II—with David Golshan (Ep422)

Into the Weeds of the Operations of an Airbnb Business, Part II—with David Golshan (Ep422)

Are you looking to scale your Airbnb hosting business? If so, you need to hire an operations manager sooner rather than later.

But should you hire a virtual ops manager to oversee your team? Or do you need an operations manager on the ground in the community?

David Golshan is the founder of StayWithDave, a short-term rental business out of Los Angeles, California. He started hosting on Airbnb seven years ago, growing a portfolio of 50 units through rental arbitrage. Forced to downsize in the pandemic, Dave currently has 15 listings, and he is rebuilding his hosting business in the management model.

On this episode of Get Paid for Your Pad, Dave returns for Part II of our discussion on Airbnb operations. We chat about the process of hiring a virtual operations manager for a STR business, exploring the best way to train someone for the role and the benefit of conducting a monthly review with your team.

Dave asks about our vision for outsourcing the management of Freewyld, the STR brand Eric and I are building, and I explain why guests in secondary markets want to build a personal connection with their hosts—and how that impacts our operations.

Listen in for insight on operating in a highly regulated city like Los Angeles and learn how to choose an Airbnb-friendly market that’s the right fit for you!

Topics Covered

Dave’s journey as an Airbnb host

  • Grew portfolio to 50 arbitrage units in 5 years
  • Downsize to 15 properties during pandemic
  • Rebuilding business in management model

The benefit of owning short-term rentals

  • Best way to build long-term wealth
  • Real estate appreciates in value

Dave’s process for hiring a virtual operations manager

  • Serve as integrator to oversee VAs + vendors
  • Training through Loom and job score card

Why I suggest monthly review meetings for your team

  • Shifts dynamic among team
  • Motivates all to up game (even owners)

How we create a connection with guests at Freewyld

  • Onsite host lives in each community
  • Add general manager for portfolio as scale

My insight on STR hosting in highly regulated cities

  • Decide if willing to operate in gray zone
  • Must be comfortable with uncertainty

The pros and cons of hosting in a vacation city

  • More competition but fully legal
  • Takes longer to scale but more sustainable

Tips for choosing STR-friendly markets to focus on

  • Bring value to community for long term
  • Places where you already have listings

Connect with Dave


StayWithDave on Instagram


Into the Weeds of the Operations of an Airbnb Business, Part I on GPFYP EP420

Harold Gonzalez on GPFYP EP369



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