VRS245 – How to Outsource and Other Vacation Rental Tips with Craig Reid

Are you doing dull, repetitive tasks that have you saying, “I shouldn’t be doing this”?

Is your time spent on boring jobs that prevent you from working on projects that can deliver much greater value to your business?

Is that a yes? I’m sure it is for many small business owners who plow through myriad little tasks to pave the way for the big stuff. But what mostly happens is that more minor work comes along to fill in the newly acquired time.

That was what was happening to me earlier this year as I found myself responding to email enquiries for hours a day. As soon as light appeared at the end of the tunnel, more arrived, and I was finishing my day exhausted knowing full-well that the next morning would bring with it a full inbox again.

My staff were busy on managing reservations, dealing with more complex enquiries and the marketing tasks I’d set for them. And I – partner in a moderately sized property management company – was using my day responding to questions on availability and pricing.

That was not sustainable in any way….and to confess more comprehensively..I’d been doing it for years. It was time to stop.

What caused me to finally put an end to this behavior was an intervention of sorts.

I’d mentioned my daily tasks on a podcast and was called out on it by a property manager from Australia.

Craig Reid from Profitable Holiday Homes emailed and asked me the question, “What could you achieve if you weren’t deep in minor operational tasks that anyone else could do”?

It got me thinking. And then acting.

We have a virtual assistant in the Philippines who has worked for us for several years doing data entry and small administrative tasks. It didn’t take much for us to train her to tackle the bulk of email enquiries. Then our office manager jumped in and created a roster for the rest of the staff to deal with the rest, even scheduling weekend cover.

And voilà – I’m free to work on my business and not in it.

Craig joins me in this episode to talk about how he outsources many of his companies administrative tasks and also to share some time-saving hacks and resources that allow him to focus on strategic management, and stay out of the operational weeds.

He shares:

  • The types of tasks to outsource
  • Why the summary line of an Upwork profile is important
  • Three reasons why he prefers workers from the Philippines
  • Why it’s important to be specific in describing a task
  • When to pay by the hour and when to offer a fixed price project
  • Why honesty is best when estimating work offered
  • The step by step process he uses for using Trello for managing remote staff
  • His best time-saving resources

And stay through to the end for Craig’s 2-minute love story. It’s worth it!

Links mentioned in this episode



365 Villas


Profitable Holiday Homes



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