VRS431 - Things I Wish I’d Known When Starting Out – and What I’ve Learned in 20 Years in STR Management

It’s been 20 years since I met up with the founder of Ontario’s first rental listing site, for an hour-long meeting which extended to over three and a half, as the ideas just kept on rolling.  The partnership that was formed that day has remained strong as we’ve together built an amazing business.

At this point it seemed a good time to reflect on what we’ve learned over those years, and how we’ll take that learning into the future.

Some things took a while to incorporate, because there was no one to network with at the beginning.  We weren’t sure of the best ways of managing and operating a rental business and it was a little like new parents seeking the manual for bringing up a child.  There was no such thing, and we relied on instinct and surreptitiously looking at what others were doing, and if their outcomes were what we wanted.

It was seat of the pants stuff.

Nowadays of course that is all different and there’s books, courses, videos and a gazillion ‘helpful’ suggestions on Facebook groups.  Nothing beats being there and doing it and learning from the mistakes.

In this episode I share some of the knowledge we’ve amassed along the way and some key practical things we’ve done (or wished we’d done), in the hope that it is helpful to you in some way.

I talk about:

  • What you need to do at the beginning of the business and why it’s about the end
  • The number one question a buyer will ask and why you need years to prepare for it
  • The top metrics to analyze every year (and some more frequently)
  • How to get your business running on rails (that means you can go on vacation)
  • The emergency situation on our emergency plan that was never going to happen (it did)
  • Why early adoption of tech is nothing to brag about
  • Making the most of events and networking
  • Some of the best podcast episodes over the years

Links mentioned:

How to Evaluate Your Success in Short-Term Rentals – Marcus Rader of Hostaway

How to Create a Short-Term Rental Exit Strategy – Jacobie Olin