RG 179 – Disrupting the Short Term Housing Market with Rob Stephens

Rob is the co-founder of Avalara MyLodgeTax which is the leading provider of tax compliance solutions for the vacation rental industry. The company was founded by a group of rental owners including Rob who knew the stress of managing holiday rentals and keeping up with tax compliance so their goal is to help others stay compliant with regulations and tax law. Rob made his first dollar as a child when he inherited a paper route from his brother and started to make $30-£50 a month. Rob grew up in Colorado and was really into skiing, this was also where he met his wife. In 1999 they wanted to get a second property but didn’t have the income to afford it, so they decided that they could do a rental. 

At the time rental management companies in Colorado charged 40-50% of rent so they decided to do it themselves. This was the early days of the internet and they came across brbo.com which is now owned by Expedia. They listed their condo for $120 a year and attracted global travellers and were able to generate $30-40,000 per year in rent. It was a great experience but they ran into lots of problems with occupancy taxes and realised that it this was a problem for them (they were CPA’s) they other people would definitely be struggling as the internet property boom grew. There were so many moving parts with payment registration and then monthly/quarterly payments but no reminders or notifications.

They started their company in 2003 and have had many lessons learned; the most important one is that software development always takes longer than you expect because everyone is competing for the same engineers. Company success is not an overnight thing, they’ve done better in the last 5 years and tax becomes a more common narrative.

Top tips 

  • Habit – Self discipline and exercise
  • Person – His boss when he left Arthur Anderson who taught him a lot
  • mylodgetax.com

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