TRS 029: From Family Business Owner to Digital Nomad Entrepreneur with Mark Simpson

TRS 029: From Family Business Owner to Digital Nomad Entrepreneur with Mark Simpson

Today on That Remote Show I am joined by my friend Mark Simpson. Mark and I first got in touch after he joined the Varna Digital Nomads group this past summer and I quickly became very curious about his business Boostly which helps short stay accomodation owners to improve their marketing in order to get more direct bookings and not have to rely on sites like or Expedia.

Not only has Mark been able to grow Boosly from an in-person coaching service to a huge online community with hundreds of customers, but he has been able to do it while traveling full time with his wife and 3 sons and in this interview we dive into just how he was able to do this in a relatively short amount of time and Mark’s top tips for working on the road.

What You’ll Learn

  • What made Mark head over to Spain
  • How Mark’s childhood inspired him to start traveling
  • How Mark used his experience at Yelp to help grow his family business
  • How Mark transitioned from running his family business, to teaching others grow their short stay accommodation business
  • How Mark used post cards to get his first clients
  • Why Mark decided to take his coaching and turn it into an online course and how he did it
  • Why it’s good to continue working directly with clients even after you’ve created a “one to many” model
  • How Mark has been able to outsource 80% of his work in order to work just 3 hours a day
  • The SOP structure Mark has used to help him manage a growing remote staff
  • How Mark is able to hire the best people from all over the world
  • What made Mark settle down in Varna, Bulgaria for the summer after traveling the world


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