How to Build a Wildly Successful Short-Term Rental Company

Today's Guests: James Svetec & Riley Oickle

One of the world's foremost Airbnb experts and the co-author of Airbnb for Dummies, James has helped over 1,000 students all over the globe leverage the power of short-term rentals as a vehicle for cash flow and wealth. James is the industry's go-to expert when it comes to mastering performance and streamlining operations. He consults with more than 600 property management companies around the world.

Riley is a Canadian real estate investor and mentor who specializes in multi-family residential investing through BRRRR and joint venture strategies. Throughout the journey of buying his first income property in the Southwestern Ontario area, he realized that there is a real need in the market to help people go through this process more easily. Today, he owns a real estate portfolio worth over $8 million and has helped new investors buy their first properties without wasting time and money on trial and error.

Highlights From The Show:

We start, as we always do, with my guests providing us with a bit of their background and how they got into real estate investing. Riley originally went the multi-family investing route and James was managing short-term rentals for other owners. They met through a mutual contractor, realized they had complementary skills, and decided to begin investing in short-term rentals together. Additionally, they do short-term rental coaching.


I observed that the short-term rental industry existed before COVID but that it had exploded because of peoples’ need for a safer environment than a hotel when traveling. I asked the guys several questions pertaining to this so that we could dig into the state of the short-term rental industry in 2023. James pointed out another factor to this was that more people were staycation-ing because they didn’t want to get on airplanes to travel. Many of the STRs in rural areas within easy driving distance of large cities experienced a boom as well. He said overall the industry is still trending up from pre-COVID numbers, but it has slowed down somewhat as the pandemic fears have decreased.


We talk about market and property evaluation, market area regulations, resources for aggregating data, common mistakes, various portfolio-building ideas, and so much more! Make sure you don’t miss another amazing episode of the Just Start Real Estate Podcast with James Svetec and Riley Oickle and learn how to build a wildly successful short-term rental company!

Notable Quotes:

“So they were like dog years basically.”

  • Mike Simmons


“Complete immersion in investing is different than dabbling on and off as a hobby for 10 years.”

  • Mike Simmons


“I was totally immersed in the short-term rental and Airbnb space, but I had never bought and owned my own property.”

  • James Svetec


“We each had those complementary skill sets.”

  • James Svetec


“There is the bird’s eye view which is market analysis and then the more micro level which is property analysis. If someone has investing experience, they would be familiar with both.”

  • Riley Oickle


“We not only look at what the regulations are in a particular area but where we suspect they might go in the future.”

  • James Svetec


“Those properties are very expensive because the area is very prestigious.”

  • James Svetec


“I wouldn’t say that an area having no regulations is a red flag, but it is a yellow flag, for sure.”

  • James Svetec


“It is boring, but you need to read the actual regulation, not an article in the local paper outlining what they think the regulations are.”

  • James Svetec


“The AirDNA data is really solid if you know how to use it.”

  • James Svetec


“I call it paper napkin math.”

  • Riley Oickle


“Beginning investors often evaluate properties based on emotion and that just doesn’t work. You need to be very analytical.”

  • Riley Oickle


“There is no way around it - if you want to do something right the first time and save money and time, you get a coach, you find a mentor, a mastermind.”

  • Mike Simmons


“I am just geeking out on all of the stuff you talked about.”

  • Mike Simmons


Thank You for Listening!


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Resources and Links From Today's Show:




Motel Makeovers

BNB Inner Circle

James on Instagram

Riley on Instagram


More Resources From Mike: