I first heard about Airbnb in 2010 at a big gala in Jacksonville while chatting with this really cool, artsy couple that I’d come to admire during my time working in the arts community there. It seemed like a really fun escapist activity in and of itself; browsing the very unique homes of people all over the world. A couple years later, after talking to a close friend who was an actual early adopter, my wife and I decided to try it out on our first trip together to Chicago. We enjoyed it and continued to use the platform occasionally for our travels, but I was always extremely wary of the idea of allowing strangers into my own place. I could not get over that mental block and I figured I would never make the leap from being just a guest to an actual host.
In 2014 Kelly was living in a condo that she owned with her brother. Then in August she left DC to join me in Florida. She quit her job, relocated 725 miles away and got married all in the span of two weeks!! Her brother also quit his job to start his own business, so when she moved out he began renting out the space on Airbnb to cover the mortgage. This lasted for less than a year before the condo association ordered us to stop, and even though we were not the ones handling any of the operation, it was our first exposure to the hosting side of Airbnb.
Fast forward to late 2016, when we were in the midst of a very busy time flipping properties in Jacksonville. We were having some issues with a house in the Murray Hill neighborhood that we had rehabbed extensively for a flip. It was in a transitioning area but maybe still a little bit rough for some buyers, so it sat on the market for over a month. While the neighborhood was pretty safe, it was still an area where vacant homes were prone to burglary. Sure enough, this house was broken into and all the expensive new appliances were stolen. On a separate occasion, the back shed and HVAC cage had been tampered with. This wasn’t our first experience with appliance or HVAC theft and we were desperately seeking solutions. We discussed security cameras as a possible deterrent, which would require internet installation. We were also considering staging the home to improve its overall appeal, so Kelly suggested we try listing it on airbnb. If it’s gonna have furniture and internet service anyway, what have we got to lose? We stated that the house was for sale so guests would have to keep the place spotless and agree to showings with a 24-hour notice, but we offered it at incredible value so we really did not have any problems with getting bookings or managing guest expectations.
Eventually the house sold for a good price, we gained a little bit of extra cash flow and never had problems with burglars again. And since we did many flips, we simply moved the internet service and some of the furniture from house-to-house so that we could replicate the process. The hassle was minor, we were staging these homes anyway, and definitely worthwhile.
Once the floodgates were open, we ended up even listing our own personal home while on several weeks-long trips. This was after we had decided we would be moving to Miami, so in some ways psychologically it felt more like transition housing than our “personal home,” but it was still a huge step for me. And by the end of this incredibly successful trial period, we began to consider all of our units for airbnb. Certainly, not all investment properties are good for short term rentals, but we use short term renting strategically in our portfolio. I am not sure we will ever go back to renting our own primary residence out short term, but it definitely was the bridge that got us into “professional” Airbnb hosting.
