Talking with strangers about money

Kim and I are back from our two-week tour through Florida, a sort of “vacation from our vacation”. We’ll resume our R.V. trip across the U.S. in a few weeks, but after crunching the numbers we realized it’d be more cost-effective (and time-efficient) to leave the motorhome in Savannah and drive the Mini Cooper across the Sunshine State. So that’s what we did.

Although most of our trip was about play, we both took some time to work. Following three days at Disney World, for instance, Kim joined a weekend retreat with a small group of entrepreneurial women. (Kim has spent all of her working life in the dental field; over the past six months, however, she’s been following Steve Chou’s program for creating an online store. She’s very proud that her endeavor has netted about $300 while Money Boss is thousands in the hole!) Meanwhile, I drank beer and smoked cigars in Tampa’s Ybor City.

Most of my “work” on the trip came through talking about personal finance with the people we met. You’d be surprised at how many conversations you can have about money if you allow yourself to be open to it.

Let me give you an example.

While in Miami, Kim and I stayed in a guesthouse we found on Airbnb. (I’m a huge fan of Airbnb. I’ve used it to find cheap places to stay all over the U.S. — and the world.) Our hosts were a Cuban couple with an entrepreneurial mindset. They used to have an outbuilding they used as an office. After the husband retired early from his job as a contractor, he converted the space into an amazing 400-square-foot living area, complete with bathroom and kitchen.

This guesthouse now supplements their income. At $120 per night, our hosts earn $20,000 to $30,000 every year — all from a space that might otherwise have gone unused. To me this is a win-win: They earn some extra money while we save on the ridiculous Miami hotel prices. (For more about this sort of thing, check out Paula Pant’s series of articles on how she became an Airbnb host.)

But the money conversations didn’t stop there! Continue reading