But it wasn't until she approached Drew Wanderman, who she met through a mutual friend, that she decided to develop weekendhouseswap.com, a site for people to post their homes and swap with other people for a weekend, for free.
"I have a technical background, but not so much experience with websites," Wanderman said. She thought it was a great idea and liked the chance of learning more working with websites and house swapping, something she's never done.
The site went live in mid-February and lists sections similar to Craigslist. Currently there are postings in San Francisco, Gold Country, San Jose, Los Angeles, one in the section "other states." Other areas listed are Mendocino, Yosemite, Monterey/Carmel, East Bay, Peninsula, Sacramento, Tahoe, Other California, Marin, Santa Cruz and New York City.
The audience for WeekendHouseSwap is people looking to drive a couple hours away, such as someone from Palo Alto who might want to go to Monterey or Carmel, which Finkelstein said can be expensive for someone staying overnight. But people can choose to go wherever they want, whether that be Los Angeles or somewhere out of state. They can also choose to trade for more than a weekend if both parties agree to it.
"People can use it how they want," Finkelstein said. "We are just facilitating a connection."
To build the site, they first hired a man in Boston, who they found from researching tech developers. They then found a man in Poland, who has worked on adding to the site, as well as a person in San Jose, who Wanderman said is also teaching her so she can do some of the maintenance.
Finklenstein expects early adapters to be those who are already comfortable with the idea of swapping; knowing that they'll be in someone else's house might increase the comfort level of having a swapper in theirs, she said.
Several listings are currently on the site, but nobody has swapped yet.
Andrea Jadwin, a friend of Finkelsteins, posted on the site because she is interested in local swapping, she said.
She has swapped with houses internationally and said she feels safe swapping with people because of her positive experiences.
"I think it's a great idea because it's free and local," she said. "You have to do your homework and get to know the people."
Lisa Victor, another friend of Finkelstein's, has been a member of HomeExchange.com, but said she likes the idea of this site because it allows an impromptu trip.
"There's so much on other sites," she said. "There are exchanges all over the world. This is small and easy. It's easy to take a little weekend trip. We can say 'Oh, let's go to Napa!'"
One way to look at house swap, according to Finkelstein, is to imagine a good friend, or a house-sitter, is staying at your house while you are out of town, and said a house is safer and better protected with someone staying there than remaining empty. They encourage members to do their best to learn about their swap partners before they swap and should only swap with people they feel comfortable sharing their home with.
Finkelstein swapped with a fellow dog owner, which she said was one of the more special parts of the trip and worked because they were both familiar with dogs. During her other swap in New York, the other family, who didn't own a dog, enjoyed taking care of Finkelstein's dog despite not knowing what to expect.
Discussing these types of situations, and other general expectations, before swapping with somebody is what Finkelstein said is most important.
Finkelstein and Wanderman researched other house-swapping sites, such as in Europe, and found them unclear on rules and agreements and added the ability to talk with their new swap-mate beforehand so they would all be clear about expectations.
Wanderman referenced the recent trend in sharing, such as with books (Finkelstein has swapped on Paperbackswap.com and Swaptree for free) and zip cars, the mentality of younger generations and how people might feel comfortable with the idea of swapping.
"There's much more of a community feeling," Wanderman said. "Young people have this belief that you don't have to own everything."
People won't be as concerned about finding an exact match to their own home, they said, because the swap is short and free.
Making money from the site is something they said they are not focused on, even though they invested money to start and grow the site, Finkelstein said. They will see what happens as more people start to use it and then may look into making a profit.
"If a lot of people use it, we may start using ads," Wanderman said. "It's not important and we don't know where the site will go."
Unknown advantages of swapping might be building connections and making new friends in the city someone stays in, which Finkelstein said happened for her when she stayed in New York. People who swap are meant to feel more like locals because they are not staying in a hotel or motel.
Once the site builds up more, both plan on using it. Wanderman has never swapped houses before.
"When I go away, I go far away," she said. "I don't have time to get away for a weekend."
Finkelstein added it will be great for all ages.
"When my daughter was little, I would have given anything to swap for a house with a pool," she said. "Now that's she older, my husband and I can drop everything and go somewhere."
Her husband was first wary of traveling far to a stranger's house, but would now swap "in a heartbeat."
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