NASHVILLE, Tenn. – She started with a bobby pin.
Then she traded jewelry, a skateboard, Air Jordans, iPhones, a year’s worth of burritos, several cars, three tractors and a Tesla food truck, and ended up with a house.
Demi Skipper was a 29-year-old newlywed working at home during the pandemic giving advice to people about how to save money with a tech app when she decided to try something crazy.
In May 2020, Skipper set out with this idea: trade a bobby pin for a house. That sounds impossibly insane, but you can follow every step she took on social media. She sent 300,000 trade proposal emails, she joined so many Facebook groups that the social media company thought she was a bot and banned her (temporarily) and she traveled across the United States and Canada to complete her mission.
Today she is world famous with 5.1 million TikTok followers (more than even Paris Hilton, who became part of Skipper’s journey). She has made television appearances on networks around the world and she has a corporate sponsor.
Oh, and she has a new house in Clarksville, Tennessee, for which she paid one bobby pin.
“I’ve always been into weird side hustles,” Skipper said, reached at her home in San Francisco. This hustle is no longer on the side.
She was set to arrive in Tennessee on Jan. 8, and her and her husband Bobby Sudekum will oversee the renovations on their new house.
They’ll stay in an AirBnB nearby until the place is ready.
And then, you won’t believe what Demi Skipper is going to do with that house.
Side hustle success
She was an architecture student at the University of Virginia. She took a job designing computer maps at Apple, and she moved to San Francisco.
While doing her day job, she got the idea to buy used wedding dresses and rent them out. That side hustle was so successful it became too much. She said she stopped doing it after she rented more than a thousand wedding dresses. She is still in the process of selling all her used wedding dresses.
Her ideas weren’t always successful. She once started doing laundry and dry cleaning for corporations. People brought their laundry to work, Skipper would pick it up, clean it and return it for a fee.
“It was horrible,” she said. Too much work, too many logistical problems.
Skipper was sitting at home during the coronavirus lockdown when she saw a YouTube video of Kyle McDonald’s Ted Talk. McDonald became famous in 2006 when he traded a paper clip for a house. He wrote a book called “One Red Paperclip.”
She was disappointed she hadn’t thought of McDonald’s idea.
So Skipper decided to try it, and looked inside her house for something of no value. She considered a Q-Tip swab, but decided against it. She found a box of 100 bobby pins.
She pulled out one.
Skipper made a video of herself holding the bobby pin, asking who would trade something, anything, for this item of no value. “This bobby pin,” she said, “is going to be a house.”
She made three rules. 1) No trading with family or friends. 2) No spending money (except for a few shipping costs when otherwise unavoidable). 3) No trade backs.
At first, she got pushback. “All these people were thinking it was a ruse,” she said.
Her first trade: She flipped the bobby pin for a set of earrings, owned by a woman in Atlanta who hated them.
The trading continued, with each item more valuable than the last.
She knew the plan would be successful when she traded an old snowboard. She exchanged messages with a guy who needed the snowboard because he was going to the mountains that weekend.
Because his need was so high, he traded her an Apple TV.
“There is nothing that is going to stop me,” she thought after that trade.
Social media haters
The comments on her social media posts were less than encouraging. People wrote that she was stupid, and this would never work. They accused her of being a scam artist.
But she kept going.
There were 28 trades in total, all done on top of her 8 to 5 job.
Eventually got a pair of Air Jordans, which she flipped for an iPhone 11 Pro Max.
Things didn’t really explode until she signed up for TikTok. She made her first video with zero followers. And her following quickly grew to 5.1 million.
She traded the iPhone for a minivan.
The next morning the minivan wouldn’t start. She thought the whole quest might end there. Who was going to trade for a broken down vehicle?
So she slid beneath the car and made a video of its underside. A mechanic saw the video and explained how to fix it.
A priest traded an electric skateboard for the minivan. A skater in Oregon traded her a MacBook for the skateboard.
Along the way, she traded for an electric bicycle with a food cart attached to the front, a Honda CRV and three tractors.
She swapped the tractors with someone for a year’s worth of free Chipotle burritos (valued at $20,000).
Does Paris Hilton like Chipotle?
That’s when she tried to reach Paris Hilton. Would the television star/former it girl/mega rich socialite want a year’s worth of Chipotle?
In the email exchange with Hilton, Skipper pointed out that, at the time, she (Skipper) had more TikTok followers and this could boost Hilton’s credibility on that platform.
So Skipper swapped the burritos for a trailer with a Tesla power wall, solar panels and a refrigerator which could be a souped up food truck worth about $55,000.
The problem with the trailer was that it was in Canada, and she had to wait five months for the border to open during the pandemic.
During that downtime, she found a real estate agent in Tennessee.
Ciera and Bill Netherton of Legion Realty agreed to take the Tesla-powered trailer for an $80,000 house. The Nethertons plan to give away the trailer in a competition inspired by the Great Food Truck Race reality show.
“I was prepared for it to be a scam,” Skipper said.
It was real.
Ciera Netherton was impressed with Skipper.
“She just didn’t give up,” Netherton said. “If you have the drive, the only person standing in your way is you.”
The house has two bedrooms, two bathrooms and sits on just under an acre of land. She came to Tennessee, and Netherton presented her with the keys.
“I cried in the front yard,” Skipper said.
Her husband, who watched the whole journey unfold, said he was cheering when he heard she got the house.
“I don’t think crazy is the word I would use to describe her,” Sudekum said. “She’s really impressive. That’s the word. She willed her way through this.”
Her next venture
Demi Skipper learned some things about herself.
“I have to stop saying I’m lucky,” she said. “I have to give myself credit.”
With every trade, she learned something about people.
“I put so much trust in random strangers,” she said. “People are pretty good.”
Now that she has a house, in which renovations will be done in April or May, she’s got another idea.
This one may even be crazier than the trading of a bobby pin for a house.
“I’m going to trade the house for a bobby pin,” she said.
She’s a trader.
“I gotta give this house away,” she said. “Life is strange. Everybody has a dream.”
Follow reporter Keith Sharon on Twitter @KeithSharonTN.