From hairpin to house: woman who mastered ‘trading up’ realizes dream

After a year and a half of pouring blood, sweat and tears, Demi Skipper has successfully taken one single hair pin and traded it up all the way to a house.

In May this year, the Guardian spoke to her after she’d traded three tractors for one of only a few Chipotle celebrity cards in the world, worth about $20,000. She had been inspired by Kyle MacDonald, who in 2006 traded a red paperclip all the way to a house, and hoped to reach her goal by summer’s end.

Only a few months later than hoped, Skipper, who is 29, has been handed the keys to a little house near Nashville, Tennessee. No mortgage. No fees. And not a penny spent (except on shipping). The modest ‘fixer upper’ house, complete with a big garden, is her 28th trade since she embarked on her project in May 2020.

Skipper, who also has a full time job as a product lead at Cash App, set out on her journey during lockdown and documented it to her (then) zero TikTok followers.

“There were just so many negative people saying it wasn’t possible. I was willing to do this for five years if that’s what it took to get to the house.” She beams: “I wake up and I’m like ‘is this real?’ I have the house. I traded this from a bobby pin!”

When Skipper revealed one of her last trades – a Chipotle celebrity card – to her almost five million TikTok followers, she was met with an unexpected backlash of criticism. The card gives the owner unlimited free food from Chipotle for a year, plus a catered dinner for 50 people, and is worth about $20,000. Many said she had made the worst decision of her journey yet, and that she would never find someone who would trade it for an item of the same value.

Determined to prove them wrong, Skipper planned out her strategy to find her next trade. She began looking at celebrities who were big fans of the fast food chain. If a celebrity was so much as pictured eating Chipotle, they were probably on Skipper’s radar. A couple of NFL players were close to trading, but they fell through.

After months of searching, she got an email from “Chipotle’s biggest fan”, a woman called Alyssa who runs a flower company in Canada. Alyssa agreed to trade an off-the-grid trailer with a Tesla powerwall and solar panels worth $40,000 for the card.

After the trade was made official, Skipper got Alyssa on a call with representatives of Chipotle, which almost brought her to tears as she is such a big fan of their food. Skipper said: “That was a really cool moment. I found the one person who cares about this card. I found her in the world.” (Alyssa works at a women’s shelter and plans to donate some of the free Chipotle food to the shelter.)

But Skipper quickly fell from cloud nine as one of the most complicated battles of her trading journey was about to begin. After figuring out a way to get the trailer from Canada to the US with closed borders due to Covid, she was told that the wheels on the trailer were illegal in the US and couldn’t be replaced. The company that makes the trailers hadn’t “paid their dues” to the US Department of Transportation and until they did, Skipper’s trailer was stuck in Canada. After calling transportation department every day for weeks and offering to file the paperwork herself, she had to wait three months to be able to bring the trailer home.

Finally one of her followers volunteered to pick up the trailer and hold it on her drive near the US border, so Skipper and her husband decided to make the 15-hour road trip to Canada to see, photograph, and decorate the trailer. It turned out to be one of the most life-changing car journeys of Skipper’s life.

As they drove it home, Skipper immediately started looking for her next trade. She messaged a woman who showed some interest, and the two started chatting on the phone while Skipper’s husband drove.

The woman on the phone asked Skipper, “Are you sitting down?” before explaining that she was a house flipper who owned about 15 different houses at any given time. She had been following Skipper’s journey from the beginning and was waiting for the right trade – and this trailer was it. Skipper was being offered a house in Tennessee.

The day after Thanksgiving she was on a flight to Nashville, and after a meal with the woman she had saved in her phone as “Final House Lady”, she had the keys in her hand.

She ran up to the house and started crying in the huge front garden. The house – which has two small bedrooms, a kitchen, living room and a bathroom – was “perfect”.

Skipper and her husband are leaving their rental home in San Francisco and are moving to Tennessee to renovate and live in their house. There’s a plan in the works to trade the original bobby pin back for something and frame it in their new home.

The Trade Me project may look like a smooth journey – it was anything but. From broken cars to diamond necklaces worth less than expected, as the disappointments mounted, many people would have cut their losses. But Skipper never gave up: “I think I’ve gotten much better at seeing the negative and flipping it to a positive,” she explains. “Had someone said that someone was going to trade something that’s worth not even a single penny for a house that’s worth millions of times more, I feel like people would say it’s impossible. But this makes me feel like anything is possible now.”

Remembering her grainy first TikTok video, in which she shakily filmed her hand holding the bobby pin and then her computer screen showing her posting it to Craigslist, because she didn’t understand how the app worked, Skipper says: “It makes no sense. I was not supposed to be the person that did this. But I became that person and now I have an entire house. I don’t think you have to be that person who’s supposed to do it.”

After such a back-breaking challenge, Skipper’s going to do it all over again – and is hoping to donate the next house to someone who needs it.

“I was the second person to do it once. But I want to be the first person to do it twice,” she smiles.