Meet the Entrepreneur Trading a Bobby Pin For a House (and Documenting it all on TikTok)

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We've has featured a lot of amazing entrepreneurs over the years.

We’ve written about people who have discovered new passions, cleared their debt, found a new way of life, and tested themselves in ways they’d never imagined.

But even among all of those stories, we’ve never talked to an entrepreneur quite like Demi Skipper.

Demi sits on the bonnet of the car that was trade 15

While there’s no doubt that San Francisco-based Demi is an ecommerce entrepreneur – and one with some very successful endeavors under her belt – her current project is a little more out-of-the-ordinary.

Bored in quarantine and itching for a new project, Demi is trading her way from a single bobby pin to a house.

And while that might sound insane, she’s on track to reach her goal by the end of 2020.

Meet Demi and Trade Me Project

I first discovered Demi’s project how over 3.8 million others have – scrolling the TikTok For You page. Amongst the usual videos of dances, dogs, and bored teens, the algorithm introduced me to the Trade Me Project.


Trading a Bobby pin to a house #dtp

♬ original sound – Demi Skipper

Each of Demi’s videos lays out her lofty goal: To trade from a tiny bobby pin to an actual house. The rules are simple: No money is allowed to pass hands; everything must be achieved with trades.

Demi’s inspiration came from a similar project taken on by blogger Kyle MacDonald who, over a year, managed to trade his way from a red paperclip to a home in just 14 swaps. With Kyle’s experiment having started 15 years ago, Demi figured that she could replicate his success in 2020 – especially with social media.

By the time I discovered the Trade Me Project, Demi was already several trades deep and off to a flying start. She’d made her way from a bobby pin to an iPhone 11 Pro Max. But as the trades got more valuable, she was encountering more and more challenges.

I needed to hear more about this insanely ambitious project, so I gave Demi a call. During our conversation we discussed her other ecommerce ventures, why this latest project surprised none of her friends, and what she plans to do when she ends up with a house.

A Quarantine Project of Epic Proportions

Demi Skipper appears on TV

Given that she lives in San Francisco, it’s probably not a surprise to hear that Demi works in tech. Working full time for OpenTable, an app that helps users make online restaurant reservations and read reviews, she’s no stranger to the hustle and innovation of startups that dominate the city and surrounding area.

But more than just working for an innovative company, Demi’s always been a side hustler herself. Over the years, she’s had many creative endeavors, including an online enamel pins store, selling almost 100,000 pins over the store’s lifetime. And more recently, following her wedding, she started Tangerine Rentals, a wedding dress rental business.

But with California enforcing a fairly strict lockdown in May, Demi suddenly found herself with more time on her hands. She was working from home, business on her wedding dress rental store was slow due to wedding cancellations, and she was watching a lot of TED Talks and scrolling the internet. Then she rediscovered Kyle MacDonald’s One Red Paperclip project and started thinking.

“It would probably be about 15 years now since he did it, and still, it was resonating with me. I sort of took it as a challenge. I googled, and nobody else had done it since then – no woman had done it for sure – so I was like, ‘This is awesome, I could totally do this.’”

Demi ran the idea by a few friends, and while they all agreed it was crazy, they weren’t surprised it was a project the serial entrepreneur was considering taking on. With her friends wishing her luck, she found the smallest thing she had to hand – a bobby pin – and began her journey.

A Support Crew of 3.8 Million


Wanting to document the wild ride, Demi made a video explaining her goal and threw it up on TikTok. Her videos started exploding, attracting more and more followers, all invested in her story.

“I set up the TikTok account thinking ‘oh I’m just going to track this for myself, this is going to be a really fun project just for me.’ I put the video up just to remember what I was trading, and then within like two or three days, it was over a million [followers], and I was like, ‘This is wild!’ Then it was two million – and then it’s three million.”

As her TikTok account gained followers, Demi was able to trade her bobby pin for a pair of earrings, before swapping those for four margarita glasses. As she found a home for the margarita glasses – swapping them for a vacuum cleaner – it was dawning on her how crazy the whole thing was.

“We met, and she was so happy to get them – and I was so happy for the vacuum. I was like, ‘This is the most ridiculous thing…‘ and she had no idea about Trade Me Project.”

For the first five or six trades, Demi figured her plan was too weird to explain to the people she was trading with. But as the swaps increased in value, she embraced telling potential traders about her bold plan. As it turns out, some of the early traders later found her TikTok videos and were stoked to learn they’d been a part of the project.

As Demi’s trades got bigger and better, more people started following her journey. After swapping a snowboard for an Apple TV 4K, she entered the electronics niche. The swaps had her racing around town at all hours, no easy feat for someone who only travels by bike. Completing her seventh trade – an Xbox One and accessories – was particularly hard work but made her realize she was totally addicted to the project.

“That Xbox specifically was so heavy. And I was on my bike with it just sweating. It was like, this is where this crazy spirit is, where you are literally biking straight up a hill with a giant Xbox in your bag. And you’re fine with it.”


Finding Willing Traders and Encountering Obstacles

As the project continued, Demi’s progress started slowing a little. It made sense; after all, someone probably doesn’t care about swapping items under $100, but after that, it becomes harder.

Despite millions of followers, TikTok’s demographic skews young, and Demi’s found the majority of her trades on Facebook, eBay, and Craigslist. But even on those sites, it takes a lot of asking and persuading to get a willing participant.

“I’ve really gone and reached out to the people who have things for sale already. And a lot of the time they’ll have something for sale for like $1000, and I’ll say, ‘I don’t have money to give you, but I have this.’ And half the time they’re like, ‘You are insane. Why would I take this item you have?’ And then one out of every 5000 people are like, ‘You know what, sure. That sounds great! I do need whatever you have.’”

Trades 8 and 9 - a 2011 macbook and a canon camera set

After her brief foray into the electronics niche, Demi entered the sneaker game, and it was then that she hit her first major challenge: a lost package. Her followers quickly noticed her updates had stopped, and even her mom was asking what had happened. Then, she got incredibly lucky.

“Oh my God! It feels like once you sort of hit a good stride, then of course, a roadblock happens, and there was a point with the mail where I had called probably ten times. I thought it was gone. I was trying to figure out what to do next, how do I spin this story? And it showed up. The [TikTok video] doesn’t show really how much happened, but at a certain point, I was wearing a mask sitting outside of my house in the street for hours, just waiting. And when it did, I think I scared the post guy because he was like, ‘What’s going on?’”


With her hands on the shoes, she learned everything she could about high-value sneakers and ended up in the sneaker niche for a few trades. It wasn’t easy, she joined a bunch of Facebook groups with sneaker enthusiasts, and word quickly got around about her project.

“I would message somebody in sneakers and be like, ‘Hey.’ And they’re like, ‘Oh, we’ve heard about you already. You’re going to try and give us this.’ And I’m like, ‘How do you already know?’ And they’re like, ‘Oh, well, people talk and we’ve heard what you’re doing, especially within San Francisco. A lot of people, they know.’

But after swapping Nike Blazers for Nike Hyperdunks, and swapping those for Air Jordans, Demi was eager to get out of the sneaker game. Thankfully she managed to swap her third pair of shoes for a mint condition iPhone 11 Pro Max. She was now trading items worth over $1000.

Onwards and Upwards

Shortly after the iPhone, Demi secured her next trade, a 2008 Dodge Caravan. The car came from Minnesota, but when it arrived a lot of urgent mechanical attention. And, to add even more pressure, with no parking permit for the car, Demi had just three days to complete the next swap.


Trading a bobby pin for a house. Cross country trade complete! #fyp #trademeproject #tmp

♬ Alone – Petit Biscuit

Things came down to the wire, but she managed to swap the car for a $1400 Boosted Board V3 Plus. Although it might seem like a downgrade, given the car’s mechanical problems, the electronic skateboard was a much better option. Plus, it didn’t require a parking permit, giving Demi more time for her next trade.

With the Boosted Board secured, the next trade stepped back into the electronics niche and an upgrade of an item she’d traded for earlier in her project. This time Demi bagged a 2017 15” MacBook Pro still in the box. This latest MacBook is worth much more than the first one she swapped for, continuing her upward trend.


The Future of Trade Me Project

Sixteen trades into Trade Me Project, Demi she knows it will only get harder from here. When Kyle MacDonald did his project, his trades got more and more strange, including a meet-and-greet with Alice Cooper and a walk-on part in a movie. These experiences were hard to put a dollar amount on, giving him some wiggle room when he traded up. For the moment, Demi’s been able to swap things with a relatively clear dollar value, but she’s not sure what her trades will look like in the future. She’s mostly been surprised at how willing people have been to trade and join her project at all.

“I think the crazy thing is too: More people are willing than you think to make these trades, and the people that are willing to trade are some of the nicest people.”

“You don’t realize what you’re going to get when you’re like, ‘I’m going to trade a bobby pin,’ and even now, some of the friendships and people I’ve met are people I never would have met. Yeah, it’s just been awesome.”

With her trade items quickly gaining value, Demi has no doubt she’ll reach her goal, but she’s not at all fussed about the finer details of where or when that happens.

“I think the question I always get is, ‘Where is the house gonna be?’ And at this point, this has been such an adventure that I don’t really care. I think I’m just going to be excited to get a house and see where it’s going to be. It’s more about the journey of getting there and being able to do it. And just proving that it’s possible. What I do with the house, I think I’ll figure out when I get there.”

She does know she wants to invite everyone who made the Trade Me Project possible to the house for a celebratory party.

“The whole goal is to have every single person I’ve traded with – along with like handfuls of others – once quarantine is over, to be at the house, which I think would be the cherry on the top. The girl who has the bobby pin, I’ve asked her to keep it in a safe place and keep it to the side, so that when we do get the house, we can have the bobby pin there too.”

Demi’s Trade Me Project Progress so Far

All Demi

0. One bobby pin – value: $0.01
1. A new pair of earrings – value: $10
2. A set of four margarita glasses – value: $24
3. Bissell vacuum cleaner – value: $60
4. Snowboard with bindings – value: $90
5. Apple TV 4K – value: $180
6. Bose noise-cancelling headphones – value: $220
7. Xbox One, two games, two controllers, a Kinect sensor bar – Value: $320
8. 2011 MacBook Pro – value: $400
9. 2016 Canon T6 camera set – value: $550
10. Off White Nike Blazers (size 9 men’s) – value: $750
11. Off White Nike Hyperdunks – value: ???
12. Air Jordan 1 Reverse Shattered Backboards – value: ???
13. iPhone 11 Pro Max – value: $1095
14. 2008 Dodge Caravan – value: ???
15. Boosted Board V3 Plus – value: $1400
16. 2017 MacBook Pro 15” – value: ???

An Unexpected Bonus

As she’s progressed, Demi’s found lots of other young entrepreneurs attempting their own versions of Trade Me Project. Being an entrepreneur can be a lonely path, so seeing the project inspiring others has been incredibly rewarding.

“I’ve seen Trade Me Project Berlin, Trade Me Project Belgium, Trade Me Project India. And it’s pretty cool to be able to see almost a worldwide phenomenon happening, of people being like, ‘Oh, like a house seems really crazy. But I have this small thing, and maybe I could get there.’ It’s cool to see other people really trying. And even if it’s like they’re not going for a house, they’re going for an Xbox, or they’re going for whatever. It’s amazing to have people realize that it is totally possible.’”

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