In 2006, Canadian blogger Kyle MacDonald set off on a rather bizarre bartering journey ‒ to trade a red paper clip in for a house. It took him one year and 14 trades, but he eventually got there.

14 years on, his story continues to inspire. In this episode of Start Yours, we speak to Demi Skipper, who's on a journey to explore the same idea. Her version is, however, slightly different.

Aside from the fact that it's a woman who's doing this and she's starting off with a bobby pin instead of a paper clip, Demi also adds a modern twist to her bartering with the use of social media.

This is the story of Demi's trading quest and some of the crazy exchanges she's encountered in her journey to trade her way up to a house.

Her story has also been featured on the Oberlo blog so don't forget to hop on over to give it a read.

Prefer a summary? Here's a seven-point TL;DR version:

  1. Demi Skipper has always been a side hustler. The idea to trade a bobby pin for a house started while she was under quarantine when she came across Kyle MacDonald's story.
  2. To date, Demi has done 16 trades, including margarita glasses, a camera, collectible sneakers, an iPhone, and a car.
  3. When Demi feels like she's not making enough progress, she looks back on past trades and gets surprised at how far she's come.
  4. For Demi, it's less about the house and more about the journey of getting there and proving that it's possible.
  5. Her initiative has inspired similar projects around the world including in Europe and Asia.
  6. She's making full use of the internet and social media to connect to people who'd be interested in a trade.
  7. Her bobby pin journey has led her to build new friendships with people she would otherwise never have met.

Start Yours is a podcast about ecommerce, dropshipping, and all things launching a business.

Join us as we meet entrepreneurs who have gone through the triumphs and headaches of running an online store, and learn how they managed to survive and thrive.

From Paper Clip to Bobby Pin

Demi Skipper on her bobby pin adventures

Allanah: Well, I would love to hear how you got started with this. Maybe you could tell me how you came up with the idea? 

Demi: Personally, I've always been a side hustler. I actually use Shopify for a company called "Hipster Pins" that I started, which was enamel pins that said like, "The Future is Female." And I sold almost 100,000 pins through Shopify. 

That was wild and that sort of took off on its own. So even then, with Instagram, I had 20,000 followers there and I was like, "Oh, this is huge, this is so great." And now looking back, I'm like, "That's nothing."

And then now, I also presently run something called "Tangerine Rentals" through Shopify. It's a wedding rental company, where I send out wedding dresses every single weekend. I just got off the phone with a bride and was like, "I hope your wedding is great. It's gonna be so much fun. I just sent your dress, it's coming tomorrow." 

I think none of my friends were surprised when this happened because they're like, "This girl just never stops and is always coming up with weird things." Even my co-workers who've seen me on the news or on TMZ are like, "This is just typical. This is just not anything out of the ordinary."

With the bobby pins, the whole idea started because of quarantine. You're sitting there, you're not really doing that much. I was on YouTube looking at TED Talks and I came across Kyle MacDonald. 

This is the guy who traded the red paper clip for a house and it's been about 15 years now since he did it and still it was resonating with me. I was like, "This is amazing. The fact that he was able to do this."

And I sort of took it as a challenge and was like, "If he could do this 15 years ago..."

And I Googled and nobody else had done it since then and no women had done it for sure. So I was like, "This is awesome. I can totally do this." And I ran it by a few friends and they're like, "This is really wild, good luck. You would be the person crazy enough to do this."

In the beginning the conversation was, "Okay well, if you get this house...", then it was like, "When you get this house...", and now it’s like "Hooray, now we think you're actually on to something."

I think at the beginning, I was a little bit apprehensive and trying to figure out how far I could even get, especially starting with a bobby pin. And now as the trades are getting bigger and bigger, there is this feeling of, "I'm definitely not gonna stop now. There's just no way." I feel like all it takes is a little bit of determination and a lot of time and... Yeah, it really is just wild to see every trade, I'm surprised.

Allanah: Looking at the 2005 or '06 project, the original project, the more trades that he did, the more insane the swaps got. There was a walk-on... I think the ultimate one before the house was a walk-on part in a movie and the one before that was a meet and greet with KISS or something.

So do you expect them to kind of get to that level or do you think you'll sort of be a little bit more grounded? 

Demi: I really don't know. That's the thing. Every time I'm like, "I'm not gonna get into this," and then I find myself in it and I'm like, "Okay, this is where I'm at now. This is the new normal." What's interesting is I haven't talked to Kyle specifically but I did do an interview where they interviewed me and then they were able to interview him. 

So he gave me some advice even though I didn't talk to him directly and he was actually mentioning that he was trying to go for these crazy things because they didn't have a dollar value on them. So he thought maybe it would be faster if somebody couldn't be like, "Oh, that's only worth X amount of money," because there wasn't a value, which I thought is really interesting.

'Cause right now, everybody is really looking at every single thing and taking value and deciding for themselves. And it's funny because I think every time I'm like, "I don't know how I would possibly get..." I think in the beginning I was like, "There's no way I can get an iPhone." And so right now in my head, I'm like, "There's no way I can get a KISS meet and greet."

But anything is possible at this point, I think. I surprise myself.

Every couple of weeks, I have to look back when I'm frustrated or feel like I'm not making progress and be like, "Okay, last week I had a vacuum."

Allanah: A vacuum that you had to do maintenance on as well.

Demi: Yeah, I got it, and it looked like it had been hit against the wall a few times. There was white paint all over it and I was like, "Oh no. This person." But then it came off, I put nail polish remover on it and it came right off. I was like, "Alright, nail polish remover for everything at this point."

Going from bobby pin to house

Channeling That Entrepreneurial Spirit

Allanah: That's an entrepreneurial spirit I think as well. And so it's interesting to know that you have that background and working also with an app, that's also perhaps the least traditional career, and then you have all these side hustles. 

It does seem like this is the next thing that's like, "What is something a little bit stranger I could do?"

Demi: I know, I know. It's just so funny because people that know me are like, "This does not surprise me at all. You could convince somebody to take something off your hands that they don't need at all," which has just been so funny. 

I've watched people say, "Okay, I'm not gonna trade." And then 24 hours later, I end up trading with them. And they're like, "Okay, yeah, I actually do want it," after I've sold it to them, it's like, "But it's this and it's really good quality."

I was joking yesterday that I feel like a used car salesman, I'm like, "Here's this used item I have," and manage to get something else. And I think what's also funny is with the sneakers, they were men's size 10, very large shoes. And people weren't seeing my face when I was on Facebook or on any of these groups. 

They were just seeing the pictures of the trades and then I walk up and they're like, "Were you wearing these?" "No, it's part of the project. These are not mine. I don't own men's nine or ten shoes." I think that's funny too, the surprise when people see you in real life.

Allanah: Absolutely. And what I also love is that you're just pedaling around town doing this as well. Biking up at 10 o'clock at night to make the trade.

Demi: Oh my God. It's so funny because I get a lot of questions about why I'm always on my bike. But I don't have a car. I haven't driven a car in years, so my bike is the way I get around. It has been crazy. When you look at San Francisco, it's also very hilly. Before a trade, I'll look at the map, and I'll be like, "Oh no!" This is where I'm going, it's straight-up somewhere, and I'm like, "Alright, is it worth it for this Xbox?" 

I carried that. That Xbox specifically was so heavy. And I was on my bike with it, just sweating. I was thinking, "This is what I've done." 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. 

And yeah, it has taken me to some crazy corners of the world, at 10 at night, obviously trying to be as careful as possible and bringing my husband with me. So people are always commenting, but he's recording at all times. No farther away from me than a couple of feet. It just doesn't ever end.

Allanah: That's how you know you're hungry for it, you're pedaling up the hill with this brick and controllers in your bag.

Demi: Yeah, honestly. And then it just turns into a good story. 'Cause I'm like, "Okay, yeah, remember when I was doing that and now I have an iPhone,” which is so much better and so much smaller and doesn't require me to carry something heavy.

It’s the Journey From a Bobby Pin That Counts

Allanah: So you live in San Francisco as well, which is known for extremely high rent and property prices. So were those part of the reason that this appealed to you too? 

Demi: Totally, totally. To so many people, a house in San Francisco feels like the most ridiculous thing possible to wanna get because it's so out of reach. It doesn’t even enter people's minds that they could have a house here because it's just so expensive. 

When I was thinking about what is the smallest thing I have and I found the bobby pin in my house, I was like, "Okay, I think this is probably the cheapest thing I own." And then I was looking around like, "Okay, what's the hardest thing I could possibly do?" And it was like, "Okay, a house, it makes sense." 

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'm just gonna be excited to get a house and see where it's gonna be. 

And I've told some people, if it ends up being somewhere super rural or somewhere where I can't work my job, obviously I wanna think about it because this is just a crazy thing.

But also, I'm considering what it looks like to donate it to somebody who's a follower that needs a house or has a family. I think that's also an option. 

It's really less about what the house looks like or where it ends up being and 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, and we'll see what happens.

The journey from a bobby pin with Demi Skipper

Allanah: But it's just the dream of having a property like that and the way that you hustled a very non-traditional way to get it.

Demi: Totally.

Allanah: It's a fantastic journey.

Inspiring Similar Projects

Demi: Oh my God, so crazy. The other thing too that really has been eye-opening is just... You make all these side hustles and you work on all these things and then you make one thing and it resonates so much with so many people that you're like, "Wow, another person is seeing themselves in me." 

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, a house seems really crazy, but I have this small thing, like a bobby pin, and maybe I could get there." And 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 and just putting in the hustle and the time and watching other people's journeys. And I've gone in and commented on several people and they were like, "Oh my God!" But yeah, it's pretty cool to see that too.

Allanah: Absolutely. I think it's really cool just to see what people come up with, like you said, to go from something tiny to something big. Also, I've been following Project Sim...

Demi: Oh, yeah.

Allanah: With his like $3,000 pillow that he's stuck with.

Demi: Yeah, actually, it's so funny. So that he actually just reached out to me on Instagram this morning to see if I would trade. But I just don't know if I want a $3,000 pillow on my hands.

Allanah: You've already watched someone else hold on to this pillow for so long now, so...

Demi: I know. Every time, every time. When he messaged me I went through all of his stuff, and I'm like, "Oh my gosh, it's gotta be tough." It's just gotta be tough to be stuck. Because I felt like I was stuck at points, and granted, it was only a few days, and I'm like, "Oh my God, I'm stuck. I've been stuck for two days." 

It's fine, but yeah, I think it just shows you how tough it is. It really is tough and it's really like a thousand no's and a thousand, "What's wrong with you?" until you get one person that might be a little bit into it.

Allanah: Yeah. Which is like business and especially ecommerce in general, right? A lot of it is just sticking with it.

Demi: Oh, 1,000 percent. I think there are so many lessons to be learned from just trading all of this stuff, about making it happen and not taking no. And there are so many other things that aren't just about the trades that I think that you don't realize you're gonna get when you are like, "I'm gonna 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.

Demi Skipper on ecommerce and motivation

Going Viral on TikTok

Allanah: Totally, well, it's been great to follow because on TikTok, really you can go viral in what, 30 seconds, and you put it up there and the next minute, you have a million hits or something.

Demi: Yeah, it honestly was. I set up the TikTok account thinking, "Oh, I'm just gonna track this for myself, this is gonna be a really fun project just for me." I put the video up just to remember what I was trading and then within two or three days, it was over a million views and I was like, "This is wild." 

And then it was like 2 million, and then it's 3 million. And I'm like, "Oh my God," now I'm almost at three and a half million. This is just insanity that it keeps on growing, and yeah, it's just wild.

Allanah: That is crazy and then the views are something else in themselves aside from the followers, so the numbers are just, I don't know, they're astronomical, and it's like a snowball that just keeps collecting and then really it's become an avalanche of views.

Demi: It's so weird, one video I was looking at has 28 million or something, and I'm like, "What does that even… That number doesn't even make any sense to me.

I'm like, "How many people is that, how many states is that?" It's just wild and it keeps going up. 

I think you're right, people will watch the whole journey if they just joined, then they'll go through and watch every single video. Even the ones that are really old now, really old, like a month old are still getting more views. It's just never-ending.

Allanah: That's exactly what I did. I was like what... I think maybe the one that I saw was the snowboard… Was it the snowboard one? And then of course you had four or so videos before that, so I was like, "What else, what did she start?"

Demi: Yeah, crazy.

Allanah: As you said, to see so many international versions as well. The red paperclip story is something that I knew and I was always like, "That's so cool, how did he do it?" But I just never thought to start it myself.

Demi: Exactly, yeah.

Meeting Nice People Along the Way

Allanah: Yeah, people have got nothing but time at the moment, in quarantine, and a lot of people have lost jobs or school is on hold, so...

Demi: I know, that's what I keep saying. Every time I get a bunch of random emails being like, "Oh, I just lost my job or I don't know how I'm gonna do this or whatever," and I'm like, "Go for it. Try it. What do you have to lose? We have time." 

And I think the crazy thing too is that 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. All of my friends have been very worried about safety and are these people nice and real, and every person I've traded with has been the nicest person, and really excited to make the trade. So I think that adds to the excitement when the other person is very excited, very nice and normal.

Allanah: Totally. I think that's the thing with ecommerce, in general, if you're giving people something, they're giving you something in return, so ultimately everyone wins.

Demi: Yeah.

Allanah: So a bobby pin turned into a really good thing. It's so nice, it sort of restores your faith in humanity a little bit which is really...

Demi: Totally. I was like, "This is either gonna go really poorly and I'm gonna get scammed," especially with the sneakers. I was like, "I am obviously doing a ton of research, but I'm also putting like a fair amount of trust in somebody that they're gonna ship the right thing, they're not gonna ship me like a box full of bricks or they're not gonna give me fake sneakers." 

And obviously, I do everything I can to take photos and get it double-checked by people that know what they're doing. But there's always that worry.

And when it works out, I think it's such a good feeling.

You're like, "Okay, it is a really nice person." The person I traded the first sneakers with could not have been nicer. The two boys of the second one, they're probably, I don't know, 18 and they were like, "Can we take a picture with you?" after it was all over and I was like, "This is awesome, this is crazy." Cool.

Demi Skipper on how to trade a bobby pin for things

Taking It One Step at a Time

Allanah: Yeah, they're just happy to be a part of it as well. That's so good. So how long do you think that it's gonna take? Do you have any sort of timeline or you're just sorta cruising? 

Demi: So what's interesting is it took Kyle a full year with the red paper clip. I didn't realize just how long it took when I watched it the first time because in the video it seems really quick. His took a whole year. So I am what, a month and a half in... A little bit more than a month and a half. 

Things are moving, so I'm giving it a few more months, and I think I'm just gonna do every month or so, just do a look back and see how far it's taking me and then I think I'll have a better idea. I'm hoping I can do it in like six months. I was telling somebody, "Kyle's took a year, but also it was 15 years ago."

So I'm lucky that there is so much on the internet and there's so much like TikTok and things like that, that hopefully can connect me to people that would be interested. 

Whereas Kyle, he was joking in the interview that he was calling people on his phone, just looking up phone numbers and calling them.

Allanah: Oh my goodness.

Demi: Yeah. So we'll see. I mean it's tough. I have a feeling that once they get bigger, they're actually gonna get harder because it's just hard to have somebody wanna trade for something that's $5,000 or $10,000. Most of those items people have, they're things that they actually want. 

So I have had people, they are really interested in something I have, so they will go out and actually go buy something to trade with me.

Allanah: Oh wow.

Demi: Yeah. So the number one rule is, "I can't use any cash, I can't trade. But how do you go get your items..." They'll go to their friends and say, like, "Hey, I really want these shoes and this girl said she would take these 10 things, does anybody have that?" And they'll go find other people for me. So it's like this line of tradings happening.

Allanah: Which like a whole other chain of people hustling to get that and... 

Demi: I know, I thought about actually getting that person to then go record themselves and how they got their items and then give me my item but I haven't done it yet.

 

Advocating for Women in Business

Allanah: Wow. And you were saying as well that you're the only woman who has done this. And looking at your other businesses as well, they're very skewed towards women as well. Are you a big advocate for women in business and ecommerce and you're hoping to really add this to your story? 

Demi: Yeah totally. So I actually started my career off at Apple, so I worked at Apple on the iPhone, in the Maps Department for four years when I was out of school. And I was on a team of 60 men. At Apple, obviously, they wanna tell you that there are so many women at Apple and there are, but I joked at points, I would have the women's bathroom just as my own personal bathroom. 

I would have ten stalls to myself, I'm like, "Oh, this is lovely, I could just leave all of my items in here." And I think it shows you just how much of a disparity there is with women in tech or women in business. That to me was really eye-opening out of college because in college you're surrounded by people that are women, men, whoever, and going into Apple, I was like, "Wow, this is really a thing."

And I think now it's more of, everything is a challenge. So my head is constantly like, "Alright, what can I do next?" So with the enamel pins, after the election, I was like, "I gotta go do something. Okay, I'm gonna go make pins." And it blew up. And then after I got married, I was like, "Wow, I don't need my wedding dress anymore. What did I buy this for? I spent so much money, I would love to rent it." So I went out and bought more dresses. Now I have a closet in my home full of wedding dresses that I'm sending to other brides.

So it's always like, "Is there something missing that somebody else hasn't done and how do I go make that happen?"

And it's always just the challenge of like, if somebody hasn't done it then I can probably go do it. So that... Yeah, like the Kyle thing, it was like, "Okay, no woman's done it and nobody's done it in 15 years. So let's do it, let's see what happens."

‘If somebody hasn’t done it then I can probably go do it’ by Demi Skipper

Allanah: Yeah, absolutely, you see a lot of opportunity in some... I don't know, out of things that maybe are a little bit bleak, say the election, or after your wedding, that's an expensive thing, what can you do now with that dress you don't use? 

Demi: I joke it's like a sickness. Most people don't see the things that are missing and trying to fill them in and I feel like I have a running list of 40 different things that I've tried. And I think that's the other thing. It's like, yeah, you see the things that work for people. You don't see the things that don't work as complete failures, it’s not the worst idea you've ever had in your life and then you have to go back and figure out why that was a bad idea.

 

Battling Haters

Allanah: With your ideas, do you collect them all? Do you actually make physical notes and plans like that? 

Demi: Yeah, so I have a notes section on my phone. And every time I have an idea, I'll spend a month or so on it and I can typically tell, "Okay, this has no traction. Everyone thinks this is a terrible idea." Even with the rental company, it's really funny because on Facebook, I'll reach out to groups of people and say, "What do you think about this? This is my idea, this is my website." 

And I had, probably like six months ago, a group of people just say they thought it was a scam, there's no way you can rent wedding dresses and... I mean, I was in tears, and it was all women and I was like, "This is so bad that there are so many women that can trash other women." And my husband was like, "You know what, they think you're crazy, and you gotta take it as fuel."

And it's so funny because last night, I posted the TikTok video in the same group of women and I'm getting all of these amazing comments. And then somebody at the end was like, "Wait a second, were you also Tangerine Rentals, the wedding company?" And I'm like, "Yup." And just did a thumbs up and there were all these shocked faces. 

And I'm like, it's such a good feeling to feel like the people that thought you were a scam and couldn't possibly do it, and now they're turning around being like, "Oh my gosh," like, "Who is this person and why is she doing wedding dresses and also trading a bobby pin for a house, also has a full-time job and..."

Yeah, you just have to take it as fuel and don't let the haters get you down.

Allanah: Yeah, absolutely, I think that's great advice. That's literally like the Pretty Woman moment, right? Like, big mistake. Huge.

Demi: Yeah, It's so true. And especially with women, it's so hard because I feel like sometimes it just gets so bad and you're like, "We need to be sticking together. We should be figuring this out altogether," instead of, "Maybe it works but..." That's the internet too, there's always gonna be the good and the bad and you have to take it for what it is.

Demi Skipper on resilience in ecommerce

Allanah: Yeah. And I think often as well maybe if someone doesn't have that mindset, the hustler sort of entrepreneurial mindset, whatever you would like to call it, then maybe the idea, when it's presented seems kinda like, "Ugh, crazy." 

But then if they were in a different situation and they had a best friend getting married and the best friend was like, "Oh, I don't really wanna spend that much money but I would like a nice dress," they would see the idea as a whole different solution.

Demi: Totally, totally, yeah. I think just being in the situation, you realize it does make sense. But of course, a random person on a Facebook group that's just throwing out random ideas left and right, you're probably like, "Who is this woman and when will she stop?"

Allanah: But I think that's a great way of testing your ideas as well, is just to throw it out there into a group. I've never really heard of people doing that with business ideas. With websites maybe, like Rate My Website but just to say, "What do you think about this idea?" That's ballsy and a really good idea.

Demi: Yeah. Thanks, it's crazy. It really is. I have surveys that I've done from years ago that I joke, I'm like, "This was the worst idea and people rated it a good idea." And I'll get 2,500 people replying with results and it's just funny to look back. 

Even before, when I thought 20,000 people on Instagram was huge and now I'm looking at 3.5 million and I'm like, "What is this even? How do you even connect with 3.5 million people? How does that even work?"

Allanah: Yeah, that's crazy but you're doing it. I'm wary of taking up your day but it has been so lovely to speak to you about this whole thing.

Demi: That's so fun to just talk to random people. When you reached out, I was like, "Oh this is so random, and sure, we'll do it." I think the world is so small and there's always something I can help somebody with or a connection I can make that someday you may end up in San Francisco and whatever and you'll remember this conversation. The world is small. The world's so small.

Allanah: Thank you so much, Demi.

Demi: Yeah, it was so nice to meet you.

Allanah: Lovely to meet you and I'll be watching. So I'm happy to see where it goes next.

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