Trade Up Game

“Trade Up” is a game where you try to trade an item for a bigger, better, or more valuable item. You can learn more about the rules, and my modifications on this page.

Current Items for Trade

These are the items I currently have available for trade. I’m not interested in trades + cash, but would consider trading multiple items for a single item.

Why I’m Playing This Game

Recently I’ve decided I want to play a game. I’ve always called the game “Bigger or Better”… but I want to make it bigger, and…. uh… better. But first, a little history.

I first played “bigger or better” when I was in middle school (sometime around the year 2000). I don’t remember exactly which group it was with (I think it was a school group or youth group), but I remember that we started with a penny or a paperclip, and went to the mall to practice our trading skills.

I don’t remember what we ended up with, but it wasn’t anything good. Mostly plastic bags, posters, and free samples. Things a cashier could hand us from behind the counter without getting in trouble. Eventually, I believe security asked us to stop playing the game.

In high school, I planned several “scavenger hunt” birthday parties for myself and my friends. One year we played a similar version of the “bigger or better” game. But this time it wasn’t limited to the mall. We split into teams and drove our cars to neighborhoods or businesses. The goal was to see who could end up with the best item at the end of a few hours.

To judge the winner, we listed the items on eBay, and decided that the highest bid would determine the winner. I remember that the winning “item” was a box of old broken cell phones from a phone repair store we stopped by. I think it sold for around $80 and we split it between 3-4 of us.

Fun times were had by all.

Since then, the game has received some notoriety because of the “red paper clip guy” and several YouTube channels playing the game. There was also a show on A&E called “Barter Kings” where they basically played the game as pawn shop owners.

After watching some of these videos I thought “wow, there is so much to learn from watching people play this game.” Alot to learn about salesmanship, strategy, and how stepping out of your comfort zone can often lead to unexpected results.

Then I thought, “why don’t I play the game again, but change the rules and strategy to take the best part from each of these versions. Take the lessons other people have shared, and build on them even further. Where could that end up?”

Not to mention, I have a few fun ideas to add my own spin and make this interesting. I need a hobby, and this should be something fun I can do alone or with family and friends.

Typical Rules of Bigger or Better

Bigger or Better is common team building or ice breaker game in schools and youth groups. It could also be a fun date night idea, or a way for your family to get to know people in your neighborhood.

The game usually starts by giving each person or team a small item. This could be a penny, a paperclip, or anything else of inconsequential value.

Set a time limit, define the rules (this list is great for inspiration), and come up with your criteria for judging.

Some people like to judge based on the physical size of the final object, and some like to judge based on which item is the most valuable or most unique.

To play the game, try to trade your starting item for anything that is “bigger or better.” Then, repeat the process with your new object, until your time runs out. You could play the game at a mall or shopping center (check with security first), in a neighborhood, or at yard sales or flea markets.

At the end, have a vote on which person or team wins, and let them decide to keep their item, or trade it for the best item from another team.

Notable Examples of Bigger or Better

Not everyone calls the game the same thing. It is often referred to as “bigger or better,” “the paperclip challenge,” “the paperclip experiment,” or “the penny challenge.” However, the basic premise is the same.

Red Paper Clip Guy

Kyle MacDonald might be the most famous story about the “bigger or better” game. He ended up doing a TEDx talk that got over 10.5 million views! He has also been featured on many YT channels, news stations, and more.

Kyle started with one red paperclip and in about a year (and 14 trades), he had traded all the way up to a house!



Chad actually has several videos playing this game, and they have millions of views. He plays the game pretty traditionally and starts with a paperclip in a shopping mall. He scores some pretty cool items.

Ryan Trahan

Ok, technically Ryan doesn’t play the game by the rules here, but he does try to “trade up” from a penny. I really enjoyed this series.

Marcelas Howard

This was a decent example of the game played at a birthday party.

Barter Kings

Barter Kings was a show on A&E for 3 seasons from 2012-2013. You can find episodes online on Hulu.

During the show, they start with a goal (something they’d like to receive as a trade), then they select an item that they have on hand at their pawn shop to start a trading chain.

By the end of the episode, they always end up with their goal. The show has been “exposed” to say that many of the transactions were not realistic, were pre-negotiated before the show, or don’t tell the whole story. There are even stories about casting calls for the show, where people could “apply” to be on TV by offering up their valuable items.

Still, the show is interesting, and I learned several valuable lessons I plan to use in my own trade up experience.

Yale Class

A professor at Yale (Professor Zoë Chance) has a course on Mastering Influence and Persuasion. In that class, the students are assigned to play Bigger and Better. An article about that class shows that one team traded from a paperclip to a car!

My Modifications to the Game

Instead of just playing the game by the normal rules, I thought it would be interesting to make some modifications. These are some variations I’m considering, and I may change it up as I go!

Start with more than one trade

I have quite a few things that I would like to trade. Instead of starting with only one item, I’m going to have multiple trades going at the same time.

Start with larger items

If most people start with a penny or paperclip and end up with items that are significantly larger and more valuable, what would happen if I get a head start with larger items? I have some things I’d like to trade that are already worth several hundred dollars. I’ll start with items in a variety of price ranges.

Improve items to increase value

If I can get an item that needs repair or improvement, I may put in the effort to fix the item to leverage my trade.

Tell a story to increase interest

This is a great way for me to get better at storytelling. Hopefully I can find some interesting ways to tell stories about the items I’m trading, and it will be interesting enough to add value to my trades.

Use my website and YouTube channel

I’ll use my website to track progress, and I’ll also have a consistent place to send people to learn about what I’m doing and what items are available. I hope this could also be a fun YouTube series, so I plan to record some videos of my trades.

Start a trading FB group

I’m not sure about this one yet, but I could start a Facebook group just for playing this game. That way, I could find like minded people who are likely to have interesting things they want to part with. There are already so many buy/sell/trade groups, so I’ll definitely plan to utilize those.

Start a podcast

Again, I haven’t decided on this for sure… but it could be really fun. I’m picturing an episode per item, and letting the person who I’m trading with be a guest on the podcast. I’m going to give this some thought, but I think it could be really interesting.

My Specific Goals

One of my favorite quotes (I heard it from Tim Ferriss) is: “Life punishes the vague wish and rewards the specific ask.”

Instead of just playing this game randomly, I’m going to set some goals for items I’d like to reach with my trading. I’m also setting some goals for lessons I’d like to learn along the way.

Specific Items

Backpacking Gear

This isn’t extremely specific, but I am interested in all kinds of backpacking gear. I need a new backpack, but also need other essentials (stove, lightweight tarp/hammock/quilt, headlamp, trekking pole, etc).


There are some great places to paddle near my house. I’d love to start with something for still water (a fishing Kayak), but if I’m into it, may also be interested in a sport boat.

Mountain Bike

As a young teenager, I rode my mountain bike as often as possible. I’d love to get back into it and want to trade up to a nicer mountain bike. Doesn’t need to be extremely fancy, but I’d love something that is nicer than a typical department store bike.


Four door pickup truck. Would especially like a Toyota Tacoma. Need something that can seat 5 and pull a boat, popup, or trailer. Don’t mind high mileage, but don’t wan’t something that needs lots of work.


I live 5 minutes away from an amazing lake. I would love a boat to go out and explore it more often! I’d be interested in a pontoon or a ski boat that can fit at least 7-10 people.

Pop-up Camper

I’m not 100% sure what kind I want yet, but if I do end up with a truck, I’d also love to consider a popup camper. Would need to sleep at least 5.

Real Estate

I would love to trade into a property that needs some work as a way to get started “flipping” houses. Trading up to a house is a great BHAG for this game!


I know that sometimes people are willing to trade “experiences” for an item or exposure. Who knows what could be possible with this game. I’m always interested in hearing about experiences that are very hard to come by.

Habits, Learning, and Experience

Appreciate Random Items

There are so many things that I hold on to that no longer bring me joy. There is a reason that I’ve kept the item, but in some cases I need to learn to appreciate that item by letting it go.

So many items have unique stories. Those stories are tied to human connection and memories. Learning those stories is a great way to connect with other humans, but also a way to appreciate a newly obtained item even more.

Get Outside my Comfort Zone

I’d like to practice my manual outreach and networking skills. I also want to practice getting uncomfortable. Asking someone to give you something more valuable than you are giving them in return is a great way to get uncomfortable.

Going back to the basics and trying to start the game with only a penny or paperclip, and ONLY asking strangers to trade in person may also be a way to get outside of my comfort zone.


I will need to practice salesmanship if I am going to trade UP in this game. The item I am offering will often be seen as less valuable than the item I am hoping to obtain. I’ll need to learn how to frame my offer carefully, look for strategic ways to add value, and tell an interesting story about my item.

Do Something Fun

I’ve been thinking about doing this for years now, so I figured now is as good a time as ever. It seems like a really fun game/hobby to me, and I think it could be fun to get the kids participating as well. It will also give me a chance to add some content to my YouTube channel, and maybe even start a podcast. The possibilities are endless, but as I’m writing this I haven’t yet made my first trade… so I need to just take action!