Most wouldn’t think twice about the common object; many of us have owned hundreds of similar paperclips throughout the course of our lives. But Kyle MacDonald’s creative mind had other plans for the red paperclip.
A fan of the childhood game, Bigger or Better, Kyle opted to utilize the power of Craigslist in the early digital days to see if someone was willing to trade for one red paperclip. That triggered a domino effect of trades, which eventually landed Kyle with a much bigger and better item: his very own house in Kipling.
Kyle’s inspirational story has led many others to take on their own trading pursuits and, most importantly, widen their perspective on what can be achieved with a bit of creativity.
Best of all? Through this interview, I discovered Kyle (
Kyle - I’m a guy who likes to figure out ways to make things happen.
Kyle - I started out with one red paperclip, and asked people if they wanted to trade me something bigger or better for it. I traded the red paperclip for a pen shaped like a fish. Then I traded that for a doorknob. I kept making trades with people for sequentially bigger and better things until I ended up with a house.
Kyle - Most people were like, “That sounds like something you’d do.”
Kyle - The moment after about five trades when the story went viral and my phone started ringing off the hook with literary agents and so forth.
Kyle - It varied between zero personal interest and total discomfort awkwardness to absolutely the funnest most interesting thing in the world, depending on who specifically wanted to hang out, their reasons for doing so, the weather, our state of drunkenness etc. There was an element of being Truman in the Truman Show to some degree. I absolutely loved our time at the house in Kipling, we met some great friends and had an awesome time. I also like anonymity and large cities though, so it’s a matter of balance and “best of both worlds.”
Kyle - I’ve kept in touch with most people, to some degree. Crashed on couches with many, over the years. One time in 2011 Jody and I and others walked into a store in NYC and bought everything in the store. Check it out at www.storebuyout.com.
Kyle - The story is: it is currently being shopped around and has been under a variety of development deals over the last decade. Pretty much out of my hands. I’d say the odds of a cameo are 77%.
Kyle - It feels great. Anything that can help inspire people to go out and do things and try new stuff out is a huge win.
Kyle - One time I hung out with THE Scumbag Steve and “Dancing Matt” and Judson Laipply and other 00s internet personalities at ROFLCON in Boston. The conference was sort of the “who’s who” of internet memes and projects, up until that point. The biggest change in Internet culture over the last decade is that it’s a far less homogenous culture, of household memes and names. In the last decade things have grown significantly. There are now thousands of vloggers and instagram stars and so forth with millions of fans, that are only really known by their fanbase. It’s great to see things develop, and diversify, and grow. Internet is completely mainstream in 2019. Back in 2005 when I started making trades, the obscurity of the fact that I was using the web to make trades was part of the reason people talked about it. Social media and mobile internet has moved fast!
Kyle - I’ve spoken at hundreds of events and conferences at Fortune 500 companies and Ivy League schools ands whatnot over the years, but arguably the “biggest” and most surreal was when I went back to my elementary school 17 after graduating and spoke to my former Grade 7 teacher Mr. Joseph, and his class.
Kyle - I wore a sash that said MAYOR on it. 'Nuff said.
Kyle - People think that trading a red paperclip for a house was easy and that I want to do it again and specifically I want to do it for them (or their company) again, often for free. I really enjoyed making all the trades back in 2005-2006, but I’ve done pretty much everything else EXCEPT make barter trades, since then.
Kyle - I’m teaching my daughter to ski this winter. That’s the primary objective for the next few months. After that, I’m not so sure. I rarely, if ever, plan things out in advance. I’m much more of an obsessive kind of guy. Once the ball gets rolling on an idea, everything else (within reason) is jettisoned to help make that prime objective possible.
Kyle - Yep I’m on Steemit:
Kyle - Yes I had a fear of public speaking. I overcame it by speaking publicly. It sounds inane, but it works. The vast majority of people who have a fear of something, have that fear because they’ve never done thing thing in question. It’s pretty hard to be afraid of something you do consistently, or want to do consistently.
Kyle - On one hand, my family, for their consistently and trust and positive vision. On the other hand, whatever stupid new thing I get excited about next.
Kyle - Candyman by Aqua. If you haven’t smoked a set of tires in a rental car when the beat drops….you haven’t lived. The rest of the song sucks. But that first beat drop is off the charts. I mean, he’s coming from BOUNTYLAND for crying out loud.
Kyle - I wanted to be a professional ski racer and an entrepreneur.
Kyle - Two of my direct ancestors from 1000 years ago, just to know what they were like, and how they lived, and JFK to ask him if he faked his death.
Kyle - I think sarcasm is poison and camouflaged negativity. Satire is legit, but sarcasm is toxic. It’s nearly impossible to communicate this idea because people think you’re joking or being sarcastic when you say, “sarcasm sucks.” It’s one of those paradoxes, like trying to throw away an old broken trash can, by leaving it on the curb. The garbage guys will come along, see a garbage can, and leave it there. Nobody will throw it away, or think it’s trash. The hardest things in the world are to communicate that you dislike sarcasm, and to throw away an old garbage can. Everything else is easy by comparison.
The One Red Paperclip story is one most Canadians are familiar with. It was an honour to have the chance to feature Kyle in my interview series.
As always, thanks to all of you for taking the time to read.
Who would you like to see me throw 20 questions at? Drop me a comment below and I'll work on setting up the interview.
20 questions with 
20 questions with 
20 questions with 
20 questions with 
20 questions with 
20 questions with 
20 questions with 
20 questions with 
20 questions with 
20 questions with 
20 questions with Janina Storace
20 questions with 
20 questions with 
20 questions with Scott Young
20 questions with Jesse Heiman
20 questions with 
20 questions with Chelsea Dinsmore
20 questions with 
20 questions with Ludvig Sunström
20 questions with Kyle Eschenroeder
20 questions with 
20 questions with Tim Brownson
20 questions with Sean Ogle
20 questions with Henri Junttila
20 questions with Hal Johnson
20 questions with Farnoosh Brock
20 questions with Manny Kess
20 questions with John Goehrke
20 questions with Sunny Lenarduzzi
20 questions with The Cranky Flier - Brett Snyder
20 questions with Shawn Murphy
20 questions with Leo Babauta
20 questions with Jacob Staudenmaier
20 questions with Steve Scott
20 questions with Stefan Hyttfors
20 questions with Zachery Ty Bryan
20 questions with Ryan Lancaster
20 questions with Richard Millington
20 questions with E-mail Prankster
20 questions with Joseph Raczynski
20 questions with Elan Gale
20 questions with 
20 questions with 
20 questions with 
20 questions with 
20 questions with 
20 questions with 
20 questions with Jeff Reitz
20 questions with 
20 questions with 
20 questions with 
20 questions with 
20 questions with Stephanie Ip
20 questions with 
20 more questions with
20 questions with 
20 questions with 
20 questions with David Schiele
20 questions with Marji J. Sherman
20 questions with Shane Barker
