Remember the Red Paperclip Guy from a few years ago? In 2005, an out-of-work Kyle MacDonald started with a single red paperclip and traded his way up to a house in Kipling, Saskatchewan.

Remarkably, this barter adventure took only 14 trades and was completed in less than a year. Kyle started out small, each time seeking something “bigger and better” in exchange.

For example, his first trade was the red paperclip for a pen shaped like a fish. Then he traded the fish pen for a doorknob, and on and on up the ladder.

The story certainly has some feel-good elements to it, and after a while the media attention definitely helped speed the process along, but I think it’s worthwhile to revisit because we’re all trying to “trade up.”

By “trading up”, it’s important to note I’m not necessarily talking about acquiring a bigger house or a better car, but more along the lines of making bigger impacts and living better stories.

I was reminded of the red paperclip story by last week's episode with Rob "The Flea Market Flipper" Stephenson. He talked about a challenge inside his community to start with something small and keep flipping the profits into bigger deals to see how much you could trade up over the course of a year.

I think we all have a red paperclip story. Like Kyle, even starting with almost nothing, you can make big things happen with a little initiative and a little help from others along the way.

This episode is about connecting the events that got you to where you are today, and thinking about where you want to go tomorrow.

What’s the next trade you’d like to make?

In the spirit of the red paperclip story, I’m going to use my own entrepreneurial journey to illustrate this; and similar to Kyle, I’ll use a series of 14 key decisions or trade points. But unlike Kyle, this took me a lot longer than a year!

Full Show Notes: Trading Up: From $8.65 an Hour to Retired at 25, Plus the Next 10 Years

299: Trading Up: From $8.65 an Hour to Retired at 25, Plus the Next 10 Years 33:53 Share

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299: Trading Up: From $8.65 an Hour to Retired at 25, Plus the Next 10 Years