8 min 41 sec

Reddit Secret Santa Delivers Sack Full Of Adventure

After creating an unforgettable scavenger hunt for an anonymous Redditor, an account manager stumbles across his own buried treasure.
Adventure Reddit Service Travel

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What It's About

A Reddit Secret Santa unwraps a new career.

Business Model
Skills Required
Travel Planning & Coordination
Profit Potential

Words of Wisdom

Today's story is a perfect example of something I say on the show often—side hustle ideas really are everywhere! When Chris initially did this, he wasn't planning on starting a business around it. But when he saw how successful it was, he took action.

TL;DR - stay on alert for good ideas, and know when to take action!

Fun Fact

Reddit's secret Santa gift exchange is a behemoth of generosity! Since 2009 there’s been nearly 2 million people take part, from over 160 countries with almost 50 million worth of gifts given.

Notes from Chris

Episode 943
A few short years ago, Chris Waters was working as an account manager for a software company. He says he was just an ordinary guy with an ordinary job. Adventure, excitement, and randomness were not at all part of his daily routine.

But, once a year Chris did embrace those three things with great enthusiasm. He did it through the fun of Reddit’s Secret Santa, the world’s largest gift exchange. In December every year, Reddit matches willing users of the site. Each person is provided a few details about their match, so they can arrange a suitable gift based on their interests.

Chris loved it and got into the spirit of it every year. Then, in 2015, he was particularly excited because his match, Blane, lived in the same city as him: Phoenix, Arizona. That meant that Chris could provide a truly unique gift, one that he’d been pondering for some time.

He’d create an elaborate scavenger hunt; one full of clues, codes, and curveballs. Blane, the lucky recipient, would receive a once in a lifetime experience of engaging in an adventure around his own city.

Chris had a lot of fun putting the whole thing together and says he did so without any ambition other than helping Blane have a good time. Little did he know, that the very same scavenger hunt would lead him to a treasure of his own…

To start, he planted clues that sent Blane and his girlfriend to a local cemetery, then the zoo, and then on to several other locations around Phoenix. Each stop featured a clue to the next, with fun activities sprinkled along the way.

The hunt culminated with a stop at a bar where Chris was waiting to present them with a bottle of champagne. Blane and his girlfriend were amazed. They said it was one of the most enjoyable days of their lives.

Chris spent $400 putting the whole thing together, which, in hindsight, was a pretty cheap way to validate a novel business idea…

Since the concept was so well received, he thought he might be able to find a few people willing to pay for their own unique scavenger hunt. So, he registered a domain name and built a very crude website describing the offering.

He called the project Constructed Adventures.

Although his beginnings were humble, Chris is now in the position of being booked out well over six months in advance, and he builds experiences for people all over the world! His adventures have gotten even more professional and elaborate, and his pricing has grown along with it. He only handles one adventure every two weeks, but now he charges several thousand dollars per client.

That means, on top of traveling the world for free, Chris is also well paid. Each month he earns around $5,000 in profit.

Needless to say, he is loving life! He’s gone from an act of gift-giving kindness and turned it into a new career that almost anyone would envy. His biggest adventure of all is the one he’s on right now.



Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,


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Quote of the Day
"You can start a business like this by practicing on the people you know. Start planning unique events and days (surprise parties or proposals) for friends and keep improving.​"
—Chris Waters #SideHustleSchool

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To infinity and beyond,

Chris Guillebeau