Reddit Secret Santa Delivers Sack Full Of Adventure

This transcript was generated from the episode audio and may contain minor errors.

[Music]

Welcome to a new month and a story that will make you smile. I very much enjoyed working on this one. It is all about a Reddit secret Santa who delivers a sack full of adventure. Every year, the online community Reddit facilitates a global secret Santa program where people exchange gifts with strangers. This program is a behemoth of generosity.

Since 2009, nearly 2 million people from over 160 countries have taken part. Almost $50 million worth of gifts given. And as you'll hear in the story, it's also led to at least one profitable side hustle and then all new career for someone. After creating an unforgettable scavenger hunt for his gift recipient, this account manager stumbles across his own buried treasure. He now earns $5,000 a month putting together epic surprises for people while traveling the world.

Like I said, it's a fun one. Stay tuned for the whole story. [Music]

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 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 and 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 Blaine 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 would create an elaborate scavenger hunt, one full of clues, codes, and curveballs. Blaine, 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 it together and says he did so without any ambition other than helping Blaine have a good time. Little did he know that that very same scavenger hunt would lead him to a treasure of his own.

To start, he planted clues that sent Blaine 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 along the way. The hunt culminated with a stop at a bar where Chris was waiting to present them with a bottle of champagne. Blaine and his girlfriend were amazed. They said it was one of the most enjoyable days of their lives.

Chris had spent $400 putting the whole thing together, which in hindsight maybe was a 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 somewhere willing to pay for their own unique hunt. So he registered a domain name and built a very crude website describing the offer. He called it Constructed Adventures. Soon after, Blaine posted the details of his experience to Reddit, along with a photo album chronicling the day.

The response was off the charts. The post hit the front page and sent a tremendous amount of traffic to Chris's new website, which Blaine had described charitably as being fairly new, so let's give it some time to come together. It was another clue that Chris might be on to something big. He was inundated with requests to manufacture magical moments and spectacular days for people from all over the country. He gained more experience with his initial clients and typically charged around $350 for organizing the surprise.

But there was one big downside. With pricing that low, he made zero money after all was said and done. He had a great time planning the day, but the end result was a treasure map without an X to mark the spot, at least for Chris. In some ways, the money was almost an afterthought to the amount of fun he had. It remained that way over the next year as he built special days for more birthdays, marriage proposals, and other special events.

Eventually though, something had to change. He couldn't continue spending time on a side hustle that wasn't making a profit. $350 per adventure was not going to lead him to the treasure. Since his time was limited, the only way to earn more money was to charge more. So that's what he did, gradually increasing his prices throughout the year.

Right around that time, his fledgling side hustle was featured on an NPR podcast. The episode hit the airwaves and Constructed Adventures blew up. The origin story of the idea, combined with the fun nature of the business itself, was the combination needed to unlock its full potential. By October, 2017, Chris was making enough money to leave his account management job and focus on Constructed Adventures full time. He began receiving so many inquiries that he had to start turning people away.

He developed criteria for finding the perfect clients. They had to be easy to work with, not too worried about budget, and most importantly, the recipient had to be up for a challenge. If they were the kind of person who hated surprises, they were not a good fit. He filtered customers through an initial phone call and brainstorming session. He then go off and build an idea tailored specifically for them.

Then he would circle back with his ideas and collect a deposit to start planning. He sums it up best by saying his ideal client is a creative, communicative person who trusts his abilities as an expert and gives him autonomy to create a magical day. And it seems there's no shortage of people wanting to experience one of Chris's adventures. He's now in a position of being booked out well over six months in advance, building experiences for people all over the world. His adventures have become even more professional and elaborate and his pricing has grown along with it.

He only handles one adventure every two weeks, but now 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. [Music]

Isn't that such a fun story? Chris didn't have the idea of doing this for money. He certainly didn't have the idea of doing it for a career, but his generosity and love of adventure led him to that very treasure. Now I often use that word adventure.

It's one of the three values of WDS, the annual event that I produce, community adventure and service. Those are our three values. And adventure, it doesn't have to be like a helicopter ride followed by bungee jumping into the cliffs of Moore or Niagara Falls. There's all kinds of different ways to have adventures. I think of adventure just as a disruption from your routine.

I think of an adventure as something that is exciting, maybe a little bit scary for you, whatever that can be. So exciting and scary in a kind of nervous way that you're like, oh, that would be totally different and I really want to do that, but that seems crazy. Why would I do that? And I've believed for a long time, if you have an idea in your head that seems kind of crazy, it seems kind of ridiculous, but this idea won't leave you alone. And that's probably a clue.

You know, speaking of clues and scavenger hunts, that's probably a clue of something that you should pursue or at least consider, at least discover, at least explore a bit. And another observation about adventure is once you start going down that road, once you go down the road of adventure, you don't always know where you're gonna end up, which was certainly the case for Chris in this story. So discover what that is for you. Don't be afraid to explore and pursue that path. Inspiration is good, but inspiration with action is better.

Today's show notes, including links to constructed adventures are at sidehustleschool.com/943. Let me know if you end up facilitating an adventure with Chris, that would be a fun story to follow up on. And I will be back again tomorrow. Much more is coming up. Thank you so much for listening.

Here at Rockstar, my name is Chris Guillebeau. This is "Side Hustle School." [Music]

From the Onward Project.