Mystery Trip: The Best Adventure You Know Nothing About

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

Asking yourself what's the worst that can happen is often a helpful exercise. It might show you that there's not a lot you have to worry about. If you're thinking of pursuing a big dream project, even a small goal of some kind, what's the worst that can happen? It might not work out. So you go back to doing what you were doing before, or you do something different.

Today's featured story has some thoughts about that. Welcome to Sadduceville School, by the way. My name is Chris Guillebeau. In this story, a childhood summer camp experience leads to a brand new career and a mystery trip out of corporate life. It's all about taking a bus trip to an unknown destination as part of a party or corporate bonding experience.

And the guy running this business has built it to quite a substantial level, as you will hear. Now, working on this story reminds me, we actually did mystery trips, kind of like this, for WDS, the event I produce every summer in Portland. A couple of years, actually. And the first year we did it, we had rave reviews, and everyone loved it, everyone who went on the trip, at least. And naturally, we thought, "Okay, let's scale this up a little bit.

Let's try to do it with more people next year." But the second year we tried it, it didn't go so well. And the group that we worked with didn't have much of a plan, and we basically had to scramble on our end to make it right. So therefore, a business like this is all about customer experience. If people have a great time, they will spread the word. And that's what's happened with this guy's business that you'll hear about in the story.

But if they don't have a great time, the whole thing will fizzle out. It just won't work. Or people will spread the word in a way that you don't want them to. So this is the kind of business to go into if you're really into customer experience, if you like making people happy, if that just brings you joy. Whereas if that's something you don't want to deal with, if you're better at something else, well, then there's another project for you.

So this one is called Mystery Trip, the best adventure you know nothing about. Stay tuned for the story. Attending summer camp is a childhood rite of passage for many kids. The average camper often heads home with no more than a popsicle art project and some extra sand in their shoes. But former executive recruiter Dave Green came away with something a little different.

He turned his summer camp memories of a surprise bus excursion into an experiential event planning company that's on the road to bringing in $500,000 this year. This company creates custom-made excursions for clients looking to plan something unscripted for corporate team builders, bachelorette parties, or family gatherings. The idea started on a not-so-mysterious day long ago. Childhood Dave was at summer camp and boarded a bus with his fellow campers to an unknown destination. The trip ended with a fairly boring conclusion.

He says they went to a show or harbor cruise, but the fun was in sharing a mystery destination with a group of friends. That excited, nervous, and wonderful feeling stuck with him. Years later, as a young adult, Dave was successful in his work, but personally feeling a bit blue. He decided to recreate the concept with an annual gathering of friends, and he had a great time. Then, when he found himself in the midst of a divorce, he returned once more to the idea of mystery trips.

He decided that it was time to take a figurative hop back on the bus, this time as a business venture. He sent out emails to everyone he knew, and within a few weeks got his first gig hosting a friend's 30th birthday. Over the next five years, Dave slowly grew the business, exploring and refining various marketing strategies as he went, and happily doubling profits every year. So, how does it work? Well, to get started, a client contacts Dave with a few ideas and a budget.

Then Dave, or a member of his mysterious HQ team, takes over all the planning. Everyone on the trip signs on to an itinerary known only to Mystery Trip and the group coordinator, allowing the adventure to unfold from there. Trips usually last between four and eight hours and consist of three to four stops. Prices begin at about $175 per person for a 15-person trip. In the past five years, groups from YouTube, Netflix, Lyft, Toms, and Airbnb have all participated in mystery trips.

These trips have led to hand-feeding animals in a wildlife sanctuary, playing basketball in an NBA court, and even recreating the hit "We Are the World," you know, the 1985 single, in the same studio where it was originally recorded. It's all about fun, fantasy, and group bonding. The goal is that having everyone share the same experience creates surprise, delight, and more than a little magic. But what about the money? How did Dave Green grow the green?

He says marketing was key. He began with word of mouth as people started sharing their weekend mystery trip over the water cooler back at work. But he didn't stop there. He also began using Google and Facebook ads and sending cold emails, building and creating targeted lists as he moved Mystery Trip into the world of corporate clients. Analytics were particularly useful in helping him refine the strategy.

They provided feedback as he experimented with memes and aimed to create a tone that would be helpful, a little snarky, but not annoying. The message he worked on conveying to potential clients was more about giving information and less about selling his business concept. Along the way, he's relied on part-time assistance and says that finding the right assistant is invaluable, especially when growing the business from side hustle to main hustle. Solving the mystery of how to run a successful mystery business has meant following some obvious clues. Studying the market, reading exhaustively about corporate excursions, and asking trusted advisors for their honest thoughts.

Like many side hustlers, Dave has also had to learn to focus his energy and avoid trying to be everything to everyone. That's why, after some trial and error, he dropped the idea of creating murder mysteries, figuring that there were already enough venues for that type of business. Another idea of creating mini-mystery trips for two to four people also got dropped along the way. Since 2015, Dave has been able to operate Mystery Trip as his main business. He delights in the triumph of being able to do a job that puts him in touch with excited clients and cool experiences on a daily basis.

That same sense of childlike enthusiasm and wonder that inspired Mystery Trip in the first place is what Dave hopes to inspire other side hustlers to realize. And here's his advice, get ready. Life is way too short to not be happy. That means following a dream because the worst that can happen is you go back to your old job. Well, I know somebody out there needs to hear that advice from today.

Life is too short to not be happy. That means following your dream because the worst that can happen is you go back to your old job. All right, now you may think, "Oh, my old job might not be available." But the same principle is kind of there. The worst that can happen is it doesn't work out, so you do something different, whether it's the same thing you were doing before or something else. I often hear from people that are just on the fence, they're trying to make a decision.

And on the one hand, I want Side Hustle School to be kind of a no-pressure environment. A lot of what we're trying to do here is redefine risk and show that you don't have to quit your job right away and be a "entrepreneur," take a lot of risk, borrow money, et cetera, which is all completely true. But at the same time, if you're listening to this program, one way or another, you probably are a dreamer. If you're not a dreamer of some kind, I don't know why you would like these stories. These stories are all about people taking action on an idea or a dream.

And then sometimes it leads to something that they never even imagined before. So I am pro-dream. I want to encourage people to follow their dreams. And then just on some practical specific notes, Dave mentioned a lot of tools that he uses. He talked about the CRM software he uses, some plugins and all that kind of stuff.

I didn't want to put it in the story because it's kind of detailed, but we're going to include all of that on the show notes page for anybody who wants to do more research for their own planning. So I'm going to leave you with that today. Inspiration is good, but inspiration with action is so much better. Those notes and resources are at www.sidehustleschool.com/1018. Thank you so much for listening today.

Be sure you're subscribed because much more is coming up. My name is Chris Guillebeau. This is Side Hustle School. From the Onward Project.