Ready or Not: My Experience Launching a Side Hustle in 121 Days

The handwritten check arrived in a plain envelope. I signed and deposited it right away. Normally I would have then shredded it. But not this one. I’m saving this one.

It’s from my friend Fred “Honey Pot” Williams, a 61-year-old gastroenterologist and beekeeper, and it’s the first revenue from a side hustle I started with another friend, the first check I’ve gotten since graduating college for producing anything other than words. It feels like the first check of the rest of my life.

That’s certainly an overstatement. But I’m excited to stretch out into something new and for conceiving, planning and executing the first product: an adventure I dreamed up called 50-50-50 in which Honey Pot, eight others and I hiked 50 miles, biked 50 miles and canoed 50 miles, all in one five-day weekend. The 50s were a hook to celebrate my 50th birthday and just happened to form a great marketing shtick for an adventure trip. 

I’ve had a thousand half-baked side hustle ideas; this is the first one I’ve allowed to cook until it was edible. The difference between all those half-baked ideas and this delicious one is simple: passion. I wanted, needed, had to try this one. 

Life’s too short to pursue things you don’t love. If you’ve got that idea—that challenging, exciting, can’t-get-it-out-of-your-head-idea—I urge you to stop thinking about it, stop daydreaming about it, and start doing it

Maybe you can learn from my journey. Here’s how it went.

121 Days to Launch: An idea starts to form.

This side hustle was borne of a cup of coffee. I drank it in the Linville Gorge alongside the Linville River in North Carolina. Although it was “just” an instant cup of coffee, it tasted like a magical elixir. The setting made it taste better—the Linville Gorge is one of my favorite places on Earth. So did the friends with me—Ryan and Andy and I have chased adventure all over the country together.

I have spent much of my adult life pursuing moments like we shared as I drank that coffee. Relationships like that can be formed in any number of ways; it could be over books or wine or musicals. Mine happen to come via adventure with friends. I could tell a dozen other priceless stories like the one about that morning from a dozen other trips with a dozen other friends. 

In the past few years, I’ve organized three 250-mile bike rides, four paddling and/or fishing trips, a half dozen camping trips, and more besides. My life is better, and I humbly submit that my friends’ lives are better, because of the bonds we have formed on those trips. Taken as a whole, they have made us stronger physically, mentally and emotionally. 

On the day I get back from one of those bike rides, I conclude I want to share what I get out of these trips with a larger group of friends. Take that three-person trip to the Linville Gorge that yielded the coffee. What if there had been, say, 10 people there? 

I have enough adventure-minded friends to fill that many spots. But to organize a trip for that many people would take time, which, frankly, I can’t afford to spend. What if I made the trips slightly professional, made all the reservations, cooked/bought the food, etc., and charged a nominal fee for the effort?

The value proposition is simple: The customers get an all-inclusive adventure vacation with their friends. So do I, and I get a little scratch on the side for the time it takes me to organize everything.

I throw the idea at a few friends who have been on the trips with me. They all like it and encourage me to pursue it. I talk to friends in the travel industry. They encourage me, too.

The idea grows from a daydream into a goal. But there it sits, unpursued. I lack the necessary detail-oriented skills to turn it into a reality. I have a long history of coming up with ideas like “let’s celebrate my 50th birthday by hiking 50 miles, biking 50 miles and canoeing 50 miles.” I often convince people to go with me. 

But there’s a big difference between that and having a budget, a packing list and an hour-by-hour breakdown of where we will be in the course of such a trip, all of which I need to make it executable as a side hustle

Because of my inability to manage such finer points, the side hustle seems doomed to die unconsummated.

97 Days to Launch: When passion meets opportunity.

Have you ever had one of those light bulb moments where a solution to a problem pops into your head, and it’s so obvious, you wonder, why didn’t I think of this before? That happens today.

Of those trips I mentioned above, my friend John Urhahn has been with me and helped me plan all but two of them. Broadly speaking, I concocted the ideas and he figured out how to make them happen. 

Of course he should be my partner. I send him a text. He says he has also daydreamed about the same basic idea. A few hours later, we agree to be partners and that our first trip will be 50-50-50. 

We have passion, customers and an idea for a product they will love.

Now comes the hard part: making it happen.

88 Days to Launch: Vision over details.

I wake up at 2:30 a.m. with my brain whirring with ideas and excitement. I barely get back to sleep. The next day, John tells me he had a dream about being on one of our trips and setting up tents in tall prairie grass.

It’s worth noting that none of our excitement focuses on important details such as LLC or corporate structure or insurance. All we talk about is the trips we will plan, and how those trips will change our friends’ lives. Right now, vision is more important than finer points. 

87 Days to Launch: Make room for it.

To find time for this in my schedule, I shed some responsibility. I have wanted to revamp my social media plan for years. Now with 50-50-50 requiring hours of work, I hire Chris Iott, a social media solopreneur who was the best man at my wedding, to manage my accounts for me.

85 Days to Launch: At some point, you just have to go. 

I’ve learned over the years that if I wait until everything is perfect to try something new, I’ll never do it. I apply that now. With three months until the dates we chose for the trip, we are mostly, but not entirely, ready to announce this. John has worked tirelessly to draw up an itinerary; it’s close, but plenty of unknowns remain. We announce it anyway because our customers need lead time for the five-day trip. 

Initial conversation to action took only 12 days. Considering my history of having ideas and not acting on them, I’m proud of that. 

We have modest goals for the first trip. We hope to have eight to 10 paying customers and make enough to pay for both of us to go on the trip. I expect most or all of the customers for the first trip, maybe even the first couple trips, maybe even all the trips, to be friends or friends of friends.

To set the price, we make assumptions about costs. In other words, we guess. Pro tip: It’s not a great idea to set a price for your product before you know how much it costs to make it. It all works out OK, but what we think it will cost changes about 100 times between now and the trip, and it keeps changing until after we return home, when we decide the trip was so great we have to buy T-shirts for everyone to commemorate it.

76 Days to Launch: Your product needs an identity; it will all but certainly evolve.

I went to an Indian restaurant a few years ago and I ordered, apparently, a plate of molten lava. I told an Indian friend I never wanted to eat there again, and he shrugged. He told me he considered that restaurant’s spice level to be mild, at worst. I think of that meal when I hear from potential customers who are intimidated by a trip that features 50 miles of hiking, 50 miles of biking and 50 miles of canoeing. 

My response: It’s supposed to be intimidating. The point of doing this side hustle is the point of the 50-50-50 trip: John and I want customers to wonder if they can do it. We want them to aspire to it. We want fear of failure baked in.

This will likely be true to some degree for all of our trips. But I know already we will wrestle with balance. Neither John nor I want to organize cake-walk adventures. But we don’t want to build trips so hard we have an extremely small customer pool. 

32 Days to Launch: By side hustle, I mean time-consuming hustle.

I graduated from college on a Saturday and started my new job on Monday covering a city council meeting. After it ended, I rushed to my office to work on my story. It took me 3 1/2 hours to write. Three years later, when I covered my final city council meeting, if it took me 3 1/2 hours to write the story, it was because I took a three-hour nap.

I tell this little story as much for me as for you. EVERYTHING in this side hustle takes FOREVER. I have had to remind myself it won’t always be this way. I’ll learn efficiency by doing it, just like I learned to write more efficiently. But right now, every decision weighs 1,000 pounds and takes forever to make. Hotels, Airbnbs, canoes, routes, costs, what to feed them, what to give them to drink—it’s never-ending. 

1 Day to Launch: “If it doesn’t challenge you, it doesn’t change you.”

I first heard that bromide from Julia Dujmovits, a gold-medal winning Austrian snowboarder I profiled for ESPN. I’ve been thinking about it through the last dash to get ready for the trip while still working my regular job. 

We leave tomorrow. Finally. I have been pushed to my limits. It’s only been three months, but it feels much longer. In addition to physically training for the trip, I also sell two stories other than this one about it; cook a pot of spaghetti, three pots of chili and five breakfast casseroles; and make nine combined trips to Costco, grocery stores, 7-Eleven and sporting goods stores. I subcontract brownies to my 15-year-old daughter. I teach her not to negotiate against herself and shell out $20 to her. Meanwhile, John has drawn and redrawn our itinerary, packing list and various other pre-trip details so many times I’ve lost count.

My anxiety about whether we can pull it off and excitement to do so are marbled in a delicious stew. 

7 Days After Launch: Know your why.

I saved this for last on purpose. The adventure ended in the wee hours of the morning two days ago. It was excellent, exhilarating, exhausting. I barely slept before, I barely slept during, and now days later I’m still recovering. 

We learned a ton about what to do and, more importantly, what not to do. I know we got one thing right: We nailed our why

We sold time in a canoe, miles on a bike, hours on a trail, meals cooked on the side of a river, a cold beer after a long day. But those are not the product. They are the means to the product. 

The product we really sold is strong relationships forged through shared transcendent experiences. We provided the foundation to build and strengthen friendships that yield moments like the one Andy, Ryan and I shared over that amazing cup of coffee.

In the days since our adventure ended, the text exchange among the 10 participants has hummed along unabated, with funny notes about our adventure, links to a podcast, a poem a participant wrote, and excited chatter about what our next trip should be.

This article originally appeared in the March/April 2022 Issue of SUCCESS magazine. Photo by Tõnu Tunnel/Stocksy United.

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Matt Crossman is a writer based in St. Louis. He writes about sports, travel, adventure and professional development. Email him at [email protected]

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