Bring People Together
Have a knack for producing events or experiences? Use the power of community to connect people while getting paid.
Academic Adviser Creates Profitable Karaoke League
Urban Hiker Climbs to Steep Success
Hungover Accountant Starts “Morning After” Party Cleanup Service
Foodie PR Manager Blogs for Free Stuff and Real Money
Busy Professional Clips into Biking Wine Tours
Florida Man Leads Scooter Tours After Watching Rap Video
ACADEMIC ADVISER CREATES PROFITABLE KARAOKE LEAGUE
NAME
LOCATION
WASHINGTON, DC
STARTUP COSTS
$20,000
INCOME
$45,000/YEAR
WEBSITE
A Washington, DC, man uses his entrepreneurial skills and vocal chords to turn a profit while cultivating a community.
About five years ago, Jesse Rauch was living in Washington, DC, and working as an academic adviser. In his free time, he competed in a weekly kickball league, where he says he had a “eureka” moment.
It happened while he was out one night after a game, having a few drinks at a karaoke bar. As he was sipping vodka and belting out “Sweet Caroline,” he suddenly had an idea: Why not take the design of a social, competitive league, and apply it to karaoke?
He shared his epiphany with a friend and ruminated on it a bit in between songs. But he says it only sank in that the idea had potential when he woke up the next day—less influenced by the vodka—and still thought it was a good idea.
In his day job at a local community college, Jesse says that even though his students challenged him, he hadn’t felt he was flexing his creative muscles. He wanted to make something of his own. And what could be more fun than competitive sing-alongs?
Jesse set to work on launching District Karaoke. Its design was similar to a sports setup, where teams of up to eight people would sign up to compete against each other in one-on-one and group karaoke matchups. Then everyone in the bar, regardless of whether they were involved in the singing or not, could vote on the winners using a web-based app.
When he opened registration, Jesse was able to fill all forty-eight available spots for the league in just six days. He officially kicked off the business the following month, using his thirtieth birthday as motivation. In addition to his friends, his new customers came to the party, which helped build early momentum.
District Karaoke now runs three ten-week “seasons” every year, including playoffs and finals, with each division made up of six teams. They consistently fill almost all available spots, which have grown to two hundred per season.
Jesse’s initial startup costs were low, as he used outside karaoke DJs that were paid for by the bars. But he soon realized he wanted a bit more control over the league in order to grow it. He invested about $20,000 to license the music, purchase equipment, and build the voting technology. The investment quickly paid off, since the business has been profitable since the first season.
In an average year, District Karaoke brings in $90,000 in revenue and makes about $45,000 in profit. The business makes this money from individual registration fees, payments from the host bars, and sponsorships.
To get the word out, Jesse relies on the performers themselves as his salespeople. Through their efforts, District Karaoke was able to expand from one to four nights per week.
To save money, he avoided developing a native app for phones—which is not only pricey and time consuming but also requires agreements with the Apple Store and Android Market—and instead built a simple, web-based voting site that would work on all smartphones.
However, while he did save money, he had to make up for it with his time. At the outset, Jesse poured thirty to forty hours each week into District Karaoke, all on top of his day job. He was young and motivated, and wanted to build on his idea. Now, after bringing people on to manage daily operations, he only has to devote ten hours or less each week.
In addition to part-time staff, Jesse engaged league members to help on a volunteer basis through a community board. His goal in recruiting helpers wasn’t just to lighten his load. Instead, it was part of the ethos behind his vision. He wanted members to feel more invested in the league and to build a strong sense of community.
His hypothesis was that people are always looking for other people who share their interests, as a way to find friends and build professional networks. And if someone can creatively do this connecting and curate a positive experience, people will pay for it. This sense of community also has the benefit of keeping people engaged and returning, thereby ensuring a loyal customer base.
District Karaoke has now expanded to Baltimore, Chicago, New York City, and Los Angeles. Its members have sung exactly 10,236 songs, with the 50 most popular songs sung more than 1,200 times in competitions…including popular favorites “I Will Survive” and “Don’t Stop Believing.”
For Jesse, this side hustle has produced several positive changes. He’s been able to switch day jobs, a move he credits to the new skills he gained through running District Karaoke. He’s been able to save money for vacations. Best of all, he’s been able to find true love. That’s right: this side hustle came with some major secondary benefits!
One night while hosting a District Karaoke happy hour, Jesse says he looked to his right and saw the most beautiful woman in the world. They talked, danced, and sang, and he tried his best to impress her. They’re now engaged to be married—and naturally, they even have a special karaoke song.
“In a community-building enterprise, involve more people earlier. My community members are my best salespeople. They know what needs to be fixed or changed, and what needs to stay the same.” —Jesse
FUN FACT The friendly competition of Jesse’s karaoke league can inspire some notable performances. One night, a performer pole-danced on an elected official who was serving as a judge at the City-Wide Finals. Another night, a performer sang a song by Sia in the style of the Swedish chef from the Muppets, staying in character the entire song.
CRITICAL FACTOR
No one had ever started a competitive karaoke league before—and with its abundance of twenty-something working professionals, Washington, DC, was the perfect place to begin. It also helped that Jesse was a natural connector, enthusiastic about working with volunteers and helping competitors have a good time.
URBAN HIKER CLIMBS TO STEEP SUCCESS
A project manager turns a passion for her city into a substantial side income, while getting plenty of exercise along the way.
San Francisco–based Alexandra Kenin has a flexible job as a project manager and editor for a fully remote company. It’s a dream gig in the sense that she’s able to set her own schedule—allowing her to go back and forth from focusing on those job responsibilities to building something for herself.
The company is in the tech industry, but Alexandra’s side hustle is completely different. It’s all about getting outdoors, showing city-dwellers and tourists a lesser-visited part of the city that includes scenic hills and hiking trails.
She calls it Urban Hiker SF, and Alexandra caters to small groups as well as private and corporate events. Thanks to that flexible schedule, she’s able to offer the tours any day of the week, even in the middle of the day. She also coordinates with Match.com to offer special dating hikes.
To get the word out about her new business, Alexandra made a five-step plan:
1. Reach out to companies like Airbnb to see if she could offer tours to their guests (they said yes!).
2. Meet with other tour providers to see how they got their businesses started.
3. Offer free and discounted tours so that she could attract customers and get reviews.
4. Reach out to her network to see if people worked at companies that wanted to do team-building activities.
5. Join her local visitors bureau to meet other people in the industry.
Since she started in 2012, Alexandra has hiked with over five thousand people from around thirty countries. Depending on the season, she brings in between $2,500 and $8,000 per month, peaking in July. She also now has four to five contractors working for her, depending on the season. To complement the business, she wrote a hiking guide, which has sold more than seventy-five hundred copies.
All she spends on each hiking tour is her time. She has a few annual costs (insurance, visitors bureau membership, web hosting), but aside from those, there are no fixed costs associated with running a tour. That means that anytime she runs a tour, it’s almost all profit.
If you’re passionate about where you live, you can turn sharing your city into a way to make money. Alexandra says that anyone who lives in a city could create a tour business, at least if they like the idea of walking and talking with groups.
You first want to make sure there’s a substantial number of visitors coming to your city each year. Then, see if there’s anyone else leading the same kind of tour that you envision. It helped Alexandra that San Francisco gets eighteen million visitors a year, but no one else was leading an urban hiking tour.
After five thousand people and counting, she’s now leading the way.
“Anyone who lives in a city could create a tour business. It costs virtually nothing to start! All I spend on each hiking tour is my time, and the income is almost all profit.” —Alexandra
FUN FACT One challenge of an outdoor business is having to cancel tours due to rainy weather. Normally, this only happens a few times a year, but in the winter of 2016 the rain was out of control. It was the wettest winter since rainfall has been tracked starting in 1895! Thankfully, business picked up again when spring arrived.
CRITICAL FACTOR
Most people associate San Francisco with cable cars and chocolate factories, but there’s also a great outdoors with scenic hills and trails easily accessible from the city. Alexandra leaves the city tours to other companies and focuses entirely on her “urban hiking” theme.
HUNGOVER ACCOUNTANT STARTS “MORNING AFTER” PARTY CLEANUP SERVICE
Feeling queasy after a night of hosting a party, this Australian accountant dreams up an unusual cleaning service that becomes a media sensation.
Drinking too much on a night out can have its consequences. You might wake up the next morning with a ton of regret and a wicked hangover to match. Most people in that situation just want to pull the covers over their head and wait for the storm to pass.
James Hookway, a full-time chartered accountant from Western Australia, had a different experience. For James, it was while he was hungover after a Christmas party that he came up with a crazy idea that changed his life.
He and his wife had thrown the party. The next morning, they lay in bed, dreading the inevitable cleanup process. While procrastinating about when to start the job, they began talking about how great it would be if there was a service that would clean up after your party—and maybe even bring you breakfast in bed.
After having a good laugh about it, they dragged themselves out of bed, made their own breakfast, and got to removing all traces of the night before. But the idea stayed with James…and like a fine wine, actually got better with age.
Fast-forward to six months later, and the concept still excited him. After conducting some research, he learned that although there were a lot of cleaning services out there, none of them marketed specifically to the hangover crowd. In fact, there wasn’t much differentiation at all—they were all generic companies with boring branding.
James decided to test the concept. To keep things simple, he created a Facebook page describing the proposed service and shared it with his friends and family. The name for the page almost wrote itself: he called it Hangover Helpers.
What happened next was like popping open a bottle of champagne on New Year’s Eve.
Perhaps it was the perfect name, the concept itself, or maybe the right person just happened to share the page. Whatever the cause, what followed was one of the wildest weeks of his life.
Print journalists from major publications, TV shows, and radio stations from all over the country contacted him for interviews. James had reached national exposure in less than two weeks, and everyone wanted to talk to the creator of such a comical (yet useful!) idea. This is something most larger companies are never able to achieve, despite expensive and time-consuming campaigns.
With all that free marketing, it was inevitable that customers would arrive faster than a headache after too many gin and tonics. And that’s exactly what happened.
His first booking came in that very week. James picked up basic cleaning products, a “Ghostbuster style” vacuum cleaner, and some food supplies for the breakfast.
He found the house in a state of total chaos, but that didn’t faze the new founder of Hangover Helpers. It meant he was able to get some “before” and “after” photos to showcase the type of work he was capable of. After the cleaning was done and the party hosts had enjoyed their breakfast burritos, James knew this could be a viable side business.
With the first job completed after a successful launch, he decided to build more of a brand around Hangover Helpers. This meant graduating from a simple Facebook page to an official website.
James figured that an investment in a professional-looking brand and website would be important, and he was meticulous in how he set it up. He wanted visitors to be able to fill out as many details as possible in order to get a detailed quote online before booking the service. That way, he could cut down on the administrative work and make the business much more efficient to run. This was especially important because he was still working at his job as an accountant.
Two years after starting, he had performed more than 250 “cleans” and earned $45,000, without spending a single cent on advertising. Business comes entirely through word of mouth and his social media presence on Facebook.
He’s cleaned up after everything from dinner parties all the way to full-blown extravaganzas that the cast of The Hangover movies would be envious of. Sometimes he’s shown up with people still asleep on the couches, and vacuumed around them. He once arrived at a party that was still raging early the next morning. It’s all in a day’s—or a morning’s—work.
The biggest, messiest party he’s seen achieved a scale of its own. A party of about 350 college students took place at a mansion while the parents were out of town. The backyard was the size of a football field, and there was so much mess left over that James had to call in reinforcements from a trash removal company. Even the helpers had a hangover after that one.
After operating successfully in Perth for two years, James expanded the service to Melbourne with the help of some dedicated cleaning teams on the ground. Although it isn’t making enough to pay all the bills just yet, James hopes that in the future he can expand to more cities and go national across the rest of the country. At that time, he hopes to be able to quit his day job and go all in on Hangover Helpers.
Raise a glass to this nonconformist accountant. He’s helping the party hosts of Australia recover, one hangover at a time.
“Find a niche market and develop a business strategy that is new and will be remembered. Make sure you can capture your audience’s attention straight away with a clear message of what you do, who you are, and why.” —James
FUN FACT The cleaning industry is worth around $4 billion annually to the Australian economy. That huge amount of money means there are over sixty-two thousand people employed as contract cleaners. It’s no wonder that there are literally thousands of cleaning companies across the nation.
CRITICAL FACTOR
There are thousands of cleaning companies in Australia, but only one that caters to the hangover crowd. The unique idea brought James a ton of media attention and launched his business.
FOODIE PR MANAGER BLOGS FOR FREE STUFF AND REAL MONEY
NAME
LOCATION
NEW YORK, NEW YORK
STARTUP COSTS
$1,300
INCOME
$25,000 IN YEAR THREE
WEBSITE
Two friends get paid to post photos of their lunch on Instagram. No, really! (And then one of them takes over the business, while working with more than 450 brands.)
By day, Alexandra Booze worked as an account manager for a public relations firm in Washington, DC. On nights and weekends, this foodie turned food and lifestyle blogging into a profitable side hustle.
It started with a project she shared with her friend Karen. Whenever Alex would visit Karen in New York City, they would always go out to eat somewhere new and interesting. It was during one of those nights when they were looking for their next meal that they decided to document all their fun foodie adventures. If you’ve ever wondered how to get paid for posting photos of your lunch, keep reading.
After a month of thinking about what their name should be, they launched East Coast Contessas. What started out as just friends and family liking their photos of food quickly turned into over one thousand followers.
For several months, they visited small bakeries, coffee shops, and food trucks and offered their services—reviews and social media campaigns—for free. With this attitude, they were able to feature a lot of different businesses. They also attended conferences, dinners, and festivals. Their goal was to meet chefs, concierges, and other food influencers. In other words…they hustled!
Once she realized there was a market for their reviews, Alexandra invested in some equipment so she could produce better media than what they were doing with their phones. She bought two cameras and a few interchangeable lenses. By keeping her eye out for sales, she only spent $1,300 on equipment that was worth at least $4,000. The new gear allowed her to create even better photos and video. Meanwhile, her consistent networking helped spread the word about their services.
To kick off the next year, Alex and Karen made a list of all the brands they wanted to partner with. They then reached out and pitched each brand personally. Since both of them came from media backgrounds, they already had a good handle on how to craft engaging narratives that would be interesting to potential partners.
They also knew that research was key. They spent time learning everything they could about a brand before making an offer. This level of research also helped Alex and Karen figure out how the brand would work with East Coast Contessas.
Their efforts paid off when they landed their first paid partnership with a national wine company. They leveraged that partnership and kept pitching to other brands on their list.
When it came to pricing, they offered multiple packages depending on the brand and situation. For some brands, it made sense to just do social media promotion for $300 per photo posted to their Instagram account. For other brands, social media promotion plus an editorial write-up on their blog at $1 per word was a better approach.
For brands that wanted to go all in, they’d offer social media promotion, an editorial write-up, and a promo video, which started at $400 on top of the other fees. They priced all these packages using three factors: the size of their audience at the time, the size of the company they were pitching, and the amount of work required.
In their second year of the project, they brought in $15,000—then in the first half of the third year, it was more than $17,000.
The East Coast Contessas eventually realized that the restaurant industry had a lot of crossover with the hospitality industry. They then started branching out to boutique hotels and mid-size national chains.
Before long, Alex and Karen were staying for free in fancy hotels. During those visits, they’d feature not only the rooms and amenities, but also the hotel bar or restaurant—a natural tie-in. This led to them receiving offers for press trips, where all of their costs were covered, as well as partnerships with tourism boards.
Alex and Karen eventually parted ways as business partners, with Alex continuing and Karen moving on to do other things.
Since launching three years ago, Alex has partnered with nearly 450 brands from the food and beverage, fashion, and beauty industries. And with dozens more partnerships lined up, she doesn’t have plans to slow down anytime soon—even as she moves to Prague to begin a new day job.
“Be open to new ideas and working with smaller brands. Everyone starts somewhere, and even smaller brands with limited budgets can still produce quality ideas and products.” —Alex
FUN FACT After completing and receiving payment on their first paid partnership, Alex and Karen went to Central Park and had a celebratory picnic with cans of wine from the brand that paid them.
ACTION PLAN
1. Identify a goal and a strategy: What do you hope to achieve in working with brands, and how will you help them enough to justify your fees?
2. Build the project on a shoestring budget. Spend as little as possible on gear, online services, and whatever supplies you need.
3. Be willing to work for free or in exchange for something else…at first. Use the initial gigs to establish credibility and then pitch paying clients.
4. Be specific about what you offer to provide. “Social media promotion” doesn’t give potential clients much info on what they’ll actually receive. “Three dedicated posts to our five thousand followers in your local area” is better.
CRITICAL FACTOR
Alex and her former business partner were willing to work for free—at least in the beginning. By approaching small businesses that wouldn’t normally pay for promotion, they were able to build a client list along with their following.
BUSY PROFESSIONAL CLIPS INTO BIKING WINE TOURS
NAME
LOCATION
PRINCE EDWARD COUNTY, ONTARIO
STARTUP COSTS
$20,000
INCOME
$100,000 IN YEAR TWO
WEBSITE
A marketing executive sees an opportunity to meet a tourism need in an up-and-coming wine region.
Erin Bury didn’t think she had time for a side hustle. As a partner in a creative communications agency, as well as a frequent speaker with the National Speakers Bureau, she had a lot on her plate. But she also had an idea that wouldn’t go away.
Erin had grown up visiting Prince Edward County, an up-and-coming Canadian wine region about two hours outside of Toronto. Her dad eventually moved there, and as an adult she continued to visit every summer with friends. They all loved touring the wineries—and they noticed that while there were limo tours available, there were no bicycle tours.
Erin knew this was a popular activity offered elsewhere. She also believed that if she didn’t enter the market, someone else would. As she put it, “If your idea keeps you up at night because you know you’ll be annoyed if someone else does it before you, it’s a good sign that you should pursue it.”
So a couple of years ago, and working with two of her best friends, Erin started the County Wine Tours. The first step to launching a bicycle tour business was figuring out a route that had enough wineries within cycling distance. Erin approached wineries on the potential route, making sure to find backup options in case of busy days or to accommodate any special requests.
When selecting wineries, she considered their offerings to make sure there was a good variety of tastings, an affordable cost, and the right location—both in terms of being close to each other and also close to a fixed starting point. The region has a converted rail line for walking, jogging, and biking, so Erin also wanted to include part of that trail in the tour.
With all these considerations in mind, Erin selected five primary stops and a number of backups for their guided wine tour.
Once the route was in place, the next step was to get some bikes. Luckily, a family member worked for Giant Bikes, the world’s largest bicycle manufacturer, so Erin connected with her to select a cruiser bike with custom accessories that would be comfortable and really stand out on the road. She purchased ten bikes, helmets, baskets, and repair tools.
Branding and marketing came next. Since Erin and her two cofounders all work in marketing, they had an advantage. They focused on a few key areas, first and foremost being search engine optimization (SEO) and Google AdWords, since most people start planning their wine weekend getaways by searching for a few specific phrases.
Setting up their TripAdvisor profile was another must for their business. They also invited members of the media to the area to take a tour, and partnered with a local bed-and-breakfast to invite their guests.
But just because they’re pros doesn’t mean they did it all on their own. As Erin said when we talked, “It’s impossible to do it all yourself. Whether you have cofounders, a virtual assistant, a freelancer or intern, or some other resource, having someone else to help you as you go will be imperative.”
She took her own advice, working with a freelance designer to create their logo, branding, website, and all marketing collateral. They also brought on an accountant to handle financial forecasting and accounting.
One thing Erin didn’t have to worry about was who was going to lead these guided tours. Erin’s dad and stepmom are both enthusiastic wine drinkers, as well as experts on the local area. They eagerly signed up to be part of the adventure.
After a lot of planning on weekends and evenings, the County Wine Tours spun into business. The tours are priced at $95 per person, and so far they’ve been completely booked up on weekend days. They also offer midweek tours, with anywhere from two to ten people each.
With up to a dozen inquiries coming in daily, Erin and her cofounders are excited that their great idea has gotten so much traction so quickly. Their biggest problem at this point is managing demand on popular days.
With the framework in place for public tours, they’ve also created private tours that people can book for a birthday party or bachelorette party, as well as corporate tours that companies can use as part of a retreat. Oh, and for those who prefer beer over wine, they now offer a brewery option.
Erin’s favorite tour is one she led herself. She hosted a private trip for her friends, which she assumed would be a special way to share her new project with them. But at the last tour stop, it became even more special when her boyfriend surprised her by proposing. The winery staff was in on it, appearing with sparkling wine the moment she said, “Yes!”
Though it made for an excellent photo op, Erin now has to manage expectations: “I make no guarantees that future tours will include a proposal!” she says.
While it’s clear that there’s lots of room for expansion, they plan to ride out this season with their current setup, and then decide how many tours to add for next year.
“It’s impossible to do it all yourself. I work on the business during the evenings and on Sundays, and I’ve outsourced functions like customer service, marketing coordination, and accounting so I can focus on the high-level stuff.” —Erin
FUN FACT Safety first! On each tour, cyclists stop at four or more wineries—but only one per hour, and each stop is limited to four tastings. The guides also provide bottled water and snacks along the way.
CRITICAL FACTOR
Bicycle tours to wineries operated in plenty of other regions, but not in Prince Edward County. Meanwhile, there were plenty of tourists coming to town. Erin put two wheels together and created the first-ever bicycle tours of the region.
FLORIDA MAN LEADS SCOOTER TOURS AFTER WATCHING RAP VIDEO
NAME
LOCATION
FLORIDA PANHANDLE
STARTUP COSTS
MINIMAL (HE TRADED SERVICES FOR THE BIKES)
INCOME
$50,000/YEAR
WEBSITE
A corporate refugee relocates to Florida and kicks off a new hustle leading adult scooter tours.
Jordan Crowler wears tank tops and a pair of board shorts to work most days, but five years ago he was working a typical job as an art director for a major corporation in Dallas, Texas. Wanting to break free from the golden handcuffs, Jordan worked his way into a full-time remote position. He had the goal of moving his wife and two young daughters to their dream destination—a little stretch of paradise in the Florida Panhandle called 30A, where The Truman Show starring Jim Carrey was filmed.
Not knowing a soul on 30A, and having to support his family, he decided not to tell his employer that he was moving. The company he worked for was going through a big merger, with layoffs happening left and right, and Jordan had already endured all sorts of corporate bullying and harassment. He still did his job well, but in the back of his mind, he knew the clock was ticking until a more permanent change would be required.
Being a resourceful person, he looked around his newfound paradise for new opportunities. One thing he noticed during his research was that bikes, skateboards, and walking were the preferred methods of transportation. It was far easier than dealing with parking, and the weather was almost always nice.
Not long after that, Jordan had what he calls his “Aha!” moment. Browsing on YouTube, he stumbled upon the music video for John Macklemore’s “Thrift Shop,” in which the artist undertakes an anthropological exploration to a number of secondhand stores in search of formerly unwanted items.
In parts of the video, Macklemore is seen riding on an old-school scooter. Jordan began to wax nostalgic about his early days spent meandering about on his old mongoose scooter. Chasing that nostalgia, he started looking for something similar to the scooter of his youth, but after some quick research, he realized that most scooters were just not as awesome as he remembered (a common problem with nostalgia).
But then he discovered a company called Kickbike, which takes all the best aspects of scooters and bikes, combining them into a single recreational product. Based in Helsinki, Finland, Kickbikes has been a growing sensation through much of Europe for over twenty-five years. They call themselves the “Porsche of the scooter industry”—perhaps a bit of a stretch, but they do have a passionate fan base.
Despite their international success, Jordan had never seen a Kickbike in the United States. He couldn’t believe that this fad hadn’t caught on yet, so he began to research the company. What he found was that the owner of Kickbike America actually lived right there in Florida, just a few hours away in Orlando.
Jordan drove down for a meeting, and asked if they could come to an arrangement that would lead to him being able to use the bikes on 30A. He felt that the business had a lot of potential for growth, so he offered to assist the owner in building up his brand presence.
With years of experience in web design and marketing, Jordan proposed a trade—he’d completely revamp the Kickbike US website and manage his marketing campaign for him. In return, the owner would give him some Kickbikes and a commission on all online Kickbike sales in the United States.
Before he knew it, Jordan was heading back to 30A, feeling victorious. He was towing a U-Haul containing his first twenty-five Kickbikes!
The real work began when he arrived home. His vision was to turn this truck full of Kickbikes into the next big thing, in the next big destination.
The 30A road runs along a coastline dotted with a dozen vibrant little beach communities that each boast their own unique vibe and flavor. Jordan thought the Kickbikes would provide the perfect vehicle for a fun, active tour that would enable people to get “off 30A” and see another side of this incredible place he called home.
Following the exposure that the area received when The Truman Show came out, this thirteen-mile stretch of road that had previously been a well-kept secret was quickly becoming a major tourist destination. But despite the growing tourism trend, no one was offering tours of the area.
Jordan had spent two full years exploring every inch of his new home—the rare coastal dune lakes, the state forests and parks, and all of the accessible trails, in addition to every business and street in each town. He’d made himself into an authority of the area, and he used his knowledge to create customized tours.
Getting his Florida business license and liability insurance was easy and inexpensive, but finding retail space in the area was much more of a challenge. Space was technically available, but it wasn’t cheap.
Not one to be dissuaded, Jordan started out by operating off the back of his truck in parking lots, and leaving some of his Kickbikes parked in high foot-traffic areas with flyers detailing how to get in touch with him to schedule.
Jordan strategically tailored his tours based on the fitness level of those who signed up. Kickbiking is more fitness intensive than bicycling, so he tried to feel out the expectations of his customers in order to ensure that it was a positive experience for everyone. Some tours sold better than others, so as time went on he focused on those and dropped the more experimental ones.
He also developed relationships with local businesses, and several of them ended up allowing him to use their shops as official starting points for the tours. This was a win-win, bringing new business to the shops, while allowing him to forgo paying for a rental space.
These days, the Kickbike side hustle is well past the kickoff point. Jordan ended up leaving his remote-work position to freelance as a web developer, and his tours and commissions are bringing in an additional $3,000 to $5,000 a month.
He’s now thinking about what comes next. Maybe he’ll roll his way into markets where the adult scooter trend hasn’t yet kicked its way down the road.
“It’s a cliché, but ‘fake it till you make it’ worked for me. I had to become the highest level expert on my product in the country, starting from scratch. Sometimes, to get the job of your dreams, you have to dream up the job, hire yourself, and then quickly prove you belong there.” —Jordan
FUN FACT Jordan is shifting the focus of his side hustle from tours and rentals to the fitness aspect of Kickbikes, introducing a class called “Kickbike Kardio.” This class is much less time-consuming than the tours, and allows him to spend time growing other aspects of his business.
CRITICAL FACTOR
The Kickbike brand is the “Porsche of the scooter industry” in Europe, but it’s largely unknown in the United States. After relocating to a stretch of the Florida coastline popular with tourists, Jordan was determined to bring Kickbikes to the masses.
EPIC SCAVENGER HUNT BECOMES SIX-FIGURE INCOME
NAME
LOCATION
BOSTON, MASSACHUSETTS
STARTUP COSTS
$150
INCOME
SIX FIGURES/YEAR
WEBSITE
An event planner creates a competitive scavenger hunt game that takes place across Boston. Can you really make money while having so much fun?
Chris Damianakos runs a scavenger hunt in Boston, Massachusetts. To understand where this seriously fun project began, we have to go back to the late 1980s when teenage Chris was on a family trip in Greece. It was there that he first witnessed a scavenger hunt being put on by an Italian tour group. He fell in love with the idea of playing a competitive game with other people, using the world as a game board.
Chris had grown up putting on tournaments and shows for his friends, and when he got back to the United States, he designed his very first hunt. In the movie version of Chris’s story, he would have gone straight from there to creating his own company.
Instead, he finished high school and continued on to college, where he majored in marketing. After college, he got a series of jobs in event management, both as a freelancer and contracting for companies. But he never felt fully fulfilled.
So a number of years later, he came back to the scavenger hunt idea that he loved so much when he was a teenager. As another passion project, he created an elaborate, six-hour long hunt for his friends and family. They loved it! A friend that was in marketing couldn’t stop talking about what a great business this would be.
Chris then spent a few months redesigning the hunt so that it could be played in two hours instead of six—the theory being that not everyone would be up for a six-hour hunt, no matter how awesome it promised to be. He then launched his new venture, which he called Cashunt.*3
This project began in the dark ages, more than a decade ago, when social media was just getting off the ground. Chris decided to place ads in the wedding parties section of a local newspaper, to see if he could attract bachelorette and bachelor parties.
The plan worked, as his first group scavenger hunt was a bachelor party. He was simultaneously excited and petrified since he had never done a hunt for the general public before. He charged them $30 per person with an eight-person minimum…and the group was thrilled!
That first year he did five games and made a couple thousand dollars. Since his initial investment was so low—the newspaper ads, materials for the game itself, and his time—most of what he made was pure profit.
During that year, he also landed a wireless provider as a corporate client. The company asked him to customize the scavenger hunt for their employees. It took some figuring out, but after that first experience, he created a blueprint to make customization for future corporate clients easier.
Even without specifically pursuing corporations, he continued to get one or two corporate clients a year, who used his scavenger hunt as a team-building outing. Since he customized scavenger hunts for each company, he charged them more per person and had a minimum of 10 participants instead of 8, with a cap of 250.
Over the next few years, Chris kept advertising in newspapers. Because this was a side hustle and he wasn’t dependent on the income, he enjoyed making the game as epic as possible. For example, he designed a fully interactive game that used the city of Boston as the board. Players start off with a comic book that has some initial challenges in it. They have to decide as a team how they’re going to get the most points before the two hours are up.
Sometimes challenges lead to point cards, sometimes they lead to other challenges or scannable codes that send them to an online puzzle. At one point, he even created a prop that looked like a real newspaper. Players had to find it, and then use it to complete the challenge. As Chris described it, “I wanted to make it as much like one of those reality TV shows as possible, so people could get that experience for an afternoon.”
Chris continued to put on more and more scavenger hunts and saw his revenue increase steadily, solely through word of mouth and newspaper ads. Four years after starting, his annual, part-time income was up to $30,000.
And then his business started to take off even more, but not because of anything he did directly. Review sites like TripAdvisor and Yelp had gained momentum, and all of a sudden he was getting excellent reviews, furthering his word-of-mouth marketing in a more technological way.
As his reputation on review sites grew, so did the business. He finally decided to jump into Cashunt full-time. Not only had his revenue gone up, but the increased volume of interest by way of phone calls, emails, and interactions on social media (which was now much more common) served as further confirmation.
Once he decided to focus all his attention on the business, he started increasing the number of games in the Boston area. He invested in technology to add in additional interactive elements. Over the years, the prizes also got better, with each winner now receiving a medal.
He switched to a commercial bank account to process credit card payments, and stopped running newspaper ads in favor of online ads. He updated his website, bringing it forward nearly a decade into present-day standards.
Over the years, Chris had been approached a few times about franchising Cashunt in other cities. He always deferred, instead making one-day round-trips to other cities himself for corporate clients. But soon he was flying back and forth to Chicago so often that the commute was getting impractical. When he was once again approached about franchising, he finally considered the idea.
He flew to each city to meet with the interested parties, scoped out the area, and entered into collaborative partnerships with existing tour companies in five different cities.
It’s been quite the journey since that first six-hour hunt Chris made for his friends. He’s now making well over six figures a year. He has one other full-time employee working with him in Boston, and facilitators in several other locations. He also has plans in the works to expand further.
Oh, and he’s still having a lot of fun.
“If you want to start a side hustle, don’t listen to the noise, listen to yourself. And be prepared to put in the time! This isn’t like an office job where you just clock in and clock out.” —Chris
FUN FACT The scavenger hunt has now expanded internationally, with a new location that opened up on the island of Crete in Greece.
CRITICAL FACTOR
A successful scavenger hunt is made up of two critical qualities: fun and organization. Chris brought both of them to Cashunt, refining the process along the way and continuing to improve from gig to gig.
In some ways, producing a successful event is like developing an online course: you need a reason to bring people together, and the right venue or space for them to meet.
But a conference, meetup, in-person class, or other event has at least one big difference: a fixed deadline that comes with other unchangeable variables. If no one signs up for your online course on ballroom dancing, you can try again later. But if no one shows up at a physical venue you’ve booked, you have a bigger problem.
Right from the beginning, you’ll need a clear plan for how you will attract people to your event. This should include an easy way for them to sign up (and pay in advance whenever possible) so that you know what to count on.
If you can avoid paying for a venue for your first event, do so. Community centers, schools, and religious institutions that are often empty throughout the week can be good options. In some cases, bars and restaurants will be happy to host your group, especially if you commit to spending a minimum amount on food and beverages there.
Make a simple projection of how many attendees you’ll need for your event to be successful. Of course, you’ll want more than the minimum standard of success, but this way you’ll have a baseline goal.
Perhaps most important of all: When it comes to events, publicity matters a lot. Shout it from the rooftops!
For more, visit SideHustleSchool.com/events.
*1 Alexandra keeps detailed records. She spent $99 on a premium website hosting account and $15.36 on a set of 250 business cards.
*2 Arguably, his true startup costs were less than $1,000. The $25,000 investment in a website and better cleaning gear only happened after James had established the business as a winning concept.
*3 Everyone thinks the name refers to a cash prize, but it’s actually short for Chris, Areti (his wife’s name), and Super Hunt.