Ramp Up: Million-Dollar Side Hustles
Side hustles are great for earning extra cash—and sometimes they earn a lot of it. These stories represent people with hustles that produce high six figures or seven figures in annual income.
Chicago Woman “Hangs Out” with Etsy-Inspired Business
Renegade Museum Tour Guide Earns $2 Million
Aerospace Engineer Becomes Full-Time Rideshare Expert
College Student Earns $20,000 per Month Cleaning Houses
Target Store Manager Makes $45,000 per Month Blogging
All-American Hits Home Run with Baseball Apparel Hustle
Accountant Earns $233,751 Reselling Items from Walmart
CHICAGO WOMAN “HANGS OUT” WITH ETSY-INSPIRED BUSINESS
NAME
LOCATION
CHICAGO, ILLINOIS
STARTUP COSTS
MINIMAL
INCOME
MULTIPLE SIX FIGURES/YEAR
WEBSITE
A Chicago-based plastic recycling sales rep transforms her love for DIY lamp shades into a multimillion dollar business.
Jennifer Brown has been starting projects since she was ten years old, beginning with selling Beanie Babies on eBay and dog sitting for $30 per day. In high school, she tried repainting abandoned furniture from an alleyway. Then, in college, she found her stride and took her creativity to the next level.
At a local craft show, Jen saw a liquor bottle with lights inside of it. Always looking for her next DIY project, she decided to make one for herself. Once she’d placed Christmas lights inside a painted liquor bottle, her friends kept asking her to sell them one—so like any resourceful artist, she followed through on their requests.
Then, one day, she tried something else: Jen covered a balloon in Elmer’s glue and wrapped it with yarn to create a lamp shade. She had never seen anything like it. That very same day, a good friend told her about the online marketplace called Etsy.
Within a week, Jen had listed her creation and made her first sale for $60. She sold a second lamp shade a few days later for another $40. With a $300 rent payment looming, $100 was a significant amount of money.
What excited her most was that she was just getting started. What would happen if she invested more of her time and efforts in making more fixtures?
She began looking around for other things on Etsy that she could create. She saw some wooden chandeliers and, much like the lighted liquor bottles, thought, Hey, I can make those too!
Not only did her bedroom transform into her production studio, but sometimes she couldn’t use her shower because she had hung so many yarn spheres in there to dry. Every time she received a customer request for a new color, she would make it for them, take a picture, and add it as another item in her store. This organic growth was wonderful, but one can only make so many yarn lamp shades.
As she was quickly outgrowing the limited production capacity of her bathroom, Jan decided it was time to charge more. In a story as old as time, the more she raised her prices, the more she sold. Years later, she still recalls the moment she realized she could turn $10 in supplies into a $300 light fixture.
For years, her DIY lighting hustle was just a side gig as she worked her day job as a sales rep at a recycling company. In fact, it was the job that had made selling on Etsy so easy. Her background in sales, marketing, graphic design, and search engine optimization (SEO) put her leaps and bounds above other home-crafters selling their wares at the time.
Since Jen could work from home a few days per week, everybody told her not to quit her day job. For years, she dutifully maintained the status quo, working full-time and selling her wares on the side. That is, until one day, when a friend asked her to question the opportunity cost of continuing to keep both jobs.*1
With that change in perspective, Hangout Lighting became more of a priority. Jen knew that she couldn’t continue to grow the business if she was building lights all day long, so she began to consider hiring employees to help out.
Going all-in allowed Jen to brighten up Hangout Lighting’s sales to multiple six figures. What started as a side hustle now gives Jen total financial and schedule freedom. The Etsy side of Hangout Lighting grew to $1 million in sales in just three years. Between her various online channels, she now brings in up to $70,000 per month.
While she could be taking home large profits per month, Jen reinvests much of it back into the business to, as she puts it, “continue growing my dreams.” By pursuing those dreams, her bright ideas have brightened up thousands of homes.
“Make sure you have high enough margins, and keep improving as you go. Learn from each sale about what people want—then do more of that.” —Jen
FUN FACT Jen may have turned her side hustle into her main business, but she still likes to dabble in new projects from time to time. And occasionally, whenever she sees rare Beanie Babies for sale, she can’t resist picking them up for old times’ sake.
CRITICAL FACTOR
Jen applied marketing smarts to DIY crafts, and then carefully built on her initial success by hiring the right employees and reinvesting in the business.
RENEGADE MUSEUM TOUR GUIDE EARNS $2 MILLION
NAME
LOCATION
WORLDWIDE
STARTUP COSTS
MINIMAL
INCOME
MULTIPLE SEVEN FIGURES/YEAR
WEBSITE
A New York City man goes on a forgettable date, but falls in love with the idea of creating his own museum tour company.
Several years ago, on a Saturday night in December, Nick Gray was on what was supposed to be a romantic date. He and his companion were taking a private tour of the Metropolitan Museum of Art. As snow fell outside over New York City, they traveled through the Met’s dimly lit hallways and cavernous rooms, filled with sculptures, paintings, and Egyptian artifacts.
According to Nick, that night something magical happened: he fell in love…with the museum.
As for the date, that relationship didn’t work out. In fact, he barely remembers her. Instead, he remembers being entranced by the artworks all around him, documenting more than five thousand years of human history.
These observations quickly turned into an obsession. While Nick spent his working weeks selling avionics equipment—a job he was happy with—he started spending every weekend at the Met.
He began offering free tours of the museum to his friends and family, which mainly consisted of showing them his favorite things. He says he was having so much fun doing the tours that the first time someone tried to offer him $20 at the end, he turned it down.
As word spread of his skill, the off-hours tours began consuming more and more of his time. Given his newfound love for museums and desire to share it, he decided to set up a side business.
His idea was to offer nontraditional, “renegade” tours at the world’s best museums. By this point, he had increased the quality of his tours, using library research as well as turning to the trusted friend of every student who’s written a paper in the past fifteen years, Wikipedia.
His friends started telling their friends, and the word continued to spread. At one point, a blog wrote about his tours, and the next day Nick received hundreds of requests to sign up. He officially launched his company, Museum Hack, a few months later, offering public tours for $59 a person and private tours for $99 a person.
The setup was simple: Nick financed almost all of his startup costs, including a website, by charging for the tours. And he attracted most of his customers simply through word of mouth. After guests went on the tours, they would post about them online, creating additional interest.
He also started hiring part-time guides, who now include Broadway actors, stand-up comedians, and scientists. These guides design their own routes, based on what they’re most passionate about. The museum benefits too. Museum Hack pays them an admission fee for each guest.
The goal is to tap into a whole new market of museum goers: essentially people who think they hate museums—a group which, Nick admits, used to include him. His tours are two to three times faster than traditional ones, incorporate games throughout, and reveal the juicy gossip behind the paintings and other exhibits. One of the taglines he uses is “This isn’t your grandma’s museum tour.”*2
It’s safe to say all of this touring has been a huge success. In its first year, Museum Hack made about $40,000. In the following year, income increased twelvefold, to just under $500,000. About two years after launching the tours, Nick’s side hustle officially became his full-time gig. He still liked his day job, but running a part-time project of this size was like painting the Sistine Chapel at night while working as a bank teller during the day.
At last count, Museum Hack has led over twenty-one thousand people on semiprivate tours in five cities. The business has sixty-plus employees, as well as contractors and associates who regularly do tours and events, along with a leadership team that keeps everything running smoothly.
As the team expanded, Nick made another big change, promoting his chief of staff to take over his job as CEO. He continues to be highly involved, but he felt like someone more focused on process and organization would be better suited at the helm. Accordingly, he’s shifting his focus to an advisory role, and looking for more creative ways to expand the business even further.
A side hustler at heart, Nick is already busy with a new hobby—this time, hosting a pioneering style of cocktail parties. Naturally, he’s testing it out on his friends first.
“Do it for your friends first! I spent hundreds of hours giving my friends free museum tours so I could create an entirely new product. This feedback from them, in combination with their word-of-mouth referrals, is what helped me launch my business.” —Nick
FUN FACT In one recent year, twenty-six guests got engaged on marriage proposal tours. And yes, they operate tours designed specifically for popping the question.
CRITICAL FACTOR
“Museum tours for people who hate museums” proved to be a powerful selling point. Then, as Nick branched out and began to hire guides, he made sure that visitors would have a stellar experience by choosing people with outgoing, engaging personalities.
AEROSPACE ENGINEER BECOMES FULL-TIME RIDESHARE EXPERT
NAME
LOCATION
LOS ANGELES, CALIFORNIA
STARTUP COSTS
MINIMAL
INCOME
MULTIPLE SIX FIGURES/YEAR
WEBSITE
A Boeing employee earns $34,000 in one weekend referring drivers to Lyft, and then sets out to become an industry expert. His website now brings in multiple six figures annually and receives hundreds of thousands of visitors each month.
Like several of our featured stories, Harry Campbell’s extracurricular activities began at an early age. In his case, it started in the high school lunchroom. His mom made the best lunches, and the other kids would offer him money for them.
Eager to capitalize on this opportunity, Harry started asking his mom for two bags of chips, two iced teas, and sometimes even two sandwiches—reselling the extra items to his classmates for a 100 percent profit. He still remembers his best customer: a girl in English class who bought a bag of chips every day.
Many sandwich sales later, he became an aerospace engineer for Boeing. The job paid well, and when Harry started driving for Uber and Lyft on the side, some of his friends and coworkers made fun of him. Why did he need to ferry people around after he’d already worked a full day?
Well, for Harry, it wasn’t so much about the money he earned for each ride as it was the idea and the opportunity. He’d started driving in the early days of ridesharing, when the companies were desperate to sign up drivers and began awarding a lot of incentives for referrals.
In fact, the incentives were much more lucrative than the actual driving. He first signed up for Lyft, but then earned $500 for joining Uber and completing a single, ten-minute ride.
He struck the mother lode of incentives when Lyft ran a promotion offering new drivers $1,000 for doing one ride, and paid the referring driver $1,000 as well. Harry spent three days trying to convince everyone he knew to sign up. People told him it sounded like a scam, but it wasn’t—he ended up referring thirty-four drivers and earning a $34,000 bonus.*3
When he first started driving, Harry noticed a lot of people were asking the same questions over and over in Facebook groups for drivers, but no one had the definitive answers. It seemed to him that if he could create a resource that answered those questions, it could get people off Facebook and onto his website, granting him the authority in this new industry.
At first, the site was just another part-time project. Harry made around $25,000 from it that first year, a lot more than he was expecting. But traffic was growing, he was starting to get more media attention, and he figured that if he went full-time, the numbers would only get better.
So once his new site, The Rideshare Guy, was getting around one hundred thousand page views per month, he quit his day job. He was pretty sure that he was going to eclipse his engineering salary within a year, and just in case it didn’t work, he had a good emergency fund saved up.
He didn’t need the emergency fund. In his first year going all-in, the business made over $100,000 in profit. He’s now expanded into advising and advertising. A team of two full-time employees handle content management, and around ten freelancers do everything from writing and making videos to virtual assistance and editing. It’s a rideshare empire!
Year after year, Harry continued to grow the business. He wrote a book and began consulting with auto manufacturers and public policy experts. He even planned to host the first-ever rideshare conference.
In the midst of all the rideshare projects, his wife gave birth to their first child. Because of the flexibility that his new work provides, he was able to take several weeks for full-time child care, and then work half-time for a couple of months. From the lunchroom where he hustled chips and iced teas to leaving his engineering job to become an expert in a new industry, Harry’s willingness to follow his curiosity and to experiment has led him to a life where he’s fully in control.
If you find yourself in need of a ride in Los Angeles, pay attention to who your driver is. Once in a while, he still turns on his Uber or Lyft app to pick up passengers. He says that it keeps him on his game.
“I think finding the right side hustle is all about trying lots of different things. It’s important to do your due diligence and research ideas without jumping right in, but at a certain point, you need to just start experimenting.” —Harry
FUN FACT I first met Harry when he attended a book event of mine in Orange County, California. He gave me a ride back to the hotel that night—and I didn’t even have to pay!
CRITICAL FACTOR
It’s estimated that more than three million people have signed up to drive for rideshare companies. Until Harry created his website, however, there was no central gathering point for them to share information.
COLLEGE STUDENT EARNS $20,000 PER MONTH CLEANING HOUSES
NAME
LOCATION
WASHINGTON, DC
STARTUP COSTS
MINIMAL
INCOME
$20,000+/MONTH
WEBSITE
A Washington, DC, student identifies problems in the cleaning industry, then takes his insights to the bank—all without ever scrubbing a floor of his own.
Christopher Schwab’s side hustle turned into his main gig in a very short period of time. The business is called Think Maids, a residential cleaning service in the Potomac area of Washington, DC, Maryland, and Northern Virginia.
He started Think Maids during his last semester of college. Even as a student, he spotted a demand for transparent, high-quality cleaning services. Every city has a ton of cleaning companies, but many are unreliable and have hidden costs.
Christopher believed he could fix many of the complaints people had about cleaning companies. He also thought the cleaning industry was a safe option for a side hustle, because there’s no shortage of people who need their homes cleaned. The way he saw it, it was simply a matter of learning how to effectively reach those people.
After researching the competition and mapping out how he’d deal with the common problems in the industry, Christopher started by putting up a website with instant online booking. He then added his business profile to Yelp, Thumbtack, and other forums where customers actively look for cleaning services. He made sure his online presence was impeccable, unlike most maid company sites that are outdated and don’t accept online bookings.
Next, he worked to find reliable, quality cleaning teams. He posted recruitment ads on Craigslist, set up interviews, and had people clean his own apartment so he could see how skilled they were.*4
He learned to trust and verify. When he hires someone, he gives them a few jobs their first week to battle-test them before deploying them to a dozen houses or more in a few days. Several prospective cleaners said they had a lot of experience, so he didn’t interview them…but none of those people worked out. Lesson learned: Always do the interview.
In launching Think Maids, Christopher discovered that the three biggest problems with the industry were reliability (cleaners being late or just not showing up), the hassle involved with booking (since many services didn’t accept online bookings), and the lack of honesty or integrity.
To address these problems, he makes sure he works with cleaners that are easy to contact, punctual, and personable. Think Maids offers simple online booking, easy schedule changes, and the ability for clients to share special instructions. The company is easy to contact by phone, email, or text, and has a goal of trying to respond within five minutes.
When a customer schedules a clean, they get a reminder email three days before, one day before, and then on the day of their clean. They also get text messages when the cleaner is on their way. After each booking, customers get an email asking for a rating.
Customers receive a phone call the day after a cleaning to see how things went and if they want to sign up for a regular service. If there’s a problem, Think Maids will call the customer as soon as they find out about it, and work to make it right for them that same day or as soon as possible.*5
In a short period of time, Christopher had ten people who cleaned for him on a regular basis, as well as two assistants who helped with booking, scheduling, feedback calls, and other tasks.
He was also earning up to $20,000 a month. A big portion of revenue comes from gently pushing clients to sign up for recurring services so that he can count on their business month after month. Additionally, he focuses on move-in or move-out cleans on the last week of each month, where weekly income is twice that of the other weeks. Other maid services are typically booked up then, but Think Maids makes sure to have availability.
The best part of the experience is having enough time to do what he wants. Christopher has worked hard on automating and delegating as much as he can.
His goal is to grow Think Maids to $50,000 a month while only working three to four hours a day. He’s also putting thought into a second side hustle that complements this one.
Meanwhile, he’s cleaning up.
“I was working on the cleaning company during my final semester at college. I grew it enough that once I graduated it shifted effortlessly to my main work now.” —Christopher
FUN FACT Christopher was able to travel to Japan for ten days, and his hustle didn’t slow down. This was only possible because he had built systems in his business that weren’t dependent on him.
ACTION PLAN
1. This kind of business isn’t really about cleaning—it’s about systems. Instead of going out to clean houses (or whatever you decide), think first about how to construct the project in a way that doesn’t rely on you to do much of anything once it’s going.
2. Follow Christopher’s model of radical customer service. Be reliable, honest, and quick to reply to inquiries.
3. For every customer interaction, devise a script or protocol that others can follow. If a customer is unhappy, how should your team respond?
4. After going above and beyond, ask for referrals.
CRITICAL FACTOR
How is it possible that such a common industry could be plagued with such consistent problems? Christopher didn’t understand why either, and he set out to address those problems from the outset. The proof is in his many positive reviews—and, of course, his $20,000 a month in billings.
TARGET STORE MANAGER MAKES $45,000 PER MONTH BLOGGING
NAME
LOCATION
SAN DIEGO, CALIFORNIA
STARTUP COSTS
MINIMAL
INCOME
MULTIPLE SIX FIGURES/YEAR
WEBSITE
He’d been interested in personal finance since he was thirteen, but he had no idea this passion would go on to transform his life, earning a huge profit even as he continued working his first job at Target.
Investing has been a lifelong obsession for Robert Farrington. From when he first sat down to help his dad with his taxes at the wise old age of thirteen, to a few years later when he received $1,000 from his grandfather to buy his first stocks, he was hooked.
When he got to college, Robert was hoping to find some of his peers and share his ideas by joining their investment club. But when he turned up at the club’s meeting, he was disappointed to learn that all of the advice they were giving was centered on penny stocks and day trading. This was advice he not only disagreed with, but also felt was outright bad for students to follow.
He started a blog, The College Investor, to be a transparent voice and share the strategies he felt were more honest and viable for students.
Using a free website template and spending only minimal amounts of cash, Robert published his first post that first year of college. He committed to post three times per week, and spent most of his first year as a blogger to learn the trade.
He didn’t know anything about marketing or writing or creating headlines—but, as he put it, “nobody was really reading the site anyway,” so he could afford to make mistakes. Gradually, he learned what the people who did read the site responded to.
Then, almost a year and a half of writing later, The College Investor finally made its first $25 of income through an affiliate product sale. He’d spent fifteen months working for that $25, but Robert couldn’t have been prouder. He knew his site was no longer just a passion, but a business.
All this time, Robert was going to school and working at Target. He started as a team member and then became a supervisor. After graduation, he became an assistant manager, and finally a full store manager in his hometown of San Diego.
And as he rose through the ranks at Target, the income on his blog began to rise as well.
The main source of income came through affiliate commissions. In posts and guides on the site, Robert will recommend a product or service—like an online broker, a real estate investment, or student loan refinancing—and if a customer chooses to buy through his link, he receives either a flat fee or a percentage of the sale.
This requires Robert to consistently create good content so that people trust and believe his recommendations. Relationships with readers can take months or years to build, but once you get the right content with the right recommendation in front of the right reader, the commissions can start to roll in over and over.
The site has come a long way since that first $25. When we profiled Robert for Side Hustle School, it was pulling in as much as $45,000 a month. That’s not a typo, and there aren’t many expenses. It’s simply a lot of money, all built on a lot of commissions from a lot of customers.
After seven years in both roles, Robert finally quit his job at Target to transition himself into being the full-time CEO of his site. He hopes the change will allow him to give his business an extra push to become the go-to site for student investing in America.
“Your first year of blogging is about learning, and you have to remember to put in that practice if you want to be successful.” —Robert
FUN FACT Over the years, most of Robert’s coworkers at Target didn’t know about his “other job,” but once in a while someone would approach him and say something like “I saw an article in Forbes…and it was written by you!”
CRITICAL FACTOR
Robert chose a profitable topic to write on, and then he just kept writing, day after day. The eventual reward was well worth the effort!
ALL-AMERICAN HITS HOME RUN WITH BASEBALL APPAREL HUSTLE
NAME
LOCATION
PORTLAND, OREGON
STARTUP COSTS
$3,500
INCOME
MULTIPLE SEVEN FIGURES/YEAR
WEBSITE
After first learning to use design software to forge his report card, a Hawaiian baseball enthusiast creates a clothing line that goes on to earn millions of dollars.
A native of Hawaii, Travis Chock has always loved baseball. He started playing when he was five and hasn’t stopped since. He would go on to make the club baseball team at the University of Oregon and transform himself into a two-time All-American. Baseball wasn’t just a sport—it was his life.
So it comes as no surprise that Travis’s first job would be related to his favorite pastime. Drawing on his sports experience, he sought out a job as a junior varsity coach at a nearby high school, but discovered there just wasn’t a strong baseball culture in Eugene, Oregon. For someone whose identity was centered around the sport, Travis was shocked. As an Asian American from Hawaii, he didn’t feel like he fit into any social groups in school, and baseball was where he found people he could relate to.
Since the baseball community in Oregon was in need of some cheerleading, he decided that he’d try to fill the void himself. He got together with some former teammates from his club baseball days, and they worked to put together a series of youth baseball camps.
For each week that summer, Travis and the gang taught twenty-four kids between the ages of seven and twelve everything they knew about the sport they loved. They called the camp—and eventually their growing business—Baseballism.
Most camps give out free T-shirts to participants, but they don’t put much effort into design or print quality. Travis wanted his shirts to look good. He used Adobe Photoshop and Illustrator, which he had experience using in school.*6 When his knowledge was insufficient, he would watch online videos for the information he needed.
The summer camp ran successfully for two years, but eventually the four friends went their separate ways and got “real jobs.” Travis ended up scoring employment as a physical education teacher, assuming that his side hustle had run its course. But little did he know, Baseballism wasn’t going to sit on the bench for long.
Travis continued to wear his camp T-shirts around town. Once in a while, people would stop him on the street and ask him where he purchased his shirt. He casually brought it up one day with his old partners, and discovered that this wasn’t an isolated trend—people were asking them where they got their shirts too. It seemed like an opportunity was calling from the bleachers. The infield team began to consider how they could transition Baseballism into an apparel company.
Travis took a chance and used $3,500 from a credit card to get their new side hustle off the ground. They used the money to launch a fund-raising campaign, featuring a preliminary batch of Baseballism-branded shirts, baseball caps, stickers, and computer backgrounds for their supporters.
After fifty-five days, they exceeded their campaign goal of $13,000 and got to work. Travis hit up a local screen-print shop, which recommended several blank T-shirt manufacturers. His team decided among them by taking a look at the samples they provided.
It helped that the other three teammates had specialized skill sets as well. One had become a lawyer, another worked in finance, and the last had experience in sales and operations. Their skills complemented one another, and they operated with a philosophy found in baseball: “Know your role, trust your teammates, and don’t get in their way.”
Travis’s garage became Baseballism HQ for all incoming and outgoing orders, and they focused their attention on building a strong audience through social media. They used quotes like “You’ll never know until you dive” and “Live life like a 3–1 count”—none of which would make much sense if you didn’t play baseball, but that was the point.
The posts kept going, to the point where Travis maxed out his limit for posting on Twitter in the first few days. This proved crucial to the success of Baseballism as they attracted only the right people who would buy their product. It also created an exclusive community of baseball fans that deeply supported them, and their business exploded.
Sales of the new apparel line grew so much during the holidays that it was no longer feasible to run the business out of Travis’s garage. It was one thing when Travis started experiencing issues maneuvering around all of the merchandise, but it became more pressing when his neighbors began to complain about the trucks that were taking up all available road space when they were collecting shipments from his house. It was a good problem to have, but it also meant that they needed to look into a more permanent solution.
They eventually rented a small storefront—but, like the garage, it was quickly outgrown as they brought in over $300,000 in revenue their first year. Travis became the full-time CEO of Baseballism, Inc. in year two. The business would go on to do $1.3 million in revenue that year, $2.7 million in year three, just under $7 million in year four, and more than $10 million in year five. They now have four brick-and-mortar stores, with plans for several more. What had once started out as a passion project has taken off and turned into a thriving business.
The road to the playoffs has sometimes gone into extra innings. Travis remembers packing orders till 3 a.m. while holding on to his day job and other commitments. Still, there’s nothing else he’d rather do, as he says that “it is the closest thing to being in the big leagues.”
Clearly, Travis and his friends have knocked it out of the park.
“You’ll never know if something will work unless you dive in headfirst.” —Travis
FUN FACT As a nod to their history with baseball and passion for the sport, each of the partners for Baseballism has a picture of himself from Little League on his business card.
CRITICAL FACTOR
When the four guys teamed up to serve fans of a sport they loved, they each brought unique skills to the partnership.
ACCOUNTANT EARNS $233,751 RESELLING ITEMS FROM WALMART
NAME
LOCATION
MINNEAPOLIS, MINNESOTA
STARTUP COSTS
MINIMAL
INCOME
MULTIPLE SIX FIGURES/YEAR
WEBSITE
A young accountant masters the art of reselling, purchasing textbooks, dental floss, and Cheerios from retail stores in bulk—then earns hundreds of thousands of dollars in profit by selling it online.
As an accountant at a large firm in downtown Minneapolis, Ryan Grant’s main responsibility was working on financial statement audits for a variety of clients. At night—or whenever he had the time—he transitioned to a very different role as an online reseller.
Ryan had grown up on a small farm in southeast Minnesota. His family grew pumpkins and strawberries to sell, and raised a variety of animals.
The projects on the hobby farm weren’t highly profitable, but they helped him learn the values of hard work and delayed gratification from an early age. With pumpkins, for example, you have to plant the seeds in the spring, take care of them all summer, and you don’t get to harvest them until October. Understanding this lesson was a very valuable experience for what came later.
In college, he began to experiment with the art of side hustling, buying and reselling textbooks. We could call this episode of his life “Ryan vs. the university bookstore.” At the close of his first semester of freshman year, he went to the college bookstore to sell back his books. They offered a low price compared to what he had paid for them, so he turned around and sold them online for significantly more. And the next semester, he started selling books for friends in return for a percentage of the sale. The pumpkin patch mentality was blossoming.
After that, Ryan started buying textbooks directly from students on campus. He and a friend set up a table in the student union right next to the college bookstore, at the same time the bookstore was buying books back at the end of the semester.
They put a sign on the table that said “cash for books.” They would also stop students as they were walking by to say that they were buying textbooks and paying more than the bookstore.
They said they could make those students an offer on the spot, or the students could get a quote from the bookstore and they would beat it by at least 10 percent.
At first, the bookstore didn’t mind them being there, and they actually sold them some books. The store had a program where they would pay at least $1 for every book, no matter how many it already had in stock. This led to them buying books they didn’t need, so Ryan was able to buy them direct from the bookstore for a fraction of the current selling price. After he bought all of the books, he would then resell them online.
Eventually, however, the bookstore wised up and realized they were losing a lot of business to these ambitious students.
Ryan and his hustling friend were summoned to a meeting with the university’s legal department. They were told that they needed to shut down the website or start paying the school a fee. They responded with a logical argument: “We’re already paying the school a lot of money. It’s called tuition.”
For some reason, this argument was unpersuasive. They weren’t able to work out a deal, and ended up shuttering their textbook hustle.
With the college textbook hustle behind him, Ryan was eager to experiment further. He graduated from college and began work for an accounting firm, but his focus was elsewhere.
Then, like a few other people you’ve read about in this book, he started selling online using the Fulfillment by Amazon program. With this program, you’re able to ship your inventory to Amazon’s warehouses, and they take care of the rest—you just have to respond to messages and handle any issues that come up.
At first, he sold textbooks, since that’s what he knew, and then he began to buy items at local stores to sell online. He discovered that with enough research, he could sell items online for more than what he paid for them in person. By working about ten hours a week, he quickly found a way to make an extra $1,000 a month. That was a good start…but what would it look like if he could spend more time—and also get smarter about the process?
In short, it looked like a lot more money.
Ryan learned to purchase products from big-box stores like Walmart, Target, and Home Depot, and then resell them online for a higher price. He also learned to find wholesale sources, typically manufacturers and distributors of existing brands that are looking to have their products distributed online.
He focused on improving his skill in the art of reselling itself, not what kind of products he should specialize in. In fact, he didn’t specialize in any kind of product at all. He sold items in just about every category you can imagine, everything from dental floss picks to maximum strength Ex-Lax to silverware sets to video game consoles. If he could find a way to profit from the difference in price between buying and selling, he’d do it.
For the first twenty-one months that Ryan worked on this project, he earned more than $230,000. He paid himself a salary of $60,000 a year, and invested the rest of the profits back into the project. This was a few years back, and the growth hasn’t stopped. The not-so-small project has crossed the million-dollar point in sales and continues to produce hundreds of thousands of dollars in annual profits.
Ryan quit his job at the accounting firm to focus full-time on reselling. He says the greatest benefit is freedom of schedule. When he started, his number one goal was to feel more in control of his life and not have anyone telling him how to spend his time. It’s safe to say he’s achieved this goal in full.
From his early days in the pumpkin patch, to the brawl with the university bookstore, to clearing out the shelves of Walmart while looking for products to resell, Ryan has created a tremendous source of security—and an all-new life for himself.
This is the way of the side hustle.
“I quit my job as an accountant to pursue selling online full-time. I walked out of the office on that day with a big smile on my face, and I’ve never looked back.” —Ryan
FUN FACT Ryan has sold products in just about every category you can imagine. His strangest success? A particular flavor of Cheerios that he sold over and over for $19.99 a box.
CRITICAL FACTOR
Specific products were irrelevant to Ryan. He focused entirely on pricing arbitrage: buying at one price, and selling for a higher one. He improved his skill in the art of reselling, not in the mastery of any particular item or category.
TEA SOMMELIER TURNS LEAVES INTO MILLION-DOLLAR BUSINESS
NAME
LOCATION
OTTAWA, CANADA
STARTUP COSTS
$500
INCOME
$60,000 TO $80,000/MONTH
WEBSITE
A Canadian tea lover uses her formal training and entrepreneurial spirit to turn a new product line into a steeping success.
Sheena Brady had worked in the hospitality industry for many years, both in her native Canada and abroad. When a new luxury hotel in Toronto invited her to launch the most extensive tea program in the city, she looked forward to a new challenge.
Sheena was familiar with tea as a consumer, but she knew she needed more formal training. She took courses and tests, eventually earning the title of tea sommelier from the Tea and Herbal Association of Canada.
Running such an impressive tea program was rewarding, but it had its drawbacks. The required wardrobe had no room for interpretation: she had to show up in a suit, pantyhose, red lipstick, heels, hair in a bun, and beige or clear nail polish. For some people, a limited wardrobe and routine can help create focus and clarity—but for Sheena, it was constricting.
She needed more room to express herself, so she started creating her own tea blends after work. The entrepreneurial spirit kicked in. Before she knew it, she had developed an entire brand from the ground up. She got in touch with her tea leaf connections from the hotel, sent them her packaging design, and placed her first order. After a $500 investment, she was ready to launch Tease Tea.
The business was slow going at first. Sheena had an idea to make tea “sexy” with flirty names and descriptions, but it didn’t go over well. Lesson learned: Nobody wants sexy tea. They want tea that will make them feel good and will fit into their lifestyle.
She adjusted her marketing to focus on “prescribing tea for your every desire and goal.” Instead of trying to make tea bring sexy back, she was now recommending teas based on how the customer was feeling. For example, her Turmeric Tonic anti-inflammatory blend promised to boost a customer’s mood, while relaxing the mind and body. This customer-centric model was almost instantly more successful.
Still, there were challenges. A big portion of her expenses, especially in the beginning, was devoted to shipping. After nearly giving up because of high shipping costs, she realized she had two options to continue.
One, she could focus more on international orders. Because of some weird economics and tax issues, shipping across Canada could cost as much as $14, but shipping to any other country in the world could be done as cheaply as $8. It made financial sense to sell elsewhere.
Alternatively, she could try to raise the average order size. Shipping 50 grams of tea was just as expensive as 2 kilograms, so it made sense to encourage customers to order more.
One way she increased order size was by offering free shipping on orders of $50. Though Tease Tea takes a small hit by absorbing the cost, customers are far more likely to make larger orders, making that hit worthwhile.
She also began offering a larger portion of tea in a collectible tin at a slight discount, which gave people even more reason to add something else to their shopping cart. Customers who want a reusable and more attractive container are likely to purchase this option.
Sales grew as the months went by, and Sheena began to long for more time to work on Tease Tea. Though it felt scary, she decided to leave her job at the luxury hotel and accepted a different, part-time job that only takes two days out of her week. The job was with Shopify, the same company that was hosting her site. She credits them with providing support and mentorship that allowed her to take the business to another level.
Two years in, Sheena made Tease Tea available to consumers on Amazon. Growth has been extra-caffeinated ever since. Sales continue to climb, with average monthly revenue of between $60,000 and $80,000.
The Four Seasons Hotel chain began buying her teas exclusively. She was constantly invited to talk about tea on television and radio shows. She began donating a portion of sales to organizations around the world that empower women with skills and education.
Then it was time to take it another step further: a tea café in New York City. A landlord in Manhattan had an opening that was perfect for a small tea shop. Sheena signed a lease, and began the sprint to get the shop ready. She had only six weeks to open or the landlord would give the space to someone else.
Naturally, she hit the deadline. The main goal with the shop was not to sell directly, but to attract area tourists who would then go home and order online. And it worked. A few months later, Sheena launched a second pop-up shop in Manhattan.
Tease Tea recently crossed the $1 million all-time sales mark. Back when she started, it was hard to imagine that her side project would turn into such a thriving business, but that’s exactly what happened.
Keep an eye out at your local supermarket or gourmet grocery store. If it’s not there already, Tease Tea may show up on the shelves before too long.
“The secret to getting ahead is getting started. Too often we bog ourselves down with the granular details and problems that might not even exist or matter yet. Get messy, dive in, and tweak later, if necessary.” —Sheena
FUN FACT One time Sheena flew to California to open the tea program at the Four Seasons Hotel in Silicon Valley. Her checked baggage full of tea was detained by customs, and in her words, “The tea lady showed up without any tea.” After repeated phone calls and begging, she finally received her bags two hours before the event.
CRITICAL FACTOR
Sheena’s pursuit of tea excellence, combined with her background in the hospitality industry, led to a high-growth line of leaves.
SIDE HUSTLE LABS
Go Big or Go Home Choose to Stay Small
A side hustle can grow far beyond what the person who starts it ever imagines. In addition to the stories in this chapter, I regularly hear from many other people with multiple six-figure and seven-figure businesses that they started while working a regular job, and without spending a lot of money. Yes, it’s possible!
But it’s also just as interesting to choose not to scale. In addition to the people who “go big,” I hear from many others who are perfectly happy with their side gig being something they look forward to working on an hour or two each day, without stress or pressure. I also hear from people who speak of their side hustle as their creative outlet from a job that doesn’t utilize all their skills.
In other words, there is joy in staying small or in growing. Embrace this way of life, and make it your own.
For more, visit SideHustleSchool.com/grow.
*1 Jen also mentioned that she never understood the “risk” that everyone said she was taking in walking away from her job. As she saw it, remaining at the job would have been a much bigger risk.
*2 One of the most popular tours that Museum Hack offers is the consistently sold-out “badass bitches” tour—a feminist celebration of women in the Met.
*3 In other words, the company was paying $2,000 to acquire a driver who might only work for them once. It’s no surprise that this promotion was short-lived.
*4 He pays the people who clean his house, even if he doesn’t end up hiring them.
*5 Does all of this sound like a lot of work? Well, it is! And that’s the point. Think Maids stands out in large part because it emphasizes so much customer contact.
*6 Travis’s high school experience with design software was creative: he recalls using the programs to change his grades and show his parents a doctored report card.