tHesE Guys cAn kicKsTart aNy sidE hustLe

These Guys Can Kickstart Any Side HustLe

Luckbox sits down with Nick Loper and Chris Guillebeau, two side-hustle proponents who made side hustling their main gig.

By Ed McKinley

Chris Guillebeau

Two side-hustle gurus side hustled their way into the full-time side-hustle business. Chris Guillebeau began by blogging part-time about money-making sidelines for travelers, and Nick Loper started with a part-time comparison-shopping website for shoes.

After those humble beginnings, both went on to learn the nuances of side hustles and then began sharing that wisdom. Now, their books convert legions to the side-hustle movement, their websites attract millions of monthly visitors and their podcasts have been downloaded millions of times.

So what do they have to say? Loper and Guillebeau agree the average person can develop a profitable side hustle to augment the income from a day job. Virtually everyone possesses a sometimes-hidden skill or talent that could develop into a marketable product or service. Just add strong motivation, a serious attitude and a robust work ethic. Precise timing can help, too.

Both experts hesitate to calculate the mathematical probability of side-hustle success, but they note that nearly half the population is already pursuing a second income or will soon try. Many of those side hustlers will achieve their goals, the two side-hustle pros conclude. “The odds of success are pretty good, depending on what you decide to do,” Guillebeau says of beginning side hustlers.

Loper cites valuable side-hustle personality traits, such as persistence, stubbornness, resilience and a willingness to figure something out on the fly instead of beforehand. Beyond that, side hustlers who succeed generally have one of two answers to the question of why they’re hungry for a part-time gig, he says. They either want more from life than their regular job provides, or they simply need the money.

Side-hustle advice Side hustlers should choose a secondary gig that fits their skills or knowledge, Guillebeau advises. Everyone’s an expert at something, often without even realizing it, he says. Discovering a hidden expertise or latent talent can require a “self-interview” or consulting with friends, he contends. But he’s confident he can usually detect someone’s natural-but-marketable side-hustle skill in a three-minute conversation.

Guillebeau’s advice doesn’t end there. Be practical instead of purely aspirational, he admonishes. “Don’t follow your passion—follow your skill,” he says. “You may like to play golf, but you don’t necessarily want to get into the golf business.”

Nick Loper

Loper agrees. “You become passionate by doing the work,” he says, providing the examples of his own forays into house painting and podcasting. He didn’t care how houses looked before he started painting them as a college student, but he soon caught himself critically eyeing the eves of every home he passed. In much the same way, his initial indifference to podcasting grew into an emotional attachment that’s now a central part of his life. Yet even when capitalizing on a personal strength, fledgling side hustlers should prepare for setbacks,

“don’T folLow yoUr paSsioN— fOllow yOur skilL.”

—Chris Guillebeau, on choosing a side hustle

Side-hustle expert Chris Guillebeau

Loper cautions. “It’s always going to be harder than you think,” he says. “But that makes it worthwhile. If it were easy, everybody would be doing it.” He notes that it’s less challenging to choose a “plug and play” gig with Lyft than to come up with a unique side hustle.

Whatever gig one picks, side hustles don’t necessarily last a lifetime. “Choosing what’s next doesn’t mean choosing what’s forever,” Loper says. Even someone who doesn’t want to be painting houses at age 50 might do well to consider seizing that opportunity for the moment. In any case, choose a hustle and do it, he urges, because the best opportunities often appear to side hustlers who are already in motion. “You have to look at it as an experiment,” Loper says of the early stages of a side hustles. “Until you try it, you never really know,” he contends. Start small with the understanding a particular gig may not work but something else could succeed later. But that nonchalance doesn’t equate to turning off the brain. Side hustlers should remember that the public tends to seek one of two results from a product or service— entertainment or the solution to a problem.

Notable side hustles Some wacky-sounding side hustles work well, Guillebeau says. He tells the tale of a short-order cook who liked to break the monotony of his job in a diner by creating smiley faces on pancakes. The cook began offering his edible art at catered events—like birthdays and weddings—and it became so popular he found himself traveling the world to enliven parties everywhere from New York to Dubai. These days, he controls a lucrative pancake-decorating business and has attracted 300,000 Instagram followers.

In another example, a Korean-American founded a successful business that offers a subscription box for Korean face masks that act as overnight moisturizers, Guillebeau says. In yet another, a mother of twins who was frustrated with commercially available hairbrushes invented a better one and—with low startup costs and without much experience—turned it into a seven-figure business.

Loper has stories, too. “I’m always amazed at what people come up with,” he says of the ideas he encounters. He recalls a college student, Chris Schwab, who started a house-cleaning business called Think Maids without ever picking up a mop or a broom. Instead, the enterprising American University undergrad hired people to do the work and spent his time on marketing and on heading off scheduling snafus, making sure phone calls were returned, and fixing or avoiding other customer-service headaches. At the 90-day milestone, his business was pulling in $20,000 a month. “Overall, I spend maybe 10 minutes a day running Think Maids now,” he said.

One entrepreneur, who wishes to remain anonymous because his hustle is nearly free of barriers to entry, regu larly scores $100 an hour on Saturday mornings by picking up dog droppings. The pro scooper determines the price based on the size of the yard and number of dogs in the home.

Another budding businessperson didn’t have access to enough capital to become a real estate investor, but he had enough cash to buy trampoline-like “bounce houses” for children’s parties. He rented them out for enough to make a profit.

“It’s AlwayS gOing to Be harDer than yOu tHinK.”

—Nick Loper, on starting a side hustle

Side-Hustle Philosophy

Driving for Uber can teach the lesson that income doesn’t have to derive from a full-time job, according to side-hustle expert Nick Loper. But the best side hustles, he says, don’t come courtesy of some outside employer—they come from within.

Loper also cites the case of Chris Green, who sells T-shirt designs through Merch by Amazon, an invitation-based platform that pays designers royalties. Anyone interested in joining should apply, Green advises. Royalties vary but on a standard $19.99 T-shirt he collects a $5.23 royalty. The beauty of the site is that designers don’t have to carry inventory or incur any other expenses—they only make money. “It really is a too-good-to-be-true kind of thing,” Green claims.

In another memorable side-hustle story, Loper describes the journey of Brian Schooley. When Schooley heard about the possibility of becoming a mobile notary, he was working both a full-time and a parttime job. Two-and-a-half years later, Schooley now plans to take his side hustle full-time. “Really anybody could do it,” he says. “If you just learn about the documents, it’s pretty easy to become a notary.” In California he had to take a six-hour course, pass a 30-question state exam and purchase insurance. In the last month, he made $6,000.

What side-hustling requires Side-hustle entrepreneurs reach inside themselves to find their own gigs instead of signing on to work for someone else, says Guillebeau. By that definition, Uber, Lyft and other part-time jobs don’t qualify as side hustles. He characterizes side hustles as “more next level” than that. “A side hustle is an asset you’re creating for yourself—something that’s going to build security for the future, help you get ahead or pay off significant debt,” he maintains.

Loper, on the other hand, views driving for a ride-sharing service as a valid side hustle that can teach something fundamental—the lesson that income can flow from sources other than a full-time job. Still, the best side hustles don’t result from Googling a list and randomly picking No. 37. The best come from within, he says, agreeing at least in part with Guillebeau.

Wherever the inspiration arises, side hustles need not break the bank. “You’re not going to spend your life savings,” says Guillebeau. One factor that helps hold down costs is that would-be entrepreneurs often know within 30 days or so if a side hustle shows the potential to succeed.

Regulation, licensing and other red tape shouldn’t stand in the way of starting a side hustle, Guillebeau contends. Those factors become important only after a side hustle is well underway and turning a profit, he says.

Earning $500 a month part-time defines side-hustle success in Guillebeau’ eyes. Though he admits the figure’s a bit arbitrary, he notes that it could make a car payment or whittle away at a student loan. After reaching that $500 mark, it’s usually not that difficult to progress to $1,000 monthly, he says, adding that a little more effort can bring in $2,000 each month.

Whatever the amount of cash flowing into the coffers, it’s important to begin with an actionable goal, such as making $50 a day with a side hustle, Loper recommends. That provides a way of measuring success.

But however one measures success, the side-hustle gurus are convinced of at least one thing. Their extensive research and their nearly countless interviews with side hustlers of every stripe have led them to believe deeply that almost anyone who’s motivated and capitalizes on established knowledge or skill should pick a gig and take a shot. “Go for it,” they would agree.

From Side Hustlers to CEOs

Entrepreneurs can get a daily dose of actionable advice from Bootstrapping in America, a 20-minute interview show on the tastytrade online financial network. The program’s guests describe the adventures and misadventures they experienced starting their own companies. Interviewers include tastytrade co-CEO Kristi Ross, a serial entrepreneur who’s recognized nationally for mentoring, advising and investing in early-stage businesses. The show starts at 10:10 a.m. Central time, Monday through Friday. Most of the show’s 2,000 episodes are archived on the tastytrade website.

Side Hustle: From Idea to Income in 27 days

By Chris Guillebeau (BOOK EXCERPTS)

5 Things You Don’t Need to Begin A Side Gig

• You don’t need much money. Put away your credit cards (at least the ones with high limits) and don’t worry about needing to raise capital or ask someone for a loan. In some cases, no money at all is required. • You don’t need much time. The time required to start a hustle should be minimal and take no more than one hour a day. • You don’t need a business degree or specialized education. You’re starting your own business, not running someone else’s. You won’t need complicated software or spreadsheets. Write financial forecasts on the back of a napkin. • You don’t need employees, assistants or business partners. You may want to get help at some point, but not right away. The initial goal is to start on your own, using your own skills and effort. • You don’t need experience starting a business. You don’t need to be an “entrepreneur” to start a side hustle.

Key Criteria Checklist

1. Is your idea feasible? Your goal is to start a project in a short period of time that earns money outside your day job. Can you envision your next steps? If not, abandon the idea.

2. Is your idea profitable? You’re not looking for an idea that merely sounds interesting, you’re looking for a profitable one. A side hustle is something that makes you money, not costs you money. If you don’t see how you could make money from the idea, preferably in a short amount of time, it’s probably not a good idea.

3. Is your idea persuasive? Your idea has to arrive at the right time and be so persuasive that it’s hard for customers to say no—you want the right idea at the right time.

10 Steps to Getting Started

1. Get a separate bank account that’s just for your side hustle.

2. Similarly, get a separate credit or debit card you use only for expenses associated with your hustle. Bonus tip: make sure you’re earning airline miles!

3. Pay for everything you can up front. You’ll operate lean and worry far less if you don’t owe money to anyone.

4. Set aside at least 25% of your hustle income for your annual or quarterly donations to the government.

5. Be fast with invoicing. Don’t save invoicing for one day at the end of the month. When you do the work or make the sale, send the bill.

6. Insist on a written agreement for service work—basic terms in writing to avoid misunderstandings.

7. Legal structure: operating as a sole proprietor is perfectly acceptable for many hustles. If you need to incorporate your hustle, you can often do that yourself online for much less than it would cost to hire an attorney.

8. From the beginning, set up a simple accounting system. This should be cheap or free and can grow with you.

9. Set aside a dedicated hustle workspace, even a small one, in your home. If that’s not possible, create a mobile one. For example, if you like to work at a coffee shop, go to the same one at the same time, and try to work from the same table. The idea is to create a pattern and a routine that will make it easier to work on the hustle consistently.

10. Pay yourself first. Set up a system to transfer profits from your hustle account to your personal account on a regular basis. Don’t have it set to transfer continuously as sales come in (that can be difficult to track later), but withdraw at least some profits on a regular basis. Getting paid is empowering!

Side-hustle expert Chris Guillebeau

1,028 podcasts to date

Resource websites: chrisguillebeau.com and sidehustleschool.com

Books include: The Art of Nonconformity, The $100 Startup and Side Hustle: From Idea to Income in 27 Days