At the end of 2013, Kyle Elliott, MPA, Ed.D., 30, was a full-time student at San Francisco State University.
He set up a profile on the freelancing platform Fiverr, where he listed two services: writing LinkedIn profile summaries and reviewing résumés for $5 per gig.
(Later on, Elliott added a third service, editing college personal statements for $5 a page.)
“The side hustle paid enough for a coffee and Subway sandwich, but believe it or not, I wasn’t in it for the money; I was motivated by my love of helping people,” said Elliott.
Over the next two years, Elliott, who lives in Santa Barbara, Calif., found his $5 side hustle was quickly becoming a lucrative full-time career path.
With two years of experience under his belt, he decided to market his coaching services on Craigslist, Facebook and LinkedIn.
“Around the same time, a friend introduced me to the LinkedIn ProFinder freelancer platform connecting service providers with clients, which proved a gold mine,” he added. “This was a powerful avenue for new business as people are often on LinkedIn to look for a new job, so it was natural to search for a résumé writer and career coach.”
From that point, the adage “Dad knows best” served him well. “As my father advised, any time I had a significant waitlist, I doubled my prices. While the jumps felt minute at first, they’ve grown significantly over time, with the most recent leap taking my fees from $250 to $500.”
This covers a 50-minute virtual session, session notes and email support.
Those premium prices are for tech executives making between $250,000 and multi-seven-figure annual salaries. “Doing so helps me continue giving back to my community through regular speaking engagements for nonprofit and university groups, as well as providing free job-search content on my blog and other online publications.”
Today, he’s the founder and career coach behind CaffeinatedKyle.com, a boutique career and interview coaching service for senior managers and executives looking to find a tech job.
The website is also home to a job-search blog with the latest tips on how to find a new job in today’s competitive market.
Most of Elliott’s clients come through a steady stream of word-of-mouth referrals, even from those first Fiverr clients.
Elliott stressed the importance of being intentional with the words he uses to describe his services and the people who choose to work with him.
“They’re not ‘customers’ but ‘clients’ who have chosen me out of thousands of potential service providers, and I take that responsibility very seriously,” he said.
Elliott said that current and former clients are your best source of future clients, so treat each project like it’s an audition for the next one.
“Consequently, don’t be afraid to go the extra mile for your clients and create a one-of-a-kind experience they cannot find anywhere else,” he said. “Doing so will not only result in powerful testimonials that help you stand out in the crowded marketplace, but will also result in referrals, which are now responsible for the vast majority of my new business.”
Along with the more mainstream freelance marketplaces like Fiverr, Upwork and Freelancer.com, don’t overlook alternative marketplaces for growing your side hustle, either.
“Craigslist is an underrated tool for finding side hustles,” he said. “While in my undergraduate years, I landed a gig as a personal assistant in college earning $15 per hour helping a professor complete paperwork and pack their house for a cross-country move,” said Elliott.
That rate was almost double the minimum wage at the time.
Home services platform Thumbtack is another one you can use.
“You can communicate through the platform itself, rather than email, which reduces some of the risks associated with working with strangers,” he said.
Elliott calls tutoring platforms — Wyzant, Tutor.com and TutorMe, to name a few — strong options for side-hustlers. “As I grew my business, I offered English and writing tutoring to supplement my income.”
(He did so via Craigslist and also advertised on social media.)
If you’re looking to leave your full-time gig and pursue your side hustle at full-throttle, or simply curious to dabble into the land of sideline careers, Elliott has some helpful advice.
Give it a go
First and foremost, Elliott encourages individuals looking to start a side business to “do it, as you have virtually nothing to lose by giving it a try,” since both the investment and the barrier to entry for side businesses are so low.
“You likely also already have a market for your product or service with your friends, family and social media followers,” he added.
Be patient
Of course, it doesn’t happen overnight, so give things time if your idea doesn’t immediately gain tons of traction.
“However, be open to pivoting if your original idea doesn’t take off,” the career coach noted.
Start small
For those with a full-time career, Elliott is the first to say that balancing work, more work and life can be difficult.
“Start with just a single client to see if you like running a side hustle,” he said. “As you find your groove and get used to balancing your full-time job with the additional responsibilities of a side hustle, you can then consider slowly taking on more clients.”
Be transparent
It’s helpful to be as honest as possible with your boss about your side hustle, so there are no blurred lines.
“Thankfully, I’ve always worked for managers that were supportive of my outside endeavors. In fact, some of my former managers have since turned into great referral sources for new clients,” said Elliott.
Manage your time
As your side hustle grows, you’ll have to get creative as you balance it with your full-time job.
“This may look like carving out time for your side hustle in the early morning, on your lunch breaks, or after hours,” he said. “I also used vacation days and weekends to catch up on projects. It wasn’t easy, particularly when my side hustle was really growing, but I made it work.”