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How Career Coach Kyle Elliott Made His Team Big Business

At the end of 2013, Kyle Elliott, MPA, Ed.D., 30, was a full-time student at San Francisco State University.

He created a profile on freelance platform Fiverr, where he listed two services: LinkedIn profile resume writing and resume editing for $5 a gig.

(Elliott later added a third service, editing college personal statements for $5 a page.)

“The side hustle paid enough for a coffee and a Subway sandwich, but believe it or not, I wasn’t there for the money; I was driven by my love of helping people,” Elliott said.

Over the next two years, Elliott, who lives in Santa Barbara, Calif., found his $5 hustler quickly becoming a lucrative full-time career.

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 turned out to be a goldmine,” he added. “It was a powerful avenue for new business because people are often on LinkedIn looking for a new job, so it was natural to seek out a resume writer and career coach.”

From then on, the adage “Dad knows best” served him well. “As my dad advised, whenever I had a large waiting list, I would double my prices. Although the jumps seemed tiny at first, they increased dramatically over time, the biggest jump recently raising my fees from $250 to $500.

This covers a 50 minute virtual session, session notes and email support.

These premium awards are for technology executives earning between $250,000 and multi-digit annual salaries. “It helps me continue to give back to my community through regular speaking engagements for nonprofit and academic groups, as well as providing free job search content on my blog and other online publications. .”

Today, he’s the founder and career coach of CaffeinatedKyle.com, a boutique career coaching and interview service for senior executives and executives seeking employment in technology.

Kyle Elliott got his start on Fiverr writing LinkedIn profile summaries and editing resumes for $5 a gig.
Courtesy of Dr. Kyle Elliott

The website also houses a job search blog with the latest advice on how to find a new job in today’s competitive market.

Most of Elliott’s customers come from a steady stream of word-of-mouth referrals, even from those early Fiverr customers.

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.

“It was not ‘clients’ but ‘clients’ who chose me out of thousands of potential service providers, and I take that responsibility very seriously,” he said.

Elliott said current and former clients are your best source of future clients, so treat each project as if it were an audition for the next.

“Therefore, don’t be afraid to go the extra mile for your customers and create a one-of-a-kind experience they won’t find anywhere else,” he said. “This will not only result in powerful testimonials that will 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.”

In addition to more traditional freelance marketplaces like Fiverr, Upwork, and Freelancer.com, don’t overlook alternative marketplaces to grow your side business either.

“Craigslist is an underrated tool for finding side hustles,” he said. “During my undergraduate years, I landed a job as a personal assistant in college, earning $15 an hour, helping a professor fill out paperwork and pack his house for a cross-country move. “, Elliott said.

This rate was almost double the minimum wage at the time.

The Thumbtack home services platform is another you can use.

“You can communicate via 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 – solid options for scammers. “As I grew my business, I offered private English and writing lessons to supplement my income.”

(He did it via Craigslist and also advertised on social media.)

If you’re looking to quit your full-time job and continue your hustle at full throttle, or if you’re just curious about jumping into side-career land, Elliott has some helpful tips.


First, Elliott encourages people looking to start a side business to “do it because you have next to nothing to lose by trying” because the investment and barrier to entry for side businesses is so weak.

“You probably already have a market for your product or service with your friends, family and social media followers,” he added.

Be patient

Of course, this doesn’t happen overnight, so give it time if your idea doesn’t immediately gain traction.

“However, be open to pivoting if your brainchild doesn’t take off,” the career coach noted.

start small

For those with full-time careers, Elliott is the first to say that balancing work, more work and life can be difficult.

“Start with one client to see if you like running a side business,” he said. “As you find your rhythm and get used to balancing your full-time job with the added responsibilities of a side hustle, then you can consider taking on more clients gradually.”

Be transparent

It helps to be as honest with your boss as possible about your jostling, so there are no blurry lines.

“Fortunately, I have always worked for managers who supported my external projects. In fact, some of my former managers have since become great referral sources for new clients,” Elliott said.

Manage your time

As your side hustle grows, you’ll need to get creative in balancing it with your full-time job.

“It may feel like time for your side business in the early morning, during your lunch breaks, or after hours,” he said. “I also used vacation days and weekends to catch up on projects. It wasn’t easy, especially when my secondary agitation was really increasing, but I managed to make it work.


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