Jaime Hollander will never forget the day she stood in her apartment-building lobby holding her first freelance check for $20.
"It was so exhilarating," she told Insider. "I suddenly felt like there was this journey for me in freelance, that this was something I could do."
Hollander had googled "freelance for copywriters" while pregnant and bedridden in 2012. She was looking for work that she could do from home during her maternity leave that tapped her copywriting and marketing skills. She found a couple of work-for-hire platforms and landed her first project on Upwork within five days of setting up her profile.
After having her baby and returning to her job at Better Homes and Gardens, she continued doing freelance gigs on nights and weekends. By the end of the same year, she earned $26,000 on top of her full-time salary, she said.
In 2020, after 17 years working for media companies such as Condé Nast, Meredith Corp., and Time Out, Hollander quit her job and took her freelance side hustle full time. She established her own marketing agency, RRDA, and has worked with more than 400 clients, including Adobe, Johnson and Johnson, Twitter, and Nestlé.
Hollander now has three employees and has earned more than $1.5 million since 2012, according to her Upwork profile. Meanwhile, her company generated more than $784,000 last year in revenue, which Insider verified with documentation. She gave her tips for starting a successful freelance business.
Price to get jobs, then scale
Today, Hollander charges up to $250 an hour for freelance projects, but it took time to build up to those rates. When she started, she charged between $10 and $15 an hour and took on up to 55 clients at a time. As she maximized her capacity, she added $5 to $10 to her rates.
She recommends freelancers start with low rates to get hired, do the job well, and get a review. Then, over time, you can raise your prices as you build up your reputation on the platform.
"You're not committing to staying at that rate forever," she said.
Now, she tends to have fewer clients at a time, but more of the projects are long term. She hires other freelancers to broaden her offerings, including experts in search-engine optimization, illustrators, and designers.
Stay in your lane to become a trusted expert
Hollander stuck with copywriting for a while before branching out into other marketing services, which allowed her to deliver high-quality work quickly, she said.
"I do recommend staying in your general lane, especially in the beginning," she added.
Having a focus also helped establish her as an expert. As she grew clients' trust, she eventually opened up her services to include brand consulting, email marketing, and business proposals.
While Upwork remains a significant source of her business, she also gets word-of-mouth referrals and has tapped into her connections from previous jobs.
"Having that network as the agency has grown has been really helpful, but I don't think it's necessary to getting started on a freelance journey," she said.
'Success breeds success'
On any work-for-hire platform, reviews are the key to gaining more clients.
"You're an unproven entity," Hollander said. "When starting, you've got your background, but what really matters is the quality of work that you're delivering and the reviews and ratings you're getting."
While she had nearly a decade of experience before starting her freelance business, she said it took her a while to build momentum.
"Sometimes people don't want to hear that this is my 10th year and then before that I had another 10 years," she said.
Today, Hollander can't remember the last time she applied for a freelance gig because clients now come to her.
"Success breeds success," she said. "As you start getting these amazing portfolio pieces, more things come."
