Matt Starky bid on more than 100 jobs before he landed his first gig on Freelancer, a big work platform that connects freelancers with clients. And, in many ways, his story is emblematic of how hard it can be to get started when working through broad-based freelance platforms.

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Sites like Upwork, Freelancer and Fiverr have hundreds of thousands of clients enlisting freelancers for a wide array of jobs every month, which makes them a fertile hunting ground for all types of remote work. But there are millions of freelancers from around the world vying for these positions. And, clients tend to hire either the people with the most experience and best ratings — or those who offer their services for the least amount of money. For newcomers, this can result in miserable pay and frustration.

But despite his rough start, Starky is now the top freelancer on the site, billing more than $2 million over the six years he’s used Freelancer as his primary job-search tool. And, while it’s not easy, he says anyone can make a good living working through these big sites. They need to be strategic and diligent.

“It’s actually easier than it seems,” says Starky, who has done everything from graphic design to software development.

His tips for freelance success?

Keep trying

Thomas Edison was famously quoted as saying that he hadn’t failed in more than 1,000 vain attempts to improve the light bulb. “I just found 1,000 ways that won’t work,” he said.

Starky’s rough start with Freelancer was similar. He bid on projects 12 hours a day for a solid two weeks before he landed his first $9 job. But he learned something with every bid. And, once he landed that first client, it became increasingly easy to get the next one, and hundreds of others after that, he says.

“The next project was $19; then $40 and now we work on projects that cost $1,000s of dollars,” he says.

Freelancers who have worked with Upwork say much the same thing. Early jobs are hard to get and often require discounting your normal rates. But once you’ve established a good reputation on the site, you get increasingly good gigs. (You can sign up with Upwork here.)

Measure and experiment

One of three things typically happen when you bid on a project — your bid gets rejected; it generates questions from the client; or it is accepted. To boost his acceptance rate, Starky started experimenting with different presentations to see which ones landed a conversation or a win. Naturally, when he found a formula that was successful, he’d incorporate that into future pitches.

To measure what was and wasn’t working, he created a Google Sheet with a number of cells. It had the project link or description, size/scope, his quote, his bid, special notes and results.

“Then, I’d measure what worked and didn’t work to try to double down on that,” he said.

He does the same with client communications, saving details of what he asked, how the client answered, and the outcome.

Find a way to stand out

One of the things Starky learned is that it’s far easier to win a bid when you have the opportunity to talk with the prospective client. But when there are hundreds of bidders, that’s easier said than done.

He chose a novel way to get the conversation started. He raised his rates, making him one of the most expensive contractors in his (then graphic design and advertising) field.

“Clients started reaching out to me asking why I was so expensive,” he says.

That allowed him to explain why he was the best person for the job.

To be sure, that gimmick might not work often — or for everyone. But when there’s lots of people bidding for a single job, it’s worth considering what makes your work unique. Do you have credentials; a signature style; references? Find something that makes you stand out and incorporate that into your pitch.


Getting conversations started helped land jobs. But fortunes on big job platforms hinge on ratings. And to get top ratings, your customers need to be impressed by what you deliver. Starky says his strategy here is simple. He gives them what they asked for and something more.

“They would ask for a logo and I would give them a tag line too,” he says. “They asked for a website and I would give them several designs.”

He also always asks clients for feedback and is responsive to any concerns they may have.

To be sure, it’s tough to justify going above and beyond when you’re earning a paltry amount on those early jobs. But it’s a great way to build repeat customers. Better yet, repeat customers often don’t require you to bid. So you’ll spend less time and are able to charge better rates on subsequent jobs.


Every bid has some common elements, such as an introduction that tells the client who you are and what you do. And, if you’re bidding in a particular niche — graphic design, for instance — it would likely include a variety of samples of your work.

Instead of reinventing that wheel for every bid, Starky created a series of templates that include all the standard stuff and a formula for customizing the rest. He maintains these on Clippy, a clipboard management app.

Then, when he bids a project, he picks up the template, modifies it for the new pitch and sends. It saves time and effort. And both matter when you’re bidding in a competitive marketplace.

Starky also has become an expert on using AI tools to simplify the work he does. He’ll sometimes have ChatGPT help write his bid, given the details of the project; and he’ll use graphic design tools to create art for advertisements and other creative projects. These tools can drastically reduce the amount of time a project requires, and that means you can work on more projects and make more money. To be sure, there’s a learning curve. But he’s launched a YouTube channel to help teach people how to use these tools. The videos are free.

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