Taxes may not be the first thing on a person’s mind when he or she decides to work through an Internet-enabled, on-demand platform such as Postmates or Door Dash. But come tax time, those working as independent contractors will realize how complicated things can be if they are not set up right.

Even finding the right information also presents a challenge with conflicting recommendations on the web.

It’s a tricky landscape for on-demand workers whose main jobs don’t involve preparing taxes — and they’re leaving money on the table at an average amount of $1,200 per year. But that is where Keeper Tax comes in. The San Francisco-based firm uses machine learning to help on-demand workers save money on taxes. Workers sign up online and link their credit cards and bank accounts to the site, which automatically examines them to identify tax write-offs. It also enables the workers to file taxes online through the platform.

Think Turbo Tax for anyone who doesn’t describe themselves as a business owner but who does earn money as a 1099.

In September, Keeper Tax tied as a top winner in a Shark Tank-styled competition for best business case at SIA’s Collaboration in the Gig Economy conference in San Diego. It was one of five finalists chosen from a field of 20 to make presentations at the conference. Tying with Keeper Tax was AppJobs.

Unaddressed Market

Keeper Tax founder and CEO Paul Koullick worked with the gig economy population before he began the company as a project manager at Stride health, a firm that offers health insurance for gig workers. It’s also where he realized how big the problem was.

“More than anything, I felt like it was something that was so remarkably unaddressed, the problem being these people all overpay on taxes,” Koullick says. “I knew these Uber drivers and these other middle-income workers were just massively overpaying, and on top of that, living from paycheck to paycheck a lot of the time.”

And even diligent gig economy workers would have difficulty figuring out what to write off and what not to.

“It’s not even that they should know better and they should go and download an app and make sure they are taking cover of it,” Koullick says. “You could spend a big chunk of time doing your own research and still not feel you have a grasp of the situation.”

There are numerous expense-tracking applications, but they typically treat independent contractors as small business owners who have a fair amount of expertise on taxes and tracking expenses. But Koullick says that’s not fair when it comes to independent contractors working in the gig economy.

“That’s really not what people sign up for when they get a job that happens to pay on 1099,” he says.

Clarifying Matters

There’s also confusion for those handling taxes on their own. For example, some sources will say a phone bill is a write-off, while some will say it’s not.

Car washes are a common question. Koulick says accountants have told Uber drivers for years that their car washes were not write-offs. However, Keeper Tax made a stand and did research to show that car washes for Uber drivers should be a write-off given they need clean cars to keep their customers happy. He says Keeper Tax aimed to think things through rather than taking the easy, conservative way out, he says.

Bridging the Gap

But it’s about bridging that gap between gig economy workers that don’t know much about taxes and the necessary expertise that is behind Keeper Tax.

Over the past nine months, the company has been growing 20% to 30% monthly, Koullick says. It has also saved on-demand workers some $40 million.

One of the challenges in building Keeper Tax was putting the mechanisms in place to analyze the taxes. “There’s a lot of infrastructural plumbing that needs to be done to do what we do,” he says.

The core of the service is automatically scanning bank and credit card transactions for the whole year and suggesting things that are tax write-offs. It’s easy to describe but hard to implement.

It also works with all types of gig economy workers, presenting a technical challenge in providing the service to all types of workers.

Future Plans

The next step for Keeper Tax is growing its tax filing business, Koullick says. People often come to the company through the tax season as a way to find write-offs automatically. However, Keeper Tax is also an IRS e-file partner.

In the end, Koullick says he hopes to see gig economy workers “transformed from people who are barely scraping by, barely able to pay their tax bill at the end of the year to folks who have a good handle on it and know all the best ways to minimize their tax bill.”

The event judges were Thomas Jajeh, CEO and founder of twago; Jody Miller, co-founder and CEO of Business Talent Group; Gary Swart, general partner of Polaris Partners; and Fabio Rosati, executive chairman at Snag.