Can Taxes Really Be Stress-free for Freelancers? New Fintech Says Yes!

When we talk about the fintech industry, we’re often focused on highly disruptive technology firms taking on large institutions such as banking, loans, and credit. But one financial area we tend to overlook in fintech is taxes.

And perhaps no one needs more help with their taxes than freelancers.

The Great Resignation—where more than 4 million Americans left their jobs in August 2021—has inspired a new wave of freelancers, many for the first time in their career. According to a recent report from Upwork, a platform connecting businesses and freelancers, 59 million Americans performed some form of freelance work in 2021, equivalent to more than 1/3 of the total workforce. This represents a six percent increase in self-employment over the previous year, generating a $1.3 trillion in economic impact.

With so many new freelancers, it’s probably no surprise that many aren’t familiar with the ins and outs of taxes, making this week’s discussion on Fintech Growth Talk a timely one. Jaideep Singh is the founder of FlyFin, an AI tax engine designed for freelancers.

Like the freelancers it serves, FlyFin is a product of the pandemic, hailing from Singh’s own pain points around collecting the data needed to file taxes. “I realized this is a beautiful sort of problem,” says Singh. “We can apply artificial intelligence, especially machine learning and natural language processing, to really automate a lot of the work.”

The result is a product that eliminates as much as 95 percent of the work associated with recording and categorizing business expenses for tax deductions, according to Singh. The app imports all the transactions from a freelancer’s accounts and then allows them to swipe right to itemize an expense or left to skip it.

But it’s not only about automation and machine learning. Singh recognized early on that human intelligence is often needed to properly categorize expenses. That’s why users can swipe up on an expense to get clarification from a CPA. What’s more, FlyFin’s CPAs are available for other questions and to help filing taxes. Ultimately, this can help freelancers prepare to file their taxes sooner and with far less pain.

Singh’s vision is to help freelancers—and potentially other businesses down the road—save significant amounts of money on their taxes. “We’re finding that on average are freelancers using [our] platinum [subscription], are leaving at least four or $5,000 on the table,” says Singh. This often comes from freelancers not knowing that they can take deductions for things like the workspace in their home, computers and other equipment, and even clothing or jewelry in some cases.

Ultimately, Singh believes that FlyFin will dramatically reduce the amount of stress freelancers go through when organizing and filing taxes. The key, says Singh, is keeping things as simple as possible for users, ensuring they get the right level of help when they need it throughout the year, rather than waiting until Tax Day to get it.

About Jaideep Singh

Jaideep is the CEO and Co-Founder of FlyFin, a new AI-powered mobile tax engine/app for freelancers, creators, gig workers, and the self-employed. Jaideep was an early adopter of AI as he built Spock, the industry’s first people search engine, indexing over 1 billion people representing 1.5 trillion data records. As both a VC and entrepreneur, he has focused on finding disruptive industry startups to invest in and has created more than $3B in value for companies, ranging from wireless LAN/Wi-Fi to AI Robotics for mining, construction & farming to reinventing the sales in the electronic components market.

Follow Jaideep on LinkedIn. 

Listen to our full interview with Jaideep Singh here.


Christina Trampota
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