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AI-Powered Mobile Tax App; Interview with Jaideep Singh, CEO and Co-Founder of FlyFin

AI-Powered Mobile Tax App

FlyFin is a new AI-powered mobile tax app for freelancers, creators, gig workers, and the self-employed. This fintech company plans to disrupt the market for individual tax preparation and filing, saving people thousands and eliminating nightmare scenarios on tax day. Jaideep Singh, CEO and Co-Founder of FlyFin will be sharing more information with us in this exclusive interview with TechBullion.

Please tell us a little more about yourself.

I’m Jaideep Singh, CEO and Co-Founder of FlyFin. Prior to FlyFin, I was an early adopter of AI, as I built Spock, the industry’s first and largest people search engine, indexing over 1 billion people representing 1.5 trillion data records. As both a VC and entrepreneur, I’ve focused on finding disruptive industry startups to invest in, creating more than $3B in value for companies. These disruptive companies have ranged from wireless LAN/Wi-Fi to AI Robotics for mining, construction and farming, to reinventing the marketplace globally for the electronic components supply-chain.

What is FlyFin and what unique services do you provide?

FlyFin is a new AI-powered mobile tax engine for freelancers, creators, self-employed and gig workers. This new AI tax engine helps them file their own taxes with simplicity, money savings, and peace of mind. It handles 95% of the work through smart AI and ML technology, then adds the human expertise of real CPAs who review and ensure 100% accuracy. FlyFin’s AI functionality matches perfectly for Gen Z and millennials, many of whom have jumped into the burgeoning creator or passion economies, hoping to build profitable businesses or side hustles.

What challenges were Tax filers facing before FlyFin and what specific solutions are you providing to mitigate these challenges?

It is often difficult for most tax filers, especially freelancers, to keep track of all of their tax preparation needs, including quarterly filings, regulatory IRS filings, and tracking all possible deductions. The IRS mandates self-employed individuals to file taxes quarterly and ignoring this can garner penalties up to 100% of the amount owed, yet more than 50% of freelancers ignore these requirements and find themselves owing large sums. Furthermore, calculating quarterly deductions and annual deductions can take over 20-30 hours of painstaking spreadsheet work, time that most freelancers don’t often have.    

FlyFin is a paradigm shift that takes five minutes to set up, as users can use the software’s AI to find potential deductions and then accept/reject possible expenses.  This takes 30 minutes to an hour at the most for freelancers over the course of a year. CPAs review all your work and file your state and federal returns, while guaranteeing their work with Full Audit Insurance bundled for free in the service .And because A.I. is working every day, users are always up to date with expenses, income, etc., meaning that they are ready to file 2021 taxes on Jan 1, 2022.  Just imagine that!  No more stressing about “April 15th!”   

“It’s a game changer” is the feedback I hear most frequently from users.  

The Artificial Intelligence market is booming and could be found in almost all industries. What makes AI special in this project and how does Machine Learning actually work in Tax filing?

The AI/ML problem is very specific for this industry.  As is the case for every industry, it requires extensive use of natural language processing, but not broadly for the English language.  The problem is more specific to tax and accounting language and the way merchants and products are named and what they mean. The machine learns by taking input and signals from our expert CPA team and from our users.  There is machine learning at the aggregate, cluster, and individual levels.  

Could you give us a walkthrough of the FlyFin mobile app ecosystem and how it works to maximize savings?

FlyFin is a tax service where the main interface for the users is a mobile app.  To get started, users download the app and link their account statements to make tracking expenses effortless. From there, FlyFin’s A.I. engine automatically scans expense accounts 24/7, 365 days of the year to monitor and suggest which expenses are deductions. FlyFin’s A.I. coupled with professional CPAs’ oversight, find all possible tax deductions accurately and make sure there are no mistakes. With our standarding pricing option, users also have unlimited access to the domain expertise of tax CPAs, who review each individual’s tax information and provide expert help to maximize savings. Users have the option to file their taxes with FlyFin’s CPAs, who ensure 100% accurate tax review and preparation, or can export their data in an IRS-ready format. 

How does the FlyFin app guarantee accurate quarterly tax payments and what are the benefits for Tax filers?

We’ve found that 95% of freelancers overpay their taxes, as most freelancers don’t consider tax deductions while estimating quarterly taxes. Many times users take deductions that are not really deductions and most times they forget a lot of possible ones, which leads to either overpayments or penalties. With FlyFin’s tax engine, the AI automatically finds every deduction, which lets users review them while the expenses are incurred. If users are unsure, they just “swipe up” to get CPA help. To guarantee the AI’s assessment, we offer a real CPA to review the deductions and tax submission prior to filing tax returns.

Why should freelancers and Tax filers trust the FlyFin App, what measures do you have in place for data security?

That’s the beauty of our design. With highly qualified, expert CPA oversight freelancers can always rest assured that everything is being done correctly, as this is what the wealthiest of tax filers do.  Secondly, FlyFin guarantees its work through “Full Audit Insurance,” which is bundled for free for tax filers.

Tell us more about the brains behind this company, what motivates  you and what makes you special for this project?

We started this company because we all just simply “hate doing taxes” and the whole process “sucks!” Most years, I end up filing for an extension because It is such a horrific pain for tax filers who have complex taxes e.g. all self-employed freelancers. There are too many things to remember.  

As a computer scientist and experienced AI expert, I realized that this is a great application of AI.  I also recognized the limitations of AI and then realized that combining it with the best human minds (highly experienced CPAs) would prove to be the most accurate solution.  We love seeing the products and features we are creating being cherished by our users and we get amazing feedback and comments from them. This is what provides all the motivation and passion that we need at FlyFin. 

Do you have any available opportunities for partnerships and investors at FlyFin?

We have abundant partnership opportunities and have just brought on a very experienced VP of Partnerships to the company.

For more information, visit the website:

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