Why Men Shouldn't File - A Case Study

Updated: Apr 29

On October 12, 2020, UpWork AI forwarded a notification to my email alerting me that a message was sent from somewhere in India. The subject line described the sender as a male over 40 years of age, supposedly tech savvy and fluent in English. My friend Alex in Miami has already encouraged me to get involved with Fintech so I decided to login and read the full message.

Here is the original in full:

"Hey Lubov!

I'm looking for a part time tax professional for our Fintech tax startup - FlyFin A.I.. I was wondering if you're comfortable handling consumer tax returns for freelancers (like yourself). its not corporate but rather 1040 Sch C, A, B, D, E, SE stuff. I'd like to invite you to take a look at the job I've posted. Please submit a proposal if you're available and interested.


I was in Brooklyn on 9/11/2001. It took me a few years to convince myself to even walk through where the Twin Towers used to be. Nineteen years after this Jaideep somehow found me online.

The job posting link is still active: https://www.upwork.com/jobs/~01500ae8f2ce5f9bb1. If it doesn't let you view it, here is a screenshot of the page:

Below is more information on how FlyFin obtained leads:

Jaideep then proceeded with a follow up phone call. He claimed that his startup already had 10,000 employees in India who are licensed Enrolled Agents. I looked up the IRS directory after his claim. There were less than 4,000 of them. According to Jaideep, he registered FlyFin in San Francisco but had to move back to India himself when COVID started. The call wasn't a Google Meet so I had no video or photo of this man except figuring out by his accent that he was not a native English speaker.

FlyFin's website is here: https://flyfin.tax/. The webpage has now been changed to claim that the software connects filers with Certified Public Accountants instead of Enrolled Agents. The page is a generic template anyone can utilize for free through Blogger or similar. Last I looked, FlyFin's mantra was "fly through taxes" and it didn't elicit any warm and fuzzy feelings at all.

If you come across Jaideep and his 10,000 co-workers, what you can do is report them for phishing here: phishing@irs.gov.

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