In 2001 Jain was involved in a scandal when ICQ instant messaging logs between him and other employees were leaked onto the internet.
On April 20, 2005, he was ordered to pay $3.1 million to Symantec for selling counterfeit software and violating intellectual property laws.
Jain operated several Internet-based companies including Discount Bob, Shifting Currents Financials, Inc., Innovative Marketing Inc., Professional Management Consulting Inc. and Shopenter.com, LLC.
In December 2008, Jain was listed as a defendant in the Federal Trade Commission's case against so-called "scareware" applications such as WinFixer.
In mid-December 2008 U.S. District Judge Richard D. Bennett fined Innovative Marketing $8,000 for each day that it continues to sell bogus scareware software on its website.