Painless1099 was a financial service platform specifically designed for the freelance and self-employed workforce in the United States. Its core mission was to simplify tax obligations for 1099 workers by providing them with a smart, FDIC-insured bank account that automatically withholds a user-designated percentage of every payment for taxes. When a freelancer's client deposited money into their Painless1099 account, the service would instantly set aside the tax portion into a separate savings bucket and transfer the remaining income to the user's primary checking account. In March 2021, Painless1099 was acquired by Lili, a larger digital banking platform for freelancers, and its features and user base have since been integrated into the Lili product suite.