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Painless1099, LLC

March 9, 2016: ACe Callwood, CEO

     Navigating self-employment taxes is consistently cited as one of the top issues an independent contractor faces every year. More specifically, for many of the 53 million Americans earning 1099 income, saving money for taxes is difficult, which often results in an unexpected (and unmanageable) bill from the IRS. 

     Painless1099 helps these individuals (think: Uber drivers, freelance designers, and real estate agents) set cash aside for tax season. Members receive a FDIC insured "smart" savings account that automatically separates taxes from income deposits. As a pass-through account, Painless1099 keeps just enough in the user's "withholding account" for taxes and automatically sends the remaining cash to their personal checking account. This allows freelancers to focus more time on working, getting paid, and spending money knowing that Painless1099 simplifies the process of saving and helps avoid an emergency during tax season. 

     Painless1099's primary revenue opportunity is to charge users at key touch points, namely remitting estimated quarterly tax payments to the IRS. Beyond that, Painless is primed to offer ancillary products and services around the primary accounts users will open. As acquisition costs for financial institutions continues to skyrocket, Painless1099 provides an attractive funnel for banks focused on new relationships with a traditionally hard to reach demographic like the 1099 economy. Splitting the difference in acquisition of an active banking relationship with a large retail bank makes for an even more attractive model.
     The Painless team and advisors are former freelancers and financial experts who understand the rapidly growing, but historically underserved, 1099 workforce. With several enterprise partnerships in place, the team plans to use current funding to optimize user experience and hit acquisition milestones throughout the year.  Visit for more information.


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