Painless1099

Painless1099, founded in 2015 by Ace Callwood and Matthew Russo, operates within the financial software industry, specifically targeting the growing freelance and gig economy workforce. The company was established to address a critical pain point for independent contractors: managing the financial complexities that come with self-employment. Callwood, the CEO, previously founded Coffitivity and served as an Entrepreneur in Residence at Virginia Commonwealth University, bringing experience in building products for niche audiences. Russo, the Product Architect, also contributed to Coffitivity and has a background in iOS development, which directly informed the creation of the company's core product.

The business provides a smart bank account designed to automate financial administration for freelancers. Its primary service revolves around simplifying tax obligations by automatically withholding a percentage of a user's income for tax payments. This core feature ensures that independent contractors are prepared for tax season without needing to perform manual calculations. The platform extends beyond tax management, offering an integrated hub for self-employment benefits. Users can automate payments for health insurance, establish and contribute to a SEP IRA for retirement savings, and allocate funds to a 'rainy day' account. This suite of services effectively mimics the financial safety net typically associated with traditional W2 employment, while allowing freelancers to maintain their professional autonomy.

Painless1099 operates on a B2C model, directly serving individual freelancers, consultants, and gig economy workers. The company positioned itself in the FinTech and sharing economy markets. Over its active years, the company successfully raised approximately $600K to $786K in funding through a series of seed rounds and grants from investors including Techstars, Kapor Capital, and Village Capital. According to PitchBook, the company ceased operations in March 2024.

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