[1] The software also provided means to organize and categorize expenses for filing a United States Schedule C tax return.

[5] Kevin Reeth and Ben Curren worked together at Intuit in 2006 and then later at a web-application firm called Esomnie LLC.

[citation needed] Curren and Reeth had become increasingly frustrated with the complexity of doing taxes for small businesses, so in 2008 they founded a company and website called BootStrap.

[6][7][8] The Website was renamed Outright just a few months after launch, though it continues to be operated by BootStrap, Inc.[9] In 2009, the company raised a total of $7.7 million funding from Sequoia Capital, First Round Capital, Shasta Ventures and SoftTech VC among others.

[7][10][11] Today, the website manages $1.2 billion in transactions from small businesses and independent contractors.