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Expensify was founded in 2008 by current CEO David Barrett. Barrett, a native of Saginaw, Michigan, and a graduate of the University of Michigan, began programming at the age of six. He was involved in numerous tech companies prior to Expensify, including Red Swoosh.
The company has completed several rounds of venture capital funding, raising $1 million in 2009, $5.7 million in 2010, $3.5 million in 2014, and $17 million in 2015.
The company, which expanded its operation in Michigan in 2014, partnered with Gogebic Community College to offer scholarships to students in the area. In July 2015, CEO David Barrett addressed the United States Congress on behalf of the app industry, speaking to a House, Health, and Technology subcommittee.
In November 2017, the company faced allegations of exposing some customers' personal information to contractors manually entering receipts through Amazon's Mechanical Turk service. Expensify acknowledged that a bug allowed fewer than 200 receipts to be visible to certain company contractors using Mechanical Turk to test a new feature under development. The company halted the test.
The company went public on 11 November 2021 under the ticker EXFY. The company's stock has decreased more than 95% since its IPO.
In 2023, Expensify funded an update and renovation of Portland's oldest food cart pod, located next to their Portland headquarters. It was renamed the Midtown Beer Garden.