"The next 100 years are going to be nuts," David Barrett wrote at the top of his letter in Expensify's prospectus. Few founders open an IPO filing that way. Barrett had built a company around a chore everyone hated: the expense report. Employees photographed receipts, and Expensify turned them into reports their bosses could approve. By November 2021 an average of 639,000 paid members across 53,000 companies used it each quarter, and tech stocks were near their peak.

A Chore Worth Fixing

Barrett had led engineering at Red Swoosh, a file-sharing startup that Akamai bought in 2007. He founded Expensify in 2008, and it was incorporated in April 2009. The bet was that small and midsize businesses would adopt a tool their employees chose for themselves, then pay for it. Expensify connected to QuickBooks, Xero, NetSuite and other accounting systems. In early 2020 it launched the Expensify Card to earn money on spending itself.

A Long Slide

Expensify priced its offering at $27 a share in November 2021 and listed on the Nasdaq Global Select Market as EXFY. The offering raised about $263 million and valued the company near $3.87 billion after a strong debut. Then the market for small-cap software turned. The stock has since fallen more than 95 percent from its debut. Barrett still runs the company from Portland, Oregon, and it still trades on Nasdaq.

Cover: Still Life with Travelling Trunk, Leonard Bramer. Art Institute of Chicago, public domain. Chosen for a traveling trunk (business travel and its receipts).