May 19, 2023 11:00 AM PDT

On May 9, Expensify issued a quarterly earnings report that even its likable longtime CEO couldn’t soften. It had been a “nuclear winter” for the economy, David Barrett told shareholders. There were silver linings for his expense management software company, but “don’t get me wrong, this quarter sucked.” His blunt diagnosis ignited a sell-off on shares in the $500 million firm, sinking Expensify’s stock to an all-time low, down 87% from its public market debut just 18 months ago.

But as dour as the Q1 earnings may have been, the vibe the next day inside the company’s weeks-old co-working space, the Expensify Lounge, was the extreme opposite. There, perched on the 16th floor of a downtown San Francisco high-rise, it felt like 2018 all over again.

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Art by Clark Miller.
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