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From a Palo Alto closet to $1 billion revenue: how Gusto cracked small business software | Term Sheet

May 07, 2026 12:00 PM UTC

Approximately nine out of every ten net new jobs in America come from small businesses, yet they shoulder over $81 billion a year in federal paperwork. As more Americans launch their own businesses, the back office is buckling under the weight. In this episode, Josh Reeves, cofounder and CEO of Gusto, a payroll, benefits, and HR platform for small businesses, breaks down the contrarian bet that built a $9 billion company. He and Fortune's Allie Garfinkle discuss why small business tech is often overlooked, why he doesn't think AI labs like OpenAI and Anthropic will touch tax compliance, and how Gusto crossed $1 billion in revenue on its path to what Reeves believes is a trillion-dollar opportunity.

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