Xero CEO: Why America’s entrepreneurship boom is only half the story

Sukhinder Singh Cassidy is the CEO of Xero. Xero and its payroll partner Gusto are both named in this piece, and the owner-pay figure is Gusto data.

One of the most consistent things I hear from founders is some version of: “The business is doing well, so why don’t I feel like I’m winning?”

That question is critical. Because on every headline measure, they are winning. In 2025, the U.S. recorded approximately 5.7 million business applications, a new annual record. This rise was driven by AI, with 60% of new business owners saying they used it to help launch their business that year, double the rate from 12 months earlier.

Small businesses generate trillions in economic activity. They create jobs. They power entire communities. And yet the owner, the person who took the real risk, is asking: Was it really worth it?

We’ve seen this tension before, and speaking from experience, I have felt it. I think about my older sister Nicky, an optometrist who owned a practice in a shopping mall. She worked day and night to make her business succeed, but that stress never fully translated into her bank account. She had the company P&L, but not a framework for understanding whether she was thriving financially or personally.

That gap is what’s hiding in plain sight in the American small business economy right now.

The missing measurement

We already measure revenue, job creation, and GDP contribution. These make up the scorecard. And by that scorecard, entrepreneurship looks healthy. But we don’t measure whether the owner is actually earning a living wage.

Data from Xero’s payroll partner Gusto found that in 2025, the median small business owner paid themselves $4,800 per month, about........

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