Every founder worries about product-market fit, fundraising, and hiring. Almost nobody worries about taxes — until a five-figure penalty or IRS notice arrives. Here are the five mistakes we see most often.

Payroll is one of the largest expenses for most startups, and one of the most misunderstood compliance areas. Most founders assume payroll taxes are handled automatically.

Many SaaS companies rely heavily on contractors — developers, designers, marketing specialists. At first, managing these relationships feels simple. Then January arrives.

A founder in Texas can hire an engineer in Colorado, a designer in California, and a product manager in Illinois within days. From a compliance perspective, it can get complicated fast.

What surprises me is how many AI companies are sitting on valuable tax credits without realizing it. The most common response I hear: “We didn’t think we qualified.”