“Fine. Here’s your stupid letter,” I said the next time we talked. “Can you please make the threatening emails go away? You’re scaring people.” “Yes. I’ll send it over to the tax team right away.”

You guys, I really love Gusto. It’s not the fanciest tool out there. And it’s not cutting-edge anymore. That damned pig has been marching for over a decade at this point. But they’re really, really good at what they do. In that way that competence is often invisible. Until you see how someone else does it. I helped a client migrate from ADP Run to Gusto this week. Run is like ADP’s sh!tty knock-off Gusto. (They don’t like it when you call it that. A miffed ADP manager once po

The idea was to take everything that people hate about services like CorpNet and make it a pleasant, supportive experience for people. We’d answer their questions in words that made sense. We'd support them as they entered their tax IDs into their payroll system. If they got alerts from payroll or letters in the mail, we’d translate them into action.

This year, as you wallow in anxiety waiting for the tax team to get back to you, I have a fun project for you. Make sure your state payroll tax settings are correct. This is the only time when it DOESN’T feel irrelevant and boring. So Take advantage of it.

How does this even slip through? For THREE YEARS? Part of it had to do with a quirk of how taxes work in reciprocity states like Wisconsin. Part of it was because state agencies don’t talk to each other. And implementation teams aren’t tax experts. And some payroll providers don’t have enough error flags for situations like this. And humans are flawed. They make mistakes.

Have you ever wondered what it would be like if you threw five cats in a bag and asked them to run your payroll? Or have you already tried Paylocity?

You know why their checks are cut by ADP? Because most of them work at big, old companies and switching payroll providers is really, really hard at that size. And because people don’t know any better.

Here’s why your paycheck takes so long: Many companies pay in arrears. Which is a fancy way of saying that there’s a gap between the end of the pay period and when you actually get paid. If you’re paid hourly, there’s literally no way to get you paid without a gap. Here’s what’s happening in that time:

For my small business clients (who aren’t considering a PEO), the decision often comes down to Bamboo or Gusto. Both Bamboo and Gusto have clean, easy-to-understand user interfaces with cute graphics that really do make dry and stressful processes less intimidating and occasionally “delightful.”

When you work overtime, you’re paid time and a half. The OBBBA only applies to the “and a half” portion of your pay. The OBBBA only applies to federal overtime, or hours worked beyond 40 hours in a week.

Many companies with fewer than 200 people will literally sign away legal control of their employees and pay multiple times more for payroll services. Just so they don’t have to think about state tax settings.

Imputed pay is a type of non-cash benefit whose value is still taxable by the IRS. It could be life insurance, a domestic partner’s benefits, bills your employer paid for you, gifts. Answer: Your payroll person adds an “imaginary” dollar to your paycheck. That’s imputed pay.

Before you start planning how you’ll spend that “free” paycheck before your finance department re-balances the budget for 2026 you need to know that your payroll provider is probably smart enough to anticipate this. There are two methods that payroll providers use to solve the 27-paycheck problem: Pro rata and pay as usual.

These days, it seems obvious that workers should be able to demand an accurate accounting for their time. But it wasn’t always that way.

Here are five examples of mundane breakdowns that I’ve seen lead to payroll errors:

Except that something didn’t add up. They didn’t even have employees for half that time, and one of the people they were assessing violations on wasn’t even in the state.

Letters from government agencies can be real scary sometimes. Especially when they contain words like "Warrant" and penalties with commas in them. By all means, take these letters seriously. But don't let them scare you.

If more people could see the data, maybe they’d want to renegotiate. But they might also have a better understanding of how their value is measured, and therefore find ways to bring more value to the company.

You run a draft payroll the regular way to get the numbers, enter the gross pay into an off-cycle payroll, and it spits out a number that’s off by 17¢ from what regular payroll said. Why? Whyyyyy?

It drives me crazy when people treat a company’s FEIN (Federal Employer Identification Number) like it’s a big secret. FEINs are public information.