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OUR INSIGHTS SUITE
Tax Strategy, CFO Insights & NIL Finance for Founders and Athletes


Why Doesn't My Payroll Software Register My Business in New States?
Payroll software can process paychecks flawlessly for months while the state registrations behind it are completely missing. Here's exactly what your software does, what it doesn't, and why the gap becomes one of the most expensive surprises a growing business runs into.

MJ Cunningham, EA
Jul 96 min read
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Why Do I Keep Getting Payroll Tax Notices? How They Escalate During Growth
One payroll tax notice rarely arrives alone, especially during a growth stretch. A missing registration or a half-finished unemployment account keeps generating fresh agency activity until someone fixes the root cause, and every notice that sits unresolved gets more expensive the longer it waits. Here's exactly how the first notice becomes the fifth, and what actually stops the pattern instead of just answering each letter.

MJ Cunningham, EA
Jul 56 min read
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Why Does Rapid Growth Cause Multi-State Payroll Problems?
Rapid growth feels like winning, but it's also one of the most common ways businesses end up with multi-state payroll exposure they never meant to create. New hires, relocations, and expanding teams can each trigger registration and filing requirements that nobody formally reviewed. Payroll keeps running normally the whole time, which is exactly why the gaps stay invisible until a notice arrives. Here's how the problem actually forms, and what to put in place before it does.

MJ Cunningham, EA
Jun 305 min read
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What Should You Do After Receiving a State Payroll Tax Notice?
A payroll tax notice can feel like everything went wrong overnight, but the letter is usually the discovery point, not the beginning. Most notices trace back to a registration gap, a remote hire, a relocation, or a provider transition that happened months earlier. Here are the nine steps to take, in order, to trace the notice back to its actual cause and stop it from escalating into something bigger.

MJ Cunningham, EA
Jun 236 min read
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Why Do Payroll Providers Miss Filing and Registration Problems?
"We thought payroll was handling this" is one of the most common lines businesses say after a notice arrives, and it's usually true, payroll was running fine. The problem is that payroll processing and payroll compliance are not the same function, and registrations, work states, and filings depend on information the provider was never given. Here's why these gaps slip past even a provider that's doing its job correctly, and who actually owns closing them.

MJ Cunningham, EA
Jun 116 min read
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