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


How Far Back Should a Payroll Tax Reconciliation Go?
Too short a lookback and you miss an older payroll tax problem. Too long and you pay to check periods that were never in question. Here is how to decide how far back your reconciliation should go.

MJ Cunningham, EA
Oct 234 min read


Does Ramp Work With QuickBooks? A Corporate Card FAQ for Business Owners
Before applying for a corporate card platform, the questions that matter are operational: does it work with your accounting software, can you control who spends what, and what happens when something goes wrong. Here are the questions we hear most about Ramp, answered straight.

MJ Cunningham, EA
Oct 144 min read


Ramp vs Brex vs BILL vs Divvy: Which Corporate Card Actually Fits Your Business?
Every corporate card platform says it is the best, and none of them are lying exactly. They are built for different businesses. Here is how Ramp, Brex, BILL, and Divvy compare from the accounting side of the desk, and how to match one to the way your company actually spends.

MJ Cunningham, EA
Oct 124 min read


Is Ramp Worth It? An Accountant's Guide for Growing Businesses
Most businesses are not frustrated with their credit card. They are frustrated with the chased receipts, late reimbursements, and slow month-end close that come after it. Here is what Ramp does about that, what it takes to qualify, and who it is not built for.

MJ Cunningham, EA
Oct 94 min read


IRS First-Time Penalty Abatement: Who Qualifies and How It Works
First-time penalty abatement is an IRS waiver that removes failure-to-file, failure-to-pay, and certain deposit penalties for taxpayers with a clean three-year compliance history, no hardship story required. This guide walks through the three eligibility tests, which penalties qualify, how to request it by phone, in writing, or in response to a notice, and what to do if the request is denied.

MJ Cunningham, EA
Aug 307 min read


What Is a Certificate of Good Standing in Texas?
If a lender, title company, or another state's registration office asked you for a Certificate of Good Standing, you searched for something Texas does not actually issue. The real document is called a Certificate of Fact, Status, and requesting it under the wrong name is the most common reason these requests stall or bounce back entirely.

MJ Cunningham, EA
Aug 166 min read


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


How Do Payroll Tax Problems Follow You Between Payroll Systems?
Switching payroll providers feels like a clean break, but registration gaps, unresolved notices, and filing errors do not belong to the software, they belong to the employer, and they follow the business into every new system until someone actually reviews the history. This post walks through why migrations expose old problems instead of causing them, and what to check before you switch.

MJ Cunningham, EA
Jul 76 min read


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


Why Payroll Software Does Not Automatically Solve Remote Employee Compliance Issues
Modern payroll software is powerful. It processes wages, runs direct deposits, and generates reports flawlessly. What it does not do automatically is identify every compliance obligation created by remote employees. Here is exactly why payroll software cannot replace operational oversight for remote workforces and what growing businesses need to have in place instead.

MJ Cunningham, EA
Jul 25 min read


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


Why Businesses Discover Missing Payroll Registrations During Growth
Missing payroll registrations almost never get discovered at the moment they are created. They get discovered during provider transitions, state notices, unemployment reviews, or rapid growth periods, months after the employee was already working. Here is exactly why growing businesses discover missing payroll registrations during growth and how to identify them before something forces visibility.

MJ Cunningham, EA
Jun 285 min read


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


The Most Common Remote Employee Payroll Mistakes Growing Businesses Make
Remote employees feel like a straightforward payroll addition. But each remote hire, employee relocation, or expanding remote team can create withholding registrations, unemployment accounts, and filing obligations in states your business was never set up for. Here are the nine most common remote employee payroll mistakes growing businesses make and what to do instead.

MJ Cunningham, EA
Jun 215 min read


What Is Payroll Nexus, and Why Is Your Growing Business Probably Already Exposed?
Payroll nexus means your business created tax obligations in a state through employee activity there, no office required. A remote hire, a relocation, or an expanding team can trigger registrations and filings you never knew existed, and most businesses find out only after the notices start arriving. Here's how to spot the exposure before that happens.

MJ Cunningham, EA
Jun 185 min read


Do Remote Employees Create State Payroll Registration Requirements?
Remote employees can create state payroll registration requirements even when a business has never opened an office in that state. Most businesses find out after payroll is already running, a notice arrives, or a provider requests account numbers that do not exist. Here is exactly when remote employees create registration obligations and how to identify your exposure before the problem compounds.

MJ Cunningham, EA
Jun 165 min read


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


Why Remote Workforce Growth Creates Multi-State Compliance Problems
Most businesses become multi-state employers gradually through remote hiring without ever noticing the exact moment it happened. One remote employee becomes three, three becomes seven, and suddenly payroll obligations exist in states nobody reviewed. Here is exactly why remote workforce growth creates multi-state compliance problems and what growing businesses need to do before the notices arrive.

MJ Cunningham, EA
Jun 95 min read


What Are the Most Common Multi-State Payroll Mistakes Growing Businesses Make?
Most multi-state payroll mistakes aren't the result of bad intentions, they happen because growth outpaces internal process. This guide walks through the nine most common ones, from assuming processing means compliance to carrying old problems through a provider transition, and what to check before each one turns into a notice.

MJ Cunningham, EA
Jun 76 min read


What Happens If Payroll Tax Registrations Were Never Completed?
Most businesses with missing payroll registrations do not find out until a notice arrives, a filing gets rejected, or a provider transition forces a review. By then payroll has been running for months on infrastructure that was never properly established. Here is exactly what happens when payroll tax registrations were never completed and how to fix it before the problem gets worse.

MJ Cunningham, EA
Jun 45 min read
bottom of page

