Category: Payroll & Contractors

Every January, small business owners find themselves searching through emails, spreadsheets, and old invoices trying to figure out who needs a 1099. The process feels complicated until you understand a few simple rules—and once you do, issuing 1099s becomes one of the easiest year-end tasks in your business. This beginner-friendly guide breaks down what you…

Every small business owner eventually asks the same question: “Where does my owner’s draw show up in my financials—and what does the IRS really tax?” The IRS does not tax how much money you take out of your business. Instead, it taxes your business profit and taxable wages, depending on your entity type. Whether you’re…

Whether you’re a solo practitioner, PLLC, S-Corp, or group practice owner, the IRS considers therapists and therapy practices to be businesses. That means the same contractor and 1099 rules that apply to small businesses also apply to you. Many therapists unintentionally skip required 1099s because they: Assume their EHR handles tax reporting Pay contractors through…

Whether you work solo, on a team, or lead your own real estate business, the IRS views you as a business owner. That means you must follow the same 1099 rules as any other independent professional. Every year, realtors miss required 1099 filings because they: Assume the brokerage handles it Don’t realize which vendors need…

Every January, business owners scramble to collect W-9s, figure out who they paid, clean up payment records, and rush to file 1099s by the deadline. But the truth is simple: 1099 filing is easy when your vendor list is organized year-round. A clean vendor list means: No missing W-9s No guessing who needs a 1099…

Landlord 1099 Requirements Explained: Contractors, Property Managers & More Landlords operating rental properties are considered business owners, and like any business owner, landlords may need to issue 1099s for certain payments throughout the year. Unfortunately, most landlords don’t learn these rules until tax time, when their CPA asks for contractor totals and W-9 forms. This…

Backup Withholding for Small Businesses: A Simple Guide to a Confusing IRS Requirement Backup withholding is one of the least understood IRS rules — yet it’s something every business owner should know. Most don’t learn about it until a contractor refuses to provide a W-9 or the IRS sends a “B-Notice” about a tax ID…

How to Pay Contractors Without Triggering 1099 Requirements (Legally) Most business owners assume filing a 1099 is unavoidable — but the IRS rules tell a different story. Depending on how you pay a contractor, you may not need to issue a 1099-NEC at all. Some payment methods shift the reporting burden away from you entirely,…

How to Handle a Missing W-9 From a Contractor — Even After You’ve Already Paid Them Form W-9 is one of the simplest yet most important documents in your contractor onboarding process. It gives you a contractor’s legal name, business classification, and tax identification number — all information you must have to properly issue a…

Employee or Contractor? The True Cost of Misclassification and IRS Penalties for Getting It Wrong Classifying a worker as an independent contractor may feel simpler — less paperwork, no payroll system, and fewer employer responsibilities. But if the IRS or state regulators determine that a contractor should have been classified as an employee, the financial…