Practical Tax & Accounting
Insights for Business Owners

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,…

Do LLCs Get 1099s? How to Tell When an LLC Does (and Doesn’t) Need a 1099 LLCs are one of the biggest sources of confusion for business owners preparing 1099s. Many people assume that if a vendor’s name includes “LLC,” they’re automatically exempt from reporting — but that’s not how the IRS works. Here’s the…

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…

1099-K Confusion Solved: How PayPal, Venmo & Stripe Affect Your 1099 Obligations Payment apps have transformed how small businesses send and receive money — but they’ve also created enormous confusion about who must file which 1099 form, and when a 1099-K appears instead of a 1099-NEC. If your business uses PayPal, Venmo, Stripe, Square, Etsy,…

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…

A Beginner’s Guide to Filing Your Own 1099s (Without Paying a Professional) This guide walks you through what you need, where to file, how to handle common roadblocks like missing W-9s, and how to avoid the mistakes we see most often. With a little preparation, you can confidently handle your annual 1099 filings without paying…

1099 Filing Requirements Explained: What Every Small Business Owner Needs to Know What Are 1099 Forms? Every year, small business owners must report certain payments made to contractors, landlords, attorneys, and other vendors. Form 1099 is how the IRS ensures it receives reporting on income paid outside of payroll, and understanding these rules helps prevent…

If you only think about taxes once a year — usually in April — you may be missing some of the biggest opportunities to save money, avoid IRS penalties, and protect your cash flow with tax planning. Tax planning isn’t just for the ultra-wealthy or giant corporations. It’s for business owners, consultants, and professionals who…

Starting a new business is exciting — but nothing takes the wind out of your sails like your first unexpected tax bill. Many first-year business owners who find themselves profitable are caught off guard by the self-employment tax. As a W-2 employee, your employer handled payroll taxes and you simply lived on your take-home pay….