Category: Bookkeeping & Systems

Online programs like QuickBooks Online have made it remarkably easy for business owners to do at least some of their own bookkeeping. Connect your business bank account and credit cards, and transactions start flowing into QuickBooks automatically. It can almost feel like the bookkeeping is happening for you. And that’s where one of the biggest…

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…

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…

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…

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,…

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…

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….

Why Bookkeeping Is the Foundation of a Smart Tax Plan For many small business owners, bookkeeping feels like a necessary evil — a compliance task to keep the IRS happy. But here’s the reality: accurate bookkeeping is the foundation of a proactive tax strategy as well as a powerful growth tool for your business. Without…