Hiring Your First Employee: Tax and Payroll Obligations You Can't Skip
Hiring your first W-2 employee means new payroll tax obligations. This 2026 guide covers FICA, FUTA, Form 941, deposit deadlines, and Minnesota requirements.
John C Thompson, EA
Category: Business Tax
19 posts
Employee vs. Independent Contractor: How the IRS Decides Worker Classification
Deciding between 1099 and W-2 for your first hire? Learn the IRS worker classification test, misclassification penalties, and how to document your decision.
John C Thompson, EA
AI Bookkeeping Tools: What They Do Well and Where You Still Need Human Eyes
AI bookkeeping tools save time on data entry — but they can't read intent. Learn where automation helps and where human review protects your books.
John C Thompson, EA
Which Business Entity Is Right for You? A Decision Framework
Sole prop, partnership, S Corp, or C Corp? Here's a practical framework to help you choose the right business structure for your situation.
John C Thompson, EA
Your Business Numbers: What to Track, When to Review, and What the Ratios Mean
Most business owners only look at their numbers at tax time. Here's why that's too late — and a practical review cadence plus realistic financial benchmarks to actually use.
John C Thompson, EA
Home Office Deduction: The Complete Guide for Remote Workers and Self-Employed Businesses
Work from home and run your own business? The home office deduction can reduce your tax bill — but only if you meet the requirements. Here's how it actually works.
John C Thompson, EA
Going Independent: Tax and Bookkeeping Essentials for New Tech Consultants
Making the leap from W-2 to 1099? Here's what changes on your taxes when you go independent — self-employment tax, estimated payments, deductions, and why bookkeeping matters from day one.
John C Thompson, EA
How Messy Bookkeeping Affects Your Taxes (And What to Do About It)
Disorganized books don't just make tax season stressful — they cost you money in missed deductions, IRS notices, and late filing penalties. Here's what the connection looks like and how to fix it.
John C Thompson, EA
New Business Tax Obligations: Your First-Year Checklist
Starting a business in Minnesota? This complete first-year tax checklist covers EIN, entity structure, estimated taxes, bookkeeping, and every obligation you need to know.
John C Thompson, EA
Schedule C Deep Dive: Self-Employment Income and Deductions
Complete guide to Schedule C for self-employed individuals. Learn how to report income, maximize deductions, and understand self-employment tax calculations.
John C Thompson, EA
1099-NEC vs. 1099-MISC: Understanding Contractor Tax Forms
Confused by contractor tax forms? Learn when you receive 1099-NEC vs 1099-MISC, what they mean for your taxes, and exactly what to do when they arrive.
John C Thompson, EA
Minnesota Sales Tax Basics: What Small Business Owners Need to Know
Minnesota business owner? Learn when to collect sales tax, how to register, filing deadlines (Feb 5 for annual filers), and common mistakes to avoid.
John C Thompson, EA