Free guide · Crews & hiring

The 1099 vs. Employee Compliance Guide

Paying helpers as contractors feels simple — until it isn’t. Know where the line actually is before someone else draws it for you.

The most expensive shortcut in the trades

Calling a worker a contractor skips payroll taxes, workers’ comp, and paperwork — which is exactly why the IRS and state agencies look hard at it. Misclassification can mean back taxes, penalties, and interest on every misclassified year, and in the green industry, crews are a known focus area.

Where the line really is

It’s not about what you call someone or what they agreed to — it’s about control. Who sets the hours? Whose tools and truck? Can they work for other companies, send a substitute, profit or lose on the job? The guide walks the factors that actually decide the question, in crew-boss language.

What the guide covers

  • The control tests in plain English, with trade examples
  • What a defensible contractor relationship looks like on paper (W-9s, invoices, agreements)
  • What to do if you realize someone’s been classified wrong — before it finds you

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