Skip to content

October 9, 2026 · chris boydstun

Your first hire: contractor or employee

You are turning down bookings because you run out of hours, not units. That is the signal. Not ambition, not a good month. Hours.

So you are hiring. And the first thing everyone tells you is to decide between a contractor and an employee, as though that were a preference.

Say the boring part first

Whether someone is a contractor or an employee is not a choice you make for convenience. It is determined by the facts of the working relationship and by federal and state rules, and some states are much stricter than others. Getting it wrong is a back-taxes and penalties problem, not a paperwork problem.

That decision belongs to your accountant, with your actual facts in front of them. One conversation, before the first paycheck, costs less than any other order of events. Nothing below is a substitute for it.

What this post can tell you is what changes about your Saturday under each model, because that is the part an accountant cannot tell you.

What actually changes in how you run the day

How much control you have. This is the center of it, both operationally and legally. An employee can be told when to show up, what to wear, what order to run the stops in, and how to do the setup. The more you dictate those things, the more the relationship looks like employment, whatever the paperwork says. If you need someone in a shirt with your logo, arriving at 6:45, running your route in your order, you are describing an employee.

Who supplies the tools. Your truck, your trailer, your blowers, your straps, or theirs. A contractor with their own truck and their own insurance is a genuinely different arrangement than someone driving your rig.

Training. An employee you train. A contractor you hire for a skill they already have. In this trade almost nobody arrives knowing how to anchor a unit correctly, which is worth sitting with honestly.

Whose name is on the interaction. The person in the customer's backyard is your business as far as that parent is concerned. Word of mouth does not distinguish between a 1099 and a W-2.

How you pay, and what you withhold. Two different processes, two different year-end forms, two different amounts of bookkeeping. Whichever you choose, weekly and on time matters more to a weekend worker than the rate. See what to pay a delivery driver for the structures.

Coverage. Workers compensation and how your liability policy responds both depend on classification. Bring it up with your agent in the same week you bring it up with your accountant. Insurance in plain language covers what to ask.

Before anyone else can run a stop, write three things down

This is the part that gets skipped, and it is why first hires fail. The knowledge is in your hands and your memory, and nobody can be handed a Saturday out of your memory.

The load list. What goes on the trailer for a given unit. Blower, stakes or sandbags, cord, tarp, patch kit, the sign. One list, laminated, on the trailer wall.

The setup standard. In order, with the numbers. Anchor count, ballast weight on hard surfaces, cord gauge, how far from the fence, where the intake faces, what gets checked before he leaves. This is the document that keeps your insurer's questions answerable and keeps your name intact.

The customer script. What he says at the door, what he shows the parent before leaving, what he says if something is wrong. Two minutes of words that decide whether that parent books you again.

Write them once. They are also your training material, your quality bar, and the thing you point at when a stop goes wrong without it being personal.

Test on a ride-along, not on an interview

Bring the candidate on a real Saturday, paid, as a second set of hands. You are watching for four things, and only one of them is physical:

  • Does he show up when he said he would
  • Does he handle heat and a long day without getting short with people
  • Does he talk to the customer like an adult
  • Does he ask before guessing

Anyone strong enough will get strong enough at the lifting. Nobody becomes reliable in August because you hoped.

Then hand over one lane and watch it from the truck

Do not hand over the whole Saturday on week one. Hand over one lane of stops. Each stop carries its own address, contact, equipment list, notes, and pay. He claims it, runs it, and marks it done from his phone. You see the completion come back with a time on it, from wherever you are.

That is the real point of a first hire. Not more capacity. Coverage. A Saturday that no longer requires you to be in the cab for every one of it.

Talk to the accountant. Write the three documents. Ride along once. Then hand over a lane.

See a dispatched stop from both sides in the demo. No signup, no card.