The Business Behind the Brush: Choosing the Right Structure for Growth

When I started my painting company, I was the crew, the estimator, the bookkeeper, the marketer, and the therapist to the anxious homeowner. I answered the phones in the morning and rolled ceilings at night. My title? Sole Proprietor and I wore it like a badge of honor.

But what I didn’t know back then could’ve cost me everything.

Let’s rewind to a crisp fall morning on a project in Seaside Park. I was elbow-deep in a kitchen repaint, trying to manage a color change, a backordered faucet, and a crew member calling out sick… again. My phone rang. It was a client asking about an unpaid invoice, then my bank called about an overdraft, and then the town zoning office called about a missed permit.

That day, I realized something: I wasn’t running a business, I was surviving one.

The Rookie Mistake Most Contractors Make

If you’re like I was, you started your painting business because you were good with a brush, not because you majored in business law or finance.

But here’s the truth: your legal structure isn't just paperwork; it’s the foundation of your protection, your profit, and your potential.

Let’s break it down.

Stage One: Sole Proprietor – The Hustler Stage

Nearly every painting contractor starts here. You file a DBA (“doing business as”), take on every job you can, and all income and liability flows directly to you.

That’s fine… for a minute.

But the moment a customer slips on a drop cloth or your helper backs the van into a mailbox, guess who’s legally on the hook?

You are.

You are the business. The business is you.

No separation, no safety net, just you, your ladder, and your checking account.

Stage Two: LLC or S Corp – The Grown-Up Move

Eventually, if you're serious about growing, you form a Limited Liability Company (LLC) or S Corporation (S Corp). These structures give you two major benefits:

1. Protection — Your personal assets are (mostly) shielded from business debts or lawsuits.

2. Tax Flexibility — You can choose how you’re taxed: as a pass-through entity or a corporation, depending on what’s best for your situation.

At this stage, you’re still likely in charge of everything, but now you have some structure and protection in place.

Heads up: I’m not an accountant. I’m a painting contractor just like you, but I strongly recommend you get one. A good accountant is worth their weight in Sherwin-Williams stock.

Stage Three: C Corp – The Empire Builder

If you're scaling fast, taking on large commercial contracts, hiring a team, or building a multi-state brand, you might consider a C Corporation.

It’s rare in the painting world, but not unheard of. With a C Corp, you become an employee of your business. That opens new doors — and new responsibilities.

But let’s zoom in on something even more important than tax structures:

The Three Hidden Roles in Every Successful Painting Business

Whether you’re a one-man show or running three crews, every painting business needs to define these three roles:

1. The Visionary (That’s You)

You’re the spark, the rainmaker, the one who sees what’s possible. You set pricing, build relationships, and dream big. But you can't do it all.

2. The Integrator (Your Right Hand)

This is your ops manager, lead painter, or job supervisor, the one who takes your ideas and makes them real.

I once had a sharp ops guy named Eric. I’d show up to the job site, excited to “help,” and start barking orders. One day, he pulled me aside and said:

“Michael, if you want me to run this crew, let me run the crew. If you step in, you undercut everything.”

That hit hard, but he was right. I had to learn to trust the integrator.

When you’re ready to grow, you’ll need to let go.

3. The Administrator (The Backbone)

Billing, scheduling, estimates, timecards, licenses. The stuff that makes most painters glaze over.

The good news? You don’t have to hire a full-time admin on day one. Sites like Fiverr or Upwork let you outsource admin work fast and affordably, until you’re ready to bring it in-house.

Why This Matters More Than You Think

Here’s what happens when you don’t define your structure, legal or operational:

• You overpay in taxes.

• You risk lawsuits that could take your house.

• You burn out doing $15/hour admin work instead of $1,000/hour CEO work.

• Your team gets confused about who’s in charge.

• You get stuck in the truck instead of growing the business.

But when you build the structure?
You create a business that works even when you’re not there.

That’s what I want for you.

What Type of Business Are You Building?

• A job? (You don’t clock in, you don’t eat.)

• A hustle? (Busy today, broke tomorrow.)

• A system? (Runs on process, not pressure.)

It’s time to stop winging it and start building it. You don’t have to do it alone.

If you’re serious about becoming a professional, not just a painter, my Painting Profit course is built for you.

We go deep into:

• Choosing the right legal structure (with checklists for each stage)

• Building your Visionary–Integrator–Admin model

• Delegating the right tasks at the right time

• Scaling with systems that work

• And building a business that doesn’t burn you out

It’s not a theory, it’s 30 years of what works, and what doesn’t, boiled down into tools you can use right now.

If this hit home for you and you’re tired of wondering what comes next, tired of wearing all the hats, tired of hustling instead of scaling, it’s time to get clarity.

Start by asking:
“What role am I best at — Visionary, Integrator, or Admin?”
And “Who do I need to bring in so I can do more of that?”

Then let’s build a business structure that serves you, instead of one that sinks you.

Join the Painting Profit Program and take the next bold step in your journey.

Because you weren’t meant to just paint houses, you were meant to build something that lasts.