Mastering the Money Game: The Financial Wake-Up Call That Saved My Business

The Day the IRS Almost Ended My Dream

I still remember the sick feeling in my gut the first time I realized I’d made a huge mistake.

It wasn’t a missed paint color, a bad review, or even a job that went sideways. It was a letter, from the IRS.

Turns out, when you run a painting business and you start hiring people, real people with real families, you’re not just the boss anymore. You’re the payroll department, the tax collector, the compliance officer, and the guy everybody’s going to blame if the math doesn't add up.

And mine didn’t.

What I thought I was “saving” by paying under the table ended up nearly costing me everything I had built.

That was the moment I decided: If I was going to make this business last, I had to master my finances, or they were going to master me.

Most Painting Contractors Start with a Brush, Not a Balance Sheet

Let’s be honest. You didn’t get into this industry because you loved paperwork. You got in because you’re good at what you do. Maybe it was painting, managing a crew, bidding jobs or just the dream of doing it your own way.

There’s one thing that separates the guys who survive from the ones who soar: they learn how to run the business behind the brush.

That means understanding:

• Why liability insurance isn’t optional

• How workers’ comp works without crushing your cash flow

• What happens when you don’t pay payroll taxes on time

• Why “on the books” matters more than you think

• And how to build a team of professionals who’ve got your back

Let me break it down for you.

There's an App for That. But There's No Shortcut for Trust.

When I first started, the only "app" I knew was short for "appetizer." Now? There’s an app for quotes, an app for timesheets, and an app for estimating materials. And that’s great, but no app can replace the trust and advice of a real professional, especially when it comes to insurance and accounting.

Here’s what I learned the hard way:

1. Build a Relationship with a Local Insurance Agent

Sure, you can shop online, but when your truck gets rear-ended or someone gets hurt on site, you don’t want a 1-800 number. You want someone who picks up the phone, knows your name, and goes to bat for you.

Your agent can:

• Help you bundle coverage (truck, liability, workers’ comp)

• Recommend risk management strategies to lower your premiums

• Break down your policy in plain English

• Fight for fair treatment if a claim arises

What matters most is protection, partnership, and peace of mind, not just coverage.

2. Find an Accountant Who Specializes in Small Trades Businesses

A good accountant doesn’t just do your taxes; they help you keep track of your cash flow, set up payroll the right way, file on time (and legally), and steer clear of costly IRS penalties.

When things get tight, as they sometimes do, they’re there to guide you toward smart decisions before problems spiral. For example, I now pay my workers’ comp weekly thanks to a recommendation from my accountant. No more massive upfront payments, just manageable, predictable costs that keep us compliant and protected.

3. Get Comfortable Being On the Books

Here’s a tough truth: you can’t grow your business on a cash-only model forever. If you stay off the books, you shut yourself out of opportunities. You can’t work with builders or big clients, you can’t get bank financing, and you can’t build real wealth. It might feel like a “hack” in the beginning, but the longer you try to avoid the system, the riskier it becomes.

When you pay your employees on the books, you protect them, you protect yourself, and you build a business that’s actually worth something.

What Happens If You Ignore This?

I’ve seen it happen, guys with more talent than me losing everything because they didn’t take this seriously. Some didn’t file taxes for three years and got crushed by penalties. Others got sued after an injury because they had no workers’ comp. Some couldn’t even qualify for a mortgage or business loan because they had no provable income.

You can hustle your way into a business, but if you want to stay in business, you need structure, systems, and support.

That’s Why I Created Painting Profit

Everything I just laid out comes straight from Lesson 6 of my Painting Profit course: Insurance and Finances. In this chapter, I break down the kind of insurance you actually need, how to protect your assets and minimize risk, and how to hire and pay your team legally and wisely.

You’ll learn how to build your dream team of an accountant, lawyer, and insurance agent, and more importantly, how to shift your mindset from tradesman to business owner.

I’ve also included a resource list packed with apps, referrals, templates, and pro tips to make this step easier. The real payoff isn’t just in dollars, it’s in freedom. The freedom to grow, freedom to sleep well, freedom to build something that lasts.

Take It From a Guy Who’s Been There

I used to think making more money just meant doing more jobs. Now I know keeping money, and protecting it is just as important. If you’re ready to stop chasing and start building, this is your moment. No more waiting for things to “settle down.” No more telling yourself “next year.” No more risking everything by putting off what feels hard.

Are you ready to take control of your business? Click below to get access to the Painting Profit course and take the next step toward financial mastery.

Painting Profit with Michael Hornby | LeaderPass