Last month, I had coffee with Mark, a CEO who’d just closed his best quarter ever. His company hit $12M in revenue. The team was celebrating. Investors were happy.
Then April rolled around.
His tax bill? $780,000.
“I felt like I got punched in the gut,” he told me. “Here I am, running a successful company, and I’m handing over three-quarters of a million dollars. Meanwhile, my buddy who runs a similar business paid half that.”
This conversation happens more often than you’d think.
The Problem Hiding in Plain Sight
Here’s something most people don’t realize: making more money doesn’t automatically mean you’re handling money well. Especially when it comes to taxes.
I’ve met brilliant CEOs who can optimize supply chains, negotiate million-dollar deals, and scale teams across continents. But when tax time comes? They’re basically flying blind.
The typical scenario goes like this:
- Build the business all year
- Hand everything to the accountant in March
- Get hit with a massive tax bill
- Pay it and promise to “do better next year”
- Repeat
It’s like trying to lose weight by only stepping on the scale once a year. By then, it’s way too late to change anything.
Why Smart People Make This Mistake
Most CEOs I know aren’t trying to cut corners or play games with the IRS. They’re just focused on what they do best – running their companies.
But here’s where it gets expensive: most accountants are really good at one thing – making sure you don’t go to jail. They file your forms correctly, they keep you compliant, and they charge reasonable fees for straightforward work.
What they don’t do is think strategically about your entire financial picture.
It’s like having a mechanic who’s great at oil changes but has never thought about performance upgrades. They’ll keep your car running, but they won’t make it faster.
The Real Cost of Playing Defense
When you’re only playing defense with taxes, you’re not just overpaying the government. You’re missing opportunities to reinvest in your business.
Think about what an extra $200,000 could do for your company:
- Hire two senior engineers
- Open that new location you’ve been considering
- Finally build that marketing campaign that could double your revenue
- Put it toward that acquisition that could change everything
Every dollar you overpay in taxes is a dollar you can’t use to grow – Discover these practical tax-saving tips for small businesses to keep more of your profits.
What Changes Everything
The CEOs who pay less in taxes aren’t doing anything shady. They’ve had a professional tax strategy consultation to rethink their approach.
Instead of asking “How much do I owe?” they’re asking “How do I structure things to keep more of what I earn?”
It’s the difference between playing not to lose versus playing to win.
This means:
- Planning tax strategy while you’re making business decisions, not after
- Understanding how your business structure affects your tax bill
- Looking at your entire financial picture, not just this year’s forms
- Having someone on your team who thinks about optimization, not just compliance
A Different Approach
A few months after that coffee, Mark called me with an update. He’d restructured a few things, changed how he was taking distributions, and set up some strategies we’d discussed.
His tax bill for a similar quarter? $380,000.
Same revenue. Same profit margins. $400,000 less in taxes.
“I wish I’d done this years ago,” he said. “Think about how much I’ve left on the table.”
The Bottom Line
Look, nobody enjoys paying taxes. But there’s a difference between paying your fair share and overpaying because you didn’t know there were other options.
If you’re a CEO and your tax conversations only happen in March, you’re probably overpaying. If the only advice you get is “you owe X amount,” you’re definitely overpaying.
The good news? Unlike most business problems, this one has a clear solution. You just need to stop thinking about taxes as something that happens to you and start thinking about them as something you can control.
Because at the end of the day, it’s your money. Shouldn’t you have a say in how much of it you get to keep?
Ready to see what strategic tax planning could do for your business?
We offer complimentary strategy calls where we’ll walk through your specific situation and show you exactly where you might be overpaying. No sales pitch, just honest feedback about your options.