I’ve been staring at spreadsheets for three weeks straight.
Not because I love numbers (though I do), but because we just finished the most eye-opening project our firm has ever undertaken. We reviewed 250 business tax returns from companies doing anywhere from $500K to $25M in revenue.
What did we discover? Nearly every single one was leaving money on the table.
And I mean serious money. We’re talking $30K to $100K+ per year that successful business owners were essentially donating to the Treasury Department.
The Pattern That Kept Showing Up
Here’s what surprised me most: These weren’t businesses with sloppy bookkeeping or discount CPAs. Most had solid accounting firms. Professional-looking returns. Everything filed on time.
So why were they overpaying?
The answer came down to one thing: timing.
Most businesses approach taxes like historians instead of strategists. They look at what happened last year and calculate what they owe. Period.
But the wealthy? They think months (sometimes years) ahead. They’re constantly asking, “What moves can we make now to change our tax situation later?”
That difference in thinking is worth tens of thousands of dollars annually.
The September 15 Reality Check
Your Q3 estimated payment is due in a few weeks. If you’re like most business owners, you’ve probably already calculated what you “owe” and mentally prepared to write that check.
But here’s what we learned from those 250 returns: That number you’re planning to send? There’s a 96% chance it’s higher than it needs to be.
Not because of sketchy tax tricks or risky schemes. Because of legitimate, IRS-approved strategies that most CPAs simply don’t discuss during regular compliance work.
Why Smart CPAs Still Miss This Stuff
Before you start questioning your accountant, understand this: Most CPAs are incredible at what they do. They keep you compliant, catch mistakes, make sure everything’s filed correctly.
But compliance and strategy are two different animals.
Compliance asks: “What do we owe based on what already happened?”
Strategy asks: “What can we do right now to legally owe less?”
Most accounting firms are built around the first question. The second one requires a completely different conversation – and frankly, a different fee structure.
What We Actually Found
When we dug into those returns, three patterns kept showing up:
Business structures that hadn’t evolved with revenue growth. A company doing $200K needs different entity planning than one doing $2 M. But many businesses never made that transition.
Retirement planning was either non-existent or completely basic. We found business owners in their 40s and 50s with barely any tax-advantaged retirement savings, missing out on huge current-year deductions.
Income timing that was… well, accidental. Most businesses just let income and expenses fall where they naturally land. But strategic timing can shift thousands of dollars between tax years.
None of this is rocket science. But it requires thinking beyond April 15.
The Real Cost of “Playing It Safe”
Here’s something that stuck with me from this whole project: Almost every business owner we talked to said some version of, “I’d rather overpay than get in trouble with the IRS.”
I get that mindset. Nobody wants an audit. Nobody wants penalties.
But “playing it safe” has a real cost. When you overpay by $50K this year, that’s $50K not going toward:
- New equipment that could generate more revenue
- Additional team members who could grow your business
- Marketing that could expand your market share
- Simply having more cash flow breathing room
Safety is expensive when you’re being too safe.
What’s Still Possible Before September 15
The good news? If you’re reading this in late August or early September, there are still moves available.
Equipment purchases can be accelerated. Retirement contributions can be maximized. Income timing can be adjusted (within reason). Business structures can be evaluated for next year’s planning.
Your Q3 payment doesn’t have to be set in stone just because that’s the number someone calculated for you.
The Question That Changes Everything
After reviewing all those returns, if I could get every business owner to ask themselves one question, it would be this:
“Am I approaching taxes like a business strategy, or just like a bill I have to pay?”
Because here’s what those 250 returns showed me: The businesses treating taxes strategically were keeping significantly more of what they earned.
And the ones treating it like just another bill? They were funding everyone else’s success instead of their own.
Want to see where your business fits in these patterns? We’re hosting a live session covering the specific strategies we found in our review of 250+ tax returns.
LIVE: We Reviewed 250+ Tax Returns — 96% Were Overpaying the IRS. Are You Next?
[ Register here ] to see if you’re in that 96% who could be keeping more of what they earn.