Summary of What This Blog Covers:
- What most tax prep misses, from unreconciled books to missed deductions
- Key compliance steps to avoid IRS penalties
- When to switch to advanced strategies like S-Corp and retirement plans
- Why real CPAs offer more value than DIY tax software
You’ve got momentum. Your business is humming, clients are returning, cash is coming in and somewhere, in the back of your mind, you’re thinking, “I should probably get ahead of tax season.”
Smart thinking.
Now let me guess. You’ve got a QuickBooks Self-Employed login, maybe a TurboTax Free File tab open (again), a W9 or two floating around in your inbox, and a vague memory of something you meant to deduct but didn’t.
Sound familiar?
If so, you’re not alone and this blog is for you.
Tax season doesn’t just reward the organized. It rewards the strategic. The intentional. The business owner who asks the right questions before April 15 rolls around and makes everything harder.
So, here they are: 10 questions that every business owner should be asking before tax season even thinks about starting. Answer them honestly. And if any of them make you squirm a little? That’s your cue to call us.
1. Is My Bookkeeping Actually Reconciled Or Just Technically There?
Let’s start with the basics.
You’ve got income. Expenses. You’ve maybe even linked a few bank accounts to your accounting software. But is your bookkeeping actually reconciled?
That means:
- Every bank transaction has a category.
- Every credit card charge has a match.
- Your balance sheet doesn’t look like it’s been through a blender.
Why it matters: Tax returns built on sloppy books = red flags for the IRS.
This isn’t a spreadsheet suggestion. It’s a tax savings move. Clean books make it easier to spot missed deductions, over-reported income, and even fraud. Let your CPA in Austin, Texas (hi, that’s us) take a look. We know where to tidy up fast.
2. Are PayPal, Stripe, and Venmo Transactions Being Tracked Correctly?
If you’re using PayPal or Stripe, congratulations. You’ve entered the world of 1099-K forms.
These platforms report your gross revenue to the IRS. And guess what? If you don’t report the same gross number, the IRS thinks you’re hiding something.
Also: Venmo. If you’re accepting business payments through your personal Venmo account, stop doing that. Today.
Why it matters: You must track gross revenue, not just what hits your checking account after fees. Miss this, and your taxes are off from line one.
Fix it by syncing these platforms to your accounting software, categorizing your fees, and letting a small business CPA in Austin verify that everything matches up. Because mismatches are the stuff IRS letters are made of.
3. Are You Reporting Gross Revenue or Just Net Bank Deposits?
This is one of the most common (and dangerous) errors we see.
You look at your bank statement, see what’s deposited, and assume that’s your revenue. Wrong. You forgot about:
- Credit card processor fees
- Refunds and chargebacks
- Sales tax collected
IRS doesn’t care what landed in your account. They care what you earned in gross sales. And if your 1099-K form shows $180,000 but your return only shows $160,000, you’ve got a problem.
Your Austin tax accountant can help clean this up, but you’ve got to bring it up before filing. Not after the audit letter arrives.
4. Did You Capture Every Deductible Expense or Just the Obvious Ones?
Everyone remembers office supplies and software. That’s easy. But here’s what you may have missed:
- Home office expenses (yes, even if you work from the dining table)
- Business mileage (tracked with apps like MileIQ or manually logged)
- Health insurance premiums for self-employed
- Continuing education or training
- Marketing subscriptions and industry tools
Every one of those is a legitimate deduction. And every one is often missed by business owners who try to DIY their taxes with TurboTax Online or TaxAct.
Don’t leave money on the table. Work with a certified public accountant near you who asks better questions than software prompts ever will.
5. Do You Have W9s on File and Are Your 1099-NEC Forms Ready to Go?
Let’s talk about contractors. If you paid anyone more than $600 this year for services and they’re not incorporated, you need to file a 1099-NEC form.
And you need their W9 tax form on file before you pay them.
Why it matters: Failing to issue a 1099-NEC can lead to IRS penalties, unhappy contractors, and a nasty paper trail.
This is not the kind of thing you want to scramble through in January. A licensed CPA can prep, file, and send your 1099s while you keep working on your business.
6. Are You Paying Yourself the Right Way?
Whether you’re a sole proprietor, LLC, or S-Corp, how you pay yourself matters.
Taking random transfers out of the business account into your personal one? That’s not payroll. That’s messy.
If you’re an S-Corp and not on a reasonable salary, the IRS will notice. If you’re a sole prop and not tracking owner draws separately from expenses, you’re muddying the waters.
Let a certified professional accountant help you structure owner compensation correctly before it causes tax complications.
7. Should You Elect S-Corp Status This Year?
This is the “tax saving strategy no one tells you about until it’s too late” question.
If your business profit is above $50,000, an S-Corp election might reduce your self-employment tax significantly. But it has to be done on time and once the year closes, you can’t backdate it.
Your CPA office near you can run the numbers and see if it makes sense for your business. You could be saving $3,000–$10,000 annually just by changing how your income is classified.
That’s not a tax hack. That’s tax intelligence.
8. Do You Have a Retirement Plan in Place and Is It Funded?
Here’s one of the most underused tax planning tools for business owners: solo 401(k)s, SEP IRAs, and SIMPLE IRAs.
Why they matter:
- They lower your taxable income
- They help you invest in your future
- They keep more of your profits working for you, not the IRS
You don’t need to be a Fortune 500 company to use these plans. A CPA near you or a tax advisor in Austin can help you figure out how much you can contribute and when.
9. Are You Making Quarterly Estimated Tax Payments or Crossing Your Fingers Until April?
If you made money this year (which you probably did), and didn’t make estimated payments, you might owe IRS penalties even if you’re due a refund.
Yes, really.
Estimated tax payments are the IRS’s way of saying, “Pay as you go.” Miss a quarter, and the IRS dings you. Not huge money, but enough to annoy you.
A self-employment tax calculator won’t tell you this. We will.
Better plan? Let your Austin, Texas CPA calculate your estimated payments and file them for you so there are no surprises come tax time.
10. Do You Understand Your Financial Reports or Are You Just Nodding?
Balance sheets. Profit and loss statements. Cash flow reports. These aren’t just for your accountant. They’re for you.
They tell you:
- How much you’re really making
- Where your money’s going
- How much tax you’ll owe
- What you can afford to invest, pay yourself, or hire
If you’re not reviewing them monthly—or worse, not reviewing them at all—you’re not running your business. You’re guessing.
Let a certified CPA walk you through the numbers. No jargon. Just clarity.
Let’s Wrap This Up Like a Pro
You’ve built something incredible. You don’t need to reinvent your business before tax season but you do need to sharpen your strategy.
At Insogna, we help business owners like you take control of tax season without the stress, guesswork, or generic software prompts. Whether it’s reconciling your books, filing 1099 NEC forms, managing FBAR filing, or walking you through an S-Corp election, we’ve got your back.
You bring the business. We’ll bring the clarity, compliance, and confidence.
If you can’t answer all 10 questions with a firm “yes,” schedule your 15-minute clarity call with Insogna today. We’ll make sure your taxes and your strategy are as smart as the business you’ve built.