Insights for Small Business Owners
Plain-English tax, bookkeeping and payroll guidance from 27 years in federal tax.
Taxes
What the IRS Already Knows About Your Business (And What You Need to Have Ready)
Most small business owners imagine an IRS audit as a random event, a lottery they hope they never win. The reality is that audits are increasingly…
The Year-End Tax Planning Checklist Every Small Business Owner Needs Before December 31
Most small business owners think about taxes in April. The business owners who consistently pay less think about taxes in October, November, and December, when they…
LLC or S-Corp: Why the Entity You Chose May Be Costing You Thousands in Unnecessary Taxes
One of the most expensive tax decisions a small business owner makes is the one they made at the beginning and then never revisited. Business entity…
Home Office Deduction Done Right: What Qualifies, What Doesn’t, and What the IRS Will Ask
The home office deduction is one of the most misunderstood deductions in small business tax. Some business owners skip it out of fear. Others claim it…
Quarterly Estimated Taxes: The Complete Guide for Self-Employed and Small Business Owners
The IRS does not wait until April to collect what you owe. As a self-employed person or business owner, you are required to pay taxes four…
The S-Corp Payroll Trap: How the IRS Finds Business Owners Who Are Underpaying Themselves
Operating your business as an S-corporation comes with a significant tax advantage. Distributions to shareholders are not subject to self-employment tax. But the IRS has a…
The Tax Mistake That Quietly Costs Florida Small Business Owners Thousands Every Year
After 27 years in federal taxation, I can tell you the most expensive tax mistake small business owners make has nothing to do with cheating the…
Florida Small Business Tax Guide: What Every Orlando Business Owner Needs to Know
Florida is one of the most tax-advantaged states in the country for small business owners. No personal income tax. No inheritance tax. A corporate income tax…
The S-Corp Accountable Plan: Stop Paying Tax on Money That Should Be Tax-Free
If you operate an S-Corporation and you pay business expenses from your personal pocket — mileage, home office, software subscriptions, continuing education, cell phone — there…
The Augusta Rule: How Florida Business Owners Can Generate Tax-Free Income From Their Own Home
If you own a business in Florida and you own your home, there is a provision in the Internal Revenue Code that most business owners have…
Bookkeeping and Cash Flow
Profitable Business, Empty Bank Account: The Cash Flow Problem Most Business Owners Don’t See Coming
This is one of the most disorienting moments in small business ownership: your revenue is up, your profit and loss shows a positive number, and your…
Why Keeping Your Own Books Is Quietly Costing More Than a Bookkeeper Ever Would
I hear this every tax season: I keep my own books. I use the app. And every tax season, I spend the first hour of our…
Why a Profitable Business Can Still Go Broke: The Accounts Receivable Problem Most Owners Ignore
A business can show profit on paper and be completely broke in the bank. The accounts receivable blind spot is the most dangerous bookkeeping gap most…
Is Your Business Paying Taxes on Money You Already Spent? The Misclassification Problem Nobody Talks About
Expense misclassification is silently costing small business owners thousands in missed deductions and increased tax liability every year. Here is how to fix it.
The Bookkeeping Move Most Business Owners Skip, and Why It Quietly Costs Them
Monthly bank reconciliation is the single most important bookkeeping practice most business owners skip. Learn what it catches, why the IRS cares, and how to do…
Payroll
Payroll Compliance: The Three Violations That Put Small Business Owners in the IRS’s Crosshairs
Of all the areas the IRS audits, payroll is one of the most aggressively enforced. Payroll taxes are trust fund taxes: money withheld from employees paychecks…
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