Tax Planning

Proactive tax strategies, deductions, and planning tips to help business owners legally minimize their tax burden year-round.

14 articles

Q2 Estimated Taxes Are Due June 15, Don't Overpay Under the New 2026 Rules

The OBBBA changed the rules for 2026. The SALT cap jumped to $40,000. Section 179 doubled. If you copy last year's Q2 payment, you may be overpaying by thousands of dollars.

Tom Woolley, MBA 5/5/26

Contractor Equipment Depreciation: How to Deduct $500K in the Year You Buy It

Contractors who understand Section 179 and bonus depreciation can write off hundreds of thousands in equipment the year they buy it. Here's exactly how it works and what qualifies.

Tom Woolley, MBA 3/2/26

LLC vs. S-Corp for Contractors: The Entity Choice That Saves (or Costs) $15K a Year

Most contractors operate as LLCs but pay thousands more in self-employment tax than necessary. Learn when to elect S-Corp status and how much it can save you annually.

Tom Woolley, MBA 3/2/26

23 Tax Deductions Every Contractor Should Be Claiming (But Most Miss)

From vehicles and tools to home office and health insurance, most contractors miss dozens of legitimate deductions every year. Here's a complete list with what qualifies and how to document it.

Tom Woolley, MBA 3/2/26

Is Your CPA Planning Your Taxes or Just Filing Them? (There's a $20K Difference)

Most CPAs file your taxes. Very few actually plan them. Learn the critical difference between tax preparation and proactive tax planning, and how much it's costing you.

Tom Woolley, MBA 3/2/26

Section 179 vs. Bonus Depreciation: Which Tax Strategy Saves You More?

Section 179 and bonus depreciation both let you deduct equipment costs immediately, but the rules differ significantly. Learn which strategy saves your business the most in taxes.

Tom Woolley, MBA 3/2/26

The Contractor's Year-Round Compliance Calendar: What Is Due, and What Only Works If You Do It Early

Filing deadlines are the easy half. The dates that actually decide a contractor's tax bill and cash position are the ones with no deadline attached at all.

Tom Woolley, MBA 3/2/26

How to Avoid an IRS Audit: What Business Owners Need to Know

IRS audits are rare but stressful. Here is what actually triggers them, which deductions draw the most scrutiny, and how to document your return so an audit is nothing to fear.

Tom Woolley, MBA 11/3/25

Best Retirement Plan Options for the Self-Employed: SEP IRA, Solo 401(k), and Beyond

Self-employed individuals have access to more powerful retirement plan options than most employees. Here is how to choose the right one and maximize your tax-deferred savings.

Tom Woolley, MBA 11/3/25

10 Valuable Small Business Tax Deductions You Might Be Missing in 2025

Most small business owners claim the obvious deductions. Here are 10 overlooked write-offs that could save you thousands, and how to document them properly.

Tom Woolley, MBA 11/3/25

5 Business Tax Saving Strategies to Stop Overpaying the IRS

Most business owners pay more in taxes than they legally have to. These five strategies target the most common and costly gaps in small business tax planning.

Tom Woolley, MBA 10/31/25

6 Tax Planning Strategies Every Small Business Owner Should Be Using

These six strategies are responsible for the majority of tax savings we find for small business clients. They are legal, proven, and available to you, but most business owners are not using them.

Tom Woolley, MBA 10/31/25

5 Tips and Tricks for Tax Time from Tax Pros (That Actually Save You Money)

Tax professionals see the same costly mistakes year after year. Here are 5 things the best tax advisors do differently, and how you can apply them to reduce what you owe.

Tom Woolley, MBA 10/31/25

The Complete Guide to Proactive Tax Planning for Business Owners

Most business owners overpay $10K+ annually. This complete guide to proactive tax planning shows you how to pay less legally, year-round, not just at filing.

Tom Woolley, MBA 2/11/24

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