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Tax Planning

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

19 articles

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

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

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)

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)

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
The Dentist's Guide to Retiring With $1M+ (Using Tax-Advantaged Strategies)

The Dentist's Guide to Retiring With $1M+ (Using Tax-Advantaged Strategies)

High-income dental practice owners have access to retirement plans that can shelter $70,000 to $275,000+ per year from taxes. Here's how to build $1M+ in retirement wealth while cutting your tax bill.

Tom Woolley, MBA 3/2/26
Why Dentists Overpay $30,000+ in Taxes Every Year (And How to Stop)

Why Dentists Overpay $30,000+ in Taxes Every Year (And How to Stop)

The average dental practice owner overpays by $20,000 to $40,000 annually due to wrong entity structure, no retirement plan, and missed equipment deductions. Here's how to close the gap.

Tom Woolley, MBA 3/2/26
Section 179 vs. Bonus Depreciation: Which Tax Strategy Saves You More?

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 Year-Round Tax Calendar Every Business Owner Needs

The Year-Round Tax Calendar Every Business Owner Needs

Most business owners think about taxes in April. The ones who save the most think about them in October. Here's a month-by-month tax planning calendar to keep more money in your pocket.

Tom Woolley, MBA 3/2/26
We Guarantee $10K in Tax Savings. Here's What We Find in 14 Days.

We Guarantee $10K in Tax Savings. Here's What We Find in 14 Days.

Most business owners overpay taxes by $10,000+ annually. We guarantee we'll find those savings in 14 days—or we pay you. Here's exactly how we do it.

Tom Woolley, MBA 2/24/26
The Tax Savings Guarantee That's Never Been Paid Out: Why We're That Confident

The Tax Savings Guarantee That's Never Been Paid Out: Why We're That Confident

TodayCFO offers a $10,000 guarantee on tax savings for qualifying contractors and small business owners. Here's what it covers, why we've never paid it, and what that tells you about what we find.

Tom Woolley, MBA 11/10/25
Dental Equipment Tax Strategy: How to Turn a $200K Equipment Purchase Into a $70K Tax Break

Dental Equipment Tax Strategy: How to Turn a $200K Equipment Purchase Into a $70K Tax Break

Learn how dental practices use Section 179 and bonus depreciation to convert major equipment purchases into immediate tax deductions worth tens of thousands of dollars.

Tom Woolley, MBA 11/10/25
How to Avoid an IRS Audit: What Business Owners Need to Know

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
Online Sales Tax for Business Owners: What You Need to Know About Nexus and Compliance

Online Sales Tax for Business Owners: What You Need to Know About Nexus and Compliance

The 2018 South Dakota v. Wayfair Supreme Court decision changed everything for online sellers. Here is what nexus means today, which states require you to collect sales tax, and how to stay compliant.

Tom Woolley, MBA 11/3/25
Best Retirement Plan Options for the Self-Employed: SEP IRA, Solo 401(k), and Beyond

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

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

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

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)

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

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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