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Today CFO Blog — Tax Strategy & Business Finance Insights

The Mid-Year Reset: How to Use Your Q1 Numbers to Reshape the Rest of 2026

The Mid-Year Reset: How to Use Your Q1 Numbers to Reshape the Rest of 2026

First quarter is in the books. You still have nine months to change the year. Here's the simple mid-year reset small business owners use to fix what's not working before it costs them.

Tom Woolley, MBA 4/30/26

Featured Posts

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

Tom Woolley, MBA 5/5/26

The May Cleanup: What Your 2025 Tax Return Just Told You About Your Books

Tom Woolley, MBA 5/4/26

Building a Summer Cash Buffer: Why May Is the Best Month to Stress-Test Your Working Capital

Tom Woolley, MBA 5/1/26

How a UK SaaS Company Got a Reliable US Financial Operation Without Hiring a Single Stateside Accountant

Tom Woolley, MBA 3/9/26

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

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

CFO Advisory

The Mid-Year Reset: How to Use Your Q1 Numbers to Reshape the Rest of 2026

The Mid-Year Reset: How to Use Your Q1 Numbers to Reshape the Rest of 2026

First quarter is in the books. You still have nine months to change the year. Here's the simple mid-year reset small business owners use to fix what's not working before it costs them.

Tom Woolley, MBA 4/30/26
How a UK SaaS Company Got a Reliable US Financial Operation Without Hiring a Single Stateside Accountant

How a UK SaaS Company Got a Reliable US Financial Operation Without Hiring a Single Stateside Accountant

Sysmax needed a complete US finance department — bookkeeping, AR/AP, payroll, banking, and cross-border intercompany accounting — without the overhead of building an internal team. Here's how Today CFO made it happen.

Tom Woolley, MBA 3/9/26
When Should a Startup Hire a CFO? 7 Clear Signals

When Should a Startup Hire a CFO? 7 Clear Signals

Most startups wait too long to bring in CFO-level expertise. Here are 7 signals that tell you exactly when your startup needs a CFO, and what happens when you ignore them.

Tom Woolley, MBA 11/4/25
Why Construction Companies Need a CFO: Job Costing, Cash Flow, and Growth

Why Construction Companies Need a CFO: Job Costing, Cash Flow, and Growth

Construction companies face unique financial risks. Learn how a CFO addresses job costing accuracy, WIP reporting, subcontractor management, and cash flow gaps.

Tom Woolley, MBA 11/3/25
View All 21 CFO Advisory Posts

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Tax Planning

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

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

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
View All 20 Tax Planning Posts

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Bookkeeping

The May Cleanup: What Your 2025 Tax Return Just Told You About Your Books

The May Cleanup: What Your 2025 Tax Return Just Told You About Your Books

Tax season just exposed every weak spot in your books. May is the right time to fix it — while the pain is fresh, your bookkeeper has time, and the IRS is watching closer than ever.

Tom Woolley, MBA 5/4/26
What Records Does a Small Business Need to Keep? (The Complete Retention Guide)

What Records Does a Small Business Need to Keep? (The Complete Retention Guide)

Maintaining accurate business records is a legal requirement — and it can save your business in an audit. This complete retention guide tells you exactly what records to keep, for how long, and in what format to stay compliant, protect your deductions, and give yourself peace of mind.

Tom Woolley, MBA 11/4/25
Bookkeeper, Accountant, or CFO: Which Does Your Business Actually Need?

Bookkeeper, Accountant, or CFO: Which Does Your Business Actually Need?

Bookkeeper, accountant, CPA, controller, CFO — these terms get used interchangeably, but they describe very different roles with very different costs and capabilities. This guide clarifies each role, what it costs, and exactly which one your business needs at your current stage.

Tom Woolley, MBA 11/4/25
How Accounting Automation Improves Small Business Efficiency in 2025

How Accounting Automation Improves Small Business Efficiency in 2025

Accounting automation is redefining small business finance. Learn how to improve efficiency, accuracy, and decision-making by automating your accounting workflows in 2025 — including which tools to use, how to implement them, and the real-world impact on your bottom line.

Tom Woolley, MBA 11/3/25
View All 25 Bookkeeping Posts

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Cash Flow

Building a Summer Cash Buffer: Why May Is the Best Month to Stress-Test Your Working Capital

Building a Summer Cash Buffer: Why May Is the Best Month to Stress-Test Your Working Capital

Many small businesses bleed cash from June through August. Rates are still high. Customers are paying slower. Here's how to model the summer dip in May — before it shows up in your bank account.

Tom Woolley, MBA 5/1/26
How to Budget During Financial Uncertainty: A Business Owner's Guide

How to Budget During Financial Uncertainty: A Business Owner's Guide

When the economy shifts and revenue becomes unpredictable, most business budgets fall apart. Learn how to build a flexible, scenario-based budget that protects your cash flow, preserves your team, and keeps you positioned to grow when conditions stabilize.

Tom Woolley, MBA 11/3/25
Cash Flow Forecasting: What It Is and Why Your Business Needs It

Cash Flow Forecasting: What It Is and Why Your Business Needs It

Cash flow forecasting lets you see exactly when money will enter and leave your business so you can avoid shortfalls, plan for growth, and make smarter financial decisions. Learn the types of forecasting, how to build one, and the costly mistakes to avoid.

Tom Woolley, MBA 11/3/25
How to Cut Business Costs Without Cutting Corners: 6 Smart Strategies

How to Cut Business Costs Without Cutting Corners: 6 Smart Strategies

Strategic cost reduction is not about slashing everything in sight — it is about finding waste, renegotiating what you can, and making smarter decisions about where you invest. Here are 6 proven strategies to reduce costs without compromising your business's ability to grow.

Tom Woolley, MBA 11/3/25
View All 13 Cash Flow Posts

Complete Guides

In-depth resources covering everything you need to know

Tax Planning

The Complete Guide to Proactive Tax Planning for Business Owners

Most business owners overpay $10K+ annually. Learn how to pay less legally — year-round, not just at filing.

25 min read Read Guide
CFO Advisory

The Complete Guide to Fractional CFO Services

Discover what fractional CFO services actually include, what they don't, and when your business truly needs one.

35 min read Read Guide
Bookkeeping

The Complete Guide to Business Bookkeeping

Master small business bookkeeping. Learn when to DIY vs. outsource, which software to choose, and best practices.

30 min read Read Guide
Cash Flow

The Complete Guide to Cash Flow Planning

Master the 13-week cash flow forecast, improve receivables, and transform from firefighting to forecasting.

35 min read Read Guide

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