The Calculated Moves Blog

Playbooks for family businesses that mean to win

Tax, profit, and growth strategy — straight talk from CPAs who actually run a business. 897 articles and counting.

Jul 1, 2026

Owner's Draw vs. Payroll: How to Pay Yourself as a Small Business Owner the Smart Way

Owner's draw vs. payroll: learn how to pay yourself as a small business owner, reduce self-employment taxes with an S corp, and avoid costly IRS mistakes.

Jun 19, 2026

Family Business Exit Strategy: 5 Steps to Sell Smart, Save on Taxes & Protect Your Legacy

Learn the 5 critical steps to a family business exit strategy that maximizes value, minimizes taxes, and protects your legacy. Start planning your exit today.

Jun 2, 2026

Why Your First Hire Should Be an Executive Assistant (Not What You Think)

Most business owners get their first hire wrong. Learn why an executive assistant or virtual assistant should be your first hire to scale faster and build wealth.

May 21, 2026

LLC Operating Agreement: The One Document Every Business Owner Needs Before Launching

An LLC operating agreement protects your ownership, profits, and partnerships. Learn what to include, common mistakes to avoid, and why this document is essential.

Feb 21, 2026

Roth IRA: Smart Strategy or Overhyped Tax Trap?

Before you buy into the “Roth is tax-free forever” hype, consider that paying taxes at your highest rate today on the assumption future rules won’t change may quietly cost you thousands, which is why smart business owners rely on strategy and math, not marketing slogans.

Feb 18, 2026

Cash Back vs Travel Credit Cards for Business Owners | Which Is Actually Better?

If you’re paying hefty annual fees to earn travel points on business expenses, you may be losing thousands in real, usable cash flow compared to simple cash back, and for most business owners, money in the bank today beats “free” flights tomorrow.

Jan 28, 2026

Avoid These 3 Costly Bookkeeping Mistakes Now!

If you think bookkeeping is simple, these three costly mistakes could be quietly draining your profits and increasing your tax bill—and this article shows you how to fix them fast.

Jan 17, 2026

The Right Way to Give Pay Raises in a Small Business

If giving raises feels like a mix of guilt, guesswork, and quiet panic, this article shows how small businesses can ditch time-based pay bumps, reward real value instead, and build a smarter, stress-free raise system that motivates employees and protects profits.

Jan 13, 2026

Do I Have to Make Estimated Payments? What If I Don’t?

Estimated tax payments aren’t the IRS’s way of ruining your life—but ignoring them (or blindly overpaying) might be, and this article breaks down the smarter, legal way modern entrepreneurs can protect cash flow, avoid penalties, and stop letting taxes steal time, sleep, and sanity.

Jan 13, 2026

Estimated Tax Payments Explained: How Real Estate Investors Can Keep More Cash and Avoid IRS Penalties

Estimated tax payments don't have to drain your cash. Learn IRS safe harbor rules, penalty thresholds, and smart strategies to keep more money working for you.

Jan 4, 2026

The Perfect Banking Setup for Your Small Business

If your business banking runs on one checking account, a “future tax savings” account, and pure optimism, this article shows how a smarter banking setup can eliminate financial chaos, reduce taxes, and finally give modern entrepreneurs the clarity (and sanity) they deserve.

Dec 22, 2025

Why a Bookkeeper Isn’t Enough to Grow Your Business

If you think having a bookkeeper means your finances are “covered,” this article will show you why that mindset keeps you stuck in maintenance mode—and how a strategic CPA-level plan helps you grow faster, keep more profit, and keep Uncle Sam off your back.