Today’s Theme: Tax Planning Strategies for Medium-Sized Businesses

Welcome! We’re diving into practical, confidence-boosting tax planning strategies for medium-sized businesses. Expect clear ideas, real stories, and actionable steps to help you pay fairly, protect cash, and grow. Share your questions, subscribe for updates, and join the conversation as we turn tax from uncertainty into strategic advantage.

Map Your Tax Terrain Before You Move

S corporation, C corporation, or LLC taxed as a partnership—each choice shapes payroll taxes, distributions, fringe benefits, and exit outcomes. Revisit structure annually as profits, owners, or investors change. Comment with your current structure and why you chose it.

Deductions and Credits that Protect Cash Flow

Section 179, bonus depreciation, and cost segregation can front-load deductions for equipment and building components. Pair with a capitalization policy so repairs and improvements are treated consistently. Share your biggest fixed asset purchase planned this year.

Deductions and Credits that Protect Cash Flow

Process improvements, custom software, and manufacturing experiments often qualify. Track time, materials, and testing iterations early, not after year-end. Ask production managers to log iterations weekly. Comment if your team is experimenting but not documenting yet.

Compensation and Benefits: Reward People, Optimize Taxes

Owner pay needs to be defendable against payroll tax scrutiny, especially for S corporations. Balance wages and distributions with evidence like market surveys. Drop a question about your industry’s pay benchmarks and we’ll highlight useful sources.

Compensation and Benefits: Reward People, Optimize Taxes

Safe Harbor 401(k), profit sharing, and cash balance plans can shift taxable income into tax-advantaged savings while boosting retention. Model contributions versus nondiscrimination testing outcomes. Subscribe for our comparison checklist to start conversations internally.

Managing Growth Across States and Borders

Economic nexus means revenue and transaction counts can trigger filing obligations even without physical presence. Implement product taxability mapping and exemption certificate management. Comment with your top marketplace or channel and we’ll share common pitfalls.

Managing Growth Across States and Borders

When related entities share services, space, or staff, formalize chargebacks with a consistent markup and documentation. Even domestic groups benefit. Ask about simple templates if you’re splitting costs informally today.

Deals, Investments, and Exit Readiness

Buyers want a step-up; sellers chase capital gains treatment. Elections like 338(h)(10) can balance interests. Build a side-by-side after-tax model before you sign a letter of intent. Ask for our modeling outline if a deal is on your horizon.

Deals, Investments, and Exit Readiness

Net operating losses and credits can be golden—unless limited by ownership changes and state rules. Track equity movements, maintain schedules, and test utilization regularly. Subscribe to get reminders on common limitation triggers.

Controls, Documentation, and Tax-Savvy Technology

Close the Books with a Tax Lens

Build checklists that capture capitalization thresholds, sales tax coding, and accrued bonuses each month. Align GAAP and tax where practical. How many days is your monthly close? Comment, and we’ll share time-saving ideas from peers.

Automate What Hurts the Most

Expense management with receipt OCR, AP automation, and integrated sales tax engines cut errors and audits. Use dashboards for estimates versus actuals. Subscribe for our tech stack map tailored to medium-sized operators.

Be Audit-Ready Every Week

Keep written policies, capitalization rules, board minutes, R&D logs, and nexus analysis in a living digital binder. Set retention schedules. Tell us which document is hardest to maintain, and we’ll prioritize templates next.