Build Smarter: Tax Planning and Optimization for Entrepreneurs

Welcome, founders and independent builders. Here, practical strategy meets real stories so you can keep more of what you earn without losing sleep or momentum. Subscribe, ask questions, and grow with us. Chosen theme: Tax Planning and Optimization for Entrepreneurs.

LLC, S Corporation, or C Corporation?

An LLC offers flexibility and simplicity, an S corporation can reduce self-employment taxes with reasonable wages, and a C corporation may unlock QSBS potential. Share your current setup, and we’ll send entity-specific checklists tailored to your stage.

Reasonable Compensation Without Guesswork

S corporation owners must pay themselves a reasonable salary. Anchor pay to duties, time, profitability, and third-party data. Comment with your industry and revenue range if you want a practical salary framework and examples used by founders like you.

QSBS: Dreaming of a Tax-Free Exit

Qualified Small Business Stock may allow significant capital gains exclusion if you qualify and hold five years. We’ve seen founders structure early for QSBS and later thank past selves. Ask for our QSBS preflight checklist before your next funding conversation.

Section 199A QBI Deduction in Plain English

Many pass-through owners may deduct up to 20% of qualified business income, subject to wage and property tests. Optimize payroll, contractor mix, and capitalization to avoid phase-outs. Drop your questions below and we’ll tackle common pitfalls in a follow-up.

R&D Credit for Builders and Tinkerers

If you develop software, improve processes, or experiment with prototypes, the R&D credit could offset payroll or income taxes. Keep contemporaneous notes, tickets, and commits. Subscribe for our founder-friendly template that maps sprints to qualified activities clearly.

Depreciation: Bonus vs. Section 179

Equipment, servers, and certain software can be expensed quickly via Section 179 or bonus depreciation, which currently phases down in coming years. Time purchases strategically around profitability. Share your upcoming buys, and we’ll outline an optimal depreciation mix.

Master Timing and Cash Flow

Cash basis simplifies taxes and can delay income recognition, while accrual shows true performance and helps with financing. Choose intentionally, not by default. Tell us your billing pattern, and we’ll recommend the lens that supports smarter tax timing.

Master Timing and Cash Flow

Avoid penalties by paying quarterly using safe harbor rules, typically 100% of last year’s tax or 110% for higher incomes. Automate transfers. Ask for our calendar and calculator to forecast confidently and protect your runway from painful surprises.

Master Timing and Cash Flow

Accelerate deductible expenses before year-end, defer invoicing strategically, and prepay qualified costs when appropriate. One client shifted a contract by two weeks and saved enough to fund a marketing test. Share scenarios, and we’ll weigh pros and cons together.

Home Office and the Augusta Rule

A qualifying home office deduction can be meaningful when substantiated. Some owners legally rent their homes to the business for meetings under the Augusta rule in certain cases. Curious if you qualify? Comment with your setup for a tailored documentation checklist.

Accountable Plans: Reimburse Yourself Properly

Reimburse business expenses to owners and employees tax-efficiently with an accountable plan. Clear policies and timely receipts prevent taxable fringe benefits. Subscribe for our policy template used by scrappy teams scaling without tripping compliance wires.

Travel Deductions Without Red Flags

Combine conferences with client visits, document business purpose, and separate personal days. Keep itineraries, agendas, and receipts matched to outcomes. Share your next trip plan, and we’ll help structure it to maximize deductions and minimize audit headaches.

Beyond Borders: States and International

Hiring a remote contractor, storing inventory, or crossing economic thresholds can create state income tax nexus. Keep a simple nexus log. Comment with your footprint, and we’ll flag states where registration or apportionment should move to the top of your list.

Beyond Borders: States and International

Rules vary widely, especially for software and subscriptions. Marketplace facilitator laws help some sellers, but not SaaS. We publish state-by-state updates—subscribe and tell us your product model to receive a targeted sales tax survival sheet tailored to you.

Audit-Ready Habits and Tools

Tie every deduction to a business purpose, attach receipts, and maintain meeting notes. Future you—during diligence or audits—will be grateful. Post a comment about your messiest category, and we’ll share a simple tagging framework you can apply today.

Audit-Ready Habits and Tools

Use bank rules, receipt apps, mileage trackers, and project links to keep records in sync. Reconcile weekly. Want our favorite tools by budget? Subscribe and tell us your stack so we can recommend a frictionless workflow tailored to your size.

Audit-Ready Habits and Tools

Schedule reviews to adjust estimates, revisit salaries, time purchases, and optimize retirement contributions. One founder’s 30‑minute quarterly cadence saved five figures last year. Share your quarter-end date, and we’ll send a planning checklist aligned to your calendar.