First-Time Business Owner

Tax basics for new business owners

First-Time Business Owner: Your Step-by-Step Tax Action Plan

A visual step-by-step tax action plan for first-time business owners. Covers entity selection, EIN registration, self-employment tax, quarterly estimated payments, S-corp election timing, and year-end tax moves.

In-Depth Guides (5)

Comparisons (1)

CPA vs. Bookkeeper: What Each Does and When You Need to Upgrade

Understand the differences between CPAs and bookkeepers -- what each does, certification levels, cost comparison, and the signs it is time to upgrade from bookkeeping to CPA-level oversight.

Explainers (2)

Section 83(b) Elections: The 30-Day Deadline That Could Save You Millions

A Section 83(b) election lets you pay tax on restricted stock at grant instead of vesting. The 30-day filing deadline is absolute. Learn how it works, when it saves money, and how to file.

What Is an S-Corp Election and Should Your Business Make One?

An S-Corp election lets your LLC or corporation be taxed under Subchapter S, cutting self-employment taxes on profits above a reasonable salary. Learn eligibility, deadlines, and trade-offs.

Checklists (1)

First-Time Business Owner's Tax Calendar: Deadlines You Can't Miss

A month-by-month tax calendar for new business owners covering quarterly estimated payments, payroll deposits, annual filing deadlines by entity type, information returns, and the penalties for missing each one.

Quick Guides (32)

$100K-$250K Revenue

Choose this if your business generates $100,000 to $250,000 in annual revenue -- the range where the S-corp election almost certainly pays for itself and...

$25K-$50K Revenue

Choose this if your business is generating $25,000 to $50,000 in annual revenue -- past the hobby threshold but not yet at the level where entity...

$50K-$100K Revenue

Choose this if your business generates $50,000 to $100,000 in annual revenue -- the range where entity structure and retirement planning start delivering...

Choose this if you have hired between one and five W-2 employees.

Choose this if you have six or more W-2 employees on payroll.

Accounting Software

Choose this if you use QuickBooks, Xero, FreshBooks, Wave, or similar accounting software to track your business finances.

Choosing the Right Entity

Choose this if you are unsure whether to operate as a sole proprietorship, LLC, S-corporation, or C-corporation.

Didn't Know About Estimated Payments

Choose this if you did not realize self-employed individuals must make quarterly tax payments.

E-Commerce Business

Choose this if you sell products primarily through online channels -- your own website, Amazon, Etsy, Shopify, or other digital marketplaces.

Inconsistent Estimated Payments

Choose this if you have made some quarterly estimated payments but missed others or paid inconsistent amounts.

Independent Contractors Only

Choose this if everyone who works for you is an independent contractor, not a W-2 employee.

Making Estimated Payments

Choose this if you are already making quarterly estimated tax payments to the IRS and your state.

View all 32 quick guides →

Your Professional Team

CPA

Always

Entity selection, estimated payments, payroll setup, and deduction optimization

Business Attorney

Sometimes

Entity formation, operating agreements, and contract review

Learn more →

Bookkeeper

Often

Day-to-day transaction recording, bank reconciliation, and receipt management

Learn more →

How to build your complete financial team →