The 30-Day Business Setup Checklist: What to Do Before Your First Dollar

The first 30 days set the tone for everything

Most first-year business owners spend their first month chasing clients and forget about the infrastructure. Then March arrives and they’re reconstructing six months of transactions from a bank account full of mixed personal and business charges, trying to remember what the Costco charge was for, and asking their CPA to clean up a mess that would have taken two hours to prevent.

This checklist is built for the first 30 days. Not because these things are hard, but because the window where they’re easy closes fast. Do them now, in order, and you’ll spend the rest of the year focused on your actual business.

Week 1: The four things that can’t wait

☐ Get your EIN

IRS.gov/ein. Free. Five minutes. Do it today.

An EIN is the federal tax ID for your business — you need it to open a bank account, file business taxes, and pay any contractors. Even as a sole prop, you should have one so you’re not handing out your Social Security number to every client who asks for a W-9.

The online application is available Monday–Friday, 7 a.m.–10 p.m. Eastern. Download and save the confirmation letter immediately — the IRS doesn’t give you an easy way to retrieve it later.

☐ Open a dedicated business bank account

Every business payment goes into this account. Every business expense comes out of it. Your personal spending never touches it.

This is not optional — it’s the foundation of clean bookkeeping. Mixed accounts create hours of cleanup at tax time, muddy your liability protection if you have an LLC, and invite IRS scrutiny.

Most major banks offer no-fee or low-fee business checking. Bring your EIN, your state formation documents (if you have an LLC), and a government ID. Some banks (Mercury, Relay, Bluevine) let you open online in minutes.

☐ Open a tax savings account

Open a second business savings account — separate from operating checking — and label it “Tax Reserve.” Transfer 25–30% of every payment you receiveinto this account the day it arrives. Don’t touch it.

This is the single habit that prevents the most common first-year crisis: a tax bill you can’t pay. Revenue is not all yours. A third of it belongs to the government. Keep it separate before you spend it.

☐ Know your first quarterly estimate deadline

As a self-employed business owner, the IRS expects quarterly estimated payments — not annual. The due dates are April 15, June 16, September 15, and January 15. If you’re starting mid-year, figure out which quarter you’re in and set a calendar reminder for the next deadline.

You won’t know exactly what to pay yet — that’s what the quarterly estimate planner is for. But knowing the deadline exists prevents the penalty-triggering surprise of missing it entirely.

Week 2: Get your financial infrastructure in place

☐ Choose and set up bookkeeping software

Connect your business bank account to your bookkeeping software so transactions import automatically. Every dollar in and out gets categorized. Do this now while there are only a few transactions — not in December when there are hundreds.

If you’re not sure which to use: Wave is free and works well for simple sole props. QuickBooks Online Simple Start ($30/month) is the safest default for most businesses. Ask your CPA before committing if you have one.

☐ Set up a basic chart of accounts

Your bookkeeping software comes with a default chart of accounts — a list of categories for every type of income and expense. Review the list and make sure it reflects your actual business. A personal trainer doesn’t need “Cost of Goods Sold.” A salon does. Delete what doesn’t apply. Add what’s missing.

☐ Create your first invoice template

Every client engagement starts with an invoice. Set up a template in your bookkeeping software or invoicing tool with your business name, EIN, payment terms (due on receipt, net 30, etc.), and accepted payment methods. A professional invoice builds trust and gets paid faster.

☐ Set up payment processing

How will clients pay you? For service businesses: Stripe (invoicing, credit cards, ACH) or Square (in-person + invoicing). For product businesses: Square or Shopify. For professional services: Stripe, QuickBooks Payments, or ACH via your bank.

Processing fees (Stripe charges 2.9% + 30¢ per transaction) are a fully deductible business expense. Route all payments into your business checking account — not personal.

Week 3: Protect the business

☐ Get a general liability insurance quote

General liability insurance covers you if a client claims your business caused them property damage or bodily injury. For most service businesses: $30–80/month. For higher-risk industries: more.

You may also need: professional liability / errors and omissions (if you give professional advice), commercial property (if you have a physical location), or workers comp (required the moment you have an employee in California).

A quick quote from a business insurance broker (Hiscox, Next Insurance, and Thimble are popular online-first options) takes 10 minutes.

☐ Set up mileage tracking (if you drive for work)

If you drive to client sites, make deliveries, or use your car for any business purpose, you can deduct either the standard mileage rate (67¢/mile in 2024) or actual expenses. Either way, you need a mileage log — the IRS requires date, destination, purpose, and miles for every trip.

Apps that do this automatically: MileIQ (swipe right for business, left for personal), Stride (free, designed for gig workers), or QuickBooks Mileage(if you’re already in QBO). Start the day you drive for business — you can’t reconstruct mileage from memory.

☐ Start the receipt habit

Every business expense over $75 needs a receipt. Every meal needs a receipt, regardless of amount. The habit: take a photo immediately, email it to your bookkeeping software (QuickBooks and Xero both provide an email address for receipt capture), and add a quick note if it’s a meal (“Lunch with Sarah Chen — discussed Q3 contract”).

Three seconds of documentation protects every deduction you’ll claim. Build the habit now when the transactions are simple.

Week 4: The conversations that matter

☐ Talk to a CPA — before you get too busy

One hour with a CPA in your first month is worth ten hours of cleanup later. What to bring to that conversation:

• Your expected revenue for the year (a rough estimate is fine)
• Your business structure (sole prop, LLC — or what you’re thinking about)
• Any other income (W-2, spouse income, investments)
• Whether you have employees now or plan to

A CPA can tell you: whether an S-corp makes sense at your expected income level, what your quarterly estimates should be, whether you qualify for a solo 401(k) this year, and what expenses you might be missing. The clarity from one conversation often pays for itself many times over.

The best time to talk to a CPA is before your first dollar. The second best time is right now.

☐ Set your monthly financial review reminder

The last thing on this checklist is a calendar reminder, recurring: last Friday of every month, 20 minutes, review and categorize the month’s transactions.

That’s the whole system. If you do the setup above and spend 20 minutes every month keeping it current, you will never scramble at tax time. Your books will be clean, your quarterly estimates will be accurate, and your CPA will have nothing to clean up before filing.

What comes next

Once the basics are in place, your financial questions change. Month two and beyond:

• Quarterly estimates: Use your actual profit figures to calculate the right payment amount — not a guess. The quarterly estimate planner walks through this.
• Retirement contributions: A solo 401(k) can shelter up to $70,000 in 2025. You can open one any time during the year but must establish it by December 31. Start thinking about this in Q2.
• Entity structure: If profit is tracking toward $60k+ this year, run the S-corp breakeven calculator. The March 15 deadline for next year’s election isn’t far away.
• Year-end planning: Equipment purchases before December 31 qualify for Section 179 deduction. Retirement contributions can wait until the tax filing deadline. Know the calendar before Q4.