Why this matters:
Startup founders don’t fail because of taxes, but plenty of them get hit with penalties, lose credibility with investors, or burn cash fixing mistakes. Staying compliant is about protecting your runway and building trust.
Here’s the expanded checklist that covers everything from incorporation to daily habits.
☑ Incorporate in Delaware (C-Corp is the standard for VC-backed startups)
File your Certificate of Incorporation with Delaware Division of Corporations
Authorize enough shares (commonly 10M) for flexibility
☑ File and record your EIN (Employer Identification Number)
Needed for banking, payroll, and taxes
☑ Issue Founder Stock + file 83(b) Elections
Must be done within 30 days of stock grant
Prevents massive tax bills later
☑ Draft and adopt Bylaws or Operating Agreement
Governs how your company operates
Investors will ask for this
☑ Maintain a cap table and board resolutions
January 31 → Send W-2s to employees & 1099-NECs to contractors
March 1 → File Delaware Franchise Tax + Annual Report
April 15 → File Form 1120 (corporate income tax return)
Or file Form 7004 for a 6-month extension (new due date: October 15)
Quarterly (Apr 15, Jun 15, Sept 15, Jan 15) → Pay estimated corporate taxes
Year-End → Renew registered agent and review compliance status
☑ Register with IRS and state for payroll taxes (if you have employees)
☑ File Form 941 (quarterly payroll tax return)
☑ File Form 940 (annual federal unemployment tax return)
☑ Issue W-2s to employees by January 31
☑ Collect W-9s from every contractor before payment
☑ Send 1099-NECs to contractors you paid $600+ in a year
☑ Check state-level contractor rules (e.g., CA AB5)
☑ Keep business and personal finances 100% separate
Use a dedicated business bank account and credit card
☑ Track & categorize expenses
Software & tools (Slack, Notion, AWS)
Marketing & sales (ads, website, design)
Travel & lodging (flights, hotels, conferences)
Equipment & depreciation (laptops, monitors, servers)
☑ Record every transaction in your accounting system (QuickBooks, Xero, etc.)
☑ Store receipts for IRS audit defense (digital copies are fine)
☑ R&D Tax Credit
If you’re building new software, tech, or prototypes → you may qualify
Can offset up to $250,000 of payroll taxes annually
☑ Section 179 Deduction
Deduct equipment purchases (up to IRS limits) in the same year
☑ Startup Cost Amortization
Deduct up to $5,000 of startup costs in year 1, amortize the rest
☑ If foreign-owned (>25%): File Form 5472 + pro forma Form 1120
☑ File FBAR (Foreign Bank Account Report) if >$10,000 held abroad
☑ Register for state-level foreign qualification if operating outside Delaware
☑ Watch for sales tax obligations (economic nexus laws vary by state)
☑ Check cash flow daily
Runway = survival. Always know your bank balance.
☑ Talk to customers
Tax write-offs won’t save you if you don’t have product-market fit.
☑ Automate and delegate ops
Use software for bookkeeping, payroll, invoicing, and 1099s
☑ Review books monthly
Spot errors early
Compare budget vs. actuals
Prep for investor updates
☑ Reflect daily
What worked today?
What didn’t?
What’s the priority for tomorrow?
❌ Mixing personal and business expenses
❌ Forgetting to file 83(b) within 30 days
❌ Missing Delaware Franchise Tax (March 1)
❌ Waiting until April 14 to start tax prep
❌ Assuming contractors don’t need 1099s
❌ Not filing when “no revenue” — IRS still requires returns
☑ Close books and reconcile accounts
☑ File annual reports (state + IRS)
☑ Review tax strategy with a CPA
☑ Prepare board & investor-ready financials
☑ Update startup tax calendar for next year
Staying compliant isn’t glamorous, but it’s one of the highest-leverage things you can do. It saves you money, stress, and credibility.
Think of this checklist as your startup’s shield:
Protects from IRS penalties
Builds investor trust
Keeps your head clear for growth
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