Legal & Formation Playbook
Disclaimer: This is educational context only — not legal advice. Always consult a licensed attorney for entity formation, equity, and compliance decisions.
Entity Choice
LLC vs C-Corp vs S-Corp
| Factor | LLC | C-Corp (Delaware) | S-Corp Election |
|---|---|---|---|
| VC fundable | No (VCs typically won't invest) | Yes | No (ownership restrictions) |
| Pass-through taxes | Yes | No (double taxation) | Yes (with restrictions) |
| QSBS eligibility | No | Yes | No |
| Self-employment tax | Higher | Lower at scale | Lower (reasonable salary) |
| Best for | Bootstrapped, services, lifestyle | VC-backed, high-growth, exits | Profitable small businesses |
| Complexity | Low | High | Medium |
| Stock options | No (can use profits interests) | Yes (ISO, NSO) | Limited |
| Max shareholders | Unlimited | Unlimited | 100 (US residents only) |
Decision rules:
- Raising VC within 24 months? → Delaware C-Corp. No exceptions.
- Bootstrapping a services business? → State LLC. Simple and cheap.
- Profitable, staying small, want tax savings? → LLC with S-Corp election (consult CPA).
- International founder? → Delaware C-Corp (globally recognized, needed for US banking/investors).
S-Corp Election — When It Makes Sense
An S-Corp election lets you avoid double taxation while maintaining corporate structure. The key benefit: you pay yourself a "reasonable salary" (subject to payroll taxes) and take remaining profits as distributions (no self-employment tax).
When to elect S-Corp:
- You're profitable and taking $80K+ in distributions per year
- You're not raising VC (S-Corps have ownership restrictions)
- All owners are US residents
- You have fewer than 100 shareholders
How: File IRS Form 2553 within 75 days of formation (or by March 15 for existing entities).
Formation Quick Reference
State LLC Formation (General Steps)
- Choose a business name → check availability at your state SOS website
- File Articles of Organization → typical fee $50-$300 depending on state
- Designate a Registered Agent (yourself or a service ~$50-$150/yr)
- Apply for EIN → irs.gov/ein (free, instant online)
- Open a business bank account (Mercury, Relay, or local bank)
- Draft an Operating Agreement (critical even if not legally required)
- Apply for required business licenses (varies by city/county)
Delaware C-Corp Formation
DIY Services:
- Stripe Atlas ($500) — incorporation + EIN + bank + stock issuance (fastest)
- Clerky ($399+) — startup-optimized, attorney-reviewed docs
- Firstbase ($399) — includes registered agent + compliance tracking
- Gust Launch (free) — basic formation
Attorney: $1,500-$5,000 for full startup package (recommended if multiple co-founders or complex equity)
Steps after formation:
- Issue founder stock immediately at par value
- File 83(b) election within 30 days (see below)
- Assign all IP to the company in writing
- Set up vesting agreements for all founders
- Register as foreign corporation in your home state (if not Delaware)
- Open bank account + apply for EIN
- Pay Delaware franchise tax annually (~$400 minimum, due March 1)
International Founders — US Entity Formation
If you're based outside the US and want to build a US-structured startup:
Why Delaware C-Corp: Globally recognized, required by most US VCs, enables US banking and payment processing.
Key considerations:
- You don't need to live in the US to form a Delaware C-Corp
- You DO need a US registered agent (included with Stripe Atlas, Firstbase, etc.)
- US bank account: Mercury and Relay accept foreign founders; some require US address
- EIN: Apply via IRS Form SS-4 (fax or mail if no SSN/ITIN; services like Stripe Atlas handle this)
- Tax obligations: You may owe US tax on US-source income; consult an international tax advisor
- Visa considerations: Forming a US entity does not grant visa status; consider O-1, E-2, or L-1 visas
Common setup for international founders:
- Delaware C-Corp via Stripe Atlas ($500)
- US bank account via Mercury
- Stripe for payment processing
- US-based registered agent (included with formation service)
- International tax advisor to handle cross-border obligations
Equity & Vesting
Standard Founder Vesting
- 4 years total with a 1-year cliff
- Cliff: No stock vests until 12 months; then 25% vests immediately
- Monthly vesting after cliff: 1/48 per month for remaining 36 months
- Set this up BEFORE taking any outside money
- All founders vest, including the CEO. No exceptions.
83(b) Election — Do Not Skip This
- File within 30 days of receiving restricted stock. No extensions.
- Tells the IRS you want to be taxed now on the low early value
- Without it, every vesting date is a taxable event — potentially $100K+ in unnecessary taxes
- File with IRS via certified mail + keep a copy + file with company records
- This is one of the most costly mistakes founders make.
Employee Equity (Options)
- Standard: 10-15% option pool reserved for employees
- Options vest on the same 4yr/1yr cliff schedule
- Strike price = FMV at grant date (set by 409A valuation)
- Get a 409A valuation before issuing any options (required for compliance)
- Cost: ~$1K-$5K for early-stage 409A (Carta, Pulley, Preferred Return)
Equity Ranges by Role and Stage
| Role | Pre-Seed | Seed | Series A |
|---|---|---|---|
| Co-founder | 10-50% | N/A | N/A |
| CTO (if not co-founder) | 1-5% | 0.5-2% | 0.25-1% |
| First engineer | 0.5-2% | 0.25-1% | 0.1-0.5% |
| VP Engineering | N/A | 0.5-1.5% | 0.25-0.75% |
| VP Sales | N/A | 0.5-1% | 0.25-0.5% |
| First salesperson | 0.1-0.5% | 0.05-0.25% | 0.02-0.1% |
| Advisor | 0.1-0.25% | 0.05-0.15% | 0.01-0.1% |
SAFE Note
Simple Agreement for Future Equity — not a loan, not equity yet.
Key terms:
- Valuation cap: Max valuation it converts at. Lower cap = better for investor.
- Discount rate: Converts at a discount to the next round (typically 15-25%)
- Pro-rata rights: Right to invest in future rounds to maintain ownership %
- MFN clause: If you offer better terms to future investors, early SAFE holders get those terms too
Use YC's standard postmoney SAFE. Free at ycombinator.com/documents. Don't create custom terms early-stage — it spooks investors and costs legal fees.
Co-Founder Agreement Checklist
Before taking any money or writing any code together:
- [ ] Equity split (and rationale — written down)
- [ ] Vesting schedule for all founders
- [ ] IP assignment (all work belongs to the company)
- [ ] Decision-making authority (who decides what)
- [ ] What happens if a co-founder leaves (buyback rights)
- [ ] Compensation expectations (salary, deferred)
- [ ] Full-time commitment expectations
- [ ] Non-compete / non-solicit scope
A handshake agreement is not enough. Put it in writing.
Intellectual Property Basics
- All founders must assign IP to the company in writing before taking money
- Any code, designs, or inventions created for the company belong to the company
- Missing IP assignments kill deals — this is standard in every investor's due diligence
- File provisional patent applications for novel inventions before public disclosure
- See also:
ip/README.mdfor full IP strategy, patents, trademarks, and trade secrets
QSBS (Qualified Small Business Stock)
- Up to $10 million in federal capital gains tax exclusion
- Requires: C-Corp, original issuance (not secondary), held 5+ years
- Company must have < $50M in assets at time of issuance
- One of the most valuable tax benefits for early startup founders and investors
- State treatment varies: Some states (CA) don't conform; others (MO) do. Check your state.
Key Legal Resources
| Need | Resource |
|---|---|
| Entity formation | Stripe Atlas, Clerky, your state SOS website |
| SAFE / term sheet templates | ycombinator.com/documents |
| Startup-friendly law firms | Cooley, Gunderson, Wilson Sonsini, Orrick |
| IP assignment templates | Clerky, NVCA model docs |
| 409A valuation | Carta, Pulley, Preferred Return |
| Cap table management | Carta (funded) or LTSE Equity (early stage, free) |
| Free legal document generators | cooleygo.com, tsc.orrick.com |
> Disclaimer: This playbook provides educational information about legal structures and formation. It is not legal advice. Consult a licensed attorney before making entity formation, equity, and compliance decisions. Tax treatment varies by jurisdiction and individual circumstances — consult a CPA.
Nonpartisan informational resource for Missouri — District 2 — not legal, medical, or financial advice. Source: dougdevitre/access-to-business.
Paid for by Matt Grant for Congress.
