Startups move fast. Paperwork usually doesn’t. And that mismatch is where a lot of avoidable pain comes from—founder breakups, messy cap tables, “who owns the code?” fights, option grants that don’t hold up in diligence, and offer letters that accidentally create promises you never meant to make.
This post is a practical, founder-friendly map of the core employment + equity + IP agreements you should think about as you go from “we just incorporated” to “we’re hiring execs and prepping for an exit.” It’s not meant to turn you into a lawyer—it’s meant to help you avoid the landmines and ask better questions.
Table of Contents
- Why this stuff matters (more than you think)
- Stage 1: Formation — founders, equity, and IP
- Stage 2: Pre-financing — hiring early employees
- Stage 3: Post-financing — option pool, stock plan, 409A, and options
- Stage 4: Late-stage — exec agreements and RSUs
- Securities compliance: Rule 701, Reg D, and “restricted” confusion
- Practical checklists you can actually use
Why this stuff matters (more than you think)
Founders are builders. The instinct is to treat “legal” like a future problem. But employment and equity mistakes have a special talent for showing up at the worst possible time—usually when you’re:
- Trying to close your first real financing
- Recruiting a key hire who asks smart questions
- Negotiating an acquisition
- Fixing a founder conflict that should’ve been handled before feelings got involved
Most of the friction comes down to three buckets:
- Clarity — what people are being paid, what they’re getting, and what happens if they leave
- Ownership — who owns what (stock, options, IP, code, customer relationships)
- Compliance — wage/hour, tax rules, securities rules, and state-by-state differences
Founder reality check: the best time to document expectations is when everyone is optimistic and aligned. The second-best time is now.
Stage 1: Formation — founders, equity, and IP
At formation (or immediately after), your goal is to document three things:
- The founder employment relationship (yes, even founders)
- Founder equity (issued early, often with vesting)
- Founder IP assignment (so the company actually owns what it’s selling)
1) Founder employment relationship (offer letter + wage/hour reality)
Founders often skip formal offer letters because it feels weird to “hire yourself.” Totally understandable. Also risky.
A basic founder offer letter (or similar documentation) typically covers:
- Title and role (e.g., “CEO & Co-Founder”)
- At-will status (in most cases)
- Cash comp (even if it’s low early)
- Benefits (if any)
- Confidentiality / invention assignment obligations (often handled in a separate PIIA)
Wage and hour: founders are usually the company’s first employees. Minimum wage and overtime rules can still apply depending on role, exemptions, and state law. Some founders assume “we’re a startup” is an exemption. It isn’t.
In the real world, founders tend to pick one of these paths:
- Conservative / best practice: sign offer letters and actually pay compliant wages/salary.
- Middle path: sign offer letters with salary stated, but delay pay until financing (this can create tax and compliance complexity).
- Least conservative: no offer letter, just IP paperwork, no comp until financing (common, but it can create diligence and compliance issues later).
Simple rule: if you’re going to “delay” salary, don’t improvise. Talk to counsel and a tax advisor so you don’t accidentally create deferred compensation problems or wage claims later.
2) Founder equity (issue early; consider vesting)
Founder stock is usually common stock purchased early at a very low price (often par value). Issuing founder equity early matters because once value rises, the tax math gets uglier.
If there are multiple founders, vesting is your friend. It’s not about mistrust—it’s about building a fair system that protects the people who keep showing up.
The “default” startup vesting schedule is:
- 4 years total vesting
- 1-year cliff (nothing vests until month 12; then 25% vests)
- Monthly vesting after the cliff
Example (founder vesting in the real world):
Two founders split equity 50/50 with 4-year vesting and a 1-year cliff. One founder leaves at month 10. Because of the cliff, they leave with 0% vested equity. That feels harsh… until you realize the alternative is they leave with half the company after contributing less than a year.
3) Founder acceleration (single-trigger vs double-trigger)
Many founders ask for acceleration on a sale. The key idea is how it accelerates:
- Single-trigger: equity vests automatically upon a change in control.
- Double-trigger: equity accelerates only if there’s a change in control and the founder is terminated (or resigns for “good reason”) within a set period (often 12 months).
Acquirers and investors often dislike single-trigger acceleration because it can reduce incentives for founders to stay and help with transition. Double-trigger is more commonly accepted because it protects founders from getting acquired and then quickly pushed out.
4) Founder IP: if the company doesn’t own it, you don’t have a company
Investors and acquirers obsess over IP ownership for good reason. If the company can’t prove it owns (or has rights to) what it’s selling, the deal slows down or dies.
Two common tools show up here:
- TAA (Technology Assignment Agreement): assigns relevant pre-formation work (wireframes, prototypes, code, designs, etc.) into the company.
- PIIA (Proprietary Information and Inventions Assignment): assigns IP created during service to the company and sets confidentiality obligations.
Fast diligence test: if you can’t produce signed IP assignment docs for every founder (and ideally every early employee/contractor), expect friction later.
Stage 2: Pre-financing — hiring early employees
Before your first priced equity financing, you’re usually hiring with limited cash and lots of hope. This is where clean, simple documentation helps you recruit faster and avoid misunderstandings.
1) Pre-financing offer letters (simple, clear, not “BigCo”)
Early employee offer letters typically include:
- At-will statement
- Title, duties, and reporting structure
- Exempt vs non-exempt classification (this matters)
- Cash comp (salary/hourly, bonus, commissions if applicable)
- Work location (remote/hybrid), expected hours, moonlighting policy
- Benefits (if any)
- Conditions of employment (I-9, background checks, signing PIIA, start date)
- Tax/withholding basics and “please get your own tax advice” language
- Representation they’re not violating prior obligations (like another employer’s non-compete)
Plain English wins. The goal isn’t to sound sophisticated. The goal is that the employee understands what they’re agreeing to.
2) PIIA (the one agreement almost everyone should sign)
Startups often assume they “automatically” own employee-created inventions. Not always. A PIIA helps establish:
- Confidentiality obligations
- Invention assignment / works-made-for-hire concepts (as allowed by law)
- Return of company property and information
Best practice: make signing the PIIA a condition of employment and get it executed before the person starts seeing sensitive stuff.
3) Non-solicitation and non-competition (state law is a maze)
Many startups want to protect:
- Customer relationships
- Employee teams (no “raiding”)
- Trade secrets and roadmaps
Non-solicits (customers and employees) are often more enforceable than non-competes, but the rules vary dramatically by state and keep changing. Some states are highly restrictive or outright hostile to certain restrictive covenants. If you operate in multiple states or hire remote employees, don’t copy/paste—get advice tailored to where people actually work.
4) Early equity: restricted stock is common (and the 83(b) clock matters)
In the earliest days, employees sometimes purchase restricted stock at a very low value (often par value) subject to vesting. This can be attractive because it may avoid 409A complexities that come with options (more on that later).
But if someone receives restricted stock subject to vesting, they should learn about the 83(b) election, which generally must be filed within 30 days of the stock transfer. Missing that window can create nasty tax outcomes.
Example (83(b) in practice):
You give your first engineer restricted stock that vests over 4 years. If they file an 83(b) election on time when the shares are still worth almost nothing, they may avoid owing ordinary income tax as the shares vest and potentially shift upside into capital gains territory later. If they miss the deadline and the company grows, each vesting event can become a taxable moment at higher values—often with no liquidity to pay the tax.
Stage 3: Post-financing — option pool, equity plan, 409A, and options
Once you close your first priced equity financing (often your Series A, or sometimes a seed preferred round), your equity compensation system usually needs to level up.
The common sequence looks like this:
- Create or refresh an option pool
- Adopt an equity incentive plan
- Get a 409A valuation (typically via an independent valuation firm)
- Grant stock options under the plan with board approval
1) Option pool (why investors care)
Investors want the pool sized to cover your hiring plan until the next financing so you’re not coming back 90 days later asking to increase the pool and dilute everyone again.
Many first financings land with a pool somewhere around 10%–20% on a fully-diluted basis, but it varies based on hiring plans and the role of equity in compensation.
2) Equity incentive plan (the operating system for grants)
A solid plan answers questions like:
- Who is eligible?
- What awards are allowed (ISOs, NSOs, restricted stock, RSUs)?
- Who administers grants (board/committee)?
- What’s the standard vesting schedule?
- What happens on termination or change in control?
- What transfer restrictions apply?
Also: your board should approve the plan and grants. And depending on the plan design (especially if you want to grant ISOs), shareholder approval may be required.
3) 409A valuation (how you avoid “cheap options” problems)
Once the company has real value, granting options below fair market value can trigger serious tax penalties under Section 409A. The standard approach is to obtain an independent valuation of the company’s common stock and have the board rely on it when setting option exercise prices.
409A valuations are typically updated at least every 12 months, and sooner if a material event happens (like a new financing term sheet that implies a materially higher valuation).
4) Employee offer letters post-financing (the equity paragraph changes)
Post-financing offer letters usually shift from “you’re buying restricted stock” to “you’ll be granted stock options.” And the offer letter should be clear that:
- Any grant requires board approval
- The exercise price is set by the board (based on FMV at grant time)
- The employee will sign a formal award agreement later
5) Options 101: ISOs vs NSOs (what founders should know)
ISOs (Incentive Stock Options) can be attractive to employees because they may defer ordinary income tax and potentially convert upside into capital gains if holding period requirements are met—but they come with strict rules and can trigger alternative minimum tax (AMT) issues.
NSOs (Nonqualified Stock Options) are more flexible and can be granted to employees, contractors, and advisors, but generally create ordinary income tax at exercise on the “spread” (FMV minus exercise price), and the company has withholding obligations.
Founder-friendly framing: options are not “free equity.” They’re a right to buy shares later. Make sure employees understand exercise cost, taxes, and what happens if they leave.
Stage 4: Late-stage — exec agreements and RSUs
As the company grows, you start hiring leaders who are used to negotiated employment agreements. They’ll expect clarity on severance, termination, bonuses, and equity treatment.
1) Executive employment agreements (more negotiated, more consequences)
Compared to offer letters, exec agreements often cover:
- Term vs at-will structure
- Bonus plans and targets
- Outside activities and board roles
- Severance and/or garden leave concepts
- Change-in-control protections
- Dispute resolution (often arbitration)
These should be board-approved, and you should be intentional about internal consistency (you don’t want three different severance philosophies for three executives unless you meant to do that).
2) Equity at late-stage: when RSUs start to show up
As the company’s valuation rises, option exercise prices can get uncomfortably high for new hires. Late-stage companies sometimes shift toward RSUs because they can feel more “real” to employees (no exercise cost), especially when the company is closer to liquidity.
But RSUs often implicate Section 409A and need careful structuring to avoid accidental tax problems.
Example (why RSUs appear late):
A VP joins when common stock is already valuable. Options require paying a large exercise price to get shares (plus potential taxes). RSUs may deliver value without requiring the employee to come out of pocket to exercise—at the cost of more complex tax planning and documentation.
Securities compliance: Rule 701, Reg D, and “restricted” confusion
Equity compensation lives in a world where employment law and securities law overlap.
In general, when issuing equity, you either register the issuance with the SEC or rely on an exemption. For compensatory equity, many startups rely on Rule 701 (subject to limits and requirements). Other exemptions (like Section 4(a)(2) and Regulation D) may apply in certain contexts, but the details matter.
Don’t forget state “blue sky” laws. They may require filings and fees even if a federal exemption applies.
Restricted stock vs restricted securities (these are different)
- Restricted stock = stock subject to vesting/repurchase rights (an employment/equity incentive concept).
- Restricted securities = securities that can’t be freely resold publicly without registration or another resale exemption (a securities law concept).
Many startup equity awards are “restricted securities” even if they are not “restricted stock.” The labels sound similar. They are not the same thing.
Practical checklists you can actually use
Formation checklist (founders)
- ☐ Founder equity issued early (with clear cap table documentation)
- ☐ Founder vesting documented (if multiple founders, usually yes)
- ☐ Acceleration terms decided intentionally (often double-trigger)
- ☐ Founder IP assigned to company (TAA + PIIA as appropriate)
- ☐ Founder employment relationship documented (at least offer letter + PIIA)
- ☐ Basic wage/hour strategy decided (don’t wing it)
Pre-financing hiring checklist (first employees/contractors)
- ☐ Offer letter signed before start date
- ☐ PIIA signed before access to confidential info
- ☐ Clear stance on moonlighting and remote-work locations
- ☐ Equity promised only “subject to board approval”
- ☐ If restricted stock: 83(b) education + process for proof of filing
- ☐ Non-solicit / non-compete reviewed for the employee’s state
Post-financing equity checklist
- ☐ Option pool created/refreshed
- ☐ Equity incentive plan adopted (and shareholder approval if needed)
- ☐ 409A valuation obtained and board-approved
- ☐ Grants approved by board/committee with proper documentation
- ☐ Offer letters updated to match option reality (exercise price set later)
Final note
This is one of those areas where being “a little formal” early makes you dramatically faster later. Clean paperwork improves recruiting, reduces founder conflict, and makes diligence feel routine instead of terrifying.
Standard disclaimer: This post is educational and general in nature. Employment, tax, and securities rules vary by jurisdiction and change over time—talk with qualified counsel and tax advisors about your specific situation.
