
The Silicon Valley Podcast Ep154 Negotiate like a CEO with Jotham Stein
Oct 12, 2022
Jotham Stein, an employment and corporate lawyer and author, shares sharp negotiating tactics for executives and founders. He discusses offer letter length, negotiable terms like severance and equity, commission payout timing, leverage in negotiations, single vs double-trigger protections, risky contract clauses, and when to bring in a lawyer. Practical, deal-focused guidance throughout.
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Get Commission And Bonus Terms Clearly Defined
- If you earn commissions or bonuses, get the plan terms in writing and confirm timing of payment.
- Stein explains state law differences can mean you must be employed on the payout date to get earned commissions.
Short Offer Letters Can Be More Protective Than Long Contracts
- Offer length doesn't matter; specific protective language does.
- A two-page offer with the right clauses (e.g., full acceleration, long exercise window) can beat a 50-page agreement full of restrictive definitions.
Most Contract Terms Are Negotiable Except Public Policy Limits
- Almost everything in an employment deal is negotiable except terms void as against public policy.
- Examples: non-competes are unenforceable in California; indemnity waivers may be void depending on jurisdiction.




