In this candid "HR Heretics" segment, Nolan and Kelli expose the hidden risks of equity compensation, including Nolan's $8 million DoorDash missed opportunity. They reveal essential questions about share counts, strike prices, and exercise windows that can make or break startup wealth. Their message: equity details are negotiable, but education is your responsibility—not the company's.

*Email us your questions or topics for Kelli & Nolan: [email protected]

For coaching and advising inquire at https://kellidragovich.com/

HR Heretics is a podcast from Turpentine.

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KEEP UP WITH NOLAN + KELLI ON LINKEDIN

Nolan: https://www.linkedin.com/in/nolan-church/

Kelli: https://www.linkedin.com/in/kellidragovich/

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TIMESTAMPS:

(00:13) Intro

(00:52) Being Smart about Equity

(01:46) Nolan's $8 Million Mistake

(03:05) Understanding Share Count

(04:44) Strike Price Explained

(06:00) Preferred Price vs. Strike Price

(07:43) Net Value Calculation

(08:42) Golden Handcuffs Reality

(10:31) Exercise Windows

(12:00) Negotiation Opportunities

(12:26) Tax Implications

(14:07) Early Exercise Benefits

(15:09) Sponsors: Planful | Metaview

(18:09) Additional Negotiation Tactics

(19:57) Executive Liquidity Options

(21:32) Double Trigger Provisions

(23:12) Vesting Schedule Negotiation

(24:00) Key Takeaways

(24:37) Personal Responsibility

(26:08) Resources & Research

(27:01) Final Thoughts

(27:23) Wrap

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com