What Executives Actually Need to Know About Their Equity Comp episode artwork

EPISODE · Jun 26, 2026 · 24 MIN

What Executives Actually Need to Know About Their Equity Comp

from Left Brain Thinking

Brian Dress and Noland Langford walk through everything executives need to know about their equity comp packages, from the basics of RSUs, stock options, and ESPP, to vest day tax implications, the job change trap, and what building a real equity compensation plan actually looks like. In this episode: • The three types of equity comp and what makes each different • What vest day actually means (and why it matters more than a calendar reminder) • The tax withholding gap and other hidden costs • Expensive mistakes executives make around vesting • The job change trap: options expiration windows and negotiating equity you're leaving behind • Underwater options: how to think about them • What a real equity comp plan looks like, and how to start building one Chapters: 00:00 Cold Open 00:56 Introductions 01:40 The Three Types of Equity Comp 03:53 What Actually Happens on Vest Day 06:00 Expensive Mistakes Around Vesting 09:06 Hidden Costs: The Withholding Gap and Concentrated Stock 13:49 Stock Options: What Executives Need to Know 16:11 The Job Change Trap 17:30 Underwater Options 18:53 What a Real Equity Comp Plan Looks Like 22:09 Closing Thoughts Links mentioned: • Book a free 30-minute consultation: https://tinyurl.com/Book30MinutesWithLeftBrain • Free guide, Executive Guide to Managing Company Stock: Download the Executive Guide • Watch on YouTube: https://youtu.be/vWWGAbpPvDU Left Brain Wealth Management is an independent wealth management firm based in Naperville, Illinois, specializing in financial planning for corporate executives. Full Disclosure: No Client or potential client should assume that any information presented or made available on or through this video should be construed as personalized financial planning or investment advice. Personalized financial planning and investment advice can only be rendered after engagement of the firm for services, execution of the required documentation, and receipt of required disclosures. The content is developed from sources believed to be providing accurate information. The information in this material is not intended as tax or legal advice. It may not be used for the purpose of avoiding any federal tax penalties. Please consult legal or tax professionals for specific information regarding your individual situation. Additional information about Left Brain is available in its current disclosure documents, Form ADV, Form ADV Part 2A Brochure, and Client Relationship Summary (Form CRS), which are available online via the SEC's Investment Adviser Public Disclosure (IAPD) database at www.adviserinfo.sec.gov/firm/summary/170348.

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