Black with Equity Webinar Snippet: Equity Compensation Basics, Taxes, and Diversification

In this episode we recap a jam-packed week ending with a snippet from our Black with Equity webinar for Black History Month.

We explain the basic forms of equity compensation, like restricted stock - a “will be yours” benefit, emphasizing grant date vs vest date, W-2 reporting, vesting schedules, and taxation as ordinary income upon vesting, including the common underwithholding issue from 22% supplemental withholding and solutions like increasing withholding or paying quarterly estimates.

We also cover non-qualified stock options as a “could be yours” benefit, defining strike price, discount element taxed on exercise, exercise windows, and double-trigger acceleration, plus negotiation tactics at hiring, reviews, and severance.

Lastly we touch on ESPPs, offering periods, lookback provisions, and taxable discounts, and warn against overconcentration in company stock and the benefits of portfolio diversification. Sign up for the full unedited release at newmoneynewproblems.com/subscribe!

00:00 Webinar Recap and Access
01:04 Ad Rejection Rant
02:39 Restricted Stock Basics
05:40 Vesting and Tax Impact
07:37 Withholding Pitfalls and Fixes
10:37 Negotiating Restricted Stock
12:24 Stock Options Overview
14:11 Option Terms and Taxation
18:42 Option Negotiation Strategies
20:17 Employee Stock Purchase Plans
23:12 Avoiding Stock Overconcentration
27:14 Leveraging Diversified Portfolios
29:51 Wrap Up and Next Steps

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