35:18

In this episode of Fundamentals of Investing, Brian Dress, CFA (Director of Research at Left Brain) and CEO/CIO Nolan Langford discuss the hidden risks and strategic considerations for executives, tech professionals, and high‑income earners who hold concentrated positions in their employer’s stock. They walk through the various ways employees can acquire company equity—401(k) stock, employee stock purchase plans (ESPPs), restricted stock units (RSUs), and stock options—explaining the tax implications (including Net Unrealized Appreciation, ordinary‑income treatment of vesting, and capital‑gain timing), liquidity constraints, and the behavioral biases that keep people from diversifying. The conversation highlights real‑world anecdotes (Enron, the 2000 tech bubble, current AI‑driven booms) and offers practical guidance: limit concentration, use NUA when possible, evaluate ESPP discounts, decide when to sell vested RSUs, manage option exercise timing, coordinate with a CPA, and employ diversification tactics such as bucket‑based allocation, gifting appreciated stock, and avoiding double‑count exposure through index funds. The episode concludes with a call to download a free “Executive’s Guide to Managing Company Stock” and to schedule a strategy session with Left Brain.

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