Equity Compensation & Smart Tax Planning | Application

Equity Compensation & Smart Tax Planning | Application

From How Do You Know? by Bela Carrasco

April 21, 2026 · 5 min · Season 2 · Episode 8

About this episode

This episode discusses the complexities of equity compensation and tax planning strategies for tech employees.

Tech employees often face a double-edged sword: while many receive substantial compensation through equity, it frequently leads to over-allocation to a single company and significant tax burdens. In this episode, @Josh breaks down the complexities of equity compensation and smart tax planning strategies. Josh Radman is a fiduciary, certified financial planner, and enrolled agent (which qualifies him to prepare tax returns and to give tax advice). His focus is on helping tech and mid-career professionals navigate tax planning and equity compensation. After graduating from Harvard Business School and entering the tech industry, he had trouble finding someone who could help him with his equity questions and decided to make a career pivot and become an advisor to help those in similar situations. Now, he guides clients through tax optimization, equity strategy and broader financial planning. Define RSUs, ISOs, NSOs Easy tips tech employees can use to reduce their tax bill When to exercise stock options? Which share tranches should I prioritize How real estate affects tax planning Suggested withholdings or estimated tax payments The best balance in terms of salary and stock…

People in this episode

Host: Bela Carrasco

Guest: Josh Radman

Topics covered

  • equity compensation
  • tax planning
  • financial advice
  • tech industry
  • stock options
  • real estate

Keywords

  • RSUs
  • ISOs
  • NSOs
  • tax optimization
  • stock compensation
  • Alternative Minimum Tax
  • financial planning

Mentioned in this episode

Organizations: Harvard Business School, How Do You Know?

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