Equity Compensation & Smart Tax Planning

Equity Compensation & Smart Tax Planning

From How Do You Know? by Bela Carrasco

April 7, 2026 · 44 min · Season 2 · Episode 7

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
  • tech employees
  • financial advice
  • stock options

Keywords

  • equity compensation
  • tax optimization
  • stock options
  • RSUs
  • ISOs
  • NSOs
  • Alternative Minimum Tax

Mentioned in this episode

Organizations: Harvard Business School

More episodes of How Do You Know?

Explore listener stats, chart rankings, contacts and more on the How Do You Know? podcast page.