Equity Compensation & Smart Tax Planning episode artwork

EPISODE · Apr 7, 2026 · 44 MIN

Equity Compensation & Smart Tax Planning

from How Do You Know? · host Bela Carrasco

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, NSOsEasy tips tech employees can use to reduce their tax billWhen to exercise stock options?Which share tranches should I prioritizeHow real estate affects tax planningSuggested withholdings or estimated tax paymentsThe best balance in terms of salary and stock compensationAlternative Minimum tax and how to avoid itDISCLAIMER: This podcast is for informational and educational purposes only and does not constitute financial advice. Please consult with a qualified financial professional for advice specific to your situation. The views and opinions expressed are those of the hosts and guests, and do not necessarily reflect those of the podcast, producers or sponsors, we make no representations or warranties regarding the accuracy or completeness of the content.

Episode metadata supplied by the publisher feed · Published Apr 7, 2026

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Equity Compensation & Smart Tax Planning

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