In this episode of EWA's FIN-LYT Podcast, Jamison Smith and Tyler Houston break down what financial planning actually looks like for OpenAI employees navigating one of the most complex wealth creation moments in modern history.

If you work at OpenAI, you are likely sitting on significant equity through the company's PPU structure, a profit interest that triggers capital gains taxes only at the point of sale. The window to make smart decisions is short, and emotional pressure can lead to costly mistakes. Jamison and Tyler walk through how to approach tender windows strategically, why having a "number" in mind before that window opens is essential, and how to structure your holdings into two clear buckets: financial security and upside participation.

They also cover tax mitigation strategies like direct indexing, long/short approaches, and donor advised funds, along with estate planning tools that can help protect appreciation from federal estate tax. IPO lockup periods, 10b5-1 plan frameworks, insider trading risk, and how to choose a financial advisor who actually understands the startup world round out the conversation.

If a tender window is approaching or an IPO is on the horizon, this episode gives you a clear framework to protect what you have built while staying in the game for what comes next.

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