What happens when a startup employee helps build something valuable—but can’t afford to keep the equity they earned?

In this episode of the Investment Wars podcast sponsored by Obsidian CIO, Joe Halpern sits down with Dave Thornton, Co-Founder and CEO of Vested, to explore one of the most overlooked problems in private markets: the liquidity gap facing startup employees with expiring stock options.

Dave explains how many rank-and-file startup employees receive equity as a core part of their compensation, only to discover—often after leaving a company—that they have just 90 days to exercise their options or lose them. The result?

Billions of dollars in potential employee wealth can disappear simply because the system was not built to finance smaller, fragmented stock-option exercises.

Dave shares how Vested pivoted from an equity education platform into a capital provider designed to solve this problem at scale. The conversation also widens into a broader discussion of venture capital, AI-driven capital concentration, vintage-year risk, private-market access, secondary liquidity, and why investors should be cautious about narratives that suggest venture capital is simply about “picking winners.”

As always on Investment Wars, the episode challenges the easy story. Private markets are not just about access. They are about structure, liquidity, incentives, risk, and process. 

We ask and answer:

- Why do startup employees often lose the value of the equity they helped create?
- Why does the market serve large private-company shareholders better than rank-and-file employees?
- How did Vested pivot from equity education to stock-option exercise financing?
- How does Vested evaluate private companies without traditional deep-dive underwriting? - What should investors understand about venture capital vintages and AI concentration?
- Is venture capital really about picking winners?
- What private-market trends are exciting—or concerning—right now?

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If you are a financial advisor interested in partnering with Obsidian CIO or would like to suggest a future guest, reach out at [email protected].

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IMPORTANT DISCLOSURE: Obsidian CIO sponsors the podcast to further education and critical thinking about the factors that affect markets and investing. The podcast does not provide investment advice. Investment advice is offered only to clients of Obsidian CIO who have entered into an advisory agreement and with whom Obsidian CIO has identified individual objectives, risk tolerance, and other investment needs.