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> unless he grows the value of his company he’s screwed

What are the consequences, exactly?

I suspect they gave him a timeline to IPO and/or sell or he's kicked out as CEO. His recent actions are those of a man with a deadline and nothing to lose.

Assuming that is the case: WordPress the company only needs to stay stable and valuable until everything goes through; if it burns down after that he's still met his obligations (to an extent).

That is narrowly correct and widely incorrect

zen question: what is the "everything" that will "go through"?

That's the core problem: there's no exit in sight. None

If you invest in a company and it’s valued at $1,000,000. And you want to make some money. You sell your investment in the company.

If after 5 years revenue doesn’t grow the value is still $1,000,000. Unless the value increases the investors won’t get a return on their investment. Often investment comes with conditions.

So no it’s not as simple as “just needs to stay stable”

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