> I think most C level officers in a startup would be quite happy to buy lower level employees shares.
When I left my last job at a series d startup, it was small enough that the CEO had a meeting with people leaving and thanked them for their work, so the CEO knew me by name. I later emailed the CEO about connecting me with buyers. Silence.
I also talked to a few companies who lend you money to buy your shares, and one of the private markets. They at least said there wasn't interest. The company was doing ok and wasn't a sinking ship, but with zero interest from anyone, my options were effectively underwater, and I let them expire.
If you're thinking about exercising, reach out to some of those companies who either lend you money or run a marketplace. They're better at due diligence than you, and if there's no interest, you can assume the options are worthless. Even better, talk to one of these companies before signing at a startup. Tell them you're thinking about signing with X, I might want to sell some shares in a few years, but what's the interest look like now?
Why would the CEO introduce more supply to the market when that would undermine their ability to generate more runway? Every $ an investor spends on existing shares is $ less they can spend on newly crafted ones for raises...
When I left my last job at a series d startup, it was small enough that the CEO had a meeting with people leaving and thanked them for their work, so the CEO knew me by name. I later emailed the CEO about connecting me with buyers. Silence.
I also talked to a few companies who lend you money to buy your shares, and one of the private markets. They at least said there wasn't interest. The company was doing ok and wasn't a sinking ship, but with zero interest from anyone, my options were effectively underwater, and I let them expire.
If you're thinking about exercising, reach out to some of those companies who either lend you money or run a marketplace. They're better at due diligence than you, and if there's no interest, you can assume the options are worthless. Even better, talk to one of these companies before signing at a startup. Tell them you're thinking about signing with X, I might want to sell some shares in a few years, but what's the interest look like now?