Actually, I think most C level officers in a startup would be quite happy to buy lower level employees shares.
Of course this would have to be possible considering the shareholder agreement, but I don't see any reason it would not.
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...
See for instance the graph Company Age (Years) shared by Meritech. There are 8 companies in the cohort that are 20+ years, only 1 (Salesforce) that IPOed with less than 10 years. In fact, from the entire comps (20+ public SaaS), only Salesforce IPOed at year 5.
https://www.meritechcapital.com/public-comparables/enterpris...
This looks like it's a very narrow set of companies. We should be looking back farther, and wider. Recall that, for example, Netscape IPO'ed after 18 months and Amazon IPO'ed after 3 years. For better or for worse, 90's companies generally IPO'ed much quicker than the SaaS cohorts mentioned in the data you linked to. Back then, 10+ year timespans until IPO were rare.
Netscale and Amazon are only anecdotes and pure exceptions of the dot.com era. The set of companies that went burst during this period because of bad management is composed of at least 15 publicly traded companies. If your compensation included shares of any of these quick IPOs (AOL, Yahoo, pets.com, Global Crossing, etc.) your shares would have ultimately be zero as well (compounding interest is what makes you wealthy with these long-term horizon packages and you wouldn't have sold all your shares at ipo).
And whether a company goes bust post IPO isn't really the issue here since liquidity is what we're discussing.
Live and learn I guess.
If the company fails to achieve a good exit, I don’t need any more exposure. It’s almost a lose-lose.
Reducing your exposure in the company is an employee mindset, not an entrepreneur one.
One of the very first question potential clients ask us, is "how much is the management committed?", and by that they mean, how much of their own money did they have invested in the company.
Much more of a red flag if the CEO has that kind of cash sitting around from taking something off the table early.
The institutionals passing on their ROFR would smell bad, but may still happen due to their Capital constraints.
Most companies will set away 5-10% of their stock value to be owned by employees. The only reason they'd buy it back from you is to give it to others.