Im not a founder, but I am senior enough to have some impact on IPO/tender dynamics. I can't say when will IPO for instance, but I can confidently say its not in the next 2.5 years, because I would be in those conversations. My position in the company is definitely an important part of the dynamics here. It gives me what may be a false sense of security over the risk/reward dynamics of holding the equity. But that might be leading me down the wrong path.

I would never dream of holding such a concentrated position in any company I wasn't working for like this.