New ask Hacker News story: Ask HN: Leave and exercise shares (and get poor), or stay put (and get bored)?

Ask HN: Leave and exercise shares (and get poor), or stay put (and get bored)?
2 by marloc | 3 comments on Hacker News.
Hi, I'm currently the Head of Product at a startup in the Series A stage. Like many others, we feel the recession, but we're not complaining. We have a few years of runway. We're mainly experiencing a significant slowdown in our growth. Our ARR hasn't changed much this year. This essentially means that our Series B funding round is pushed back to 2025 (if it happens at all) I'm in a pretty good position, enjoy a good working environment, and have earned the trust of my founders. However, I'm increasingly feeling bored and eager to take on new challenges. After four years here, it feels like I've explored all aspects of my role. Yet, I find myself feeling somewhat trapped by my company shares. They are currently worth $200,000, and exercising them would cost me $25,000. While I do have the funds, it's a substantial chunk of my savings, about 30%. On the flip side, I'm confident in the company's potential and believe these shares could increase in value. The company isn't overvalued at the moment. In case of an exit, there's a good chance for a significant profit, which is crucial considering I live in a high-cost real estate area where a decent salary alone doesn't cut it for home ownership. These shares might be one of my few, possibly only, shots at building substantial wealth. Of course, I know I could also lose everything. I'm reaching out for advice because I'm at a crossroads. This situation is new to me, and I'm not even sure what information I should be considering to help make this decision. My initial plan was to wait until the Series B round, as it seemed to significantly lower the risk of loss. But with the Series B now pushed back by two years, I don't know. I'm not sure I can wait that long, yet I'm also not ready to make a snap decision about acquiring these shares. Should I wait? Should I go ahead and acquire all the shares? Should I leave and acquire none? Or should I leave and only acquire a portion of the shares? I know there's no definitive answer, but I would appreciate some insights to help lean towards a decision. I feel unable to make this decision alone right now. Has anyone been in a similar situation? Thanks a lot for your insights.