Has anyone been in a situation like this before? If so, what did you decide to do?
More details: Due to my own startup naivete, I agreed to a two year vesting cliff instead of a one year vesting cliff, so there’s not a natural exit point any time soon. In addition, if I were to leave the company after the cliff, but before product-market fit (PMF), it would surely not be very valuable.
The team and idea seem pretty strong, so my guess is this startup has a higher chance of succeeding than the average startup. That being said, I also guess there won’t be a liquidity event for 5-10 years. We are currently pre-PMF and have some seed funding.
Some details changed or left out to preserve anonymity.
As a generalization, profitable liquidity events are uncommon. Even VCs, after all their due diligence and experience only succeed 1:10 or 1:20.
Life is precious. Living it is our number 1 priority. So leaving is most likely the healthiest decision you can make.
Is the misery based on expected outcome or day to day activity? E.g. is it the constant firefighting or other chaos or wearing too many hats that's the problem or the like? Or is it more the case where you have an extreme lack of motivation because you have no idea where it's going or if it will amount to anything significant in impact or monetary value?
I think if I were in that situation and I was young, and was making enough to live modestly without financial stress, and I liked the people I worked with, then I'd try to see if I could stick it out for the two years. If going that route, you have to stop doubting the end value and instead merely try to reach PMF and increase value every step of the way. You can set a deadline/milestone at which point you can re-assess expected value, but don't do this every day.
Many who have struggled and stressed at early startups, look back on those times fondly, even if there was no successful exit, there are things that got built in a short time you can be proud of. Also don't forget that you're probably learning a whole lot in so many areas which is experience you can't easily get in a cushy role. That can also pay later in your career.
But like others say if you can't change your mindset and dread each day, leave.
You answered your own question. Time to bump. You are harming not just yourself but also your coworkers if you feel this way, because it's hard to do your best under those circumstances. You might also be subject to a cardiac event or mental breakdown.
Also what /u/GianFabien says:
Remember fail quick, fail often? This is a fail quick situation. See it as an opportunity to find something new that you really enjoy.
Seems pretty clear cut.
Stock options.. Is this the same sort of thing?
A friend of mine keeps telling me his options will be worth millions, and I should join them. I'll be retired in 5 years, etc.
Or is it this ratio I see mentioned where its really 20:1 odds on such a thing?
I find it all a bit confusing, and frankly I'm good at computers and not business.
1. Am I getting paid appropriately, or maybe in the case of a startup, am I likely to see any big payback
2. Am I learning, in terms of tech or other skills I'm using
3. Do I enjoy the interacting the people I work with
I haven't been that bothered on the market/business I've worked on generally