2 years ago, I joined a startup as a Data Scientist as employee ~10. My base salary was in the mid-100s and I negotiated ~0.25% equity stake of a company valued at ~$10M at the seed stage. (Should have negotiated much more, but hindsight is 20/20.)
Fast forward to today – the company is valued at $500M+ post-Series B, and my equity stake has been diluted to ~0.06%. Turns out that multiple convertible notes hit when the company raised a Series A and I was severely diluted. Employees who joined ~1 year after I did at the same level received 2-4x as many options, albeit with a much higher strike price.
I believe that this company will 10-20x and IPO within the next 4 years. But I also know that is far from a certainty.
1. Does it make sense to try to re-negotiate my equity comp, or should I just get a new job?
2. How should I go about having this conversation with the founders?
If you were given the option to buy in at the same price (anti-dilution clause, not sure if you had one) and you let that go that is your problem, not theirs and definitely not the later investors, everybody diluted in those rounds including you.
Assuming your stock has already vested you could try to make a play for the part that has not vested yet where your BATNA is to walk and find another employer, this time forewarned about some of the aspects of equity plays. $300K (the value of your equity at this point in time, assuming it has vested) adds effectively $150K to your pay for the last 2 years with the big question of whether there will ever be a market and whether or not that valuation estimate is accurate or not. The IPO may never happen (tricky market) and so you may end up holding that stock but in a way that may make trading it very hard. And then there are still the various tax angles to take into consideration.
Best of luck!