just to a add a raw account of my experience for what it's worth: I joined a startup as employee #1 and though I opted to have slightly more salary than shares

just to a add a raw account of my experience for what it's worth: I joined a startup as employee #1 and though I opted to have slightly more salary than shares I ended up with 3.2% of the shares. I was with the startup long enough to fully vest and left with actual shares rather than share options (a product of me joining when the startup was just founded and had no share option scheme). After I left at I believe the 3rd or 4th VC funding round an offer was made to buy my shares by a VC who wanted more ordinary stock to convert into a new series B non-dilution higher priority share class. All of the VC shares were of course non-dilutable. I accepted the offer (I didn't have faith the company would IPO and felt the most likely exit - an acquihire - would come when I was far more diluted at far lower value) and after a very poorly communicated and drawn out process ("we'll pay you next week" for 4 months) I finally received payment valuing the company at around $35M at a diluted share holding of 1.3% netting roughly $500k gross. Throughout I was assured that I would only have to pay a capital gains tax (I'm in the UK) and additionally received faulty independent advice that confirmed that this was the case, however 1 day before payment I was told that I'd have to pay roughly half at income tax and the other half via capital gains (the latter tops out at 20% in the UK so this was a huge difference and cost me $55k+). This was done by the startup withholding the income tax and paying it directly on my behalf via the UK's Pay As You Earn (PAYE) scheme while leaving me to pay the capital gains later. In the end I had to pay roughly 1/3 of the payout in tax netting me ~$350k. I was paid out 7 years after I joined the company. Overall I feel the dilution _was_ offset by the increase in value of the company, and the % I received was fair as to my contributions, but the tax arrangements were handled very poorly indeed and gave no room for a more efficient arrangement. Given that I felt the shares were no more than lottery ticket toilet paper + suspected I'd get cheated in some way even if there was a payout the outcome was really really good and unexpected, and have in fact changed my life (I can now buy a house after years of misspending!) But I definitely don't think the economics work out too well. I was paid probably half of the proper wage throughout and put up with a lot before vesting, having stayed there for 5 yrs that works out to $100k extra a year on top of the smaller salary (started at $50k roughly) - a FAANG or such would probably have paid the same by the end. However at the time I joined I worked in a very unmarketable (and soul destroying) role and the position helped me change my career direction, gave me a lot of good experience and ended up paying out anyway. I'd not work at a startup again (not only for salary vs. equity concerns) but I don't regret having worked at one. Something of a stream of consciousness but perhaps it provides some kind of raw data to add to the pile!