Of course you're going to be diluted - that'll happen whether you're at the company or not. Obviously you'll get refresher grants if you stay, but in this case if you leave you can go somewhere else and get equity there, so you're not necessarily losing out (and in fact you're diversifying). If you think that dilution means that you have bad equity, you should never join an early stage startup in the first place. Dilution is going to happen, but it's not inherently a bad thing - your piece of the pie is getting smaller, but if it's because the company's growing very quickly, the value of your shares are going up. The percentage of equity you hold isn't what matters - the value is.
You are making some strong claims when this is very dependent on the exact scenario. My bet would be that you don't want to be replaceable because if you don't hold out to the IPO, the startup (and any new partnership they make) have every incentive to claw back as much money as possible. They could do this even if you stay but when you stay you need to be assertive enough to defend your position. I don't know how well everybody does at asserting their position from a technical role when you aren't in the room where the decision making happens. The only way I'd ever work at a startup with the goal of making a bunch of money based off of those shares is if I absolutely knew they couldn't and wouldn't fuck me over. I have no faith in any person in this world apart from very few. I would rather "grind" for the money i.e. work 8hr days and make it to my money goals quicker than 99% of the outcomes of choosing the startup path. That said, you can get good experience but the most important experience you get is knowing where you stand in any organization.
That's a fair point of view, but to your point, you're not going to work at a startup with the goal of making a bunch of money from shares, so you're probably not the target audience for this post.
I suppose you might think my comments off topic? I'd make a similar comment on a post titled "The Hardest Part of Investing in a Ponzi scheme or "The Hardest Part of buying a car to work for Uber" or "The Hardest Part of Selling for Amway". The statement itself is a deception, because the answer to the easy question for 99% is don't fucking do it.
