That presumption would not be correct because I have worked at multiple startups at senior to executive level positions. While the reduced comp is alluded to i

That presumption would not be correct because I have worked at multiple startups at senior to executive level positions. While the reduced comp is alluded to in the post, it is passed over and not addressed. It is absolutely _material_. Over the first five years of your career, you could easily forego over 500k, and if you keep staying at startups over the next 5, another 1-2M. With that money, you can easily mess around with side project ideas for a while, and go back to either consulting or BigCo life if things don't pan out properly. If nothing else, you've got the couple hundred thousand to a couple mill in the bank that's worth how many in the bush? If you apply a risk adjusted discount to the cashout case (which is rare), how much do you have to make on exit in order to break even with that much? It's a lot. It's enough where the numbers only make sense if you're coming in on the ground floor as a founder, or later on as an executive. New engineers can work directly with upper management in the early days of smaller companies, but as soon as real money enters the picture, you will have a layer of middle management. Often times, this will get hired externally, over the heads of those engineers that joined specifically to avoid this kind of situation. If there's VC funding in the picture, this can get political very quickly, and there are many instances where an old guard from the earlier days is pushed out and replaced by a new guard. I've seen it happen multiple times. You may dislike those 7 layers of middle management and they may be attempting to make themselves look good, but their existence also provides a formal structure for promotion and growth, and they also serve as a buffer between individual contributors who want to do their own thing in peace and the jostling nature of upper level power grabs. I lament that this appears to be the nature of the corporate beast -- nothing about startups being smaller intrinsically protects you from this. You can get screwed over if you don't play politics well enough, or even if you just get unlucky. The difference is that in a large corporation, you know what you're getting into. Nothing stops you from taking risks when you're not young. In fact, you will likely take more worthwhile risks because you can actually gauge risk properly, and you probably won't be taken advantage of by people because you're considered young, inexperienced and not knowing any better. In fact, the older the founder, the more likely it is to still be alive after one year's time. Taking risks when you're young sounds fun in concept. But, you never get back that time or youth back. You could be taking those risks with things that don't materially impact your upward progression in socioeconomic class -- such as through traveling, hobbies, studies, art or side projects. To conflate and tie the very healthy and human nature to experiment and take risks with one's adult ability to survive is a certain kind of gambling and dysfunction bound to end in regret and misery. I wish someone had warned me about it earlier, when I was that age. Perhaps it would have saved me a lot of headache.