No reason you can't do both? Start at the one you want now. Transition to the other later. That's what I'm doing. This isn't an either or situation. If you want

No reason you can't do both? Start at the one you want now. Transition to the other later. That's what I'm doing. This isn't an either or situation. If you want to take the risk, now is the a best time probably while younger. However, one could argue if you save properly doing the riskier option later might be better. It will depend of course. The other factor to consider is quality of life. How many hours and what types of stress will the bigco job have versus the younger company? I joined the younger company first and I don't think a single person works 40 hours and the environment is relaxed, the CEO/founders are awesome! The pay is good, but it's not Google levels, but there is opportunity to increase that. We are quite profitable already. I can try for a bigco job another day, in fact any day or not. However, for now, because of my life situation, I chose the smaller company.