God, yes. Things get
much easier.
A certain class of startup-building problems gets way easier as you grow and can afford to hire specialized resources.
Get to the point where you can hire a good finance person? Things just got way easier.
Get to the point where you can hire a dedicated HR person? Things just got way easier.
Get to the point where you can hire a dedicated office manager? Things just got way easier.
Get to the point where you can hire a personal assistant? Thing just got way easier.
Beyond that, your life gets way easier psychologically as you start to achieve some success.
Your family and friends stop wondering when you're going to get a real job? Your life is way easier.
Got a big and diverse enough array of clients that losing a big one won't sink the company? Your life is way easier.
Doing well enough financially that you've been able to build up a sizeable nest egg? Your life is way easier.
As for luck, Bo Peabody's 'Lucky or Smart?' is the classic here - it's a great little book. Companies do get lucky break, but they have to be able to recognize and take advantage of luck when it comes.