Reading books is only going to get you so far.

Join a startup for a few years and get operational experience. While you're there don't just limit yourself to hacking. Get to know your co-workers (should be easy, it's a small organization right?), offer to help out cross-functionally, etc. Gain visibility and understanding into what the founders and managements think about long-term and on the day-to-day.

Once you've got your feet wet, then take the jump yourself.