This is what prevents them from taking the initiative in the first place.
Back in the day — before women became more independent (thanks, women's rights movement! For the most part, dating was easier: A man courted a woman and both of them knew the end goal if courtship went well: marriage.
I'm just not good on my phone during the day and the liquid courage of a drink or two definitely makes it easier to send the first text to a girl I've been talking to.
Plus, I'm not ready for a big commitment and I don't want to give off the wrong message by texting a girl all day long.
So, if you do choose to initiate, do so only during the early stages of dating, that is, until he builds his confidence and comfort around you.
Once this happens, you will need to gradually assume a less assertive (more traditionally female) role, because he will then be more liable to get bored with you, wonder if he could do better, consider his other options (the perception of which his newly-found confidence will likely inflate), fool around, etc.