What are the biggest challenges in getting media coverage for your startup?

The main challenge I had was to get journalists to take interest in my story.

Often times people go to the media hoping for exposure, but they don't have a great story to share. 

Most of the time the story is all about them and their startup. The media don't want that.

You need to put yourself in the shoes of a media organization - what do they want? What do their readers want?

Generally they want:

• A great story - something that people will go "wow" and be engaged in. Better yet, a sensational story that will attract more readers (and people to share).
  
• A unique story - something that hasn't been published before and they're the FIRST to write about it.
• It has to be credible - the truth matters.

Another thing to note is that journalists are very busy and usually delete/archive most emails they get, especially those that begin with "PRESS RELEASE".

Try to make the interaction PERSONAL. Build rapport, provide context, and offer a short, concise and impactful pitch.

Also, it helps to include all materials they need to produce the story effectively (media kit) in the email so they don't have to go back and forth with you. Save them time.

Sometimes I feel journalists are very busy and can also be very rude, especially when you pitch to them in a long-winded fashion.

It is also very tedious to reach out to many of them, as most of them only use email and Twitter. It might be easier to get someone to intro you to one.

Finding journalist contacts is also very time consuming. Most directories / online databases dont have updated information, and many of these journalists/media people have moved on to other companies (their emails don't work!)

Reaching out to the general email of news companies almost never gets through too.

I feel it can be a very bad thing as to "get their attention", you have to send in a very hyped up story. And when they cover it, it gets even more hyped up, maybe distorted from the truth.

I have tried many ways of reaching out to media outlets and news companies. However, none of them seems interested.

But when I learned about what media outlets want, then the doors opened up. Yes, you have to start thinking and put yourself in their shoes before starting to approach them blindly.

Further more, I think it's always having the mindset of putting yourself in someone's else shoes, you should get many things done fine.