I started beauty blogging four years ago. My blog ran on nothing but my time, computer, internet connection, and a student's allowance. Starting out I wrote general information articles on beauty and reviews on products I buy. Four years later, I am earning quite a good sum of my money from my blog alone. The swag I get every month is maybe worth five figures. And I still write general information articles and reviews on products. :)
I sound like a bragging asshole just about now but I'm telling you this because my "success story" is not as simple as it sounds. For the past four years I invested a huge chunk of my time and money on this website. Waking up at 6am just to write and process photos, planning my content days beforehand, marketing my blog and personal brand, these things are not a walk in the park. I have what I have because I'm passionate about my niche. I did this when I got nothing out of it. I will still do this even if all my sponsors leave me.
My actual job is handling the social media and PR of retail brands. Every so often, a new blogger messages or emails these brands asking for "sponsorship". That is, free stuff for their blog review or contest. I know that the chance to get free things is something not many people can resist. I try to understand that they're looking for more content and followers for their blogs - certainly not an easy thing to do - so they turn to brands for help.
It is within our means to give stuff away. But as with any business transaction, what one has to offer (i.e. the blog) has to be worth our time and cost of merchandise. If the blog isn't worth our investment, then the blogger has no business asking for sponsorship.
When is a blog worth a brand's investment? As a brand consultant, I usually look for three things in a blog I want to work with. These are traffic, quality of content, and influence. Traffic is the number of page views and unique visits a blog gets every month. Ideally, 50,000 upwards for monthly page views is a good number to start with. You get 110,000+ I'll tell you to shut up and take my money.
A blog has to have high-quality content. That means sharp pictures and/or insightful, informative writing. Ideally both, but I'm not a grammar or photo Nazi so basically I'm looking for passionate content. I love blogs that have organic, original posts straight from the heart.
A blogger's influence is also a big factor. What kind of followers does the blogger have? What circles do they move in? I try to guage how convincing and credible a blogger is. I also try to see what kind of people he or she influences. Are her friends influencers in turn? I want the right people to talk about my brand.
A blog that has these three key factors is a good blog indeed. :) But having two is also more than enough. If a blog has traffic and high-quality content, I'm happy just to get a good amount of exposure for my brand (especially for search results). Traffic and influence (usually celeb blogs), I'll take it because the blogger probably has a captive audience. Content and influence, I'm happy with that too because these blogs are probably run by industry insiders (like magazine writers/editors, makeup artists, businessmen) so being exposed there may help with my brand's status.
So when can a blogger ask for sponsorship? It's simple. When you're already in a position to ask for sponsorship - when your blog has high traffic, good content, and influence - you'll never have to ask to be sponsored. Brands will come to you.
If no one is coming to you, thus prompting you to ask for freebies, then you're doing it wrong. Work on your blog instead and keep at it. Don't do it for money or freebies, do it because you wouldn't have done otherwise.