Not a day goes by without someone sending me an email or a message telling me how they wrote something that they would love me to read. After I say that I would be glad to, then comes the inevitable "And if you enjoy it, feel free to share it with your audience."
I have said many times that one of the primary differences between sales and marketing is subtlety. Of course, sales also needs to be subtle, but even a good salesman cannot hide that they are indeed trying to sell you something. If a marketer is good at what they do, you won't even know that you are being marketed to.
Just because you pretended to want my opinion on your startup before asking me to promote it for you does not make you subtle or a good marketer. You are, at best, a glorified sales person.
Instead of pretending to be subtle when all you really want is to cut a corner and leverage the audience I spent years building, here is what you should do:
Make sure your content is good enough to share without you asking.
I know this is not what you want to hear because if you are asking someone to tweet about you, clearly you want a quick fix, a shortcut, but the right way to do this is to produce content that is so valuable, people will want to share it.
Think about it this way: if there is a journalist and you want to pitch that journalist, remember, if your story is solid, you are doing them a favor as much as they are doing you a favor when covering it. They need to write stories, you gave them something to write about. It's a win-win.
Same goes for people on social media. If you produce good content, I am more inclined to share it, and thereby provide value to my audience. On the other hand, asking me to share your content accomplishes the exact opposite, it makes me not want to share it, even if it is good.
Build the relationship before you need it so I am inclined to promote your work.
Now if you do produce good content that I would be theoretically inclined to share, and I never even see it, then what have we accomplished? It is therefore important that you actually invest the time building out your audience before you need them for something. Build some trust, keep people in the loop, let them feel like they are a part of the process, and then, when the content is ready for distribution, or when your startup is ready to be promoted, the people are there and ready.
If circumstances do not allow you to invest long term, at least be up front about it.
In the worst case scenario, when your CEO is breathing down your neck to get views on that article, and you absolutely need a quick win, then at least err on the side of transparency.
"Hi Hillel, I know you hate this kind of request, but I have a situation and wanted to be up front. It would help me a lot if you tweeted this article, assuming of course, you think it is valuable." That kind of message would increase your chances by tens of percents, I believe.
The bottom line is, if views are what you are after, you have two choices. Either do it right so that view count will be sustainably high or be totally transparent and ask for a favor straight up. Don't pretend to be subtle and think you are tricking anyone. That is condescending and offensive.