If Twitter is making money, why dilute the shares with investment like this?
I'm sure one response is 'so they can grow the company', but that seems like a bit of a hard sell at this point.
How big does a company like Twitter really need to grow in order to be successful enough that they don't need to take $300 million investment deals? I mean, they are already the #1 provider of 140 character communication.
What is next?
In other words, the Saudi Prince may have bought the stake from an existing Twitter investor.
Taking this kind of money keeps them in business long enough to build real revenues (or fail).
That said, as other people have commented, maybe Twitter didn't have a choice in this matter. If so, that would have been an interesting phone call to listen in on.
Assume you have $300 million worth of Twitter stock that you can sell. Imagine getting a phone call along the lines of: "The Saudi prince is calling, and he'd like to buy all your stock for $300 million." I'd be sh*tting bricks and trying to figure out if there are any new Gunboat 90's  available to purchase. ;-)
There's not much that Twitter has done in improving their product (been 5 years)..which is something I don't really understand too much.
Is it? Doesn't seem very likely at all that it is.
On the other side you've got the people who think the Firehose is the greatest thing since sliced bread and is pretty much a golden ticket.
I don't think I get Twitter - I've never found the service to be at all useful, and I find the 140-char limit quaint and out of touch with how users want to use the service (see: URL shorteners, tweet expanders, Twitter-speak shorthand, etc). However, I am willing to accept that there's a social network I totally don't get that nevertheless rakes in some serious money (like WoW!)
But what exactly is the value of Twitter's data? Unlike Facebook, Twitter doesn't even remotely approach having a representative sample of the population. My parents are on Facebook, my uncles and aunts are on Facebook, along with everyone from my generation - Facebook has meaningful demographic data. What data does Twitter have that isn't almost exclusively limited to "young, urban, tech-savvy"?
As a marketer or data miner, what is so good about Twitter's data that would compel me to pay The Big Bucks(tm) for such a feed? Maybe I'm missing something, but it seems like Twitter's biggest proponents believe that the company can justify a multi-billion dollar valuation by providing glimpses into the thoughts of a tiny sliver of the population at large.
I have no idea what value the Twitter data feed has, but the value proposition of the service is compelling: reach interested people with minimal effort, build follower relationships to retain them.
My butcher, for instance, periodically twerps when he's got some oddball piece of beef to offload.
I used Twitter to enroll multiple cryptography classes. I had plans to use Facebook and email as well, but the response I got from a couple twerps filled my classes.
ChiSec, our local meetup for infosec people in Chicago, is scheduled and promoted entirely through Twitter. I use Crowdbooster's scheduled-twerp feature to post consistent reminders. It's miraculously effective.
This "people only use it to track celebrities" thing is a load of crap. Just as many celebs brag about their Facebook likes, but nobody says people go to Facebook for the celebs. The fact is that Twitter has a different, lower-drag interaction model than Facebook (which requires me to decide whether someone I want to talk to gets to see my kid's pictures). It's better optimized to broadcasting than Facebook is.
Wonder how much of an influence this will have on Twitter's self-censorship.
3.75% doesn't sound so bad, even if you assume bad intent. 300M had me thinking it had to be a really significant minority share, like 40%... not keeping up with the times, I guess.
In any reasonable scenario, he is purchasing shares of stock in a company on the hopes their value will rise. Doesn't matter who he is purchasing them from, it's still an investment.
Again, Twitter is a smart investment - in more ways than just money.
You should check out the library.
Then you'll start to get a glimpse of how potent twitter can be.