They've got over 300 000 subscribers each paying circa 2000 USD every month. That's 600 million dollars of revenue per month. They're running a labyrinthine functionality on a 1970s System/360-style interface (command line at top of screen). He hires an absolute army of "reps" who's sole job is to try to help subscribers to find functionality, through an interface that is best described as "arcane" and where there is no semblance whatsoever of a user-discoverable taxonomy of functionality. It's all just sort of "you gotta know where you want to go". Most people use 5% of the terminal's functionality (mainly messaging) but Bloomberg refuses to tier pricing. It's all or nothing. And with finance changing rapidly, the clients are axed to cut costs. Not to mention real suspicions of monopoly because bberg is increasingly competing with its own clients in order to maintain share.
This tyrannosaurus will be hard to take down frontally, but the beast is big enough and unwieldy enough that small nibbles here and there in specialized areas can be very attractive businesses.
Other tidbits:
* Bloomberg is stubbornly Windows only. No web, no Linux, no OSX no anything else except a bit of crippleware on mobile.
* Multiple Fortune 500 companies and banks would salivate at taking him on, which means a ready pool of very cash-rich potential buyers for your growing business if you get any traction, and that includes Bloomberg itself.
* Michael Bloomberg the man has not endeared himself to the current president so may be vulnerable.
Challenges:
* quant-style people who know what they're doing are very expensive. 200k USD plus per year.
* network-effects powerful in favour of bloomberg.
* once you're through the crusty user interface, assuming you found what you want (often with the help of a bloomberg "rep"), the actual functionality is often amazingly good.