Around 2008, tried to M&A regional email providers that served commercial and government enterprises throughout UK and Europe onto a more secure, standardized, and centralized infrastructure with lower employee count.
Totally obliterated by GMail and Hotmail because competing with (almost) free on something people really don't want to change once established is really, really hard even if you're gobbling up the supply-side.
Maybe it scales where there are compliance aspects like ProofPoint, but otherwise people don't want to change utility infrastructure without a big win or significant existing pain.
Times have changed but getting people to move on low cost commodity utilities with lots of options is almost like going into the restaurant industry.