One Rackspace would be in the industry of technology; the other in the industry of hosting conferences. The likelihood for confusion arising from the conference having technology-related subject matter is merely a factor in determining whether the conference would violate Rackspace's trademark. It's very likely that a trademark violation would be found, but it's still possible that a violation wouldn't be found.
Note also that Rackspace only trademarked "Rackspace," so "RackSpace," "Rack Space," and "Rack-Space" are separate marks a tech conference could use those without infringing upon Rackspace's trademark.
(Companies do often allow quasi-independent organizations to run quasi-associated conferences but this is usually a deliberate decision.)
Legally, technology and conferences are entirely separate industries with very different business, legal, and tax considerations. A technology company that makes software for conferences is not in the conference industry; a conference with technology subject matter is not in any of the technology industries. This may be splitting hairs, but the law is always a matter of splitting hairs.
As this guy doesn't run a tech conference he has zero chance of defending that TM.
A guy named Joe Blogs similarly has zero chance of stopping "Joe Blogs(14)" the conference