(all of this fits quite well with the 'jagermeister' font.)
Richard Branson was the person he most admired - so below are examples of the Virgin Megastore logo which Branson set up.
His favourite clothing brand is Ralph Lauren; Logo
Flying/freedom/space/uplifting/happiness - looking at typeface examples which surround these words
MARIO HUGO - Zune Brand Principles.
I found his body of work very intriguing and inspiring when researching different typefaces.
Other typefaces which I found;
Typefaces - bold, lower case, clean cut, organised
'Moaning' was his bad habit, so working around this work examples of text could include characteristics such as; disjointed, dispondent. Moaning is generally associated with a continuous negative mark, so 'continuous' and 'exaggerated' are other characteristic of the typeface I have explored.