Ok, he just invested money into company's because they are like other companies, that don't make money, in a recession. That seems like a really stupid thing to do but if the odds are 1 in 5 that it sells for as much as YouTube it might be a good bet.
Indeed. I thought calling twitter 'a new type of media property' may be hyping it up a bit too much. A more appropriate description would be 'a really popular web app'. This investor may be getting ahead of himself. +$35 million will buy the twitter team time to devise a business model, but how successful that business model will be remains yet to be seen.