You (or your friend) might want to use Illustrator instead of Photoshop; Photoshop doesn't (AFAIK) support non-square text boxes, whereas in Illustrator you can make the text box whatever shape you want (including curves). So you can create a bunch of text boxes that are the right shape, then paste the text in and it will display in the correct shape automatically.
The only thing that I can't figure out is a simple way to get text of different sizes to display the same as in the example. This fellow's application appears (maybe) to base the font size on the amount of horizontal space available, and to do this several times with each iteration filling the gaps of the last, which is pretty smart. Using Illustrator (or Photoshop, or whatever) I think the only way would be painstaking manual effort, unfortunately.
"Do What Keepeth Thou from Wilting Shall Be the Loophole of The Law"