In the 1908 Sesqui-Centennial and Historical Souvenir of the Greater Pittsburgh, there are several ads that include a portrait of the owner. Here is one of J.W. Ruhlandt, whose cafe and bar was located on the South Side of Pittsburgh.
|From Sesqui-Centennial and Historical Souvenir of the Greater Pittsburgh, 1908|
An even better find is in the 1902 Souvenir History, McKeesport Police Department, which can be viewed on Ancestry.com. On one page is a photo of Braddock businessman Jacob Klaus and on another is a nice biography. Love it!
Neither of these gentlemen are in my family tree, but I hope this post inspires you to look for advertisements in similar publications where your ancestors lived. A search of "souvenir" on the HathiTrust Digital Library website is a good place to start.