Robert Steffen (aka Umbrella Man) was born in 1965, and is one of Santa Cruz' Town Characters. During his heyday he would don pink women's clothing and makeup and then proceed to walk down Pacific Avenue very slowly. He did this six days a week! At the time, it was an event to spot him in normal clothes, and rumor had it he worked in IT "during the day". He has been nominated locally for "Best Street Performer" in the past. He is also known as Umbrella Guy or Pinky, and a myspace has been created about him under the name of Robert 'Pinky' Valentino.
What Robert did before he became "Umbrella Man" has been a topic of great discussion in town. He was previously recognized by his adorned garbage bag outfit, provocative signs and presidential ambitions. Some believe he was a lawyer, others swear that he worked on confidential operations with NASA, as he himself has claimed in interviews. Steffen says that he worked for the NASA Ames Research Center as an Electrical Engineer. He quit because he "saw no point in building things if people didn't appreciate them". Since then he has lived among the homeless of Santa Cruz.
In 2008 Robert was seen less frequently Downtown, and some theorized this was due to the emergence of Orange Guy (who was interviewed by Bruce Bratton on Bruce's radio program). Presently, Robert does not dress up the way he used to, and early in 2009, in an interview aired on SoWat TV he said he was painting, and in August Santa Cruz Weekly posted the links to Robert's Art Website and Robert's Twitter Page on their Facebook page.
Early in January of 2010 Robert annouced he would be running for a spot on the Santa Cruz City Council in the November election , but later in the month he announced that he was withdrawing from the race due to personal health issues.