"Staples will print a custom campaign sign for $10, and I wanted one that made me laugh, and also express myself at the same time," said Ross of his texting short-hand for "I Do No Know Not Trump Though." Two hours after posting a photo of his sign on Twitter, it had been retweeted 4,000 times and people were already selling bootleg merchandise using his idea.
Ross sold hundreds of T-shirts with his slogan ""IDK NOT TRUMP THO" on idknottrumptho.com, before getting an email from Urban Outfitters asking him to make a deal.
"The licensing company told me that this is one of the most successful designs they've worked on with Urban Outfitters," Ross said. "They did a preliminary run of 300 T-shirts, which sold out in less than one day, and the next order was for thousands."
And, unlike past forays in which the youth-minded retailer wound up apologizing and pulling merchandise (think red-stained "Vintage" Kent State Sweatshirt or its Peachy Head "Shampoo For Suicidal Hair,") Urban Outfitters is unlikely to draw heat for its latest politically inspired merchandise.
So say branding experts, who argue that T-shirts and coffee mugs bashing the presumed Republican presidential nominee merely reflect the contentiousness of the current political climate.
"It is rare for major retailers to be political, let alone in such a divisive manner. Most simply showcase their levels of patriotism at relevant times during the year," Jennifer Braner, a spokeswoman at ShopperTrak Chicago USA, emailed. "Urban Outfitter's decision to offer the Trump T-shirt is, however, in line with the offbeat nature that their products have been known for in recent years and it capitalizes on the contentious nature of the 2016 election."
Melissa Arnoff, a senior vice president at Levick, a communications firm specializing in crisis and issues management, said that the usual playbook no longer applies, given the unusual election season. "I think all the normal rules are off," Arnoff said. "Urban Outfitters is known for hitting on what is trendy, and it is trendy right now to really not to like Donald Trump."
"If HBO can do it, so can Urban Outfitters," added Arnoff, referring to John Oliver's televised pitch to "Make Donald Drumpf Again," with the comedian setting up shop online to sell merchandise touting the effort to have the business mogul take back what Oliver said is Trump's ancestral name.
The anti-Trump message seems to be at odds with the past-Republican leanings of Urban Outfitters CEO Richard Hayne, who reportedly has a history of backing mainstream Republican candidates, but likely appeals to millennials, a key demographic for Urban Outfitters.
"A retailer of their stature is well aware of any risks and does a significant amount of research regarding product selection," Braner said. "This move is clearly calculated and believed to resonate with Urban Outfitter's core consumers."
The slogan "resonates with an Urban Outfitters audience," Arnoff said. "Because so many people don't like Trump, this is not going to be a negative for their brand."
Urban Outfitters did not return a request for comment, nor did the Trump campaign.
Urban Outfitters also sells shirts reading "Hillary Runnin' Thangs Tour 2016" and "Feel the Bern," referencing the presumed Democratic nominee and Bernie Sanders, her onetime rival.
As for Ross, unless an independent candidate pops up that he views as viable, he is not longer in the 'do not know' camp. "If we're talking Hillary versus Trump, I am with Hillary all the way. The Republican party seems to be scared of Trump too."