Trust Fund Hobos

I was yapping over cocktails with my friend, Carl, this past summer. Somehow the conversation turned to my nephews’ fascination with hobos. I’m not talking about the problem of the homeless, I am talking about 1930s depression-era hobo attire complete with the handkerchief and and stick knapsack. My nephews (ages 12 and 14) consider themselves to be hipsters.

So Carl and I started imagining a line of expensive hobo-themed clothing. Several more dark-and-stormys later things got crazy. Hipsters love chasing the next big thing. We guessed that we’d get a ton of applications if we were to put up a fictional web site for an exclusive day school in Chicago for elite children called “Trust Fund Hobos Academy”. Thanks to the good folks at Hover.com we were able to get the domain name. Carl and I spent considerable time thinking up the catch-phrase, color-scheme, online application questions and a fictional board of directors peopled with the cream of the crop (all complete with fake LinkedIn profiles). We fashioned our fictional academy as the place for Chicago’s elite children to get the best in academics combined with the real-world grounding of the hobo life. After one last dark-and-stormy, we lost interest pursuing the project any further, but since we had the domain name — here it is. I really wonder how many people would have applied.