Cool Corporate Tools for the Slacker Generation 

Local author gives advice to people who know more about reality TV than résumé-writing

In business, arrive on time—or, better yet, early. This is the corporate golden rule. But for an interview with Jake Greene, first time author of Whoa, My Boss is Naked: A Career Book for People Who Would Never Be Caught Dead Reading a Career Book, I was late to our meeting at Past Perfect. Good thing his book is geared more toward the Ferris Buellers of the world than any aspiring Donald Trumps.

Originally from Minneapolis, Greene moved to Nashville so his wife Sarah could attend medical school at Vanderbilt. A strategy and marketing consultant with his own company, Greene has a master’s degree in sociology from Stanford University and has worked for both start-ups and Fortune 500 companies. Inspiration for the book, a workplace primer for the post-college set, came when he took a job requiring long hours on the road. “I’ve spent a lot of time in Chevy Malibus and Fairfield Inns,” he says.

Scene: How do you know so much pop culture? The book’s packed.

Greene: I’m a 20-something who grew up with a remote control in my hand like everyone else. I thought it could be fun to incorporate pop culture.

Scene: You say 20-something but are you on the dark side?

Greene: Certainly. I just turned 28. I’m either the old end of Gen Y or the younger end of Gen X. But, definitively, if you turn 21 in the 21st century, then you are from a generation that was raised on the Internet and reality television. Throughout our formative years [we] learned life lessons from pop culture. It sort of started with Sesame Street, then moved to Full House, then it was the Discovery Channel, and throw in a little moral moment from Saved by the Bell. I didn’t see any reason why that couldn’t continue as we became professionals. You only have a certain window in which your pop culture knowledge is relevant. If I wanted to write it down, now was the time to do it. If I was tossing around Saved by the Bell references in 10 years, people would be looking at me kind of funny. I’d be that old creepy guy.

Scene: Can you write off your cable bill as a business expense?

Greene: It’s up for discussion. I didn’t do it last year.

Scene: You do have to have it.

Greene: Let me make it clear: It was my responsibility to watch Kid Nation this year. My wife makes fun of me all the time. She has no interest in and doesn’t want to watch A Shot at Love with Tila Tequila. I love train-wreck reality shows. Given the way reality shows are set up—the competitive nature and all of the anger boiling over and the absurd challenges—it’s sort of a caricature of the business world. Everybody is fighting to get ahead, fighting to get that promotion.

Scene: The book’s chapters are really short—“short” as in one chapter topped out at a page-and-a-half. Was it a deliberate decision to aim for chapters that are more like sound bites?

Greene: It certainly was. I think there are a fair amount of books that are 200 pages of mundane bullet-pointed lists, especially in the business genre. I didn’t want to write a lecture. My audience was my friends. These are people who often didn’t attend lectures when they were paying to be there, so why are they going to buy one? I wanted it to be a situation where if you picked up the book for five minutes you could get something out of it. I wanted it to be a distinct departure from some of the clichéd business books, sort of the corporate tools for Corporate Tools.

Scene: Tell me about your idea that cover letters are like love songs.

Greene: When I was interviewing interns, I was sent these cover letters that literally all looked the same except there’d be a different adjective or a different adverb or suck-up noun. The love song—the idea that you don’t write a cover letter to say ‘I want to get with you’; you write it to say ‘I want to get you’—was kind of an interesting idea. Then it was just a vehicle for me to recall some terrible love songs which was a lot of fun for me, of course.

Scene: How do you feel about Britney?

Greene: Oh, wow.

Scene: You’re speechless.

Greene: I think there are so many experts right now who are commenting and dissecting Britney’s situation that unfortunately I’m just not qualified to offer a professional opinion.


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