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Learning what I was trying to teach

Editor’s note: MinnPost asked Jake Greene, a twentysomething author who grew up in the Twin Cities, to describe how he learned to sell himself to publishers, since his book, “Whoa, My Boss Is Naked,” guides GenYers on how to sell themselves. Here is the result.

Three years ago, I decided to write a career book that utilized contemporary pop-culture references to enliven advice on how to land a job and get ahead without becoming a “corporate tool.” As a member of the MTV Generation, I felt that infusing movies, television and music into my material would help me appeal to vaguely ambitious college grads with high hopes and low attention spans.

After nearly a year of researching and writing, I put together a nonfiction book proposal containing four sample chapters and a few pages of marketing and promotional ideas. I felt good about my proposal; I thought it was entertaining, different and ready to sell.

I was wrong.

The rejections began to trickle in about a week after I emailed the proposal to several literary agents I had found on Google. They arrived in several shapes and sizes — some were polite and individualized, some were short and generic, and a few were fairly offensive — but they all seemed to contain the same message: 
“Dear Mr. Greene,
… while there is certainly much merit in your proposal, I’m not convinced it is something I could sell to a publisher in today’s highly competitive market.”

Getting trumped
All of the agents seemed to agree that my material was fresh, but they had doubts about whether they could sell the book to a publisher. More specifically, they had doubts about whether they could sell ME to a publisher. In the world of business books, profiles trump prose, experts trump exciting newcomers, and (Donald) Trump trumps just about everybody.

Unfortunately, The Donald and I didn’t have very much in common. I wasn’t middle-aged, I wasn’t rich, and I had never run a Fortune 500 company. Worse, I wasn’t famous. Had I been a rock star, movie star, all-star, or even a past contestant on “Survivor” or “Big Brother,” I might have been able to skate by on the strength of my material alone. Alas, I was decidedly unfamous.

If I wanted to sell my book, I was going to have to sell myself.

Over the next six months, I tightened up my material while working to define my personal positioning (the qualities and characteristics that set me apart from the other authors on the market). I focused on the following questions: What made me different and special? What were my areas of expertise? Who was my primary audience? What unique benefits would readers get from my material?

Tackling the rambling habit
More than just answering these questions, however, I had to make sure that my answers were clear and concise. I, like millions of twentysomethings on the job market, had a bit of a rambling problem. I tended to over-answer questions and over-explain myself in conversations and on paper. After watching nearly two decades of confessional-style interviews on reality TV shows like “The Real World,” I had adopted the bad habit of broadcasting my inner monologues.

Senior executives (be it in publishing, business, or academia) have very little patience for twentysomethings who talk too much.

I also worked to identify comparisons that would make it easier for people to understand my content and my style. When selling yourself, you have to get away from the pretentious jam-band mindset that loathes comparison and evaluation. Ask jam-band members about their style or sound, and they will most likely answer with something like this:

“Ya know, it’s tough to compare us to other bands because our sound is so, like, unique. It’s, like, a unique fusion, you feel me?”

Eh, not so much.

It’s not hard to see why most jam-bands never get signed (I dissect several problems associated with the jam-band mentality in a chapter of my book called “The Reason Most Bands Suck”). Today, when people ask me about my written “voice,” I tell them that I’m like an adult Ferris Bueller – a street-smart, slightly mischievous insider who helps peers navigate the system. The comparison isn’t perfect (I don’t advocate skipping school or wearing vests, for starters), but it’s a good start.

Making the benefits ‘pop’
My earliest book proposal had a bit of a “poser problem.” I thought that I had to present my material the way all the established book experts do in order to be taken seriously in the industry. Unfortunately, as I mentioned earlier, I lacked the gray hair, green paper and tabloid exposure to compete on their level. Furthermore, I didn’t really want to compete on their level. I had no intention of writing the next 12-steps-to-success program. I view those business recipe books as “Corporate Tools for Corporate Tools.”

(By the way, whenever I see a new business recipe book at the store, I think of the scene in “There’s Something About Mary” when Ben Stiller picks up the psycho hitchhiker who tells him about a blockbuster business idea, 7-Minute Abs. “You walk into a video store, you see 8-Minute Abs sittin’ there, there’s 7-Minute Abs right beside it. Which one are you gonna pick, man?” That scene is classic.)

I love pop culture. I love talking about pop culture and, more important, learning from pop culture. I grew up learning life lessons from Bill Cosby, geography from Carmen San Diego, and science from Mr. Wizard. When I hang out with my friends, we will likely throw out no less than 20 movie references per hour of conversation. My proposal really turned a corner when I realized that I didn’t need to mute my love affair with pop culture just because I was writing a business book.

When I submitted my revised proposal to a new batch of agents, I explained that the pop-culture connection is what gave my book an edge over the other submissions on their desks. For a generation raised with remote controls in their hands, my material would be more memorable because of the nostalgia-driven movies, music, and TV references of the ’80s, ’90s and today. It became a lot easier to sell myself once I accepted that it was OK for me to focus on the subjects I enjoyed and a style that felt natural. 

Two years later

To make a long story short(er), I hooked up with an agent in the summer of 2006, and we were able to sell the book to Doubleday (Random House) a few months later.

“Whoa, My Boss is Naked: A Career Book for People Who Would Never Be Caught Dead Reading a Career Book” was published in January 2008. The book has been received well and I have spent a lot of time on the road, speaking and signing. However, truth be told, I’m still not as old, rich or famous as Donald Trump.

Thank God.

Jake Greene is a twentysomething marketing consultant and the author of “Whoa, My Boss is Naked: A Career Book for People Who Would Never Be Caught Dead Reading a Career Book” (Doubleday, January 2008). He grew up in the Twin Cities, and now lives in Nashville with his wife, Sarah, and dog, Roger.

Want to add your voice?

If you’re interested in joining the discussion by writing a Community Voices article, email Susan Albright at salbright [at] minnpost [dot] com.

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