As someone who reviews a minimum of ten pitch decks and intro/cover letters per week, I have learned to appreciate the impact of differentiation. I firmly believe that everyone has a unique, engaging, compelling personality. The problem is that people filter themselves into a mold: "I'm an investment banker," or "I work at a non profit." I'm not the very person to suggest that question "what do you do?" should be replaced by "what do you like to do?" but I may be among the first to advocate for the latter question's presence in your cover letters. Here's the problem: everyone is smart. As a graduate of NYU and a current MBA'er at Chicago Booth, it was horrifying to realize that no fewer than 95% of my classmates were smarter than me. I'm not great at math. I'm not an A+ writer. I have trouble taking tests. But where I do excel is hard work, diligence/research, and CREATIVITY.

Here's a great example of the potential differentiation in a cover letter from an article in Business Insider

Looking at the reactions, you begin to realize how dull the types of requests/correspondence these bankers receive truly must be. This is not an earth shattering e-mail. But it is different. And differentiation = memorability.

But don't take this advice and begin sending old socks in a package to stand out. Here's what this student did properly:

"I met you before..." - The e-mailer generates credibility by noting they'd met each other in person before. Although unlikely that the banker remembers the details of the conversation, he likely remembers the student being polite/considerate/etc.
"I've interned for Merrill Lynch..." - In an e-mail which is overwhelming risky (and which might suggest an eccentric person, aka a liability to a firm), the student is sure to note that he has worked in a corporate environment (probably not dissimilar from the firm he's applying to) and can maintain a level of professionalism.
"I have no qualms about fetching coffee..." - This is where the student defines himself as different from the pack. I've held college internships (I did one at Time Inc. where I effectively couriered packages/got coffee all summer) but I was unhappy because I thought I was too important for such tasks. The epidemic in the banking world (not exclusive to banking, however) is the level of pride among even junior workers. I personally remember the first time I was told to stuff envelopes for a summer job and remarking "I must be the most overqualified envelope stuffer ever." It's that kind of personality that firms want to avoid. This student credibly convinces the reader that he is so passionate about the industry that he will do anything to just get a taste.

Although this e-mail was written geared towards bankers, it is a paradigm cover letter for the startup/VC world. These are worlds defined by hustle, passion, and communication. More in future posts...

Ezra

The Importance of Differentiation