WTF? Startup Cover Letters That Would Give Bankers a Heart Attack

Wall St

A couple weeks ago, the blogosphere exploded with an overstated story about an “unapologetically honest” cover letter and its subsequent email chain that went viral on Wall Street. The letter appeared on Business Insider, Huffington Post, Forbes, Gawker, and others.

Here’s the cover letter that went viral on Wall Street.

Wall Street execs called it “one of the best letters they have seen,” and Business Insider described it as “perfectly blunt.” Click here to read rest of the email thread offering unrelenting praise for the letter. No, seriously, read the thread.

Cover Letter email

Okay, sure. It’s an undeniably solid and cerebral cover letter for an entry-level position. But would it really qualify as “classic,” and “hilarious but bold” anywhere outside of Wall Street?

Here’s my personal opinion (and feel free to offer your feedback below): The letter only stood out because it was sent to an investment bank, where honesty and a level-headed sense of reality is apparently out of the ordinary. If you read the resulting email chain, that fact doesn’t seem to be lost on bankers, either.

I talked this over with several colleagues at smaller tech companies:

We maintain that if one of these banks’ HR directors were to receive the types of cover letters we receive as an Internet startup (a title we dutifully cling to, even if we have outgrown it) – they would likely go into cardiac arrest.


WTF? Here’s our idea of an awesome cover letter.

This is the very first communication our marketing team received from an entry-level candidate (now a full-time associate on our team).

We were immediately drawn to Tyson Ferguson‘s inquiry. It’s just as honest as the famed Investment Bank Winter Internship Cover Letter Miracle, but takes some risks and offers a full serving of personality – all without the unintentionally pretentious pretext. In general, well organized, short-but-sweet cover letters give us a good impression of a candidate’s confidence, independence, and flexibility in working with a small team.

WTF’s letter doesn’t read like the work of someone who is resigning themselves to the shackles of corporate servitude.

 WTF Email


 WTF Cover Letter

Our immediate response was positive,

But the most important response came from uShip’s one-person HR team, without hesitation:Interview him!

Shortly thereafter, we hired WTF onto our team. He’s an invaluable part of our marketing team today.

Other startups agree –

The cover letters we receive are more engaging and so far removed from the 1% that bankers’ heads would spin.

From our friends at self-storage marketplace

Sparefoot Email

Even some of the more… questionable… cover letters still stand out for their confidence and shamelessly convenient appeal to job responsibilities:

Curse Word Cover Letters

Have you received any awesome cover letters that you’d like to (and are allowed to) share? Send them our way at 

[Photo courtesy Matthew Knott, Flickr]

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WTF? Startup Cover Letters That Would Give Bankers a Heart Attack was last modified: December 3rd, 2014 by uShip
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