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Imagine a world where Gawker still existed, and you, a recent college graduate with a subversive streak and a surprising interest in mergers and acquisitions, decided to apply for an investment banking internship. Forget the starched collars and generic “passion for finance” declarations. This is your Gawker investment banker cover letter.
The opening line wouldn’t be “To Whom It May Concern.” More likely: “Gentlemen (and I use that term loosely, given the industry’s penchant for archaic social structures), let’s be honest. You’re probably drowning in applications from future Masters of the Universe who all sound suspiciously alike.” Right away, you’ve acknowledged the elephant in the room: investment banking’s reputation for conformity and its…let’s say *interesting* workplace culture.
Next, you’d need to acknowledge Gawker’s spirit. Something like, “I understand that, were Gawker still operating, I’d probably be writing anonymously about your expense account excesses and questionable ethical choices. But times change, and even I have to pay rent.” This demonstrates self-awareness, a willingness to poke fun at yourself (and the industry), and a hint of the cynicism that’s surprisingly useful in finance. It’s a tightrope walk – you don’t want to sound *completely* unemployable.
The key is to then transition, smoothly (or perhaps jarringly), to highlighting actual skills. “While my resume will detail my proficiency in financial modeling and my surprisingly adept grasp of discounted cash flow analysis, it won’t tell you that I can synthesize complex information, identify bullshit a mile away (crucial in due diligence, I assume), and craft a narrative that resonates, even if the underlying data is…less than compelling.” This subtly translates Gawker-esque skills—investigative journalism, sharp writing, and a knack for spotting inconsistencies—into valuable assets for an investment banker.
Forget the boilerplate about teamwork and dedication. Instead, try something like: “I thrive in high-pressure environments, especially when fueled by copious amounts of caffeine and the knowledge that millions (or billions) of dollars are at stake. I’m also surprisingly good at maintaining composure while simultaneously navigating office politics and explaining complex financial instruments to people who still think ‘blockchain’ is a disease.” Again, it’s edgy, but it shows you’re not naive about the realities of the job.
Finally, the closing. No “Eager to hear from you.” Instead: “I’m not expecting you to hire me because I’m a bleeding heart idealist. I’m expecting you to hire me because I’m smart, adaptable, and I can write a damn good memo. If you’re looking for someone to challenge the status quo (respectfully, of course, until I get my bonus), let’s talk.” Or, perhaps a simpler: “Consider this my application. Don’t screw it up.”
Such a letter would be a gamble. It might be immediately tossed into the rejection pile. But it would also stand out. It would show personality, a willingness to take risks, and a level of self-awareness that’s often lacking in the polished, pre-packaged candidates. And in a world that increasingly values authenticity, it just might be crazy enough to work.
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