Should you still include one in your application, or only if it is required? In the case you do include it, how much effort should you spend on tailoring it to that firm?

 
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If a cover letter is required, I'd recommend completely reworking this. It's too long and too over-the top.

Make it shorter: This could be at least 30% shorter. You definitely don't need 2 paragraphs on how sports betting got you into finance. And while that may be what got you interested, your analogy to value investing is a stretch, and it makes it hard to take seriously in this context

Tone it down: You're right that persistence is a good trait to emphasize, but there's a difference between demonstrating that quality and explicitly highlighting your "failures". It seems like you're trying to convey that you work hard and you're humble (ie: have a good attitude), but the wording is awkward and meek. Don't say that only ~1% of firms you applied to offered you an interview. Don't say "I am thankful for the firm that hired me because, they gave me an opportunity and that is all I could ask for".

Keep it simple: All you have to do is convey why you're interested in Goldman/IB, provide some background on yourself (abbreviated version of your story), and hopefully relay that you're a hardworking guy that they'd want on their team. As mentioned previously, it's doubtful that anyone's actually going to read it, but if they do, your current version isn't going to be helpful

 

If you're going to write one anyways, it doesn't take a lot of work to customize it a bit for each incremental firm you're applying to. Assuming you have a decent letter, it can be a nice (but not necessary) touch.

If you're planning to apply to a lot of places though, all that time obviously adds up. Just up to you on how much time you have. Totally fine to not include

 

In a respectful tone: Is English your native language? If you need help with some of the grammatically awkward tendencies above I'd be happy to help you. (ending sentences with prepositions, verb/subject disagreement, etc)

 

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