Cover Letter That Got Me Flown To Hollywood, LA

This article is about connecting with your fellow human. Your cover letter is your shot at doing that and getting hired.

When you email your CV to a company to apply for a job there’s a person reading your email on the other end. A real PERSON. I feel like people forget that.

I used to be a senior business developer at a food-tech startup in London and I often got cover letters like these (these are actual cover letters I got):

With a strong analytical background, as well as vast client-facing experience, I am now looking to move into a business development or account management role. With a skill set fully aligned to managing the day-to-day relationship with clients, developing long and short-term strategies and tactics to maximise product success, in addition to co-ordinating and performing product demonstrations.

That’s nice. I don’t really care. It’s also painful to read because no one speaks like that.

Who are you as a person and how are you different to the other 50 people who wrote similar BS-generic emails?

This was for a sales role too. If you can’t spark my interest when you introduce yourself you’re not going to be able to get new clients interested in our product.

Here’s another cover letter I got:

Dear Sir/Madam,
I’d love to discuss your business, I’m currently interviewing with a number of start-ups and am interested in meeting as many as possible before the new year. I’m a multidisciplinary Sales candidate with a background of target delivery.

Oh, your a target deliverer? You’re interviewing with other startups? So is every other applicant. I’m not even going to open your attached CV because your cover letter is boring as hell.

Unless your experience is both rare and exactly what the company is looking for your CV is pretty much useless anyway. Even if your CV’s contents are the perfect fit, it might get skimmed over or simply not read if your cover letter sucks.

So talk to me. Write some words TO me. Connect with me. Use your cover letter to stand out from the crowd and tell me who you are.

Here’s the cover letter that got me flown from London to Hollywood

I applied for a business development role at Jumpcut Studios, the guys behind the YouTube channel Simple Pickup. They’re developing a new platform to help YouTube creators monetise their audiences.

My cover letter below cut through the pile of applications they received.

I ended up being the only applicant (out of 100s) that they actually considered, so they flew me cross-Atlantic to their office in Hollywood, LA. There were 2 Skype interviews before that happened, and I used some of the conversation hacks in this guide to build a connection with them in those interviews and convince them I was legit.

Here’s the cover letter I sent:

This idea is genius. The opportunity here is huge.

There are so many YouTubers out there who know how to get thousands, or even millions, of eyeballs on their content. They’ve built their own audiences, and YouTube takes a 45% cut out of what is already a pittance that they receive. Those eyeballs have the potential to be worth far more, but most content creators mainly know how to be content creators and engage people. They understand that side of things… the hard part, and while they might have a few business ideas too they don’t have the chops to know what will work and what won’t. They have to waste time and money experimenting to work it out.

You guys have done the hard yards by hacking together a WordPress site, creating products to sell and experimenting & optimizing everything along the way. You’ve worked out what works for you and now you’re thinking bigger to turn your knowledge into a system that works for content creators at large. That shit gets me excited.

My passion is creating. What fuels me is giving shape and form to something that previously didn’t exist, then making it better continuously. It gets me in Flow. Whether it’s a better sales process, a YouTube video, a website, a business idea or this cover letter.

NOT creating for too long drains my energy.

I love startup environments. I’m comfortable embracing shifting priorities, throwing plans out and flying by the seat of my pants. You need flexibility to constantly iterate products and processes in the hunt for market fit and customer love. I’m passionate about learning what makes customers tick and incorporating that insight into the product.

Breaking things down and identifying patterns with significant meaning come naturally to me. I’ve always been an analytical problem solver (hence the Civil Engineering background). At my previous startup,, I uncovered that 60% of our registered users had never placed an order. There was no dashboard to track these metrics so I did it manually on my own initiative, even though it wasn’t part of my job, because no one else had bothered to do it. Turned out there were 3 pretty obvious (in hindsight) reasons for our high attrition rate, which I also uncovered through user interviews.

I value clear communication very highly. I believe that if you applied the 80/20 rule to the list of things that make a business successful, and then applied the 80/20 rule to THAT 20%, you’d be left with “clear communication” as the 4% that’s responsible for 64% of the results. If you can get your head around that ;) Part of that means having a culture of openness where everyone is comfortable giving and receiving critical feedback & learning from mistakes. I know how to foster that sort of culture. The interns I managed at my last startup will back that claim.

I would very much love to help you guys explore and hopefully find the answer to the “Big Hairy problems of monetization, community-building, and discovery”.

Looking forward to hearing from you.


In the end the job wasn’t a good fit for either side. They didn’t end up hiring anyone. But hey, I got to meet some cool people and hang out in LA for a few days.

Make Real Friends: 3 Conversation Hacks You Never Knew

Are you putting “who you are” in your cover letters?

A friend of mine took this cover letter approach a step further when she applied for a Corporate Law role at Deloitte (… a pretty serious job at a massive company). Her cover letter brought up the deeply personal story of how she left Japan when she was 12 to follow Johnny Cash on tour around the United States.

She didn’t hold back, without going overboard, and spattered her charming personality throughout. Have a read:

Subject: Gradiator in suits

(note that she’s making fun of her Japanese background and their difficulty in pronouncing the letter ‘L’)

Dear Sir,

My name is Jo XYZ. I am an English and Japanese bilingual who has been working as a corporate lawyer at a consultancy in the City of London. I apologise for suddenly getting in touch, but I would very much appreciate it if you could find the time in your busy schedule to consider me for a role at your Japanese Services Group.

I left Japan when I was 12 to study abroad in America. I spent the initial two years following Johnny Cash and travelled down south. My family stayed in Japan and the experience of figuring my way alone has made me very resilient. There were some moments where I very nearly chose the comfort of home, but curiosity is what drove me forward during the enduring days and this now forms the basis of my unshakable confidence. I have since graduated from the University of Manchester with a 2:1 in Law and completed a Master’s degree in corporate governance. I chose the discipline because I wanted what is challenging. This meant that my choice was between law and medicine, and I chose law because there were less blood involved.

As a lawyer, I have conducted many comparative analysis of national codes and tracked the development of various regulations applicable to the financial industry. I have also worked on providing board-level governance services, such as board training, evaluation, governance assessments and peer benchmarking. Furthermore, having trained in company secretariat practices, I have supplied extensive administrative support both internally and externally.

I am now in search of an opportunity where I could combine my linguistic skill and the experience of working for the financial industry. Although I value the experience gained at the current firm, I now crave working for a larger organisation with the chance to be involved with Japan. Combining my linguistic skill, legal expertise and ‘bring it on’ attitude, I believe I can be of an asset to your Japanese Services Group given the opportunity.

I would like an opportunity that is much more than simply being able to speak Japanese. Rather, I would like to discover what I can do with it, which is the reason for my reaching out to you today. I tried to keep this as brief as possible, though I cannot help but feel I have left so much out. If there is a slightest chance that you would like to find out more about me, please refer to the CV I took the liberty to attach to his email.

Thank you very much for taking the time to read this far. It is my sincere hope that I hear from you in the near future.

Rock ‘n’ roll,

Jo is about as “rock ’n’ roll” as it gets, and actually speaks this way in real life, which is why her cover letter feels authentic.

Does it surprise you that she built a close relationship with the Senior VP who opened that cover letter? He ended up bringing 6 department heads together to create a new role just for her.

The important thing to consider here is this:

Are you putting who you are into your cover letter? Are you writing your cover letter to a real person?

If you aren’t, why not give it a try? Because there’s a real person on the other end reading it, and they’re giving your job to the people they connect with.

Pete - Social Coach For Intelligent Men

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This was great, thanks for the tips. Any resources for becoming a better writer?


Someone looking for work emailed me recently. They CC’d other companies in on the same email… **facepalm**.