How to Write the Best F’ing Email of Your Life

Some of the most important things I've learned through experience in cultivating what I believe is among the most underrated skills you can develop: writing great emails

About Lucky Maverick

About Jonathan Bales

You guys on LinkedIn? You know the messages you get on there? Crafting the perfect email consists of doing the literal opposite of everything you receive there.

That could be the entire post, honestly, but I’ll keep going because, as someone who has spent their entire adult life inside and avoiding human interaction at all costs, err…I mean…working online, I know a thing or two about emails.

I’ve gotten so many emails from people who’ve read my books or love FantasyLabs or want a job. And before that, I sent so many emails to people I respected. Communicating effectively via email is among the most underrated skills you can develop, especially in an era in which many unnecessary meetings are rightfully just becoming well-crafted emails. Having been on both ends of the communication, I know what works and what doesn’t.

Actually, I doubt he even remembers this, but I emailed one of my co-founders at FantasyLabs—Dan Fabrizio—years ago trying to get him to hire me. He started a sports betting platform called SportsInsights. We met after he read one of my books and reached out because he wanted to branch out into DFS. I was starting my own company with Peter Jennings at the same time—one that was total dust and we thankfully never launched—and so it was a natural partnership.

Except that isn’t when we actually met. I emailed Dan in like 2012 or something and wanted to start doing fantasy sports content for his company. I guess my email was decent because he called me back interested in working together, but when he called I was so nervous to talk on the phone that I didn’t answer. Then, when I mustered up the courage to call him back, I just hung up once he answered.

The moral of the story: don’t fix your leaks and just get so fucking good at writing emails you don’t ever need to talk to anyone on the phone.

How to Craft the Perfect Email

For the purposes of this post, I’m going to give advice on what’s effectively cold emailing. I’ve found cold emailing to be extremely valuable in my career; when executed properly, it works. There are many different forms of communication that can take place via email, but I’m going to assume for this post we’re talking about emailing someone 1) you don’t know and 2) from whom you effectively want something, whether it’s knowledge, a job, or whatever.

• Most of the work is done before the email.

The email itself isn’t the prize; the email should simply open a door that allows for quick communication of your value. That means actually providing value, which will look different depending what you’re trying to do.

If you’re a writer, you need to have written. If you want to work in data science, you should make public some models you’ve built or other work you’ve completed. This is one reason I think a personal site is very valuable. It isn’t like JonathanBales.com is getting 50,000 visitors a day, but it allows me to very quickly communicate things about myself.

The main thing that’s important here is to show and not tell. It might sound dumb when I say “if you’re a writer, you need to have written,” but you’d be shocked how many people email me saying “I love fantasy sports, I won my league two years in a row, I really want to write fantasy articles.” Then write the fantasy articles. Put them on your own blog or just throw them on Medium or something.

These things need to be completed before you ever consider sending an email to someone. And they need to be super unique and high-value. If you’re unsure if what you’re offering is very valuable, it probably isn’t.

People naturally want to help those already helping themselves. Whether it’s writing, coding, design work, growing a social media presence, whatever…do something that’s publicly visible to which you can refer as proof of the value you can provide. You’d be surprised how far just one high-value demo can get you.

• Show them what you can do for them, specifically.

You can try to cast a wide net if you’d like, but in my experience, it doesn’t work. There’s basically a 0% chance I respond to an email that was clearly sent to a bunch of other people. When someone emails me and it’s obvious they know about me or my businesses or writing or whatever, I’ll typically respond just out of courtesy.

You’re better off sending 10 sick, thorough, and highly customized emails to the top 10 people in your field rather than 100 or 1,000 generic emails. These emails need to demonstrate a knowledge of their business or work, along with solutions that are customized to them. So instead of “I’m really good at Google ads and you guys should do that” it’s “Did you know your competitor XYZ is crushing you in app reviews even though you have a far superior product and over three times the traffic? I’ve built some app optimization systems that funnel the right people into app reviews by first qualifying them. One simple thing you could do right now that you aren’t is ask people who’ve been in the app for more than X minutes or have visited Y times in a day if they like the app, and if they do, ask for a review. The quality and quantity of the reviews should improve considerably and you’ll rank more closely to where you deserve to be. Here are a couple other ideas specific to your app.”

You get the idea. The key to all this is that you’re adept at finding “believable” people for whom putting in extra work is a super +EV long-term bet, even if nothing ultimately comes of it.

• Show them what you can do for them, specifically.

Just as your email should be geared toward the specific person you’re messaging, it should also offer a very specific solution to a problem they have (maybe one they don’t even know they have).

Your email should be customized and offer to solve some specific problem for that person or business. Almost every person we hired at FantasyLabs—about a dozen of them before getting acquired—emailed me in basically in the same manner:

Here’s why I think FantasyLabs rocks, but you could do this better. I’ve done this thing in the past that could help you. I’d like to show how I can help at no risk to you.

As I mentioned in my last newsletter, especially if you don’t currently hold much leverage, you should learn to strategically work for free. Then over-deliver on your promises and, like magic, “Hmmm should we hire this person?” transforms into “Man, we have to hire this person!”

Our head of support, for example, sent me a kick-ass email (which I posted near the end of this article) after we had hired all the interns we were set to hire when launching FantasyLabs, but the email was so awesome we gave him a chance, too. Then Bill went above and beyond in every way, providing all sorts of incredibly useful pieces of data and information from what the guys were learning in support with customers, along with his recommendations as to how to remedy these issues. We hired Bill full-time immediately. From Ian (content) to Sean (marketing) to Colin (data science) and many others, the recipe for success was the same.

A Quick Story About Mark Cuban

The way that Mark Cuban became an investor in FantasyLabs is a sick story. My business partner Peter Jennings runs better than anyone. He’s the definition of a lucky maverick. The guy has just been running super hot since birth.

He managed to find his way into Tiger Jam, which is Tiger Woods’ annual poker tournament. It’s mostly low-level celebrities, pro athletes, poker players, etc., and this motherfucker got randomly seated between Tiger Woods and Mark Cuban.

Peter and Mark talked about a bunch of different stuff—NBA analytics, the DFS landscape, sports tech, etc.—and began emailing after that. Peter just continued to supply all kinds of useful pieces of information, data, and things going on in sports analytics—I mean that decision isn’t that hard to make when it’s Mark Cuban on the other end—including some numbers he thought might be valuable for the Dallas Mavericks.

When the big DFS “insider trading scandal” took place not long after we launched FantasyLabs, Peter emailed Mark and asked for advice about what we should do. The reply email:

“Easy. Let me invest.”

That was the result of the prior months of demonstrating his worth, repeatedly. He was able to show Mark why he’s an asset by actually doing it rather than telling him or asking for anything.

Oh, Peter also won that poker tournament and received a full round of golf with Tiger. He played that this year, and somehow, this was the guy’s foursome:

So if you want to craft the perfect email, just find your way into a celebrity poker tournament and make sure you’re randomly seated between the world’s best-ever golfer and one of the most famous team owners in all of sports. It’s really quite simple once you get to that point.

Some Other Quick Email Pointers

• Keep it relatively short.

Presumably, the person you’re emailing is busy. I know you have a lot to say about yourself, but you’re best off linking to work you’ve done or your personal site or some other way the recipient can learn more about you and your work while still keeping the email readable. In my experience, it’s tough to truly read through every word in great detail when you get a super long email from a stranger. You have to remember, they don’t yet know how much you rock; their natural inclination is probably to think that you suck like the others, because, well, statistically speaking you probably do. So you need to prove why you don’t suck in a very short period of time. If you absolutely must send a few paragraphs, at least add bullet points or some other spacing to improve readability.

• You don’t need a “proper” email. You need one that works.

You don’t need to be overly polite. You definitely shouldn’t kiss someone’s ass. What works is standing out and demonstrating unique value, which means sending an email that’s different than what others are doing. Get rid of the resumes and the “To whom it may concern” and the super formal communication style. I did all that shit and it never works.

• But proofread.

It’s not that I’m a stickler for spelling and grammar, but I mean when someone sends me an email and it has my name spelled J-O-H-N or there’s another misspelling or a clear typo, it just shows a lack of attention to detail. To me, at least, that matters a lot. Your tone can and should be casual, but don’t be a moron.

• If you can’t write for shit, get some help.

If you know you’re not an effective writer, well, work on that. Not only is it a highly valuable skill, but I think writing is the best way to become a more logical thinker, too, as you need to formalize your thoughts and effectively make an argument in a rational way. But you should also get some help in the meantime; ask family or friends who you know are great writers to edit your email.

• Think about everything from the recipient’s perspective.

Rather than simply considering your own interests and how you can get what you want, think about what your email initially means to the other person: nothing. They don’t know you. If a stranger emails you asking for something, why would you respond? What types of things might actually make you get back to them? If you want what’s best for you long-term, do what’s best for others right now. And do it without expectation; you’ll eventually get what you deserve by being generous, but no one owes you anything, no matter how bad you want it.

• Don’t offer to get them a beer or coffee.

This seems generous but it’s kind of implicitly stating “I think your time is worth, like, eight dollars an hour.”

• Don’t ask to “pick your brain.”

Again, this is something that’s a benefit for you. My whole philosophy behind effective email writing is that you’re quickly demonstrating what you can do and already have done that’s in the other person’s best interests to pursue.

• Again, look at what’s on LinkedIn and do the stone-cold opposite.

Emails That Worked

I’ll leave you with a couple strategies that actually worked—those from Colin and Bill, who we ended up hiring at FantasyLabs. Colin’s email explained why things he was already building in PGA could be leveraged into dollars for the company. He attached this breakdown of the numbers.

He put this time into working the math on why his expertise would be a huge net positive for FantasyLabs. Whether or not I agreed with his numbers, he made a serious effort to demonstrate why it would be foolish not to bring him on board. It also helped that Colin won the MIT Sports Analytics “Hackathon” the first two years of its existence, so he had a proven track record of brilliance in sports analytics.

Bill sent this short email:

I saw your tweet earlier and would love to work as your assistant.  I don't want to kill you with tl;dr, so I have my reasons to hire me here, but also attached a cover letter as well as my resume, in case you need that.

1.)  In a recent position, I conducted semi-quarterly Excel trainings to groups of 15-20.  I also hold a master's degree in computer information science.  What I'm saying is, I can probably figure out whatever you need to do in Excel.

2.)  In fact, I've been building a data-driven DFS projection site that pulls data from Excel spreadsheets and adds it to a database.  There's more information about this in my cover letter.

3.)  I have worked data entry in the past and have great attention to detail.

4.)  I can keep giving you reasons why I think I would be great at this and you can believe me or not believe me, but I'm also willing to complete a non-paid trial project if you could come up with one.  That way, we can use my actual work to see if I would be a good fit!

And he had this cover letter attached:

I loved this. First, the email is short. He attached a cover letter, which improved readability and showed some stuff he was working on already. The letter was funny and unique, and think about the impact of the last part of his email:

I can keep giving you reasons why I think I would be great at this and you can believe me or not believe me, but I'm also willing to complete a non-paid trial project if you could come up with one.  That way, we can use my actual work to see if I would be a good fit!

Basically, “You don’t know shit about me, so rather than talk, let me do this work at no cost to you, here’s why you should give me a chance to do that, and I’ll bet on myself to become indispensable.”

The most effective way to market is to build a great product. The email is just the marketing—a way to hopefully communicate your value as quickly as possible.

Before you send any email, remember that you’re the product, and long-term, your top priority, always, should be ensuring the quality of the product.