I cold email insanely successful people and consistently get replies.

When I use the phrase “insanely successful” I’m not referring to people with high-flying careers or a general notion of what most people would consider successful in life.

I’m talking founders, CEOs, and other C-level executives of multi-billion dollar and publicly-listed companies. Plus, world-class athletes — to the calibre of an NFL Hall of Famer and an F1 Champion.

I call this tier of people “ultra-high value individuals”.

I won’t name names, since writing about this already feels cringe enough. But, it's necessary because it can be game-changing for startups I work with — unlocking aysmetric opportunity for the effort put in.

The motive for me emailing ultra-high value individuals is to probe mutual interest in our agendas and explore opportunities. Doing this leads to business results.

Why do it this way, though, rather than get an intro? Through the nature of my work, I jump from one industry to the next a lot.

It’s important to be able to connect with mover-and-shaker type people easily — particularly if I do not have a push-button high-signal introducer I can tap up.

You might think insanely successful people won’t respond to a cold email because their lives are too busy or they just don’t respond to anonymous individuals, but you'd be wrong.

I’ve found the opposite is true. They are ultra-high value individuals for a reason. They’re deeply passionate about certain subjects, efficient and productive with their time, and open-minded in a way a lot of other people just aren’t.

The key to getting a response is how you approach them. Your email copy.

Like all things in life, I wasn’t so great at this at first. But, over the years, I developed a framework that works more often than not.

I’m sharing my approach here for two reasons:

1. To help you connect with super-successful people

2. To make the cold emails super-successful people receive easier to respond to

The cold outreach methodology I share below also generally works for senior stakeholders (SVPs, VPs) that report in directly to the C-suite. And, more generally, individuals that are deeply passionate about their work.

How I do it

Below, I’ve broken down my process into several actionable tasks that are really easy to copy. These tasks accomplish three main objectives:

1. Email open

2. Interest capture

3. Trigger to respond

The outcome of this is a favourable perception and the motivation to reply. You are positioning yourself as someone worth talking to.

What I am not covering here is how to get the target person’s email, that’s a different topic altogether (and the easiest part).

So, here we go.

1. Mutual-interest review

The first thing to ascertain before emailing an ultra-high value individual is to find out what interests and motivates them.

The objective here is to find mutual alignment over a specific subject.

But, what can you possibly have in common with a founder billionaire or a Formula 1 Champion? As it turns out, quite a lot.

It’s usually something they have worked on or have expressed a view on in the past, that overlaps with what you are pursuing to some meaningful degree.

Rummaging through Google, YouTube, or social media will reveal this.

As a rule of thumb, the more specific the subject you have in common, the more compelling it will be.

For example, if you were to email Elon Musk, ‘electric cars’ is way less compelling as subject-matter than specifically referencing a new direction of experimental battery technology his company is evaluating.

If I don’t find a commonly shared interest then I don’t email. There’s no point, since it likely won’t lead to achieving any commercial objective. The ROI for the effort put in is not there.

2. Research

Putting in the time to dig a little deeper and research your intended email recipient makes a huge difference.

The great thing about ultra-high value individuals is they’ve accomplished a huge amount in their lives. To get there, they have usually had to put themselves in the public spotlight and share their perspectives. Or, their work has simply been covered a lot.

This means there’s referenceable material about them online — articles, videos, podcasts, blogs, etc.

I tend to gravitate towards content that features their direct voice such as interviews, essays, and presentations. From consuming this, you can get a sense of what their inner passions and motivations are. Identifying this and tapping into it is key to crafting a provocative email.

As I’m browsing through the array of content available, I bookmark webpages that contain topics or themes which are most similar to the subject I want to discuss with my intended email recipient.

At the end of the research phase, I pick the piece of content that is the most relevant to use for the basis of my email.

This will both act as a hook to engage my email recipient, and, provide a natural conversational springboard to shift the conversation in a productive direction that’s inline with my commercial objectives.

If I want to talk about early-stage investing, I would try to find a piece of content related to that. If I wanted to talk about product or marketing, I would find a piece of content related to those topics.

Sometimes the topic I’m looking for is buried within an interview and isn’t immediately obvious from a superficial review, so it pays to dig. Using ChatGPT can help speed this up, but sometimes it can lack the nuance of picking out subtle points and perspectives.

3. Title Format

The email title you use will have the most influence over whether or not your recipient will open your email after reading it. It’s the most significant variable.

Take the time to get this right. If your recipient doesn’t open your email they won’t reply no matter how good the content inside is.

The good news is, I have a tried and tested format that works. It’s kind of irresistible. And, straightforward.

How so?

All you need is the prior research you conducted (in the previous step) to copy me.

How to do it?

My email title format is broken down into two parts.

The first part is immediately engaging, piques curiosity, and establishes a sense of credibility.

This is another reason I like to use interviews, essays, and presentations as the basis of my cold email content.

It means you can reference the interview or presentation in the first part of your email title.

So, if in your email you are referring to a TechCrunch article that your recepient provided quotes for, you insert it as the first part of your email title:

Doing this creates the possibility in the reader’s mind that the email is about getting coverage on TechCrunch. Or CNN, Forbes, Bloomberg, whatever. Hard to resist opening that email.

You could argue this is deceptive, but it’s not really because you are referencing a TechCrunch article in the content of your email. It’s relevant and the whole basis of why you’re reaching out. It appears sincere.

The second part of the email title should communicate the main theme or subject of the email.

So, if in your email you are referring to ‘generative ASMR’, add it.

I add a vertical bar “|” in between the first and second parts, to clearly distinguish them:

This prepares the recipient for what they are about to read, and it should be a strong area of interest or core passion.

It will amplify the impact of the first part of the email title that refers to a major publication or interview.

Here’s the template:

Using the template, here is what the email to the former F1 World Champion looked like:

👉 This is a real email title I have used that worked (the F1 World Champion opened the email and responded).

Note: it is not necessary to put “Interview” at the start. I just happened to on that occasion (in an effort to make it a little more psychologically potent).

4. Email Body Content

There are a few ground rules I have for the actual email content.

Ground rules:

1. No pleasantries. That means lose “Hope you’re doing well?”

2. Keep it short. Max 10 seconds to read. Keep the copy concise.

3. Include a link. To the media channel content being referenced.

4. Use simple language. No buzz words, Latin, or thesaurus specials.

Apart from that, there’s quite a lot of creative freedom.

But, I do have a general structure that I keep too.

General structure:

1. Teaser sentence. The first sentence should validate it was worth opening the email and provide a strong incentive to keep reading.

2. Mobilising sentences. This should be followed by 2–3 sentences of body content that continue to build interest, curiosity, and rapport.

3. Call-to-action. Wrap up with a specific question, leading to an actionable response.

Let’s go through them.

Teaser Sentence

The first sentence has to achieve a lot.

It is your “MVS”, your Most Valuable Sentence. It’s the first significant element that will be read in the email, and, it also appears as a preview in the email client (like Gmail).

It should be immediately engaging by being personal. And, it should de-arm the reader by answering the elephant in the room question… “What triggered this person to email me?”

It should feel like a natural moment, rather than a contrivance. Sincere, not spam. Sharing, not selling.

Intuitively, to the reader, they must feel like your motivation for reaching out via email (which requires a reasonable amount of effort) is the outcome of a shared curiosity and concern, rather than to purely seek profit.

Often, my first sentence subject concerns the recipient (not me) and demonstrates I have made the effort to take an interest in their endeavors. This helps to establish a common ground and a valid reason why I’ve reached out.

It’s never about me, like “I did this…” or “I’m doing that…”. It never has any pleasantries.

To paraphrase Adam Smith, the key is to probe the reader’s own selfish interest. This will get their attention.

I use variations of the below style format for opening sentences and its remarkably consistent in its success.

Mobilising Sentences

The next 2–3 sentences of body content that follows the opening sentence has the most wiggle room in terms of creativity. There are multiple approaches you can take, so I’ll share a format I’ve found is reliable.

1. First sentence. Pick a specific point your email recipient made in the interview or presentation. State whether or not you agree with that point.

2. Second sentence. Explain why you agree or disagree by providing your own unique insight (value).

3. Third sentence. Provide context with who you are and why your perspective matters (establish credibility).

The key to this format is actually providing a unique insight or perspective.

Stay clear of saying something obvious. And, don’t be afraid to state a view that competes with commonly held beliefs.

Also: feel free to play around the format. Sticking rigidly to it may look and feel awkward depending on the specific context. When using this format, I adjust it each time. That part should feel intuitive — no secrets to divulge here.

5. Specific Ask

Now you’ve got their attention and they’re psychologically invested in your email, it’s time to ask a question.

This is the key trigger that will encourage them to respond. The call-to-action.

Keep this specific. If it’s too broad or ambiguous the rate of response will drop dramatically. They need to know what is being asked of them. Get to the point.

It also needs to require a low friction response and it should tie in intuitively with the main subject of the email. If it’s out of context it feels awkward.

What I mean by “low friction response” is not requiring much from the email recipient cognitively to respond. Don’t force them to have to think too much, or, need to talk to someone else first.

Imagine they are reading your email on their phone right before stepping into an important meeting. They need to be able to feel like they are moving the conversation forward by thumping out a handful of words in an immediate reply.

In your question, don’t ask them to jump on a call. It’s a turn off. You haven’t earned that yet.

Plus, if you genuinely pique their interest they WILL make things happen. There’s no need to state the obvious.

I structure the asks so they can be answered by a simple Yes/No. This makes it minimally cognitively demanding on the surface.

But, I also make them thought-provoking to encourage and allow for a more complex response. If they have the inclination to go deeper, they can.

6. Final Template Example

If your email is a banger, typically you will get a response from the first email. If you do not (assuming there is no deliverability issues), follow-up thoughtfully.

That doesn’t mean asking “Did you see this?”, it means probing and expanding on the dialogue you have already established. For example, provide more context and depth to the unique insight you shared.

Then, keep emailing at regular intervals of 5-7 days. Sometimes, it requires a sequence of engaging follow ups to trigger a reply.

That’s it for today. I’ll be back in your inbox soon. 🤘

Martin

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