WARNING:

This is an eccentric product. From an eccentric person. It will (probably) make you
money and improve your life. But I can’t guarantee that.

This guide is MY answer to the question of “How To Get Clients, Jobs, And
Interviews With Cold Email,” based on MY experience.

But I do not PROMISE you will achieve these things 100% guaranteed. The success
of this strategy depends upon TONS of variables that are outside my control. I can
only show you my method. I can’t make it fit your own context, and I can’t make it
somehow work for you, no matter what. That’s on you to figure out.
TABLE OF CONTENTS

● INTRO

● M.A.G.I.C.I.A.N. METHOD

● CASE STUDIES + BONUS RESOURCES

○ Bonus #1: Cheat Sheet Summary

○ Case Study #1: “How I sent my most controversial email

yet that got a reply from serial tech founder Ryan Kulp
and made me $20K+”

○ Case Study #2: “How I got work with founder of a 30M+

Ecomm Brand (with 5M+ subscribers across platforms)
by sending one email”

○ Case Study #3: “How I got a 2M+ sub YouTuber as a

client less than 6 months into freelancing by sending
one email”

○ Bonus #2: C-Level Leadgen Strategy Breakdown

○ Bonus #3: “OG Classic” Cold Outreach Template

○ Bonus #4: “Replying To Replies” Mini-Guide

○ Bonus #5: My Upwork “Sniping” And Sales Call Strategies

“The Matrix is real, you know," says the 130+ IQ, multi-millionaire, ex-military CEO
sitting across from me.

"There are strange, hidden ways to bend reality, and sometimes that's what you
have to do in this job."

The downtown skyline glints behind him knowingly.

I’m sitting inside a massive corner office, on the 37th floor of the most expensive
office building in the country, and seven pints of sweat are leaking out of my
forehead.

I’m sweating because I’m attempting to wing it through my final interview for my
first corporate job.

I have no internships, no experience, and no connections. It’s a miracle I’m even

here. And I spent my last dollar on the flight in.

If this doesn’t work out, I’m screwed.

The CEO narrows his eyes into a corporate power-gaze™and beams stress directly
into my forehead.

“So I hear you’re a good writer,” he continues.

“Yea, you could say that,” I reply.

He folds his hands.

“So then, if I asked you to describe the difference between say, a gerund phrase
and a past PARTICIPLE phrase…

You’d be able to do that no problem, right?”

Another pint starts pumping out of my sweat glands.

He’s got me.

I try to summon ancient memories of grammar class, but my brain can't move that
fast. I have to say something:

“Well…ahh umm… you know, I’m a BIG unconscious competence guy. So I might
not be able to consciously define the difference right now…

… but I bet I can use it correctly in a sentence without even thinking.“

*long silence*

“I see.”

One week later I’m earning a nice salary, learning new skills at breakneck speed,
and buying a suit to work on the 37th floor of that fancy office building. I have an
incredible mentor, opportunities, and financial security.

And I’ll go on to book hundreds of C-suite meetings that generate millions in

closed deals, with cold email playing a central role in that success.

Fast forward to today, I earn much more than while working far less. I work
wherever I want. And I have a much better network of friends and like-minded
peers I can count on. But no matter what…

I still find the next big thing by sending an email to a stranger.

Email is exceedingly powerful. It can let you bend and shape reality. IF you know
how to use it.

I credit the principles I’m about to outline to you now as the most important
driver of my career success in the modern world. It’s made me hundreds of
thousands of dollars, lifelong friendships, and put me back in touch with destiny.

Turns out Mr. CEO was right. There are strange, hidden ways to bend reality like a
magician.

Email is one of them.

Thank you for checking this guide out. You picked it up to help you produce
positive outcomes in your life using cold email.

That’s your goal, and it’s mine too.

There’s a good chance that means getting meetings and clients. For others, it
might be getting a job or an interview. For some the objective is even simpler, like
getting coffee with a mentor or investor.

My goal is to provide a unique-yet-effective approach to getting those things with

email.

This guide contains two major parts:

My main, slightly supernatural “M.A.G.I.C.I.A.N.” method — for sending creative,

righteous, personalized cold emails that stand out, get replies, win business, and
accomplish pretty much any objective you can think of. It requires effort (like most
things that succeed), and it works. This strategy has gotten me every major win so
far in my career, and can be implemented as soon as today.

The bonus appendixes – containing various examples, scripts, templates, and

breakdowns.

What I do NOT cover in this guide:

Tech stacks and automation tools to scale and simplify all your cold outreach, list
building, and personalization efforts.

Domain creation and warmup information to, again, send cold emails at scale.

This is for two reasons:

1. There are other people who can do that much better than me.
2. I don’t believe in it, it doesn’t work for me or my personality, and honestly, I
think it’s impractical for most people.

With that:

In a lot of ways, what this guide does is pull back the veil on hidden dynamics of
cold email, and, if I may be so bold…

Equip you with a little bit of magical ability.

We’re going to dissect and break down factors I don’t see anyone talk about
online, structure them as a system for sending personalized cold emails, and apply
that system to maximizing your success.

Introducing…

*dims lights and cues music*

THE M.A.G.I.C.I.A.N. METHOD!

You know that little *POOF* sound a magician makes as he reveals his trick?

That’s what we want for your emails.

After all, what do tricks do?

Tricks delight. Tricks provoke curiosity. And most of all…

Tricks elicit a response.

Your email is a little magic trick fired into their inbox.

And while I may have retrofitted principles – and perhaps even fudged a few
words – to make everything fit into that acronym…
I LIKE IT AND WE’RE STICKING WITH IT.

Let’s break it down.

M.A.G.I.C.I.A.N.
Make Yourself Methodless

Let’s kick this off with a little philosophy.

The first thing 90% of people can do to send good personalized emails is DELETE
everything you believe about how emails “should” be.

The thing is…

Most people that start sending cold outreach

are already fighting an uphill battle.

They’re fighting an uphill battle because they assume that cold outreach exists
within this sterile, fixed, pre-established environment.

But the truth is that cold email is not computer programming. It’s not enterprise
resource management. It’s not law. There are technical elements that matter in
the context of cold email, yes, but in a lot of ways it’s a subjective craft and an art.

Because really, when you zoom out and think about it, all you’re doing—all
we’re ever trying to do…

Is establish relationships through

 the medium of text (email).

That’s all that cold email means.

And while that might seem obvious, a lot of people look at cold email as “what
buttons do I need to push to get leads so I can hit 10K/month and afford the rental
payments on my G Wagon.”

Now, a lot of these relationships do have a transactional element to them –

meaning there is a simple exchange – and that means there is a certain rational,
skeptical, cynical, even cold dynamic at play.

But that doesn’t prevent other elements from being important.

For example…

I sell copywriting services with cold email.

Copywriting is essentially a combination of three things:

1) Good Writing
2) Ideas and Creativity
3) Salesmanship

I’m decent at 1 and 3. I am world-class at 2.

So…

I lean into creativity with my cold emails.

Sometimes my emails are the most creative pieces of writing someone has seen in
months or years. In this sense I’m demonstrating my skill set in real time. I go
meta.

But you don’t have to be creative to apply this for yourself.

For example, if you’re analytical, you can reflect this ability in your own style. Your
emails can become about demonstrating your capacity for absorbing data and
pattern recognition.

Because so much of popular discussions on email, cold outreach, and sales

processes in general are about technical elements…

And because so many people who send cold emails have to push high volume to
hit certain KPIs…

VERY VERY FEW PEOPLE USE THIS STYLE OF OUTREACH.

And so, if you apply what you read here… very few people will do what YOU do.

Very few people are sending well-researched, highly personalized messages.

That’s an advantage.

Again, all that’s being attempted with my method is the initiation of a

relationship with another person, with email as a starting point. And remember,
human relationships are not strictly rational endeavors… including those with
clients, employers, employees, founders, investors, and mentors.

So forget everything you know about formal communication, forget all the stiff,
overwrought bullshit that everyone uses in cover letters and B2B messaging.

“Nothing Is True, Everything Is Permitted”

You do not have to do client outreach, job applications, or cold email based on
what other people say is “good” or “effective.” You do NOT have to exclusively use
my method. You do not have to exclusively use anyone else’s method.

Cold email works – ignore people that say “[INSERT THING]” doesn’t work. All
rules can be bent or broken.

In fact, not knowing what the “rules” or “best practices” are can actually be an
advantage, because you have no precepts. This automatically makes what you do
a unique pattern interrupt.

Heck, “unique pattern interrupt” is a great heuristic for my entire cold email
strategy!

As you will see in the examples section, every cold email I send looks different.

The first hurdle of any cold email (including a job application) is actually getting
noticed and read. Nothing else matters if your email is ignored.

Creativity, unique personalization, and having the BALLS to do what 99% of people
won’t tends to help with that.

In that vein, there’s another factor I’ve never heard people talk about, that I call
The Primacy of Your Personal Vision.

When you study the history of founders, executives, innovators, you find cold
email played a role somewhere. Steve Jobs and Elon Musk are good examples.

People that produce amazing results and relationships from cold emails are
always individuals with a clear, powerful, personal vision, who move towards
that vision with passion and positive energy.

I do not care if you think this is woo-woo bullshit. (You’re wrong).

The emotional state you write with matters, the energetic state you’re in matters,
these things impact the effectiveness of your copywriting, and they do that
because copywriting is energetic transference.

People read books because they produce vivid hallucinations in the mind, and
because they produce powerful emotional experiences. Writing is no joke.

Another reason I try to be formless when crafting outreach, is due to the nature of
the inbox.

Email inboxes contain emails (duh).

And yet, they still contain many different types of communication.

Like that reminder from dad about your mom’s birthday lunch. The password for
that subscription you’re trying to cancel. A promotion from your favorite
supplement company. Software reps trying to sell you. A friend trolling you.

Not all emails are created equal. Everyone’s email inbox is a

portal to a variety of different relationships, emotions,
storylines, and commitments.

This means you have options. Different forms to take. We will come back to this
later.

Lastly:

I experience a lot more success from my outreach when I approach it from the
frame of “how can I make this person feel special,” vs “how can I get what I want
from this person.”

Formlessness helps you craft that uniqueness.

When your cold email is a novel, thought-provoking, curiosity-inducing,

dopamine-generating experience in their inbox (compared to the typical trash
they get)...

It’s hard not to win.

Ok, you’ve wiped your software on what cold email “should” be.

Now it’s time to start doing your homework.

 M.A.G.I.C.I.A.N.
Assess The Landscape

This refers to both assessing the landscape of cold email right now, and the
landscape of the types of people you’re trying to reach.

It’s critical to understand that people who receive cold emails, like:

- Founders
- Executives
- HR Managers
- Any other kind of decision maker

Received A LOT of cold email 10 years ago.

And they receive 100x more today.

These people’s inboxes are drowning in bad outreach. Your average executive at a
larger company gets thousands of marketing emails per day.

90%+ of them are 2-5 sentences, use “quick question” as a subject line, include
1-2 elements of basic personalization (usually via AI tools that scrape names and
other data from profiles), and end with a CTA that asks “can we find time for a
call” or “can I send you ____.”

People are cynical these days. They know the patterns of mass-produced cold
email.

If I get an email from someone I don’t know, and the first line is “Hey Alastair,” I’m
already starting to think it's a sales blast.

If the next line is about how great they are (“we’ve worked with ____ like you to
help ____” or “would you be open to discussing ____”), I KNOW I’m on some
scraped list and the person sending this email doesn’t know anything about me.
Instant delete.

This is why every single one of my cold emails revolves around:

1) A Good Pattern Interrupt

2) Demonstrating Credibility ASAP

I do not pitch, persuade, or ask for anything until I have first done these two
things.

Understanding this meta-context lets you figure out what a good pattern interrupt
looks like, and what demonstrating credibility looks like.

The key to both: context.

And if there’s one thing that all my successful cold emails have in common…

It’s an accurate understanding of context.

“Content is king. Context is God.” - Gary Vee

What do I mean by context?

Context is the set of variables, environments, conditions, wants, needs, and pain
points your target is operating within.

Again, this includes their specific context, AND the context of cold email in
general.

A head of sustainability at an oil and gas company exists in a context. So does a

founder in Silicon Valley. So does a billionaire telecommunications executive and
philanthropist.

(I’m thinking here of specific people I’ve booked meetings with via cold email)
These people operate in certain landscapes under certain conditions.

Cold email recipients are inherently an unaware market.

They don’t know who you are. And so there’s always an inherent credibility
challenge.

When you can show up in someone’s inbox with an accurate understanding of

context, you mitigate that credibility issue.

Context is also how you decide WHO to reach out to.

When I wanted to get The Futur as a client, I considered emailing their founder
(Chris Do) directly. But I ultimately decided against it.

After learning a bit more about the type of company they are, I realized they had a
bigger org chart. Internal marketing hires, plus a COO, CCO, finance, admin. So it
was safe to say Chris had delegated a bunch of stuff, probably had a super
ambitious long term vision, and hired full time people to help scale.

He wasn't going to be directly involved with email or copy — that’s at least two
levels beneath him. Someone else is running that marketing show.

Also, he was just a bit too high-profile. I would email a 250K youtuber directly, or
maybe even an 800-1M sub youtuber, depending on their biz model.

But The Futur is a larger enterprise with 3M+ subs, a physical office, they’ve been
around for 8+ years, they have a big content team… the chances of Chris seeing
or replying to a cold email were slim.

So I did a bit more digging and ended up reaching out to a Director.

See, it’s not always obvious who you should be contacting.

For example:
If you’re applying for a sales role, you DON’T want to only submit your application
via the online portal, or ONLY contact the hiring manager.

(Side note: if you’re trying to get a sales job, or find a new higher-paying sales job,
I HIGHLY recommend picking up Kellen Casebeer’s Get A Remote Sales Job Guide.)

Good landscape assessment includes thinking critically about WHO you’re trying
to reach.

Is it:

A sole proprietor?
Small company (1-10 employees)?
Medium sized company (10-50 employees)?
Large company (100+)?

This dictates who you send to, which dictates your research, which dictates your
message.

A basic LinkedIn search w/filters, potentially combined with a look at their website
should suffice here.

Personally, I’m biased towards aiming high.

Meaning you should (usually) aim for the highest person on the totem pole.
CEO, Founder, etc. (provided your message is at least somewhat relevant).

Personalization and high quality outreach help you get away with this. Senior
people are generally more intelligent, more knowledgeable about the business,
and more capable of recognizing quality talent.

If you impress them -- even if they aren’t the relevant decision maker -- they’ll
forward your outreach to the right person (who is now forced to give you the time
of day).

Ok, you understand the broader landscape of cold email, and the broader context
of your prospect.
But it’s not enough to craft good personalization.

For that, we need to…

M.A.G.I.C.I.A.N.
Gather Specific Information

Now you have a target in mind, and a basic understanding of the context they
operate in. Let’s touch on research.

We want to know specific information about the person/company. You can be

crafty with this.

There are obvious and non-obvious ways to find details on people, and generally,
the more “important” they are, the easier this is. Pretty much everyone has some
sort of tidbit on themselves out there, it’s just a matter of putting in the effort to
uncover it.

I never send cold outreach without good research. It’s the basis for your
personalization. In terms of finding info…

Most people understand basic research like website bios, etc.

Some other things you can cover:

● Who do they follow on social media? (what’s their worldview?)

● What apps, plugins, and tools are they using for their website? Use
builtwith.com to figure this out. If you’re selling Klaviyo services, it helps to
know if a prospect, uhm… actually uses Klaviyo.

● Do they have an email opt-in, something you can subscribe to, to figure out
how they’re structuring their email marketing? (apply this to any other
 aspect of their biz like ads, ops management, content, etc)***

● ***Deeper Example For Email Marketers***: you can combine

builtwith.com with semrush.com to figure out what tools companies use
AND how much traffic they get. Based on this, you can estimate stuff like
revenue. Let’s say a supplement company uses Klaviyo. They will likely
convert around 1-5% of website traffic to their email list. Then, 2-10% of
those conversions will go on to convert into sales in their welcome
sequence. (You can opt-in to the list to figure out the quality of that
welcome sequence and refine that conversion estimate.) Multiply those
rates by average traffic from semrush, and you’ll have a decent estimate of
attributable revenue from email (and thus figure out if it’s worth your time
to even reach out).

● Do they have writing online? (How do they talk? Mirror their language.)
○ Using their own phrasing in your messaging unconsciously builds
rapport

● Do they use social media? (How do they present themselves to the world?)
Maybe they have a personal account you can find, because they follow it
from their business account.

● What kind of language do they use in formal business contexts? (Like

earnings call transcripts, for example) Are they stiff and formal, or informal?
(again, mirroring)

● Are there any features of them or their business in articles or media

publications? Any interviews on YouTube or podcasts where they give away
more info about themselves or their business?

● What aspects of their business are currently in-house vs outsourced?

● Are they currently running ads? Do they have any funnels in place you can
opt-in to? (this tells you what they’re prioritizing in the business)

● What other companies, agencies, or service providers have they worked

with in the past?
 ○ You can often find testimonials or case studies via google search (I did
this for my Kevin Espiritu example, detailed in the appendix section)

● Are there any “linking factors” between you and them (like mutual accounts
you both follow on X or IG, LinkedIn connections, or even products you both
use)?

Understanding context and performing good research matter because:

Context + Research + Personalization = GOOD ASSUMPTIONS

And…

GOOD ASSUMPTIONS = INSTANT CREDIBILITY

The thing about good research is it lets you make those intelligent assumptions
that instantly establish credibility.

(Remember from the last section: In the current meta, you want to do two major
things in every cold email. 1. Present A Good Pattern Interrupt 2. Demonstrate
Credibility ASAP)

“I understand XYZ Agency did some Klaviyo work for you, but didn’t meet your
revenue expectations”

“I understand growing the financial services practice is a priority for the firm, for
the next several quarters”

“I understand filling ___ role is critical as there have been issues with talent
retention”

These are examples of good assumptions.

Bad outreach contains bad assumptions, like “Hey do you want this random
software?!” or “HEY, if I could get you 100,000 sales calls in 72 hours would you
pay me??”)

Making assumptions about someone and their business is a GOOD THING. They
just have to be accurate.

Gathering specific information lets you make accurate assumptions about people,
their life, and their business.

Presenting these assumptions (early on) in cold emails helps establish instant trust
and credibility, which you need to do in the current context of cold email.

You can figure out email addresses quickly and freely, if you know the patterns to
look for. Here’s how:

● Identify the contact’s first and last name and company domain, aka
www.companyname.com

● Consider the most popular forms of email address configuration:

firstname.lastname@companyname.com, f.l@companyname.com, etc.

● Go to either email-checker.net, emailhippo.com, hunter.io, or any other free

email confirmation website and check if the address is valid. (a simple “free
email checker” google search will pull all these up)

If you end up sending to an incorrect address, the email will bounce. You can keep
trying variations until you don’t get a bounce message.

There are a bunch of other tools to help with getting contact information, like
LinkedIn Sales Navigator, Apollo, Instantly, and dozens of others. But I’m not going
to cover that as it’s fairly self-explanatory.

Let’s move on to winning angles.

 M.A.G.I.C.I.A.N.
Identify Your Angle

This is all about taking all your research and your understanding of the broader
context, and narrowing it down into a specific message – aka specific sentences.

I believe in hyper-personalization. But the thing is…

Personalization does not equal “PeRsOnALiZaTioN”

Some people run into an issue with research, where they think it’s about: “hey I
noticed you like football!”/”hey we both went to the same college!”/”hey I read
your blog post!”

Not so.

Rather:

Good personalization is about demonstrating your

understanding of a specific and current business problem.

That’s a winning angle. That’s your core hook. That’s what will drive a response.

Another issue with research is sometimes you end up with too much of it. You end
up with multiple different angles you can use. Maybe there’s a specific business
priority, plus a missing piece in their business, plus a shared interest or worldview.

And sometimes you have to decide what to run with. Otherwise you end up trying
to cover 10 different bases in one email (bad idea).

Here’s how I cut through the weeds on that.

 My favorite angle to use in a cold email is the
“Understanding-And-Belief-Wombo-Combo”

A) “I understand that [ASSUMPTION ABOUT SPECIFIC BUSINESS CHALLENGE]”

B) “I believe I can [YOUR SOLUTION TO THAT SPECIFIC CHALLENGE]”

This is the crux of many successful cold emails.

A formal example of the Wombo Combo in action:

This was sent to the head of one of the largest and most prestigious marketing
agencies in the world, so it’s formal in tone.

There are other elements and flourishes that can supplement a message like this –
like humor, references, and other forms of “packaging” and “presentation” – but
competent messaging like this is the meat and potatoes.

This is the substance that speaks directly to the needs of the prospect, and the
driving force behind the results you get.

This applies even if you're just trying to get hired. (Their problem in that case =
finding the right talent and being able to confidently move on from “hiring” mode,
knowing they’ve found the right person for the job.)

Now, all that said… I have seen the “we both love the same football team!”
personalization style work. I think it can work well for building rapport as you
move deeper into a sales relationship.

But for cold outreach, these days, I think that style needs to go above and beyond.
Stuff like sending an autographed jersey, or Cameo vid from a retired player.

Which isn’t in scope for most people.

Remember:

Understanding And Belief = Your Core Angle

Some variations on the Wombo Combo:

In a lot of these I’m sharing direct sample work instead of writing “I believe I can
help.” It’s always better to show, not tell, provided you have relevant examples.

Ok, that should give you a good sense of what good angles can look like, via the
Understanding + Belief Wombo Combo.

Let’s get in the lab and start cooking.

M.A.G.I.C.I.A.N.
Compose Your Outreach

Time to write this bad boy.

First off:

1) Leave The Subject Line Empty

You can still have one in mind at the beginning, but leave it blank for now. You
might change it. Your subject line might become informed by the content,
specifically the first few lines (pattern interrupt). You can always come back to the
subject line at the end.
2) Leave The To: Line Empty

You don’t want to accidentally hit send before the message is complete (like
someone I know who definitely isn’t me because I’ve totally never EVER done that
before by mistake… hehe). Put their email address in at the end.

3) Confirm Your Objective

Define your objective at the outset. Are you aiming for an interview? A sales call?
A reply? A referral or forward? Every cold email has an ask. That ask needs to be
clear, simple, and singular. Don’t ask for an autograph, AND a phone call, AND a
job interview. One objective. One ask.

4) Craft Your Pattern Interrupt

What are you going to do to make your email stand out?

A good example:

Notice how the subject line leads right into the first lines of copy. The question in
the subject line is creating curiosity and it’s making specific references to specific
people.

This pattern interrupt is generating curiosity AND proving that this email is a
unique, 1-to-1, personalized message. NOT automated.

Another example:
The subject line is a reference to a post he made about needing “s-tier” copy.

“So you need S-tier emails” is unique, relevant, and definitely getting opened.

(This got me the meeting+work btw)

Another example:

“What’s up” and “This will either be the most interesting or most confusing
email…” are basically demonstrating “Hey I’m not a robot and this email is not
from a robot.”

Success:

Anotha one:

Here I’m mentioning the book the guy wrote (specific info!)

ANOTHA ONE (jeez it’s almost like I practice what I preach):

This one’s basic. “NAME, love to see it” is honestly a weird subject line. That’s
pretty much it. It stands out and hints at some sort of specific reference to
something he’s done in the email body. He’s also a dancer like me (receiving a
sales email that ALSO mentions a hobby you enjoy, like dance, is a pattern
interrupt)

Success.

In this example I literally wrote an entire fake story involving the recipient and
other characters. Massively creative pattern interrupt. I break down this email in
full in the appendixes.

Side note: never ever use “Dear” to start your emails, as in “Dear John.” Use
hey/hello/hi. Literally anything but dear. Trust me.

THE BOTTOM LINE ON PATTERN INTERRUPTS:

They stand out, generate curiosity, hint at something valuable, and indicate the
email is from a real person (usually by making specific references that are
relevant to the prospect). Creativity is your best friend here. Be creative, but be
strategic with your creativity. Because you still need to…

5) Demonstrate Credibility
Here’s where you drop that Understanding + Belief Wombo Combo we talked
about earlier.

PART A: UNDERSTANDING

“I understand XYZ is happening”

You’re demonstrating you know what’s going on in their world. You’re

demonstrating that you took the time to research them and their business.

There are other options and variations here, including:

- references (if you both have a mutual acquaintance who referred you… “David
suggested I reach out regarding _____”)

- direct sample work (“I noticed you didn’t have a welcome sequence in place. I’ve
written a sample of what that could look like”)

- assumptions (you can say “I assume XYZ is happening” if you’re not 100% certain
about the facts)

Whatever you go with, you’re ultimately acknowledging what’s going on with

them in some way. You’re demonstrating an understanding of their goals.

Bottom line:

You want this sentence to summarize what you think the most
important problem or paint point they have is… that is also
relevant to what you do.

This can get tricky with bigger businesses and well-known people.

That’s because they have a BUNCH of options for any kind of challenge or pain
point. They already have relationships with other service providers, consultants,
and employees that solve this stuff.

However, you can get around that by simply ACKNOWLEDGING IT.

Example:

Notice how I acknowledge his position: he has tons of options and solutions that
are already vetted. Notice how I include specific references to specific information
I’ve gathered about his business.

Notice how I make GOOD ASSUMPTIONS about what’s going on in his world.

You get the idea.

PART B: BELIEF

“I believe I can help”

Here is where you transition from them to you. However, even though you’re
starting to talk about yourself, you still want to make it about SPECIFIC BENEFITS
THEY WANT.

“I believe I can increase the conversion rate on your opt-in and welcome sequence
to add another 10% of revenue from email”

“I believe I’m a better fit for the ___ role because of ABC reasons.”

“I believe I can solve the ____ challenge you’ve been dealing with for 6 months
using the XYZ method I’ve developed…”

Keep this fairly short. You can even cut the “I believe” and just say “I can ____” or
“Confident I can _____.” Whatever suits your own style and voice best.

The main thing is you don’t want to go on and on about how you help. Save the
details for a call. You always want to leave room for curiosity, because…

CURIOSITY IS HUGE FOR ANY KIND OF SALESMANSHIP (like

cold emails, sales cycles, and job applications)

Don’t go overboard on describing how you can help. Keep it concise, keep it
specific, keep it relevant to what their needs and wants are.

Now, a lot of people that need to use cold email don’t have much previous
experience, case studies, or general credibility. Let’s spend some time on that:

“What If I Don’t Have Credibility Or Experience?”

The basic point is that spending more time on research, personalization, and
gathering specific information is going to help you compensate for this. But
there are some additional options to consider:

1. You can also use your research to create sample work that demonstrates your
ability. Showing up in someone’s inbox and being able to say “Hey John, I put
together [useful resource/sample work] for you. Figure they could be of use. Let
me know if you like what you see” is a good workaround for lack of experience.

2. Another technique is to “make the skeleton dance,” which Ben Settle talks
about. This is taking your weakness and flipping it into a strength. “I actually
have no experience with _____, which I freely admit.” Making admissions like
this builds trust. You can even tell a story about it to help get them on your side.

3. Lastly: focus on getting the person to like you. Make the first priority being
funny, relatable, and likable. Likeability is a HUGE variable in business. People
want to do business and hire people that they enjoy spending time with.

Lastly, don’t blindly copy anything from my examples. Find your own way to
thread the needle.

Go back to the previous section with my examples if you need extra inspiration.

6) Make Your Ask

Now, you’ve caught their attention with a pattern interrupt. You’ve demonstrated
you’ve done your homework and know about the challenges they’re dealing with.
You’ve stated how you can help with that.

Time to make your ask.

Remember: a cold email is about building a new relationship. It becomes easier to

build that relationship speaking directly on the phone, over video, or in person.

I generally want to get a phone conversation with anyone I’m interested in, but
you might have a different type of ask. Whatever it is…

Always make your Call To Action simple and clear.

 Make it easy.

If you’re asking for a phone call, ask for a SHORT, BRIEF phone call. 10, 15 minutes,
tops. NOT 1 HOUR.

Generally: the bigger the ask, the bigger the email needs to be. I’ve sent 50 word
cold emails, 500 words, even 1000+ words. Long emails can work, but they
increase your risk of being ignored.

Be chill with your asks too.

“I’d like to find time for a 10-minute phone conversation. Please let me know if
that works for you.

“Let me know if you want to chat further.”

NOT “I’d love to book 130 minutes to present my slide deck with 10000 slides on
our proprietary technomatic method that can do this and that and this and this
other thing…”

Just a clear, singular, non-psychotic ask.

Another important point here:

TAKE OUT THE ADMINISTRATIVE WORK OF THE NEXT STEP.

You basically want to function as their Executive Assistant. You want to be the one
setting up the calendar invite. You don’t want to leave that in their hands, or, God
forbid, send them a Calendly link. After all, you’re the one showing up
unannounced in their inbox. The onus is on you to make stuff happen.

“Feel free to let me know some times that work for you, and I’ll send over a
calendar invite.”
 SIDE NOTE: **If You’re Applying For A Job**

If you’re using this guide to increase your chances of getting a job:

Always send emails directly to company contacts. Don’t just submit via the
online portals. This means you might want to find MULTIPLE emails for a few
different contacts at a company, and send your cover letter/resume along with a
short note:

“Hey NAME, I just applied to ROLE. I’m serious about the opportunity, and
figured I should go a bit further in demonstrating that by sending my details
directly to someone who might be connected to the position.

If you’re willing to forward this to the right person, that would be very much
appreciated.

Your Name”

Something like this increases your chances of being seen, demonstrates your
willingness to put in extra effort, and can open up a conversation with someone
inside the company who can potentially help you get hired (or give valuable
information to help you prepare for interviews).

Successful example:

To conclude:
1) Figure out your pattern interrupt and craft a good opener that will capture their
attention in a crowded inbox.

2) Demonstrate credibility quickly by showcasing you’ve done your research,

understand their situation, and have a relevant solution or way to help them with
their problem.

3) Make your ask as simple, direct, clear, and easy as possible.

Once you have all these elements in place, you can go back to finalize your Subject
Line and prepare to send… BUT NOT YET.

You’re almost ready to fire it off.

But if you’re TRULY committed to going above and beyond in the cold email game,
then it might be wise to…

M.A.G.I.C.I.A.N.
Include A Finishing Touch (Optional)

“Go Ahead, Make My Day”

Your email has a good pattern interrupt. It establishes credibility quickly. It’s
personalized. It has a specific ask.

But… it's always nice to add one or two things that help make someone’s day. We
want your email to be the most memorable part of that person’s shift. We want
them to share it with a colleague. Refer to another decision maker. Print it out for
review.

Doing one last once-over is a good way to spot opportunities for this. Something
will stand out.
A couple potential options:

1) Providing Free Value

If you notice some simple, easy thing they can fix right away, that’s a nice layup. In
this example I mentioned a broken link. (I sometimes do this just to get a discount
lol)

2) P.S. sections

P.S.’s are great tools to squeeze in one tiny bit of personalization, curiosity, or
detail about yourself.

“P.S. I noticed you have a typo on the front page of your website” demonstrates
attention to detail and again, ADDS FREE VALUE.

“P.S. If you interview me, remember to ask me about ______” generates curiosity
with a hiring manager. (shoutout to Daniel Throssell for this one, an outstanding
copywriter and a big influence on me)
I usually look at P.S. as one final dose of curiosity. Don’t overuse it though. Not
every email needs one.

I sent out a marketing application to test all these methods. Got the interview.

3) Jokes or References

This is where you can use some of the basic personalization facts you might have
gathered. Stuff like “We both went to ____ college” or “Go Raiders!”

Not hugely important, but it can push your email over the line; from good to
great. Humor can be risky though, so use it wisely.

Again, this stuff is optional. But it’s usually worth taking the time to do one last
review of your email, and see if there’s any room to insert a cute little reference,
joke, free value-add, or P.S.

M.A.G.I.C.I.A.N.
Appear In Their Inbox

Now you’re ready to send. I’ll keep this section brief.

If I’m going after an executive, I’ll usually send in the early morning. Sometimes
late evening, sometimes I’ll try a weekend. I tend to avoid the middle of the day.

Generally, the earlier the better. You want to be sitting in their inbox, waiting for
them to open it and see your curiosity-inducing subject line. People also have
more energy earlier on in the day, which increases chances of a quick reply.

A lot of people also have backup email accounts or personal gmail accounts.

You tend to find these on their website (personal blog), and sometimes they’re
even available in YouTube channels (under the Channel Details section). Hunter.io
can sometimes get you these too (for free).

It can be wise to find these additional addresses and CC them.

I would also recommend sending a note to their LinkedIn, X, or other social

account. You can either copy the email directly, or just let them know “John, just
sent a note to your email re: _____.”

This is all about maximizing your chances of being seen. You’ve already put in the
work to create a personalized outreach, may as well go the extra mile to make it
visible across all their digital channels.

Also, before you hit send…

I recommend testing your formatting by sending your email to one of your own
email addresses.

ESPECIALLY if you’ve copy pasted any content into your email client, or are using
different font sizes. Sometimes formatting can get messed up by gmail, Apple
Mail, etc.

Finally, let’s touch on additional points on subject lines, just in case you’re still
struggling to find the perfect one before you hit send.

Ideally, your subject line linked directly into your pattern interrupt. If not, you
have some other options.

Super short ones can work well:

John, interested?
Interested?
Note for John
John: quick note

Name + unique information is another good combo:

NAME, noticed this on your Wordpress site…

NAME, what happened at FORMER EMPLOYER?
NAME, I know what you did last summer (jk)

If you know accounts and various public figures they follow…

(which you should, because you read the Gather Specific Information section, and
applied the advice… RIIGHT? :))

You can use a reference to that in your subject lines or followup, especially anyone
they might have a strong emotional attachment to, like a comedian or
unconventional writer.

I.E. “What NAME and Bill Burr have in common”

Bottom line: use a subject line that has the best chance of capturing attention
and generating curiosity, while still being relevant to your email content.

Ok.

You’re ready.

Say a prayer to the email gods and fire away.

Then…

M.A.G.I.C.I.A.N.
Never Stop The Follow-Up
Once you get started sending cold emails, you’ll notice:

Sometimes you don’t get a reply.

This is normal. And it’s why you follow up.

Most people won’t do this because they’re afraid of “bothering” someone.

Cold email in any context is first and foremost a sales and marketing effort. You
are a salesperson. You are selling at all times, at all points in your life. Do not run
away from this fact. Embrace it. Most people don’t even get to a psychological
position where they CAN send cold emails... because they’re afraid of selling
themselves and afraid of rejection.

However, while you do want to follow up…

Don’t be impatient and/or rude.

Sometimes I get replies to emails 1-2 weeks after sending.

People are busy. Sometimes they just need time.

Sometimes I’ll even break my own rules and not follow up, because I know my
first email was SO GOOD… I have this intuition they’ll reply soon.

But I don’t recommend waiting forever.

I guarantee if you look at all top performing sales people…

The vast majority will be consistent and determined in their followup.

And the thing is, if you’ve done your homework, and you’ve sent a good email,
and you’ve sent it to the right address…

You should feel justified in following up.

That’s part of the rationale behind this approach too. You put in the effort so you
feel CONFIDENT about sending multiple follow ups, and don’t feel like you’re
pestering the prospect.

Quick story time:

I once wanted to book a meeting with the Global Head of Risk Management at a
large Life Insurance Company.

So, I spent a couple weeks putting together my outreach. I sent it off. I followed up
half a dozen times. I cold called him. I cold called his secretary.

Nothing.

Eventually, I found out he was giving a talk at the local university. I bought a ticket
and attended.

I cornered him after the talk and pitched him face-to-face. He asked me to send
him some additional materials.

I spent another day putting together a personalized slide deck, and emailed it
over. Waited a few days.

Boom, got the meeting.

All in all…

-2-4 weeks researching, preparing campaign

-physical letter mailed
-cold call follow up in 10 days
-tons of calls, multiple attempts to get a pdf copy of the letter through the EA
-7-8 email follow ups (I knew he was opening and reading)
-Found out he was giving a talk at local business school
-Went after hours, sat through talk, caught him after to give a copy of our
founders book and pitch eye-to-eye
-he STILL wanted more, asked for a deck
-scrambled to put together deck in the next 24 hours
-got email from the EA a few days later to book a meeting. Success.

I know people that have sent 30+ follow ups to get a client.

Sometimes success is doing what 99% of people won’t. Relentless followup is one
of those things.

Remember: You’re Not Annoying. Plus, No One Cares.

People get hundreds of spam emails and meaningless messages they don’t care
about. Many are totally fine with someone bumping up in their inbox (even if
they’re a stranger). You’re not annoying and no one cares anyway. Besides, don’t
you have bills to pay? Balls the f**k up and hit send.

Of course, this all begs the question: how should you follow up?

Traditional cold email advice will tell you to provide additional value in your follow
ups. And it’s not bad advice. You can include a Loom video, additional context,
helpful suggestions, stuff like that. The problem is, if you try and “provide value”
in follow ups without successfully crossing that initial trust/credibility barrier first,
you’re still probably getting ignored.

I think as long as that first email you sent is high quality, and includes the
elements we’ve spent this guide talking about, it’s fine to make your followup
more basic.

“John, wanted to make sure you saw the above note. It’s sincere and I did my
homework. Please let me know if I’m on the right track.”

However, you can ALSO personalize followup, like in this example:

I knew the guy was a fan of Thomas Sowell, so I found this pic of him. It worked.

The thing about “funny” or “entertaining” follow up is it’s often just as valuable as
traditional “value.”

Everyone checks their email. Everyone is bored. Everyone is online. Making

someone smile or chuckle is worth something too. It’s not always about facts and
data.

Bottom line: follow up until you get a yes, get blocked, or get told to f**k off.

Happy Hunting.
 CONCLUSION

At this point, this might be the most comprehensive (and ONLY) guide on
personalized cold email ever made. I’ve tried to be as complete and careful as
possible in putting this together.

Which is fitting, because a lot of my philosophy is about genuine care. When you
genuinely care about yourself, your goals, and the people you’re reaching out to,
your results improve. People are smarter than we think, and can tell when
someone’s put effort in.

There are a million different variations to my method. You can add, subtract,
multiply and divide it however you want. Make it work for your needs. But by
applying these principles (and perhaps a few tactics)...

You can get your email read by anyone.

You just have to make it exceptional.

You have to make it…

M.A.G.I.C.A.L.

I sincerely hope this guide helps you get what you want out of life.

Because when you win, the whole world wins with you (including ME).

Happy hunting.

BONUS RESOURCE #1
CHEAT SHEET SUMMARY
 CASE STUDY #1
“How I sent my most controversial email yet that got a
reply from serial tech founder Ryan Kulp and made me
$20K+”

This one is pretty funny.

Ryan Kulp is a serial SaaS founder and an interesting internet character. He first
came on my radar as an acquaintance of an acquaintance. I knew he had read
some of my emails for a client, Greco Gum, and enjoyed them.

So, while doing a round of business development, I decided to send him a nice
juicy serving of M.A.G.I.C.I.A.N. Method.

Feast your eyes:

BREAKDOWN

Subject line + first line:

Clearly a pattern interrupt. How many people have received an email with the
“r-word” in the subject line?

This pattern interrupt is actually based on research. On Ryan’s personal website,

he refers to himself as “slightly retarded.” So I’m mirroring his own joke back at
him here. It’s also a little bit of self-deprecating humor to disarm him.

Second line:

Next, notice the “My assumption” line. (yes, see how I ACTUALLY use my own
formula? Unlike some out there…)

Ryan has old blog posts about copywriting. From before I even started as a
copywriter. And he has tons of writing posted in general. He’s a successful internet
entrepreneur, so by default he’s going to be a pretty good copywriter. I
acknowledge this in a way that further disarms him AND demonstrates my
competence (the fact I can deduce that sort of thing and communicate it in a
subtle, friendly way).

CTA:

Very chill, very low-effort CTA. I really like using the “wanted to put myself on your
radar” line. It positions yourself as a helpful resource, available when needed
(almost like a hotel concierge). If you provide services, you want to have this
service-based mindset (again, almost like a high-end Hotel Manager).

So… how did I make 20K+ from this email?

Well, Ryan posted it on his Twitter and it BLEW UP.

It got a ton of engagement. I got dozens of inbound leads from this. (including
some BIG companies and startups). The comments were hilarious too:
There’s an important point to notice here:

Good personalized cold emails can also act as a form of guerilla marketing if
shared online. Even if you don’t get your original goal (I still did), you might get
other benefits (as I also did).

CASE STUDY #2

“How I got work with founder of a 30M+ Ecomm Brand

(with 5M+ subscribers across platforms) by sending one
email”
This is a breakdown of my email to Kevin Espiritu, founder of Epic Gardening.

Kevin is a well-known YouTube personality and Founder of Epic Gardening. I knew

he would probably recognize some of my other clients, as I’d done some work
with other YouTube-based businesses.

I also knew he’s an intelligent, motivated founder, and would probably respond
well. He needs plenty of copy for his company AND his personal brand. He
understands copywriting, marketing, and what top talent looks like in that
context. So, I felt confident taking some extra time to put together a good email. I
made it a little longer than usual, because I know he’s smart enough to ride with
it:
I went with a question-based subject line that references the specific YouTubers
he would know. Obviously, I’m trying to trigger curiosity here and make him think
“damn, what DO I have in common? I gotta open this.”

Next, I immediately establish credibility by mentioning these other YouTubers

have hired me.

I throw in a little humor with the “stop referring to him in the third person” line.
That was a “Finishing Touch” I added later.
Then I move into my wombo-combo.

I demonstrate I’ve done A LOT of research by talking about how his business
works, how he’s worked with another agency (Pear Digital), and how I know he
doesn’t need some basic copywriting service.

I don’t know what his active priorities are, but I can make GOOD ASSUMPTIONS
about them. Which I do next.

Then I shift into how I can help. I hint at a potential pain point by mentioning how
I’m “confident I can successfully write in his voice” (this is a rare quality for most
copywriters) “and help separate you from anyone else” (he’s competing against
other founders and internet entrepreneurship personal brands).

Finally, my CTA is chill. “If you want to chat, let me know. Otherwise, I’m here.”
Simple and low pressure.

Results:

“One of the best outreach emails I’ve ever gotten.”

We went on to do some trial work together. This is a dream client for anyone
selling any kind of service online. He gets hundreds of pitches a day, guaranteed.

This is how you cut through the noise with personalized cold email.
 CASE STUDY #3

“How I got a 2M+ sub YouTuber as a client less than 6

months into freelancing by sending one email”

Context:

The client was The Futur/Chris Do, a large business and design education
company.

Chris is very popular online... he's one of those high-profile influencers with a
strong cult of personality (although I'd never heard of him until this year). My
guess would be his company does around $10M in revenue per year. Maybe
$10-30M.

I started freelancing in January 2023. By June, I had signed the work agreement.

In May, after getting enough regular work to pay the bills, I put together a "dream
client" list, and The Futur came up during research.

I like art, I'm an artist myself, and I'm passionate about helping creative types
make more money. Seemed like a good fit.

I figured out context on the company (as discussed in Assess The Landscape). Did
a bit of digging, added details to my list, and sat on it for a bit.

Then, a few days later...

I woke up with a strong gut feeling I should go check out the brand again.

I’m often intuitive in this way when prospecting. I’ll pay attention to how I’m
feeling about a prospective client, how easily I can think of messaging angles, how
easily I can imagine writing for their business...

I went to the website again and noticed an open application for "Email Marketing
Specialist" in their careers section. Had missed it before.

There were some requirements. It was clear they wanted a full time hire (at least
after an initial trial period).

Of course, I knew I didn’t want to work with them on a full time basis. I wasn’t
going to submit a cover letter or resume. Fook that shit!

Instead…

I was gonna stand out, bank on a lil sales jiu jitsu, and convince them to pay me
as a contractor!

The posting asked for the standard stuff: “include samples, tell success story, why
do you want to work with us, desired monthly rate, bonus points for creativity,
etc”

My default style is heavy on personalization and honestly… kinda weird and

outlandish.

So I started to cook something up along those lines. Can be risky, but it works to
get attention.

Here’s the email I ended up sending to the marketing head. The screenshot is too
large, so I’ve reprinted the text:

SUBJ: The Telepathic Application for Email Marketing Specialist

“Email is dead.”
Chris Do ripped off his headset and hurled it across the room. Fuming, he stormed
into Carrie Green's office:

“CARRIE, IT’S OVER!”

Carrie sighed. She knew what was coming, but played along anyway.

"Uhm...what's over, Chris?"

“CARRIE, generic marketing guru #9000 just informed me email marketing is dead.
It’s over. We’re shutting it all down.”

Carrie rolled her eyes.

Always so dramatic...

“Chris, I’m not sure that’s a good idea--“

"SILENCE! Drip has FAILED US. Unless you can overhaul our stuff RIGHT AWAY, I'm
canceling all Futur emails FOREVER."

Chris stormed out of the room, muttering something about being late for Dubai...

Carrie shut the door behind him and sighed.

"Whew, that was unexpected. What am I going to do about this? Seems like he's
serious this time--"

*PING*

Suddenly, a strange inbox notification popped up on her screen.

*The Telepathic Application For Email Marketing Specialist*

"Hmmm...looks like someone's applied for the email position."

"Odd timing," she thought, and began to read:

-------------------------------------------------------------------------------------------

Hi, Alastair here.

I'm an email marketing strategist, a big fan of The Futur, and VERY interested in
the position. And I may or may not have telepathically detected you're in need of
some serious writing talent.

Experience

- Copywriter for 5+ years, I’ve written letters, ads, articles, emails, and scripts
that've driven over $2M in sales for companies & personal brands.

- Full-time freelancer focused on building email marketing systems for business

owners, artists, and other creators.

Why The Futur?

- I'm a hybrid personality with both artistic and entrepreneurial impulses.

- A big part of my purpose is helping creatives find meaning, build confidence in

their artistic calling, and create a profitable business around it. In that regard, I see
The Futur as a great fit for me.

- I write about these themes in my spare time. Here's a link to an article I wrote on
finding your passion. I also created all designs you see in the article.

Campaign Story
- One of my clients is a popular YouTuber with 25,000 email subs on a largely
inactive email list. I revised all the copy across his offers, revamped the list, and
launched a series of email promos that generated $15,000+ in extra revenue
within 45 days while increasing the conversion rate on his flagship product by
300%.

Details

- Link to Email Portfolio

- Monthly Rate: Dependent on scope of work ;)
- Availability: May/June, ALSO dependent on scope of work

Let me know if you'd like to chat.

Alastair Pitts
Odyssey Consulting
odysseyconsulting.ca
LinkedIn

PS there's a typo in the first bullet point on the first email in your welcome series.

Two commas instead of one: "attracting your dream clients,, networking online,
pricing..."

DEBRIEF:

I didn’t have to run any followup on this one. I heard back about a week later:
It was a big hit with the marketing head, and got noticed by the COO: “We have to
check out this guy.”

Some notes:

- It's about a 500 word email. You don’t always need to go short if you have a good
angle and can maintain attention

- I knew they used Drip for their email platform. Littering in little easter eggs that
signal you did your research can help boost their perception of you, maybe even
subconsciously (specific information)

- the typo PS at the end adds just a little bit of extra intent, and demonstrates
attention to detail (finishing touch)

- I significantly cut down the second half to make it as concise and hard hitting as
possible. I knew I’d probably done a good job of getting a smile and curiosity, but I
needed to back it up with substance

- It took about an hour or two total to craft this. A lot of people will shy away from
that kind of effort for one lead (which is why their cold emails don’t get results)

- There’s some luck involved here: right place, right time. Sent it to someone with
the type of personality to appreciate and enjoy this type of outreach.

But ultimately the most important thing going on in all this is SHOW, DON’T
TELL. I’m trying to get paid to send emails that get attention, keep it, and sell
something. So my outreach does exactly that.

I lean into creativity because that’s one of my strengths.

But if you’re a different kind of operator, with a different type of personality (more
analytical, more data driven, more concise… whatever) you can play this type of
outreach up or down.

Maybe yours is a little less eccentric, but you’re still doing a few things to stand
out.

You’re still SHOWING. NOT TELLING.

The other thing here… it was safe to assume there were lots of fairly generic
applications and pitches being sent in. Email copywriting has a big glut of beginner
level people that don’t have much sales experience, and frankly aren’t that good
at their craft. So individuality and creativity in this sales context has more ROI than
another type of role/niche/context.

Of course, I then had to hop on a call, handle pricing, scope of work, blah blah
blah. So all the standard sales process stuff came into play. But it worked out
nicely.

At one point I even mentioned it to Chris on Twitter, and got his seal of approval
directly. (I mention that to remind you: good cold emails can be used as marketing
assets and credibility boosters in other ways. This post got me leads and followers)
 BONUS RESOURCE #2

My “Sniper” Cold Outreach Strategy I used to book

hundreds of C-level meetings at large companies
(500M+ in annual rev)”

Pull up a seat by the fire my friend, and let me regale you with tales from the
realm of big boy lead gen…
Working on these created a lot of great stories. Some of the most stressful and fun
times of my life.

If you're in biz dev, copy, ever feel like you'll need to connect with someone hard
to reach, or just want to see what kind of drudgery sales bros have to put
themselves through…read on.

The primary strategy outlined here is difficult, time-consuming, and painstaking.

But it works. And a lot of it was pioneered by my sales exec (who taught me most
of my sales foundation).

This got us calls with people like:

CEO of Shopify (yes, Tobi)

Ex-CEO of Blackberry (Jim Balsillie)
CEO, Sony Interactive Entertainment US + Chairman, SIE Worldwide Studios
CEO Chief of Staff, Citibank
EVP, Lockheed Martin Space
EVP, Wells Fargo
President, Bank of Montreal
Co-CEO of CCB, JPMorgan
CFO, TD Bank US
EVP, RBC
President, USAA
President, BMO
CFO, Loblaw
President, Cardinal Health
President, Staples
CTO and SVP Innovation, 3M
CEO, Laurentian Bank
CIO, Canada Goose
CTO, Microsoft Canada
Chief Investment Officer, OTPP
Global Chief Risk Officer, Manulife Financial
COO, Air Canada
CSCO, Amgen
SVP, US Bank
SVP, FedEx Ground

And a S**TLOAD more I can’t remember.

As you can see we hit A LOT of different roles and verticals.

The offer was a productized consulting service, generally 250-500K USD a pop. 4-8
week engagement.

This strategy relies heavily on direct mail. You’re sending letters to executive
offices with handwritten waybills.

Let’s dive into the details…

Trigger-Based Letter Campaigns for ‘Complex’ Enterprise Sales

LIST BUILDING

We ran small campaigns. 10-50 leads per. Financial Services, CPG, Pharma,
Healthcare, Airlines, Tech…we used this strategy across all of them. Slightly better
performance in some verticals, but it generally performed at a bare minimum
baseline of 10% conversion.

Some campaigns converted at 20-30%. I even had a couple do 50%+ (but these
were often no more than 5-10 leads in a campaign)

Some sales gurus will tell you to focus on lower positions (VP, Director, etc) and
then work your way up. They’ll say this is better because you can gather more
intel about an account, or because execs delegate vendor/budget decisions to
their direct reports. Not always the case imo.

The reality is getting access to C-level decision-makers often speeds up the sales
cycle. VP’s, Directors, etc. are often clueless and a waste of your time. They'll take
the meeting to feel important.

You will want to clean your data. We had ZoomInfo. Specifically, you want to make
sure you verify the corporate HQ address, and find out where different execs are
located. This is important for later.

COPY

You will need to invest the time to find good hooks.

Probably the most important part.

The strat CAN compensate for weak hooks (will show examples), but if you can't
demonstrate your competence, your understanding of their business, and your
understanding of the relevant challenge faced…within a few lines of copy…you’re
usually shit out of luck.

There is no room for error and you need to sweat every single element.

Seeking Alpha analyst deep dives, earnings call transcripts, old search results
buried in the 12th page of google search results, shitty corporate podcasts with 12
listens ... .there can be gold down those rabbit holes.

Needless to say everything was personalized. But none of the “loved your blog
post!” BS. You need specific personalization around specific and current business
challenges being experienced DIRECTLY by the executive.

“I understand there are some issues related to the OEM divestiture in China”

“I understand there are now multiple initiatives you now need to drive across the
enterprise”

Blah blah

One funny exception: to get the Sony/Playstation meeting I talked about how
“your competitors are opting to prioritize microtransactions at the expense of high
quality single player experiences, and I believe my company can help you
capitalize on that advantage” or something like that.

Totally made up based on my gaming experience lol.

The point is that executives speak a strange corporate language and part of the
job was learning it. The best copy here will be swiped from the mouths of other
executives.

We would get subscriptions of business sections of papers, find articles discussing

specific companies and execs, then cut those sections out and attach them to the
letter with a paperclip.

PREP

We used UPS for most of our mailing. Company letterhead (firm paper, practically
like cardboard. Stood out than standard 8x11 printer paper), signed.

Handwritten waybills (ATTN: First Name, etc.). We ran small campaigns. 10-50
leads.

RESULTS

On average these would convert to meetings at about 20%. Some 30%. You can do
the math.

This strategy helped us become the only SDR-AE team to consistently hit and
exceed quota over 2 years and into COVID shitstorms.

Everyone else was constantly treading water.

I once had a CEO of a billion-dollar financial services org tell me that he received
over 3000+ pieces of physical mail per year, and mine was one of THREE he
responded to.

That is 0.001% results.

These people get 10,000 cold emails PER DAY. 300+ cold calls PER DAY.

I feel pretty confident in saying we ran the most successful enterprise lead
generation operation in North America.
SOME HIGHLIGHTS:

We beefed up this strat to get a phone call with Tobi Lutke. (pictures down below)

3d Printed an icosahedron in Shopify green, stuffed it with systems thinking books

(he’s a big fan), and put the letter on top.

He called it “the most thoughtful thing I’ve ever received unsolicited”

(Deal didn't close though lol…oh well)

Another one:

We had no tangible business hook for Michael Corbat at Citigroup, but wanted to
take a shot anyway. (picture down below)

He’s a big fly fishing guy, so we ordered some hooks. The letter never made it past
the security desk in the NYC office (probably because of the metal)...but we got
him to look at it.

He liked it, thought it was creative, but asked us to expand on the actual business
rationale for why we wanted the meeting (which we hadn’t really flushed out)

Gotta do the things most salespeople won’t if you want to be in the top 1%.

Every so often we’d get flack from our middle marketing managers, who wanted
us to up the volume and focus on more generic email blasts.

But then we’d walk into the quarterly reviews, drop 20-30% conversion rates on
the slide deck and force them to pipe down for another 3 months.

The biggest weakness here is scale. Never really figured out a way to get past that.
If you combined this with larger email campaigns, you’d probably have a great
barbell strat.
Automated physical mail services like HandyWrytten worked somewhat. But not
really.

I’d recommend some sort of barbell strategy where you’re running larger email
campaigns, then using this to chase whales.
 BONUS RESOURCE #3

My “OG Classic” Email Template

This is a barebones, no nonsense cold outreach template. It’s formal, and more
suitable for a B2B context. You can modify it any way you like, add humor,
personalization, etc, but it serves as a good foundation for any kind of sales
communication.

SUBJ: NAME: quick note for you

NAME,

I understand _________.
I believe my company can help __________.

Past clients include _______.

OR
We just helped COMPETITOR/COMPARABLE achieve ________. Confident I can do
the same for ____.

I’d like 15 minutes on the phone to explain how.

Please let me know if that works for you.

Alastair

BONUS RESOURCE #4

Replying To Replies

So you’ve got a reply. You’ve spent all that time on an email and it worked…

Now what?

I can’t give super specific advice because every context is different. But what you
definitely don’t want to do is descend into a 1000+ word reply with 12 paragraphs.
It’s kinda like a first date with someone you really like. If you’ve gotten their
number, gotten them to agree to a date…

Your main job is to NOT MESS IT UP.

So keep your reply as short and sincere as possible. Just focus on securing the
call, or whatever the next step is (usually a call).
Sometimes you might have an additional 1-2 email exchanges before agreeing to a
call, depending on the context. In this case, they might be the ones to prompt you
with options, as in this example:

Send a few good options:

You want to make yourself available, without seeming too desperate.

Once the call is booked, sending a reminder within 24 hours is usually wise. And
maybe you drop a small hint at something that adds a tiny bit of curiosity
(optional though):

BONUS RESOURCE #5

Upwork Sniping and Sales Call Strategy

Freelance Job Platforms like Upwork can be worthwhile. But if you don’t want to
invest the time to build up your reputation and work history there, you do have
some workarounds.

A decent percentage of job postings will include personal details about the hirer.
The name of the hirer/founder, name of the company, location
(city/state/country), stuff like that. Check the job posting and their job history with
other freelancers. You can become a detective sniper and cross-reference this
information with internet/linkedin searches, and find the client off-platform. Then,
you use the tactics in this guide to send them a cold email. If you still want to use
the platform, you can also send a copy of your application via email. This helps
you stand out.

I did this starting out years ago, and it worked well to get me those first few clients
and sales calls (including one long-term client that made me US$30K+ in earnings)

Sales Call Strategy:

I’m not going to go into full, comprehensive detail on running a sales call. That’s a
bit too much value to give away here.
What I will say is that an ideal sales call looks like this:

● The prospect is talking more than you

● You are asking intelligent questions at the right time, to get them talking

● When they’re talking, they’re sharing specific problems and aspects of their
business. You should listen, and be helpful without giving away your value.

● You’re not being overly salesy, or relying on a script. You’re just having a
transparent conversation about them, their problems, their needs, and your
suitability for solving those things. But again, don’t give away freebies.

● You should be taking notes and capturing important details in some way

IMPORTANT: After the call, you are going to go away and prepare an email to
send them. It should contain the following:

● You state that “based on our conversation, here’s what I understand your
challenges are,” then use their own language as much as possible to
describe those problems in a few bullet points.

● Then share how you can help in the form of a basic proposal (also using
bullet points): “Based on this, here’s how I can help:”
○ List out what your key deliverables would be, timeline, price, and any
other relevant details.
○ Maybe you want to include some relevant links to samples below this
(especially if they asked for some). Then, ask them to please let you
know if they’d like to move forward, or if they have any questions.

Lastly, you make it clear they can say no. Make it LOW PRESSURE. This is a simple,
effective, post-sales-call framework that works.

You can use emails structured like this throughout any client engagement. And if
you communicate well, it’s often preferred to fancy decks and other materials. Just
communicate clearly, build an honest relationship, be honest about risks, trade
offs, and outcome probabilities… and you’ll be surprised how well people
respond.

I know how uncertain things can feel in new situations like this, so I hope this is
helpful (I know it is, tbh), and I hope you appreciate the multiple forms of insight
and value contained within this product (I’ve said too much already!). Please keep
me posted on your progress.

I read every email I receive.

Happy hunting.