Chapter 01A cold email I almost deleted

The method in this book found me through the thing it fixes. A stranger sent me a cold email. I was one keystroke from deleting it. I didn't, and that one reply rearranged how I sell, how I raise and how I spend most of my days.

I'll tell it the way I told it on a call in March. That's the oldest recording I have of it, before I'd polished it from saying it a few hundred times:

So Charles changed my life, you could say. He essentially cold emailed me one day. And normally I delete stuff like that, obviously, right. Like, I'm super busy. But something he said in his email caught my attention.

That's the whole hinge. A guy I'd never met, an inbox full of noise, and one line that made me stop.

Twenty years of trying everything

To see why that line landed, you need to know what I'd been doing before it.

I started my career selling robots. Eight years at a robotics company in Canada, selling into the top engineering labs in the world. Nobody called it outbound back then. I called it work, and the work looked like this:

my process would be, you know, get to work, grab a coffee, you, like, research these professors, try and find what their, you know, researching and then look at my, like, menu of a hundred, you know, robot things and then be like, oh, dude, you need this

Coffee, research, a menu of a hundred products, and a guess about which one this professor might want. On a good day:

I could probably crank out five or ten those customized cold emails a day and convert maybe one out of 20 or one out of 30. And that was the game.

That was the game. A handful of emails written by hand, with one hit in twenty or thirty if the week went well. Then I moved to India, fell down the bitcoin rabbit hole and started India's first bitcoin exchange. The tools changed and the game stayed the same. I ran conferences and bought ads, and I went live on every platform that would have me. Every time I sat down with a spreadsheet, the numbers told me the same story:

And I had by then tried everything under the sun, right? Like, I'm an entrepreneur, sales, didn't do marketing, Google ads, Facebook conferences. I've personally hosted, like, hundreds of conferences, but all of them, you do the math on it, and it's like, it's hard to justify, like, the dollar spent.

Hundreds of conferences. Think about what goes into one. The venue, the badges, the speakers, the dinners. Then you count the conversations that turned into something. I did that math more times than I want to admit, and it never came out clean.

So I had a dream, and it was a small one. Forget the yacht and the exit. What I wanted was a calendar:

My dream was always wake up on a Monday morning and see my calendar full

Full of the right people. Investors, partners, buyers, people I wanted to learn from. Lined up one after another, without me spending the weekend at a booth begging for business cards. When I describe that dream to founders now, I still list everything I wanted to skip:

I didn't want to do all the hard work, like the. The conferences and the. Google Ads and the this and the networking and the parties. Like, I just wanted to click a button

Click a button and see the week fill up. Every founder I talk to has some version of that wish. Most of them have also learned, the hard way, that the button they keep pressing is wired to the wrong machine. More events, more ads, more parties. I pressed those buttons for two decades, and none of them filled the calendar with the people I wanted.

Why I was ready to hit delete

Here's the irony. I knew cold email. I'd done it by hand for years, and I knew its ceiling better than most:

How do you send 1,000 emails a day? Like 10,000 emails a day? I could do five. I could do 10, maybe if I just use my email. But if you do more than that, you get marked as spam.

That was my whole mental model of cold email. A craft for people with time, and a trap for anyone in a hurry. So when a stranger's pitch showed up in my inbox, the reflex was automatic. Delete, next.

What stopped me? I wish I could tell you the sentence. On one call this year I finally admitted the truth:

But something Charles said in the email I forget what it was but caught my attention he got me on a call

I forget what it was. My business runs on cold email, and the one cold email that changed my life is the one I can't quote. I've made peace with that, because what I do remember is the call.

The call

Charles didn't walk me through a product. He told me his story. He'd run call centers. He'd tried every channel there is. Then he said my name and made a claim I didn't expect:

out of everything I've done, the only thing that I can point to and I can reliably point to the ROI is cold email.

I'm an engineer. I like claims I can test. He wasn't selling me a feeling. He was telling me where the return showed up when you followed the money all the way through. My own spreadsheets had been saying the opposite about everything else I'd tried, so I leaned in.

On later calls I describe that first conversation as an argument from first principles. He took cold email apart and asked me to look at what was left. My reaction was the same one I'd want from any smart buyer:

And I was like, oh, it's a bold claim. I'm like, let's put it to the test.

I'd been burned by every channel that promised me a full calendar. So I did what any skeptic with a few companies should do. I ran the experiment.

So I was like, okay, fine, I'll give it a try. I ended up trying it on my own company. I was looking for remittance Partnerships, and I landed a whole bunch of them. Then I tried it on a few other money companies. It worked.

Three words at the end. It worked. I've said a lot of things on calls over the years, and that's one of the shortest. It didn't need more.

From customer to co-founder

What happened next came in three steps.

First, I was a customer like anyone else, and I used the system on my own businesses.

Second, I couldn't shut up about it. Every founder I met who was stuck on growth, I sent to Charles. In January, on the oldest recording I have of this part of the story, I put the number this way:

I've probably brought him 40 to maybe 50 companies just from my network, so I'm a big believer in his system.

Third, at some point he looked at all those referrals and made the obvious move. He made me a co-founder. The way I tell it now, he said something close to this: you keep bringing me deals, why don't you come on board?

And the dream? On that same call in January I said it out loud:

And it was only after I met Charles was able to achieve that.

That full Monday calendar had dodged me for twenty years of conferences and ads and booths, and it showed up through a channel I'd written off. A few months later, on another call, I said it even more bluntly:

I've never had anything until I met Charles.

The part I didn't see yet

If the story stopped there, this would be a book about cold email. It goes somewhere else, and this is where it turns.

Once I was inside the business, looking at the numbers across campaign after campaign, I saw the problem I'd always suspected:

So I joined him, and I noticed pretty quickly that it is an uphill battle, right? Doing outreach with cold emails sales is really tough, but there was one piece of it that really stood out, which was whenever we. Ran campaigns where we invited people to our podcast or our customers' podcast, it would break all the rules.

Cold email that asks is hard. Cold email that gives breaks the rules. That one observation is the seed of every chapter that follows. The show grew out of it, and so did the debrief. So did my habit of saying "spotlight" on business calls more than almost any other word.

Look back at my own story with that lens. A stranger got through my filter, and to this day I can't recall the pitch. What I can recall is the story he told me on the call, the claim he made, and the fact that he let me test it on my own company before I committed to anything. He gave me a reason to listen and a way to prove him wrong. Then he let the result do the selling.

I didn't have the words for it then. I do now. The best outreach carries something for the other person, and the relationship starts there. An ask dressed up nicely is still an ask, and people can smell it from the subject line.

Try this week

Go to your inbox and find the last cold email you nearly deleted but answered. Skip friends and warm intros. You're looking for a true stranger who got through.

If you can't find one in your inbox, search your memory. A message on LinkedIn, a DM, a letter. Most of us have one or two in a whole career.

Write down three things about it:

1. What made you stop. Be honest. Was it the subject line, a name you recognized, a compliment, a question, an offer? If you've forgotten, like I did, write down how it felt to read it. 2. What it asked of you. A call, money, a favor, nothing at all? 3. What happened after. Did you buy, partner, refer, become friends? Or did it go nowhere?

Then do the same for five cold emails you deleted this month. Same three questions. Don't skim them. Open each one and read it the way the sender hoped you would, top to bottom, and notice the exact moment you decided it wasn't for you. Was it the first line? The second paragraph, where the pitch showed up? The link at the bottom? Mark that spot on each one.

Put the two lists side by side and look at what the one you answered had that the five didn't. In my experience the difference is rarely the writing. It comes down to whether the sender was asking you for something or bringing you something.

Keep that page. You'll use it in the next chapter, when we put your own outreach under the same light.

So here's my question for you. The next time a stranger reads your email, will they reach for delete, or will something in it make them stop?