Hello {{First name|Predictable Revenue community}},

Follow up tool update: I had 20 conversations with close founder friends and I’ve come to the conclusion that this thing, while neat, is dead in the water. Enough folks are replicating it with a set of Claude CoWork Skills that it became not worth doing. I’m working on a set of Skills / Automations that can be run from within Claude, stay tuned.

Internal prospecting tool: Made some good progress but it’s not ready for prime time yet. I’ve added an integration to CTD.ai to make it possible to answer the question, “who am I connected to that might be a good potential customer”.

Onto the newsletter…

More than a few years ago I was writing a cold email pitching voltageCRM, my CRM startup that did not work out. I remember staring at the draft thinking it was pretty good. Specific value prop. Clean ask. Calendar link.

I sent it to a list of sales leaders.

Reply rate was about what you'd expect from sending a CRM pitch to a list of sales leaders who already had CRMs. Which is to say, terrible.

The frustrating thing is, I knew the product was useful. I knew, in theory, that some of those people were going to switch CRMs eventually. I just had no idea which ones. So I wrote the same email to all of them, hoped a few were shopping that week, and got humbled.

Looking back, the email was not the problem. The premise was.

I was writing every email as if the reader was actively in the market for a new CRM. They mostly weren't. And no amount of subject line A/B testing was going to change that.

This is the thing I want to talk about today, because almost every founder I work with is making some version of this mistake. They are writing cold emails as if 100% of the list is ready to buy. The math on that is brutal.

There's a paper from John Dawes at the Ehrenberg-Bass Institute, commissioned by LinkedIn's B2B Institute in 2021, that put a number on something most experienced sellers have always felt. He called it the 95:5 rule. The line is, "up to 95% of people or firms are not in the market for many goods and services at any one time."

Dawes is careful about this. He is not saying it is exactly 5%. He is saying it is a heuristic. If your category has a five-year repurchase cycle, you can do the math and get to roughly 20% in-market in a year, which gets you to roughly 5% in any given quarter. The exact number changes by category. The shape of the curve does not.

Roughly 5% of the people on your cold list are actually shopping right now. The other 95% are doing something else.

Sit with that for a minute. If you have a list of 1,000 prospects, about 50 of them are open to a conversation about buying something like what you sell. The other 950 are running their week, hitting their numbers, dealing with whatever just blew up that morning, and not thinking about you at all.

When I write to all 1,000 of them as if they are the 50, I'm being relevant to almost nobody.

The way I think about the journey now is in four rough buckets. None of these have precise percentages, and anyone who tells you they do is selling you something. But the shape is useful.

Just bought. These people locked in a vendor in the last year or two. They are not going to switch unless something breaks. You cannot sell to them today. The job is to be the brand they remember at renewal.

Not aware they have the problem. The biggest slice of your list. They are doing things the old way and it is fine, mostly. They have not yet had the moment where the old way breaks. You cannot sell them solutions because they do not think they have a problem.

Aware, not actively solving. They know the pain exists. They have not prioritized fixing it. Other fires are bigger this quarter. The bar to move them is real but not impossible.

Actively shopping. The 5%. These are the people who will respond to a tight value prop, social proof, and a calendar link. This is who almost every cold email is written for, even though they are the smallest group.

This is the part I got wrong for a long time. I thought I could write one clever email that would do different work for different readers. The shopper would respond, the not-quite-ready people would file the name away, and everyone would walk away with something.

That is not how it works. An email built to close the 5% reads as a pitch to the 95%, and they delete it. An email built to be memorable to the 95% reads as soft and pointless to the 5%, and they delete it too. You cannot serve both audiences with the same message.

The answer is to segment. You carve off the slice of your list that looks like it might be in the 5%, and you write to them like they might be buying. Everyone else, you either wait, or you write a different kind of email entirely.

This is where signals come in.

A signal is anything that lets you infer someone might have shifted from the 95% into the 5%. A new VP of [X] just got hired. A round just closed. A roadmap post just went up that hints at a problem you solve. A senior person just left. A competitor's name just showed up in their job posting.

You do not know for sure that any of these people are shopping. You are inferring. But the inference is enough to carve them off the main list and treat them differently.

For that slice, you write the direct email. You say what you do, who you do it for, what changes when they work with you, and you ask for the meeting. The why-now is the signal itself. That is what makes it feel relevant instead of generic.

For everyone else, the math says don't pitch. The two reasonable plays are to wait until a signal fires, or to send a relationship-building email that does not ask for a meeting at all. Share a useful piece of writing. Ask one genuine question. Comment on something they posted. The goal is not to convert this quarter. It is to be familiar later.

The mistake I made at voltageCRM was treating the whole list like the 5% because I had no way to tell who the 5% actually were. I did not have signals. So I sent the buying-mode email to people who were not in buying mode, and I got the response rate that math predicts.

Before any cold email goes out, I run it through two questions.

Why now. Can I point to something specific that happened in the last 30 days that makes this week the week I'm reaching out? If I cannot point to a URL, the email is going to read as generic, and the reader is going to feel it.

Why them. If this person forwarded my email to their boss, would the boss say "yes, that is exactly your job to fix"? If not, I am writing to the wrong person, and I should multi-thread or start over.

If the why now is real and the why them is real, the email is relevant. Length, subject line, opener, all secondary. If you cannot answer those two questions, you do not have an email yet. You have a draft.

Are you writing to the 5%, or are you blasting the whole list and hoping?

Collin

PS - here comes an ad for my book, I stole the idea from Sahil. It felt like the right thing to add to the end of each newsletter.

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