Selling to People Who Want to Buy

A common assumption about commerce is that selling is inherently adversarial: the seller tries to convince the buyer to spend as much money as possible, and the buyer resents the interaction. In practice, many people are actively happy to spend money on something that solves a real problem. A $27 ebook about choosing a shade of white paint sounds absurd until you are facing that decision while spending thousands on a paint job. In that context, the ebook is a great investment, and the buyer is grateful for it.

This dynamic applies to technical products too. There are plenty of programmers happy to pay for clear, short, friendly explanations of concepts they need for their jobs. When you sell to people who are buying based on the value they get, the relationship feels far less like a contest.

Email Is Not Inherently Bad

A related belief is that sending business email is inherently bad, and that all marketing email is unwanted. That is not universally true. People subscribe to newsletters for brands they like because they genuinely want news about products and sales. Marketing email can even be genuinely useful.

The key shift is understanding that marketing is not about describing your product to an audience. Marketing, at least for many businesses, is about building trust by helping people. Instead of periodically sending "here's a new product, here's why it's good," the most effective approach can be a regular email that simply provides something helpful—say, a weekly programming comic. People love receiving it, and when you do announce a new product to that same list, people buy it.

Let People Filter Themselves In

It is tempting to think you have to trick people into joining your email list. A common pattern is signing up for a free service and then getting deluged with upgrade pitches. But if your list is genuinely helpful, and you clearly describe who it's for—including a link to the archive so people can preview content—then a lot of people will happily sign up on their own.

When you clearly communicate who the list helps, people can filter themselves in. The only people on the list are the ones who are happy to be there. This avoids sending unwanted email entirely.

This lesson can be learned the hard way. Sending a "you might like my other product" email to everyone who has ever bought anything from you will eventually generate an angry reply along the lines of "why are you emailing me, I just bought that one thing." The right response is to agree with that sentiment and be more careful about what kinds of emails people are opting into.

Clarity Prevents Disappointment

When someone is dissatisfied with a purchase, it does not always mean the product is bad. It often means their expectations were not met. If you communicate clearly and accurately what problems a product solves, who it is for, and how it works, people are much more likely to be delighted.

Concretely, a refund request might come from someone who expected more depth on a particular topic, like sed, and was disappointed to find only one page. The fix is to make the table of contents easy to find, so readers can see exactly what is covered before they buy.

You Do Not Have to Write New Emails Every Week

A common failure mode for starting a mailing list is producing two emails and then giving up. This often stems from the assumption that a weekly or biweekly list requires new content on that cadence. Some people do work that way, but there is a lighter alternative.

Instead of generating new content each week, you can compile a list of your best existing articles or comics. When someone subscribes, you send them one item from that list per week. Most people have not read your best material, so this is often more helpful to them than a brand new article. And you do not need to write anything new for months. This is sometimes called a drip campaign, though tools for it matter less than the content itself.

Unsubscribes and Analytics Are Not Catastrophes

Watching people unsubscribe after an announcement feels bad, even when it is only 0.3% of the list. But people subscribe liberally and unsubscribe when their interest fades. A small percentage unsubscribing is just not a big deal.

Similarly, obsessing over open rates and running A/B tests is rarely productive. Rather than wondering why an open rate dropped from 47% to 43%, it is more useful to define a few specific business questions, like whether people are reaching a page from external links or only from your own, and track those roughly over time.

In practice, the only tracking that proves useful is using a discount code for a new product and noting whether the sale came from the mailing list. The time is better spent writing more helpful things.

Remember There Are People on the Other Side

Emailing thousands of people can feel anonymous, but there are individuals on the other end. A useful mental model is to write to a friendly person you met at a conference who likes your work—not a best friend, but someone who knows your material and is interested in what you have to say.

It also helps to remind people why they are receiving an email, especially after a long silence. "You signed up for announcements, here's one" prevents the list from going "cold," where subscribers have forgotten they are on it.

There Is More Than One Way to Do It

Email marketing is not a monolithic activity. When you start, it is easy to believe it is a terrible, awful thing that requires tricking people. But it is possible to do it transparently, mostly sending helpful emails that people actually want. The key realization is that you have choices about how to do it. If you do not like how someone else runs their list, you can make different choices for your own.