[jmduke]

The vast majority of commenters are being negative about this essay, and I agree with the negativity, because _automated cold emails_ are awful. (As are sequences, and mail merges.)

However!

_Bespoke cold emails_ are I think, a dying/lost art. I want to give an example of two cold emails that I (manually!) send a few times a month. (I run Buttondown, which is an email SaaS — think similar to Mailchimp, ConvertKit, etc.)

---

The first is to folks who have the following criteria:

1. they hit the front page of HN

2. they have a personal blog that isn't tied to a platform (e.g. they're using jekyll or something similar)

3. they have RSS enabled

4. they do _not_ collect email addresses

The thrust of the email is this:

``` Hi! I'm the founder of Buttondown, a newsletter tool for technical blogs. I'm reaching out because:

1. You just hit HN front page! (Congrats and/or my condolences.) 2. You've got an RSS feed but are not capturing emails.

My proposal: I set you up with a free (for life!) Buttondown account seeded with your blog's RSS feed. All you do is drop in a form tag or an iFrame in your blog and folks can sign up with their email address and get an email whenever you publish something new. I can handle the setup and then hand it off to you for perpetuity.

If this is something you're at all interested in, please let me know! (There's no catch, and this isn't an automated email, so please — I'd love to hear why not, even if the answer is simply "shove off, I don't care about collecting an audience, Twitter and Mastodon are sufficient"). ```

(I tweak the language based on their own voice, mention what in particular I like about their blog, etc.)

---

The second is to folks who fit the following criteria:

1. they're a technical newsletter publishing programming-related content

2. they're using a platform that I know to be particularly expensive relative to me (Mailchimp, ActiveCampaign are the two big culprits here)

``` hi there! I run Buttondown — you may have heard of us, we're used by RELEVANT_CUSTOMER_1 and RELEVANT_CUSTOMER_2. I see you're using OTHER_PLATFORM; is there anything I could do to get you to switch to [us](https://buttondown.com/pricing?count=7500)

(btw, this is a real email, not a marketing campaign. it's still early days for us, so tbh you telling me why you're _not_ interested is just as valuable as getting to call you a customer :) ```

Small sample size for both genres — I've probably sent them a total of ~fifty times — but the response rate is around 80% and conversion rate (though granted for the first genre "conversion" is more of a second-order effect, since I'm offering them a free account!) is ~25%.

I say all of this because, as someone who a priori _hated_ outbound and "sales stuff", I learned that at least for me and my business both the most palatable _and_ most effective method was just being earnest and helpful. It has been the single most useful non-technical skill I've gained over the past few years.

[bhaney]

I love when a marketing campaign email template contains something like "btw, this is a real email, not a marketing campaign"

[AH4oFVbPT4f8]

Much like when a chatbot says, Real person here!

[samwho]

Can confirm. Received the first email here from Justin and it worked on me.

[asynchronous]

See I like this, but because it’s personalized. A human did this intentionally, in a way that does not scale.

The author is advocating for nearly the opposite.

[handfuloflight]

How do you respond to those who call this spam?

[kstrauser]

Oh, it’s absolutely spam, by definition. That said, that’s a wide spectrum. I don’t generally like TV ads, but the State Farm ones with Patrick Maholmes and Andy Reid are funny and I don’t mind them. Kind of the same here: it’s spam, but if there was ever one that’d get a response from me, that would be it.

[handfuloflight]

> Oh, it’s absolutely spam, by definition.

By whose definition? Source?

[kstrauser]

Here’s the FTC’s definition in a presentation to the House (https://www.ftc.gov/sites/default/files/documents/public_sta...):

> Unsolicited commercial email -- "UCE," or "spam," in the online vernacular -- is any commercial electronic mail message sent, often in bulk, to a consumer without the consumer's prior request or consent.

It’s often in bulk, but needn’t be to meet the definition of Unsolicited Commercial Email, aka spam.

[reddalo]

>sent, often in bulk, to a consumer

That's the key. The FTC defines spam as something sent to a consumer; in this case, the receiver is not a consumer but a business.

[kstrauser]

I’ll lay it on the line. In the many years I ran mailservers for a living and for a hobby, I was elbows deep in fighting spam. One of the consistent patterns over the years was that spammers would go to elaborate lengths to explain why their spam wasn’t spam. If it’s unsolicited commercial email, it’s spam.

Again, there’s a wide spectrum from v14gr4 p1ll5 to a legitimate vendor in my job space reaching out to me. They’re not all alike. But if it’s commercial, and unsolicited… it’s still spam.

[jmduke]

I think the definition of spam necessitates some level of bulk sending, and I struggle to consider ~fifty emails over the course of two or three years "bulk".

[MrVandemar]

I'm quite sure you can do all sorts of mental gymnastics to avoid thinking of yourself as a spammer.

Here's my basic criteria for spam:

1. It's unsolicited.

2. It's trying to sell something / exploit people.

In my grading scale I classify you as a spammer. A "bespoke" spammer perhaps, but I still do not want to waste time reading anything you send me, or waste time even clicking "mark as spam", unless I ask for it. You would be stealing my mental CPU cycles (which are few and precious).

[handfuloflight]

> 2. It's trying to sell something / exploit people.

Are these synonymous?

[MrVandemar]

No. I'm drawing a distinction between “I want to sell you something” and “click this link to a website that strongly resembles, but is not, YourBank to transfer all your money to us.”

[8n4vidtmkvmk]

I think / is usually reserved for synonyms. Should just use the word "or" if it's this or that.

[jamesfinlayson]

I remember an old boss launching a product this way - he read the spam law and while I don't remember the specifics, sending an unsolicited email to people whose emails you obtained legitimately was okay if you weren't explicitly selling something (which I think is very open to interpretation).

[handfuloflight]

> was okay if you weren't explicitly selling something.

The CAN-SPAM Act does not forbid explicitly selling something. Rather it requires an opt-out mechanism and identifiers for who the sender is.

[jamesfinlayson]

Yeah okay - obviously varies by country although I think the opt-out mechanism is pretty universal.

[handfuloflight]

So if the same qualitative factors were kept for your outreach, just an increase in the quantitative equation means it's spam? One discrete instance is not spam but the combination of all of them makes the whole spam, when certain thresholds are reached? If so, how do we define those thresholds?

[jmduke]

It's an interesting question! To me, an (or perhaps _the_) obvious threshold is once the emails become automated.

[handfuloflight]

Why does that factor make it spam?

[meiraleal]

Great, you are spamming HN telling a story about how you spam HN