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How an Email Newsletter Publisher Built an Audience of 223,991 Subscribers
16th February 2015 • The Digital Entrepreneur • Rainmaker Digital LLC
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Brian and I have been talking about his new email newsletter lately, and I thought it’d be interesting to have a similar conversation with someone in a completely different topical market.

It’s about one person writing and curating a topic he knows and cares about, building a massive email audience over a period of four years, then turning all that work into a sustainable business.

And hang in there, even if you have no interest in (or understanding of) programming, Javascript, Ruby, or HTML5, you’ll be able to apply the lessons of this episode to your own business …

In this 39-minute episode Peter Cooper and I discuss:

  • How this programmer became a major content publisher
  • Why he switched from blogging to email newsletters
  • How he promoted his newsletters in the early days
  • What he learned from one of the world’s best Tetris players
  • Where the majority of Cooper Press’ revenue comes from
  • The only social network that really works (for him)
  • His approach to opt-in conversion optimization
  • His best two pieces of advice for starting a curated email newsletter

Listen to The Digital Entrepreneur below ...

The Show Notes

The Transcript

How an Email Newsletter Publisher Built an Audience of 223,991 Subscribers

Robert Bruce: Peter Cooper of Cooper Press, thanks for coming on Rainmaker.FM. Before we get into the business of your curated email newsletter, which is really the thing I want to focus on today, more than anything, tell me a bit about your origin story as an entrepreneur, publisher and programmer.

Peter Cooper: Man, I hate the word entrepreneur but I’ll go with it.

I guess I had, what would have been in the 80s, a typical male geek upbringing. Unfortunately it did tend to be mostly a male thing at the time. The people I knew had people in their family who had computers and passed them down and I was playing with technology and stuff like that. A great scene in our days. Although it’s a lot more open than it used to be.

So I grew up in the 80s with all the different computers that were around. Working out how to play with them and program them and stuff like that because my parents wouldn’t allow me to have an Nintendo or anything like that. I never had any of that kind of stuff. It was all just normal computers that I was playing with. This was all when I was a teenager.

I got into doing some demo coding and it was just the normal progression, I guess, for someone who was into programming at a young age.

I then got to a point where I was deciding what to do with life and decided I wanted to become a lawyer. A very kind of interesting profession but it didn’t quite work out. I was going to go to college and start training in that side of things but a really good job opportunity came up. It was around the time of the whole new media scene in London, so I took a job there briefly and went on to do some web design/web development related jobs with people. This was somewhere around 1999.

It didn’t work out amazingly well, so I ended up going self-employed because I liked it. It kind of bombed a bit during the dotcom bust era because I was doing work for companies like Internet.com and various companies that have now gone out of business. Actually they went out of business at the time because it was that kind of era.

In the background I was still coding and stumbled across a few different things. The first one being Ruby on Rails in 2004, which I immediately started to use and got on with it really well. I became interested in doing web development again, and at the same time RSS because I’d been into blogging for a long, long time. Even before the term existed, I was doing an online diary and stuff. So I was very interested in doing stuff with RSS and I built a service called RSS Digest, which became Free Digest.

It allowed you to reprocess and repackage RSS feeds in various ways. I ran that for a few years and then sold it. This gave me a runway to mess around and do what I wanted for a short period of time. It wasn’t “Eff-you money” as they call it but it was enough to just think, “What do I want to do?”

So I started noodling around with writing about Ruby and doing some publishing stuff because I realized when I was younger, I had quite an interest in publishing, so I thought I would see if I could make a job of it. And that seems to be what’s happened.

It went from running a blog and the most successful one being Ruby Inside, which was basically the most popular Ruby on Rails related blog between 2007 and 2012. There was various other things along those lines but from that I ran Ruby Weekly. And then from Ruby Weekly came all the other different newsletters that I now have. So I am now principally doing email.

Robert Bruce: So you came from a programming background, which was your interest and you developed those skills. For those listening, I’ll do a little bit of an introduction. Cooper Press is a curated email newsletter. I can’t think of anything better than the word “network” to describe it. It’s a network of email newsletters. Is that fair?

Peter Cooper: Yep.

How This Programmer Became a Major Content Publisher

Robert Bruce: Your focus is still on technical, programming type languages and the news, and you are curating things around that. But this is really going to be interesting for our audience and the shift I would like to make now is, you are this accomplished programmer and you are also an accomplished writer and publisher.

I heard you tell a story a while ago about where the idea for publishing newsletters came from, maybe not that specific to start, but publishing in general. You don’t see a lot of crossover from programmer type folks into wholesale publishing, so how did that happen?

Peter Cooper: It was by accident really. I’ve always been a big believer in blogging and the whole idea of using blogging to build up a business, build up your profile and stuff like that. But as I got into doing it, I realized that a lot of it came from when I was a kid.

When I learned stuff about programming, math or whatever, I would often write my own guide to it and I don’t know why. It was an inbuilt thing that I just did and enjoyed doing.

Robert Bruce: You wanted to write a book?

Peter Cooper: Well exactly, yeah. Not proper books as such but that same idea of, “I’ve got this knowledge. I need to get it down in some way and potentially it could be useful to other people.”

I realized I had a habit of always doing this through life in various different ways. In the mid 90s, I did run Basic, like QBasic type programming and I ran a fanzine for basic programming on a news group, for about 10 or 11 issues. It came out monthly. It had code in it and people’s emails they would send in and stuff like that.

I remembered how all the stuff I had done was so natural to me and I just got to this point in my life where I thought, “Well hang on. I should probably just start doing the things that are still natural to me, rather than fighting against stuff.” Even though I had always written software for a living and didn’t mind do it, I didn’t quite enjoy doing it for other people.

So I thought, “Let me do something that I do enjoy doing for other people,” which is the publishing side of stuff. I just connected those dots in my head and that’s what made me get into this. It wasn’t a big plan of “How can I make some money?” It was, “Yeah, I know I am inherently good at doing stuff like this. Let’s just give it a go.”

Robert Bruce: And folks can find you at
cooperpress.com. At the current count, I think you’ve got eight different newsletters. Is that right?

Peter Cooper: There are more. It’s just that site is hideously bad. I’m like the builder with the ramshackle house.

Robert Bruce: You know, we can talk about fixing that up for you but that will be for later.

Peter Cooper: Exactly. The best way is to go to a site like JavaScript Weekly and then at the bottom, we automatically add links to all the different things that are pre-populated there.

Robert Bruce: Yeah. I want to talk about JavaScript Weekly just a little bit later but to give people an idea of what you are doing here with the multiple curated email newsletters, which are focused in and around programming type topics, how many email subscribers in total do Cooper Press serve right now?

Peter Cooper: As of this very second, 223,991. Let’s just round it up to 225,000.

Robert Bruce: That is very impressive. Does one, two or three stand out way more than others?

Peter Cooper: Yes.

Robert Bruce: Or are they pretty fairly evenly distributed?

Peter Cooper: No. It’s quite large gaps between some of them. We have quite a few smaller ones, which are more recent ones and we are trying to build up. But in terms of the really big established ones, it’s pretty much Ruby Weekly, which was our first one but it’s now the third largest. The first two are JavaScript Weekly and HTML5 Weekly.

JavaScript Weekly eclipses the others but HTML5 Weekly is pretty big as well. JavaScript Weekly is about 75,000, HTML5 Weekly is like 55,000 and then Ruby Weekly is like 32,000.

Robert Bruce: Crap.

Peter Cooper: And then it drops off quite a bit. Then it goes into Node and various other topics, which are sort of coming up behind.

Robert Bruce: How long have you been doing it?

Peter Cooper: I believe the first issue of the first newsletter, which was Review Weekly, would have been in very late 2010. So just over four years. It was very amateur for quite some time. It didn’t make any money for the first year or whatever. It didn’t really intend to. It was more of an addition to the blogging stuff that I was doing but now the blogs have pretty much died.

Robert Bruce: Interesting.

Peter Cooper: This has now become the main thing.

How He Promoted His Newsletters in The Early Days

Robert Bruce: So you’ve been doing this a long time and we’ll get into the details of what you do every week for each newsletter a little bit later, but tell me about the early days of publishing that first newsletter and as the other ones came along.

How do you go about promoting your stuff? Did you have a built in audience? Obviously you have been publishing and doing things online for quite a while. How did you go about promoting these email newsletters?

Peter Cooper: In the early days, it was pretty much down to the fact that I already had the Ruby Inside blog, which was very important as a way to launch. It had like 30,000 RSS subscribers at the time, which at the time I thought was absolutely huge but now looking back, it’s funny how things go. So I had that.

I also had a site called Ruby Flow, which I’ve just relaunched in the last couple of days. It’s more of a community kind of blog, where anyone can post stuff.

I’d had these different outlets to the Ruby community anyway, so as soon as I put it out there that I was doing this, within a couple of days I had over 1,000 subscribers straight out of the gate. Just people who were curious. You know, quite a few detractors. People saying, “It’s a bit old fashioned doing email, blah, blah, blah” which you hear less and less now. But in 2010, it wasn’t very trendy to have an email newsletter whatsoever, so it was almost like blogging was in the early 2000s.

Robert Bruce: Is it trendy now?

Peter Cooper: I think it is.

Robert Bruce: I think you’re right.

Peter Cooper: Because every time I go to a company, do a podcast or whatever, everybody is trying to get me sign up for email. I’m almost kind of getting sick of it. It’s very funny to be in this business and seeing that happen.

Robert Bruce: You had a little head start with about 1,000 immediate sign ups but it sounds like after that point, it was really natural growth.

We’ve talked a lot about the email forward being the early social sharing. Did you see a lot of organic growth then from forwarding, from people talking about you online? Obviously, the programming community is a rabid community in terms of interests in the topic. People are close knit and it probably had a lot to do with that. But was it mostly an organic growth from that first point?

Peter Cooper: Almost entirely organic growth. Just a couple of things that I would say that have been big influences is getting mentions by people that are very prolific or well known within the scene. In Ruby Weekly’s case, early on we got a mention from Chris Wanstrath of Github. He mentioned that he liked it and so on, and I believe Paul Irish also mentioned JavaScript Weekly when it was very new. Those types of referrals are worth a lot. You get a certain amount of boost off of those.

The other thing that really helped is, quite a few people seemed to build those lists of things you should read, or things you should subscribe to in certain topic areas and we seemed to turn up on those lists quite often.

Those lists become really popular on things like Reddit and Hacker News. We seemed to get a ton of people coming through. When we have queried subscribers on how they found us, often these types of posts have come up. People said, “Oh, I found this post of useful resources and you were just included in it.” So that’s become important as well.

Robert Bruce: Yeah and I’ve heard you talk about, or write about, elements of conversion on the one page sites as well, that we’ll talk about a little bit later but before we do that, Rainmaker.FM is brought to you by the Rainmaker Platform. If you are looking to easily build a powerful sales and marketing website that drives your online business, head over to RainmakerPlatform.com right now, and sign up for a free 14-day trial to see if it might be a fit for you.

Rainmaker handles all the technical elements of good, online business practices for you. Design, content, traffic and conversion and she does it all under one roof. So get over to RainmakerPlatform.com now and get back to building your online business in 2015.

Why He Switched From Blogging to Email Newsletters

Robert Bruce: Okay Peter, we’ve touched on the history of your email newsletter empire and you had mentioned blogging before that, and doing more kind of traditional content websites before that, so why did you shift to this email curation model? Why did you not keep publishing articles on a blog? What was the thought process there?

Peter Cooper: A couple of things. One is we used to have reasonable success with doing roundups of other people’s content but it was never like a really huge thing on the blogs. It tended to be original content that worked a lot better on the blog, rather than leaking out elsewhere, which is why we ended up creating the Ruby Flow site as a way that other people could promote their own stuff. But what I found with email, once I got going with it, because it was just an experiment, it was just a case of, “Someone else is going to do this. I better do it first.”

I discovered that the engagement was very different to the sort of engagement you get on the web. I’d become quite familiar with how readers who found certain things interesting on the web, found different things interesting when it came to email. And just the way they engaged with it would be different and the way we could track the engagement would be different. We knew how many of our subscribers actually came along and actually did something with an item, rather than counting page views and stuff like that.

I really liked the engagement model and obviously the other tempting thing, after a certain period time had passed, and I decided to make it a lot more into a business, is the advertising situation. And certainly in my case, it’s very different in email, as opposed to the web. In...

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