[Podcast] Pushing Send Episode 22 – Peter Cooper

Peter Cooper

How the founder of an email newsletter network with over 500,000 subscribers built his network, how it’s changed over the past 10 years, and how to cultivate a loyal audience. This is Peter Cooper’s story about Pushing Send.

Peter Cooper is the founder of Cooper Press and the editor of several weekly newsletters, including JavaScript Weekly, and co-host of The JavaScript Show as well as the editor of several popular Ruby Web sites and author of Beginning Ruby.

Key Points From This Episode:

  • Peter saw a need for email-first communication in his niche and he got his start before someone else beat him to it. He pitched it to his current list and it grew from there.
  • Ruby Weekly, Peter’s newsletter started out as a way for him to sell his online courses and he pivoted to include sponsorships as an alternate source of income.
  • Using Facebook’s domino strategy to build a similar group of publications like JavaScript Weekly and others, as well and they all slightly overlap each other.
  • When you need to build something, build from the well of your current audiences and lean on the audience of someone else.
  • Building trust creates a subscriber who will then move on to your different publications.
  • With Peter’s publications, they try to provide justifications for why they have linked to certain things and as to why something is newsworthy or interesting.
  • Decide if you want to have a specific or general personality with your newsletters.
  • Coming up with systems for your business can help you be prepared for the unexpected.

Tweetables:

“At the end of the day, I’m running a business that I want to keep running for 20, 30 years. So there’s going to be a lot of boring time in that. It’s not all going to be fun and sunshine and rainbows.” – @PeterC

“Look at what you’re doing and what’s working, but then think about what those people also do, who they also mingle with, what are the kinds of, of domino effects you can bring into your thing.” – @PeterC

“When I need to build something, I kind of go and drink from that well that I’ve nurtured and made work over time.” – @PeterC

“Software engineering is a space where you do tend to trust people’s opinions more on why they’re sharing news with you perhaps more than just having a fire hose of stuff in your topic space.” – @PeterC

“Email, which originally was less intimate is now actually becoming a more intimate format in this modern kind of 2018 last Renaissance of the email newsletter.” – @PeterC

 

Links Mentioned in Today’s Episode:

Episode Transcript

Peter Cooper:

So you can ask this question to a lot of operators in the space and they’ll be very kind of bombastic and optimistic and say, yeah, we’re going to do X, Y, and Z. And we’re going to have 10 million subscribers next year. And that’s just not me. Like, I, my brain just never works that way. As I said, I seem to luck into things. We always have this way now I’ve always wanted to see like, Oh, where are we going to grow? What am I going to do next? But actually maybe sometimes, you know, I need to slow down and think about, I just need to do the day-to-day work. I need to kind of find the value and the, the energy and the interest in doing that, because that’s what it’s all about. At the end of the day, I’m running a business that I want to keep running for 20, 30 years. So there’s going to be a lot of boring time in that. It’s not all going to be fun and sunshine and rainbows. It’s just how it goes.

Bryan Kelly:

From rasa.io, the free tool for sending smarter and better email newsletters. This is Pushing Send, a show featuring people who sent emails, their subscribers actually want to read. I’m Bryan Kelly, and on today’s show how the founder of an entire network of email newsletters got his start 10 years ago. Here’s Peter Cooper recalling when it all began. So Peter you’ve been publishing multiple email newsletters for 10 years now, but what was the inspiration that got you started?

Peter Cooper:

I can tell you very specifically, actually it’s something I remember quite well. There was a chap called Jason L Baptiste, who did some articles, which did really well on Hacker News. At the time, this was sort of around 2009, 2010, and they were called something along the lines of I’ve got them in front of me, but of course it’s been like, why email is blowing up or why there’s a Renaissance of email newsletters considered even a Renaissance then 10 years ago. And he talked about different email lists, like Help a Reporter Out was one, things like what Groupon were doing and Living Social with their kind of daily deal type things. And he just basically brought together about 20 different businesses that he was seeing in the startup space that were using email as the core of their thing. And that was actually quite a new idea. There weren’t too many companies around the, say the.com era, for example, that were using email as their main play. It was always kind of a backup thing. You know, there were newsletters around 20 years ago, but it was always a bit of a, we’ll just use this to funnel traffic to our site type thing. And he’d noticed there were these email first companies. And I thought, yeah, I kind of see like where this is going and we’ve read or being on the wane and blogging being slightly on the wane. At the time, I had a very popular blog in programming space in the Ruby programming space. And I just thought, if I don’t do this, someone else is going to do it. I kind of almost felt scared that someone else was going to do it. So I just did it. And that’s kind of how a lot of things to come together. So I just had this idea that, well, I could do this weekly I’m already doing blog posts every day, and I sort of did little roundups every week anyway. So I thought, well, I can all able to have that kind of experience into doing it as a weekly newsletter and off I went, it was literally just sign up for MailChimp, put together some simple sample issues just to get a feel for what it is, create a landing page. And off we go. And I proposed it to my existing blog audience base. That was about, I think we had about 40,000 people subscribed to my RSS feed and a couple of thousand signed up pretty quickly actually. And it just went from there.

Bryan Kelly:

Were there any benefits for you immediately when you made that decision? More specifically, what was life like after you flipped the switch and began moving the direction of multiple newsletters?

Peter Cooper:

I could definitely tell the engagement was a lot higher on email. So the main thing that I wanted to use, the first newsletter, which was Ruby Weekly, and it’s still up there, Rubyweekly.com. The first thing I used that for was to promote my own courses I was running each month. So there was also at the same kind of time as I launched it a little bit of a fad, which actually has kind of come back again. Now, again, these things seem to happen in 10 years cycles. There was this kind of fad of doing online courses, especially live kind of interactive ones at the time. And I began doing some of these in the Ruby space and the rail space. And it was one of these sort of things where you could charge $400, have several hours with me on a live session. Then I could have 10 or 20 people or whatever it was. It was about 20 to twenty-five people actually come on the session and off you go. So, you know, that would make a reasonable amount of money and you could run one of those a month and bam, you’ve got your, your income sorted out. So I thought the whole point was, I’d use this list to just promote these all the time, like the goal wasn’t to sell advertising or sponsorships or anything like that. It was just to get people in for these courses. And it worked really well for that, but I discovered I had weaknesses in, you know, I just didn’t want to do the teaching every month. It was kind of soul draining and just didn’t suit my personality. So when people started to reach out and say, well, actually we’re going to kind of get in front of your audience as well. I was like, okay, maybe he has a future in doing this. So in terms of being, you know, a business running the blog was fine, but it kind of had this low growth kind of low ceiling to it. You know, it was never going to be like the next Tech Crunch at the time, you know, where he was charging like tens of thousands of dollars every month for, you know, small, tiny one 25, one 25 JPEG ads in the corner, you know, have kind of this limit to it of several thousand dollars a month, which is fine. But email, it was much more obvious to tie the number of subscribers and the engagement that you’ve got with specific ad rates. So back at that time, 2010, 2011, you could look at companies like Thrillist, for example, would probably be an example of a list that was popular at the time. I guess it’s almost a bit a more fashion-y version of The Hustle, but 10 years ago, and they were kind of boasting that they were selling sponsored emails. This is where you would do an email that was just about the sponsor. It wasn’t like embedded or anything like that. It was just about the sponsor. They were charging like $200 CPM or something. Ridiculous. So when you look at, you know, let’s say they had a hundred thousand subscribers, that’s a serious amount of money for one email. And that kind of business model appealed to me because it was even if you, weren’t going to charge $200 CPM for a sponsored mail, you could charge $50 or $40 CPM for a inclusion in your normal mail. And so that’s what we began to do. It worked and yeah, the rest is history, as they say.

Bryan Kelly:

Well, did you have a master plan or a big strategic vision that you followed?

Peter Cooper:

Things just kind of creep up on me. I’m a little bit naive in many regards as to, I don’t tend to sit down and have a plan and think, right, I want to make X number of dollars in two years time on each do X, Y, and Z to get to that point Germany. I just do something that I’m kind of interested in or obsessed with at that current point. And if it succeeds, then I kind of look back and go, actually hang on. That worked out really well. I should keep doing a bit more of this. I’m just a little bit naive with stuff like that, but you know, things grew and I kind of, I was really inspired by something that I read about Mark Zuckerberg of all people. And it was all about the growth of Facebook and it was being called the Domino’s strategy. And the idea was that when Mark Zuckerberg began Facebook offing the Facebook, whatever it was called back then he began it just at Harvard and he got the initial support, like in his dorm or whatever, or in like a particular fraternity or whatever, and kind of went from there. But then he limited access. He said, right. It’s just people from Harvard coming in. So people, Harvard came in and they all mingled and everything, but then he saw that lots of people at Harvard, also had friends at MIT and he’s like, hang on. I can like double the user base there. So open up to MIT as well. Right. And then it kind of becomes obvious like, Oh, hang on. Those people at MIT, you know, loads of people from, I don’t know, U Penn or something like that, Brown and wherever and Stanford and just connect all the dots. And so he opened it up gradually just different colleges and universities across the U S and then eventually realized, hang on, this could be used by everyone in the world. So, you know, it was like, what was it only about 15 years ago now? I think it was when Facebook really opened up to everyone. And I really found that kind of strategy appealing because I got to think about my audience. And this is probably, you know, a big point to take away if anyone’s listening to this and they’re trying to build a similar group of publications is look at what you’re doing and what’s working, but then think about what those people also do, who they also mingle with, what are the kinds of, of domino effects you can bring into your thing. So with me, just to have one example for now, the people that were building Ruby apps and rails apps all needed to use JavaScript at some point in their app. So JavaScript was the natural second step for us. And it’s been, you know, the most successful publication that’s JavaScript Weekly, but it literally was just a domino from the first one. And we’ve tried to do that as we’ve gone on now, you know, we’ve got 10, 11, 12 publications. Each one has kind of had a slight overlap with another one. And then it’s taken on a life of its own. Once it’s had the initial boost.

Bryan Kelly:

When we come back, Peter describes his belief and how to best cultivate an audience. Plus he shares his secret to building audience loyalty, as well as telling me about a couple of his regrets. I’m Bryan Kelly, and you’ve been listening to Pushing Send from rasa.io.

rasa.io:

Creating email newsletters takes a lot of time. You might curate articles, write content, tweak your template, and look up metrics and not to mention you’re probably doing all of this once a week. Well at rasa.io, we said enough and built a free tool to simplify the process, which saves you time. It also uses AI to personalize emails for each subscriber based on their interests. That means they get stuff they like to read. Want to see how it works? Visit www.rasa.io and click how it works.

Bryan Kelly:

Welcome back to Pushing Send. I’m Bryan Kelly. Peter Cooper absolutely loves what he does. And as a result commands a lot of respect amongst other email newsletter publishers. Here’s Peter explaining his approach to audience building. A moment ago. You said there’s no plate, but you clearly have a guiding philosophy. How would you describe that in simple terms?

Peter Cooper:

Well something, I see a lot in the Facebook groups I’m in, for example, which I am, you know, various newsletter groups and also podcasting groups. Cause that’s another area of interest to me, one of the biggest kind of complaints or questions that I see from people it’s like, Oh, I’m trying to launch something and I can’t get anyone who is interested in it. And I haven’t got anyone that wants to listen to my podcast or subscribe to my email or whatever. Like what do I do? And I think the problem is is that you always need to kind of drink from some kind of well, you can’t just stand out in the desert and go, why’s no one paying attention? Hopefully, you know, just from being online and living and whatever, like you have some kind of audience, hopefully. If you’ve put in the time on Twitter over the years or Instagram or Tik Tok off or wherever it is, hopefully, you know, wherever you are, you will have at least like a hundred people that are kind of vaguely interested in what you have to say or think about things. Even if it’s your family, your friends, people that you work with or whatever, you know, you have to start from something. And so I’ve always tried to kind of use these different audiences that I’ve built as those kinds of wells. You know, when I need to build something, I kind of go and drink from that well that I’ve nurtured and made work over time. And that’s something that I think a lot of people who perhaps aren’t interested in publishing miss out on is that they think I can start with absolutely nothing, not appeal to any of my current audience whatsoever. And people will be interested, but that’s not true. You even need to kind of go back to that audience you already have, or you really need to sit and strategize about a way of leaning upon someone else’s audience. This is where like I’ll have people come to me and they’ll say, Oh, I wrote a really great article about topic I cover. Could you link to me or whatever? And they might have at the bottom of their article, you know, something like follow me on Twitter or YouTube or subscribe to my email or whatever, which is fine. I’m absolutely cool with that. But then they’re kind of leaning on my audience. They’re drinking from my well at that point, but you need to do something like that to make anything work. You can’t just say I’ve got no one listening to my podcast. What do I do? Like you have to go somewhere.

Bryan Kelly:

Was there anything you used in the early days to launch and build the audience? Or did you just get lucky?

Peter Cooper:

There wasn’t anything particularly clever or major that I did to actually get that initial growth? I pretty much got very lucky because there was a bit of a vacuum at the time for information about stuff that was going on in the programming world. So Reddit, wasn’t the big thing, but it is now Twitter was a lot smaller, although it was quite developer heavy at the time and it was less politics, definitely far less political and kind of celebrity stuff. And that is now, but I did get very, very lucky with that because I was the only one doing this type of thing. And a lot of the developer new sites were really, really struggling at the time. And would the thing, you know, people were less interested in subscribing to things of RSS at the time. It was just all a little bit of a downer. So in the JavaScript space, for example, this is where you pretty much had the main success was I launched there and I had been working with JavaScript literally since 1996, that is old posts. And they’re like silly pointless questions about Java scripts I’ve been working with for a long time, but I was never anyone of note in the JavaScript space like ever I’d never bought anything significant with it. It was just dabbler. And the people in the JavaScript space responded really, really well to the launch of JavaScript Week. And I had so many tweets from people that were kind of prestigious in that space saying, Oh, go and check this out. This is cool, blah, blah, blah. That JavaScript eekly grew really, really quick in its, you know, biggest publication now, but it was probably our biggest from a year end to be fair. It overtook the Ruby one really, really quickly. And I just got really lucky there. So the fact that that built me, that big audience through all the different recommendations that it got on social media and it got mentioned in like college courses and things like that. I’ve actually just kind of then on that audience really, really there’s been nothing super clever. We’ve done some collaborations, we’ve done some paid acquisition and things like that over the years, but you know, it’s been like 10% like our growth or whatever. It’s never been a huge thing for us.

Bryan Kelly:

Well, it’s clear that you serve your audience very well. And as a result have a loyal following of 500,000 plus subscribers, what would you say is the secret sauce for what you’re providing everyone on your list? Why do they keep coming back?

Peter Cooper:

As I said, I think we got lucky kind of early on just by being the only game in town. So that was obviously good. But then over time we built up that trust with subscribers who then move on to subscribe to all of our different publications and whatnot. And the tactic that I’ve always taken is that I need to know about all of these different topics bases that we cover. And I need to, frankly, together, a lot of the things we linked to and kind of make the point as to why they’re important, why they’re relevant. And we don’t do that in a, what you might call like a modern editorial, where we write a whole, several paragraphs about stitching various things together. We do tend to still keep it reasonably the list, but we’ve always had quite meaty summaries that also inject our kind of why you should be interested in this type of thing or perhaps sometimes why you shouldn’t like, don’t read this if you’re not doing X, Y, and Z. And people have built up that trust to follow our summaries and actually use them to determine whether or not to read certain things. So, you know, it’s a little bit like if, you know, a friend was recommending music for you or whatever, like, first of all, you either trust their sense of taste or you don’t. And if you’ve got a friend who listens to complete opposites of a music, you might not listen to a single thing they say, but if you do trust them generally, and if they provide some kind of provisos about some of the recommendations they make, they say, Oh, well I don’t, I know you’re not really into classical music, but it’s a classical music so good. It kind of sounds a little bit like sort of heavy metal with like bits and pieces, you know, they similar sort of rifts and stuff. And if you’re into heavy metal mapping, hang on, that’s really cool. I’ll, I’ll check that out because of what they’ve just said because of how they solve this thing. Whereas if they just said, go and listen to this video, like their product be a really good friend, you just delight blindly do that. So we don’t try and pretend to be like anyone’s best friend, but we do try to provide justifications for why we linked to certain things, unless it’s like super duper obvious in the title of something as to why something is newsworthy or interesting. So having those, summaries and those descriptions has actually probably been our, our USP really.

Bryan Kelly:

Well there’s of course, a lot of different ways that you can serve an audience and different audience are just that, right. They’re different. So while The Hustle or The Skim, or whoever may be doing one thing that may not fit your particular audience in, you found what your audience needs, which is great,

Peter Cooper:

It does feel different to some other topic areas. And, you know, I don’t work in, let’s say business news for example. But when I look at how people approach business news, whether that’s, you know, websites and major publications, or even things like Morning Brew. So another email newsletter, it just feels like an extremely different audience to a different approach, to what you have to adopt with people who are software engineers and working day in day out on software engineering. It just feels very different because it almost feels like to a business audience, like you can almost just give them a big bundle of headlines and they’ll pick and choose the things from that that kind of are relevant to their particular business interests. Whereas we have software developers, I dunno, this seems to be a little bit pickier and they kind of want to have justifications for things and they’re naturally suspicious of like a, company’s launching this new service, but like why they done that, whose technology have they stolen, stuff like that. There’s a lot more cynicism I think. And that might be a healthy thing. And also as you know, perhaps how our approach works in that space, you know, maybe our approach wouldn’t work so well in a generic business new space because I’d be saying, Oh, such and such a company has launched X, Y, and Z, but you shouldn’t really care about it because such and such a company’s already done this before, but someone who is looking for business news doesn’t necessarily want that interjection of my opinion, but yeah, maybe I’m just looking at it wrong, but that’s just how it feels to me. It feels like this is a space. You know, software engineering is a space where you do tend to trust people’s opinions more on why they’re sharing news with you perhaps more than just having a fire hose of stuff in your topic space.

Bryan Kelly:

I completely agree. That’s part of the reason why I wanted to talk to you in the first place. You have a unique point of view on this topic because of the world that you come from. My hope is that this inspires listeners to question and discover how to best serve their own audience.

Peter Cooper:

Yeah, absolutely. You know, it kind of ties into one thing that I think perhaps I regret slightly from over the years, which is that it seems that people really like to subscribe to other people to a certain extent. This is a particularly modern thing with email newsletters where, you know, they used to be quite generic and it didn’t really matter. like, you know, it came from a certain publication, but that was that. Whereas now you’re getting all of these different publications, including page subscribe newsletters that are very focused around the individual. So the people are looking for other individuals, voices, and they’re beginning to trust those people. So it’s almost like how some people like podcasts because they like the person that’s speaking and they like their tone and they like their opinions. And so on that idea seems to have spread somewhat into email, which originally was a less intimate all math, but now it’s actually becoming a more intimate format in this modern kind of 2018 last Renaissance of the email newsletter. It’s definitely a very big difference when we launch. And yeah, this is something that I’m wanting to try and work in more as time goes by. I want to try and get more of my personality and the metric, my name more and kind of appear more within publications rather than being this misty kind of Oracle in the sky that no one really knows who I am. So if there’s anything I’ve regretted, it’s not putting more character and personality in from the start, but it’s something that you can add in over time. But things, once an audience gets used to a certain approach, there is going to be some friction as you start doing things like that. So if you are a small business now and your trying to build a newsletter or any kind of online publication, essentially think from the off, does it, will it work for you being a particular personality, being a particular owner of a business or that type of thing, or do you want to keep it generic and in a way that, you know, if you want it to sell the business in a year time or whatever, it doesn’t really matter because your personality is not associated with it as much. Those are important decisions to make. And they’re just things that happened just kind of randomly. And without me thinking about it.

Bryan Kelly:

Is there anything else that might fall under the label of regrets?

Peter Cooper:

The other thing is coming up with more systems. We have a lot of systems for producing our newsletters, but coming up with more systems, do more robustly, allow other people to produce them on my behalf would be helpful because even though there are multiple people involved, now we have some external curators and so on all, but a couple of the newsletters still go through me essentially. So, you know, I’m the final say of like, this is what we’re doing. This is where it’s going, and this should go in and this item shouldn’t go in. And that means that, you know, if I want to take a week off, then pretty much the whole company does we do that each year. I, you know, take at least one or two weeks off, especially over Christmas. And we just shut down the company for that time. Of course that’s not so good if I get hit by a bus or whatever on it, you know, take a month off, whatever, that type of thing. So if I was in a position to do it all again, I would try and think of what are the ways that I can remain important to a business or a publication, but what are the ways that I can trust and be able to hand it off, to run on its own for certain prolonged periods of time. And that’s much easier to think about when you’re small and even if you’ve got a business and you’ve got a newsletter, that’s not the main business, but it’s anciliary can you outsource that production to an employee and have them run it, perhaps even if you have the final say of what goes in it, but can you have someone else handle that production and handle the, that work so that you’re not, it’s not contingent on you being around every single week day, whatever it is.

Bryan Kelly:

Yes, Peter Cooper was able to harness a mix of luck and intuition to create an email publishing business he loves. And while he shared some incredible perspectives about email, his opening about doing this for 20 or 30 more years is something worth pondering, email. Isn’t a trend. It can and should be something you’re investing in, regardless of how you’re specifically using it. Coming up on our next episode, we’ll hear from Sam Parr, the founder of one of the most successful email newsletter businesses of the past two decades. Sam has big plans and an incredible vision for where he’s taking his business. So you absolutely do not want to miss what he shares during our conversation. If you’re listening to pushing, send for the first time, be sure to subscribe at Apple podcasts or wherever you’re listening to this right now. So you don’t miss a single episode. And if you’ve enjoyed what you’ve just heard, I’d encourage you to check out a few of our other episodes while you’re here. Lastly, if you leave a review that will help us share these stories with other people just like yourself. So thanks in advance for doing that. I’m Bryan Kelly, and you’ve been listening to Pushing Send from rasa.io.

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