Why Did I Start The Ruffian and Has Paul McCartney Read My Book?
Answering Reader Questions. Plus a Ton of Optimism For 2026.
Catch-up service:
Best of The Ruffian 2025
How The Mad Men Lost The Plot Again
How To Do Politics When Nobody Knows Anything
When The Mind Outlasts the Brain
How To Choose Your Nemesis
My Ten Favourite Books of the Year
From Community To Tribe
In my 2025 round-up post I invited readers to ask me questions. Here are a few answers:
From Joe: Why did you start the Ruffian? And why do you think it's been successful?
The historical origins of The Ruffian are obscure even to me, but it evolved from an ancient pre-Substack sect called TinyLetter. I started The Ruffian on that platform in 2017. I wasn’t starting entirely from scratch. I’d built a following on Twitter. I also used to have a blog called Marbury, which mainly covered US-UK politics but strayed into other topics (shout-out to readers of Marbury!).
Why did I start The Ruffian? Twitter had pretty much destroyed Marbury along with most of the blogosphere. I liked Twitter but I missed having space to write at more length than I could in a tweet, without the pressure to write a full-length, grown-up article. I wanted somewhere I could write freely without smoothing off the edges, where I could try out ideas and thoughts. Hence the excruciating pun of the name (rough Ian).
I’d seen other people start email newsletters on TinyLetter (including Helen Lewis), and I thought, why not. It seemed likely that I’d missed the boat and that starting one now was futile, but I went ahead anyway. I liked being able to recommend things, and to bring people little gems of knowledge or insight I’d picked up online that week. The early Ruffians were basically Rattle Bags - I only started writing longer pieces more regularly later on.
I was able to build an audience in the low thousands within a year, mostly via Twitter, which at the time was friendly to links. After that it was a matter of plugging away, month after month, week after week (actually I didn’t write one every week, like I do now, just most weeks). I was working for free, the main satisfaction being the steady growth of my readership and the quality of my readers.
I did that for four years, by which time I had I had a substantial audience (20k?). The next big stage was moving to a new platform - Substack. Again, Helen Lewis was the trailblazer here, as far as I was concerned, although unlike Helen, whose newsletter remains free, my motivation was partly financial. I was self-employed and attracted to the idea that at some point I might be able to earn an income directly rather than via other publications. Substack was the only platform that enabled users to charge subscription fees (or rather made it easy for them to do so). So I switched over, taking my list and my archive with me. Once again I felt like a latecomer.
I kept The Ruffian free for a year or so, until in 2021 finally took the plunge and started charging for it - well, some of it. I was gratified by how many readers took up the paid option. (I continue to be. Thank you!) That was huge. It enabled me to finally become what I’d dreamed of being when I started a writing career, fourteen years previously: a full-time writer and thinker. (I still do some non-writing jobs but they tend to be related to my writing in some way.) Going paid also incentivised me to make a better product. I spent more time researching and writing the newsletter every week because I had to justify charging for it.
All those years writing the newsletter without really expecting much from it had underwritten what became for me, a life-changing success. The Ruffian has been enormously generative in all sorts of ways, connecting me to people and opportunities I wouldn’t otherwise have come across. (For one thing, as I’ve said before, I wouldn’t have written John & Paul without Substack.)
Successful Substacks do one of two things. They convey unique information about a particular niche - here’s the skinny on finance or China or home decoration that you can’t get anywhere else. Or they offer a regular chance to tune into a unique sensibility or voice - a particular way of processing the world; a sense of connecting with an individual mind rather than a corporate view or AI. I used to worry that I didn’t have a niche, that my topics were hopelessly disparate, until I realised that my newsletter falls into the second category.
Of course, these categories are not exclusive: many newsletters do both, including mine to some extent - I do try and bring the reader information they’re not getting elsewhere, so that it’s not all about my ideas/opinions - but they’re usually weighted towards one or the other. (Btw I think this model of value - unique info and/or unique voice - applies much more widely than Substack.)
You can draw your own morals from this story. Mine would be a) It’s never too late to join a bandwagon, and b) There’s a lot to be said for plugging away with low expectations.
From Clarke: Could you share more about your writing process or processes?
I fear this question because my answers are so meagre. I don’t seem to have a system or “process” to speak of. I just get it done, haphazardly but functionally. With the newsletter, the self-imposed weekly deadline comes in handy. I’m not one of those people who is constantly overflowing with ideas for pieces and I quite often feel I have nothing to say about anything. I’m sometimes in a panic on Friday thinking what the hell I’m going to write about for Saturday - although often it’s those ones which come out best and sound the most purposeful. I don’t know what I think - I don’t even know what I care about - until I start writing. That’s a lesson I keep having to re-learn.
One useful habit I developed is to write down ideas or half-ideas for pieces whenever they occur they to me. They sit in that list until I have another half-idea and find a match for it.
When it comes to book-writing, the hardest part, and the part that is probably responsible for 75% of a book’s success, is settling on an idea (a post in itself). The second hardest part is writing a first draft - you just have to commit to writing something quite shit and then go through with it despite your internal critic screaming at you every week, This is shit!
After that it gets a lot easier.
From Tom: Tyler Cowen voice: what are you going to write next?
Ha. Terrifying. I presume you’re asking about a book rather than next week’s newsletter. The answer is I don’t know. John & Paul has rather confused my sense of what kind of a book-writer I am (file under ‘nice problems to have’). It’s quite different to my previous books, on the other hand it’s been more successful. On the other (third) hand it’s not a book or format that can be replicated (I’ve heard all the ‘Why don’t you write about George and Ringo/Mick and Keith jokes, thank you). It is a kind of beautiful accident. I don’t see myself as a Beatles expert or a music writer. Having said that I’m currently toying with a Beatles-related idea - one last job and all that - so we’ll see if that survives interrogation. Longer term I would like to write another single-narrative book, like J&P, but compelling/viable subjects for those don’t come along very often.
From Joseph: Could another John and Paul emerge today?
This deserves a longer answer but here’s a short one. It depends on what we mean by ‘another John and Paul’. If we mean a musical partnership that changes the world in quite the way they did, then the short answer is no. They arrived at a particular historical moment, conducive to mass cultural experimentation. A big global market for teenage music and entertainment had emerged but hadn’t yet became fully corporatised. So there was room for great artists to singlehandedly shape and transform it.1
It also hadn’t fragmented into a million niches. It’s probably isn’t possible for anyone to dominate Western global popular culture like The Beatles did, creatively and commercially. Taylor Swift is a global hegemon although her dominance is more of a marketing and business story than a musical one - brilliant songwriter as she is, even some of her fans might recognise that she’s not as artistically original as the Beatles, or even say, Michael Jackson (actually the Swift-Jackson comparison is an interesting one, someone should write that). This may have something to with the decline of scenes.
A final answer is that even if those things weren’t true there still couldn’t be another John and Paul. I really think that they were, as individual musicians, or rather as a pair, sui generis, like Shakespeare in literature.
From Mark: I loved John and Paul. Besides the story itself, I was fascinated by how you write such a book. There is a lot of speculation about their thoughts and feelings — how much were you worried that Paul would read it and say it was all wrong, or just hate it? I would be paralysed by such a fear. (Do you know: has Paul read it?)
