TMW #144 | Writing for Martech

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Writing for Martech

“when it is truly time,
and if you have been chosen,
it will do it by
itself and it will keep on doing it
until you die or it dies in you.
there is no other way.
and there never was.”

-- Charles Bukowski, so you want to be a writer?

A couple of weeks ago, I was at a dinner with a few friends that I’ve made through TMW. Eventually, the conversation turned to writing – all three of us had been writing about Martech in some shape or form. And one of them said to me that they write to relax; it’s their weekend activity.

And I found this assertion that writing was a relaxing thing unbelievable on one hand – writing is hard work! – but totally relatable on the other; there’s something about it that is deeply satisfying and nourishing intellectually that it can become relaxing. But I didn’t really understand what they meant until I read the above quote from Charles Bukowski.

Writing is what Bokowski is talking about here. And his poem about it is well worth a read if you want to – or have to – create content for your job. His point is that writing is best done when it becomes a compulsion – something that satisfies you.

Over the course of three years, I’ve been writing about Martech every single week – with the exception of a few weeks over summer break and the odd sick day. But I’ve paid little attention to the writing itself.

If you’re a marketer who’s also writing content, some of the ideas in here might help you break out of the shallow, boring and ineffective prose that has come to flood social media and your inbox.

Part of the reason for this is the increasing amount of people who are creating content in marketing teams. WordPress VIP suggests that some teams have added content-focused roles by up to 50% from 2022 to 2023. There seem to be more marketers writing more than ever.

As with many other newsletter-ers that started up in the great newsletter boom of 2020, it’s around this time of year that a lot of these creators share a reflection. This past week I’ve seen pieces from the likes of Casey Newton, Benedict Evans and Frederik Gieschen. And so, I thought I’d throw my hat in the ring too.

So here it goes. Here are a few surprising, off-the-beaten-track lessons from committing to writing about the marketing technology industry every week. In this mega essay, I’ll break down how I write, why I write, the business models surrounding writing online, and why I specifically write about Martech.

This essay is a little self-indulgent in that it’s a reflection on my work here with TMW, but I hope it serves to encourage more people to write about the marketing technology industry – we need more independent perspectives!

Making the sausage

First, I want to unpack how, because I have been told that it’s not the way most people write, and it’s not something most people would sign up for; in fact, from talking to folks, they see it as a punishment – something akin to school homework. Maybe I’m a glutton for punishment. But here it is: how I write. I’ll let you decide if I am.

The first surprising fact is that all TMW content is created in the same week it’s published. I have no backup essays, or content that has been weeks or months in development, no drafts sitting in a folder somewhere. Everything is handmade fresh. It’s only recently that I’ve started to look at collaborating with other writers over a longer time span.

My writing takes an unusual shape. On Tuesdays, I’ll write all day for our TMW PRO market review, which is a recap of all the main things that happened in Martech in the past week. It’s one and done in a single day. Same goes for the TMW Sunday newsletter, which can span between 2,500 or 3,000 words, and 3–4 original charts. This too is usually written in a single day, from 9am to (usually) midnight. And very occasionally, I’ll get the idea for the topic that very morning.

I do it this way because TMW is about what’s happening now, not what’s happening in the ambiguous future or distant past. And so, my schedule demands it. But there’s more to it. Writing this way has become my best defense against overthinking or over-researching a topic – something that plagues so many would be great industry writers.

I’ve also found it extremely difficult to jump in and out of a stream of consciousness when I write over several days. Doing it in a day is how I can get to a deep state of thinking.

Aside from my weekly routine, my writing process follows something James Clear defines brilliantly as optimism, pessimism, and then optimism again:

“Optimism early, pessimism in the middle, optimism late.

Your starting position has to be somewhat optimistic or you’ll talk yourself out of getting started. Believing in what you are about to do does not guarantee success, but a lack of belief can prevent it. Once you’ve committed, pessimism becomes useful. Question things. Find holes in your plan. Hold yourself to a high standard and try to identify your mistaken beliefs before they become your misplaced actions.

After you’ve spent some time troubleshooting, it’s back to optimism again. Nothing will ever be perfect, but you have to act anyway. Progress requires the courage to forge ahead despite the inevitable obstacles.”

During a session, I start writing with a general idea or direction. Sometimes it’s reporting, like my recent essay unpacking the CDP whistleblower claims against Salesforce. Sometimes it’s a fresh perspective on something done to death, like my generative AI series looking at how marketing change in the long tail of generative AI, AI and the channel (r)evolution and the content cold war. Sometimes, I just want to learn something, and writing about it is one of the most efficient and effective ways to do that, like when I investigated Eric Surfeit’s view that Everything is an Ad Network. Sometimes there’s a big glaring problem that needs unpacking, as demonstrated with my essay on The Grifterverse or why Martech is not getting used in business. As you can see, there’s no one and done approach.

The commonality between these different ideas is that it captures me. Sometime in the week – whether at the gym, or in the shower (don’t picture that), or playing with my kids, I’ll be thinking and ruminating on something in the Martech industry, and then an idea will strike me. It’s a visceral, emotional lightbulb moment. The best way I can describe it is that I’ve settled something – the focus of that week’s Sunday newsletter is now set into motion.

There’s a connection between my thought life, research, and subconscious ruminations that become a trigger for a TMW Sunday newsletter. But more importantly, the act of writing is like a little protest against the constant tug to just consume media, information, and content all the time. It shifts my mentality from a passive consumer to an active contributor. Frederik Gieschen explains the concept like this:

“But to me, writing is about so much more than earning a living. It shifts your mindset from that of a consumer to that of a creator. Everyone needs at least one creative outlet in their lives. We spend most of our days consuming what others have made, whether it’s reading, watching, or listening. I believe it’s crucial that you cultivate at least one place in which you truly express yourself. Forget about sharing and forget about money. Just find one creative activity that you enjoy and that allows you to express and reflect on your unique experience of life. I don’t know what suits you best. For me, it has been mainly writing.”

It's this weekly wrestle, that really sharpens my thinking. The idea that I must show up for you every single week to deliver a sharp, compelling, and helpful piece of work brings a healthy rhythm to my working life. I know that at some point I will have to arrive at a concept, and lately, I’ve been more likely to just trust that something will hit me, which gets me to my main point here about inspiration: good ideas come at you, not from you.

With the concept in hand, I will then spend 2-3 hours writing roughly 1500 to 2000 words. At this point, it’s all lateral thinking. Even as I write this sentence during a 2-hour drafting session while on vacation at the beach, I’m literally writing as I’m thinking; no research, no prep, no editing. Just a stream of disconnected thoughts.

This initial stage is the most freeing aspect of any writing project. You can decide what goes on the page, and it can literally be anything. What I’m doing is pointing in a general direction and seeing what the terrain looks like as I move towards it.

Sometimes I’ll spend time across grand vistas and sweeping landscapes; sometimes I’m trudging through mud, or am lost in the forest. It’s ok, because the point of this stage is that you’re wanting to only encourage yourself; the criticism comes later. Your job is to be optimistic.

After I’m done with an initial draft, I’ll go to town researching it. There are two levels here. For the first level, I’ll ask myself questions or point to references – that’s my starting point. Usually, I already have a few links to pieces I should read. Then I read for 3 – 4 hours or sometimes more, literally just reading, grabbing quotes, and chucking them into the various spots in the essay. I’m asking: what’s challenging my thesis? What agrees? Can someone articulate what I’m trying to say better than me? What are the facts?

After that, I’ll move on to charts. I create charts when I have a solid data point to present that strengthens the overall essay. They exist as a visual aid for a specific point I’m trying to make. I’ll again spend 3-4 hours on making charts, sourcing data, and experimenting with visualization. The benefit of running a newsletter is that research like this does compound over time: I’m currently sitting on over 10,000 resources saved over the past three years of writing TMW, making it far easier to find vetted material, data, and content.

It's important to stress that this must come AFTER you write your first draft. The main reason is that I don’t want to contaminate my thinking with someone else’s opinions before I write. Coming at a topic as a blank slate is where the magic happens, where you’d find stuff that no one has said or thought about before (at least publicly and in writing).

After this is rewrite the essay from top to bottom with the research in place. I’m linking sources out, cleaning up paragraphs, and deleting stuff. I aim for a 10% haircut on total word count. This is where all the high-quality work comes from, and where the past 5-6 hours of thinking becomes a great benefit – you’re not going to forget what you’ve already done, so you can do this much faster.

As you can see, there’s a flow: optimism at the start – you need to believe you will create something great today and be very fluid and creative; pessimistic when researching and refining your work to ask the hard questions of it; and then become optimistic again when you release it out into the world. In the end, a lot of the mental struggle with writing is just not having enough faith that you can create excellent work that can move an entire industry.

After all that, I send it to my copy editor for a fact check, grammar, spelling, and stylistic review, and after a few last-minute tweaks, it’s in your inbox. That’s how the sausage is made.

How I think about writing

The reason I just gave you my process in full is because it serves as a necessary backdrop to how I think about writing. To me, writing is not something you do; it’s a mentality you embrace. Writing is thinking, and thinking is writing. So it’s not about doing a task, or completing a project, or writing words on a page. I see it as a courageous act of finding out what you truly think about something. It’s a radical rebellion against groupthink, headlines and the social programming that is all too prevalent today.

There is no thinking without expression, as Larry McEnerney from the University of Chicago Writing Program argues. Writing forces you to put thoughts into real words on a page, assemble them in a logical order, and present them to someone else in order for them to read them, and think.

There are other perspectives out there. Writing course instructor David Perrell from Write of Passage promotes his $4,000 writing course on a different kind of promise – that writing is something that can help you earn your freedom, become an entrepreneur, divorce your time from your money, or become a person of influence. From a recent marketing email promoting his course:

“You see it all over Twitter. Side hustles turned six-figure businesses. Followers becoming customers. Viral tweets attracting new clients and job offers. People everywhere are finding freedom by writing online. The thing is, freedom looks different for all of us.

What does it look like for you? Maybe it’s leaving your current role and going all in on that side project. Maybe it’s getting promoted to the position you’ve been eyeing for years. Maybe it’s attracting so much demand to your business that you get to choose the clients you want and set your own schedule. Whatever your vision of freedom looks like, you can achieve it by writing online.”

For me at least, writing has absolutely nothing to do with this. In fact, writing professionally for an audience is one of the hardest ways to make money, where the one-percenters get to enjoy the lion’s share of rewards.

Instead, writing can become a central part of your intellectual life. Writing should be like exploring new intellectual domains, as a search for truth and ideas. Not a way to “achieve financial freedom.”

With each essay, my world becomes a little less ungrayed (like a game Age of Empires), it opens up new space for me to learn, and read, I hope it does the same thing for you. That’s the real benefit – you get to see the world clearer than you have before, and that’s reason enough to start.

And so the question remains: should you write? The real question is: do you want to think for yourself? All of us make decisions every day, using our judgment and worldview. Wouldn’t it be nice if that worldview was challenged a little bit, in order that it might grow stronger? The greatest benefit of writing is that it is like a workout for your judgment faculties.

Great writing is great thinking which in turn produces great decisions. It’s like an essential intellectual workout that influences my daily personal and professional life. And over time I’ve seen this permeate the way I talk, what I spend time on, my public speaking skills, and how I approach a wide range of decisions.

So if you’re wanting to write to earn attention or make money, it just isn’t the right career for you. You’ll be too frustrated with it. Go and sell B2B SaaS instead if you want that. Writing is for intellectual pioneers – those brave enough to step out of mainstream and radically explore new ideas and concepts to get to what they truly think about something.

And yes, it’s true that I am now making money from writing TMW. Which brings me to the business of writing.

The business of writing

Most people in the world don’t get to marry up a passion with a revenue source, and somehow after jumping careers three times and landing in marketing tech, I’ve found mine.

But the business model of writing is very hard, and for most, not lucrative at all. But the great thing about selling subscriptions to TMW PRO is that there is an unlimited, uncapped upside: it’s high margin (roughly 80%) because it’s just online content and creates intrinsic growth dynamics when the content is good. Sound like a good business model? Yes and no.  

What I’ve learned is that most people won’t buy a subscription to TMW PRO. My current conversion to a paying customer is 1% of free subscribers, which isn’t too bad! But the reality is that you’re not going to become a unicorn if your business model is based on asking people to pay for your content.

But the advantages are very strong though if you stick it out. Creating media products is very similar to consulting, selling courses, or building a software company, because in most cases there are very low barriers to entry. That’s why there are so many one- or two-person consulting shops, or why over 10,000 software startups apply to join Y Combinator every 6 months. If you wanted to, you could start a Substack today and start publishing.

What this reflects is a unique situation in communications history where social media, search, and the open web have enabled literally anyone to build a media company – you no longer need to buy a printing press, or build a TV studio, or buy radio and television transmitters to get your ideas and thinking into the hands people. And now almost everyone is literally online, making the prospects for online media almost infinite.

Casey Newton in his recent reflection on building The Platformer explains the ease of entry with media today, as well as the value of starting something relatively small:

“But there are more positive reasons to strike out on your own, too. You can get started fast. The overhead is low. The email addresses you collect are yours, forever. Every day it becomes more common for the average person to become a paid subscriber to a favorite creator, whether on Twitch or YouTube or TikTok or Substack. And the economics are good: at $10 a month, 1,000 subscribers should pay most of your bills in any city in America.”

And while the barrier is low, the journey beyond it is long. Media companies, when done well, take years to grow into something with real enterprise value. Morning Brew, the gold standard of newsletter success, started almost a decade ago. The New York Times, on the other hand, started in 1851 – a solid 172 years ago, and its founder Henry Jarvis Raymond is well and truly dead.

And while you can get short-term viral hits or grow newsletters quickly by buying subscribers through ads, writing engagement-baiting social posts, or relying on software companies to build recommendation loops for your newsletter, I doubt that flash-in-the-pan growth reasonably contributes to the kind of long-term brand building that legacy media has earned throughout the decades.

That’s what makes media – and especially writing – such a high-stakes game. You have to have the conviction that enough people will want what you’re creating, and for that to be true
ten years from now. Otherwise, you could waste a decade of your career building something that not enough people will want.

Unlike software, you can find product market fit and then scale up from there because usually, the products and services are utility-based – do people gain practical value from it? This is not especially true about media companies, because there’s no specific practical value in it.  

If you’re running an advertising business, this doesn’t apply; there’s huge practical value in advertisers buying ads to grow their business. This is exactly why I don’t run ads on The Martech Weekly: it would sour its purpose – to deliver the most value to readers possible.

Knowing who your customers are is extremely important to your longevity as a writer. If it’s turning words into ad dollars, that’s fine. But for me, I prefer my customer to be my reader.

In the greater shift to using generative AI to create content, people will want to connect with media brands and content creators that are genuine, and my hypothesis is that the divide between high-quality work created by humans and AI-generated sludge will widen, and people will pay for the difference.

But the value in creating media that lasts is huge and transformative – not from a company point of view but from a societal and industry level. The example I often cite is a boutique croissant shop called Lune. It was well known in Melbourne for its hyper-focus on croissants, but it wasn’t until an NYT food editor asked the question in an article – Is the World’s Best Croissant Made in Australia? – that it transformed their business. More than 7 years since that article was posted, there have been lines around the block every single day of the year.

The NYTs have this kind of people because it attracts people with money, sophisticated folks who like to keep up with a high-quality and informed source of news. In this case, people trust the food editor’s opinion of quality.

One thing I’ve found delightfully surprising about writing is that it helps you define your crowd in a similar way. People will reach out to collaborate, promote TMW, to have a conversation, and more often than not these people are thoughtful, reflective, and super curious. Beyond the commercial impact of writing, drawing a network of contacts that share similar passions and virtues must be the highest ROI activity I can think of.

That’s the cultural and societal power of media. The real value is in its total influence over what people think. I often joke that the job of writing is to enable people to outsource their opinions, and even though it’s a joke, there’s a grain of truth in it.

When you’re creating with words, you’re working at the level of worldview, and it’s a huge responsibility because the opinions people form about how their business should run, or what they should focus on in their career, or what they want out of life, is hugely influenced by these very words.

Why Martech?

I could write about anything, so write about Martech? Despite the advice of a lot of content creators to focus on a niche, I haven’t gone down that path exactly. Yes, the intersection of technology and marketing is small compared to other intersections such as Fintech and Healthtech, which makes it a niche.  
But there’s a lot of diversity in there. There are about 11,000 companies across dozens of categories, with the industry worth more than $509.8 billion.

The TMW audience is from all over the place, from journalists to researchers, consultancy leaders, product marketers and founders – there are a lot of different people coming for the same thing.  

So it’s a little broader than, say, writing about analytics, or email marketing specifically, which can be a disadvantage when you’re trying to find other people who are similar to your readers.  

But I think that the reason I’ve stuck with Martech specifically is that it’s just so damn fascinating. A lot of advice on Substack purports that the thing that matters is that you’re writing and building a business around that, but writing for a specific community of people and working to be a force for good in it is more appealing.

For me, it marries my personal interest in understanding how the internet is changing society with my commercial interest in how marketing technology is created, implemented, and used. In a way, Martech and Adtech are the spaces that have a huge influence on people’s lives that are mediated by tech.

The power of words can transform our lives and societies, and Martech is the specific domain in which I see huge problems in content trustworthiness and people making bad decisions because of the media environment. It's for this reason that I’ve committed to writing about Martech.

But at its core, writing consistently is one of the best ways to build a trusted brand. TMW exists to simplify what is happening in an incredibly complex tech industry. In a way, even though I’m writing about Martech, I’m really writing for Martech.


P.S. If you made it to the end of this huge essay, then maybe this is a sign that you should start writing? After all, the Martech industry can only get better with more experts like you bringing your insights to the table. You don’t need to be a journalist to make an impact – I am definitely not one of them! We’re currently interviewing folks who have reached out with interest to support our research for a part-time writing role. Reply to this email to learn more.

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Want to share something interesting or be featured in The Martech Weekly? Drop me a line at juan@themartechweekly.com.