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Stratechery goes solo: Ben Thompson on Asia, Apple, and the shifting tides of online media

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Over the past ten years, traditional media outlets from the pre-internet era have been forced to compete with online media outlets of various shapes and colors. Recently, upstart entities like Buzzfeed, Upworthy, and Business Insider have attracted the attention of media watchers for their tendency to appeal to a wide audience, as seen by their mastery of all-things viral. Those websites are remarkable, in part, for the deliberate facelessness of the authorship – you’re not supposed to know the name of a Buzzfeed writer, because all Buzzfeed pieces are designed to look and feel the same.

While the virality monster media outlets occupy one end of the forward-thinking media spectrum, websites that are extremely personality-driven occupy the other end. The Intercept isn’t just The Intercept, it’s Glenn Greenwald’s gig. Vox isn’t just Vox, it’s Ezra Klein’s latest project. FiveThirtyEight may as well be called “Nate Silver.” The internet has enabled audiences to value writers irrespective of the publications they work for, and The Wall Street Journal competes with an independent blogger and a cat video for that precious resource: attention.

Taipei-based writer Ben Thompson exemplifies how the internet has leveled the playing field in the media space, allowing independent writers to build up a following of loyal readers. Thompson began his blog Stratechery about a year ago as an outlet to jot down his ramblings on consumer tech when he wasn’t busy with his day job at Automattic (the company behind WordPress). Penning two posts a week, Thompson provided detailed analyses of whatever was making the news rounds at the time, with insights that were heavy on business strategy and light on fanboy hype. Somewhat unexpectedly, the blog exploded in popularity, and Thompson found himself placed among the likes of Benedict Evans, John Gruber, Horace Dediu and other brainy analyst-type bloggers.

Now, Thompson is turning his pet project into a full-time job with the launch of Stratechery 2.0. In addition to his twice-weekly posts, Thompson will offer up three subscription tiers in exchange for various perks, such as access to comments sections, daily e-mails, private message boards, and even a bound book of Thompson’s trademark sketches made on FiftyThree’s Paper.

To mark the occasion, Tech In Asia caught up with Thompson to talk about professional blogging, his stints at Apple and Microsoft, and observing the tech industry from an Asian vantage point.

What can followers of old Stratechery expect from the new Stratechery?

Stratechery is going to be what it’s been, but plus more for those who want it. Stratechery is about technology and strategy. It started about a year ago and I’ve been writing about twice a week. A starting point for each piece is usually the news of the day, and then I typically use that news to explain business principles, strategy, what’s happening and why it’s happening. I’ve been doing that as a part time thing, as I have another job. What I want to do now is focus doing it full time. So hopefully, my main articles will improve because I’ll have more time to spend on them. But also creating more content for members, getting sponsors for some of that content so it can remain free, and then doing things like podcasts and speaking.

It sounds like you’re transforming Stratechery from a personal blog into a one-man media outlet. Is it correct to call you a writer now?

I’ve always wanted to be a writer, particularly one focused on the tech industry. I think a lot of tech writers and tech bloggers approach the tech industry from a very product-centric perspective. That makes sense, because a lot of those people are engineers and they’re trained to think about products. As for my background, I was a liberal arts major in college but later felt like more of a business-type person. So I try to approach issues in tech more from a business and strategic perspective, where the tech and the product qualities are more incidental to the analysis. That’s not to say that tech talk is unimportant – it’s hugely important – but there are lots of people talking about that specifically, and I don’t think there are enough writers talking about how things work from an economics or business perspective. I try to ask “Why do businesses do what they do?” and answer that question as approachably as possible.

BenjaminWhen I started the blog, I did start it with an eye towards turning my personal writing into a full-time project. But I thought it would take several years before I reached a large enough audience to make that feasible.

At what point did you begin to feel confident that you could turn your hobby into a full-time gig?

It took off a lot quicker than I expected. the person I owe the greatest debt to is John Gruber, who about a month in linked to the blog and described it as the best new blog of the year. That helped get other influential people to read it. Another thing that helped the blog take off was the upheaval at Microsoft that happened shortly after I left. Since I was there I kind of had a unique perspective, and what was happening had a lot to do with what I was interested in. Also, the regular cadence has helped build the blog – two thoughtful and well-written pieces every week, whether it’s about Dropbox, newspapers, Chromebooks, or a whole range of things.

So you’re moving into full-time writing. Why not work for an established media outlet? Why go at it alone?

I think a lot of media outlets today are a good intermediate step from what we had before the internet. These outlets are made up of groups of people that focus on one or several topics. This enables writers to focus on writing, which is a good thing. But what I think is really empowering about the internet is that it makes a lot of things free. One of those things is publishing. I can publish what I need without needing to pay a newspaper or a printing press or any of that stuff. So from that perspective, the opportunity for a writer to go at it alone has never really existed previously. That’s an issue that I’m really interested in working through personally.

My primary cost is my own salary. I don’t have any other costs. That’s a huge difference compared to the way media was before. So what do I get if I go to a publication? Maybe some initial reach, but with Twitter and other tools, a writer can build up an audience rapidly on his own and keep all the gains to himself. Hopefully in my case those gains will exist!

The media model that you’re proposing hasn’t yet been tested. How confident are you that you’ll be able to support yourself and your family from Stratechery?

(Laughs) Well, you’ll have to ask me in a few weeks. I think the important thing that I’m asking myself is “What do I have for sale?” The articles that I’ve written in the past have been free and will continue to be free. That’s because words by themselves are easily copied. They’re not necessarily worth anything in and of themselves. But what do they bring me? Number one, they bring me attention. That attention is very valuable to advertisers, so that will enable sponsorships for the posts. Those advertisers can then reach the audience that I’m reaching, which is a very powerful one when it comes to VCs, executives at all sorts of companies, and people interested in technology all over the world.

Number two, what I can sell is ‘more of the same.’ For people that come back to my site every day looking for new posts – and I know those people are out there – I want to give them what they want, which is more. Number three, what I can sell is ‘access to myself.’ This includes guaranteed, thoughtful replies from me via email, a private message board-type thing, and meetups, both virtual and in-person all over the world. I plan to do at least three in the US, and a couple in Europe and Asia, where I can get the big fans together for dinner and drinks.

(See: Six months ago this startup set out to change popular media in Taiwan. And it’s slowly happening)

You’ve spent time working at Microsoft, Apple, and Automattic, but on Stratechery, you come off as “just a guy.” Do you see yourself as a tech insider? Or more of an average person who happens to enjoy writing about tech?

I embrace the ‘just a guy’ characterization. In my writing, I’ve never made a call to authority based on my experience or my background. I try to write very clearly, state my biases up front, build a case, and let the writing stand for itself. I think that’s something that’s really powerful about the internet in particular, where a well-written piece by myself is competing on an equal footing with a well-written piece by someone who writes for the New York Times. Obviously, the New York Times has a built in distribution mechanism which helps it maintain a large audience. But the internet enables writers like myself to build trust and build a reputation because of who they are, rather than because of institution that they happen to work for.

BenTaiwan-kidsYou have an unconventional background and unconventional career path compared to most. What were you doing before you started Stratechery?

Well, long before I started Stratechery, I did some computer science and engineering in college but majored in Political Science hoping to go into politics. I then quickly realized that the reality of politics wasn’t particularly pleasant. I wanted to travel and see the world, and I had always been interested in Asia, so I came over to Taiwan. I planned to stay for a year to teach English and travel. Then six years went by, and I finally left to return to the US with a wife and kids to go to business school.

In Taiwan I started out just teaching English, and then I ended up developing a system that made it easier to for English schools to teach in classrooms. I developed it for a chain of English schools and it’s all over Taiwan now. After that, I decided that I wanted to work in tech “for real” – it had always been a hobby of mine, and the fastest route for me to the US job market was business school. I went there basically in order to get the type of job that I wanted, but I ended up getting a lot out of it. My experiences there definitely inform some of my writing.

Tell us a bit about your stints at Apple and Microsoft.

I did my internship at Apple through a program called “Apple University,” which is basically a program that focuses on teaching you what makes Apple Apple. It was a fantastic top-level view of the company and gave me a deep appreciation for how Apple goes about things. Beyond the exposure to the company, I worked on developing a ‘course,’ as it were, about a specific topic, which I’m pretty sure is still being used. Unfortunately, with Apple being Apple, I can’t say anything more about it.

After that, I kind of sought out a job at Microsoft specifically because I thought it was the anti-Apple in a lot of ways. You can’t see every company, but when you see different extremes you can kind of extrapolate to figure out what’s happening at other places.

At Microsoft I worked for Windows as a category manager for the Windows App Store. I managed social, books and reference, and lifestyle categories with the app stores. So I was dealing directly with publishers like Kindle and Conde Nast and understanding what was important for them, and also becoming intimately aware of how Google and Apple structure their policies, and what developers care about, how they measure their ROI, what they thought about fragmentation – all these ‘words’ that we use when we talk about app stores and the web I got to live in a very real way. So that’s given me a lot of insights for when I write about apps and mobile.

How did the cultures compare between Microsoft and Apple?

I think that Microsoft has a very strong bias for action and getting stuff done right now, just so it doesn’t get stuck in a quagmire. Apple was much more deliberate and held a much higher day-to-day expectation of quality. Everything at Apple had to be perfect. Apple embraced the cost of making everything perfect all the time, and also embraced how those expectations affected the culture. Microsoft certainly wanted things to be great too. But after spending time at both companies, I’ve learned that doing things great all the time isn’t a switch that can be turned on and off.

BenTaiwan-friendsAs a writer, would you describe yourself as more of Microsoft-style writer or Apple-style writer?

I would describe myself as neither. I’ll admit that my experiences at both companies shaped my viewpoint, just like living in Asia has shaped my viewpoint, or how growing up in the Midwest has shaped my viewpoint. I’ve been criticized as being pro-Apple and anti-Apple, pro-Microsoft and anti-Microsoft, and I take that as a good thing.

Any myths about those companies that drive you nuts?

In general I’m opposed to anyone ascribing any actions or decisions to stupidity. The reality is that the vast companies in technology are full of very smart people. I think it’s more interesting to look at an issue with the assumption that everyone at a particular company is smart, and that they did what they were sure was the right then thing. After that, you can begin to consider what the constraints around them that led them to what some might perceive as a “bad decision.” There’s a tendency to ascribe malice without any context. I think that focusing on the context is another hallmark of what I do.

Living in Asia has helped me get an appreciation for grey area and nuance. That’s important to any analysis that’s more than just clickbait.

Tell us more about how living in Asia has given you an appreciation for nuance and grey area.

Any time you live in a culture different from your own you become aware of your own inherent biases. Once you realize you have all these biases and assumptions in one area, by extension you realize you have them in other areas. If I think one way about how people should drive, for example, and then I realize that a lot of that is shaped by where I grew up, then the implication is that I may bring similar biases to things like business analysis. Living abroad helps you appreciate context and appreciate different viewpoints. So the biggest impact living in Asia has had on me is it’s helped me look at things from a number of different perspectives.

What are some general differences you notice between the consumer tech industry in Asia and the consumer tech industry in the west?

Think about the classic Asian homepages, which to this day tend to be these massive portals with hundreds of links on them – in the US the standard has always been Google, with a text box and that’s it. When you think about how those early aesthetic preferences have manifested themselves down the line, it’s very interesting.

(See: OMG! Buzzfeed heads East, wants Asia to look at more cat pictures)

Let’s take a look at Line, for example. It’s very cutesy, there are all these features and sticker sets – it’s simply too much for the average US consumer. They just can’t handle it. In the US most people use SMS, which is about as basic as can be. And then here, on the other side of the world, you see these overwhelming messaging apps are much more popular.

Can you foresee any consumer-facing Asian platforms gaining mass-adoption in the west anytime soon?

Well, stepping back a bit, I think many people in the tech industry operate under the assumption that it’s winner take all. I think that may have been true during the PC era, and I think that’s the case on a country by country basis. Technology is transformative, but i don’t think that changes the human condition. I think it’s natural to expect different countries to develop in different ways when it comes to technology. There might be certain common needs – like communication, amusement, and entertainment – but the ways those manifest themselves will change and diverge.

BenTaiwan-chipsI find something like Line so superior as a communications medium than SMS that I can see it, or something like it, breaking through in the US just because it’s so much better than the alternatives – the same goes for WeChat and Kakao.

I think in general though, in the US we’ll start to see even more splitting up. Young people will have one thing, say, Snapchat. Then people in their twenties and thirties will have their own thing, maybe that’s Twitter. And then older people will have their own thing, right now that’s maybe Facebook. I think that heterogeneity is something we’ll start to see more and more of, instead of these massive dominant winners.

Are there any Asian companies in particular you look forward to writing about?

Obviously, nowadays everyone is talking about Xiaomi, and I think they’re interesting too, but I’m particularly interested in Lenovo. I’m really interested in seeing if they can replicate what they did for PCs in smartphones. I think the long-term trend in the Android market is rapidly decreasing prices, and while Xiaomi phones aren’t expensive, there’s a huge jump from the volumes they’re doing today to reaching the whole world, which Lenovo has already accomplished with PCs. Mobile isn’t PC, but there are some things that are replicable, and Lenovo’s reach might be one of them.

You spent a large part of your twenties in Taiwan and you met your wife in Taiwan. Beyond family, has Taiwan influenced your work with Stratechery in any way?

Taiwan is a great place to live, with a decent cost of living and good schools – that’s something that makes this more possible for me right now. If I were to do this in the US I’d have to worry about things like health insurance, and the cost of living would be much higher.

How come your Twitter handle is @monkbent? Any Buddhist leanings your readers aren’t aware of?

The ‘bent’ is obviously “Ben T.” The “monk” is due to an unfortunate choice of names from my freshman year Spanish class in high school. One translation was apparently “monkey,” so my teacher christened me Monkey Boy – which sucked at the time, but was kind of humorous looking back. My first email address was “monkbent.” “Ben Thompson” is a little too common and “monkbent” is always available.

Editing by JT Quigley

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