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

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.

When 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.