And I'm Chris Dywalt. And this is Not Dead Yet. We're all dying, but only some of us have been brought face to face with that reality. However long each of us have to do it though, we all want to live a good life.
One with meaning, love, and joy. And our guests are here to help us do exactly that.
All right, Ben Sass, why do you want to talk to Ben Thompson?
Maybe a better question is why would we not want to talk to Ben Thompson? He's helped remake journalism accidentally. He's an expert on the US-CCP long-term fight for the shape of the global order. There's kind of nobody who knows technology development both at a technical level but also at a strategic level. Seven of the eight biggest corporations in the history of the world are all American. They're all today. They're all tech companies. He is the expert inside gossip guy on all seven of them. Oh by the way he just happens to operate a side business where he's an NBA analyst. He is a weird and fascinating dude who I subscribed to a lot of his stuff in my last couple of jobs and when we were in DC we'd have Ben come in and tutor us on stuff and I miss him.
So this is a guy who you look to for insight on the tech sector broadly.
Yes. I mean, you'll do his bio here in a minute, but I mean, the guy could have been a financial analyst for all the biggest, most profitable companies in the history of the world, and instead he decided to do journalism about that, and he made that pretty dang successful, too. So, I find him a great technical analyst, both cutting it apart from the inside out and giving you a 30,000 foot view.
Okay. And he lives in the United States now, but spent some time, as I understand it, living in Asia. Is that right?
Yeah. I don't fully understand it. I think it was partly marriage or something, but I also think he liked having the time zones work for him. So he based out of Taipei for a bunch of years as the most important US-Pacific time zone analyst of the most important sector tech. But he lived in Taipei. But I think, you know, when you hear the drum beats of war, maybe it makes sense to come back to Wisconsin and raise your kids.
Okay. Things that may be germane for our listeners to know is that Ben Thompson is a graduate of the University of Wisconsin. He holds double master's degrees, one in engineering management, one in business management. After graduate school, he worked at a succession of high-powered corporations in the tech sector, starting with Apple, also WordPress. Shout out WordPress enthusiasts. And was at Microsoft when he began dabbling in the blogosphere and blog world. In 2015, he revolutionized the newsletter model of journalism with his newsletter Stratechery, I think is how it's pronounced.
Stratechery. He wants to get heck in there hard.
Oh Stratechery. Okay. Well there you go. I'd say it's Strateery. But that makes more sense if it's strategy. And it is the paid product that foretold the coming of Substack and has garnered tens of thousands and maybe more subscribers for a for-profit or for-pay subscription model for newsletters. So he's a guy who knows a lot about tech. He knows a lot about journalism. You like tech. I like journalism. Sounds like he's the perfect guest.
Bring on Ben. Ben Thompson, welcome. Glad to see you, my friend.
Thank you. I'm happy to be here. Quite the illustrious list of guests. I mean, you're scraping around at this point, I guess, huh?
Well, we can't decide whether we have you on here to cover the NBA playoffs, to cover the Trump sheeting, to cover the jobs apocalypse, the future of journalism. We got a few places to go. Let's start with bio and geography. You just moved home to Wisconsin a while ago. Tell our listeners the story of your career and how it spanned all the time zones and why you're back as a Badger.
Yeah, it's definitely a full circle quite literally. I grew up in Wisconsin, went to University of Wisconsin and then realized that I really wanted to travel, see the world. I was actually I thought what I wanted to do was I wanted to be a columnist for the New York Times. That is actually how this story starts. I had a job with a student newspaper. We're going to remake the student editorial instead of randomly posting once every few months like the war in Iraq or something that no one cares about. Like we're gonna write every single day and we're only gonna talk about five things that are relevant to students with city government, student government and state government. And actually we did four days a week. One day was letters to the editor and we did it every day for a year. And in reality I ended up being the one writing almost all those editorials which I loved. It was amazing. It was basically a preview of what I do now which is just write every day. Some people would say about the same thing over and over and over again. So, lots of full circle sort of in this story. Anyhow, I looked at the New York Times editorial page at all the bios, journalist, journalist, journalist. Like, I don't want to be a journalist. And then I got to William Sapphire, Nixon speech writer, potential criminal conspiracy. I'm like, that sounds way more interesting than being a journalist. I'm going to go into politics. And I lasted about three months and it worked on a Senate campaign and it was horrible. The reality of politics was a lot different than the sort of city and political science classes to say the least. So I bailed on that pretty quickly and I was working at the center for the deaf and hard of hearing typing on the little tell-tale type machines like helping them communicate and you know me being a political science major wanted to work for the New York Times subscribed to the New York Times was reading it every day sitting in my cubicle and there was a story about a bombing in Saudi Arabia and in that they interviewed a guy who taught English and I'm like I could teach English this sounds interesting wasn't deterred by the bombing at all. Anyhow, turned out I was always interested in Asia. I have some of my ancestry is Japanese. So I really wanted to go to Japan. They had this program called the JET program. Turned out I was a day late. I investigated the deadline was the day before. Friend of mine from high school, his older brother had just gotten back from Taiwan. He's like, go to Taiwan. It's better than Japan. Anyway, what year?
Uh I'll introduce you to some people.
This is 2003. So I go to Taiwan, travel, teach English, see the world. Thought I'd go for a year. Six years later, I came back to business school with a wife and a kid in tow. My wife actually deserves a ton of credit. She's like, all you do is talk and read about tech. Why don't you work in tech? And this is actually, I think, pertinent to the story that you'll appreciate, Ben. I mean, I grew up in small-town Wisconsin. The idea of going to San Francisco to work in tech literally did not even occur to me. It just wasn't even the realm of possibilities, even though I was super interested from like junior high on. And it was during the dot-com bubble. I was obsessed with it. It never even occurred to me to work at it. And I think that idea of not even being aware of considering opportunities is an aspect of growing up in a small town and in the middle of the country that people on the coast just can't even fathom that sort of mindset. But she was right. I'm like, oh, how do I get a job in tech? Guess I get an MBA as the shortest, fastest route, legit to the US job market. Came back, went to Kellogg in Chicago. Chance to be close to my parents, who were in Wisconsin, went to Microsoft, went to Apple, and then I got a job that I started Stratechery while at Microsoft with the idea of there's no jobs for people like me really in Taiwan anymore. I'd like to go back. I guess I need to come up with something I can do anywhere. And that's how I started writing Stratechery. And that was back in 2013. Started Stratechery, went fully independent 2014, and it's been my job ever since.
As you think about the way that the subscription model works, right? So, my hobby horse is about what happens next in journalism and what happens next for this. Talk about how you built your brand. Talk about how you developed an audience. Talk about the business of journalism where it intersects where you live.
Right. So when I was considering Stratechery, Stripe started in 2011 and they just come out with a product called Stripe Billing which basically managed subscriptions on your behalf. And so it was clear at that time I always felt bad I'd missed the blog revolution of the 2000s. I'd started a few blogs never kept up with them. I'm sort of the same age as like Ezra Klein and Matthew Yglesias. I saw their success. I'm like oh that could have been me. I'm too late. But it was already clear by then ads were not going to be a sustainable model for blogs in the long run. And but I'm like well the subscription thing I think is pretty compelling because ads depend on scale. If you're not going to have scale then you need to maximize your average revenue per user. The best way to do that would be through a subscription. And so I started Stratechery with the goal of it being a subscription business from day one. And the curious manifestation of this was I had lots of ideas, lots of takes, but I limited myself to posting twice a week. And the reason was I wanted when I launched a subscription product not to suddenly I'm dropping a paywall and people like what's going on here? I wanted to get customers who wish I was writing more and I was going to suddenly delight them. Oh wow, I can now get more stuff from Ben for a relatively low price. This is great. And that's basically how it worked out. I was measuring sort of subscribers on days I or people visiting the website on days I didn't post and I figured that was like sort of my metric that I'm watching and I got to that level way faster than I realized. I at that point did not understand the power of social media even though I was very online but Stratechery took off like a rocket like from the very beginning and so I watched subscription products a year later it was I missed all my initial goals but then seven eight months later I made my one-year goal which is 1,000 subscribers. I posted it that I made my goal and the next day it was the only step change in subscribers I got in 24 hours. I got 250 new subscribers, a 25% increase. What that was was people I was right on my metric, but because I was the first person to do this model, people were scared to sign up. They'd lose their money. I'd like go out of business. And once I like proved it, then a bunch of people signed up said, okay, I want to sign up all along. And then off to the races.
Does it help matter that you had an audience that was both narrow cast in terms of people who were deeply, deeply interested in tech and also that you had an audience of people who were very comfortable being online and interacting in that way. I assume that's a big part of why you experienced such early success.
No, I started I had 300 followers on Twitter. Literally no one knew who I was. So this was a totally different era of social media where there was real currency in sharing links and like that were smart and I did put a lot of thought upfront into the Stratechery branding. So number one name's hard to pronounce. I always make jokes about it but it's very me.
I blew it in our open. Don't Yes, exactly.
I don't mind people mispronouncing it. It's fine. It's Stratechery strategy and tech. The site was orange. The site had a custom font which back then was pretty rare. And I used to do all these hand-drawn drawings with all my articles. I miss those. I know they're a lot of work. But I did it every single article at the beginning because I want people to visit a link, say, wow, that was a good article. And to me, the most important article you post is the second article someone reads. Cuz if they show up and they're like, whoa, that's another good article, and I've been on this site before. I should start following this person because there's a consistency here. Consistency is super underrated, and I think super important. That was sort of my mindset in terms of building up that audience. And yeah, I had a 5-year plan when I started. Again, I had 300 I think 387 followers on Twitter. So, like I was like this is going to take a while. The fact that I was able to do it within a year, that's the social media aspect I'm talking about. Just like the speed with which I got followers, people paying attention was pretty amazing.
Two smalls there. We'll stay at journalism for a while. Chris should keep leading. But one, what was your plan on when you would be able to quit the day job and not have this be moonlighting? And two, who did you think the audience was at the beginning? And when you're jumping from 1,000 to 1,300, were they who you thought they would be?
Yeah, I think so. I mean, so my plan again, I thought it'd be four to five years, but like it just took off way faster. I think when I got to like 5,000 people that were visiting the site on days I didn't post. I'm like if I can capture over a year if I can capture 20% of those that is like going to be my sustainable business that I'm looking for. And so I think that was right. It was mostly people in tech for sure that's still my biggest subscriber base is I think like 26% or 27% of my subscribers are in the Bay Area or something along those lines. So, you know, the people who were very on Twitter in 2013 was definitely the customer base. And I should say all this sounds beautiful. I get to look back 13 years and say what a brilliant strategist I was. And I do think there's something to I've never managed Apple, but at least I've managed some sort of functioning business. It gives me some sort of credibility. But it was definitely a right place, right time. I was the first guy to do this. It was there was a different stage of Twitter where sharing links had currency. And there's definitely good fortune here. Like I get to sit in my pajamas and write about the big tech companies. Like it's I feel pretty lucky in that regard. But there's a bit where hey if you were the first to do it you get some traction there.
To brush past crass commercial considerations.
Everybody's running the numbers right now. Everybody's doing Price Times volume in their head like, dude, that guy's rich and he's in his pajamas. Go ahead, Chris.
Well, rich is relative, especially when you're covering tech keeps you extremely humble.
You're doing great as a journalist, which is like to quote Jonah Goldberg, the best gas station sushi in Alabama.
That's right. But your price point. So there are other people who are providing insider knowledge kind of stuff and they charge a lot. They charge thousands of dollars a year for people to get these subscriptions. Yours I think is like 150 bucks a year or something like that.
I started at $10 a month. $100 a year. I'm now at 150. And there's an intentionality to that. I mean, I think you can definitely make the case, many people make the case to me that I'm leaving a lot of money on the table, but I think money has never been my focus or goal. I'm making vastly I want to make $100,000 a year. I'm making much more than I ever expected. But there's I've optimized for my life. Like I am fortunate to have a job where number one, I can live in Taiwan for a long time. I'm back in the US. Went back to it for family reasons in that I spend almost all my free time in something that's family related. Right now it's driving to a lot of travel baseball, gearing up for a long time. And the other thing is just total independence. Like Mark Zuckerberg pays the same price that the person listening to this podcast does. And I don't know if assuming he's a subscriber the and there's a bit where I don't care what people say or think and if I make them mad that's fine.
And that can both be a big company executive, but it can also be someone I've had people that have like emailed in who I thought have been extremely disrespectful casting aspersions on my character. And I'll not only refund their subscription, I will go back and say, oh, you've been a subscriber for 7 years. Fine, here's a $750 refund. Like, I get out of my life. And maybe that's a bit of an overreaction, but it is a capacity that I place tremendous value on. And having sort of high volume, relatively low cost subs lets me do that. And also, I don't need to make stock picks. If you want stock picks from me, I'm going to charge you a whole lot more than $15 a month. I'll tell you that.
Well, you mentioned William Sapphire. I'll give you William F. Buckley, Buckley who used to write a mailbag feature in every week's National Review and they put together a compendium of his correspondence and the title of it was Cancel Your Own GD Subscription. So I like that. I like the energy and it sounds like what you've done here because I was going to ask you about audience capture.
The problem with the subscription base is that you become the property of a deep but narrow group of consumers. So it sounds like in your mind keeping it's totally a concern and it's a concern to the extent that I've probably left a lot of money on the table with the express purpose of avoiding that. And again this is a good fortune I had of blowing up relatively quickly. It was a very small amount of time where I had a large enough audience that no one had any sort of real say over me and I'm very grateful for that and I think it's a definite concern and yeah I again there's many aspects of this where turned out well for me. Timing was good. I got lucky and I think being able to avoid that is one of them.
All right, I've tortured you about the how. I think Ben Sass probably should now ask you about the what about what's in it. I'm sincere that we have six or seven topics we could each spend 45 minutes on and we're only doing, you know, 45ish total. So, this one will be small, but then I'll redirect us with to Chris's point about the why of tech. But, real quick before we go there, when you were writing only twice a week, you still had so much input from so many of the big seven or whatever the right number of tech companies was at that point. And you understood it technically, you understood it strategically, financially, you understood it culturally. You had to be really self-disciplined to let those ideas germinate and not just write every day and then be aged by 2 or 3 days from now when you were ready to batch a post. How do you write now? When in the week do you write? And to what degree do you have to self-consciously say, this one isn't ready for prime time yet. I don't want to write it out cuz I'll have to edit it later.
Yeah, there's an interesting there's actually a few different angles to that. So, one is I've experienced a couple of times where I will react to something immediately or I'll like tear up when I'm running cuz something just happened and I feel like the right response and I feel the percentage of times in which I vaguely regret doing that because I had a more considered take later is fairly high. So, I actually feel there's a regularity to posting multiple days a week like I do on a set schedule. And there's also more of a breathing time than you might think. Like, I'm going to wait at least until tomorrow. And if it happens on a Thursday or Friday or Saturday, I'm going to wait until the next week. That's sort of number one. I think it's been I've learned it's helped me avoid mistakes. But number two, at the risk of sounding arrogant, like at the end of the day, I will succeed to the extent my ideas are consistently novel and can stand to wait a couple days. And probably the preeminent example of this was Amazon bought Whole Foods, I think 2015, 2016. And I think it happened on a Thursday night. And so I was done writing for the day for the week. I immediately knew what my take on that was. I'm like, should I do an emergency sort of post sort of the next day? And I didn't. And I just waited through the weekend and everyone had their takes and I came out with my take on Monday, which I think was completely novel relative to what had been written over the weekend. And I think it was right. And it ended up being by far the biggest most viral post that I'd ever written. Like, you know, a million views in like a number of hours. And there was certainly an affirmative aspect to that of on one hand I benefit a lot from regularity and consistency. I think that's underrated. Quantity does matter. But there's also a bit where on the flip side like I having faith in myself and the ability to generate sort of a novel take that is not just sort of consensus in the moment driven. Ultimately, that is what has let me do this for 12 years, 13 years. And by the way, I get stuff wrong, but I try to come back and say why I got it wrong. What was my thinking process that went into it? And hopefully that gives me credibility with my readers to have strong takes elsewhere.
What did you say? Do you remember what you said about the Amazon Whole Foods deal?
Well, just in general, I think to understand Amazon is Amazon builds out these businesses that are scalable and broad easily accessible. The core example is AWS where they have like they have what's called primitives. They have storage, they have compute, they have all these different pieces and they have this problem internally of trying to coordinate all these teams and they're like actually there should never again be a meeting between our technical team and our store team. The technical team, you go build these building blocks with APIs and the other folks can use them or not. They're fully secure. You assume everyone's a stranger and if you do that, you can do the same thing for the whole internet. You can make AWS so it's available to everyone. But the way they got the scale to do that is they knew they had AWS as a customer. AWS is like the first best customer to do that. And that's what they've done with logistics. That they've done with their whole warehouse system is they provide the scale to get off the ground, but what they get off the ground is something that is meant to have an interface that anyone can interact with it, whether it be an internal customer or an external customer. And they've been trying to crack this grocery issue for ages. And I'm like, well, Whole Foods provides this first best customer to consume their fresh goods. You know, that's the hardest part of doing it. They have an outlet for that and they can sort of scale beyond that. The ironic thing is it didn't really work and but I definitely think that was the mindset of why they got Whole Foods. They needed an in-place customer to consume to sort of start to make a grocery production line that was sort of scalable. How they ended up getting to where they're at now actually and it had very little to do with Whole Foods in the end. But I do think I was sort of in touch with the way they were thinking about the problem.
Really, really good. I'm a free market guy, but given how much of the internet runs on AWS, I guess I'm in favor of making legislation that would ensure that AWS can't discriminate on the basis of viewpoint. And so, kind of like telephone companies not being able to deny service because of the views of the person talking on the phone. AWS in my mind is like an almost governmental function if it could be subject to cancel campaigns. Am I thinking about that wrong?
No, I think that's exactly right. I wrote about this previously. I framework for regulating content on the internet and this idea that there's like there's different levels of the stack. There's the actual consumer-facing bit. You move down into infrastructure like AWS. Below that there's the actual like telecommunications lines. Networking, all even down to components and your approach to regulation should differ based on where in the stack they are. And as part of that, the lower down you are, the more absolute should be the commitment to pure neutrality in terms of what goes over it. I'm open to discussions and I think I've become somewhat more concerned about any sort of insertion based on what happened over the last sort of five to six years in terms of the top layer. But I'm receptive to discussions about what the top layer that is actually displaying the content, what responsibilities they have. Anyone below that layer, it's not their job. It's not their responsibility. And if we need to codify that, I'm definitely open to that.
Okay. So your wife in I think you said '03 '04ish said, hey, you're into tech all day every day. Let's go to business school than that.
It was 2008. So I was a little older going to business school. I went to business school in 2009. When I was 29.
Then give us an 18-year history of Ben Thompson's historian understanding of tech. I often say to folks who are surprised that I don't talk about policy very much. Like I just think politics are way downstream from almost everything that matters. I think 100 years from now when you look back on our moment, you're not going to talk about our politics. You're going to talk about the fact that we're living through a digital technological revolution that remade the economy which is reshaping culture and community. And it feels like you can speak to almost every topic and you understood that tech was the queen of sciences. It was a meta field that was driving everything. How has Ben Thompson changed over 20 years about why tech is so central to what you wanted to study and write about?
Yeah. Well, I mean this was the basis I mentioned that I had why I reached out to you because you brought this up in your interview with Ross at the New York Times and I'm like this was such a brilliant bit from Ben and Ross just skipped right over it. We need to talk a bit more about this, but this idea that, you know, looking back in 100 years, the politics will be, you know, a footnote to the technological change, I completely agree with. And I thought the, you know, what you said in that interview was actually completely right on. I'm going to quote you if you don't mind. What's really happening in these super devices in our pockets, the largest tools any median individual's ever had access to in all of human history allow our consciousness to leave the time and place where we actually live, the places where we break bread, the people who are living next door to us, the people that you can physically touch and hug, the small platoon of real community, and we allow our consciousness to go really far away. First off, an incredible paragraph off the cuff. I mean, that is some A+ podcasting.
Morphine, morphine, morphine, morphine.
It's beautifully put. And I think that's spot on. We used to live our lives with what was in front of us and what was in the distance would pierce through our day-to-day occasionally like, oh, something is happening far away. There was some disaster or even a war like you maybe you went to the movie theater and you saw a reel before a movie about what was happening but that definitionally shows that the rest of your life you knew what was going on but you had no sort of ongoing relationship to it to this shift where yeah it's tragic people are living their lives and in DC and or on the world stage, but primarily through DC and occasionally their kids or friends will get them to put down the phone for a couple seconds and pierce through this pseudo reality to remind them that they're actually in a time and place. And it definitely tinges my coverage of tech. It's not something I write or talk about a lot, but it is an aspect in the back of my mind, which is to what extent am I documenting human ingenuity bankrupting the human condition, I think, is a fair question to raise. And I think something that I think a lot about personally and what I want to do is to what extent can I work to connect people, link people together and that's been a big thing in my personal life but I do think about that in terms of Stratechery like people ask am I worried about AI and I personally am not in part because there was once a world where oh you could brag about the fact I have subscribers in hundreds of countries around the world. At the same time, now there's increasing value to the fact that lots of people can read one thing and at least they know they read the same thing as opposed to whatever their AI personally generated for them that was sort of unique to them. Tech has this incredible atomizing experience. Your feed, my feed are all different. Your AI, my AI is all different. And any sort of commonality is, I think, increasingly rare and valuable. But then sort of like the other thing I would say and I'm gonna recruit you to my movement. As I heard you're not dead yet. Which is I call myself a reluctant accelerationist. So there's this I think we're at the nadir. I think right now it's about as bad as it can get because the atomization is nearly total. The conduits of that atomization are with us 24/7 in our pockets devouring our attention. And we're not going to go backwards. And I think that a lot of the people who level the critique you just leveled, it's married to this idea of rolling things back, which is impossible.
Possible given that we should actually be pushing forward. The worst possible thing we could do is to recognize how bad things are and pass regulations now to stop progress. And all we've done is lock ourselves in the worst possible place.
Yes. And so that's why I fall I mean I uneasy bedfellows with some of the overt accelerationistness. I mean I'm from Wisconsin the sort of home of the progressive tradition. So maybe I could like try to reclaim the progressive label in this regard given that a lot of progressives today seem to be the real conservatives but that's neither here nor there. You could see that though in a lot of tech discussions. I believe things can be better. I think there's things like the group chat. I think the group chat is one of the greatest gifts technology has given humanity. It's an opening to this new world where actually you can have a real connection with real friends on an ongoing basis in a society in a country that atomizes people where people live they move away they have work and they have family and they feel suffocated and more of that and I think we can do it.
All right. So when you joke about Wisconsin, I feel like we need to just bring Andre on here and both hug him, noogie him, and punch him in the face. Because if the choice if the false binary is safety versus accelerationism, I'm always going with optimism. But we got to be more clear-eyed about the challenges and like the subfight under this is the AI jobs apocalypse, right? I am ultimately on the side of the ATM created a ton of jobs even though initially 1968-69 in London 70-71 in the US. It shrunk the number of bank tellers or employees at a given bank branch from 29 to 12. And therefore, it shrunk employment inside banks until you realized, holy crap, if you could run a bank branch with 12 employees instead of 30. We can have five times as many because they become economically viable to have them in the suburbs. You don't have to drive to banker's hours downtown city center, try to park Monday to Thursday, 10 to 4, and have a terrible experience with the vast majority.
