Big Bets on Big Tech with Alex Kantrowitz

Alex is a journalist, author, and the founder of Big Technology. On this episode we discuss his decision to go out on his own

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Alex Kantrowitz is a journalist, author, and the founder of Big Technology, a one-person publication focusing on the biggest names in tech: Amazon, Apple, Facebook, Google and Microsoft. Before he struck out on his own, Alex was a reporter at Buzzfeed News. On this episode, we dig into his decision to bet on himself as a creator.

Episode Transcript

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(Coin Drop)


MESH VO: Hey everyone, Mesh here. In last week’s episode, we spoke with entrepreneurs who’ve made careers out of sharing their passions online. Today, we’re revisiting our conversation with journalist Alex Kantrowitz. Alex was a star tech reporter at Buzzfeed News and is the author of the book Always Day One: How the Tech Titans Plan to Stay on Top Forever. During the pandemic, Alex has used his entrepreneurial spirit to strike out on his own, with a paid newsletter and podcast called Big Technology. He’s also co-hosting this season of the Vox podcast Land of the Giants, which focuses on the inner workings of Google. 

In this era of overwhelming news, thinkpieces, and clickbait, controversial opinions get just as much attention as responsible reporting. How do we create a world where journalists can cover their own interests -- and bring about a more informed public? The tension between media and technology is thick, and Alex is taking his chances.

Let’s get started.


Mesh: [00:00:10] Are you passionate about technology yourself? Did you use all these platforms? Were you just fascinated with it? Did you like the people behind it? What was your personal interest?

Alex Kantrowitz: [00:00:16] So the bottom line is that technology is shaping our society right now. There's no two ways about it. You know, the companies that I cover in my book, Always Day One, they are shaping the way we exchange information and the way we buy things. And they're the [00:00:30] dominant five firms. Apple, Amazon, Facebook, Google, and Microsoft [00:00:35] not only in the US economy, but in the global economy. And when these companies press a few buttons, it can change the way people think about things. It can change the way people do things. I mean, an Amazon official that I spoke with recently said, Amazon basically knows the lifestyle of people in any zip code you pick. [00:00:52] So it can tell whether you're living in a zip code that has a lot of [00:01:00] skiers or, you know, people who are interested in reading, it can basically tell you what those people do. [00:01:14] So I think the fact that these companies have so much power. They're shaping the world that we live in today. To me, that's fascinating. And because it changes so often. There's an amazing role a reporter can play, which is to figure out what's going on behind the scenes and explain to people what those [00:01:30] changes are and what they mean for their lives.

Mesh: [00:01:32] And given the experience that you had interviewing people from a lot of these technology companies. You developed a deep expertise in it, you got exposed to so many different leaders. What stories have you covered that you're most proud of?

Alex Kantrowitz: [00:01:47] I mean, I think I'm most proud of the book. So at a certain point I decided that it was important for the public to know not only what these companies do, or what you might think of as the symptoms, but how they [00:02:00] operate inside. And that's what I call the physiology. I think if we understand the way that these companies work, we can really understand their decisions in a much deeper fashion, which can help us understand the role that they're playing in society. So the book was tough. Took two years to work on. Many, many nights and weekends and holidays spent trying to figure out what's going on inside them. And then eventually trying to figure out how to tell it in a compelling story. [00:02:26] But I think that anyone who picks up the book and puts it down having [00:02:30] finished it, will really understand what's going on in Silicon Valley and with these tech giants in general, in a way that isn't typically explained in the press. And I'm proud of that.

Mesh: [00:02:38] And do you believe that gave you an advantage for building a relationship with these companies, so that you could report on them the way that, not only you wanted to, but maybe that they would be perceived in a way that they're not in other media?

Alex Kantrowitz: [00:02:51] Yeah, look. I think that the tech giants, um, when anyone says, hey, I'm interested in how you do what you do, uh, that's going to pique their interest [00:03:00] because you know we're all living on this treadmill of news right now. Where it's just like news cycle after news cycle, after news cycle. And it's impossible to keep up. [00:03:09] And so when somebody comes in the front door and says, hey, let's take a pause for a second and sort of explain what's going on here. Yeah, I think that is of interest to the tech giants. And for me, it definitely helped as a reporter because now I can look at every story I work on with a bunch more depth having been inside these companies and being able to understand their decisions in a much [00:03:30] deeper way.

Mesh: [00:03:30] How is it building relationships within those companies to get the stories that you wanted? Did you find it challenging at first, or what was your approach to that?

Alex Kantrowitz: [00:03:40] Yeah, it's super tough. I mean, whenever you start out on a new beat as a reporter and you reach out to people, that natural reaction is going to be, all right, well, who the hell are you? And that's definitely what happened in the beginning. But I think the cool thing about this job is you, you get what you can, you write it and then you publish it and then you [00:03:57] do that cycle all over again. [00:04:00] And you know, people do read what's going on about them and about their companies. And you'd be surprised to see how, how people in senior positions will read so much about what's going on in their company in the press. They're addicted to the coverage. [00:04:15] And so eventually you build up a reputation, good or bad. And people say, is this someone who's fair that they're trustworthy? Do they, you know, tackle the tough stuff while making sure to mention the good when it's applicable. And if you do that enough [00:04:30] times, you know, you'll get the trust of both the communications executives inside the companies [00:04:34] and then more importantly, the rank and file who will speak to you out of turn or, you know, outside of the auspices of the PR operations inside those companies. And that's when you start to get the real story, not just the polished version meant to be told to the press.

Mesh: [00:04:51] Were there any interviews with specific people that you were, you know, more excited about than others? Or maybe a bit, [00:05:00] wow, like how did I get this interview?

Alex Kantrowitz: [00:05:03] The most interesting interviews I've done have been the three times I've gone in to see Mark Zuckerberg. And Zuckerberg doesn't really approach an interview like a typical CEO. So most CEOs, you'll sit down. They'll talk to you for 25 minutes about a new product that they're going to release. The PR person in the room will gauge your facial reactions. [00:05:22] If you look kind of disgusted, they'll say, okay, thanks for coming. You know, if you seem engaged, they'll say, okay, and here's five minutes for [00:05:30] questions. But Zuckerberg doesn't operate this way. When you go in to see him, he's constantly interested in asking what you think, and asking for feedback about what the company is doing. [00:05:40] And actually feedback is a big part of the way that Facebook operates internally. Um, and by watching Zuckerberg sort of starting to ask me, what I think, I started to ask Facebook people, whether this is a normal behavior inside the company. And it turns out there are day long or two day long trainings for [00:06:00] Facebook employees about how to give and receive feedback. [00:06:02] And there’re even posters on the wall that say, feedback is a gift. So Zuckerberg, his interviews were interesting for two reasons. Not only where they atypical for a CEO. But they also cued me into a little bit of Facebook's culture. And whenever I'm having a conversation with these executives, I'm always looking for little hints of the way that they operate as leaders inside their company. And with Zuckerberg [00:06:24] you definitely get it.

Mesh: [00:06:25] How did that even come together? I gotta imagine there's a ton of people that want to talk to Mark [00:06:30] Zuckerberg. What was it about you that got you into that room? Not once, but three times.

Alex Kantrowitz: [00:06:36] I don't know if there's anything special about me in particular. I mean, I happen to be lucky that I was working for Buzzfeed, which has a large audience of people that are pretty desirable to Facebook. These are young people who are the quickest to try to, you know, quickly run away to a different competing platform, whether it's Snapchat or TikTok [00:06:56] and I think Zuckerberg has an interest in speaking with them. And I [00:07:00] was the conduit to do that. Um, of course, with a filter. You know, I’m not going to just transcribe and throw whatever Zuckerberg says out to the Buzzfeed audience, but I definitely was, you know, a vessel through which he could get his message out.

Mesh: [00:07:12] And as a reporter how important was it for you to build your own audience? Did you have to do that independently or did Buzzfeed play a big role in that.

Alex Kantrowitz: [00:07:37] Yeah, I always thought building my own audience was super important. // You know, I realized that we were living in the digital media environment where [00:07:57] // you sort of count the years that you work at a company, [00:08:00] uh, in dog years usually multiply by seven, sometimes eight, depending on the company you're working for. And so I figured it was important for me to, you know, build up an audience. But honestly building up a community on Twitter to me was also more fun.[00:08:14] Like it's really exciting to be able to throw ideas out and just have // real time feedback from people who are reading along and following along the same stories. And, you know, that makes you smarter and you can always take conversations from the feed into direct messages. And you might hear [00:08:30] some more honest opinions from people. [00:08:31] You might get stories from it. Uh, this might end up, you know, getting your stories more traction. So yeah, I mean, you know, the goal for me was never to build a Twitter audience, to make myself super prominent. It was always to build a community within which I can engage and learn. And that's been the best part of it.

Mesh: [00:08:51] How long do you think it took you to create, quote, unquote, a real following where you felt like you could throw things out and people would comment, or maybe when you felt like this [00:09:00] was a potential change in your career.

Alex Kantrowitz: [00:09:07] Yeah, it took years and years for sure. Um, but I think that you eventually hit a threshold on Twitter. So I spent almost all my time on Twitter, uh, when I'm not writing and interviewing (laughs), for better or worse. And you do eventually hit a threshold on Twitter where, you know, if you write a tweet, someone will engage with it. [00:09:27] If you ask a question, someone will reply. [00:09:30] And if you write something insightful, it will make its way around the internet. I don't quite know exactly when that was or what the critical mass is, but // it's a pretty amazing threshold to hit because you know that you have this big megaphone and // you can use it when you need to.

Mesh: [00:09:45] Yeah, it's very powerful. I'm on Twitter every day I think people do get scared of it who don't use it, who just immediately think it's a bunch of trolls in the basement who are out to get [00:10:00] you, and if you can curate it right,[00:10:01] it's very, very useful. I'm curious to hear  your point of view as a reporter, as a journalist, what are your thoughts on Twitter for breaking news or for news in general?

Alex Kantrowitz: [00:10:11] Well, actually it's a complicated answer, right? So it is a great place to figure out what's happening. It's a great place to interact with sources. It's a great place to test out opinions. It's a great place to test out [00:10:30] a story concept. Uh, it's a great place to hear when you're wrong. [00:10:34] On the other hand, I don't think journalists should write stories that play to Twitter. Right? I think they should write the truth. And Twitter incentivizes for engagement, not the truth. So I think that it can poison journalists’ brain a little bit and make them start thinking that this is the optimal way to engage and the optimal type of audience to write stories for. [00:10:55] There's an emerging and growing problem where journalists are starting to write their stories [00:11:00] for Twitter and not the general public. And Twitter and the general public are two different things, that value two different things. And it can skew what we see in the news. [00:11:08] And I think it's really a big issue. And I think it needs to be talked about more. And I think that only when we start to tackle it, are we going to get back to a more healthy news ecosystem than the one we have today.


Mesh VO: The news ecosystem has a long journey back from the past four years, which saw rabid misinformation and the destabilizing of long-trusted institutions. As consumers, we have a tendency to pile on and share, retweet and comment, before asking questions and knowing context. Alex is one of many writers who believes in keeping the public informed, whether or not it makes him popular. And by charging his subscribers directly, he’s hoping to be part of the movement that brings balance back.

To hear the rest of this interview, along with our other interviews from Season 3, become a Talk Money member at You’ll also get access to our Creator guide -- and use the code “podcast” for a 20% discount.

Talk Money is taking a short break, but we’ll be back soon with more stories on how the pandemic has changed the world of business -- for better or worse. If you haven’t already, subscribe to Talk Money to get all the latest updates.

This episode was produced by Olivia Briley and me, Mesh Lakhani. It was mixed by Valentino Rivera with help from Eduardo Perez, and featured music by Blue Dot Sessions. If you can, write us a review, it goes a long way and helps us get discovered. Please share this episode with your friends, and stay tuned on Apple Podcasts, Spotify, or wherever you choose to listen. Until next time.

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