The more successful people are, I feel like the less they feel the need to show how successful they are. They actually tend to be like pretty down to earth. And I felt, and this might be controversial to say, but I felt like Zuckerberg was down to earth.

This is the Techsploder podcast for Friday, May 17th, 2024. Alex Kantrowitz. This episode of the Techsploder podcast could not happen without the financial support of our wonderful patrons at patreon.com/JasonHowell. If you like what you hear, head on over and support us directly. And thank you for making independent podcasting possible. Hello and welcome to the Techsploder podcast.

I'm Jason Howell. It is great to be here with you talking just about the technology that unites us all and hopefully the passion that drives that interest in technology. That's really what this is about for me anyways.

I hope you can resonate with that. This week's conversation is a real treat for me. Alex Kantrowitz is my guest.

And Alex is someone who I've worked with a number of times over the last half decade while I was at TWiT primarily. First, while he was putting out tremendous reporting for BuzzFeed News. And later, as he fired up his own content business, Big Technology, where he produces multiple weekly podcasts now or episodes every week for the Big Technology podcast. And then he also has a fantastic newsletter, always top quality.

Anyways, you should check it out if you haven't already. Alex, in this interview, shares what it was like doing serious journalism for a site that was best known for listicles and clickbait meme content with BuzzFeed, their news department. I felt like they did amazing work, excellent work.

Alex really was the name that really jumped out for me, but they had a wonderful team. But it was within BuzzFeed. And I think that sometimes people looked at those two things and they didn't know how to negotiate between those two separate things.

They're very different. Also, Alex talks about how he approaches big interviews with technology's biggest names, including people like Mark Zuckerberg. What is it like to go into a room with someone like Zuckerberg and have a list of topics that you know you're going to breach with him and talk openly and from a relaxed perspective? And finally, many other things, but also how his career has been served, because this was a theme that continued to kind of bubble up, by his tendency to just ask for what he wants and hope for the best.

So that's all coming up in this interview. But before we get there, don't forget to like, rate, review, and subscribe wherever you happen to be. We really do appreciate it.

The show is very early, and so it all helps. And I want to call out Charles Hanskat, just one of many patrons of the work that I'm doing here with The Techsploder Podcast. You can actually support my work as well.

Just go to patreon.com/JasonHowell, and you too can have your name called out with deep appreciation by me at the top of the show. All right, let's get into it. Without further ado, this is my conversation with Alex Kantrowitz. Alex Kantrowitz, it is an honor to get the chance to talk to you so casually about technology. And I got to say, I produced This Week in Tech for the TWiT.tv network for a number of years. We've had so many guests throughout the years that kind of come through, and their work starts to bubble up to the top. And it's like, oh, wow, we should get that person on or whatever. And you are one of...

I don't know how to say this without it sounding weird. You are one of the guests that I'm most proud of bringing into the network. Because if my memory serves me, Megan Morrone and I were doing Tech News Weekly. It was either Tech News Weekly or Tech News Today for the TWiT.tv network. And we were just coming across your stories left, right, and center on BuzzFeed, and finally decided to start bringing you on, and you quickly became one of our favorite kind of interviews on that show. And then eventually, you know, Leo Laporte, he was always looking for new faces for TWiT. And I was like, well, it's a no-brainer. It's got to be Alex. He's amazing. So Alex, it's great to talk with you today.

It's great to be here. Thank you so much for bringing me on all those times. I really loved being part of your show and of Leo's show, and now of your new show. It's great to be here.

Yeah, yeah. And I mean, you know, the fun of this moment is, for me anyways, is that this show gives me the opportunity to talk with people like yourself, who so many times in the past, there's a very specific reason why we are having a conversation. It's this news story. It's this thing that you know so much about that you wrote a fantastic article about it.

And we're trying to hash things through. And I feel like the opportunity for this show for me is just a chance to get to know the people behind the byline on a more personal level that isn't so driven by the news itself. So that's why I love doing this show and love having the chance to have you here, because I feel like on one hand, I know you really well through your work. But on the other hand, there's so much I don't know about you.

And so that's why I like this. No, I love the idea for the show. It's really cool to be here. And I love the idea that we're going to talk, you know, not necessarily about what's happening, you know, in the news of the week, which can tell you some things, but to go like a little bit deeper, I guess, into the technology story itself, which is so fun. And I think it's fun to think about on a deeper level. So, you know, we talked a little bit about when would be a good time to come on. And it's very cool to be here. And one of the early episodes on the show.

Yeah, right on Alex. Well, thank you for your time. Where do we even begin here? I think, you know, in kind of getting ready for this conversation, of course, as I usually do is kind of going through sources online, just to kind of get a better sense of like, all right, there's the Alex that I know, there's the, you know, the BuzzFeed reporter for a number of years, now big technology, big technology podcast, newsletter, contributor to CNBC. So you're I mean, you are crazy busy. And not only that, like, I'm very new to this independent content creation game. And it wasn't that long ago that you broke out and kind of went in your own independent direction. But you're not you're not just like making it work. You're incredibly successful at this, at least from my perspective. How has the last handful of years been for you in creating this business and doing man doing such a bang up job of it?

Thank you. Well, look, on the successful part, like some days, it feels like everything is going right. But most days, it's like, oh, if you do so many things that says always something that's falling apart or something you wish you control better.

So but it is a lot of fun. As you mentioned, I was a reporter within newsrooms for many years, maybe seven or eight years, working within advertising age and big technology. And then four years ago this month in May 2020. I had been about a month out from my book release, I released a book on like the worst possible time in over a century, which was April 7 2020.

The first the first peak in COVID death in the US. And so the this book, which was all about the inner workings of the tech giants, which I thought was, you know, poised to do pretty well, was basically stillborn. And I had a decision to make, like, do I want to stay at BuzzFeed and keep, you know, being like one reporter among many working on stories that the publication needs and some that they'll take that I'll pitch? Or do I want to just go out on my own, keep writing about what I learned in the book, keep pursuing the relationships with editors that I had built as I was working to pitch excerpts and things like that, and see what happens as an independent reporter. And then it took about six weeks after I released that book for me to say, okay, I'm giving my notice. And so I gave notice, I was out at the end of May 2020. And then I think I had my first story up on big technology in July 2020. And then the podcast started in August 2020. So it all happened really fast.

And it's been amazing. I mean, I think what's great about being independent, is it allows me to really develop a voice with my newsletter, like my readers really know who I am and what I what I'm interested in and how I feel about things. Because instead of me, like, you know, filling holes every now and again in a publication, and, you know, writing about some of my beat companies, but basically what my editors thought were important, which was great, great practice, like now, and great experience. Now, I'm just like pursuing the stuff that I think is the most important story of the week. And that's enabled me to build a relationship with my audience, I just couldn't have done as one among many reporters inside a place like BuzzFeed News. And the podcast just takes that to a completely different level, where like, we do two episodes a week, one is a big flagship interview on Wednesday.

And the other is a news recap on Friday is just breaking down the week's news. And that is really like it's I think you know, this having worked at TWiTter so long and starting your company that the most intimate relationship you can have with an audience member is audio, because when you're you're doing a podcast, you're in people's ears. And you know, they you're like there as they're walking their dog or doing the dishes, none of the glamorous things, right. But these are like, very cool moments where like, people can really kind of sink in and, and experience, you know, the content that you're bringing forward and, and get a chance to know you, like, I'm sure you've seen this where people will come to you.

And they'll never say, you know, I've read your print articles, I feel like I know you, but they've been like, I listened to you on a podcast, I really feel like we know each other. And that is just so so cool. So it's a long answer. But basically, this path these past four years have been have been exceptional, just so much fun, so much learning for me to do in terms of how to run a business like this, how to create content like this, how to narrow down a lane that I'm interested in. And, and it's been an absolute blast. And I hope to do it for many more years to come.

Well, it seems like you've you've laid a really strong foundation to enable you to do it for many years to come. And the quality of your work has always been top notch.

That's what that's what pulled me into your writing. Because I, I wasn't as aware of you at Ad Age or Advertising Age. I always called it Ad Age. But is it Advertising Age?

Advertising Age is long. But yeah, people call it it's they basically call it Ad Age. Yeah.

Yeah, yeah. When you were at Ad Age, I may have, you know, come across your byline and not, you know, made the recollection. But at BuzzFeed, I definitely did. And what was so interesting to me about that, that moment in time, and I'm super curious to hear kind of your perspective on this is BuzzFeed was what BuzzFeed was at that moment, prior to there being a news department, BuzzFeed, to a certain degree, was kind of a punchline in and of itself, right? It was this website that was, you know, reveled in the listicle, and had what a lot of people would consider the opposite of like gravitas newsroom kind of aesthetic, right?

It was really like, here's a bunch of stuff that you you're gonna, you know, flip through when you're when you're, you know, on the toilet, in between things, you know, just like reading listicles and stuff like that. Yet, what really kind of drew me to your work, you know, the quality of your work, and then lining that up against the fact that, wait a minute, BuzzFeed's doing a news play here, and actually, it's super strong. And even then, you know, even with the quality of the work being as good as it was, still, I think the reputation of BuzzFeed, the other version, you know, was at odds with kind of the news version. And I don't know that if that was ever, ever a quality that the company was completely able to shake.

But I'm curious to hear your perspective. Because I mean, you were in there largely helping them develop that strong newsroom. And I thought you guys did an amazing job. What was it? What was your perspective? Now, now having some distance from it, I suppose.

Thanks. Yeah, it was a great ride. I mean, it was a place. So I so before I went into journalism, I actually spent three years in sales and marketing. And so I had to make my way from those jobs into journalism. And so it was obviously going to start freelance. And then I went to write about the advertising technology companies at AdAge. And while I was there, you know, we saw this new surge in new media. And that was the BuzzFeeds and the Vices and the Vox Medias, which now at the end of their many of their stories, it's been kind of sad to see what's happened, because they never really figured out a business model. But they basically said, you know, we're going to try to do this a little bit differently than a lot of the companies that are trying to make money on the web. And, you know, at the time, when I was trying to make my way into the industry, you had a company's like, I think fortune that we're having junior reporters write eight stories a day and business business insider writing eight stories a day. And I was just like, I just don't really want to do that.

I don't really want to I would leave my my sales job at the time to try to churn content out. And also, exactly. And so BuzzFeed, basically, I followed Ben Smith at Politico. And then I saw that he was going to BuzzFeed to become the editor in chief there. And I had like a little semblance sense of like what BuzzFeed was just by being in the New York media industry.

And I was like, oh, that's weird. And then Ben basically was like, our job as reporters is going to be to ship to write original stories. And original stories are what shares on the Internet.

And if we are able to deliver scoops and deliver new perspectives that people hadn't seen, we'll be much better off than those people that are doing like the, you know, treadmill of stories that are not undifferentiated and will be able to build an identity that way. And I was very attracted to that vision. And I applied. I met Ben at a meetup and he put me in touch with their tech editor at the time. And I was like, please hire me. And he's like, no, but I will publish one of your freelance stories, which was cool.

And then there was a business desk that was created. And I thought, oh, I have a chance to get into BuzzFeed this time. And I got all the way to reference check. And then one day I get a call from Ben and Ben goes, hey, Alex. I said, yeah. Hey, Ben.

He goes, Ben Smith from BuzzFeed. Do you speak Russian? And I was like, no. And he's like, oh, OK. For some reason, I thought you did.

OK, bye. And I didn't get the job. And like the context was that like this was around the time of the Boston bombings and the Sarnevs were like active on the Russian VK social network. And I think Ben thought that I spoke Russian so I could do a story for them. Anyway, I couldn't do that and I couldn't get the job.

So that was strike two. But I did do a couple of freelance stories for the business desk after that. And then finally, they created this desk in San Francisco.

And I was like, all right, I'm just taking one last swing here. So I emailed, cold emailed Matt Honan, who was the bureau chief there. And the subject line was I want in and was basically like, Matt, I know you've built a good team. I think I can contribute. Here are some things that I've written.

Here are the lanes that I play in. And what do you think? And then a month later, he goes, oh, this sounds good. Let's interview. So they hired me.

So my third time really was a charm there. And, and, and I did, I do think editorially, they really like lived the mission, which is that like, maybe up until the end, I really never had to do like, this is traffic for traffic sake type of content. And, and they really helped develop me as a reporter, both helped me with my writing, taught me really how to break news in a way that I didn't really know how to do beforehand, and then gave me the runway to write the stories, the big stories that I wanted to write.

And I think that's kind of where like, you and I started to, you know, get in touch was when like, I did get, you know, I got my legs underneath me, I did end up writing those stories. And I got a chance to travel, go to DC, things like that, when Zuckerberg had his hearing there, and then go to obviously, I moved to San Francisco for the job. So I got a chance to go down to Facebook headquarters, like almost every week or felt like that.

Met with Zuckerberg three times by the time I left. So it was like a just a very fast path into being a reporter that was covering meaningful stories for an art for news organization that that had reach. And let me just, you know, quickly touch on the first part of your, your question about like the seriousness of BuzzFeed. And I do think that they you're right, they never really completely shook how silly the website was.

And like how like, there was like, you know, so many, there was memes, and then there was real news on on the site. But for me personally, it was like a perfect place because we had so much reach. We were big enough that people would pick up the phone.

And it was a fun place to work. And I think that like we talked about like the gravitas journalism, and there's definitely a place for it. But coming from sales and marketing, I was never a journalist that took themselves too seriously, at least I hope not. And so like, it was fun for me to be like in a kind of like a silly, you know, new company with with with room for silliness, and levity. And, and to speak to readers who were interested in that. I think that was that was really good for me taught me how to read how to really write for the public versus for like a group of really rich people consuming niche news site. And I think that he's ethos still lives on for inside big technology.

Yeah, yeah, indeed. And well, and for sure, it sounds like from what you're saying, as far as your your ability, in in those years of being able to kind of learn within the walls of the company to become a better reporter to, to work within the access that you now suddenly have the ability to reach, you know, go to go to Facebook and interview Mark Zuckerberg. I mean, these are things that, you know, not everybody gets the opportunity to do. And this was a this was a place that really gave you the opportunity to do that. And to ultimately write your book, which, by the way, like I make no qualms about it, like, I don't know that I have a book in me, but I look at people who can organize their thoughts in a way that you can, you know, put together a start to finish book. And I just have immense respect and admiration for anyone who's able to kind of collect that information, and also organize around that. Because when I look at the the content of the book, and how many interviews you had to do to, you know, to paint the picture of your book, I mean, that take, how long did that take you to kind of collect all of that and, you know, reach it, you got it, you got to schedule all those interviews, you got to talk to all these people, you got to, you got to keep track of who's where and when. And I mean, it's just, it's just, it makes my brain hurt to try and put myself into your position doing that.

I was really, it was a thrill to work on as a beat reporter, because it gave me a chance to go so deep into one story versus like, kind of dip my toes into, you know, a story every day. That like, it ended up leading me to a much deeper understanding of how the big tech companies are able to operate. And I hope that's what the, you know, people who read the book get, get out of it, which is basically like, and it's kind of funny looking at it now. But my thesis is basically in that, in that book, look, the tech giants are operating in the future, they have technology in their workplaces that they have developed for themselves that you might get in five years. And so it's better to learn like the way that they've shifted the way that they work, the leadership, the technology, and the processes. So you'll be able to compete in the world versus get destroyed by them.

And it is wild. I mean, if you think about it, last century, the average company lasted 67 years on the S &P 500. This century, it's 15 years. And, and, you know, it goes to show you that like last, you know, 100 years ago, you would get one good idea, and you'd be on the S &P 500 for a lifetime. But now you need about three and a half to stay in the same in the same place. And so the book is called Always Day One, it's all about how the tech giants reinvent themselves, and use technology to make room for the ability to reinvent, and then to support that reinvention.

And there's a chapter each one on Amazon, and then one on Facebook, Google, Apple and Microsoft in that order. And it was very interesting to organize because I flew out to Seattle before I even had a deal. Like I took leave, I pitched to publishers. And I was like, I got this flight to Seattle, I got a place to stay, I'm going to be cat sitting out there. And I'm going to figure it out. And if you if you buy the book, I'll be in the right place at the right time and ready to go. And if you don't have a nice vacation in Seattle with a cat, but I hope you buy it. And so Penguin bought it, which was awesome.

And, and so what was cool is that it gave me this opportunity to just keep building on the questions, right? Building on the question of why are these companies able to stay so relevant, despite the fact that they're big and old. And usually this is when companies start falling apart. And every little bit that I learned in each within we're all working on each company's chapter allowed me to build and you know, learn a little bit more from the next one. And then I eventually kind of came to the end, went back to BuzzFeed and then took another month of leave to edit. And then I realized, oh, no, like I have to basically rewrite a good chunk of this because some of the things that were apparent by the Microsoft chapter made no sense in the in the beginning. So it was basically like, alright, let's write it through and get it out.

And, and it was just an awesome, it was an awesome process. I think a lot of the things in the book hold up. We looked a lot at artificial intelligence and how AI changes work. And so it's been really good grounding for like people in the workplace today thinking about how AI might change their lives and change their jobs. Like you already see it inside Amazon that, you know, the question of replace us or augment us and how will it change work? Like Amazon has been working on augmenting the vendor managers and its retail program for a decade and it's largely done it. And so following the path of the people that have been within Amazon tells you a lot about where, where things are going to go in our jobs as you know, things like open AI technology goes deeper into the workplace.

Yeah, it really is. This moment where AI is really feels like it's, it has such influence in shaping and reshaping the technology that we're used to really seems to be the core message of exactly what you were writing about in the book, this, this reinvention. And I mean, this year, especially the year 2024, the year of AI, where every company and their dog are coming out with, here's how we are, you know, how we are not only doubling down, but putting our, you know, overall emphasis and focus on the revitalization of what we offer with AI at its core.

And that, that seems to be a big, you know, a big, I don't know, symbol of, of what you were writing about to begin with. And they're all following the same play playbook right now, it seems.

Yeah, absolutely. I mean, this, we're right now, we're kind of in that moment where it's like, all right, well, that stuff that was available within the big tech companies a couple of years ago, it's now really being made available to the broader economy, largely by the big tech companies. So it's kind of an interesting thing where like they've eaten their dog food and now they're serving it to you. And so what are you going to do? And that's kind of what the book was about.

Yeah, yeah, indeed. You've, you've talked to a lot of, you know, very big names in technology. We already talked about Mark Zuckerberg, Larry Ellison, Jack Dorsey. And I, you know, I've, I've interviewed people of, you know, of a certain caliber, but I've definitely never interviewed people of that caliber. And one, one thing that I've always wondered, you know, coming from the perspective of the art of the interview, when you are in the room with someone that has so much influence, so like, you know, they're of that caliber that pretty much anything they do is newsworthy or noteworthy depending on who happens to be in the room noticing it at the time. Does that like, does that change the oxygen in the air when you're the person asking the questions, talking with them about this stuff?

Or are you just at this point, I mean, I don't know, at this point, are you just so studied and so well rehearsed and, and used to it that it doesn't influence your ability? And the only reason I bring this up, and this is just one of those things that I'm super embarrassed about, but hey, we are who we are, is way back when I was at Google IO and Matias Duarte was the guy who kind of rolled out the very first iteration of material design for Android. And that was kind of a big deal at the time.

Android was, you know, a little, a little stale in the design department. And now Matias Duarte, very, you know, very stylish, very flamboyant. You know, so you, you watch an interview with him and you're like, who is that guy?

Like, he just has an energy to him. And I found myself in a room with him and I was stunted. Like I had no idea how to talk to this guy. And I really wanted to pull myself out of it and have a really smart kind of interesting conversation with him. But I couldn't get past the feeling that I had that the oxygen was just different, that he was on a different plane than I was in that moment. I'm just always curious, like when you talk to Mark Zuckerberg, do you ever feel that? And if you do, like, how do you pull yourself out of that?

Yeah. With Mark, not really. And, and I, I'll tell you why I kind of think that like, we're two people who like, when I'm in the room, this is what I'm thinking. We're two people who are deeply interested in the same things and just coming at it from different angles. And, you know, I think that like, that is, that's pretty cool. And I think that this is like the stuff that he knows best. And so I'm going to ask him about it. And we might get into interesting places because the questions that I'm asking are going to be pretty different from the questions that he might face elsewhere. And the other thing that I do before I go into an interview like this is I, I mean, of course there are going to be open-ended questions that I'm going to ask, but like, when I'm meeting with Zuckerberg, I'm not like, going to be like, what's your philosophy on leadership? And how do you lead this company? I want to come in.

I almost report out the interviews before I go in. So I had some fun, like speaking with people who've interacted with Zuckerberg and gave me their impressions of him and, or told me about specific interactions with him. And then I go in and I'm like, all right, I want to know like what you were thinking in this interaction. And that like, is a really like interesting way to like, broaden out and like take a CEO is going to like be on talking points.

And it's like much more difficult to be on talking points. If you have to speak about a certain situation, I'll tell you one story. I was speaking with this really young product manager that Facebook had brought in to help them think about the way to build products for young people. And he told me that Zuckerberg is always interested in trying competitor products and trying products out that you know, he's thinking about building and did not have this only invented here mentality. And in fact, he talked about how like, he effectively taught Mark Zuckerberg how to use Snapchat, and would like criticize him when Zuckerberg thought he was doing a meme, but like, he actually was getting it wrong.

And it's like, No, Mark, this isn't how it works at all. And so I like brought that up in our conversation to be like, you know, tell me like a little bit about like how you use Snapchat. And then Zuckerberg, like initially was like, well, I like to use everything. And I was like, but Snapchat in specific. And, you know, that led to even more interesting story where he's like, well, let me tell you, we were, we were building the Facebook dating product. And he's like, well, I have to get on some dating apps to try to figure out how these how the UI works. And so you went on a handful of them. And I was like, Wait, you used your real photo? And he goes, Yes.

Okay. And he said, I was on one of these apps, where they serve you like one match a day. And you decide whether you want to go out with them or not. And I was showing it to he's like, I was showing it to Priscilla, his wife. He goes, Hey, check this out.

This is like a pretty cool app. And Priscilla looked at the woman that it served up to Zuckerberg, and was actually a friend of hers. And she was scheduled to go to lunch with her the next day.

Wow, must have been a fun conversation. So I know that you saw Mark on I don't know what it may be hinge or something yesterday that was just for research. Just just to be clear. Yeah, just to be clear. So so it isn't I think there are some ways to go into these rooms and just to be like, all right, this is going to be this is going to be I, I definitely want to give them a different interview than they're going to get elsewhere.

For sure. And that that is so I'll do like, you know, more, you know, like hours of interview work before I go in, just to be like, All right, you know, now I'm here. And now I have a set of things to talk about versus like, you know, what's your theory on social media? And that's helped a lot. Mm hmm.

Yeah, no, that that makes a lot of sense. I think, yeah, really kind of breaking down the barrier that makes, at least in my mind, that that would make me feel like they are unattainable, or of a different caliber, different level, and breaking that down to a point to where we can just kind of realize, like, actually, at the core of it, they are also just another human being that is doing, you know, doing the best that they can, given the cards they're dealt. And actually, in many cases, with some of these people, they're dealt some pretty, pretty great cards. But yeah, and, you know, running a company, just like other people run companies, it's just their company happens to be a massive, you know, tech, tech giant company.

Also, like the more successful people are, I feel like the less they feel the need to show how successful they are. They actually tend to be like pretty down to earth. And I felt I and this might be controversial to say, but I felt like Zuckerberg was down to earth, and like, very approachable. Yeah, yeah.

In the work that you did for your book, and kind of learning how the these technology companies continue to reinvent themselves, and the impact that that has on the business that they're creating. And, you know, obviously, you know, these are companies that are not hurting when it comes to being successful in the industry that they that they reside. How has that? How has that made an impact on your own business? Now, granted, you're not making phones, you're not making smartphones, or, you know, tech products, necessarily. But do you do own, you know, you are operating your own company that operates in the world of technology. And I'm sure there are some lessons that, you know, you've been able to kind of extract from them and kind of apply to your own scenario. Is there anything that comes to mind there?

Definitely test and fail fast, I think is important. Just getting out there trying different things, and not being like, this is what I do, I'm sticking to what I do.

So I've definitely had that sort of, I mean, day one mentality inside big technology, right? Like, okay, try the newsletter, try the podcast podcast is going well, there are some episodes that we talk about the news on that perform even better than the others. And so like, let's just do another news episode on Fridays and see how that feels. Now, I was telling you before we started that I have my first live event or public event.

We had one private event last year, but we have a public event in New York this week. And you know, I'm trying to learn how to like I was talking to you trying to learn how to do the audio for that, right? And see what the response is going to be. And I think it's pretty cool.

We are like beyond sold out at this point. It's like a tech talk with Aaron Levy, that's going to be on the big technology podcast feed. So that might be a new, a new place to for me to check things out on. And then so I think like really just test testing and seeing what works being open to conversations. And then and then be profitable, right? Like, you know, it's important.

The year of efficiency for Facebook might have been last year, the it's been the lifetime of efficiency for big technology. So I'm trying to like, grow. My growth path is very different from them.

Right? I try to grow brick by brick, listener by listener, viewer by viewer, reader by reader. And I think as long as I do that, I'm in it for the long haul, then I'm going to be in good shape. And there will be no IPO of big technology. So that's totally fine.

Yeah, yeah, interesting. I was not kind of leading up to this conversation, you know, I obviously, as I usually do, as it sounds like, you know, of course, you do leading up to an interview or a talk with someone, kind of, kind of, you know, following the the breadcrumb trails online to try and get a better sense of the things I already know about you. And then things that I wasn't too familiar with, prior to Ad Age and prior to BuzzFeed, and everything that you're doing with big technology, you were more in the I would say the political realm, how, how like, and which I mean, and granted, technology and politics, they overlap pretty significantly. So that sets you up with a very, strong skill set to be able to analyze what you do today, it's probably a large part of why you're so successful at what you do. But how like, do you find more joy in the technology coverage side of things compared to the political side of things? How did that all shake up? And why did you switch from one to the other? I'm just curious.

Yeah. So I'll just answer the, well, the joy question first. And then I can go a little bit into the story. Yes, definitely. I find way much way more joy in technology than I did in politics. And I feel like technology is really about helping build things, build things and go forward.

And technology oftentimes is about small mindedness and, you know, and, and, you know, petty fights, and I did not enjoy it. So I did like, two, well, I'll say that there were two phases of like the work that I did in politics and government, there was a politics phase, and there was a government phase. So and of course, government is interlinked with politics, but like the actual work of, you know, working in a government to sort of pursue the, the goals of an administration is very different than like the campaign work. And, and I thought government work was super rewarding.

And I did two, basically two things. One was, I worked for New York City's Economic Development Corporation. For a couple years, I was in the marketing department, but it was just very cool to see like, this was in Mayor Bloomberg's, you know, third term, just like, it was very cool to see like how his plans for the city came together. And like how we were charged with like putting them into action.

It was a very interesting agency to be in. And it's done everything from like the High Line to the Coney Island redevelopment in New York. And also like lots of like redevelopment of vacant lots that were just sitting there and owned by the city. And like, the city was just doing nothing with them because they were real estate assets that it owned. And like the, under Bloomberg, this, this agency tried to figure out like things to do with them that were productive. And then finally, they also helped build this applied science school in Roosevelt Island, which is like, I think a marquee achievement of the Bloomberg administration.

So that was pretty cool. Then I did some pure politics, like some campaign work in Queens when I came out of school, because I was coming out of school in the middle of the great recession and there were no jobs. And with politics, I was like, okay, like you won't get paid very much or anything at all, but you can at least do meaningful work. So I ended up working for this state assembly campaign. I was the campaign manager after this person saw me working for another, another petitioning drive. Like this was like the worst of Queens politics. Anyway, not a nice guy. And he ended up winning, but I was like, all right, I do not want to work with him anymore.

And also before that, so this is kind of where it both blends. I was, and this is really embarrassing to talk about, but I was an intern in Anthony Wiener's district office.

For those who don't know. At the time for the, for the whole Anthony Wiener scandal?

Before. Before, okay. For the, and yeah, he had a big scandal for those who don't know. It's, yeah, you can Google it if you want. I mean, I'll tell you the joke that I make, which is not true, is that I taught him how to use TWiTter and he paid attention to the, the tweet and the notification, but not the direct message. And that's where he ended up messing himself up with this DM fail.

But anyway, that's, yeah, I should stay away from that. But anyway, it was, it was, it was cool work because we worked in the district office and we, I would, I did casework for them. Like it was a real meaningful internship and like people would call up and there would be moments where the government was screwing them. And in a democracy, like your representative is like your last, your last line of defense against the machine. And we would actually go in and help people with things that the government was not. Like there was this one moment, this one day, I can't even, I can't even believe it happened.

It was such a cool thing to do as like an 18 or 19 year old. But there was a woman who was living in public housing and there were bedbugs there in their apartment. And she had an aid and the, the housing authority would not fumigate it until like they were ready to, to until their next opening, which was six weeks later. And the aid was like, I'm leaving unless there are no more bedbugs here. So this elderly woman was literally about to lose her health aid because of this. And we called the city's housing authority and we're like, listen, like we represent this woman. And is there anything you can do to make sure that she keeps her, her homemade? And they sent an exterminator and they got the bedbugs out and the woman kept her aid. And that is like some of the most amazing stuff that gets overlooked in all this coverage of like throw out the house speaker and who's going to win and who's going to lose.

Like we never talk about that stuff, but it is actually like a very cool thing that the government can do. But yeah, basically after the, the, the full experience there you know, of course, Anthony ended up like losing his seat. And then I think going to prison because of his you know, sex weirdness addiction. And and I mean, basically I think he was tech. I don't want to say exactly.

I don't want to get sued, but you can know, Google it. And then this guy who I met who was after afterwards, who was like not a good person. Like there's a lot of people there who it's ego first, not constituents first.

And that's, that's terrible. But overall, it was, it was a pretty instructive and important time for me in my life because I learned marketing, I learned government and, and then eventually you're right. Tech became political. And I found myself back in Washington, DC watching Zuckerberg testify, you know, after all this stuff that happened with their data scandals and things like that. And that, that was a real interesting full circle moment. Yeah.

Well, and, and you know, that early history as, as is often the case, that early history really set you up in a way to make you as good at what you do now, as you know, as could have been simply having that, that perspective and that experience to be that close to how government operates and that kind of the political side of things. And then to see big tech, you know, become such a political hot button issue, especially now in the war, you know, in this kind of current moment of AI infused with everything. And everybody seems to be scrambling to understand like, well, do we regulate, do we, you know, do, do we put these, these guardrails into place so that these things aren't possible or aren't capable of doing these things?

Or do we, you know, allow these things to develop and become something before we step in and intervene? Um, it's really an interesting kind of convergence of, of politics and technology and continues to be, I, I enjoy with, with these conversations getting a, you know, yes, a sense of who you are now, but also an understanding of kind of the, the very beginnings of this. And one thing that I like to ask just because I'm, I'm big into nostalgia. I love nostalgia when it comes to technology and music and all these kinds of things is that I can look back in my life and I can, you know, kind of identify certain moments from when I was younger that really lit the fire for me when it comes to technology and what I do now. And, I'm just kind of curious, like, you know, given that, is there something that when you reflect backwards into your life, is there a moment, a time, a technology, something that you can identify as a part of that fire that that was lit and that led you to what you're doing right now?

Yeah. I mean, so I definitely have always been into journalism and always been into technology. Um, man, I mean, I wrote a newspaper for my block when I was a kid and would like interview my neighbors and like drop off, like printed copies of it. when I was, when I was like, in my youth, I took an HTML class that like a local community college offered and it was H H T HTML.

Yeah. Computer, some website building thing. And that was pretty neat and would make these like websites on geo cities, which like, thank the Lord are no longer on the internet.

But I also kind of want them to be on the internet, you know, just to go look and remember just how bad they usually were. They were terrible, especially in retrospect. Yeah.

And, and then I also did this, um, there was a, at the same community college, actually, they had a radio station and they had a sports show that I listened to and thought was pretty good. And I wrote to, Oh, I called them up and said, Hey, can I be on your show? And they're like, sure, we'll find room for you. And so like, I was like at a time for a time, like a third co-host and for a time, a producer of the show. And I got the head coach of the New York jets to come on as a guest, which was super cool. Yeah.

That's a big deal. How old were you when, when this was happening? 15, man, that's a, that's an accomplishment. You know, you know what that tells me about you? You obviously are very good at recognizing that sometimes just waiting for something to happen, waiting for an opportunity, isn't going to get you nearly as far, just kind of sticking your neck out and going, Hey, you want to do this thing?

And you know, the worst thing that can happen is that someone says no, or doesn't say anything at all. But I mean, that seems in our conversation, that, that right there, your ability to do that seems to have led to a lot of things in your life. And that's really, that's really respectable.

Yeah. It was pretty cool. I mean, there was one time where like, you know, they, nobody showed up except for me and the sound engineer, this was a live radio station, by the way, this was like literally, but of course it was a community college. And he's right. So these, these people had all those things going on in their life. And I looked at the sound engineer and the sound engineer, like looked at me and I was like, and I was like, well, I have the daily news here. I think I could do a show. And she's like, well, if you want to do the show, you can do the show. And we did a two hour show.

I did it solo. And that was crazy. That was legitimately crazy. That was pretty cool.

Um, but, but going back to your point, like you are, you are totally right. And I was listening to bits of Jerry Seinfeld's, Duke commencement. And usually these things are cringe and they offer like the same advice all the time.

Um, but this one was, this one was pretty cool. Um, and Jerry was like, listen, he goes, you would all be amazed at, um, how, how much more important it is to swing than to actually have like, you know, your eye on the ball, just give it a shot. And even if you don't have any idea, um, what you're doing, like you're much better off than waiting for like the perfect opportunity. And it really is a true thing. It really is true. The perfect is the enemy of the good and doing is better than not.

What a wonderful way to end this. Um, Alex Kantrowitz, it's, it's been an, a real privilege getting to know you, um, as we have over the last handful of years, bringing you on the shows and, just kind of watching your, your star rise. Cause I really think you're, you're obviously you're doing a lot of things right. You're wicked smart. And, yeah, I just, I enjoy your work.

So, and I also enjoy you on a personal level. So thank you for taking some time to talk with me right before open AI's big announcement, coming up here about how it's going to change search and all that kind of stuff, which we'll both be, covering respectively. But Alex, um, where, where do you want to point people to, where should people go to, to find the things they need to know about big technology and everything else?

Yeah, I would say big technology podcast is a good place to go. And I also have a YouTube channel. It's Alex Kantrowitz. And I would say those are two good places to hang out, but thank you for having me on. And I will say the same about you, Jason. It's great to, you know, great to know you. Great to get a chance to speak with you every now and again. And I just want to say, I admire the project that you're working on now, and it's cool to see you out on your own and, and, giving this a shot. And it's so cool.

I watch your lives every now and again, and you have a pretty good audience, a lot of people tuned in and, I think that's awesome. So keep it up. Thank you.

Thank you, Alex, all the best. And, we'll talk with you soon. All right. Big thank you to our guest, Alex Kantrowitz. Alex is excellent. I look forward to my opportunities to working with him in the future. As for this show, we could not do this podcast without your support.

That much is true. The most direct way to support us right now is at the Patreon. Go to patreon.com/JasonHowell.

There, if you take a look, you'll see, we offer ad free shows, early access to videos, a discord community, regular hangouts and Q and A's with me. And one of the newest perks is being able at a certain tier level, being able to watch live as these interviews are recorded in advance. And so not everybody has access to that live recording.

Everybody has access to the edited version once it's all done. But if you want to be there while we're recording things, and you can even possibly ask questions during those episodes, then, you know, head over to patreon.com/JasonHowell. We also offer the chance to be an executive producer of this show, which I just deeply appreciate.

This week's executive producers, Jeffrey Marraccini, John Kuehne, Catie Lake and Bill Rutter. You're all awesome. Although anyone supporting me with this show on Patreon is awesome. Thank you, in particular, for supporting this independent podcast.

It really goes a long way. Techsploder records, you know, each week when we can, like I said, we'll share that live recording schedule with you if you are a patron, so you can join us there. But you can bank on new Techsploder episodes releasing every Friday, 10 a.m. Pacific, 1 p.m. Eastern. You can find the video version on the Techsploder YouTube channel, the audio version you can find anywhere that you get your audio podcasts. So just search for Techsploder podcast, you'll find it. And again, don't forget to like, rate, review and subscribe wherever you happen to be. That's going to raise the view and visibility of this podcast. And really, you can find everything you need to know about this show at Techsploder.com. Thanks again to our guest, Alex Kantrowicz. Thanks to you for watching and listening. I'm Jason Howell. We'll see you next time on another episode of the Techsploder podcast. Bye, everybody.

Alex Kantrowitz

Founder, Journalist, Podcaster - Big Technology

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