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  • Writer's pictureValue Creation

088: Boston Speaks Up with Alex Kantrowitz of Big Technology

Updated: Apr 28, 2023

Boston Speaks Up (BSU) is a podcast owned and operated by Value Creation Labs. Listen to BSU on any podcast platform you choose: SoundCloud, Spotify, Apple Podcasts, Stitcher, and Google Play.

Alex Kantrowitz is the founder of Big Technology, a combo newsletter-podcast news operation analyzing the systems in the tech world that drive what we see in the headlines. He launched Big Technology on the back of his wildly successful book Always Day One, which gives a behind-the-scenes view into how Amazon, Facebook, Google, and Microsoft have “stayed on top” by operating in Day One: Instead of hunkering down and protecting core advantages, they reinvent constantly.

Kantrowitz most recently served as senior technology reporter at Buzzfeed, and he regularly appears on CNBC to break down the news surrounding the tech giants. He penned the Tech Giant Update newsletter at BuzzFeed. In that role, he fell in love with the back and forth with readers, and found that the live replies with his audience were incredibly heartfelt and informative. It then comes as no surprise that he’s now made a newsletter his de facto journalism format.

Prior to Buzzfeed, Kantrowitz spent time writing for Forbes and Ad Age. He reported on marketing technology at Ad Age, which gives him a really interesting perspective at the intersection of technology disruption with advertising and commerce.

He studied at Cornell University where he wrote for the Cornell Daily Sun and co-hosted WVBR's Weekend Pulse. His radio background shines in his Big Technology podcast and furthermore when he appears as a guest on shows such as his appearance here on Boston Speaks Up.

In this episode, we discuss with Kantrowitz his journey to starting Big Technology, his modern media business monetization model, recent news such as the spiral of Silicon Valley Bank, his time in Seattle working on Always Day One, the impact of AI, the future of Big Tech, and much more.

You can listen to our podcast discussion embedded below or on any podcast platform you prefer (SoundCloud, Spotify, Apple Podcasts, Stitcher, and Google Play):

Before we get into the written Q&A, here’s a teaser clip from the episode:

Written Q&A:

Where did you grow up? And how would you describe your childhood?

I grew up in Long Island, New York and had a fairly ordinary childhood. I was raised in an environment where I was encouraged to question everything around me, which I’d be happy to dive deeper into when we chat live.

Who were your role models growing up?

As a huge sports fanatic and lifelong New York Jets fan, my role models at the time were probably Bill Parcells and Rex Ryan.

If you could go back and give your 18-year-old self one piece of advice, what would it be?

I think that when you’re younger you don’t fully appreciate how so much of society is telling you what you can’t do, and because so many people listen to the noise, the actual amount of people going after what's possible is limited to a pretty small pool. So my advice would be that what seems impossible, is actually quite possible. Don't let yourself be held back by what people are telling you that you can't do. It took me a while to figure out those lessons.

What is the biggest challenge you had to overcome to get to where you are today?

Like most millennials, we came up in an environment that’s actually been unforgiving since we've gotten into the workforce. We graduated in the middle of the 2009 recession. Then, right when things started to get better and we were all starting our careers, we got hit with COVID. It's just been challenge after challenge and there's never really been a “calm period of time” in the workplace, and in our lives for that matter.

What was the impetus for writing Always Day One?

I had been reporting on the tech giants for quite some time and they had been through a lot of turbulence. I felt like we were always chasing what was going wrong, which was a lot. But one thing that stuck out was that these companies that just kept growing bigger as they got older, and typically, when you get bigger, you start to fall apart, but that was not happening here. I started to think, “what was going on inside these companies that allowed them to be able to defy convention?” The more I looked at it, the more I saw that they had very unique cultures. They had cultures that emphasized invention and reinvention in a way that you don't see often in the rest of the economy. And they had used technology to their advantage. They specifically used AI as they had access to some of the most advanced AI research labs, and they were using AI in the workplace in ways that others were not. Once I put this all together, it didn't really fit inside a normal news story. It felt like it had to be told in a broader way, and that was when I thought I had to write a book about it.

Describe your book writing journey. What was it like immersing yourself in the Seattle tech community?

Writing the book was definitely the most satisfying professional experience I've ever had. It was difficult, when writing a book you have to make 20-30 calls for every little piece of information that you want to include. You learn some amazing things when you start calling people and asking these same questions. You get much more sophisticated in your question asking because you aren't coming in cold anymore, like you are in most stories. Things compounded and some of the deepest conversations I've ever had in my reporting career happened while writing that book. Immersing myself in the Seattle tech community was awesome. I am very appreciative of your help and helping me really get introduced there. Amazon and Microsoft just work differently from the companies in Silicon Valley. They're pretty fascinating companies and their alumni are also quite interesting. They have a work ethic and have been around longer than the Facebook's and Twitter's of the world, which are the companies I'd been reporting, so it almost felt like a much more mature version of tech that I was used to.

Who is the most challenging person you’ve interviewed and why?

The most challenging person I've ever interviewed was Mark Zuckerberg. It's interesting speaking with Mark because he is so well versed in so many different areas of the tech world. He is obviously well versed in AI, but he’s also well-versed in politics, media, advertising, sociology, you can really take the conversation anywhere with him and get pretty deep in any of those disciplines. So, when you only have 45 minutes to an hour, you have to be pretty precise in your question asking. It was definitely a fun interview, but it was not easy to get it right.

What are some of the challenges you face running your own newsletter + podcast and working for yourself?

The biggest challenge is scaling time and finding a way to be efficient in the way that I work.

What is one thing you think people misunderstand about you? What do you wish they could know?

I feel like I'm a pretty well understood person, I don't think I'm that complicated. So maybe if you pry a little bit, you can get a better answer out of me on that one.

Can you share your developing point-of-view on OpenAI/ChatGPT – and the potential good, bad and ugly?

I think that this is going to be a real transformational technology, that's my perspective on it. Chatting with Bing in particular has been pretty fascinating and I think that this is going to be a distributed technology, rather than a more than a concentrated one in the hands of few. Once these API's make their way into the public we’ll start to see startups use them for all sorts of purposes. Unfortunately, we now have the potential for these bots to start to manipulate folks. This will be something to watch out for, but I also think we're going to develop a sense of immunity against them, understanding what they do and how they might be trying to influence us. I don't think people are that influenceable that if a button tells them to jump off a bridge they'll do it, at least I hope not!

Who benefits from the SVB collapse? Bigger banks? Crypto/decentralized finance?

The bigger banks will definitely be the ones benefiting from this, but I don’t think crypto benefits from it all.

Where do you see Big Tech changing the most 5 years from now?

I do think that AI is going to be a real challenge for them. You already see what's happening with Google, that's a pretty big issue. If they can adapt well, then they're going to be in good shape. If they can't, we could see some serious disruption for these companies, the way that you haven't in quite some time.

Will Meta’s metaverse bet pay off? And how long might it take?

I think Meta’s metaverse bet will pay off, but the question is, was the magnitude of the bet worth making? Changing the name of the company to Meta is pretty bold, and so to do that, you need it to really pay off in that magnitude. You really need it to become the next operating system. Maybe it's not the next operating system, maybe it's just an enterprise play at first. In all honesty, it could take 20 years for this dream to become a reality. I definitely understand why he Zuckerberg decided that this was a bet that needed to be taken, but it's going to be a while.

Where, if at all, is Amazon most vulnerable to losing ecommerce market share?

They seem to be pretty well positioned. Shopify has a pretty good challenge to them in terms of the third-party marketplace, but that's questionable in terms of where it goes. In the near term, the real challenge for Amazon is going to be getting its costs under control and trying to survive the next five years, and if they can, they’re going to be really well positioned for the long term.

Let’s get deep for this one… If you could be remembered for one thing in life, what would it be?

Being good to people. If I can be remembered as being good to people, then that’s good enough for me.

FINAL QUESTION: We like the idea of ending our episodes with a challenge for the listeners/readers. Whether it be reaching out to an old friend, reading 5 pages a day from a book, creating a new healthy habit… What is one challenge you have for the listeners?

Read the articles on social media before you comment on them.


You can follow BSU on Twitter at @BostonSpeaksUp, and recommend BSU guests by contacting

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