The Exchanges

Q as, of Wirecutter today is, um, reviewer or reviewers, they, they really put like five, six, maybe 10 different, um, brands of, of a product, a TV, or a washing machine, or a coffee traveler mug, or whatever, to the test. And they really, really run them through, you know, try them out in different places, and, and then they basically pick one. Was that the model at the beginning?

A That was the model at the beginning, but very quickly, it evolved into a mutant form of that, which was way more powerful. Like, for example, if you review 20 headphones, normally on the internet, before Wirecutter, you had thousands of opinions on headphones that were subjective, and maybe you had a few people who were professionals who would Objectively record things. So we had a process that involved both of those things and a blind test with musicians, audio engineers, and surprisingly, most of those people would agree on which one sounded better blindly. So even though it's a subjective thing with enough process, you can make it a little bit more objective. And here's the thing that makes it even cooler. Now that you've got the top two or three, the next time you can introduce another 40, and you don't have to compare the new 50 to the previous 50, you just have to compare it to the current kings of the hill and see if they get dethroned. You now have tested a total of 100. And so as you work on this evergreen article with updates over A decade now, it's probably hundreds, if not over a thousand headphones that get tested.

AI assessment note: “That was the model at the beginning, but very quickly, it evolved”

Q I mean, it was still like early, it was like going to a pod, it was like me going to a podcast in 2011 leaving radio. People were like, what are you doing? That's, who listens to podcasts? That's, that's, that's, What are you, crazy? You're leaving the radio? That was kind of the reaction, right? That when you decide to leave Wired and go work at Gizmodo in 2006.

A Yeah. San Francisco media is like, it was like Simple Made at the time, and it was Wired, right? So it was just one Condé Nast magazine. People don't leave that place. People stay 1020 years longer, and I probably was the first Condé Nast employee to leave for a blog. Blogs were so rudimentary at the time, but when we were doing front of book stuff to find gadgets for, uh, Wired, People around me were like, yeah, just check out Gizmodo and just find, find leads there. I was like, okay, we're just basically getting leads from blogs. We're not like going to find new stuff. So I decided to work there because I felt like I could have impact there and control over the editorial.

AI assessment note: “People don't leave that place. People stay 1020 years longer”

Q And by the way, when you, when you launched Wirecutter, did you think this could make a lot of money? Or did you think, I know it can be sustainable? I know it can sustain a, a team of people or both.

A I was so obsessed with just doing this service, and like, say, taking a two-hour shopping experience and making it a 32nd shopping experience with the lead containing the thing we thought you should get. I thought it was such a great idea that didn't exist. I was not at all sure of how we were going to make money, ever. But I also wanted to grow things really slowly, because I was so burnt out for the first year, I could only basically work 10 hours a week. And I think my partners must've been like, you're only going to publish one article every three weeks. And I said, yep. And I knew that if you projected that over a couple of years, you'd have like a hundred articles that were evergreen. But that cadence is so alien to media, and to investors, and to the public. But I knew working at Gawker, where we were doing so much quantity of news that would become basically useless tomorrow, it was a good use of time.

AI assessment note: “I was not at all sure of how we were going to make money, ever.”

Q at a PC magazine, Maximum PC, but how, before we get to, to, to that internship, how did you even start to think about, because you did some journalism in college, but how did you start to think about like, okay, I gotta, I gotta try something else. I gotta do something else. What, what was the, what was the catalyst that led you to start to think about that?

A Fear. I mean, I, I feel like I have to depend on myself. But, um, ok so my family does ok, right? My grandpa did great, and all my aunts and uncles pretty much live off my grandpa, what he did. And I remember this one time at dinner, my grandpa was really grisly, and he was gruff. He'd been through a lot, and he made it happen, and we have a, we had a very good relationship while he was alive. And I remember him looking around at all my, like, aunts and uncles, and they were, like, kind of squabbling, and, you know, they act like they have no consequence in the world. They're really, like, happy-go-lucky, right? And I remember my grandpa, and he looked over at me, and he let out his huge sigh, and he was like, there's a saying, right? It takes three generations to lose a fortune. And I just remember that moment. And I remember looking around and I'm like, I don't really want to, I don't want to be like my aunts and uncles. I want to like do something with all my heart and make a living and, and support my loved ones in a very just, you know, basic way. Uh, but in my own style. And I think I always had that in the back of my mind. Well, I'm pretty smart, and my brain is worth something, and I'm basically getting punched all the time in the head. So it just didn't seem like it was going to go anywhere, and four years is a lot of time, and the economy was starting to recover, and …

AI assessment note: “Fear. I mean, I, I feel like I have to depend on myself.”

Q Why? Just, there was just not enough information, or there just wasn't a good place that was giving advice?

A The, the information is out there. On the tip of the tongues of the editors covering those beats. But the formats that were common in the business models attached to them encourage you to click on, like, 40 different articles about, say, TVs, for example. And then you have to compare all of them and their prices and their features and decide which one's right for you. And that's a lot of work, or a little work if you don't care, but it's a lot of math. It's a lot of just, you have to figure it out. Mm-hmm. And every major publication at the time would do that. They would just force you to sort through dozens and dozens of reviews, or look at a huge chart full of like circles and dots that don't really mean anything.

AI assessment note: “The, the information is out there... But the formats that were common”

Q Do you remember what you were interested in when you were in high school? Because I know you, you would go on to Boston University and Kind of experiment with different majors, um, jump from different one to another to another, but did you have a sense, like, of what you thought you wanted to do when, when you left for college?

A Yeah, so I switched, right, I switched from, like, I think, I think it was, like, philosophy, English, computer science, journalism, and then I ended up in business school. Hmm. But the only class I enjoyed was the strategy game, and it was like this rudimentary networked thing where it's like you're in the sneaker industry and you like choose which factories and what pricing and the quantity you want to produce. And I think I beat like a couple hundred kids at that. Got super aggressive on pricing. I basically was like cutthroat business person long-term thinking right away. And I would like undercut them by like two pennies and like win that week, and I just kept winning, winning, winning.

AI assessment note: “I switched from, like, I think, I think it was, like, philosophy, English”