So tell me a bit about your early years and where you come from.

I was born in New York. My mom and dad lived in a bad neighborhood and then I think my dad caught someone pulling a TV, their TV out of their apartment at one point, and then they decided to move to the suburbs.

The suburbs are what? Only 30 miles away from where they were in New York, but it’s a world apart. It’s really the kind of place where someone like me can grow up, and just not quite fit in. I think that was really important to my development, because it got me really used to thinking for myself. That’s been really the most satisfying thirty-something-year arc in my life going from public schools in New Jersey, all the way to corporate publishing jobs to doing my own things that are weird and special in their own way and loved for that. That’s been a really big trend in my life, just that feeling of not quite agreeing with the crowd. I started understanding that in New Jersey.

“That’s been a really big trend in my life, just that feeling of not quite agreeing with the crowd.”

What was it like? You are first-generation American on both sides, right?

I think I’m one-and-a-half. My mom has a really thick Queens accent. She went to fashion school in New York she designed jeans in the ’80s for Jordache. My dad is from Hong Kong and was a computer engineer for Hewlett Packard in the ’80s.

What did your parents expect of you growing up? What did they think you were going to do?

My parents really didn’t expect anything, and that was maddening at times. When you’re a kid, you get put into music lessons. I was like, “I don’t want to do this,” and they’re like, “Okay.” That’s not a normal reaction for stereotypical Chinese parents. They were letting us do whatever we wanted to. It’s reflected in the professions of all my brothers. One of my brothers is a musician. Another brother is a furniture maker. That has led to us having not a ton of guidance or structure.

My dad had a really overbearing dad and overbearing older brother, so he never wanted to tell us what to do, as a matter of principle. My mom was just really into being a free spirit. She let us do our own thing. To be honest, when I was younger, that really came off as not giving us enough support, direction. I don’t think people become really, really excellent without some sort of pressure, and that was kind of the pressure that I was given. It wasn’t ever pressure to get good grades. It wasn’t pressure to be a doctor. It wasn’t pressure to do anything and except be myself and do what I wanted to do. It’s a lot of responsibility to listen to what yourself and find out what’s right for you, without anyone programming you for that.

“It’s a lot of responsibility to listen to what yourself and find out what’s right for you, without anyone programming you for that.”

You mentioned that going to school in New Jersey was weird. Tell me more.

I think it was like subtly racist in a way that it just is. In a way that’s not explicit, and I think there’s a weird social dynamic there. That’s part of why I moved to Hawaii. It’s like I don’t need to be a minority anymore. And I really carry that confidence with me that I get from living in a place where I’m not a minority, all the time. New Jersey was just kind of very racist, very classist. It was just like not where I belonged. I’m into deep urban-ness, or I’m into nature, but I’m not into this gray mushy zone in between, that’s kind of what the suburbs were for me.

What were your inclinations as a kid? Did they skew technological? Did they skew towards writing?

My father was an engineer, and we didn’t play sports. We would build remote-controlled cars, and I built my first by myself at 7, and the 16-year-old guy across the street couldn’t figure out how to build his, so I knew I was kind of a nerd by that time. We played around computers, and went shopping for gadgets in Hong Kong during my summers. I just had an aptitude for writing and reading when I was younger. I think, I’m actually at the same reading a comprehension level, now that I did when I was seven. Can you imagine not being any better reading when you’re 39 than when you were seven years old? It’s like bizarre.

Tiny genius Brian.

I don’t know if genius is the thing. It’s like, “why haven’t you got any smarter since you were seven?”

I like the bird sounds that are happening on that side of the audio.

That’s funny that you can hear that. There’s parrots here. I think they filmed some Elvis movie that had green parrots, and then they released them at the end of the filming and then they started breeding. It’s this weird invasive, beautiful parrot species that lives in my neighborhood.

Walk me through the windy path that got you into tech, and your editorial career in tech.

I don’t even know—I don’t consider myself in tech. I went to college in Boston and I switched majors about six times, and I took summer school every summer to catch up, but I never did, and ended up with—you needed 100 credits to graduate and I had 150 by the time I was done. I went from Philosophy to English to Journalism to Photojournalism to Computer Science to Business with an IT slant on it. I was pretty good at photojournalism and really fast in the dark room. Then one day this journalist comes in from the Boston Globe and this was like 1999, so it was beginning of a pretty dark age for newspapers. They could see the internet coming. This one veteran was like, “80% of you won’t get jobs and 20% of you who will will work 80 hours a week for $20,000 a year. It’s going to be bad.” And the same week this artist woman that I was madly in love with said, “Well, I want to be an artist, so I’m probably going to have to marry someone who’s financially responsible.” And I was like, “Alright, maybe I should go to business school.” So I transferred because I was a pretty reckless, idiotic, romantic young person.

I didn’t like it at all in business school. I didn’t fit in. I didn’t have nice clothes. And I didn’t do great. But then it was like 2000, and I got a job at this small web-development firm, and within two months of getting that job I got laid off from the bubble bursting. There were no jobs. So in San Francisco I remember, like, seven people who were let go were crying and then I was just like, “Thanks for the job, it was really nice meeting you.” I just kind of knew that I wasn’t supposed to be doing that kind of work. Plus a couple times I got in trouble for reading about gadgets online, I don’t know why, but it was just interesting foreshadowing.

“I didn’t like it at all in business school. I didn’t fit in. I didn’t have nice clothes. And I didn’t do great.”

I went to work at my boxing gym at the time that I’d just joined. I’d always had a really strong affinity for martial arts. I joined this gym, and I went from answering phones and signing people up and sweeping the floors to eventually teaching. That took like 3 or 4 years and I think I learned a lot in that gym about hustle and working hard. I was so happy, just sweeping the floors and exercising like 5 hours a day, 6 days a week and getting into really good shape, making like 5 or 6 dollars and hour. My life was really simple. At one point, I started to just notice like, philosophically, I was not that aligned with this concept of fighting all the time.

I remember fighting with this woman who became a professional later, she punched me in the nose, and then she was like, “Do you want a tampon?,” it was like the constant joke, my nose used to bleed all the time. So, I just started to realize people in the gym were kind of crazy in a way that I didn’t necessarily want to be. Also, fighters don’t age well, they get beaten-up, and you get brain damage, and they start slurring their speech and it’s just really rough. I saw the writing on the wall, but at some point it really came together when the owner of the gym was hurt as badly as can be.

“I went to work at my boxing gym at the time that I’d just joined. I’d always had a really strong affinity for martial arts. I joined this gym, and I went from answering phones and signing people up and sweeping the floors to eventually teaching. That took like 3 or 4 years and I think I learned a lot in that gym about hustle and working hard. I was so happy, just sweeping the floors and exercising like 5 hours a day, 6 days a week and getting into really good shape, making like 5 or 6 dollars and hour. My life was really simple.”

We would practice in a warehouse space and it had a garage door so we could get airflow. The professionals, who trained in the afternoon, were practicing when all a sudden we hear this crash. Out in front, some guy in this like Jeep Cherokee—he looked like a total techie yuppie, some redheaded nerdy dude—had taken his green Jeep and backed it into a car that happened to belong to the owner of the gym, Alex Gong. He was a professional fighter. I think his fight name was F-14, as in the jet.

The techie put his car in drive and took off down Clementina Street into 5th. Alex being Alex, super combative, professional fighter, super aggressive dude, chases after him wearing boxing shorts and no shirt. I think he took off his boxing gloves, I don’t know. Chases him down. The guy gets stuck in traffic on 5th by the highway entrance. I chase after him with a camera because I’m like, “Well, I’m starting to be a journalist. Let me take a photo of the license plate.” So I run a block, I catch up and I see Alex reaching into the car and getting the guy to try to pull over by taking his keys out. The light turns green, and I hear, “Pop,” and I see Alex fall down. Alex was shot in the chest by this totally yuppie looking guy. The guy took off. Some witnesses got the license plate. A cop showed up immediately, but Alex was dead on the ground.

I don’t remember what I did. Somehow I told the people at the gym that Alex had gotten shot. I don’t know if I had a cellphone back then. Alex was lying in the middle of the street, wearing boxing shorts and I was the only one there who knew him. The cop said, “You should give him CPR.” I’m like “He’s got blood and vomit all over his mouth.” He’s like “use your t-shirt as a mask” So I used my t-shirt and I gave him CPR but in my head, I’m like, “He’s so dead, there’s not even any blood coming out of his wound on his chest.” I just knew he was dead. There was no reviving him. He was shot around the chest, around the heart.

For me, the entire situation can be summed up as live by the sword, die by the sword. So we grieved, and nobody really took the lesson the way that I did. And my lesson was you have to find a way that’s not as conflict-oriented in life.

From then I just really started putting energy into my work life. I took the tools from the gym, the work ethic, the hustle, the pacing, the style, the strategy and I put it towards work. I would just work so hard and I got whatever job I wanted eventually, even if I had to apply a few times. That’s how I got in the door at Wired Magazine.

“From then I just really started putting energy into my work life. I took the tools from the gym, the work ethic, the hustle, the pacing, the style, the strategy and I put it towards work. I would just work so hard and I got whatever job I wanted eventually, even if I had to apply a few times. That’s how I got in the door at Wired Magazine.”

I spent a few years there, but it was like me and sixteen senior editors who never really listened to me, as was their right. That’s just how it was at magazines. And so I left for Gawker where I got a job running Gizmodo, which at the time was small. You didn’t leave a magazine for a blog in 2006, it wasn’t a thing yet. But I knew it was a place where I could do my own thing. And so that’s how I got into being editor-in-chief at Gizmodo. And for five years it was not that different from boxing; being punched in the face every day was actually easier than working at Gawker. It was like so combative internally, so combative externally and you burn all these bridges and you just piss everyone off. But you’re doing that to get the story and get it fast. And I really liked that, but I really liked helping people more, which is what led me to leave and do Wirecutter.

It’s funny, this fall I’ll be at Wirecutter five years, and that’s how long I was at Gawker. But at Gawker, I was thirty-five pounds heavier than I am now, because I was so unhealthy, and so unhappy, and so stressed all the time. So, it’s kind of like I can feel my life evolving in a way that I really like.

“And so that’s how I got into being editor-in-chief at Gizmodo. And for five years it was not that different from boxing; being punched in the face every day was actually easier than working at Gawker. It was like so combative internally, so combative externally and you burn all these bridges and you just piss everyone off. But you’re doing that to get the story and get it fast. And I really liked that, but I really liked helping people more, which is what led me to leave and do Wirecutter.”

What was the impetus for starting the Wirecutter?

I always thought it was really weird when I’d talk to other people who are not into tech, they would ask me, “What do you do?” And I’d go “Oh, I run one of the biggest tech blogs in the world.” But the weird thing is if they weren’t in the tech industry, they’d always ask me this one question, which is, “Oh, I’m trying to buy this, like, camera or this TV, or headphones, or—which thing has thing has this, or—can you help me?” And I’d be like, “Actually, I don’t know.” Like I don’t know. Like I know about all these news things, but you just don’t write about that what people should actually buy.

I just saw this opportunity for this list that was not going to make a lot of traffic, but it would just be this master list of, hey, if you need, like, a $500 TV, this is the one you should get. It sounds like, to some people I describe it to, they’re like, “That sounds like what already exists.” And I’d go, “Yeah, but what already exists will take you, like, an hour to sort through, whereas we only need two minutes to use this list, The Wirecutter. Do you want to save 95% of your time that you spend comparison shopping on this one article that can just help you instantly?” And the answer is yes, and once people use it, they get it.

After leaving Gawker, I had all these really great job offers, but I really wanted to do The Wirecutter. I couldn’t stand the thought of it not existing. So I started out small. I just Airbnb’d my house, and sold my fancy car and just got a cheap truck, and I just started working on it. At some point, the idea just popped. I was just living in Hawaii trying to balance out work and surf, and just everything started to get super amazing. I only expected to do it as a hobby, but it became a real obsession for me.

“After leaving Gawker, I had all these really great job offers, but I really wanted to do The Wirecutter. I couldn’t stand the thought of it not existing. So I started out small. I just Airbnb’d my house, and sold my fancy car and just got a cheap truck, and I just started working on it.”

How did all your time in the blogosphere and the whole tech ecosystem affect your decision-making strategy as an entrepreneur?

I have a lot of disadvantages compared to normal CEO. I think as a journalist you have a lot of common sense and you have a good nose for bullshit, and you need to do stuff that you believe in. The Wirecutter was a concept I could really believe in, but I also knew that, because it was so kind of radical at the time, people were like, “How are you going to be ranked on Google? How are you going to make traffic so you can make ad money?” My pitch was like we are going to ignore a lot of noise and only be updated 10 times a month at most. They’re like, “You’re only going to do 10 articles a month?” I’m like, “Yeah.” Then they’re like, “I don’t know how that’s going to work money-wise.” I’m like, “Neither do I. I’m not sure. I don’t care.” If you’re a VC, you’re probably not going to understand why you should give me money after a conversation like that.

“My pitch was like we are going to ignore a lot of noise and only be updated 10 times a month at most. They’re like, ‘You’re only going to do 10 articles a month?’ I’m like, ‘Yeah.’ Then they’re like, ‘I don’t know how that’s going to work money-wise.” I’m like, “Neither do I. I’m not sure. I don’t care.’ If you’re a VC, you’re probably not going to understand why you should give me money after a conversation like that.”

We got a launch sponsor, Intel, but I don’t think anyone but me understood that we were going to have so little traffic because we were not publishing junk en masse. God bless them. I just also knew that in publishing, you can’t apply those kind of models of extreme growth that you can get from launching a free app that has a free service that grows so fast because it’s all free. You know, like you can’t match that with content. Content’s pretty expensive. Anyone who says it’s not is doing garbage. It just doesn’t grow the same way, and if it does it’s growing because of kind of tricks. So, to do something that’s really high quality, you need to allow it to grow very slow in a way that’s not compatible with most modern, tech-oriented VC, and that’s basically what we’ve done. It took about 2 years before I really could pay myself outside of poverty levels but I didn’t need much. I just kept borrowing money and just living very frugally and I just didn’t want anyone telling me what to do or to do it faster. I think that way was the key.

“Content’s pretty expensive. Anyone who says it’s not is doing garbage. It just doesn’t grow the same way, and if it does it’s growing because of kind of tricks. So, to do something that’s really high quality, you need to allow it to grow very slow in a way that’s not compatible with most modern, tech-oriented VC, and that’s basically what we’ve done. It took about 2 years before I really could pay myself outside of poverty levels but I didn’t need much. I just kept borrowing money and just living very frugally and I just didn’t want anyone telling me what to do or to do it faster. I think that way was the key.”

What metrics have become most important to you?

Metrics? Any two solid metrics that kind of go against each other really work for me.

Sessions is really cool because it rewards my team for not only getting new people but having people return. Having people return is a sign of quality and satisfaction and that’s what we’re going for. On top of that, we’re doing some interesting stuff with data. We ask questions like, “Do you need an 8,000-word article on 10-dollar vegetable peelers?” We’ve also learned that after people trust our work, they only read the first like 30 seconds, and then they stop, and they buy what we recommend.

“After people trust our work, they only read the first like 30 seconds, and then they stop, and they buy what we recommend.”

How many people are you paying regularly now?

Roughly 60, plus freelancers. Sometimes people just think it’s me doing it by myself!

What do you think are the biggest motivators behind your work?

The Wirecutter is a really mission-oriented place. So we are not here to make traffic, or be a big media company, or be fancy. We’re just trying to be really useful for people. Shopping really sucks. Everyone has a couple things we’re really excited to shop for, whether that’s leather jackets or surfboards or something that you just will spend unlimited amount of time shopping for. But most stuff’s not like that. Shopping really sucks. It’s such a waste of time and it’s stressful and why even bother with stuff that you’re not that excited about? Helping people with those situations gets us up in the morning. When someone’s like, “Oh, I don’t know what to get. I hate this,” and I can drop a Wirecutter link in front of them like, “Here you go.” That is the most satisfying thing. I love that feeling.

I’m currently using three different things I brought on The Wirecutter for this project.

A microphone?

A little lav and a little recorder and my monitor.

Awesome.

What personally motivates you to do all this stuff?

I think it’s really complex. I love my work so much. I’m satisfied in that regard. But, I would say that, it’s also at the end of the day, we are not our jobs. I have so many things I love to do. I just wish there were 48 hours in a day. Right now, I’d say work takes up 80% of my energy, maybe 90%. I think that’s normal in most people, especially San Francisco friends who work very hard. But that’s not really how it is in Hawaii for a lot of my friends.

You mentioned that in Hawaii, you are not a minority anymore and that is something that you appreciate. I’m curious to know if you experienced isolation or otherness in Silicon Valley?

I think in San Francisco and in tech, I think like being an Asian male is probably the same as being a white male. There is not a ceiling there, or it’s a reduced ceiling. Maybe it’s not on the executive level where you still don’t have a lot of diversity. But San Francisco’s not bad. I think socially, I think in dating there’s discrimination. The data scientist from OK Cupid wrote a book and paraphrasing his findings, he said, “people are really racist when it comes to dating.” The feeling of discrimination is not as strong for me in places where I am not a minority, like in Hong Kong or Hawaii.

Do you have any advice for folks hoping to make it in the big world of tech?

I think you have to take some things really seriously, and then some things not seriously, and you just have to have the wisdom to know the difference. There’s knowing how to work with others, but not following people blindly. There’s a lot of seemingly contradictory advice that isn’t really contradictory if you understand the nuance. Anyone who’s really doing well, in any field, has a bunch of similar traits and mindset. They have these seemingly contradictory things in balance where they do know how to work in a group, but they also are not beholden to groupthink.

What I realized about my friends in San Francisco and LA is that people in California are so much more brave, optimistic, willing to just go for it, than my friends in either Hawaii or New York. I really appreciate that about California, and San Francisco in particular. Everyone is just trying to do pretty big things, if not huge things. That energy is contagious. It’s beautiful to have this example of a peer group that is not afraid to go for it.

“I think you have to take some things really seriously, and then some things not seriously, and you just have to have the wisdom to know the difference.”