My parents first came to California in the 1970s from Indonesia. They didn’t come from wealth, but my father was brilliant in mathematics and used that as his ticket to get out. He studied in California, had in internship in Alabama, where I was born, and then got his PhD at Iowa State. My earliest childhood memories are from my family’s ranch-style house in Ames, Iowa. Lots of snow. Lots of cornfields. Lots of pink puffy coats in the winter. Eventually, we made it east to New Jersey, to a classically suburban town called East Brunswick. It was strip malls, Applebees, exactly what you imagine when you think of a middle-to-upper-middle class New Jersey town.   

“My parents first came to California in the 1970s from Indonesia. They didn’t come from wealth, but my father was brilliant in mathematics and used that as his ticket to get out.”

East Brunswick was super diverse, I had friends of every stripe, and yet I was also the only Indonesian girl I knew of my age. So from early on I felt like an outsider. I think feeling like an outsider—like I never quite fully fit in—trained me to be an observer. I was constantly wrestling with my sense of otherness, exploring why I felt like an “other” and not fully part of the American culture. It became really interested in dissecting people’s stories and understand how people related to each other in groups. That intense curiosity to understand culture and people’s stories drew me to journalism.

How did you first get into technology?

It’s hard not be in awe of tech when you grow up at a time when personal computers were becoming ubiquitous and the consumer internet was unfolding. I remember when my father first brought home Prodigy, one of the earliest online portals, and it was packaged in a giant yellow box. I remember thinking, “Wow the whole Internet—whatever that means—is inside this box.” That sense of wonder sticks with you. As soon as I could type, I remember sneaking downstairs to connect online. Later, my first job as a teen was traveling to computer shows to sell cell phone plans and parts.

“From early on I felt like an outsider. I think feeling like an outsider—like I never quite fully fit in—trained me to be an observer. I was constantly wrestling with my sense of otherness, exploring why I felt like an “other” and not fully part of the American culture. It became really interested in dissecting people’s stories and understand how people related to each other in groups. That intense curiosity to understand culture and people’s stories drew me to journalism.”

I think it fostered the feeling that everything is accessible—just an e-mail, button or Google search away.  The world is smaller, things that seemed out of reach before seem less so today. I think that can have a profound impact on a child’s psychology and sense of limitations. I wouldn’t be surprised if that dynamic is as responsible for the current boom in tech as say the increase in computer processing power.

What were your impressions of Silicon Valley when you first arrived?

I initially moved to Palo Alto in the wake of the financial crisis, while Wall Street and the large economy were still reeling from the subprime financial mess, an interesting shift was taking place, the re-ascendance of technology powered by smartphones.

It was early days, but you could feel that the seat of power was shifting away from the financial sector and moving west. This was a time when Uber was just a handful of employees, when a billion dollars was still a BIG deal with a capital “B,” but the town was electric, brimming with start-ups on the precipice of transforming entire industries and larger-than-life personalities, both good and bad. Who wouldn’t want a front seat?

How did you make that transition from a successful journalist to entrepreneur, and how were you able to leave it all behind?

I found myself restless a couple of years ago. At the time I didn’t know it would lead to entrepreneurship, it was just a tickle in the back of my mind. As a teenager I used to fantasize about my future career, I didn’t just want to become a journalist, I had a plan, I wanted to be on the front page of the New York Times by the age of 25 and permanently on staff by the age of 27, then you know, eventually die at the New York Times. By 2010, I was right on schedule. But something funny happens when you think you’ve accomplished your childhood dreams, sometimes you realize what wanted so badly at 17, is not what you want at 27.

Several moments both big and small eventually led to clarity—one was a short conversation I once had with Reid Hoffman, the founder of Linkedin. He said something that really stuck with me. He was telling the story of Archimedes, a brilliant mathematician and inventor who once said “Give me a lever long enough and a fulcrum on which to place it, and I shall move the world.” Reid brought up Archimedes in the context of his career and how he always wanted to create positive impact at truly massive scale. I had never thought of my own career through that lens but that statement deeply resonated.

“As a teenager I used to fantasize about my future career, I didn’t just want to become a journalist, I had a plan, I wanted to be on the front page of the New York Times by the age of 25 and permanently on staff by the age of 27, then you know, eventually die at the New York Times. By 2010, I was right on schedule. But something funny happens when you think you’ve accomplished your childhood dreams, sometimes you realize what wanted so badly at 17, is not what you want at 27.”

I realized in that moment that that I was also drawn to that north star, and not only that, but that I was hungry for a singular focus. I wanted to drive all my weight against one boulder to move the needle. And as this industry has proven again and again, entrepreneurship is a great vehicle for that.

But it wasn’t all introspective meditation. I would also have to blame my partner Dan for tipping me towards entrepreneurship. Dan, who co-founded his own startup, Zozi, many years ago, has been such a cheerleader and advocate through this whole journey. He helped me realize that I have the constitution to endure this grueling track. He also introduced me to my co-founder Angela several year ago. Even then, when I was still in the thick of journalism, he said, “You’ll love Angela, be nice to her, because at some point you two will start a company.”

It was hard to give up something I spent a decade-plus building, but once I realized what I wanted, the shape I wanted my career to take, the fear of giving up what I had built was trumped by the fear of losing precious minutes in my life in pursuit of what I really wanted.

How has life changed the most since you decided to become an entrepreneur?

Ha, in four words: more stress, less sleep.

The fear of failure hangs over you. At the WSJ, or  NYT, that was never a concern. Sure, I could write a terrible story, but as long as I crossed my Ts and was reasonably responsible there was nothing I could do that was THAT bad. Not so much today, I feel like there are a million ways to fail, a million ways something can go wrong. A young company is just at a precarious state, you’re fighting to keep it alive. You just hope that at the end of the day, you make more good decisions than bad ones. Or at the very least, that the bad ones will not fundamentally change your company.

It’s a constant state of worrying, and learning to handle so many different tasks at once—most of which you’re not qualified to do. In one hour, I could go from designing marketing materials on photoshop, to tweaking user experience on our mobile site, to hashing out regulatory issues. God, I wish there was a manual on how to build a startup, someone should really write the definitive book.

“The fear of failure hangs over you. At the WSJ, or  NYT, that was never a concern. Sure, I could write a terrible story, but as long as I crossed my Ts and was reasonably responsible there was nothing I could do that was THAT bad. Not so much today, I feel like there are a million ways to fail, a million ways something can go wrong. A young company is just at a precarious state, you’re fighting to keep it alive. You just hope that at the end of the day, you make more good decisions than bad ones.”

Second, since leaving journalism, I’ve also had the time to take a real break, physical and digital from the echo chamber of Silicon Valley. We’re building the company in Los Angeles, though I still come up north for a few days once every 1-2 months. The separation has probably helped me be more heads-down in building the company and less tied to the minute-by-minute machinations of the industry.  I admit, I had an unhealthy relationship with Twitter, social media. I essentially took a break and realized that the things I once obsessed about as a tech journalist, I really didn’t need to. It’s amazing how much mental space that frees up.

Has your perspective of the tech industry changed now that you’re on the other side?

One thing: I’m far more sympathetic to the entrepreneur life and entrepreneurs in general. I think when I was a journalist it was easy to be really snarky and cynical. Journalists should always be skeptical, they should be willing to pick apart, rip apart, companies and people. But, now being on the other side, now that I better understand the complexities of what an entrepreneur might be facing, or just how layered those complexities are, I have a newfound appreciation for what founders are dealing with.

“I think when I was a journalist it was easy to be really snarky and cynical. Journalists should always be skeptical, they should be willing to pick apart, rip apart, companies and people. But, now being on the other side, now that I better understand the complexities of what an entrepreneur might be facing, or just how layered those complexities are, I have a newfound appreciation for what founders are dealing with.”

It’s hard to see from the outside what battles people are fighting—whether they’re personal or professional ones. It’s easy to make fun of someone for a design mistake, or a widget that’s just not working that well, but chances are, they’re just fighting to keep the boat afloat. There’s certainly some bad actors in the industry and corporate malfeasance, but, I think on balance, people are often trying to do the best they can. And trying to make something go from zero to one, that’s really fucking hard.

How has your past covering tech as a journalist helped you as an entrepreneur?

In a way, it was like an elite business school I never paid for.

I certainly didn’t approach journalism with that perspective, but it was a welcome byproduct in the end. I’ve interviewed hundreds of founders,  investors, at nearly every stage, from zero to unicorn. It was an immense education, like a long string of Harvard Business School case studies. It gave me the opportunity to closely examine companies and dissect their wins and their failures. And as a journalist, I also got direct access to all the key players, I was able to quiz Mark Zuckerberg about how he transformed Facebook’s mobile business, or interview dozens of Zynga employees, to find out why the gaming company faltered. It was deeply fascinating and educational.

This may sound cheesy, but I think covering this industry makes you acutely aware of man’s potential, the capacity of an individual for greatness. One venture capitalist who’s backed several billion dollar companies once told me that there’s one unifying quality of his best entrepreneurs. It’s not a certain level of intelligence, or their socioeconomic status at the starting point, it is their relentless drive to force their reality upon the world.

“This may sound cheesy, but I think covering this industry makes you acutely aware of man’s potential, the capacity of an individual for greatness.”

A hunger to bend reality to their vision. As a writer, you meet a constant parade of people who have done just that. Suddenly, changing reality doesn’t seem so farfetched, it becomes normalized. More people you know have, vs. haven’t. And you reach a point of “Why not me? Why couldn’t I change the way things are in a fundamental way?”

Steve Jobs once said to an interviewer that the most powerful thing one can learn is the idea that life as you know it was also created, shaped by people, mere mortals, and that you too can change it, shape it. He said once you learn that you’ll never be the same. There’s a lot of truth to that.

You’re a woman, a first generation immigrant, and a person of color—has that helped or hindered your journey?

My co-founder and I have discussed this at length—we are both women, non-white, and children of immigrants.

We are about as far away as you can get from the Mark Zuckerberg ideal. And while I’ve certainly seen sexism—if you think Silicon Valley is bad, try covering Wall Street and finance—I think the attributes that make me an outlier have ultimately helped more than they have hurt.

As I mentioned, I was the only Indonesian girl in my suburb in New Jersey growing up, besides my sister, and when you grow up always feeling like an outsider, you don’t compare yourself to anyone else. You don’t have a mold to conform to, or a precedent to set expectations against. I always approached a challenge thinking, well why couldn’t I succeed? It’s not like I’d ever seen an Indonesian girl fail.

Being the child of immigrants is such an undervalued gift. You watch your parents rise against seemingly insurmountable odds to make it in America but you also see the struggle required to do so. From very early on, I realized that humans are capable of great things but you have to work your ass off to achieve success. My co-founder witnessed the same, her mother was a refugee of the Vietnam War who had $50 in her pocket when she came to America later built one of the largest automotive suppliers in America. When you’re raised with those stories, laziness is just not an option.

“Being the child of immigrants is such an undervalued gift. You watch your parents rise against seemingly insurmountable odds to make it in America but you also see the struggle required to do so. From very early on, I realized that humans are capable of great things but you have to work your ass off to achieve success. My co-founder witnessed the same, her mother was a refugee of the Vietnam War who had $50 in her pocket when she came to America later built one of the largest automotive suppliers in America. When you’re raised with those stories, laziness is just not an option.”

What has the experience as a female entrepreneur been like? Anything surprising?

Before becoming an entrepreneur, I didn’t really think about how my gender impacted my career. I think I was lucky to have strong female mentors in journalism and to have worked in diverse newsrooms. Not once, did I feel passed over for a promotion or an assignment because of my gender. Yes, I saw and reported on sexism in tech, but I never had to wrestle with those issues in my workplace.

It’s different now. I am definitely more aware of my gender.

Anytime I walk into a room or attend a conference, chances are the ratio will be heavily skewed to men. The decision makers skew male. Way male. And even when gender discrimination isn’t overt, I think women in tech are always left dissecting and wondering, “Well, did he say that, or did that just happen, because I’m a woman?”

I fear that progress will not happen quickly, it’s hard to reconfigure a decades-old, patriarchal-based system. Tomorrow, you can mandate more seats for women on boards or at venture capital firms, but that doesn’t solve deep-seeded gender bias, the lack of respect for women executives and investors. However, I do have to say, I have been pleasantly surprised by the number of men who’ve stepped up to help, to be so supportive, who are real champions of women. I can point to dozens who’ve really helped me over the last year, but I know I’m lucky.

“I fear that progress will not happen quickly, it’s hard to reconfigure a decades-old, patriarchal-based system. Tomorrow, you can mandate more seats for women on boards or at venture capital firms, but that doesn’t solve deep-seeded gender bias, the lack of respect for women executives and investors.”

Where do you see yourself in five or ten years?

Hopefully still doing this. I really believe that what we’re doing is potentially very profound, and I want to keep it alive long enough to see the change actualized. In five years I hope to be exactly what I’m doing now, but hopefully with more progress. And hopefully less stressed —but knowing myself—probably just as stressed.

What advice would you have to other aspiring entrepreneurs or folks wanting to leave what they’re doing now to start something they’re passionate about?

I don’t want say, ‘just do it,’ and suggest you quit without really thinking it through.

You have to really look at yourself and think about if you have the mentality to do this because it will beat you up. and most of this is not glamorous, so a heavy dose of self-reflection that’s stage one. Be ready for the roller coaster of being an entrepreneur and potentially losing everything.

When I was about to make the leap, I made myself go through a thought experiment. I asked myself, “if everything fails and it all ends in dust, what’s the worst outcome?” And I thought, well I’d probably find a job and even though the first job may not be as prestigious as past ones, I was fairly confident that I would at least find A job. And I realized I was 100% comfortable with that. That’s not terrible downside when you consider the amount you learn through entrepreneurship, and failing, and of course the potential upside of building something great. But prospective founders really have to be O.K. with the prospect of losing a lot.

Then, if you clear that hurdle, then I think there’s just the matter of figuring out what your path to success will be. Of course the best laid plans are always mucked up, so I’m not saying to draw out a blueprint in ink. Instead, have you thought through what your competitive advantage will be and what it will take to succeed? Do you have a sense of the big pieces you will need to get this to lift-off, and are you ready for the challenge of forcing this vision into reality.

“You have to really look at yourself and think about if you have the mentality to do this because it will beat you up. and most of this is not glamorous, so a heavy dose of self-reflection that’s stage one. Be ready for the roller coaster of being an entrepreneur and potentially losing everything.”

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.”

I was born in Sacramento, and I graduated from college at UC Davis with a degree in English. I got my start as the editor at my college paper there. It was a self-supporting newspaper with a 250-person paid staff. That was where I learned to write and edit, how to manage people, how to fire someone. It put myself through school writing five articles a week on top of my course load, it was good practice for the internet.

I grew up thinking I wanted to be an elementary school teacher. But by college people would argue when I told them that. “No, you want to be CEO of something.” Outside perspectives can be helpful when you’re 19.

By graduation I knew I wanted to own my own business, so I started a silk screening shop, and it was the pits. I had trouble motivating to go in and work, so took a part time maid job to force a schedule. I would clean from 7-8 a.m., and then I would go to “the studio,”  which was a rented U-Haul space.

One day when the fire marshal came to the door. I literally had a room-sized drying machine that would routinely set t-shirts on fire. And I mean, like once every maybe 30 minutes something was smoking.

He knocked and said, “We need to do a check of the premises.” I was thinking, “Things are on fire right now. As I am here answering the door, things are catching fire.”  So I said, “Oh! Well, my boss isn’t here. Can you come back another day?” And he was like, “What are you doing in here?” And I said, “Painting t-shirts.” And I made a motion like I was using  a paintbrush. He was like, “Okay. We’re good then.”

And then I went back and put out all the fires that had caught in my absence. I eventually got out and worked as a secretary for a year or so. It was incredible to just go home at 5 p.m. and be done with my day.

How did you get into tech?

One day a friend called from the Bay Area and said, “I get $3K if you’re hired as an editor. You’re interviewing.” They were offering hiring bonuses for referrals because tech needed warm bodies. That’s how I became the assistant editor at the prestigious Windows NT Systems magazine.

What was that like?

Well, I was broke. I was living in a crawlspace in a garage in San Mateo. Literally the door to my closet was a cabinet door seven feet off the ground with no ladder. I would climb up onto a nightstand and heft myself up into the room.

But even if I’d had money, there were no apartments. No one in San Francisco would rent to you if you were in tech because there was such a backlash against tech workers coming to the city.  I was in this weird place where I was like, I have an English degree and I am making $20,000 a year. I can’t afford to live without roommates, and literally no one will even talk to me because I’m technically working in tech right now.

Really?
Yes. It was bad. That magazine eventually closed, so I applied for a new job as an associate managing editor for a magazine called Web Techniques, it was for C-level web execs. I worked my way up from there to senior editor and then managing editor by the time I was 25. The editor in chief was 26, which was unheard of at the time.

I still wasn’t making enough money to live in San Francisco, so at night we would go through our PR invites and hit all the launch parties that advertised free food and drinks.  And then sometimes you couldn’t get a cab back. We had all this inflatable furniture in the office left over from the conferences our company threw, so we would go back and sleep on the inflatable furniture in empty cubes.

I remember at one of those parties there was a girl in head-to-toe Prada, and I said to my editor, “That girl’s outfit cost more than her parents’ car. What is happening right now? There’s no way this can last.”

And it didn’t.

No, it did not. Web Techniques eventually closed in the bust. And over the years, the tech crowd shifted.

How so?

At the start, tech attracted true nerds, people who had been picked last at kickball and knew what it was like to be marginalized. There was just a wealth of sensitive, really bright, motivated, charming young men who maybe were a little awkward with women, but who were respectful of the community.

When I was a journalist, South by Southwest Interactive was only a few hundred people. You knew everyone there. You definitely knew who all the women were, because there were so few of us. At that time, by virtue of you being there, there was more of an assumption of your right to be there, because there were so few people in the space. If you were there, you were part of it, it was meaningful. There was sexism, of course, but it wasn’t as widespread and overt.

Since San Francisco became an industry town focused on tech, there’s been a shift away from people being more creatively oriented. There are fewer futurists and more people focused on money.

When the social web came into play, things started to turn. You’ll approach a group of men, a few of them are friends, but maybe one or two of them don’t know you. When you approach, often the new guys make the assumption that you’re not a meaningful presence. And so, they do all of the things that people do when they discount you. They turn their body away from you. They turn you out of the circle. They don’t make eye contact in a prolonged conversation.

And now, and this is gross, I sometimes find myself doing it. When I see a woman around a lot, I occasionally will assume that she’s someone’s wife, as opposed to assuming that she’s a tech person. You just don’t see a lot of female faces.

How did you get into blogging?

Working at the magazines, I met a lot of the people who formed what we think of as the social web today. I already had a personal site when I was editing a sidebar in the magazine about Blogger. So I turned my site into a blog.

Many, many years later it became possible to making a living with your blog, but the landscape was nothing like it is today. There were very few subject-specific blogs, maybe a handful focused on tech. And then Movable Type came on the scene and gave some more powerful content management tools. I realized that you could use that to make a magazine-style blog, and that no one was looking at more traditionally female topics.

I launched a site called Mighty Goods, it was the first shopping blog. It was, I think, the first content-specific blog aimed at a a female audience. It was among the first handful of blogs that focused on a specific topic. It was listed as one of Time Magazine’s Top 50 sites, so I launched a couple of sister sites — Mighty Junior and Mighty House — and all of those were eventually acquired.

Mighty Girl was starting to make money, but I didn’t have children, so the ad agency didn’t really know the best way to sell me at first. There weren’t a lot of lifestyle brands buying online campaigns. I was getting pitched a lot of Pampers.

Also, audiences had turned to blogs to get away from the mainstream messages and commercialization. People cussed on their sites, or spoke candidly about controversial things. So to sanitize yourself to get advertising was anathema to the entire exercise.

So what did you do?

Because of my background with editorial I thought, “Okay. What are advertisers looking for? They’re looking for a narrative. Right? What narrative could I provide that would let them give me money to write about whatever I want?”

So, I wrote up what I call a Life List, the less-morbid version of a bucket list. And that’s what I became known for. I spent a year and a half making decks and pitching, and there was some eye rolling from some of the salespeople I was working with. But eventually Intel picked me up as part of their Sponsors of Tomorrow campaign.

They sent me to swim with bioluminescent plankton in Puerto Rico, I was zip-lining, I was learning to roll in a kayak. It was all this super adrenal stuff, which if you know any writers, we’re people who like to sit in warm bathtubs with a cup of tea.

And in the time between coming up with the Life List idea and getting to execute it with sponsorship, I’d had a baby, which changed things.

How so?

Well, before the Life List,  Mighty Girl was slowly making money, Mighty Goods was doing really well. I got a book deal to write No One Cares What You Had for Lunch: 101 Ideas for Your Blog. And I was writing a regular sidebar for the New York Times that featured unusual items for sale on eBay.

Then one night my husband and I were going to dinner at a friend’s house, and he said, “We need to do some math. If we want two kids before you’re 36, we should have started trying by now.” I just went pale.

I was thinking, “Oh my god. My career. I just won all of these awards, I have my book deal, my site is taking off,” I was at that dinner like, “Holy crap. It is time to get pregnant. It’s today.”

So I did. But being an entrepreneur and trying to be a primary parent blows. Babyhood is a very fleeting window. You want to be with your kids as much as they want to be with you, but work is always waiting.

I was raised in the have-it-all generation. Now there’s that adage, “You can have it all. You just can’t have it all at the same time.” Well, actually you can, it’s just overwhelming and kind of crappy.

I always thought that I would re-enter the conventional workforce, but tech is so dominated by people in their 20s. There’s also a culture of hustling to make sure your value is noted by coworkers. And it’s difficult for them perceive that value if they haven’t felt the push-and-pull of a family life. I was like, “Man, I don’t want to be the person at the company who is doing less than the people around me, or even perceived to be doing less.”

I always want to be the person doing the most, hustling hardest. And that amount of effort requires an unconventional schedule with kids in the mix.

So you grew your own thing.

Yes, I took on some partners and launched an events series that ran for five years. We had invite-only gatherings called Mighty Summits, and a more conventional conference called Camp Mighty. Eventually we founded Go Mighty, which is the community version of the Life List.

And the premise of it from a business standpoint was that it was sort of like an ad network with a soul. We would bring in companies to sponsor influencer’s goals, and then often it would include a societal good component.

Overall, what do you still feel are the most important things to you in your work?

There is, obviously, the need to make a living so that you can eat and your children can eat. Beyond that, I’m motivated by people’s potential. Connecting people with each other or with ideas, sparks a chain that creates good stuff in the world. I like to be a part of that.

I see technology as the most creative force available outside of the art world. The side of tech that still has my heart are the creative people who make things and build things, people who are globally curious. And getting to talk to those people and create things with them is awesome.

I have monetary goals around health, education, and social justice. I’d like to raise $100K for each cause. Event attendees raised $80K for Charity Water, so we’re only $20K away from the health goal. Also, one of the goals with Go Mighty was to redirect $1 million in corporate advertising funds toward campaigns with social impact. So those things are still important to me.

I’m interested in how advertising can become information, and also how we can tweak ad budgets to serve multiple purposes. I’m also thinking a lot about how we could automate systems to make it less work for people to donate money. We’re looking at such a huge income disparity, it’s time to start putting more of our best minds to solving that.

Where do you think you got your hustle from?

I was the first person in my family to graduate from college. My mom used to say, “If you liked it, no one would pay you to do it.” So it cracks me up that I’ve literally been paid to check things off of my Life List.

My father passed away when I was eight. My mother was very ill. She didn’t have traditional jobs open to her, because she couldn’t work nine-to-five reliably. So she had an antique stall, or when I was tiny, she had a newspaper route. She delivered 2,000 papers a day, and sometimes she would wake me up to go get warm donuts. Then she’d put me in the bed of the pick-up truck, and cover me with papers. I would sit in the back of the truck and throw newspapers out. That’s one of my nicest memories.

Watching her make it work with the energy and resources she had was very motivational. She said, “If anybody’s ever paying you, they better see you working at all times. Don’t sit still. That’s how you lose a job.”

Idea generation comes easily to me, so I value people who say, “Okay, let’s do it.”  I can sit in a room come up with 400 cool ideas, but at some point you need to get your bum in gear. And the bigger the plan, the more help you need.

Within the lens of everything that you’ve talked about, how do you feel about the state of tech in 2016? Like, you’ve seen a couple  cycles, you probably see things repeat themselves in certain ways, and be different?

I’m curious to see whether there will be more of a verbal tradition, whether histories will start to be passed down and collected more, the way you’re doing here. It’s weird that tech doesn’t tend to respect experience, though it might be a byproduct of a time when older people hadn’t grown up with technology so didn’t know much about it.

When you’re trying to innovate quickly, and fail quickly, experience is invaluable. Is that company a unicorn, or a horse with a horn glued to his forehead? Experience saves time and resources.

The lessons that we’ve learned with other people’s money, with how we treat our communities, or people’s personal information, they’re often lost in these new endeavors. Everyone is too young to remember when the wheel was invented the first time.

Aside from that, I’m surprised that the industry is still so homogenous. When you have the relatively homogenous group of people building the future, the future is more of the same.  And I think we’ve collectively decided that’s not our jam, the future being more of the same.

That said, people are using the technologies provided by that legacy to make new things happen, and to connect with each other and shift things, so maybe it will work for users to meet creators halfway.

What life goals you’re working on at the moment, either for work or personally?

I had a difficult pregnancy, so I took a sabbatical to have this baby. It’s the first time in my life I haven’t been working. It’s strange, but it has been nice to have space to enjoy his babyhood.

I’d like to do more interviews, and maybe a speaker series. For the first time in a long time working at a company again sounds appealing. The learning curve is there, and it would be cool to work with people who know more than me.

My last question for you would be based on lessons that you’ve learned over time. What advice would you give to folks from similar backgrounds, maybe just chicks hoping to get into tech, based on what you’ve learned over time?
There is power in being different. It makes you memorable and intriguing. People who don’t automatically recognize that probably aren’t people who you would have successful working relationships with anyway. I think it is much more to your advantage to be a woman in this field than it is to your disadvantage, if you can keep your morale up, and if you can learn to dismiss the people who dismiss you. You’ll have all the success you need just working with the people who see you.

I was born in Washington, D.C. Both of my parents migrated from the middle of the country to an urban center, because they had to escape their sort of tough rural backgrounds. My parents were working middle class people, educated through high school but aspiring for more, and in Washington they could have white collar jobs. I went to public schools in DC and I loved growing up there because I just got a great sense of history and news in the making – all that sort of thing. [Washington] was to a degree integrated [at that time], lots of international people were there, and obviously lots of African-Americans. Looking back I’m really glad I had that [experience growing up].

My first aware career aspiration was to be an artist [chuckles] – I meant like with a beret and a smock and palette, you know? I had no real career sense of anything about professional life, but my parents always said—because they were working class—”You have to work and support yourself, no matter what.” So that was a given. “We don’t care what else you do, but you’re going to work and have a job.”

I graduated from high school in 1969. In other words, I was a hippie. There were various cultures at my high school, but hippies were definitely a big contingent, and that was the easiest one for me, because I was not ever a girly girl, I was not ever into dating, so that was just the group that suited me and vice versa, I think. My parents were church-going people, and [they sent me to] a little Lutheran college in Ohio, which they strongly preferred. I thought of myself as an urban person, but I ended up actually loving my experience there. The school is called Wittenberg. It’s one of like 10,000 liberal arts schools in Ohio [chuckles]. And I made lifelong friends there, I had wonderful teachers. But, again, no big career plan. I studied what I wanted to study – all liberal arts. It was humanities all the way – lots of literature, lots of history, art history. My mom had insisted I learn typing in high school, so I had typing too, and that has been my life ever since, really.

My dad died when I was a senior in college. Without a clear plan, I moved back to my mom’s in the Maryland suburbs and got jobs in Washington for a couple years, and went to graduate school then, [once] again in American Studies. So I have two degrees in American Studies. I was in a Smithsonian program, studied material culture and folklore and things like that. I enjoyed that, and I also worked at the same time. That’s how I paid my tuition, by working at George Washington University.

I was now a young professional adult with young adult friends. Still didn’t have any particular plan, I held office jobs, and I was smart, and I could type, and I could read, and I just had a series of those kind of jobs. In graduate school, I studied oral history, and I happened to be at school at a time when a couple of local professors uncovered what had been missing for 40 years, the archives of the Federal Theatre Project, which was part of the WPA [Works Progress Administration]. There were just trunks and trunks of material that the Library Congress owned and had misplaced. These two found it, and got a big grant to catalog it all.

So thanks to my graduate work, I actually had a job in my field, which is to say I became the oral historian for their [FTP cataloging] project for two years. And that led me to do what you’re doing now, which is travel around the country and interview people who had worked for the WPA Theatre Project, when I was 25 or 26.

What a dream.

I loved that because I knew the material very well. The [interviewees] were all charming theater people, by and large. They included people like – these are names that may not mean anything to you – Joseph Cotten, Arlene Francis, people who later became big stars. And so that was fantastic. [This project] didn’t really lead anywhere, and I knew that. I remember [thinking] that I didn’t really feel like an academic career. Some of my graduate school friends pursued going further into the field of oral history and historical projects.

I felt like, I don’t want to get further away from the real world, because I was already so in my head. I didn’t want to get a PhD, I thought a master’s degree was plenty. Anyway, I enjoyed that period—it was couple of years—but the [FTP] grant money was coming to an end and the project was more or less done.

Again with no clear plan, I had met a guy and he didn’t have a big plan either, and Ronald Reagan had been elected, and was coming into office. This was 1979, and I said, “I cannot live in Washington under Ronald Reagan,” so we moved West – but we had no plan. We took four months to drive across the country. We did end up in San Francisco where we had friends, but when you’re in your late 20s, nobody has really a stable place to live for long-term visitors who come and hang out with you while they’re looking for jobs. We were a little intimidated at the time, and ended up going up to Oregon, where I had another friend. [Eventually] I did get a job in Portland, and and [ended up] stayed there five years. I worked on an oral history project that had to do with women shipyard workers [during World War II] in the Pacific Northwest. It paid like five cents. It was a side thing, but it was still interesting. I also had a job in a little non-profit, a membership group of independent filmmakers, because I was interested in media. This was basically like an office job, running a little membership organization, I think there were two and half people on the payroll [laughs], including me. As a result of doing that for a couple years, I met somebody at a conference who said, “There’s a job in San Francisco. You should apply for it. It’s a bigger organization.” And much as I loved the Northwest, Portland was extremely depressed in the 80s, had no real economy. It was a pretty run-down place, charming, but it wasn’t big enough [for me].

So, I did apply for this job and I got it. And it was [with] an organization called Media Alliance, which had a lot of progressive media types, and [also] people who were moving to the Bay Area looking for jobs. So, I took the job. It wasn’t that enjoyable [thin margins!], but on the board of directors of this organization was a guy named David Bunnell who started PC Magazine and then PC World magazine. Now, he was a quirky guy, kind of nerdy, kind of shy, a bit of a weird character. But he took a liking to me and talked to me very readily, where he didn’t talk to a lot of people. After about a year at Media Alliance, he said, “I want to hire you.” He was running a computer publishing company in this heyday of thousands of computer magazines. The beginning of personal computing. I said, “But I don’t know anything.” I used a K-Pro! But he felt comfortable with me, and I was going to be his conduit to the real world, is what I realized after I got there. Going there doubled my pay –  stability at last. And I loved the people. I remember thinking in 1985, “How is it that there’s a world with all this jargon, all this lingo, that a world of these magazines, I barely understood what they were talking about. These trade shows, like Comdex. How has this sprung up so quickly out of nowhere? Where did this come from?”

All the people in [computer publishing] at that time, nobody that I knew was really experienced at it. Everybody was new and young and getting into it – but we were really smart, bookish, funny people and so, I just loved it. I just loved learning about magazines, I loved putting them together, and having a regular schedule, and working with people who were funny and were making fun of technology as they were working on it. It just suited me perfectly. And that’s how I fell into technology.

I stayed there four years, and I was David’s right hand. We started a little R&D group. I worked a lot with the editors of the different magazines. Again, now I have life-long friends from that experience.

Eventually, he left because his contract ended. I, again, didn’t really have a plan, but by then, I knew people, and so, I got a contract for about a year to start a new technical journal for Addison Wesley, a book publisher. They’d never done a periodical, and I had a strange experience dealing with mathematician Steven Wolfram (the journal was about his program Mathematica). Once again, I just sort of felt my way. But now, I began to have a network of people who work here and there and who knows things about  publishing and who knew things about technical stuff. It just led to different—sometimes freelance—jobs. I think I had a freelance period there for a while where I was writing and editing.

We’re in the early ’90s now, and I had a job at an awful technology PR firm, one of the early ones. I didn’t like doing PR, but I liked the people that I worked with. That led to a job at a very hot startup called 3DO – and my first IPO. I had friends who’d already been through IPOs, and I was determined to be in one too. [3DO] was a big hit for 20 minutes. But again, I met good people there. That’s where I first met Omid Kordestani, was at 3DO. Again my network grew because everybody I knew was doing the same thing: You’d move here, you’d move there, you’d have a new job, you’d try something out, [you’d make friends along the way].

After 3DO, I had a couple more years of freelance work. By now my editorial friends were editors of different magazines. So as the web came online, I was invited to put together one of the first consumer guides to the web. It’s so antique now. I should show it to you. It has lots of spider and web puns in it, it’s just ridiculous [chuckles]. It came out in 1995. I didn’t get a lot of money for it, but it led to my editorial friends inviting me to review LOTS of websites for their publications.

So I did that for a couple of years, writing up consumery-type things for tech. I was never really particularly technical, but I knew how to explain the value to [consumer readers]. And then I joined this startup a friend of mine had got going called Planet Out. It was really the early gay portal. My friend [Tom Rielly] is a great character, and he had this vision of this web and AOL portal that would be news and information for the gay community. I was the executive editor, assigning stories and hiring writers. It was great. But it did not do well as a startup. I left and went back to the magazine side – [I became] the executive editor of Upside [a hot monthly mag then].

My whole mantra during this period was, I can work in these kind of corporate climates if I feel like I’m providing useful information, or it’s something that people can use. I can remember when I joined IDG,  the parent company of the first computer magazines, I remember thinking, “Well, it’s not Bechtel.” I mean, [IDG] has a public value. They have a usefulness to people. And that’s what I cared about. And that, I think, has been a guiding thing for me.

Upside was interesting, because it was about the business of technology, which has become a really interesting area. I liked having a big role at a magazine, where I worked with a lot of writers. I knew I was a good editor, and that made me a better editor, to be working with good writers, and to have back-and-forth conversations about what they were trying to do.

I stayed 18 months, but it was just a bad atmosphere, so I pivoted then. I thought, ” if the web is going to be a big thing, I love information and words and ideas, so how now, since we don’t have to be linear anymore, and we’re not limited by a page, the size of a book, the size of a magazine, how then to present information and make it discoverable?” There was a thing then called information design, which now has morphed into UX and content strategy. I had friends at an early web design firm [Studio Archetype] that were really getting into this in a deep way. They kept saying, “You should come over.” I did go, where I managed teams who did that, [and in the process, I gained an] understanding of business development; what is content strategy; how to take somebody’s corporate information, business information and make it useful online, chunk it up and all that sort of thing. Again, I loved the people there. Really fantastic group. It was a great company, but it wasn’t particularly financially successful, because there was a lot of overhead. So they ended up selling to a much bigger systems integrator [Sapient].

And that [integration] was fascinating to go through, because we were a little artsy design studio, and here came this much bigger [entity]. [Sapient] was a consulting business [which plugged people into long-term projects like this: “You’re an engineer with three years of C++, you’re going to Dallas for two months” or whatever it was. They couldn’t really figure out how to plug in the creative people. And the creative people mostly revolted, of course, but again, the process of going through an integration that didn’t work well was pretty great. And led me to understand why acquisitions often don’t work [laughter].

Somewhere in here, one of my old friends I had worked with at two companies, I kept in touch with her. In 1999 she said, “Hey, I’m taking a new job at this startup. It’s called Google, come visit some time.” So I kept in touch, I visited her a couple of times around 2000. The way I understood search [on the early web] was that one of my writing assignments was to compare search engines, and there were tons of them before Google. So, I had looked at them and tried different search terms and stuff. When it came to Google, it was instantly so much better than all the others. Many orders of magnitude better. It occurred to me a couple of times that I should call her, because I was still freelancing here and there. But I thought, that’s a long commute. Much to my regret!

The big tech crash happened in 2000. I was at a little startup that folded. It was tough then for, I don’t know, close to two years [because jobs dried up]. So I was freelancing, but my income had really dropped – and I had bought my first home. Eventually I called my friend at Google and said, “Hey, you have any freelance work?” She said, “Oh, we just hired a marketing writer, but I’ll keep you in mind.” And she called back, maybe a couple of months later, and said, “You know what, we’re really slammed, so come in to meet some people.” So I went down, and they were really nice. They said, “When can you start?” And I’m like, “Right away.”

So I started out as a marketing writer on contract to Google in 2002. Right away, I liked the people, and I believed in what they were doing. I [remember thinking], “This is in close alignment with my values. They’re helping people find information, it’s a service that is useful.” And of course, they had that great mission statement. So, I just started telling people there: I want to work here, I want to work here, I want to work here. By this time, I was enough of a utilitarian writer and editor – I could take copy and turn it into something good quickly, so I just made myself as indispensable as I could around the office. And I tried to be enough of a fixture that people would say, “She’s one of us,” It  took more than a year. Eventually, I did get hired on to be full-time. I was 50 or 51 when I got hired there. By then, I’d had this long, tough stretch where I was not earning enough, and so I just was so grateful to get in. I remember thinking, “Please, God, don’t let them have an IPO until after I get in!” And they didn’t. (It took another year after I joined.) I just made my way in the communications team… I knew enough about how PR worked, there was no confusing me with a flack, and everybody understood I had this different role. Google was small enough and young enough that there were lots of things that hadn’t been identified that just popped up. I think that formed a lot of my experience.

My view now is you just have to try things, and you can’t get hung up by the job description. You can’t get hung up by the title. You have to get in there and see what happens. In a place like Google at that time, that’s perfect, because it was not at all tamped down, it was kind of messy, and a lot of things needed doing. You were encouraged to try different things. I learned how to navigate.

Meanwhile, Google was growing up, getting bigger, but because I’d been there early enough, I became sort of part of the furniture and a little bit of an old hand, in all the best ways. The team grew up. What I did became more specialized, or I became known for a couple things. One was managing the original Google blog, which it turns out to have been an early company blog, at a time when companies didn’t do that very much. Google was different enough that it did. Then, all around Google, everybody wanted their own [blog] for their product and their country. So, I codified what the rules would be about how to do that – and then for a few years, people wanted me to talk about this, because they were fascinated by Google, but also wanted to publish company news on a blog. [Other places] were navigating complexity with lawyers, who didn’t want them to do this sort of thing. I had done it, and it worked pretty well. It worked pretty well because Google people had flexible minds about this sort of thing. They weren’t hidebound and that really helped.

In 2009 I had been watching Twitter. I knew the Twitter guys, and I thought, “Google has to be on Twitter.” I made a case for it internally, but initially people said, “we don’t need another channel for our news.” I said, “Twitter has attracted lots of techies, including reporters. We need to be there. I’ll do it.” They said, “that’s good, because we don’t have any headcount.” I said, “you don’t need headcount. I can do this.”

So I brought them around. [My thought was] this is a layer of an audience that you don’t get another way. I still believe that about Twitter. You raise your [visibility] and reach more people. So, I became known for bringing @Google onto @Twitter – which is ultimately what led me to getting a job at Twitter. Because at that time Twitter was like a younger company that had not codified this stuff. They hadn’t really thought it through. So I came in to do this and embroider lots of things related to it. There was an atmosphere of, “we’ve never really done that,” or, “We do it a different way,” or, “That sort of fell off the radar, so we don’t know.” Now I say, “Well I have an idea. Let’s try it and see.” I just think my lack of [having a plan ahead of time] has saved me a lot of ulcers. I tell people who are sometimes a lot younger, who get super hung up on the trappings, or what it says on the page about the thing, or what the original was: “Well, it can change. It can change. Just relax. If it’s not tenable, it’s not tenable. But let’s find out.” I think that’s just been my approach, “It can’t hurt you to find out.”

How have you seen tech evolve and change over the years?

It’s just so much easier to do things now, right? You used to have to have floppy disks. The idea of the amount of space they have for anything is just—everything was just bigger and slower.

I remember even when I was at IDG the computer magazine company, I had a contemporary Macintosh, but there were networking problems. And I guess we were all on just a local area network, I’m guessing, because it was before the internet really took off. And I remember I had my little phone address book and I had a post-it list, every day, a list of people I needed to call, and I would call people on my phone – which I don’t do anymore at all.

So in a certain way, it’s astonishing how much tech has changed in not very much time. I remember when I got into the Mathematica project. These were academics, right? And they were at universities like Princeton. And I remember talking to some of them about articles, and [at a time when] there were all kinds of weird publishing systems where you were submitting to ftp [sites] and all this stuff.

I remember [asking] this guy, what’s your email address and he said so and so at princeton.edu. I’m like, that doesn’t make any sense. What service are you on – MCI Mail, are you on CompuServe – you can’t just have an address. [laughter] What are you talking about? Of course, they had addresses, right, because [academic email] had come out of DARPA. They just had [email] addresses. That’s what we were all going to be getting [instead of subscribing to one closed service or another]. I didn’t understand that for a while. I had every account for the longest time.

At Macworld, we had an early project – we were trying to figure out how to put Macworld magazine online using GE’s AppleLink, and we were asking, is there a way to turn off the meter so people see the ads but they’re not being charged for the ads, because it was like 35 dollars an hour to have access over that kind of network. That was like 25 years ago. It’s not that long. It feels ancient but it’s really not. It’s kind of astonishing.

So it’s changed in a ton of ways. I’ve lived in my place for 16 years. When we moved in, we threaded CAT5 cable throughout the house, and there are Ethernet ports in every room. But I haven’t used Ethernet in five years or more. Now I have Nest thermostats and Nest smoke detectors, and things like that.

You can’t fathom it in a certain way, you can’t believe it’s happened that fast. Even though we’re in a bubble here, it doesn’t just touch an exclusive population in the Bay Area. [Internet access] has become ubiquitous and important for everybody; that’s the most fascinating thing.

When the Internet turned commercial and Wired magazine started, I still remember Louis Rossetto’s opening essay, “There’s this giant tsunami of technology information coming our way, in a good way. We welcome it.” He started a category of publishing that still exists today. [But] we don’t need the kind computer magazines we used to have, they’re all dead. Can’t even find them online in some cases. But you know what? It doesn’t matter. I have some paper copies, it doesn’t really matter. It’s more like having some understanding of how it’s all come along. And I laugh because I’m just as impatient as anybody else now — like I can’t get a signal, I can’t get wifi – I don’t stop and think, “This is so great to have it [at all].”

How does it feel to have such a depth of knowledge and experience, and be surrounded by so many young, enthusiastic folks who are super brilliant, but have no context for what they’re in?

I wish they cared more about how fast [technology development] has come up, and I wish they cared more about history. But they don’t. I think that’s more or less the nature of people. You don’t really care that much about the past. I like history and I like understanding the relationship between past and present, but I don’t think a lot of people do. Now people are completely tuned into the world of today. I do sometimes wish people understood how miraculous it all is in a certain way. But they don’t. We start from where we are.

I made friends at Google who were engineers, younger than me, but [of course] way more technical. It’s fun to see them and geek out with them about how things were [even in the early days of Google]. Honestly, even a few years ago—I mean I’m friendly with one of the early early early engineers at Google, who was like employee number eight. He and I used to print out like raw pages of the Google search index every month to figure out the original Google Zeitgeist – which we would publish monthly!  So we would take the printout—just search terms that people had put in, and we tried to come up with interesting patterns for music themes, or sports, or holidays, or whatever it was. I’d print out like 50 pages and we’d go through with a yellow highlighter. That is primitive, right? And that was not even 15 years ago. Anyway, it’s fun to think about. You just pick who you can [to remember] about that stuff who also has an appreciation of it.

What has become most important to you in your work over time? How does what you want in a job now differ from what you wanted earlier in your career?

I’m from a one step removed from blue collar background, speaking of my parents and how I grew up. People had [to work]. You didn’t think about quality of life [chuckles] or [larger] aspirations. My roots are in that. Obviously, over time I have cared [about quality of jobs], I have quit jobs I didn’t like and easily got other ones many times over the years.

So I have had more expectation about what I did want, and I guess the biggest driver for me, thinking back to our last conversation, is probably [paying attention to] what a company does. Right? What the business is or the industry, that does matter to me. That has become important, like thinking about working somewhere that provides educational information, useful information, that has sort of a public service to it. Which I think [both] Google and Twitter do. I’d have a harder time working in many industries…even in technology, it would be much more of a stretch for me to work for a company that made some piece of hardware that was a peripheral or something. I like being attached to something that has a public good and a public value. And frankly, that is world-changing. I think that has determined for me, maybe for the last 20 or 25 years, some aspect of what I’m doing for a living. It’s lucky that I landed in those places, in order to form that thought. I could have gone down other roads, and that part seems like happenstance. But, then once I got into this [technology] world, this is an important driver to me. I couldn’t go be the editorial director or creative director at Coca-Cola, or an insurance company, or something.

What are your biggest motivators? What drives you?

One is the mission, or the cause, behind the business. And, by the way, much to my surprise, like working for a for-profit business. I wouldn’t have expected that of myself. I had my earlier years were non-profit and educational institutions. I just feel like this is where stuff is being sorted out that affects so many more people.

I think besides the sort of mission of the business has, working with smart and creative people whose skills are varied, a mix of races and countries and backgrounds – a rich mix of people is a big motivator [for me]. I don’t think I’d like being somewhere where conformity was valued or where people had to really tow the party line. I just read an item today about how Time Inc. made a business-sized card now for Time Inc. employees to carry in their wallets about the mission of Time Inc. Right? Because Time has been through a lot of turmoil in the last few years – and that will continue – and it’s very funny that that’s how they want to have an incentive for people to care about what they’re doing. I don’t think that I’d go for that either. And not a big legacy business. I need the more modern, the more—things are changing right now kind of contemporary.

How have you seen Silicon Valley and its culture evolve and change since your earlier years in the industry?

Well, the biggest thing by far, by far, is just the influence of the idea of this place called Silicon Valley on the world. Where I came into it when it was about the power of the personal computer, and that certainly was a powerful thing, to get away from the priesthood of the mainframes and all that. Putting the power of publishing and ideas and creativity in people’s hands – that was the beginning. [Since then] we’ve taken giant leaps forward from the beige plastic thing on the desk. Technology is now so much more pervasive in everything in the developed world and even, frankly, in the developing world, in terms of mobile devices.

When Wired magazine launched, Louis Rossetto wrote this opening about how we’re in this era that’s equivalent to discovering fire. It was that dramatic. I understood it then, and he was right. But now I feel like you just can’t explain the world, a lot you can’t do or understand or explain without some part of this world of technology that has developed in Silicon Valley. And obviously not only physically here – this is a notional place. And I’m in the middle of it.

Over the years I’ve had to host any number of delegations and tour groups – I think I was mentioning this last time – from around the world, who want to see Google, they want to see Twitter, they go visit Facebook, they want to see Apple. They want to understand Stanford, they want to understand this place and what it looks like, what people are doing, and how they might have it where they live in some way. And they mean the physical spaces and the offices, but they also mean the intellectual heft and the money and the dynamism to build great new things and have the ability to fail and like all of that.

Mostly, in a certain way, they can’t. If it’s like a government ministry wants that, they really cannot do that [governments can’t mandate innovation]. Some of it is about a free market, some is demographics and education levels, and all these things. But they want it because it represents so much success and promise and all the wondrous things coming out of it. I admit I like being in it and not in a sort of pale version of it.

Anyway, I do feel like [what Silicon Valley has produced] has changed the world. Probably within the last 10 years, my totally non-technical friends, people who work for nonprofits, are social workers, teachers, completely not connected to this world or even actively disliked either business or technology – they all got mobile phones, and typically got on Facebook, have an iPad or use FaceTime, or maybe their office moved to the cloud or they use Amazon…. They look at me like, “You’re at the sharp end of this thing. You were there first, you know all this stuff; how did you know that this would turn out to be this way? We’re coming into it late.”  Of course I didn’t know, but ended up being in the swim early. Now it’s such a given that people are using devices and services, technologies that none of us dreamed of ten years ago, in a mass market.

I’m curious to know if you’ve had mentors or people you’ve looked up to for inspiration? Or even people who were really pivotal in your path to where you are today?

Well, the most direct one I can point to was the guy who hired me to work at IDG at PCWorld and Macworld magazines. He came, himself, from a publishing background, as in a small town newspaper in Nebraska. And he’d stumbled into these early computer magazines. His name is David Bunnell. He lives in Berkeley. And he was the guy who was my board member when I was at a non-profit who hired me away to come to IDG.

There couldn’t have been a more stark “I’m going to show you this new world and change your life,”  but that is what happened. That was a turn in the road. So he was a mentor in that he made me feel like I could fit in and learn all this stuff where it was a totally foreign world to me. He made it seem like, “It’s no big deal and I like you and have faith in you and you’re fitting in. It’s all going to be fine.” That was the kind of mentoring he did. “Come along for the ride with me.” That’s probably the biggest, clearest marker in my life.

Then another one for me would probably be my friend, Tom Rielly, who now is the director of the TED Fellows program for the TED conferences. He’s worked for TED for ten or more years in New York, but I’ve known him from my early days at the IDG magazines, simply because we had mutual friends, and eventually met, because of that. He was a nerdy young man, younger than I am. He was a classic early adopter. He worked for some of the early Macintosh companies as a marketer. He was always out in front of all that stuff, and I just watched him and hung around with him. It was so much a part of his nature and his style. He’s a natural marketer, and he’s a very infectious person. He’s smart, and he’s funny, and you want to go along wherever he  is going. That was almost 25 years ago. He had a circle of friends, almost all of them were younger than me. But again, there was no sense of, “You can’t be here. You can’t come in.” I think that it was fun. It was fun to geek out, to get the latest thing and wait in line at Macworld or the Apple Store when the that eventually came along. Now looking back, it reminds me when I was a young teenager I was early into the Beatles. We would go to the record store on Tuesdays when the new shipment of records came in and I was among the first to get the albums. [chuckles] It’s not that different from waiting in line at the Apple Store or to put in your order which I’ve done at 12:01 am when something new is available.

Did you have have support networks in place early in your career, and where do you find them now?

Not in any formal, professional way. No, I really didn’t. I just had friends. Now I know I’m a natural networker and connector. And I think I just had friends here and there that I liked wherever I worked and so on. There were older businesswomen, but they weren’t like me. I was a misfit to a certain extent, and I’m a bit of an outsider. So I didn’t see myself having sort of a straight job where I could go to the next level in the marketing organization or something like that. So no, I had an informal network, which is very important – we were all sort of making our way here and there in kind of roughly parallel paths. The fact is I was older than a lot of them, it turned out, in the technology world. That didn’t matter as much as over time, I found that I had among my friends people I looked on as a brain trust – who I could get advice from about office politics, or which companies were better, or the way to cast my own role or something like that. But it was just kind of a situational grid of people more than any kind of model or mentor.

Did you work alongside many women earlier in your career? Where have you seen them go?

I have worked alongside women since my time in San Francisco began, which is now 31 years, yes. Typically again we’ve been in sort of parallel-ish roles because the higher you go the fewer women executives there are, that’s certainly still true in technology with a few exceptions. I’m in an odd position because of what I’ve always been interested in doing – not business side operations meaning sales, or finance, or that sort of thing. And I’m not technical, but neither am I HR, or PR strictly speaking which would have been traditionally women’s roles. Right? I’ve been in in-between positions. But I’ve always had women friends certainly, and women colleagues scattered throughout in related roles. At Twitter, for example, I have a good friend in consumer marketing, a different team, but, we certainly are each other’s support system and are professionally aligned even though our work is different.

What are some of the things that you’ve seen yourself and people close to you, women close to you in the industry experience over time?

Age plays a positive factor for me, because the fact that I’ve been older all along through this period. There’s a whole world [now] of women in engineering and technical jobs that’s growing and getting a lot of attention, which is great. There are other women, often in sales and marketing, other functions. And there’s a little bit looser aspirational [efforts there]. I drop in on them – they want to know how to negotiate better for a salary, or how to be the only woman in a group of men, or something like that. They want to know how to be taken seriously. And I am taken seriously. Whether or not I have a lot of clout is a whole other story, but people don’t dismiss me as an airhead or a little girl, so that’s an advantage of age [chuckles]. I can play the age card to my advantage to a certain extent. And I think [these younger women] are finding they want to make their mark, want to figure out the politics and how to self-promote because that’s not a normal thing [for women]. And I do understand all those things, though I don’t feel like they’re my fights [at this point]. And by the way, I’m single and I don’t have kids. So, I didn’t have to worry about that either, and these are very real things that people go through. Some of my women friends at work who are moms or have young kids or take maternity leave develop bonds and connections for support that are great, and I’m not really part of that. I’m glad they are doing that. Some of it like I say is age related, where I don’t have to worry about some of the same things that they’re [dealing with now].

So you come from a blue-collar background. How do your friends and family feel about your life in Silicon Valley and how far you’ve come?

Well, my parents are gone now. My mom lived a long time, and she came to visit me at Google once. She lived to be 92, and the fact that her life spanned including going to the Google campus was kind of amazing. I don’t think she ever really understood what I did there other than work in technology, and it had to do with writing and editing and whatnot, but she knew I was successful. That was satisfying to her for sure, that I’d grown up and I bought a house. That was kind of the extent of it, honestly. I did once buy her a Mac. Interestingly, she had to learn how to use a mouse because she spent many, many, many years typing on a typewriter, so this weird extra thing that is this object, and that’s how you touch the screen. She got it, but it was a bit of a struggle.

Anyway [to family and friends] I think I’m considered interesting. It goes with the things I was saying earlier: People with absolutely no connections to this world, know a word like “Google” or know the word “Twitter” or know Silicon Valley or San Francisco or the Bay Area. They don’t know necessarily what I do, to them all of that symbolizes success. “You’ve made something of yourself, that sounds important, we’ve heard the company names.” Right? Even my friends from college, for example, who are more sophisticated than that, but to virtually all of them, I’m the one who ended up in business. Funny, because we were all hippies. And I turned this corner, not with a plan to do so.

You mentioned that a lot of people come to you for advice on how to get into tech.

I wrote that post on Medium about getting into tech for a couple reasons. One is I’ve known a lot of journalists over the years; I love journalism and reporting. I’m a big newshound and I just like the field, even though I didn’t really do it myself. I’ve gotten to be friendly with a lot of reporters and editors, especially from the tech world. They knew me as someone who was not a flack working in PR, and someone who appreciated their world. As the tide started to turn for the news industry, say in the last five, six, seven years in particular. Magazines were the first to go. Newspapers are in trouble. So some would reach out to me and ask, What am I going to do? You don’t seem to have sold out to the dark side, and you have a corporate job that is successful – like how do I that? Should I do that? At Google especially I got a lot of, “Should I apply for this job at Google? What’s it like?” Because they knew I’d had some journalism in my background, I’d been a freelance writer, and I wasn’t a spin doctor type, and neither were my Google PR friends, so they’d ask, what it would be like if I were to turn the switch.

And then, more recently, I would just get a lot of referrals: People would say, “Hey, my friend is moving from New York, and they had an old media job, they were an old media executive, now they’re coming to Silicon Valley, what’s that like? And here you are, you live in that world.” So it was the combination of those two that led me to feel like I could codify some of this for people. If they’ve been executives and they expected a lot of traditional executive treatment, they weren’t going to get that in these younger companies and startups. If they were reporters who prided themselves on being kind of lone wolves and getting the byline, that would be over. You have to be more collaborative. I thought I’d put it together in a post. As to why I get referred to people, I think it’s just that I’m pretty approachable – people have always said, “Hey, you are a nice person can I introduce you to someone who would benefit?” I’m interested in hearing people’s stories and what they’re thinking. I really like connecting them, “You need to talk to someone over here who had a similar experience.” It’s like pay it forward a little bit and spread it on.

I’d love to know your thoughts around diversity and retention in tech.

I think I just love—I’m a technology optimist, and I’ve just seen so much incredible change in my world anyway, and the developed world again, in the last x number of years. I wouldn’t want to not be in something that is that fast-paced, but I do hear from friends sometimes a quality of life thing, sometimes cheaper place to live than the Bay Area, which I understand. Sometimes sort of like, you know what I had breakfast today with a colleague of mine who’s maybe closer to my age than some, and he said, “I feel like I’ve put in my 20 years here working at different companies, and I think I’m interested in commercial real estate, or something completely different, as another thing to do, that I’m thinking about.” I do hear all these things– I feel like there’s waves of people continue to  technology, Silicon Valley, the Bay area, take your pick of any of these. Because of all the mystique and there’s still a huge draw for people coming in. The question is, are there enough sort of hold overs and veterans to mix with them to make it interesting and valuable, as some other people leave. And some of them don’t leave, by the way. I’ve known very successful people who really get into philanthropy and social causes and social entrepreneurship and that sort of thing as well. That may be more of a function of having been in this business and being successful enough that they’d want to do that. But, it’s not wholesale either way. It’s not like people are leaving tech in droves. It’s more, I think some of it is situational and geographical, and some of it is, yeah sure. I remember in the, what, it probably would have been the, maybe early 90s. I remember the phrase then was Microsoft Millionaires, because after they went public, whenever that was, probably in the 80s, I remember reading about people would make like, $2 million, and they’d quit their job at Microsoft and open– they create a non-profit. I think the guy behind Room to Read was somebody like this. And now, it’s interesting. It’s possible to do, probably you’d have another zero attached or you’d want more money before you did that presumably, because the cost of everything has gone up. But, I don’t know, even the TED Conference is an interesting place to look where there’s a world of people who come there and I’ve gone for so many years. I see there are true entrepreneurs, there are true start-up people and technologists who may be successful, but who believe in the power of technology. It’s interesting, by the way, to see the number of very successful—mostly guys from Google who have taken their money and put it into something like a health thing [laughter]. very cute, very nice. You know, they move from like search technology into something they didn’t know anything about that has to do with the genome or something like that. And so, I don’t know, I’m often [crosstalk].

Where do you see yourself in 5 or 10 years?

I still want to be doing the kinds of thing I’m doing [now], just more for myself. I’m on a couple of non-profit boards, and there have been interesting learning situations there. I think what I continue to like is the variety, the interesting mix of people, the mix of ideas and conversation, some high culture, some low culture, some in between. I like the intellectual stimulation. I’m a humanities person at heart. I’m not going to go to a generic startup, but I don’t mind helping some [of them] with the notion of what’s their culture, how they communicate with each other, and other things that I can do for them, because there’s just a world of interesting ideas and new ways to do things. I’m still too much of a generalist, and too much of a humanities person, and [have] hippie views about not wanting to commit to one thing. Because that was always sort of a credo of being a hippie: “I have all my options open, everything is available to me.” It’s not true when you get old, it turns out, but there’s some part of that spirit that I like still.

What lessons, from a high level, have been most important to you over this time, that you would share with folks hoping to either join tech or stay in tech long-term?

It’s really great to have an appreciation of where things have been, and where they are now. To have a sense of history and trajectory about things, because I think you enjoy more knowing. With my older friends, we can geek out about remembering when fax machines seemed like a good idea, when they came in, or when we used to have, I don’t know, a Syquest drive for backing up stuff. Whatever it is, something that seems so absurd now, and is only from the last 20 years. It’s really fun to be able to marvel and appreciate this incredible arc that is within a lifetime. Within even a portion of a lifetime. It’s amazing, to be swept along, whatever your company, or your business, or technology reference is. That to me is worth it.

But you really only get that sense of appreciation over time. Another notion is that so many of these things have a big impact around the world, even if it’s something really simple. Like when Twitter started, it was designed around the small text message limitation. That was on  purpose, to be able to do it in places where you only had SMS. That sort of thing is compelling for people who are in, or  want to be in, these kinds of world-changing businesses. Like a Google search, that search quality is so good, and continues to improve, and no one’s work is done. You want to keep on and look the impact this thing has had. I think, that’s a draw for people, as well as [giving] purpose and meaning. Another draw would  be the kind of pace you get to see, and live with, in the technology world. I could not live without a draw like that. Don’t take that away from me!

Okay. Well I was born in New Delhi almost 50 years ago. I grew up in Delhi, went to school in Delhi, went to college in Delhi— pretty much stayed with my parents until I left home. I left roughly 25 years ago to come to America. The reason I wanted to come to America was very simple. I wanted to be a journalist in a big market and it was a weird idea that I could be. A lot of it was also inspired by my early brush with online communications through CompuServe and reading a lot about ARPANET and the information superhighway. A part of me said perhaps that was going to be the biggest story of my life, and I should figure out a way to write about it.

I had no idea why that thought clicked in my head, and I still don’t know, but I think deep down I’ve always understood that communications are a fundamental human need, and the networks were essentially fulfilling that. But I wasn’t really clear as to why I was thinking like that. It just was something which went “click-click” and there it was. That was about 25 years ago so I’ve lived in America half my life and I’ve lived in India half my life. I traveled a bunch before I got here. I went to England, I went to parts of Europe and here I am. That’s my story in a TL;DR version, though growing up in India was interesting.

I come from middle-class family. The middle class in India is very different now than it was when I was growing up. Middle class India then was very different than middle class in America now or in fact what it was back then. My mom, dad, and my grandfather all worked to make sure that there was food on the table and clothes on our back. We all lived in a very small house. That included my father’s sisters and my aunts, me, my mom, my dad, and eventually my sister and my brother, my grandmother, my grandfather. The house was about 70 square meters. It’s a tiny place—but I think our parents will call it big. We still live in the same house back home, like we haven’t moved. And still— whenever I go back I sleep in the same bed I slept in as a kid and it’s cold in the winter.

I went to what we call private schools in America—equivalent of that but not quite because—it wasn’t really the top private school or anything of that sort. It was just one of the schools you had to pay to attend. Public schools there, like public schools here, are free and but they’re like public schools everywhere. My mom was a teacher in a public school, but I went to a private

school, and then I went to a college called Saint Stephen’s College, which is one of the better colleges in our country. It’s around 200 years old so it has some history behind it. I never really wanted to be there, to be candid. I just felt I was going to college because that’s what everybody does and that’s what my parents expected from me.

I really wanted to be a journalist. I knew that a long time ago. I was almost fourteen years old when I knew I wanted to be a journalist. I just didn’t have the right phrases for it, but intuitively you know what matters. I had no guidance on how to go about doing things. My whole life has been a bit self directed in that I have made decisions, and figured out what to do after making those decisions. More or less, it’s worked out. It’s okay. That’s life.

When were the earliest moments where you knew that you were interested in tech?

I learned how to program in India back when I was like 19 or 20 years old. It was like BASIC, etc. mostly because my mom said, “Yeah, it would be good for you. You should just study this rather than trying to figure out a career.” So I did, and I wanted to be an engineer at one point. Then I realized I don’t want to be an engineer. The thing which I absolutely loved was writing and through writing, I got a chance to meet a lot of interesting people.

Around age 20 is the first time I understood that I liked tech. I was writing about fashion and movies and sports and I was all over the place. The thing I loved the most to write about was Formula One. Unfortunately there was no Formula One in India at that time, so I just had to read about it more than anything else. I was pretty nerdy about that stuff. It has been about 27 years now since the first time I wrote about tech. It was about local companies in India who were doing tech, like ATN etc. It was pretty basic at that time. The world is very different today.

Walk me through some of the early years. What was the impetus that brought you to the States and into the blogging world in American tech?

As I said, I was very intrigued by the whole idea of ARPANET and the information superhighway and CompuServe. This idea of of online communication. Part of me intuitively knew that it was going to be something important, and it also dovetailed with my idea of, “What if I just move to the US? This would be a good thing to write about.” I also wanted to live here because I always felt that I needed a bigger playground. I have these goals I set and it’s like, “Okay, I’ve met this, now what? What do I do next?”

Most people like to have traditional things like family and kids, and all those things don’t intuitively make sense to me. Spending more time on things I like to spend time on was very important for me. I think it was all in my head. All of it was reading. I used to read a lot, and I still read a lot. The more I read, the more I learn how things are, and so that was my path. I came here and after I moved, I was like, “Oh my God, this is not going to be that easy.” It wasn’t that easy. You make a decision, you’re here, and you’re kind of stuck with that decision for a while.

How did your family feel about you leaving for the States? What plans did they have for you and what did they want you to be growing up?

My mom and dad would have been very happy if I became either a doctor or an engineer. And I don’t really know what I would have been if I stayed there, but I knew I wanted to be a journalist a long time ago. I wasn’t very clear how to go about doing it. I always had an opinion about something. This was always the case with me.

Yeah. So, let’s talk about the earlier years of your journalism career like tech blogging in the 90s.

I didn’t start blogging in the 90s, I started tech blogging on December 13, 2001. Specific date. Before that, I used to write for Forbes. Before that I was doing a lot of shit work for three years or so—doing a lot of freelance. From there I went to Forbes.com. From Forbes.com I went to Red Herring. From Red Herring to Business 2.0. When I was at Red Herring in 2001, after September 11th happened, I wanted to move back to New York. When I moved back to New York I realized that I was working for a monthly magazine and I had a lot of time and a lot of information which I wasn’t really doing anything with.

At that time the internet start-up ecosystem had collapsed and so there was very little technology coverage. I had been reading and collecting my pieces on my personal website. I used to occasionally write a newsletter or opinion pieces except they were were not really blogs because they were just long pieces. I would write them and publish them as an email, and then put them back on my website as an archive. So it wasn’t really a blog but I just tried Blogger and the like until 2001 when I went all-in. I started linking to whatever I found interesting and commenting on it. So that’s how my tech blogging career started.

In doing so I may have sparked something in a sense. I was the first guy who started reporting on original tech stuff, new stuff without really realizing that I was the first guy to do so. But I started writing—about 95% of what I did on a daily basis had no takers because the magazine could only publish one or two stories a month and about 95% of the stuff fell on the floor. I just started putting it on my website and that’s how it started and slowly grew from there.

Yeah. Walk me through what, in the 14 years since that happened— what have been some of the most exciting moments of your work? What are the things about it that really activated you and what were the things that you were proudest of?

I don’t know if there is any specific moment that I can say that was special. I just say the whole thing has been special. I think from the day I started until today that I might have found my art form, right? It was not traditional journalism, it was not writing news. It was a little bit of opinion. I think my whole past was building up to me being a blogger. Because when I was a younger guy, I worked at an Indian newspaper— magazine called The Sun. It was a teenage magazine and they published a lot of pop music news and Hollywood news and my job would be to read 100 or so Hollywood magazines and pop music magazines and listen to music charts from short-wave radio and figure out a way to write about it. Essentially, it was not really reporting, it was like rewriting a lot of the stuff which was done and putting it in a little bit of context, so it was essentially a form of blogging.

Then I worked at Forbes, where they teach you to write succinctly, very short. The biggest lessons in the 90s from Forbes was if you write 1000 words, you can write it in 500. If you write 500, you can write 200. You start to look at it and you’re just like, “Okay.” You’re trained to rewrite, trained to write tight, and trained to ask tough questions as a reporter. All of these things came together as a blog format for me, in a sense. I found that that was my form. There are very few people who I think do this, natural-born bloggers. Dave Winer is one, I think Michael Arrington is definitely one  That’s why he was so popular. Most people don’t quite understand that. To some extent, M.G. Siegler is one of those people, and I was one of those people. Arianna Huffington is one of those people. Even though she has some news, she likes it in a way which has got opinion in it, has a lot of context with it.

My past brought me to my form, which is why I have struggled to write a book, mostly because I feel, this is how I like to write. I don’t know how to write a book. I like to read a book, and I find myself saying, “Get to it, guy. Why are you taking so long?” 85% of books are so badly written. I like the idea of not having finality to what I have written. Most people, their books are very final. It’s like, “Okay, this is it.” Things change. You look at a guy like John Legere—the guy who’s running T-Mobile now—his past is pretty colorful if you go back to his Global Crossing days, and who he was, and who he is. Not the same person, and yet, the same person. But if he was a hustler trying to get money out of big companies then, and now he’s getting interviewed from individual investors— the objectives are different, the thinking is different. So for me, I think this was my forum. And I don’t have any specific moment. I have things I’m proud about.

I was proud to say goodbye to Steve Jobs in public. I was very proud to write about Skype being acquired by Microsoft because I spent ten years writing about Skype. I finally got my big story on Skype. They were always going to bigger publications. I like the fact that the thing which made blogging and my independent life as a writer/founder great was that we would do stories which we’d notice before everybody else. We were talking about the “Cloud” on my blog in like 2005 and now it’s all mainstream. Same as with data— data was something we were writing about in 2006. When GigaOM came about, we wrote about future of work and online video. I’m proud of the fact that we were always ahead of the curve on everything, but I can’t pick a single story. I’m very proud of all the people who came together. I think that is the lesser known topic on the history of GigaOm, the amazing talent who came together.

I think we were all people who got better because they worked with each other. I think a lot of places have star reporters and star writers and I think we were the star team. Each person made the other person 10x better. That is what I’m proud of. Soon it will all be forgotten, but in my heart, that’s what I think. We were a team that worked together for a very long time. The core team was pretty tight editorially. For me, that was the biggest, proudest part of my blogging per year, as we went from individual to a team. We had a lot of content. I heard a lot of stories. I interviewed a bunch of people. I wondered what was going to happen in the future. Even I’ve stopped doing aggressive writing like I’ve used to, mostly because my day job now is not being a blogger; it’s something else. I don’t know if I answered your question. It was a big ramble.

You’re doing great. What’s it been like transitioning from journalism and blogging to VC?

Very different, right? Take a blogger and a journalist and no matter how much access you have, you’re still outside looking in. Inside looking out is very different. I think it is a much tougher realization I had when I became full-time VC. When I was I was part-time, it didn’t really matter as much, because I was traveling the two worlds and so it was pretty easy.  But now, being full time makes it much, much more explicit. Being an investor is a different kind of work and different kind of stress, as in it needs a different kind of mindset.

Do the same things that excite and activate you as a journalist, excite and activate you as a VC?

Yes. The core of why I’m drawn to it is technology and change. I think the motivations are different. Motivation as a writer are to tell a great story and then move on, and it’s like a motivation. It’s like having a flame, whereas investing is more like being in a relationship. You are with the company for a very long time, so you actually have to be very certain to commit when you make an investment in a company. Because it’s not an investment in a company, you’re investing in a relationship with the founders, you’re investing your time, you’re investing your emotional energy into something. And that leaves a very little time for all the other stuff, because that is the vector with which you look at your investment, whereas the  journalism world is a little easier. You don’t have to worry about running out of money. You don’t have to worry about having a tough conversation with the founder, trying to tell them that they’re screwing up or et cetera, et cetera, et cetera. You know what I mean? That is what I find is different. It’s definitely different kind of challenges. I have no problem with both. I still like to write. I want to write more, but I want to invest and find more companies as well. I think the challenge is that if you’re a journalism you can be more empathetic and more kind to people making mistakes and if you’re an investor, you have to be very direct with them. A lot of people don’t like it when you’re too direct. I made so many mistakes and I learned a lot from one of my board members who’s also my partner now, is John Callahan. It’s like, you can be direct and yet be human. So I aspire for that now. That’s like my way of dealing with it. It’s definitely an interesting tradition.

How do you think the culmination of your life experience, like growing up and all the years that you spent in journalism and blogging, how do you think that affects the way that you approach your work now, and makes you unique as an investor?

I think because I grew up the way I did, I’m grateful more often than most people around here. Because my first was equivalent of 13 dollars in a month, so for me this is like I won the lottery of life. I feel that gives me a little bit more— I take a more philosophical view of everything. I think that’s been my approach, and I think a lot of it is because of my boss. I don’t have time to play games and all those things. You know what? If your aspiration in life is to only make money, then you can do that. I have a different aspiration. My view is that I think technology and change are important to society, and we should be thinking about that. I look at things which are important. I look at science, I look at technology, and not look at opportunistic pointless things to try and make a difference. Everybody says  if you want to invest by making a difference, and it’s like, I don’t know. I mean, like, I like to think about it from a more philosophical standpoint. Like, are we really making a difference? Because most people think of it as a deal. I think of it as an opportunity. I think that’s — like, if you had to just sum it up, that’s… I look for opportunities, people look for deals. That’s my way of putting it.

I love that. Let’s see, you’ve seen tech go through a couple of cycles now. I’m so curious how you’ve seen it change for better and for worse, and particularly culturally, and how you feel about the state of tech in 2016.

That’s a pretty broad question, so you’ll have to slice it.

Let’s slice it then. How have you seen tech change as a culture since 2001?

I think technology is now at the heart of everything. I kind of joke about this, but I think Silicon Valley has become the Babylon of the twenty-first century. And are we doing things right or wrong? I’ll let other people be the judge of that. I think we have a moral responsibility now I don’t think Tech ever had to think about it before. Like 2014 onwards I’ve been writing consistently about this. I think our moral obligation to society at large— society that can make decision based on what the future is right now. I think that is something that we need to be thinking about. Whether it is Facebook, Twitter, whomever— that’s the most important thing. I think Apple is standing there on it’s own and making a statement around privacy. And they’re not saying there’s privacy in encryption. It’s bad for business. And maybe it is and maybe it’s not, but I think it’s bad for humanity. Like if you are— if there are microphones and cameras in our homes all the time, do we even have a modicum of privacy? Are we human then? Aren’t we all living in a zoo at that point? It’s like, what’s the point? And I think there is a moral imperative to all technology, and I think it is time we better start talking about it and acting on it, right? That’s how I think about technology right now. That is the most important change. 2000, 2001—it was all about big companies and a few thing here and there accessing information on your website. Now we are squirrelly. Everything is happening because of tech now. The guys in the Middle East is fighting with the west though Twitter devices. You have spying happening through the Internet. There is a story on the US hacking into Iran’s infrastructure incase there was something weird going on. All those things tell you that every step you take, you use a phone to call in an order, you use a phone to order stuff from Amazon. There is very few things you do now which are not technology. Right? And so there is a moral imperative. I think that’s the biggest change. I think I wrote a piece in 2003 about Redheaded magazine shutting down and pointing to technology becoming completely consumer and pervasive in every way and that was the future and that future is here now. That’s technology today.  I think that’s where we are, right. And so I think it’s cool to be part of it but it’s important to be thinking about the larger, moral impact of what we’re doing here.

With that in mind, how do you feel about the current tech ecosystem right now?

Well, I don’t know about tech ecosystem. I feel like there is many, many ecosystems and there are some parts of the ecosystem which are somewhat unsettling and disturbing because we’ve never— I don’t know. I think there are some parts of it that I don’t like. I think— I’m trying to figure out how to describe this.

Take your time.

There is a cultural aspect of it. And we don’t think before we speak. I think culturally, we’ve come to a point where we shoot before we ask questions and I think there’s a little bit of a Wild West mentality in the ecosystem. I think there needs to be a little bit more thoughtfulness. I think we also have challenges around intellectual leadership. There is guidance which takes into account the moral and societal obligations of technology. There’s a lot of talk about diversity in the Valley. And my view is not just as diversity. It’s diversity by race, diversity by gender, diversity by economic strata. Everybody just talks about their point of view without thinking that each thing has an impact on the other. And we’re talking about these things without a larger context of where our plan it is headed. It is good that we’re talking about diversity, and it’s good that we’re trying to— Numbers are only like half the story. It’s like, we’ve got to think about this bigger—just can’t be about the numbers, because we need to be about systematic change. I like what folks at Facebook are trying to do. They’re not talking about, “Let’s fix this problem.” It’s not an engineering hard fix. This is like, “Let’s develop a new system which is more open to the ideas from more people. And I think that is a longer process. It needs patience. It needs consistent education on all sides. More importantly, it needs action, not reaction, right? I’m very proud of the fact that my favorite part of GigaOM was that we had a huge number of employees who were women. And they were all— I then listened to all of them because they were just smarter than I was. Collectively we got better because of it as a team. It was not because I was playing some game of, “we should have more people.” It was just we should have more great people and they just happen to be of a different religion, or a different color, or a different gender, or a different race. And I think that diversity in the ecosystem is very important. It makes the ecosystem more resilient. It’s a scientifically proven fact that we need more varied people in the system. I don’t know, I look at myself as an example and it’s like, “I shouldn’t be here, but I am.” And I definitely am different than most people I know here. I know that, I have my own way of looking at the universe. I’m okay, but that’s how I see. That’s the ecosystem needs to evolve from better things— to be looking inward looking to a more outward looking ecosystem.

You know one of the things which I actually, what my mother is responsible for, is she worked very hard to put me through college— through school and college. Just like my dad, but my mom worked extra hard. She did tuition and stuff like that and took her own extra money to put the kids through college. And I think for me that has had a much more of a lasting impact. It was like she’s no Sheryl Sandberg in terms of being famous and everything, but I find her more inspirational than Sheryl Sandberg just for that reason. She lived with in a society which had very little room for women who worked and stuff like that and she managed to put me where I am. I think that’s very important for me. It had a way longer— like that’s what I mean the long term it that I saw her do all those things and I realized, “Well, you know, she’s actually pretty smart.” That’s why I am here, right? If she hadn’t pushed me to study, then pushed me to go to a better school and a better college and paid for it, I wouldn’t be here. That kind of tells you everything, right? That’s how you should be thinking, because she was very different than my father. My father was not that person. As a child, you learn a lot about your people from your parents. And I think, similarly, when I came here, more editors I encountered who were open to me, the more open I am to other people because of that. You only learn from people. When I say we have to take the long-term, let’s not focus just purely on numbers, but focus on actually inspiring people to think about the subsequent generations. In my case, it was my editors. I got some really great editors. They couldn’t give a shit how funny my accent is. As long as I got them the story which mattered. There were always positive. And I think there’s a lot of people who would not, and I remembered that. And I remembered to avoid that mistake. Half like New York establishment— I never got a job offer from any of the big publications. Forget job offer, I never even got a call back from any of the big publications. Even today. For me, the path has been on my own. And that’s the challenge of our ecosystem. Is that most of the thing we will need to do is to inspire people to make right decisions five years from now. And we had to start a systematic change, not just numbers but also make people think different.

Where do I want to take it from here? I’m curious to know what your priorities are in 2016 and what you’re working on either for for work or for yourself.

Work things, I’m focused entirely on finding some interesting new companies to work with. I’m interested in writing more regularly. I promised myself that I would write every day and so far I’ve written— it’s 50 days into the new year and I’ve only written 30 times, so I’m falling behind on that [chuckles]. That’s it. Then I have a personal project called PI.CO, which is where I interview interesting people. I want to interview 25 interesting people this year. So far, so good. I’m on top of it for that.

What, as a VC right now, what are are you looking for—it could just be conceptually—in a company that you’d want to invest in in a year like this?

I don’t care what the market is doing, I look for companies which are using technology to solve a great problem. And my preference is for companies with technologies which are more behind the scenes—sort of like networks, and sensors, and stuff like that—but nothing has changed for me. Last year I made only three investments and in the year before it was two. So I’m not rushing out to spend a lot of money. I am looking for a company that I would like to work with. I look for opportunities— and my personal belief is that there is going to be need for software which helps us live better. Because as humans, we are soon going to come to the limit of our ability to live with the world around us because of data and technology. So we will need another layer— just like Google helped us figure out how to find things on the Web, and Facebook figured out how to rearrange our relationships,  there will be new software which will allow us to just exist smartly in the universe and I’m interested in that aspect of technology. People are talking about artificial intelligence and stuff and my view is before we get to the Skynet, we will get to augmented intelligence where we need the software to help us make better decisions. So that’s where my focus is right now.

And then, as far as Pi.co, what kind of people do you gravitate towards the interview?

Well, a lot of photographers. I think photography, visual culture is going through change. I’m going to talk to a bunch of scientists in this year. I’m interested in talking to more in a smaller fashion people, trends, like you know, people— I just did the piece on this young blogger called Julie Zerbo, she runs the Fashion Law and she writes about fast fashion and stuff like that. So I’m interested in that, maybe I’ll interview some economist and stuff like that. I mean, I’m just looking for people who are at the nexus of today and tomorrow, people who are predicting the change. That’s what is very interesting to me.

And I don’t know, for some odd reason, I like talking to photographers. I might start a Twitter feed just linking some of my favorite photography oriented articles and stuff I read. I read a lot about photography. And I don’t think of photography as just photography, but more as what other possibles of camera sensors everywhere.

Okay, last question. What advice or major lessons would you have to share with someone who has a similar background to you and is hoping to get into tech. What advice would you have for them based on what you’ve learned about yourself?

I think every time somebody said no to me, I tried to figure out why did they say no. No is fine, rejections are fine, but you use the no to calibrate why. That means having to take no graciously. I think it’s pretty painful to say no to somebody, as much as it is to take a no.

The advice i have for anyone, whoever they are. If you believe in something, you’ve got to go for it. Don’t worry about the consequences. Don’t worry about the financial outcome, or how famous you’re gonna get, or how poor you will be. If you believe and you can’t seem to do anything other than think about something, you’ve just got to keep doing it. I think the universe has to follow. What’s the point of living if you don’t chase what’s important to you? That’s how I see it.

I grew up in Connecticut, in West Hartford. I hate to use the term tomboy because that’s really come out of vogue these days—but I was kind of a rough and tumble little girl. I was really into being outside, and doing imagination stuff, and running around with the boys on my streets, and that kind of translated well into…male-dominated industry is my whole life.  

Did you have any inclinations as a kid that your would end up in something techy?

I didn’t. My main goal was to go to college, and I only applied to one: Emerson. And to get a job working in the audio field. It was technical, but it was really more related around the audio industry and live sound. And it wasn’t till I moved out to San Francisco, kind of on a lark, that I realized I could combine my love of technology, which I liked as a fan, and my love of audio, to kind of build this strange career that I’ve made.

Walk me through the path from production to hosting to be a well-known nerd world media figure.

I went to school for audio and radio production, but I was really a tech; I loved computers. I loved everything about the early internet. I’ve been on the internet since the CompuServe/Prodigy days, but I never really thought of it as something I could do for a job. We had computer classes at school, but it wasn’t that time yet where people were really like, ”Oh, yeah. You should be a programmer. You should be a developer. Like this is something that you could do.” It was like, ”We’re going to build stuff in CAD or we’re going to take typing classes.” So it was a very different kind of atmosphere back then.

So I got to San Francisco—I moved out here with two girlfriends, and we shared a tiny apartment and I lived in the living room, and slept on a mattress on the floor like everyone does at some point in their life. And I was constantly searching Craigslist for job postings. One day, I found one for an internship at CNET. At the time, I was temping, so I was taking any work I could get. It was a very low-paying internship at the time, definitely not something I could have lived off of. But it was that opening door, that opportunity to get in on the ground floor.

So I put my resume in, got the callback, and went in for an interview. I showed them I could edit audio and work production, and got the gig. At first, it was very boring stuff. It was like white papers and audio from board meetings and things like that. I was much more interested in the consumer tech side of things. They eventually needed someone to produce and edit one of their early podcasts, Buzz Out Loud (a daily tech news show hosted by Molly Wood and Tom Merritt), and I just fell in love with it.

I jumped on the chance and found after couple of weeks that I had a really hard time keeping my mouth shut when they would start getting into conversations about the news of the day in the tech world. So I started talking, and I eventually became the third co-host. Eventually, my boss was like, ”Hey, you should really give this video thing a go. We’re relaunching CNET TV. We need more hosts. I know you know how to video edit and produce so just jump in there. Write a script for yourself, get on camera, see how it feels, see if you like it.” And I did.

What shows were most rewarding for you over the course of your career?

Tekzilla on Revision3 (now Discovery Digital), was really fun for me. I did that show for about five years, and we covered everything from viewer tech support to product reviews to big segments on internet privacy.

But I think my favorite show for Revision3 was Fact or Fictional. It was a look at the technology and science in media. Comic books, video games, TV, film—how accurate were they? I would bring on guests like scientists, engineers, and thought leaders to give me the rundown on what was possible and what was just totally make believe. That’s always been my M.O.: combining information with entertainment and making it palatable and fun.

What are the most captivating things about your work? What aspects of the work just totally drive you and excite you?

Fan interactions or viewer and listener interactions. The Sword and Laser, the sci-fi fantasy podcast that I’ve been doing for the last eight years, has fans that have been listening since day one and they still contribute, and they still talk at the forums, and they still call in. I just love it. It feels like a family. It feels like a deeply nerdy family [laughter].

What have been some of the toughest parts and the biggest struggles? Particularly as a woman in tech media?

It’s been tough occasionally, and you definitely get a lot more flack, I think, for being a woman. But there are so many women in the space now that it’s hard to write them off as anomalies anymore. For me personally, my biggest issue has just been dealing with rejection, because I have tried to do so many projects. Things for TV, or things for other channels and networks, and it’s so hard to put all your passion and energy into a project just to have it brought down by some nameless faceless person on a network somewhere, sitting in a room deciding what’s going to be on TV for the next year. That’s tough and it’s something that I don’t think you ever really get used to. Each time just feels like a slap in the face.

There is a considerable amount of the population of the internet that seems to be kind of obsessed with you at times, and I’m curious how you handle that.

I think it’s about boundaries. I’ve built up certain walls of protection around myself, and if something gets too out of hand, if some fan, or listener, or viewer, gets a little too familiar, you just have to shut that down. It’s hard, because when we talk to people online we feel like we know them. Especially if you listen to a podcast or watch a video regularly, that person, me, I’m in your ear talking to you on a very personal level every week. So people feel like they know me. But you can’t always be an open book I think, and there are some boundaries you have to mentally set about what you share about your personal life.

You work in some of the nerdiest part of the internet where there’s been some aggression lately. Do you catch the brunt of any of that aggression or has it been largely positive for you?

For better or for worse, I try to stay out of it. The few times that I have jumped into the fray have been, well—the amount of shit you get is so disproportionate to the comments that you make that it doesn’t ever feel worth it. I stood up for my friend one time on Twitter and I just woke up the next morning to a wall  of responses from GamerGate people. I was just like, “You know, I’ve got work to do. I’ve got a life.”

Where do you find your support networks? Where did you find them in the beginning and where do you find them now?

I think the biggest support is probably my husband, Ryan, because he gets me. In this weird industry, it’s hard to find a lot of people that can relate to the lifestyle, especially when you’re a freelancer, and especially when you’re working on the internet, and especially when it’s a medium like audio or video. It’s a very weird experience and he encouraged me to do it. That was when we first started dating. He was like, “Go for it. You’re good at this. You should try it.”

But also other women who work in the same space, we all comment about everything, from weirdos on the internet, to not getting a gig, to not getting people to pay us in a timely manner. It’s been nice to have a community of like-minded women that I can share those experiences with.

How have you seen tech change culturally over the years or have it?

We’re kind of in this weird place right now where we’re moving away again from blogs. When I started my career, the big threats to CNET were Engadget and Gizmodo, and sites like that that were able to turn out content at an incredible rate and just really stay on top of things in a way that the old media sites weren’t really able to compete with until much later. And now it seems to be less about blogs and more about curated content and stuff that we’re receiving through social, whether it be through Facebook or Twitter. Now, everybody’s trying to figure out how to reach the most people and get the most clicks to make things viral.

Of course now, we’ve got a huge industry around on-demand products. You know, rides when you want them, food when you want it, groceries when you want them. That whole industry has really shaken everything up in a pretty incredible way. The technology is changing so fast and moving in such an incredible rate that now we’re like, “Okay. When’s the backlash coming? When’s the next backlash coming because it’s going to happen.”

If tech media were this way today, would you want to be in it? Would you feel encouraged or discouraged?

Totally discouraged. From my particular career, I would be intimidated by the YouTubers, and the Vine stars [laughter], and the people who are just building and amassing these beautiful audiences through different channels. That didn’t exist back then. I think I would still probably want to be in technology, and that’s kind of where I’m going with my next career shift. Lately I’ve been thinking about getting out of the video space and getting into more of an operational role at a company. That’s really exciting, but yeah, it kind of feels like I’m starting over at 33 [chuckles].

What do you look for in a job now versus when you started?

I actually just wrote a big post about the freelance lifestyle on Medium, that’s got a lot of traction because I’ve been a freelancer now for the past eight years. But there’s always the feast-or-famine scenario; there’s going to be highs and lows. Planning for that can be especially difficult in my type of work where you’re essentially waiting for people to need you. They have to come to you. It’s hard to schedule in advance for gigs. San Francisco’s an expensive city and you need to be working all the time. So now, I’m like, “Okay. So maybe a full-time thing.” Not only because of the money but also because of the peace of mind.

What has the hunt been like and what have you learned about yourself in that process?

The first step was figuring out what I wanted to do and where I fit. Things like evangelism and marketing make a lot of sense, but they’re not really what I’m passionate about. Now I’m looking at product management. I’m looking at working with many different teams to kind of oversee the development and creation of a product, because I love building things. I love having my fingers in all sorts of different pots, so being able to work with the engineering team and with the marketing team and sales and all the different groups that come together to build something amazing.

Do you think that you will host at all? How would it feel like to potentially leave a decade of community behind?

I don’t think I’m going to leave all of that behind. Sword and Laser is just such a part of who I am at this point; that’s not something that I have to give up. But I hope I can kind of keep some of that audience and keep that conversation going through being active on things like Twitter, and Facebook, and Snapchat. I’m still going to love the things I love and want to talk about the things I’m passionate about, it just won’t be such a major part of my job anymore.

Oh, man. Exciting times.

We’ll see!

Okay, let’s go macro for a second. What do you think about the state of tech in 2016? What are you excited about? What are you frustrated about? What would you like to see change?

It is confused as fuck right now because it wants to be more inclusive and it wants to be more diverse, but I don’t think it knows how to be both of those things. So I’m excited to see how bringing in more diversity, more different kinds of voices into the tech space can make it a better place for everyone. The more perspectives we have and the more voices we have only mean that products are going to get better and cater to more people, and that’s good for business.

Do you have any thoughts on what you would like to see change in that realm in the next few years?

I think I’m just frustrated with, like, hot takes. And I don’t think that will ever go away from media [laughter], but I think it’s especially bad during an election cycle. It just becomes too overwhelming. I love deep dives, and that’s something that a lot of sites have gotten really good at doing. That’s kind of where I see the most value.

Are you working on anything else? Any other projects for work or for yourself?

No. In fact, I’m trying not to. I’m intentionally not taking any more freelance projects after the two that I’m working on right now end. So I can focus 100% on the next thing, whatever the next thing is. I just want a clear head and a clear calendar. I’ve got a few speaking gigs and I’ve got a couple of jobs to wrap up, and then I’m going full-bore into Veronica 2.0.

I would say finding focus is a project in itself. I feel like all of last year I was trying to figure that out.

It’s hard [laughter].

It takes time. It takes time.

It’s stressful.

Where do you see yourself in five or ten years?

Still in San Francisco. And hopefully, being a voice in whatever new career path I have decided to take. I have a hard time not being outspoken about stuff, so I hope to keep communicating with people who are interested in the subjects that I’m excited about.

What lessons have you learned from your time in tech that makes this whole career switch not so scary for you?  What gives you at least a little bit of peace of mind?

People want to help. And people want to help you make it. They want to connect you to the right people. They want to start the conversation and it feels really good to know that there’s people on your side. This is the one place where you could say you wanted to do anything and people are like, “How can I help?” And compared to where I grew up or most places on the East Coast or people would be just like, “Well, are you sure you can do that?” Whereas here, just not having the roadblocks associated with people just being like, “You can’t do that,” or when those are removed and people want to help, it’s like, this is the best place to do anything.

What advice would you give to folks from similar backgrounds who are excited about tech and hoping to get into it as a career?

This is the advice I always give and I think it’s still is very true today as it was ten years ago, which is that if you’re passionate about something, you should be doing it already. You should be getting blogging, making a podcast. The barrier to entry is super low now. Do videos on YouTube. Build up a portfolio of stuff. If you’re a programmer, start building things get on GitHub, publish your stuff. It’s so easy now for someone to get attention building something cool, even if they’re not a known entity, just because you can put it up on Product Hunt or other ways for you to get noticed. You’ve just got to start hustling.