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

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.”