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

I was formed in a culture clash. I’m first generation Eurasian—Czech, Filipina, Taiwanese—and was raised in a small hippie town founded by an Indian guru in Iowa. Fitting in was never a possibility; I spent my childhood hoping to be noticed for something else other than being different.

What was family life like? What did your family expect of you career-wise?

When I was thirteen my father took a trip to the east coast and brought me back a Harvard t-shirt. As the eldest of four, I bore the brunt of his immigrant dreams. Thankfully he was more of a “follow your passion” type guy than one who pushed for law or medicine.

My biological mother hails from a rural village in the Philippines and was the first in her family to finish high school and go to college. When she obtained a PhD and position at MIT, she cemented a place in the provincial hall of fame. I don’t know much else about who she is unfortunately. She died in a car accident when I was young, but even her ghost is hard to live up to.

“Fitting in was never a possibility; I spent my childhood hoping to be noticed for something else other than being different.”

My father is a kooky but brilliant underachiever, a renaissance man who possesses that rare blend of a critical mind and creative talents which he channels into architecture, art, philosophy, and poetry, and deftly speaks at least five languages. He has an anti-authority streak, refusing to work for anyone else and only at his own whim.

His lack of material success is an endless source of frustration for him, and seems to only be redeemable by his children’s. He taught us to read as toddlers and multiplication in kindergarten, and hoped that this would set us on a trajectory for life. My (half) siblings are in their twenties and are wonderful people with musical abilities, artistic talents, keen minds, and sensitive hearts. So maybe he was right.

I can’t imagine my potential career ever entered my stepmother’s mind; she didn’t care for me much as I was a reminder of the woman before her. As for my father, what I did or was didn’t seem to matter to him as long as I made him look good.

What did you think you were going to be when you grew up?

When I was a child I had no sense of future; I just wanted to read and climb trees. As a teenager I lived to travel and got any and all odd jobs to make it happen. The world was a wondrous place of beautiful landscapes and art with fascinating history, and full of unique people. When my grandmother described the life of an ambassador, I set my heart on it, and actually chose Tufts for their International Relations program. Politics lost its allure quickly though, and I ended up majoring in Anthropology.

How do you think your background and life experiences impact the way you approach your work?

For the first decade and change of my career, I helped foster communities around tech products, namely Yelp and Airbnb. I’d have to credit my childhood experience as part of a meditation community in Iowa as being the most enlightening case study on how to create a movement. I experienced first hand what motivates and inspires people to give their time, resources, and hearts to a cause; How hierarchy and different power structures influences people’s drive and sense of ownership; The ways that norms are reinforced and what happens when people act out; What to do when the message gets out of hand. Life lessons for me.

How did you first get interested in tech?

I’m compelled by how tech allows people to live more enriching, fulfilling lives. The idea of “tech” didn’t initially interest me. I used Napster, ICQ, and ebay in college, but never gave much thought to actually working in the sector. In fact, had you asked me then I was totally ignorant of the fact that from the ashes dot com bust interesting companies were emerging. But I’ve never been someone who’s motivated by contributing to cutting-edge technical developments. I often wish I had a more visionary bent.

“We landed in SF with a cell phone, $300 bucks, and a backpack full of sarongs. Every day for the first two weeks we set up shop selling sarongs on Haight Street and trolling Craigslist for opps. I went through a series of odd jobs: pyramid schemes selling office supplies, handling boa constrictors, trimming weed, data entry.”

How’d you end up in SF and in tech?

In 2004 after college I sold all my worldly possessions and moved to Bali, Indonesia. It was first put on the map by my midwife “auntie” who opens birthing centers in developing countries. After a few months traipsing around the island and bumming around on the beach with my then-boyfriend, we ran out of money. I had no interest in going back to Boston, so when he suggested we go to SF because of the great house scene (we both fancied ourselves aspiring DJs) I agreed despite having never been to the city. I knew one person from my hometown living there and she offered up her couch to us as a temporary crash pad.

So we landed in SF with a cell phone, $300 bucks, and a backpack full of sarongs.

Every day for the first two weeks we set up shop selling sarongs on Haight Street and trolling Craigslist for opps. I went through a series of odd jobs: pyramid schemes selling office supplies, handling boa constrictors, trimming weed, data entry. Until I landed a temp job at a commercial property insurance company. I was so happy to have regular income, it took me a year to realize that the agency had been taking an unfair cut.

I ended up in tech by sweet serendipity. First, I randomly saw Yelp paraphernalia on the bus and later found out that I shared a route with the graphic designer. Then I got a Daily Candy newsletter sponsored by Yelp. Being new to the city, I was curious about places to go and badly needed friends. So when I visited the site and saw several hundred people yapping about things to see and eat, I got hooked. I discovered some great places through the site and shared my reviews in return. The marketing director, Nish Nadaraja, took notice and invited me to one of the first Yelp events ever, at a place restaurant called Oola on Folsom.

“For weeks after, I emailed any and all contacts at Yelp in hopes of getting a job. They were like, ‘Can you code? No? Sorry, we’ve got nothing for you.’ But a few months after, they posted for an Office / HR Manager and I jumped on it.”

I wasn’t quite sure what to expect, so I put on my best tweed blazer and flared jeans (gah!) and dragged my then-boyfriend along to the party. I had prepared myself for an awkward experience, but when I saw Jane Kwett, a face I recognized from the site at the door I was put at ease. Entering the party and plied with a cocktail, I was thrilled to meet all the characters I’d be interacting with online in 3D. Everyone was welcoming, clever, and slightly nerdy, and I immediately felt like I wanted to be part of their tribe.

That night, I met the CEO Jeremy and much of the eight person team. For weeks after, I emailed any and all contacts at Yelp in hopes of getting a job. They were like, “Can you code? No? Sorry, we’ve got nothing for you.” But a few months after, they posted for an Office / HR Manager and I jumped on it.

What were your first impressions of Silicon Valley?

The early 2000s stereotypes were true: the scene I was privy to was mostly enginerds in hoodies who wore a rotating collection of startup t-shirts. When I started working at Yelp, we were sharing office space with a few other companies that were birthed from MRL Ventures, the incubator started by Max Levchin (Paypal co-founder). I didn’t know anyone else working at startups in the city. Most people I met in technology were at the old giants—eBay, Salesforce, Cisco—in the South Bay and a handful were at Google and a rising star called Facebook.

Walk me through your experience working in tech.

In 2004 at 22 years old, I started off as an admin at Yelp when the company was nine people. After a year or so, when the company set its sights on expansion, I joined the marketing department. We had a market-by-market strategy which involved a person on the ground leading the efforts. So off I went to Boston to launch our third city.

Essentially it was my job to introduce new people to the product and made sure they continued to participate. Tactically, this combined a heady mix of online engagement, offline events, local PR, content, and partnerships. Internally we were referred to as the “Mayors” of the city as we were always out and about. After Boston was up and running I found and trained a successor and moved onto the next market. After tackling a few cities, four years of a 24/7 lifestyle, and experiencing the company explode to over a thousand employees, I was in desperate need of a break. It was whiplash inducing, but awesome.

During a cross-country road trip with my now husband then boyfriend, I read about a site called Airbnb where you could stay at people’s homes instead of a hotel. I loved the concept. When I returned to SF and read that they were part of YC Combinator I figured they might be a company worth working for and figuratively banged down their door until I got an interview. This was 2010.

I was slightly disappointed to hear they’d recently moved out of the cofounders home as I looked forward to an intimate team again. But working at a place without a shower probably meant better hours. The position they were hiring for was content and as a weekly newsletter was part of our Yelp responsibility, I figured it was something I could tackle. I was also stoked about the introverted nature of the job as I felt socially tapped out. Fourteen interviews later I was offered the position – at a salary I’d been making years prior. Yelp had not yet gone public, so in hindsight this was probably not the wisest decision. But I negotiated a larger equity stake and began clicking away.

At 28, I was one of the oldest people at the company. What the team lacked in experience, they made up for in passion, creativity, and scrappy. Everyone was running a million miles an hour—sometimes in different directions—but there was certainly no lack of motivation. It was intoxicating.

What was it like building communities from the ground up? Did you have free reign to just build and learn as you went?

Marketing starts out a series of experiments of different channels—test and measure, tweak and repeat. As the bulk of my experience has been at early stage startups, there’s little dev and data time to devote to our cause. So initially you’ve gotta run on your assumptions. Nowadays, there’s a plethora of bolt-on products that can track anything under the sun. We weren’t so lucky in my day.

Fortunately at Yelp, Nish at developed a tried-and-true strategy that we were able to adjust to our local markets, so there was little on the strategy level for us to hash out. We had very clear output metrics and were rewarded with recognition accordingly. So I knew what I needed to do to excel.

Airbnb was green field. From the marketing side, they’d dabbled in the basic channels—social, content via blog, and video—as reflected by the team’s talents. But everything was a bit haphazard and as the founders had never managed marketing, we were left mostly to our own devices. Shortly after I joined they brought in a consultant named Julie Supan, formerly VP of Marketing from YouTube, who’d been recommended by investors.

Julie gave us much needed structure and our first tangible goal—to articulate the vision and mission of the company. As the content lead, I spent countless hours with her and cofounders in hopes of distilling the company’s raison d’être, and working in tandem with product, produced the Home and About pages seen by hundreds of millions of people around the globe.

After a few months, Brian and Joe got pumped about doing more community-oriented efforts and switched me to the task. They were excited about bringing people together offline with the hopes of activating host growth in target markets. How to do this, and to some extent where to activate, was up to me. The traveling began.

“I never saw myself paving any path. I’ve always felt more like a pinball ricocheting.”

At first we mostly operated from hunches. I had few tools to work with, aside from pulling the emails of hosts in certain geographies. Everything was tracked manually: the number of attendees, behavior changes post-event, referrals they brought in. We tested different promotions aiming to get a broader, new audience. Though all we could see were the number of properties in each city and the hits to the blog. As they kept increasing at a faster rate, we assumed we were doing something correctly. We optimized the sequence of different types of events: launch parties, host training sessions, and in-home host celebrations, as markets matured.

It wasn’t until my second year in, after I had grown the team to dozens of Community Managers in key cities, that the data dudes had the bandwidth to definitively prove our hypotheses: yes, users who attended events became more successful hosts and repeat travelers with higher lifetime values. It was not for naught.

Where do you think you got the knack for paving your own path in your career?

It’s interesting you phrase it like that. I never saw myself paving any path. I’ve always felt more like a pinball ricocheting. My decisions have seemed like a series of decisions optimizing for local maximums, more like a moth smelling its way than an arrow flying straight and true. But I’ve been fortunate that my compass has always taken me to good places and that’s reinforcing.

I attribute this to two things: only work for companies with a product I’m crazy about and want to use—case in point, I’m typing this from an Airbnb and I haven’t worked at there in years. And comfort with extreme risk. I can’t tell you how many times people have tried to dissuade me for working where I have, “Let a stranger sleep in your bed? That’s nuts.” or “Do they have any money? You’re going to be out of a job in months.” And the number of raises I’ve forgone for equity?! What can I say? I’m a stubborn believer.

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

In the past, my sole criterion was all about the product – did I use it, did I love it? Nowadays, it’s not just about product but also about timing. So much changes when a company scales and matures: employee culture, potential impact, compensation, career development and potential, time commitment. In the past I’ve liked the early stages when there’s freedom to be unconventional and potential to lay a strong foundation for growth. But there’s tradeoffs too, lack of stability and work/life balance, lower pay due to low revenue and/or funding, to name a few. I’m finally starting to understand why people I respect have worked at ebay and other corporate giants haha.

Overall, what have been the most exciting things about your work? What about your work really activates you? What are you proudest of?

It has been immensely gratifying to help shape a nascent product into something that tens millions of people interact with regularly. The sheer scale of potential impact of technology is astounding and addicting. I get most excited when hearing the stories of how people have improved their livelihoods, relationships, and decisions using products I’ve worked on: Business owners on Yelp attracting passion clientele that lets them thrive; Hosts at Airbnb being able to send their kids to better school or using the extra income to pursue a new career. It doesn’t have to be in profound ways either. Little incremental increases still count for me.

Everything I’m most proud of has a name: they are the people who comprised my team at Airbnb and are the founders of my portfolio companies now. We are made better by the people who give us reign and feedback, and that goes in both directions. I’ve never been a leader by force; if I had a superpower I think it would be that I recognize drive in others and the (potential) skills they possess, and will fight for the resources to make them successful. I hope my people feel the same way.

What has your experience been like transitioning into investing?

After Yelp and Airbnb went well, people began coming to me for advice about marketing.  I joined a few companies as an advisor—namely Skillshare and Threadflip—and helped craft their growth strategies. It was a great way to see these companies from the inside, providing valuable diligence. I then joined 500 Startup’s mentor network, offering guidance to their portfolio companies. This gave me increased insight into new sectors and teams, as well as keep a pulse on industry trends.

When I didn’t have ample bandwidth to go around, I asked how else I might be of help and was told that investing in these companies would be the next best thing. While of course I understood that this involved a high level of risk, I allowed myself to start investing because I felt like I received more from the startup ecosystem than I deserved and I wanted to give back.

“I read various approaches to portfolio theory, and thought it would be wise to invest in things I knew best – female-friendly consumer tech products.”

A few deals into it, finding that I enjoyed myself and that I was inclined to do more, I thought it would be best to get more educated on the matter. I didn’t know many early operators who were investing at that point. So I signed up for an angel investor crash course with Pipeline Angels. Hungry for deeper info, I flew to New York for another seminar with 37 Angels. Confident around a basic term sheet and having expanded my deal flow to the east cost, things ramped up.

“VCs tend to invest in what they know—problems they can relate to.” Tell me your thoughts on this, and what you’ve observed during your time in the and whether this is true to you as an investor.

It’s much easier to assess the value of a product if it’s solving a problem you can understand. Otherwise, you’re relying on the opinions of other people to determine its merits. Also, if it’s a sector you’re familiar with there’s likely better deal flow from your network. You’ll see Institutional VCs often determine their investment theses based on the experience of the partners.

I read various approaches to portfolio theory, and thought it would be wise to invest in things I knew best – female-friendly consumer tech products. Initially I took the “fund founders not (necessarily) products” adage to heart and invested in a few niche products started by people I believed were smart and competent. But as my capital amounts increased I became more discerning about the track record of the founder and the potential market size. From an ethos standpoint, I would love to invest in clean tech and education, but as these are sectors I know little about there’s an increased risk and decrease in my value-add to founders. The key advantage for me to potentially work as an institutional would be to gain knowledge from partners of these sectors. It may still happen.

“I can’t tell you the number of times founders have told me that community ROI can’t be calculated. Ask any technical person what they think of marketers and they’ll likely say that they’re “creative” or “feeler” types with no methods or data to back up their initiatives. I think this has largely been perpetuated by startups hiring smart but inexperienced people to run marketing because early on they can’t afford seasoned talent. This pattern, in addition to data and dev time being protected fiercely, can make it difficult to track returns. But that’s easily solved by the right tools.”

In general, how has your experience been as a woman in tech?

I know everyone anticipates horror stories and I hate to disappoint, but I don’t feel like my path in tech was made significantly more difficult by being a woman. I think this was partially because I was in a field—marketing—that’s high percentage female. I can’t recall any instances when I felt like the target of sexism. However, there has been the conscious awareness that I mustn’t play into the stereotypes of “bad” female behavior i.e. emotional irrationality and outbursts which factors into my communication style and has influenced my feeling comfortable speaking out in opposition. As I’ve rose in the ranks I’ve also been keenly mindful as to not come off too strongly or alpha for fear of being seen as a bitch or unlikeable.

While I also pride myself on being somewhat stylish, I know my friendliness is often mistaken as flirtatiousness so in the past five years or so I’ve been more conservative in my apparel choices—nothing revealing or body conforming. But the reasons for doing so are not just to discourage male attention, but to remove all question of why I may be getting ahead other than my own merit. I’m sure most men never have to consider this. Truthfully, I suspect I’ve largely been shielded from some of the more overtly inappropriate behavior from men because I’ve been in a serious relationship for most of my career.

What have been your biggest struggles?

I can’t tell you the number of times founders have told me that community ROI can’t be calculated. Ask any technical person what they think of marketers and they’ll likely say that they’re “creative” or “feeler” types with no methods or data to back up their initiatives. I think this has largely been perpetuated by startups hiring smart but inexperienced people to run marketing because early on they can’t afford seasoned talent. This pattern, in addition to data and dev time being protected fiercely, can make it difficult to track returns. But that’s easily solved by the right tools.

Like many marketing and community folks, I’ve had to contend with this much of my career. It’s hard enough trying to grow and engage users without having to constantly prove why you should exist. Oh, I should note that these stereotypes have shifted a bit as performance marketers have rebranded themselves as “growth hackers”. If there are any brand / community folks out there, I’ll cut to the chase: you’ll never get a lower CPA from any channel other than paid, so don’t try; instead focus on increasing LTV.

Angel investing is tricky and largely a failing proposition. You’ve heard about the power law rules of the game, right? Where one of your bets can potentially make up for all the others that have flamed out. Well, that means you’re competing for the hot deals with all the other early stage investors. Now that everyone’s an angel, getting into the deal is the hard part. So your network is everything.

Problem is, people have to know you’re doing a certain thing in order to share that type of info with you. And when I’m learning the ropes, I always shy away from the spotlight. There’s an inherent conflict, which I’ve now mostly overcome. But I’m sure I missed out on a lot in the meantime.

Have you had mentors or people who’ve looked up to for inspiration along the way?

I am grateful at Yelp to have had a number of bosses all strong in their own dimensions: Geoff Donaker Yelp COO with his business acumen and analytical bent, Nish Nadaraja for his creativity and engaging pen, Michelle Broderick for her direct but encouraging management style and sharp wit. Much of the time when I was an operator, I was so heads down building that I did little in the way of networking or professional development. It’s a shame in hindsight as I had access to an amazing group of investors and advisors and I regret not taking advantage.

The story has played out differently with angel investing though. For many months I was afraid to tell anyone I had started, afraid of smarter people scrutinizing my picks and judging me accordingly. But after I’d grown more comfortable and started asking people in my network for their thoughts on deals I found that most were more than happy to candidly share. Kanyi Maqubela, Josh Felser, and Niko Bonatsos have all been encouraging and insightful and I am ever grateful.

I’m a huge fan of Cyan Banister. I respect that she struck out on her own as an angel, not waiting for an institutional to invest under, and absolutely kicked ass. So stoked to hear Founders Fund brought her on as partner—couldn’t be more well deserved. From afar, I’m a great admirer of Aileen Lee and have watched or read every panel, interview, or talk she’s ever done. She’s sharp, irreverent, and downright cool. And of course a great picker. It would be a dream to work with her one day.

What are your biggest motivators?

I want my brain to be stretched. I’d like to grow in so many ways: creatively, business-savvy, analytically – and I hope to be able to help people in some way during this process.

Where have you found support networks?

Connecting with people that have shared plights and joys has been illuminating and validating. David Spinks gets full credit for bringing together community people through his organization and event series CMX, and I’ve met so many wonderful people that way. I’ve also gleaned valuable info and support from women in 37 Angels. The group consists of investors of various ages and backgrounds, and I’ve enjoyed their difference in perspectives. The startup scene can be a myopic echo chamber.

What would you like to see change?

The “change the world” mantra of tech is a double edged sword. On one hand, it’s a boon to the industry, attracting people from all corners of the earth to try and create a company for the goodness of humanity, and to leave a meaningful legacy behind. On the other hand, it creates this immense pressure to dream bigger and solve bigger problems. I’ve seen people spiral into incredible existential crises because they don’t (yet) have an idea that will change the world on a massive scale and it makes them really unhappy. We need to allow ourselves to work on things that move us, however seemingly insignificant. Everything starts out small.

There also needs to be more people of color, women, those from developing countries, and people from various socio-economic backgrounds in VC, so that the types of problems that are being funded are speaking to the needs of a broader swath of the world.

“I’ve seen people spiral into incredible existential crises because they don’t (yet) have an idea that will change the world on a massive scale and it makes them really unhappy. We need to allow ourselves to work on things that move us, however seemingly insignificant. Everything starts out small.”

And not to open a whole can of worms, but we need to close the gender pay gap.

So what are you working on right now, either for work or for yourself?

As Kim Hunter from Women Catalysts so nicely summed up, I believe that life is not a ladder, it’s a jungle gym. We don’t have to take a straight path to the top. We can be many things at different times.

Earlier this year I started a tiny tiny microfund that invests in restaurants, something I’ve been doing occasionally over the last few years. Many will laugh as it’s often thought of as a losing proposition. But this isn’t about 100x returns for me; I’ve got reasonable IRR in mind. My motivation stems from conversations with restauranteurs and chefs; I realized they lacked a supportive ecosystem. In an affluent city such as San Francisco with such a food-obsessed populace, this didn’t seem right. I hope to create a stronger bridge between the tech and food communities.

I’ve spent years focused on my career, ignoring the other aspects of life. This phase is about reaching new professional frontiers, but also being intentional about my family life, health, spirituality, and creative side.

How do your friends and family feel about the work you’ve done?

My family doesn’t really have any idea what I’ve done. They just know I have a decent amount of Google search results. As for my friends, I hope they’ve deemed me having accomplished enough to warrant their respect and esteemed company—hah!

What do you think about the state of tech in 2016?

Big question here. I could talk about the funding environment tightening up, how there’s no stone unturned in consumer, yadda yadda yadda. But you’ve heard it all before, I’m sure. So I’ll give you my take: I’m encouraged to see resources pouring into healthcare, clean tech, and education. But the overwhelming feeling is one of immense possibility, mostly inspired by my husband (who’s a programmer). I’m eager to see what the future holds with AI and VR/AR. In the next decade, we’re going to see massive shifts in production and human behavior with these technologies in ways we can’t possibly predict. As cliche as it sounds, I actually do feel blessed to be alive at this time in history.

What advice would you give to folks from similar backgrounds who are in tech or hoping to get into it?

Learn a hard skill. Move to a tech hub. Hunt down companies who hope to make a dent in the world in a way you can get behind. Bang down their door. Work hard for them, for free if you have to. Develop a network of peers and mentors. Stay up on the industry happs. Help people and be kind. You’ll be amazed at what comes back in return.

“Help people and be kind. You’ll be amazed at what comes back in return.”