Female Founder Stories: Jamie Wong, Founder of Vayable (YC S12)

by Y Combinator2/8/2015

Vayable is the global marketplace for unique experiences.

Q: Tell us about your background prior to starting Vayable?
I traveled to more than 40 countries, wrote and produced stories for The Daily Show with Jon Stewart, Michael Moore, ABC News and PBS Frontline. I have a masters of science in journalism from Columbia University and a BA in History and Political Theory from Wesleyan University.

Q: What’s Vayable’s origin story?
I grew up speaking four languages by the time I was five years old. My father is an immigrant from Hong Kong and my mother’s family immigrated from Poland and Russia. This meant from a young age I always knew there were multiple ways of perceiving and communicating experiences and ideas and became fascinated with understanding how other people live.

When I was 8 years old, I spent a week living with a family on a Hopi Indian Native American reservation with my third grade class and it awakened me to even more different ways of living and viewing the world – it also left an imprint that would continue to define how I experienced places and people I met.

Years later I was in Morocco and met a man in a carpet shop who offered to drive me through the Atlas mountains and into the Sahara to go on a 5-day camel ride with his cousin, Ali, the chief of a caravan tribe. For a quarter of the price I would have spent on a packaged tour, I enjoyed an authentic experience into a new part of the world and someone’s life, while the tribe earned enough money from me to support themselves for a month.

I began a blog to document my experiences and would connect friends and strangers with the people on the ground who had facilitated these back-door adventures for me. Eventually the demand for these unique, custom experiences from within my own community grew and I saw the opportunity to turn my blog into a global platform where individuals in all corners of the world would be able to earn a living sharing unique experiences with other locals or travelers.

Q: Tell us about your experience at YC.
I entered YC thinking I had several inherent disadvantages: I was non-technical. I had never started a company before. I had never worked at a tech company. I studied “soft” sciences in university. I had already turned 30. I was a woman. I was right to believe this meant I was an outlier, but I was incorrect in thinking this would put me at a disadvantage at Y Combinator. Unlike many other parts of the technology, investment and entrepreneur communities that make up what we think of today as the figurative “Silicon Valley,” Y Combinator is not a culture of prejudice, it’s a culture of pragmatism.

There are three main ways I experienced this during my three months doing the program that I have assimilated into our company culture and my approach to building a product and business.

  1. Cadence: Weekly Tuesday night dinners with a high-profile speaker, Q&A, and sharing updates and challenges with batchmates over bowls of glop every. single. week. taught us the importance of creating cadence with both product and business cycles of the company. Having milestones, events and regular check-ins to orient our work around is critical to sustainable high output. It also gives a sense of structure and predictability – something startup founders hate in large quantities, but need when building a startup when your world feels like absolute chaos.

  2. Common sense: It turns out that most of the guiding principles of building a startup are guided by common sense. YC teaches this. This may seem anti-intuitive that a startup accelerator would teach and encourage something as basic and non-disruptive as common sense, but founders are a self-selecting community who seem to lack a lot of it.

  3. Community: Probably most important was the YC community – the batchmates I connected with during YC, as well as those I connected with after, as well as alumni, partners and all the staff. While I went into YC thinking these were not “my people” and they would not understand me (for reasons mentioned above), it turns out they are and the YC community has been one of the most important and valuable assets I’ve had in building my startup, and continues to be – perhaps even more so – as time goes on.

Q: What is the atmosphere like at YC with Demo Day approaching?
Tense, exciting and palpable. The nervous energy alone would be enough to power the large fan in the main room at YC. Everyone is working so hard, doing everything they can to breathe another day, month or year of life into their business. Even the most successful startups at this stage have no guarantees. It’s like being in a silent theme park where you don’t hear the whoosh of the roller coasters or the screams of the people, but you can feel the rush of the up and down. There’s a feeling that we’re all a part of something really big, because during those three months, we all are, even if only in our minds.

Q: Was being female either an advantage or disadvantage in working on your startup?
There are always two sides to every coin. I cannot separate my gender from who I am as a person or a founder. Practically speaking, there are clear, well-documented disadvantages we face, particularly when it comes to raising money. It’s a disadvantage to our community and society at-large that sexism is still so prevalent in tech and startups. We’re all suffering from this, not just female founders who experience it directly. Women are far more aware of the suffering because it’s personalized, but sexism in Silicon Valley holds the whole world back.

Q: What was the hardest part about being a female founder?
Dealing with rampant and unapologetic sexism from the community.

Q: Why do you think there are fewer startups with female founders than male ones?
Higher risk: There’s less of a safety net for female founders and therefore they face a higher risk than men do when starting their own companies (women have less savings, less earning potential, less funding, more expenses and more responsibilities).

Investor bias: Investors are biased toward industries and founders they understand. Most investors are men. “Pattern matching” is a term many investors abuse as a euphemism for institutionalized discrimination. Lack of role models: As humans, we model ourselves off of our parents and others who we identify to be like ourselves. With few women founders and CEOs, it doesn’t occur to as many women that we can pursue this. Pregnancy/life-planning: Statistically founders are most successful in their 30s and 40s, which is exactly when women are in their childbearing and raising years. Women – unlike men – face more of a binary choice around building a family or building a startup. If men had uteruses, there would undoubtedly be more female founders today. (Hey, that’s a startup idea!).

Q: What do you wish someone had told you when you were 15?
1. You should try programming, I think you would like it and would be great at it.

2. You should start a company, you have what it takes to be a great entrepreneur.


  • Y Combinator

    Y Combinator created a new model for funding early stage startups. Twice a year we invest a small amount of money ($150k) in a large number of startups (recently 200). The startups move to Silicon