“Got ten minutes? Go.”
This was the subject line of an email that Airbnb co-founder Joe Gebbia sent Jamie Wong several years ago. At the time, Wong hadn’t yet founded Vayable—she already had the idea for the online travel marketplace, but she was still reluctant to execute it. “I felt for some reason like I wasn’t ready,” she says.
When Wong, then an Airbnb host, encountered Gebbia at a meetup, she talked to him about how she really wanted to start her own company. “I asked him if we could grab a coffee, and we did,” Wong recalls. “Then afterwards he sent me an email showing me the first version of Airbnb. The subject of the email was: ‘Got 10 minutes? Go.’”
She was impressed (and shocked) by how Airbnb had since grown from its first version. “Now I know that’s all it takes—seriously. Ten minutes. Get it out. Joe was absolutely right. And I think this is what he tells entrepreneurs all the time, to this day, which is: Get it out.”
Getting It Out
Naturally, it took Wong more than ten minutes to create Vayable. She hustled. She put in the work. She found a technical co-founder (Tim Robertson), designed the site, and developed the technology needed to build her platform. But those ten minutes of “getting it out” were extremely crucial: it marked the end of Wong’s reluctance and the beginning of a commitment to turn ideas into action.
“When I moved back to San Francisco (where I grew up), I knew that I wanted to start this company,” Wong says. “But I felt for some reason like I wasn’t ready. I needed to save more money, I needed to gain more experience, I needed to build my network and get more experience in the travel domain. There was every excuse running through my head, every reason under the sun. The thing is, all of those things were actually true and very rational. But, I think that’s the whole point. When you start a company, it’s totally irrational. No one’s ever prepared, and doing it is a complete exercise in putting a cart before the horse.”
It turned out that Wong’s “irrationality” would spell major entrepreneurial success. Since its founding in 2010, Vayable has grown to offer over 2,500 handpicked experiences in more than 600 cities, connecting travelers to pre-screened local guides. The experiences can be anything from a Flushing Chinatown food tour in New York or or an insider-guided trip to a flea market in Paris, to an equestrian adventure in Buenos Aires or an urban art tour through the streets of Berlin.
Vayable has also been backed by Y Combinator. Recently, it received a seed round of funding from investors like SV Angel, 500 Startups, former Expedia president Erik Blachford, Scribd co-founder Jared Friedman, and Justin.tv and Exec co-founder Justin Kan. Thrillist has praised Vayable as a great way to “free yourself of tourist traps.” GeekSugar adds that the site is “definitely a more personalized way to see the world.”
Today, Wong is no longer reluctant about executing on her own vision, which is to make Vayable the way people travel. “I want to see us in every town, in every village, in every country around the world,” she says. “Hopefully, this will provide new infrastructure for tourism. We’re building a platform where people are making a living doing what they love.”
Connecting the dots
Vayable may be Wong’s first company, but she’s a born hustler. She holds a Master’s degree from Columbia University, where she was also awarded the Chancellor Scholarship for achievements in broadcast journalism. In 2006, she worked closely with the founders of Kickstarter on product development and community building, while also advising on business strategy at mobile payment company Boku; in 2007, she joined the team as a researcher/writer at Comedy Central’s The Daily Show with Jon Stewart, helping TDS win multiple Emmy Awards for Outstanding Variety, Music, or Comedy Series.
While growing up in California, Wong showed natural entrepreneurial instincts that she did not, at first, recognize she had. She’d pick lemons from the neighbor’s backyard and sell them back to the neighbors. Or she’d make drawings, lay them out on the street, and sell them as artwork. Or she’d perform her own musical shows and sell tickets to strangers. On hot days, she’d resell Otter Pops that her mother bought from Costco.
“My mom said, ‘Jamie, you’re selling them for less than I bought them for.’ And that’s when I learned about margin and profit.” Wong recalls with a laugh. “(But) pretty much every opportunity was an entrepreneurial opportunity. People say that entrepreneurs are born, and I think that’s true—but I also think that you may not realize you’re a born entrepreneur until much later in life. Once that happens, you look back at your life and suddenly the dots start to connect. They may not connect along the way. I thought I took all these detours but it turned out they were all necessary stops.”
Entrepreneurial Learnings and Experiences
Fast forward to 2013. Wong is at the inaugural Big Kansas City (a Silicon Prairie News event), talking to fellow entrepreneurs about “building the world you want to live in.” She says, “There’s no point going out and risking everything—the odds are stacked against you when you start a company—if you’re not actually building the world you want to live in.”
Later, in an exclusive interview with Technori, Wong shares even more words of wisdom, as well as her learnings and experiences from building Vayable.
On realizing she was an entrepreneur: “At TDS, I’d finally acquired my dream job and worked in this incredible environment and amazing culture with a very inspiring boss. I was spending all day mining blogs and news, reading about political hypocrisy, and making jokes about it. It was a freaking dream! But I wasn’t that happy. I wasn’t that engaged. I was executing on someone else’s vision. That was when I realized that if I have my dream job and I’m still dissatisfied with it, I need to start my own thing.”
On starting a company: “It’s like building a parachute on the way down. You don’t know. No one’s done this before. You need to remind yourself that while it’s great to get advice from mentors and read books and educate yourself about your market, all you can really do is follow your instincts. Because there’s no playbook. You’re writing your own playbook. If there’s already a direct way down then you’re probably not making a great contribution and you should probably pivot your idea. The art of the startup is building your parachute on the way down.”
On staying motivated: “You’ve got to love what you do. Because there will be days when everything is going against you and you have no control over it. Sometimes those days turn into weeks or months or, for some companies, years. You have to persevere. And I really do believe that the heart of perseverance is passion. It’s got to be more than just the end point or the goal that feeds you, because that’s illusory. What’s real right now is the journey. If you’re not enjoying that ride and don’t feel committed to it or believe in it, then you better get off.”
On authenticity: “I think that when you’re building a community marketplace, the community really responds to authenticity, to the fact that they can relate to you. We have a team and a foundation that’s really relatable because we are guides. Our community manager, June Lin, is one of the top guides on Vayable. I don’t know how she finds the time to do it but she does. But I do believe that everything has to start at home. All the values that we’re trying to impart to our community: it starts with us. We’re building a team where everyone’s making a living doing what they love.”
On the dynamics of mentorship: “Brian Chesky and Joe Gebbia of Airbnb have been incredible mentors. They have also become friends. I think it’s important that you’re friends with your mentors, that there’s mutual respect and that both sides are getting something out of it, the way a friendship really is. These relationships shouldn’t be just one-way. It should never be just about taking; it should be about finding ways to give back.”
On helping build a starter community: “Making entrepreneurship and technology more open is really, really important to me. My background is non-traditional for tech, being a woman, which is clearly a minority in tech, although of course for me the tech isn’t contained in just the gender issue. But (I love) the idea of being impassioned about opening up the sector to more people in general—and growing it. We need more talent. We need tech to be more accessible to more people. Anything that’s going to help build a gateway and a portal to that world, I want to be a part of helping build that. I feel like I’m not only very driven to do so; I feel like it’s my responsibility to do so.”