Best Job Ever: Jen O’Neal, Founder of Tripping.com

Jen O’Neal, founder of global travel community site Tripping, first recognized the need for a site where adventure-seekers could connect and plan trips off the beaten path after several eye-opening trips abroad in 2009. Her go-getter ‘tude propelled her mission to create Tripping, which now boasts members from more than 175 countries, plus connections to 750,000 local homes in 15,000 cities.

On Tripping, users can find folks to connect with for conversation, language exchanges, free homestays, or even rent luxury villas via Tripping’s home rental service. Yup, owning your own travel site definitely qualifies for a Best Job Ever! Here, Jen gives us the deets on why.

How and why did you start your company?
A few years ago, I was offered a chance to work in Costa Rica, New Zealand, and the UK. While living abroad, I noticed how homogenized the world had become — you can eat at McDonald’s in the middle of Mumbai, stop at Starbucks on your way to a South American coffee plantation, and buy Eiffel Tower souvenirs that were made in China. The scenery along the tourist path didn’t seem to change, no matter where I went.

I started craving authentic cultural experiences. I’d venture off into random neighborhoods in the hopes of meeting local people. The less I followed my guidebook, the more colorful my trips became. Before long, I started thinking about creating a platform where travelers could meet locals for coffee, conversation, and free homestays.

Have you always had an entrepreneurial spirit?
My parents are both entrepreneurs, so I grew up thinking that everyone started companies when they became adults. I was shocked the first time I realized that I might have to work for someone else. It seemed like a crazy concept!

Have your educational and career backgrounds played a large part in what you do?
I graduated from Berkeley with degrees in English and Italian Studies, but the most pivotal moment in my college career came when I picked up our campus newspaper and spotted an ad for a tiny startup called StubHub. I was StubHub’s fifth employee and I went on to build the company’s brand and marketing group. I fell in love with business, and I stayed until the eBay acquisition six years later. I also studied in Italy during my junior year, which led me to move abroad after StubHub. That’s what ultimately led me to start Tripping.


Does the dress Jen’s wearing look familiar? It should! It’s one of our classics, the Coach Tour Dress in Azur.

What’s the company culture like at Tripping? Are all the employees super travel-savvy?
Our team is awesome. Everyone has either studied abroad, lived abroad, or worked in travel, so we’re a pretty international group. While everyone works hard, our culture is fairly relaxed — we typically start around 10 a.m. and work ’til late (or, until we decide to go out for drinks). We’re also pretty outdoorsy and we take advantage of being based in Northern California by going on team retreats to Yosemite and Big Sur.

Any travel horror stories?
I’ve been stranded in Germany, frisked by Colombian military off the coast of Cartagena, detained by UK immigration, caught in torrential rains while camping in New Zealand, and blackmailed by overambitious policemen in Costa Rica. Gotta love adventures while traveling!

Any favorite moments abroad?
Night swimming in an ocean lit up by phosphorescence, hosting 150 travelers in my tiny Notting Hill flat, or stumbling into a secret garden in the middle of Rome… just to name a few.

Thanks for the interview, Jen!

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Laura Vrcek

About Laura

With a passion for events, interviews, and her pet aloe plants, Laura strives to live in a world where writing poetry evokes celebrity status. When she's not planning her apartment's next face-lift, she's either befriending strangers or admiring maps. She has an MFA in Creative Writing, is a member of ModCloth's Charitable Giving Committee, and is an avid appreciator of funky hairstyles and too-hot sauces.

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5 Responses to Best Job Ever: Jen O’Neal, Founder of Tripping.com

  1. atomsofmyexistence 06/08/2012 at 11:44 am #

    Reblogged this on Atoms of My Existence.

  2. Jen O'Neal 06/09/2012 at 3:49 pm #

    Thanks ModCloth! Your team is fantastic and I had so much fun doing this interview.

  3. Sarah 06/10/2012 at 11:19 am #

    This sounds like the coolest job ever! Wow I can’t even imagine all the stories she must have to tell!

    ♥Sarah♥
    theantiquepearl.blogspot.com

  4. aparna 06/14/2012 at 11:23 am #

    can anyone suggest to me a blog that shares travel information on the “younger, hipster” part of different cities around the country? like williamsburg in nyc or mission dt in sf? i usually like to go thrifting, etc while on vacation… and i enjoy that kind of neighbourhoods..

  5. mw 06/23/2012 at 6:03 pm #

    If I could ask ONE question to Jen, it’d be what was your first step…your primary starting point…the absolute beginning of starting your own business/website?! Did you research? fund? look for help/others? Where did you start? I’m extremely interested in starting a business of my own as well and have asked this question to numerous people I come into contact with.

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