Connect with us


Cassie Shih Fuses Tech and Group Travel With Tripsha’s Creation



Group travel may have seemed like a thing of the past in 2020 with the pandemic seizing any ability to hug one another–much less travel as a cohort of strangers to a new destination. But with the pandemic’s end finally in sight, these human-centered activities are once again. And Cassie Shih, native New Zelander who is now based in New York City, is determined to bring back this element to travel. And she’s doing that with creation of Tripsha.
Tripsha creates a way for travelers to work directly with local and passionate hosts, and be in a group setting that propels the trip. “At Tripsha we want to take these trips and make them discoverable to a wider audience while helping the organizer with the nitty-gritty work that goes into running a great group trip,” explained Shih, the company’s founder.
Disrupt Magazine’s Olivia Liveng speaks with Cassie Shih about how she has disrupted the industry to create a marketplace that does more than provide the itinerary of a trip

OL: Tell us about your background and how you got into this idea of merging tech and travel. 

CS: I remember one moment in 2018, I was traveling in Costa Rica on my way to Monteverde when they unexpectedly shut the road. Road workers just started putting cones out and we knew we would be there for hours. I ended up speaking to the travelers from the car behind us and we got along so well we ended up merging our itineraries just to hang out more. Near the end of the trip, we stayed at their friend’s private beach house that came complete with its own amazing pool and staff. It just turned into the most incredibly fun, impromptu group trip and I wanted to know if there was a way to do this on purpose – and by ‘this’ I mean find people you like and share trips with them.

OL:  What kind of product is Tripsha? Who is your target reach and what is your final goal?

CS: Tripsha is an online marketplace for group trips. Similar to Airbnb or Etsy, we provide a site where individuals can post trips they’re organizing that other people can then discover and ask to book. What makes it exciting is that the best group trips today are being curated by individuals, not big travel companies. These hosted group trips are often hard to find though since to hear about them you have to already be reading the email newsletter, Instagram, WhatsApp group, or Slack channel where it’s posted.

OL: How do you believe Tripsha will disrupt the way both travelers and travel hosts can interact and travel? 

CS: I think group trips being sold only on the itinerary are going to die out. There’s just not enough information being given to the traveler that they can feel confident in what they’re buying. At Tripsha, we’re going in the other direction by creating a platform where everyone can find a trip that feels designed just for them. We don’t just tell you who a trip’s aimed at – we encourage you to chat with the trip host before booking. That’s powerful because it creates trust, especially if the host belongs to the traveler’s community or shares niche interests with them. I’m very excited by the diversity of travelers and trips Tripsha will be able to serve as we grow.

OL: Can you tell us a little bit about your day-to-day work as the CEO of Tripsha? What does that look like? 

CS: A big part of being CEO at a small startup is to check in regularly with the team and make sure they have what they need. I try to give clear priorities, provide resources and advice where I can, and then get out of the way. We work 100% remote so my mornings are typically structured around recurring calls and emails with team members, whereas afternoons are reserved for external-facing work like partnerships and marketing.

OL: Where do you see Tripsha in 1 year? 5 years? 10 years?

CS: The thing I’m most interested to see at the one-year mark is what communities we have traveling on Tripsha. Making sure we’re really serving them and learning from them and being useful. In five years I want Tripsha to be the go-to site for discovering unique group trips to book, as well as the go-to site for trip hosts looking to expand their business or start a side hustle. By the ten-year mark, I think Tripsha will have grown beyond what we now think of as leisure travel because of the changing nature of work and vacation. The two are increasingly blurring into one way we live our life and Tripsha is part of the largely digital toolset accelerating that process.

Olivia Liveng is a contributor at Disrupt Magazine and an award-winning travel, entrepreneurship, and lifestyle journalist and editor who relocated to Copenhagen from NYC. She has been featured in The New York Post, Fodors, L.A. Style Magazine, and Forbes.

Become A Crypto Expert


Recent Stories


Copyright © 2022 Disrupt ™ Magazine is a Minority Owned Privately Held Company - Disrupt ™ was founder by Puerto Rican serial entrepreneur and philanthropist Tony Delgado who is on a mission to transform Latin America using the power of education and entrepreneurship.

Disrupt ™ Magazine
151 Calle San Francisco
Suite 200
San Juan, Puerto Rico, 00901

Opinions expressed by Disrupt Contributors are their own. Disrupt Magazine invites voices from many diverse walks of life to share their perspectives on our contributor platform. We are big believers in freedom of speech and while we do enforce our community guidelines, we do not actively censor stories on our platform because we want to give our contributors the freedom to express their opinions. Articles are not commissioned by our editorial team, and opinions expressed by our community contributors do not reflect the opinions of Disrupt or its employees.
We are committed to fighting the spread of misinformation online so if you feel an article on our platform goes against our community guidelines or contains false information, we do encourage you to report it. We need your help to fight the spread of misinformation. For more information please visit our Contributor Guidelines available here.

Disrupt ™ is the voice of latino entrepreneurs around the world. We are part of a movement to increase diversity in the technology industry and we are focused on using entrepreneurship to grow new economies in underserved communities both here in Puerto Rico and throughout Latin America. We enable millennials to become what they want to become in life by learning new skills and leveraging the power of the digital economy. We are living proof that all you need to succeed in this new economy is a landing page and a dream. Disrupt tells the stories of the world top entrepreneurs, developers, creators, and digital marketers and help empower them to teach others the skills they used to grow their careers, chase their passions and create financial freedom for themselves, their families, and their lives, all while living out their true purpose. We recognize the fact that most young people are opting to skip college in exchange for entrepreneurship and real-life experience. Disrupt Magazine was designed to give the world a taste of that.