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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.

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