Cassie Shihof Tripsha: “There’s a saying that first-time founders focus on product while second-time founders focus on distribution”

There’s a saying that first-time founders focus on product while second-time founders focus on distribution. While that’s a generalization, at the beginning a lot of energy did go towards figuring out how to do something as opposed to whether we should do it. If I could go back to square one, I’d spend most of […]

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There’s a saying that first-time founders focus on product while second-time founders focus on distribution. While that’s a generalization, at the beginning a lot of energy did go towards figuring out how to do something as opposed to whether we should do it. If I could go back to square one, I’d spend most of my time on-demand validation and watching how potential customers behave before writing any code.


As a part of our series about “5 Things I Wish Someone Told Me Before I Began Leading My Company”, I had the pleasure of interviewing Cassie Shih.

Cassie Shih is the Founder of Tripsha, a website for discovering unique group trips. Travelers can book spots on group trips organized by creative individuals from around the world or post their own trips. Originally from New Zealand, Cassie moved to the U.S. in 2017 and currently lives in Brooklyn NYC.


Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?

I think being the child of immigrants I’ve always been curious about exploring other cultures and countries. My first exposure to New York was coming as an intern to work at the United Nations in my early 20s. The city felt so dynamic and full of possibility that it made a very big impression on me. I knew that I wanted to come back one day to build a company that could reach a lot of people. Fast forward to today and here I am, an entrepreneur working on a global travel platform, so I feel I fulfilled that early promise to myself.

Can you tell us a story about the hard times that you faced when you first started your journey?

The hardest part was just not knowing where to start. If I go back and read the things I said and did a few years ago I’d probably shake my head at how clueless I sound. What I’ve learned though is that’s actually a pretty common trait among entrepreneurs. Being willing to dive in and figure it out as you go means there will be times when you are the person in the room with the least knowledge and the most questions — and that’s OK! I had a bunch of the typical startup hurdles — a co-founder that didn’t work out, investors that ghosted — but I made my way through.

Where did you get the drive to continue even though things were so hard?

I’m very lucky in that the people around me have been consistently supportive. It also helps that I’m friends with a lot of other startup founders who can relate to what a slog entrepreneurship can be. During covid, when travel was impossible, people started sharing their old trip photos and it reminded me how meaningful travel is for a lot of people. So even as travel was shutting down around us, it always felt to me like something that would come back stronger.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?]

I remember at the end of a pitch I spontaneously decided to demo our product. This was when it was at a very early stage, back when our team were the only ones using it. At that time we were still making sure the basic functions like posting a trip worked, so we had put up a bunch of test trips with names like “Dancing on the moon” with images pulled from our laptops. Hopefully, the person found it funny seeing photos of our pets and not actual trips. If I was to do a pre-launch demo again, I would stock the site with trips like the kind we actually have now on Tripsha.

If you could go back in time and talk to your younger self regarding life lessons, things you would like her to know what they would be and why?

I would probably just say learn to appreciate the moment and don’t put off doing things to look after yourself or your loved ones! Knowing the difference between ‘urgent’ and ‘important’ and putting that into practice can make all the difference.

What do you think makes your company stand out? Can you share a story?

Tripsha started as a way to connect like-minded travelers. I’d been noticing more and more that travel was infinitely better (or worse) based on the people you were with, yet group trips were still sold based on the itinerary with no mention of the people going. One time I was traveling in Costa Rica when I met my (now friend) Elyse during a road closure that unexpectedly trapped us and a bunch of other tourists on the side of a mountain. We ended up talking and having such a good time later that we changed our whole itinerary just so we could hang out more. Experiences like these informed the design decisions we made while building Tripsha, such as allowing travelers to chat with the trip host before booking and asking hosts to explicitly think about who their trip is designed for and the vibe they want to create.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Everyone is different, but for me, I used to be a roll-out-of-bed, drink coffee, respond-to-emails type of person, and on some days I still fall into that pattern. However, I’ve found that I am much more productive when I have a slower start, because even while I’m making breakfast or watering plants, my brain is thinking through my priorities for the day, so by the time I sit down to work I’m much more deliberate about where I’m investing my energy.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

There’s so many people it’s hard to pick just one. My husband Lane has always supported my endeavors, and earlier this year he struck out on his own as an independent attorney so now I have the privilege of supporting him as he builds his practice. My parents have also been very consistently supportive of my businesses, going all the way back to side hustles I had in high school selling items on New Zealand’s equivalent of Ebay. Tripsha’s earliest angel investor Mike also backed Tripsha and me before we even had a product which was a big boost of confidence. I don’t think it’s possible to know where I or Tripsha would be without this invisible roster of support.

How have you used your success to bring goodness to the world?

I hope most of that is still yet to come! I do make time to give back by helping people who are at the earliest stages of their startup journey. I recently began advising a telehealth startup that’s working to provide access to mental healthcare for the millions of children in the U.S. who lack access. If there’s anything venture dollars should get behind, it’s tackling big, bold issues like that. And helping travel to recover post-covid of course 😉

What are your “5 things I wish someone told me before I started my company” and why? Please share a story or example for each.

There’s a saying that first-time founders focus on products while second-time founders focus on distribution. While that’s a generalization, at the beginning a lot of energy did go towards figuring out how to do something as opposed to whether we should do it. If I could go back to square one, I’d spend most of my time on-demand validation and watching how potential customers behave before writing any code. I’ve also learned the big difference between being efficient (doing something using fewer resources like time and money) and being effective (achieving results). The former is just one possible pathway to the latter, which is ultimately much more important.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I wish people would spend more time interacting with others and learning about the world around them. The pandemic really brought home the mental health and economic costs of isolation. I see my work on Tripsha as part of a broader trend where people are figuring out how to earn a living online, but live their life offline.

How can our readers follow you on social media?

We’d love for more travelers to join our Facebook group https://www.facebook.com/groups/tripsha or follow us on Instagram @tripshatravel.

This was very inspiring. Thank you so much for joining us!

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