Happy Sunday!
Welcome back to Founders Feature, a weekly newsletter all about the journeys of young startup founders.
For this week's edition, I interviewed Cassie Shih, Founder of Tripsha, a group trip marketplace based in the US.
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Here’s what Tripsha is all about:
🏠 The Basics
The Problem:
Creating, selling, and managing a group trip is really hard work. Right now, individuals who organize trips and retreats do it all themselves - everything from marketing, tracking bookings, and monitoring travel restrictions to finding accommodation and soliciting feedback - almost always without the support of professional software.
The Solution:
Tripsha is a marketplace for community-led group trips. Our goal is to make it as easy as possible for individuals to create, sell, and manage group trips, as well as for travelers to discover and book these trips.
The Team:
We're a small fully remote team, although in the future we’re planning to hold global offsites to help everyone keep in sync. I'm the Founder and CEO, supported by a full-stack engineer, a head of trips, and a finance lead. We also work with a number of contractors in other roles like marketing and design.
🚀 The Journey
How did you come up with your startup/solution?
I've done a lot of travel in my life. I'm originally from New Zealand and when I moved to the US, I wanted to travel and explore more of the Americas. Since my friends weren't around to join me and I prefer to travel with others, my only choice was to book a group trip. I initially tried some big brand trips but found it was really hit or miss as to whether I would have anything in common with the other group members. What I really wanted was an easy way to discover and book unique trips with like-minded people. When I couldn't find a platform like this, it sparked my desire to build my own.
At first, my goal was simply to connect like-minded people so they could travel together. I brainstormed several different ways to do this but around the same time, I met Kerry, an independent group trip host and Tripsha’s current head of trips. Learning about the challenges individuals face when organizing group trips helped me focus on solving the problem from the host’s perspective. After all, the trip host is the person who sets the plan for the whole trip, clarifies intentions and expectations, curates the group, and is driven to give people a reason to choose the unique experience of traveling with them.
Why is this the right time for this problem to be solved?
There’s an incredible amount of energy being used for personal exploration post-covid. People are leaving their jobs, starting businesses based on their passions, and generally thinking long and hard about where they want to be and who they want to be around. This creates not pent-up demand for travel and a greater supply of individuals with the interest and capacity to organize group trips.
What is a recent success you are proud of?
Tripsha was recently featured in Forbes!
What is a recent challenge you have faced?
One of the biggest challenges of being a solo founder at the early stage is that it makes it difficult to ‘switch off’ since most major decisions will still run through you. Without proper management, it becomes a burnout risk, which is why I make a point to check in with my energy levels and get better at being more strategic with my time and attention.
What do you wish you knew before you started and is there anything you would have done differently in hindsight?
I wish I’d been plugged into the low code and no code communities right from the beginning. They are amazing tools and getting better all the time. Tripsha is built using custom code, and while a lot of the functionalities we have in our roadmap require us to be set up in a custom way, I could have learned some lessons faster and easier if I’d used a no code approach to validate ideas from the get-go.
🧠 The Lessons
What is the best advice you have been given recently?
When somebody points out something that's not working, they're usually right, but when they tell you how to fix it, they're usually wrong. I first received this advice in the context of a writing workshop but have found this extremely helpful as a startup founder receiving multiple lines of (sometimes conflicting) advice. Try to listen to the feedback and find the common problem. That is where you should be looking to fix. When it actually comes to finding the solution, remember that you know your business better than anyone else.
What advice would you give to other young founders?
When you're founding a startup, really consider whether what you're building and the path you're taking is really what you want or if it's just what's hot at the moment. There are many different ways to start companies, and you don't have to go the venture capital, tech startup route. Selecting the path for your business is one of the parts of starting a business that gets talked about the least when it's actually one of the most significant because it's going to matter all the way into the future.
Think about how you want to spend your days, not just what you want to achieve. For example, if you're someone who likes the nitty-gritty of building things, then becoming the CEO of a big company isn't going to satisfy you on a day-to-day basis. Really think about whether the path that you’re building fits with the future you want to live in.
What is the biggest lesson you have learned so far?
Everything good starts with an ask. To learn anything from someone else you just need to have the confidence to make the ask and know why you're asking. People who are too afraid to ask others are missing out. Never be afraid to ask questions.
✨ The Inspiration
Who inspires you?
People who work tirelessly to help others and live with integrity, and who often aren’t the most obviously successful. I really admire founders who are open about their lives, giving people a real insight into not just their successes but also their daily struggles.
What book do you think everyone should read?
I’ll go with my favourite television show Community!