
The story of how a Memorial Day trip led me to leave my dream job at Square to build TripKai.
Picture this: Memorial Day weekend, 2024. My friends and I are planning our annual camping trip. We're all excited, but there's one small problem – we have no idea who's bringing what.
The group text is exploding with messages. Someone's asking about the grill. Someone else needs to know about sleeping bags. The Excel sheet we created to track everything? It's a mess. We only need one grill, but everyone needs a sleeping bag. What we committed to bringing got lost in the mix, and it was nearly impossible to figure everything out.
I remember thinking, "There's gotta be an app for this." So I looked. And looked. And looked some more.
There wasn't one.
At the time, I was working as an Android developer at Square – my dream company. But this problem kept nagging at me. I couldn't shake the feeling that event planning shouldn't be this hard.
So I started building TripKai in my spare time. Nights, weekends, any moment I could steal between my day job and life. I was wearing every hat – developer, designer, product manager, marketer. It was exhausting, but I was solving a real problem I had experienced firsthand.
After long discussions with my wife and friends, I found myself in a good position to make the leap. On March 5, 2025, I left Square – the company I had dreamed of working for – to pursue TripKai full-time.
It wasn't an easy decision. Square was everything I thought I wanted in a career. But I realized that building something that could help people like me – people who just want to plan events without the chaos – was worth the risk.
I went from being a solo developer wearing many hats to building a team. Today, TripKai includes me plus three amazing contractors:
• A software engineering intern working on the website
• A designer helping us create beautiful, intuitive experiences
• A business consultant guiding our strategy and growth
It's incredible to see how much we can accomplish when we're all focused on the same mission.
My goal is simple: make plans easy. I want to solve the exact problem I faced during that Memorial Day camping trip, and the countless other planning headaches we all experience.
TripKai helps you centralize your event details to avoid the headache of communicating across texts, calls, and emails. It helps you organize the planning process and get your friends engaged. And most importantly, it helps you enjoy your event by getting yourself out of the "ask-the-host" role and into the fun.
Use TripKai to centralize your event planning and get out of text threads. Organize to get your friends engaged and get help so you can enjoy your event.
Stop waiting — Start Planning.
TripKai
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