How I Started Trrip


Here’s a brief story of where the idea for Trrip got started:

I was living in NYC and I was planning my first solo trip around SE Asia for 6+ months. I had no foreseeable end date in mind. That meant quitting my job, leaving friends and family behind, and diving two feet in as an indie hacker. This was a philosophy that I strictly advised against while building my first startup Birrdi - a B2B golf tee time reservation system that integrates natively with Square POS (the first and only solution on the market to do so). I built Birrdi in my spare time (mornings, nights, and weekends) while maintaining a full time job as a Senior Software Engineer. This was the responsible route that I always advocated for.

Birrdi never gained enough traction to support my lifestyle full time. After 3 years I threw in the towel and started contemplating what to do next. Birrdi took such a toll on me mentally, and I invested so much time and effort into it, that if I were to start again from scratch I would have to do things differently. That’s when I contemplated the idea of going full time on a side project before knowing if product-market fit was achieved. Throwing myself into the fire could have unforeseen benefits, I thought. And plus, this wouldn’t be the first time. I experienced something similar when I attended University at 17 years old. I enrolled in Computer Science my sophomore year without any prior knowledge of the subject. As a mediocre and unmotivated student throughout high school, it was highly questionable whether I could come out the other end with a Computer Science degree. With enough grit and perseverance I did.

Back to Trrip. I’m someone who needs to have a detailed itinerary outlined beforehand to serve two purposes: to calm my travel anxiety and to become informed a priori.

I’ve never traveled solo before, and 6+ months was easily the longest trip I would ever take. In the past I used a mix of Google Docs, Quip, Trello, and Notes to build my trip itinerary. That’s when it clicked. I thought, why don’t I build an application that’s designed specifically for my trip itinerary needs. I could dog food the product, which I never had an opportunity to do with Birrdi because I didn’t own a golf course, and if all else fails there would always be 1 customer, me! It’s also B2C and not B2B, which I thought would be a refreshing change. That was enough reasoning to get started.

Around the same time I was looking into personal journaling apps for my trip, like the Day One app. I fell in love with the UI and the general experience. I loved how journal entries were broken down by individual days (this may seem obvious but I never used a personal journaling app before). Day One became the initial inspiration for Trrip’s UI. I thought, why don’t I replicate this UI, but instead of writing a journal each day you create an itinerary. The rest is history, really. I built Trrip within 1 month and I used it to create the itinerary for my SE Asia trip, which could be found here: About 2 weeks in and I had my first paying customer.

So, what makes Trrip so special you ask?

Well, similar to the Unix philosophy, I want Trrip to focus on one thing and do it extremely well: help you stay organized before, during and after your trip.

I’ve traveled a lot over the years, and I’m currently on a 6+ month trip throughout SE Asia. If you’re looking for a tool to help facilitate your trip itinerary, then check out Trrip - a site that makes a website out of your trip itinerary so you can stay organized before, during, and after your trip. And yes, I’m the maker of Trrip [I wouldn’t have built it if I couldn’t recommend it ;)]