Photo by Clay Banks on Unsplash

What is TripTippa? — Our Story

I started TripTippa as a side project in 2017 after realizing that there are very few viable alternatives to researching and planning a vacation on your own.

What if I could pay someone to research and plan my trip for me? Even better, what if I could get diverse perspectives by getting recommendations from multiple people? And by the way, what if those people were actual locals or frequent travelers to the place I was traveling to?

To me, this seemed like a much better way to travel. Instead of spending hours of research on my own, I could outsource to the people best suited for the role: locals and frequent travelers who are passionate about the place I’m visiting. And just maybe, instead of relying on the most reviewed places on Yelp and TripAdvisor, and deciding between 4 and 4.5 star ratings, I could explore a city in a more organic way through personalized, human recommendations.

TripTippa took a long time for me to build since I spent countless hours learning about engineering and web-development on my own. When I realized that my ideas were quickly outpacing my technical skills, I started to work 1:1 with an engineer I hired through UpWork. That engineer, based in Ukraine, and another engineer, based in New York, were the only 2 engineers who have worked on the product besides myself. I was able to learn quite a bit from studying their code and seeing how they approached different features. Eventually I was able to contribute a lot more code to TripTippa by continuously trying to further my knowledge.

Many of the features of TripTippa came about as a result of a continuous improvement. For example, initially advisors would submit all their recommendations in a single text box, and there were separate fields to provide a ‘booking link’. I realized that it was really tough as a traveler to make sense of what was basically an essay. Therefore, I came up with the concept of individual recommendations — a title, a link, an image, a google maps link, and a short description that you can upvote or add to your calendar.

Another example was when I realized that some people like to decide what they want to do on a particular day based on how they feel that day, whereas some people like to have a structured itinerary ahead of time. So I added the option to have an advisor plan your itinerary (for people that like to have a plan ahead of time), and another option to receive a Tinder-like swipe style option for your recommendations on each day that you are traveling (for people that like to decide on the day of).

Originally, my go-to-market plan for TripTippa was to target 8 or so destinations, onboard advisors there, and then target customers in the U.S. to those destinations. The first customer of TripTippa was someone traveling from Marrakech, Morocco to Rio De Janeiro, Brazil in early 2020, and I had not been targeting Rio as a destination or Marrakech as a target market. I quickly on-boarded advisors in Rio, and got the customer their recommendations. However the situation made me realize the need to build in code and processes that can accommodate any traveler in the world that stumbles upon TripTippa and decides to give it a shot. Now, TripTippa can do just that, although there will surely be improvements along the way to improve this aspect of the product.

The most recent feature that I’m proud of is TripTippa Hangouts, which I built over the pandemic. The idea for this was to have a casual, intimate conversation with a local and ask any questions about your trip or otherwise. While I’m a fan of tours and AirBnB experiences, sometimes I just want to meet with a local and have a more nuanced conversation about the place I’m visiting. So I built a feature for local hosts to offer their availability for in-person meetings that take place in a public setting (that the host frequents) and center around the traveler’s curiosity. Travelers can select ahead of time what questions they want to ask, and hosts can specify what type of recordings are permitted (so podcasters, YouTubers, or anyone who likes to record their travel adventures don’t need to feel uncomfortable about asking). I decided to keep the pricing at a reasonable $20 per Hangout, with an additional $5 for each guest.

As travel picks up in 2021, I’m now focused on reaching more customers. As you prepare for your next trip and decide on your next destination, I would be honored for you to choose TripTippa. Pricing currently starts at $20, and with an additional $5 you can choose your advisors (if there are advisors at your destination currently). If you’re unsatisfied for any reason, or if we can’t fulfill your request in a reasonable time frame, you will receive a full refund.

Kenny Kandola

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