
Photo credit: Swaminathan
There are plenty of reasons not to launch a travel startup. Statistically, most travelers only take trips once or twice a year, and, when they do, they book hotels, plan flights, and sign up for packaged tours – all business models that have been beaten to death.
Because there’s a lot of free content online – think Wikitravel, Trip Advisor reviews, and Lonely Planet – monetizing travel information can be difficult and, really, what’s to say that a two-month old startup is trustworthy enough to support you on your grand trip through Peru? While most startups operate with the assumption that the travel industry is disconnected and broken, the amount of people that already flock to different countries each year shows that this might not be the case.
In fact, the popularity of travel seems to suggest that most travelers enjoy the ambiguity that comes with getting out of their comfort zones, going to a new country, and having to figure things out once they arrive.

Photo credit: Reinhard Link
Despite the many failures that travel startups have seen, however, entrepreneurs continue to enter the sector. “We did it because we wanted to keep in touch with traveling,” explains Ameya Sahasrabude, co-founder of personal assistant chat application Ithaka. While the app can be used to plan trips in advance, its differentiator begins once a traveler lands. The chat app allows users to ask questions about a variety of things, including foreign exchange stands, ATMs, and places with wifi.
Ameya and his classmate, Rahul Singh, have a typically inspirational startup story: Both graduates of the prestigious IIT-Bombay, they worked for a few years in corporate positions, quit their jobs, and, while traveling Southeast Asia, happened upon the idea. The name of the startup is based off of an illustration of Ithaka, a poem by Greek poet Constantine P. Cavafy. The poem explains a simple point: the richest treasures in life are not found at the end of the trip, but are instead uncovered bit by bit along the way.
For the independent traveler

Rahul Singh and Ameya Sahasrabudhe
In some ways, the non-intrusive chat app helps make the microcosm of the trip a little more pleasant. “People should be allowed to plan out their own trips,” explains Ameya. “When they need help, though, we’re there for them to reach out to.” Ithaka was originally launched as a Whatsapp number and, after the team gauged its popularity, it soon moved onto an Android application. They also have an iOS application.
There are, of course, as many types of travelers as there are people. While one end of the spectrum includes those with larger ticket sizes who book package tours in luxury villas, the other end is comprised of nomadic travelers whose ticket sizes are unpredictable and generally miniscule. Then, there’s the massive middle ground, whose desires shift based on their mood.
In order to figure out basic questions, Ithaka is building out a database on its app. “Every time someone asks a question, someone on our team answers it immediately,” Ameya says. “We’re also building out a database of questions that are asked the most.” The toughest part, of course, is turning the type of casual vocabulary we use while chatting into something that can be automated.

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