Headout is the new mobile app for getting fun travel destinations at cheap prices, ASAP. It has had over one million customers and is currently live in eighteen cities. It’s available on iOS and Android, and the purpose of the app is to help its customers rediscover the fun of travel without stress. The experiences Headout offers can also be viewed on its website, headout.com.

Headout combines the Uber-like convenience of finding a destination that is available in the next 24 hours with cheaply discounted prices in eighteen cities. Research has shown that 60% of travelers look for local experiences in their area the day of or before, so Headout is taking advantage of this market. Currently, Headout is most popular with tech-savvy city dwellers in the 22 to 35 years old age group, but it strives to be accessible to everyone.

History of Headout

Headout was first launched as Tourlandish in 2013 by a group of entrepreneurs from Bangalore, India – Varun Khona, who is now the CEO of Headout, Vikramjit Singh, who is now the CTO, and Suren Sultania, who is now the COO. The founding team had spent some time living in the US and had seen the opportunity for a B2C travel app. They had also had an annoying experience trying to coordinate a trip to Europe, and had needed to do research during the trip about where to go instead of actually enjoying their experience.

In late 2014, Tourlandish was relaunched as Headout in New York City. In early 2016, it had grown from a team of five to a team of thirty. And by April 2015, it had raised $1.8 million in funding during its seed round, thanks to US Version One Ventures, Nexus Venture Partners and Arena Ventures, and representatives and employees from companies such as Angellist, Funders Club, WhatsApp, Facebook, OLX Haystack Fund, Ludlow Ventures and Dreamit Ventures. Travelers from over 65 countries have used Headout, which has grown an average of 65% each month since its launch.

Since getting its $1.8 million in funding, Headout has expanded to 16 more cities beyond its original two of New York and Las Vegas. It is now live in San Francisco, Singapore, Budapest, Paris, Barcelona, Venice, Florence, Rome, Amsterdam, London, Abu Dhabi, Dubai, Hong Kong, Reykjavik, Edinburgh, and Madrid. In addition to helping people who are traveling to the United States, Headout is now able to help people traveling from the United States to other countries. Headout offers 24/7 support from local experts in the featured city who can give confused travelers help with where to go.

Some of Headout’s experiences even offer cash back, such as the Burj Khalifa, visits to the Eiffel Tower, and to the Dubai Aquarium and Underwater Zoo. It offers many different experiences in the cities it is live in, such as attractions, city tours, cruises, dates, theme parks, nature & wildlife, museums, churches, and visits to the baths in the various locations. Headout has top picks for each city; for example, the top picks for Venice include the gondola ride on the Grand Canal, a guided tour of the Grand Canal and a guided tour of St. Mark’s Basilica. Headout also has a blog featuring guides to particular cities and types of experiences within those cities.


Launching Headout in a new city, and maintaining it in current ones, both require significant effort on the part of its team. Market research is required, along with talking to members of tourism boards to find the best attractions for visitors to the city. Prior to launching in a new city, members of Headout’s team conduct surveys and interact with both vendors and natives of the city. They must be able to adapt to challenges – they found prior to launching in Dubai that a lot of the vendors found technology to be a challenge, so they simplified their job, letting them use SMS, emails and phone calls for bookings instead of just the app.

Khona considers hiring and communication to be the biggest challenges as a company. In order to overcome the communication challenge Headout has a meeting on every Monday with members from all cities and uses Slack. So far, they’re doing great!