How Headout Is Making The Spontaneous Schedulable

Vacations are supposed to be fun and relaxing – the dozens of "think pieces" generated in early summer each year about the importance of taking breaks, the tragedy of the decline of the American summer vacation and the importance of travel and leisure to #selfcare are all very specific on this point. Human beings need to take time off and see new things, because it is important to rest the mind and recharge the battery. Time away from work, these pieces usually argue, is fundamental to doing good work, because it prevents burning out.

And while there is much to be said for that insight – and in the actual scientific research that has gone into proving the value of vacations – it mostly overlooks a fact that millions of vacationers face every summer.

Vacations can be extremely stressful.

And, in fact, they get proportionally more stressful as more people are included in the official trip roster, as a bigger group tends to mean a greater mix of activity preferences. Some people want to sleep late, watch movies and maybe wander to a beach, while others want to take tours, play mini-golf, see historical sites, go shopping and go boating – and generally, the person who takes on the unofficial role of "trip coordinator" usually spends a lot of time trying to manage activities to keep the vacation fun and rewarding for all involved.

It is little wonder that so many people come back from vacation noting that they need another vacation to recover from all the fun.

But a San Francisco startup called Headout is hoping to take some of the sting out of the travel planning process by making it a bit easier to be spontaneous while on vacation.

Headout is a marketplace that allows consumers to book outings while on vacation, or otherwise visiting a new place, on short (usually same-day) notice.

"We want to help you rediscover the joy of traveling by bringing the best tours, activities and attractions in your destination right to your mobile device," said CEO and Founder Varun Khona. "We say ditch the tour guide and the lousy brochure and Headout. We want customers to have the freedom to be spontaneous, because the best holiday memories always are."

Headout has captured some interest in its vision of making vacation fun a bit more spontaneously enjoyable, as it has now picked up $10 million in Series A funding led by returning investors Nexus Venture Partners and Version One Ventures. That money, according to Khona, will go toward scaling the firm into more cities with more offerings. Their most common offerings are sightseeing tours, museums tickets (particularly those promising special or enhanced access) and theater tickets.

What makes the Headout marketplace unique, however, is that not just any vendor can place themselves on it. The company vets the activities in advance to make sure they are suitably fun offerings. Once a vendor has passed muster, they are given access to their own standalone mobile app that allows them to control when their activities are made available to Headout users.

The strategies used to move their unsold inventory (reducing price remains a time-honored favorite) are up to the vendor. That is, they can use the service to quickly fill unsold inventory by listing the number of seats or tickets available and reducing prices, if they choose.

The app was inspired by a European trip that Khona took with Co-founder Suren Sultania. During the trip, they realized that the process of trying to use mobile to book activities while on the road was a rather lumpy, friction-filled process.

“We knew there are a lot of folks like us who do not pre-book their holiday activities, and an app meant to do just that in the easiest way possible sounded like an exciting idea to work on,” Khona told publications.

Headout was the solution they found for that problem.

And the growth plan for the solution is ambitious. Today, Headout is in 20 cities across North America, Europe and the Asia-Pacific regions. In the next 18 months, the goal is to grow to a full 100 cities. They are also tracking a larger and more international audience by expanding their language supports. Recently, that saw the addition of German and Spanish listings in select markets. By the end of 2018, they hope to have all of the site's inventory available in 12 different languages.

All in, the firm has raised about $12 million in funding, and claims to have grown eight-fold over the last year.

But as it seeks to expand its business and footprint, the firm will face competition from the myriad of companies, big and small, vying for a piece of the travel activity market pie.

But Khona remains confident, as his firm is specific in its focus on last-minute bookings best served by mobile, with unique, curated experiences designed to offer consumers comfort when they decide to give that last-minute booking a try.



New forms of alternative credit and point-of-sale (POS) lending options like ‘buy now, pay later’ (BNPL) leverage the growing influence of payments choice on customer loyalty. Nearly 60 percent of consumers say such digital options now influence where and how they shop—especially touchless payments and robust, well-crafted ecommerce checkouts—so, merchants have a clear mandate: understand what has changed and adjust accordingly. Join PYMNTS CEO Karen Webster together with PayPal’s Greg Lisiewski, BigCommerce’s Mark Rosales, and Adore Me’s Camille Kress as they spotlight key findings from the new PYMNTS-PayPal study, “How We Shop” and map out faster, better pathways to a stronger recovery.