James Hare knows how to start. The trick is starting again.

A desk is an economical place to begin an international travel company. It has two sides, which was useful for James Hare and Javier Pérez-Tenessa: in their early Silicon Valley office, they sat opposite one another. Years later, Pérez-Tenessa remembered the premises as little more than that table. The business would acquire customers, investors and considerably more furniture. At the beginning, the founders could at least find each other without booking a meeting room.

When eDreams moved to Barcelona, the accommodation initially remained modest. One early space near Bonanova came with a persuasive advantage: the founders could use it for free. There is a certain clarity to a rent negotiation in which the price is zero. The grander office, overlooking the water at the World Trade Center, belonged to a later chapter.

Hare has since moved on from the travel business he helped establish in 1999. He is now the Singapore-based co-founder and CEO of Us2.ai. Yet that shared desk is a useful place to meet him. His career concerns software, certainly, but also the practical business of assembling people, making an offer and keeping a company alive long enough to discover whether the offer works.

Before the boarding pass

Hare’s route into technology began with an education in the humanities. He graduated from Harvard in 1990; a later account of his early years describes his undergraduate studies as history and literature. Stanford followed, with an MBA completed in 1997. Between those two universities and around the early stages of his working life came a much wider geographical education.

He worked in Switzerland at the World Economic Forum, then helped establish an offshore software business in Ukraine. Back in the United States, his work included marketing at Ubisoft and Netscape, followed by business development at Electronics for Imaging. Games, browsers and digital printing supplied rather different products to put in front of a customer.

Those roles matter because Hare arrived at entrepreneurship with experience of getting software into markets. The technology changed between employers. The commercial questions kept returning: who wants this, how will they find it, and what needs to happen before they will pay? They are useful questions to carry across an ocean. They also survive a change of industry.

His public profile also lists English, French, Italian and Spanish, alongside elementary Chinese. The locations in his career include Geneva, the San Francisco Bay Area, Barcelona, Milan and Singapore. That gives the international business history a personal dimension. Different languages and places were already part of his working life before a travel company made crossing borders its business.

Customers get a vote

In 1999, Hare joined Pérez-Tenessa and Mauricio Prieto in founding eDreams. The company’s beginnings belong to the period when an internet business could attract both serious capital and extravagant expectations. Its first website launched in 2000. Spain and Italy were early markets. The founders had taken an idea formed in Silicon Valley and chosen to build a European business around it.

The original offer included holiday packages and a community of experts called Dreamguides. These people knew particular places or activities and could advise travellers. Prieto later described that part of the venture as something resembling a travel social network. It is a pleasingly human detail in a software story: behind the screen were people who knew where to go.

Then the company changed direction. In 2000, the founders saw more opportunity in flights and shifted their attention there. That decision gives the early story some texture. The business that reached the stock market was shaped through choices made after its creation. The first proposition had opened the door; it did not receive a lifetime appointment.

Growth also required time. Pérez-Tenessa recalled weak sales in the early years and a difficult period between 2001 and 2003. The internet bubble had burst, and travel faced its own troubles. He described the business gaining momentum after 2003 as its customer base reached a useful size. The familiar startup sequence of idea, investment and success leaves quite a lot out.

By then the company was developing its own technology and employing engineers, mathematicians and customer support staff. The work behind a simple search box could be extensive. A traveller wanted to compare a journey and buy it. The business had to make a shifting inventory of routes, seats and prices behave well enough for that ordinary request.

The ending with another beginning inside

The corporate milestones followed: investment from TA Associates in 2006 and Permira in 2010; a group formed around eDreams, GO Voyages and Opodo in 2011; a stock-market listing in 2014. A sequence like that takes up very little space on a company timeline. For the people building the business, it represented years of work and several changes of ownership and scale.

Hare served as president of eDreams and later as an independent director of eDreams ODIGEO. On March 25, 2015, he resigned from the board. The announcement said he had seen the company through its IPO and remained a shareholder. It was a recognisable stopping point: a founder leaving the board of a business he had helped bring into existence sixteen years earlier.

The distinction between leaving an executive job, leaving a board and selling every share can disappear in a brisk founder biography. Here, the public announcement is precise. His directorship ended. His shareholding continued at that time. The chapter had closed in one respect while keeping a financial connection to the company’s future.

There was another consequence of those years. By 2018, Prieto was describing at least fifty startups founded by people who had worked at eDreams, many of them in Barcelona. Colleagues became founders; some relationships continued through investment or professional services. Hare was part of the founding team of a company that had become a place where other people learned to build companies.

That is a different measure of a business from its listing or booking totals. People leave with habits, contacts and some sense of what can be attempted. It also makes the founder’s departure feel less like the end of a single story. By that point, other beginnings were already scattered around it.

In between the corporate dates, there is a more mischievous Hare. In a personal essay published in December 2014, he wrote about attending a retreat without his computer, phone, books or writing materials. He had pictured something rather more leisurely, complete with white robes and what he called “meditation with mojitos”. The timetable had other ideas.

His account included early starts, a strict schedule and an attempt to make a wall calendar hurry along by staring at it. Barça, which he identified as his football team, still managed to intrude on his thoughts. The essay is funny because he lets his own expectations take the punishment. A person accustomed to making things happen had volunteered for a place with very little interest in his preferred pace.

By 2017, he was building again. Hare co-founded the Singapore company now known as Us2.ai with Carolyn Lam and Yoran Hummel. Lam is also his wife. His next company therefore began with both a new professional partnership and an existing personal one. The travel chapter supplied experience; the new team supplied knowledge and skills of its own.

The partnership habit

Ask Hare about starting a company and he comes back to resources. His advice includes working with people who have already done the things a founder needs to learn, or who know someone who has. He has described how Singapore’s A*STAR helped Us2.ai through expertise, introductions and credibility. A small team could use those relationships to get further than its size suggested.

He also stresses speed and financial planning. He puts reducing the risk of failure at the centre of the founder’s job. That puts a useful obligation beside the excitement of founding. Someone has to consider how quickly the business is spending money, what the next milestone requires and which outside help will shorten the journey.

“Your number one job is to reduce the risk of failure.”

James Hare · 2022

His appetite for moving quickly shows up in his description of product development, too. Discussing Us2.ai in an early interview, he explained that the team tested successive versions with users and adjusted frequently. That process gives customers a continuing role in what gets built. The company has to listen after the first sale as well as before it.

In August 2026, Us2.ai announced a partnership with Corbotics, including a distribution agreement covering the United States, European Union and United Kingdom. That is the present-day business chapter: another set of relationships intended to help the company reach further. It sits naturally beside Hare’s earlier comments about what a small team can accomplish with the right partners.

When asked about the hardest part of his work, Hare has spoken about maintaining his ambitions through the daily pressure to compromise. Asked about the best part, his answer was creating. Both answers fit a career in which a completed company story has repeatedly been followed by something still being made.

There is an appealing lack of ceremony in that. The former eDreams founder has the degrees, the listing and the boardroom history. His practical concerns still include people, customers, money and time. Perhaps the shared desk remains the right image after all: two sides, a business to discuss, and plenty left to do before anyone needs a larger room.