The first cheque came after a game of blackjack. Michael Hughes was in Las Vegas, playing at an hour that sensible business advisers would probably have declined to put in the diary, when a friend of a friend’s husband agreed to invest. Hughes thought he was joking. The following morning, the cheque appeared. Other friends and family followed. A company had acquired the thing every promising conversation eventually needs: enough money to begin.
The business became LoopUp. But the casino story, pleasing though it is, gives luck rather too much credit. Hughes and his co-founder, Steve Flavell, had already decided they wanted to build something together. They had spent time thinking about their colleagues, their working culture and the years they would spend inside the business. At one point, their shortlist included caravan parks in Britain. Telephony won. The alternative version of this story has considerably fewer conference calls.
That choice reveals something useful about Hughes. The product could be debated; the people mattered from the start. His career would take him through customer-led reinvention, a funding collapse and a public listing, then into the painstaking business of helping other engineers get their first chance. An unexpected introduction could open a door. Keeping it open required a different set of skills.
The helicopter apprentice’s memo
Hughes grew up in Wales and studied aeronautical engineering at Imperial College London. His education had an unusually practical runway. Westland Helicopters sponsored him, and he spent a year moving through departments before university, returning for summer experience. He later did his master’s thesis work in Barcelona. Long before Silicon Valley, he was learning how an engineering organisation actually operated.
At Westland, that curiosity spilled beyond his assigned work. Seeing the company laying people off, he wrote a memo to the managing director suggesting it was overlooking the capabilities of its interns. Then he went into the office to make his case. The result was work on special projects for the deputy managing director. It was an early taste of business responsibility, obtained through the somewhat direct method of asking the person in charge.
He went into strategy consulting at Monitor, then attended Stanford Graduate School of Business from 1995 to 1997 with a Sainsbury Management Fellowship. He graduated as an Arjay Miller Scholar. Stanford also supplied the relationship that would outlast several changes in telecommunications: he met Flavell there. There was rugby, too. Hughes served as joint captain and coach of the business school team. His time in California involved more than spreadsheets.
After a return to Britain, Hughes moved back to California and joined Pagoo, an early internet-telephony company where he became a founding member and CEO. Its initial proposition belonged to the dial-up age: when an internet connection occupied the telephone line, incoming calls could be answered remotely and messages sent back to the computer. The service developed toward answering calls on the computer itself. Hughes helped with strategy, fundraising, recruitment and international expansion. The company eventually failed, leaving him with experience that a business-school case study could only approximate.
The lawyer with the BlackBerry
By 2003, Hughes and Flavell were starting again. Their company was called Ring2 Communications. Its first idea made a computer into something like an expansive speed dial: click a telephone number in an email and place a call, then bring other people into the conversation. They sold directly to small and medium-sized businesses. Customers liked the convenience. Unfortunately, liking a product does not guarantee that its economics will hold still.
Telephone companies began bundling minutes into their prices. Ring2’s additional service became a harder purchase to justify. Hughes later described the error with refreshing economy: “We screwed up our understanding of the market.” The founders returned to customers and asked what remained useful. One partner at a London law firm wanted the information about a conference call on a BlackBerry. Seeing the call mattered as much as starting it.
The company shifted toward conference calling in 2006. Hughes’s explanation of its appeal started with the small irritations people recognised: organising an invitation, getting everyone connected and working out who had joined. A link could trigger a callback. An alert could identify the first participant. A screen could replace the ritual of asking the room to introduce itself again. There is a modest form of product ambition in making a familiar task less tiresome.
For Hughes, the opportunity lay among ordinary callers who still relied on dial-in numbers and emailed slides. The company could guide them toward screen sharing without requiring them to become enthusiasts for meeting software. Product design began with their existing habits. That approach gave the business a direction after its original proposition weakened. It also gave Hughes a very specific answer to the question of what his engineering team should improve.
The vote that bought time
Growth did not make the company immune to the outside world. In 2008, an anticipated $8 million investment round fell apart as financial markets collapsed. Hughes recalled that nothing had been signed, although the transaction was close. The company had begun expanding its team and spending on marketing. Suddenly the expected money was gone. The board could provide about $1.9 million, with an unambiguous requirement: reach profitability.
The staff numbered in the low twenties. Hughes remembered a meeting at which the team faced a choice between job losses and a 20 per cent pay reduction. Everyone voted for the cut. He had gone into the conversation feeling that he had failed; he came out surprised by the team’s determination. The business reached profitability within seven or eight months, in his account. The people-first intention of the founding years had encountered a fairly severe examination.
“I personally was nervous about that experience.”
Michael Hughes, recalling the staff meeting after the funding round fell through
Later, the company experimented with how it sold. Rather than leaving lead generation, selling and customer adoption in separate groups, it combined those functions into small teams called pods. Their incentives were tied to the incremental revenue they generated together. Limited money also encouraged recruitment of graduates and investment in training. Hughes described the process with the practical interest of someone who had spent considerable time making it work.
In 2016, LoopUp listed on London’s AIM market. Revenue that year reached £12.8 million. It was a substantial milestone for a business that had begun thirteen years earlier and changed its product along the way. Hughes was still talking about efficiency, processes and the everyday experience of a call. The listing offered a new setting for the same operational questions.
A ticket for the next engineer
Alongside the company, Hughes began working on another kind of access problem. A fellowship had helped take him from engineering to Stanford and into a network that changed his career. In 2013, he founded the Silicon Valley Internship Programme, offering graduates paid, year-long work inside Bay Area technology companies. The premise was concrete: let young engineers experience startup life at the beginning of their careers, while their own possibilities were still taking shape.
The launch programme offered a $60,000 salary and matched participants with sponsoring startups. Its ambition extended beyond filling engineering vacancies. Hughes wanted graduates to return with experience, connections and a greater willingness to start businesses themselves. A placement could give them a working understanding of what happens between an idea and a company. It could also make the people doing that work seem rather more approachable.
In 2015, SVIP partnered with Girls in Tech to encourage more female graduates to apply. By early 2017, more than sixty graduates had participated successfully. Hughes’s MBE in that year’s New Year Honours recognised services to British graduates in Silicon Valley and San Francisco. The official recognition attached to his work on opportunity, a parallel enterprise that had begun a decade after LoopUp.
He also helped launch GBx in 2016, a network of British entrepreneurs, investors and senior technology executives in the Bay Area. He is now listed on its advisory board. His support for visiting entrepreneurs has included Imperial’s San Francisco startup showcase in 2023. These are practical ways of making introductions less dependent on an accidental seat at the right blackjack table. They put founders in the company of people who might understand what they are trying to build.
Give the team a reason
Hughes’s published advice about managing engineers is similarly concerned with the conditions around the work. Give teams measurable business goals. Explain how their contribution fits. Remove unnecessary administration and meetings. Make feedback clear. His concise instruction is: “Always praise publicly and criticize privately.” The emphasis is on responsibility and trust, with the manager expected to clear obstacles as well as assign work.
That view helps connect the different parts of his career. An industrial placement gave him work beyond the classroom. A fellowship gave him another environment to learn in. His own company invested in graduate training when experienced hires were difficult to afford. SVIP arranged paid exposure to technology companies. The recurring mechanism is practical experience, supported by people willing to let a newcomer contribute.
Another change of line
LoopUp has continued changing. The company returned to private ownership in 2024, with its attention on multinational cloud telephony. The board concluded that the next phase of funding would be better pursued privately. Hughes remains co-CEO, responsible for product development and platform operations worldwide from San Francisco; Flavell leads global commercial activities from London.
The current work helps companies consolidate Microsoft Teams telephony across countries, replacing a patchwork of regional arrangements with a managed service. In July 2026, LoopUp announced a partnership with Digicel to offer its Operator Connect platform across the Caribbean region. The business now deals with a different set of communications complications from the BlackBerry-era call. There are still customers who would like the machinery to demand less of their time.
The blackjack cheque remains a good opening anecdote. Hughes has spent the years since giving the story more substance: listening when a customer points elsewhere, reorganising when money runs short, and arranging opportunities for engineers who have yet to make their own introductions. A chance meeting helped him begin. He has devoted a considerable part of his career to making the next meeting easier to arrange.