Again and Again
With Oliver Pugh, founder & CEO of yetipay.
Oliver Pugh's entrepreneurial spark first appeared when he was 10. But it didn’t come from nowhere—it was fuelled by a dream: going to Disney World. Together with his sister, they calculated how much money they needed and earned it by doing chores. This first entrepreneurial adventure was a success, as the two young kids finally made it to Disney World.
That drive to build businesses stayed with him. In school, Oliver ran a small, though not entirely legal, DVD business. His entrepreneurial instinct led him to start working instead of going to university. At 18, he took a job at a local pub in his hometown, Northampton. Pubs were familiar to him—not because he loved to drink, but because his grandparents had run pubs and restaurants in the city. He quickly became the owners’ personal assistant, getting a real taste of what it meant to run a business.
He loved it. At 20, he decided to dive back into business—this time in a more formal (and legal) way.
People often think about product-market fit only in relation to customers, but the customer is just one part of the market.
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In 2008, Oliver started a business, Mobile Bar Hire Company, renting out bars and furniture for events. From day one, he was making decent money and ran the business for six years. But despite its success, the job was stressful and demanding, with constant issues during events controlling his life. The never-ending problems and their impact on his personal life made him realize he didn’t want to continue in this line of work into his thirties. It was time for something new, so he moved to London. Many of his friends from Northampton had moved to London to grow their careers. This was where the talent was, and Oliver knew it was the right place to build a successful business.
There, he launched a subscription box company, EarlyBird Snacks. But things didn’t go as planned. “We managed to raise some money—the first time I’d ever raised investment for anything. It was a learning experience on the job. That venture lasted about three years, but we failed. I’d say I learned more in those three years of failure than in the six years of success before. By the end, I was in a pretty bad way—completely burned out. I had to move out of my flat, and I’d broken up with my girlfriend. Basically, all the classic entrepreneurial stereotypes happened during that journey,” Oliver explains.
After three exhausting years, Oliver bounced back and started mentoring startups for the Swiss government in the Balkans. He joined the Swiss Entrepreneurship Program, which sends entrepreneurs from Western Europe to countries like Macedonia, Serbia, and Bosnia. The program organises tours, mentoring sessions, and other support activities for entrepreneurs. Oliver initially planned to stay for three weeks—he ended up staying for about a year.
“I had just gone through a big failure, and my confidence was really low—I was in a pretty bad state. Then I went to the Balkans and suddenly realized that all the lessons I had learned were valuable to others. I could share my story in different ways and hopefully help people avoid making the same mistakes. People say entrepreneurs will make mistakes anyway, but it’s better if they know in advance which ones they’re likely to make.”
Over that year, Oliver rebuilt himself. That’s when he came up with the idea for a pay-at-table device for the hospitality industry.
Here we go again.
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To start his new venture, yetipay, Oliver reached out to a software developer he had met during his tour in the Balkans. He convinced the developer’s agency to build an MVP for £5,000 and 5% of the company. They launched on March 6, 2018—a special day, as it was also his grandfather’s birthday.
The company had a solid start, and a year later, the startup raised funds from friends and angel investors. “We had big plans. It felt like an entrepreneurial renaissance after the failure of my previous company—getting back on my feet and finally reaching a point where I had some cash in the bank. And then the whole economy shut down.”
Fortunately, the company had low costs—around £10K per month—and enough runway to keep going. Thinking about what payments could look like over the next 10 years, the team decided to pivot. While players like Sunday were raising large sums to build QR code payments, yetipay chose to focus on hardware for Tap to Tip. With this idea, the startup raised another £300K, led by one of Saudi Arabia’s biggest angel investors.
“We figured out how to split tips from a card transaction on a traditional payment terminal. We launched this feature at BrewDog in Dublin, and in their first month, they collected around €5,000 in tips. Other BrewDog sites in the UK heard about it and wanted the same feature. We secured three sites in London, and eventually, we won the BrewDog contract for the entire UK—around 60 to 70 locations. That deal changed the trajectory of the company.”
Oliver had finally found a product that brought real value to customers, and this contract was the proof. But when yetipay tried to scale, a new challenge emerged.
The team ran into major issues with point-of-sale (POS) companies, which refused to provide the necessary integrations. The company was growing, but without a clear path forward. They had reached £300K in ARR, but scaling was impossible. Oliver realized that he couldn’t achieve product-market fit by relying on POS partnerships—an important lesson about the nuances of product-market fit. “People often think about product-market fit only in relation to customers, but the customer is just one part of the market. For a product to succeed, all aspects of the market need to align—suppliers, investors, and third-party integrations included. If your product depends on third-party integrations, you need product-market fit with those integrators too; otherwise, you won’t be able to scale effectively.”
Shortly after this setback, a friend introduced Oliver to an entrepreneur launching a POS platform in the US. During their conversation, Oliver discovered they could use Adyen’s platform to handle their payment volumes. That was a turning point. The team decided to shift focus—not just offering hospitality payments but building an open, flexible payment solution that anyone could use. To build the platform, they needed more engineers, but the company had limited runway. Oliver spent weeks meeting with investors, trying to convince them this was the right move. Some investors declined to reinvest, but a few loyal supporters backed the company.
It turned out to be the right decision. Over the next 12 months, yetipay’s ARR grew from £400K to £3.5 million, onboarding 50–60 customers per week. The company now processes £300 million in payments annually and has its sights set on Europe.
If this isn’t resilience, I don’t know what it is.
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