Building Trust in the Unknown

Entrepreneur

27-05-2025

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That's something else. For David Midgley, founder of Squared.io, a London based SaaS company, the journey meant more than just scaling a SaaS tool - it meant educating a market, convincing enterprise clients to take a leap of faith, and learning to lean on a startup community he didn't realise he had. In this candid conversation with Entrepreneur UK, Midgley shares what it took to build credibility from scratch, and how customer feedback - and founder humility - can quietly shape a company's biggest breakthroughs.
When Midgley set out to build Squared.io, he wasn't just introducing a new product - he was introducing a new way of thinking. "One of the biggest challenges was creating a brand-new category of product," he says. "It's not easy getting people to understand and trust something they've never seen before! We had to spend a lot of time educating the market, building credibility, and showing the real value we could offer."
Rather than flood users with jargon or overpromise flashy features, Midgley and his team took a different route: relentless transparency. "We focused on clear, honest communication, listened closely to early feedback, and made sure every experience people had with us was a great one," he says. "Bit by bit, we earned trust and carved out our place in the market."
That patience also extended to the kind of customers Squared.io chose to pursue. While many early-stage founders chase quick wins in the SME space, Midgley took a calculated risk by prioritising enterprise clients. "In the early days, I made a conscious decision to focus on enterprise customers rather than small businesses," he recalls. "I knew it might take longer to close deals, but I also believed these larger companies would be more likely to stick with us and work in true partnership over the long term. Plus, they were feeling the problem we were solving much more acutely, which made them more motivated to find a solution."
It's a strategy that's paid off. Larger customers not only gave Squared.io stability in uncertain times—they became active collaborators. "Listen to your customers," Midgley says. "Some of our best features and biggest wins have come from customer suggestions that we might never have thought of ourselves. It's easy to get caught up in your own vision of what the product should be, but the people using it every day often see opportunities and needs you wouldn't spot on your own. Staying close to them has been a huge part of our success."
That openness to feedback extended beyond users. For Midgley, a turning point came when he started connecting with other founders. "I wish I'd known just how supportive the UK start-up community, especially other SaaS founders, can be," he says. "In the beginning, I often felt like I was figuring everything out on my own. But once I started reaching out, I realised so many other founders were happy to share advice, experiences, and even just encouragement. Knowing that earlier would have saved me a lot of second-guessing and made the journey feel a lot less lonely."
From convincing a skeptical market to betting big on enterprise, Midgley's journey with Squared.io is a case study in the power of strategic patience, customer empathy, and founder vulnerability. It's a reminder that even when building something no one fully understands yet, success often comes down to something simple: staying close to the people you're trying to help.