From Side Projects to a Digital Powerhouse: How Matteo Cordini Built PLAYGROUND on Trust, Grit, and a Bit of Chaos

In this edition of Bright Founders Talk, we sit down with Matteo Cordini, the Co-Founder of PLAYGROUND, a dynamic digital agency with roots stretching back to the early days of the web. Matteo’s journey into the digital space began in 1997, when he built his first commercial website as a teenager. A decade later, his passion and experience culminated in the founding of PLAYGROUND, alongside longtime friends with diverse and complementary skills. 

What started as a creative side project quickly evolved into a full-fledged agency supporting both SMEs and global brands. In our conversation, Matteo opens up about the unique bond he shares with his co-founders, the challenges of building a business from scratch, and the importance of trust in long-term partnerships.

He also shares how a simple favor for a friend in Berlin sparked the idea for PLAYGROUND. Today, the agency boasts a 60-strong team and delivers services across UX/UI, brand strategy, omnichannel campaigns, and more. Join us as Matteo reflects on two decades of digital evolution and the lessons learned along the way.

From Berlin Blogs to Digital Brilliance: How Matteo and His Best Friends Built PLAYGROUND

When Matteo Cordini talks about starting PLAYGROUND, it’s not the typical “garage startup” story. It all began with a favor for a friend in Berlin who wanted to start a fashion blog—remember when those were the next big thing? Matteo, a creative by nature, designed the logo “just for fun.” That one playful project became the unexpected spark. “She fell in love and said, ‘You have to make the website,’” Matteo recalls. Before he knew it, he and his lifelong friends were signing agency papers and sketching out their new future—completely unaware of what running a business actually meant.

The trio behind PLAYGROUND wasn’t stitched together through LinkedIn or networking events. Matteo, Gabriele, and Paolo had grown up side by side. “We know each other very, very, very well,” Matteo says with a grin. “Pros and cons.” Their bond wasn’t built in boardrooms but on playgrounds—quite literally. That deep-rooted trust became the foundation of their company. Sure, there were warnings—his dad advised against mixing business with friends—but Matteo trusted his gut. And it paid off: “Trust is the number one condition for me to work.”

Fast forward to today, and PLAYGROUND is a 60-person agency working with international brands. Matteo admits they were great at designing websites but clueless about company-building at the start. Still, their complementary strengths—strategic, technical, and creative—helped them balance things out. And Matteo hasn’t let go of his hands-on approach. He still sits in on final interviews, asking quirky, real-life questions to test how candidates think, react, and even joke. Because at PLAYGROUND, culture fit isn’t just a buzzword—it’s part of the DNA.

Culture by Design: How Matteo Built a Team That Says “No” (When It Matters)

As PLAYGROUND began to grow, Matteo noticed something was shifting. Moving from under 30 employees to over that threshold meant the cozy, open-space vibe started fading. The unspoken culture that once spread naturally just by sharing a room now needed intentional structure. So, in true creative spirit, they sat down and wrote it all out—with stories. “We created a document filled with examples of what’s okay and what’s not. Like, no yes-men—we even used the Bay of Pigs as a lesson in bad groupthink,” Matteo laughed. It was their way of making values memorable and human, not just another corporate PDF buried in someone’s inbox.

Then came COVID. For some, it was a crash. For PLAYGROUND? A surge. With 80% of their clients in retail, and physical stores shuttered overnight, digital became the lifeline. “It was hard to stay ahead of all the requests,” Matteo said, “but it gave us a serious boost.” The team had to adapt fast, balancing innovation with high demand—and doing it remotely. That shift also brought a deeper reflection on generational work styles and what accountability looks like when you’re mostly on Zoom.

Technology-wise, Matteo stays grounded. Even when clients come in starry-eyed with big dreams—like that one campaign that looked good on paper but made zero business sense—he always levels with them. “Our approach is to be honest,” he says. AI is no exception. While PLAYGROUND uses GenAI regularly, Matteo draws the line at shiny hype. “Using GenAI for fashion brands? Not really there yet—unless it’s light, playful stuff on socials. Otherwise, it’s more headache than help.” In a world where buzzwords rule, Matteo’s superpower is simple: cut through the noise, keep it real.

How Saying “No” Helped Matteo Build a Business That Keeps Growing

In a city like Milan, with what Matteo jokingly calls “10,000 competitors,” standing out in the digital agency scene isn’t easy. But PLAYGROUND didn’t need flashy campaigns or aggressive sales tactics to grow—they had word of mouth. Their breakthrough came with an iconic retail brand, FE. “We worked below cost just to deliver something outstanding,” Matteo shared. That one project? It sparked a ripple effect of referrals that still fuels their growth today. Because for PLAYGROUND, trust isn’t a buzzword—it’s a business strategy.

What really makes them different, though, is their willingness to challenge clients, not just please them. Matteo puts it simply: “Sometimes saying no is the best way to earn trust.” That mindset has helped PLAYGROUND navigate a sea of shifting trends and relentless client expectations. Their team focuses on value, not just execution. And that means being brutally honest—even if it means turning down work that doesn’t serve the client’s real goals. It’s not the easiest approach, but it’s definitely the most sustainable.

To stay ahead, Matteo’s team doesn’t just watch the trends—they experiment with them. From early investments in gamification to building full platforms for remote teams during COVID, PLAYGROUND treats R&D as essential, not optional. “It’s a mix of keeping our eyes open, listening to clients, and dedicating people to explore what’s next,” Matteo says. Whether it’s AI, digital events, or interactive experiences, they test new ideas before offering them to clients. That curiosity, paired with their grounded honesty, is what keeps PLAYGROUND both innovative and trusted—two things that don’t always go hand-in-hand in a fast-changing industry.

From Failed Apps to Stoic Startups: Matteo’s Take on the Future (and What Really Matters)

Matteo isn’t the type to get dazzled by shiny tech without asking the hard questions. When talking about the future, his mind goes beyond websites and trends—it’s about experience. “Will we even have websites in ten years? Probably not,” he muses. Right now, he’s more curious about voice interfaces, predictive navigation, and reimagining digital spaces altogether. At PLAYGROUND, they’re already testing AI-driven personalization—trying to sense who’s visiting, why, and how best to help. It’s not just innovation for the sake of it—it’s about staying one step ahead of user intent. And Matteo knows: one new device could flip the whole game tomorrow.

But innovation isn’t always a straight line. Matteo opened up about one of his past ventures, an app called UpYears, that never quite made it. It fizzled—but he doesn’t see it as a failure. “It changed my mindset,” he reflects. Thanks to a startup incubator in Milan, the experience gave him a crash course in product development and business validation. It also taught him something priceless: don’t cling too tightly to a single plan. Instead, try, fail fast, and adapt. That mentality helped shape every move since—including the launch of Silver Skin, another Playground-born venture.

When asked what advice he’d give to a nervous first-time founder, Matteo doesn’t sugarcoat it. “Fear and anxiety are part of the game—you just can’t let them stop you.” He points to the stoic wisdom of Marcus Aurelius, embracing challenges with clarity, and staying grounded through the highs and lows. His advice? Expect bumps. Stay balanced. And surround yourself with the right people. Because success, he believes, isn’t just about bold ideas—it’s about who you share the journey with.