A Startup, 35 Years in the Making

I've built brands for other people most of my adult life. Big ones. The kind with budgets that would make your eyes water and boardrooms where you couldn't see the table for lawyers. But the moment I understood what a brand actually was, what it could mean to someone, happened on a tarmac in Ibiza in 1999, and it had nothing to do with business.

The doors opened and the heat came in. Not the dry heat of an air-conditioned conference room or the synthetic warmth of a hotel lobby. This was Mediterranean heat, the kind that carries salt and pine resin and something else you can't name but your body recognises. My shoulders dropped about six inches before I reached the terminal building.

I didn't know it then, but I'd just found the thing I'd spend the next twenty-five years trying to bottle.

Learning to Ride a Bike, on Everyone Else's Bike

Thirty-five years in the sports and lifestyle sector teaches you things that no MBA covers. How to read a room in Tokyo when nobody's saying what they mean. How to kill a product line that's making money but diluting the brand. How to sit in a meeting at Kering or TPG and translate "cultural capital" into numbers that private equity understands.

At DC Shoes, I watched a skateboarding company become a cultural force. Not because we had the best ads. Because the riders were real, the product was honest, and the kids who wore it felt like they belonged to something. That was the first time I understood that a brand isn't what you sell. It's the feeling people get when they recognise each other.

Reebok taught me scale. How to operate across continents, how to manage supply chains that span twelve time zones, how to make decisions that affect thousands of people you'll never meet. It also taught me what happens when a brand loses its identity chasing market share. The numbers go up, then the soul goes quiet, then the numbers follow it down.

Fox Motocross was the opposite. Niche obsession. A community so loyal they'd tattoo the logo on their forearms. I learned that depth beats width, every time. A hundred thousand people who would walk through fire for your brand are worth more than ten million who vaguely recognise your logo.

Spyder showed me premium done right. Not premium as a price tag. Premium as a promise. When someone buys a Spyder jacket, they're buying the conviction that the thing will perform at altitude, in weather that would break lesser products. That's not marketing. That's engineering plus trust.

Advisory work with Kering, Oaktree Capital, and TPG gave me the view from the other side of the table. How capital evaluates brands. What makes investors lean forward. What makes them walk away. The answer, consistently, is authenticity. They can smell it. They can also smell the absence of it from three continents away.

All of this was useful. All of it was valuable. None of it was mine.

The Tarmac

I kept coming back to Ibiza. Every year from 1999, sometimes twice, sometimes three times. Not for the clubs, though I did my time there. For the morning after. For the north of the island where the road narrows and the only sound is goat bells and your own breathing. For the fish restaurants with no sign on the door where the grandmother brings you whatever came in that morning.

There's a version of this story that makes it sound strategic. Experienced brand executive identifies gap in premium beachwear market, relocates to aspirational Mediterranean destination, launches direct-to-consumer brand leveraging existing industry relationships.

That's the investor deck version. Here's what actually happened.

I was on a flight home from another board meeting. Another city I could barely remember arriving in. Another hotel room where the minibar was the most personal thing in it. And the question arrived the way the important ones always do, not as a revelation but as something that had been sitting in the corner of the room for years, waiting to be noticed.

If I know how to build brands for everyone else, why haven't I built my own?

It wasn't more complicated than that. No dramatic exit, no Jerry Maguire moment. Just a clear, quiet understanding that the next chapter needed to be written in first person.

The Name

We moved the family to Ibiza permanently in 2009. My wife thought I was brave. My accountant thought I was mad. Both were probably right.

The vision came first. A premium men's beachwear brand rooted in the island, built on authenticity, designed to capture the feeling of being here. Not the party. Not the DJ. The morning. The water. The moment your shoulders drop and you remember what your body feels like when it isn't carrying a laptop bag and fourteen unread emails.

The logo came next. Then the product. Then the fabrics, the prints, the silhouette, the details. I knew what a premium swim trunk needed to be because I'd spent thirty-five years watching brands get it right and get it catastrophically wrong.

The name came last.

I was watching Syd and Rex play on the beach. Just two boys, brown from the sun, racing each other to the water and back. Not performing. Not posing. Just being completely, unselfconsciously happy in the way that children are before the world teaches them to check.

Syd and Rex. The brand was always about this. Not swim trunks. The feeling of the swim trunk moment. Two boys on a beach, their whole summer ahead of them, not a care that doesn't dissolve in salt water.

I wanted to build something that carried that feeling. Something a man could pull on at 7 a.m. and know, without thinking about it, that the day was going to be good. Not because the trunks were expensive. Because they were connected to a place, a person, a memory of standing at the water's edge with nothing to prove and nowhere else to be.

The Bet

Starting a swim trunk brand on an island sounds romantic until you price the logistics. Production in Morocco because the craftsmanship there is genuine and the relationship with our team goes back to the beginning. Fabric sourced through SeaQual, because if you're going to make products from the ocean, they should give something back to it. Distribution from a 140 square metre warehouse on the outskirts of Ibiza Town that doubles as an office and occasionally a meeting room when we stack the boxes differently.

The first validation came from a display cabinet. Literally. A single display unit in an Ibiza hotel in 2011. We sold enough in the first month to know we weren't imagining things. People wanted this. Not because we told them to want it. Because they picked it up, felt it, asked where it was made, heard the story, and bought it. Then came back the next summer for more.

The pop-up store came next, then the concept store on the main road at Can Bellottera. That store taught me more in two years than any boardroom ever did. Ninety-two percent traffic conversion. Not because we had fancy retail design. Because the product was right, the story was real, and people who walked in were already halfway to buying because they'd already fallen in love with the island.

Was it mad? Moving a family to a Mediterranean island to start a swim trunk brand?

Maybe. But thirty-five years in this industry taught me one thing that never changes: the brands that last are the ones built on something true. Not a market gap. Not a trend report. Something the founder would do even if nobody bought it.

I'd have made these trunks for my boys anyway. The fact that other people want them too is the business. The reason they exist is personal.

Every Pair Carries All 35 Years

There's a lot in a pair of Syd & Rex swim trunks that you can't see. The DC Shoes lesson about community over marketing. The Reebok lesson about supply chain integrity. The Fox lesson about niche obsession. The Spyder lesson about premium as promise. The Kering lesson about what capital looks for in a brand.

You just see the trunks. The print. The fit. The way they dry fast and hold their shape after a summer of salt water and sun cream and being thrown in a rental car with sand still in the pockets.

That's as it should be. The best brands don't explain themselves. They just work. And when someone asks where you got them, you tell a story. About an island, a founder, two boys on a beach, and a bet that took thirty-five years to make.

Let your shoulders drop.

🎵 Listen While You Read

We made a playlist for this one. 90s trip-hop, Balearic electronica, and the reflective kind of music that sounds right on a long drive through the hills above San Juan. Search "The Long Road - Syd & Rex" on Spotify.

The Origin Story is a regular column in The Journal. Founder narratives, industry lessons, and the backstory behind a brand named after two boys on a beach. First person. Honest. No polish.