This episode of The Grumpy Cyclist Talks Music features Olly, a friend of Chris Cole, who previously joined us for a podcast back in the summer of 2025.

Olly, who spends most of his year living in the UAE, took some time while visiting the UK to sit down and talk about his life and his deep connection with music. Growing up, his early influences were shaped at home—his mum leaning toward Rod Stewart, while his dad filled the car with bands like Fleetwood Mac and Electric Light Orchestra. Safe to say, Olly didn’t have much choice in the matter back then.

As he found his own taste, bands like Blink-182, Feeder, and Sum 41 pulled him further into guitar-driven rock. But the real turning point came in 2012, when he saw Bruce Springsteen live at the Isle of Wight Festival. That performance sparked what can only be described as a full-blown love affair—one that’s arguably made him one of Springsteen’s biggest fans (much to the amusement of his friends).

Olly dives into the albums that have shaped him, his experiences seeing Springsteen live multiple times, and the sheer energy of shows that can stretch to three or four hours while still selling out stadiums worldwide.

We also get into his appreciation for folk music, and an honest take on live performances—including why seeing Bob Dylan ranks as one of the most disappointing gigs he’s attended.

The conversation broadens into the realities of the music scene—how tough it can be for bands to break through in the UK, compared to Olly’s experiences in places like Texas, where live music thrives in local bars almost every night of the week, often with strong support from local crowds (and, unsurprisingly, a heavy dose of country music).

It’s a thoughtful and personal insight into what music really means to Olly—how it shapes identity, connection, and experience over time.