KASON LESTER doesn’t have to go far to remember who he is. He’s a hometown guy, born and raised in Lebanon, whose heart beats for Middle Tennessee, where red dirt roads lead to family farms and downtown squares brim with hometown charm.

His grandfathers built businesses from the ground up, carving out livelihoods with a mixture of hard work and a sense of pride.

“It’s a great environment for businesses,” Lester said.

He intends to take that inspiration and leave a legacy of his own. Music didn’t come to him the way it does for many artists. There was no church solo at 5, no middle school talent show standing ovation. Instead, creativity lived in the margins of his 20s — private moments with a guitar, lyrics scribbled down for no one but himself.

“I always wrote songs and played guitar,” he said.

But performing didn’t come until later. He wasn’t chasing fame; he just wanted to create.

He started small, just creating for the love of it. But the stage got bigger, until even American Idol took notice.

One minute he was writing songs at home; the next, he was flying to Hollywood for one round of the competition and to Hawaii for another.

“It was a total God thing,” Lester reflected. “Not something I could’ve ever done on my own.”

The experience was surreal. He referred to it as “a crash course in entertainment,” exposure, and trusting your gut in front of millions. But more than that, it reminded him of something important: Sometimes the path you’re meant to take finds you — even if you weren’t chasing it.

Still, for all the bright lights and cameras, the moment that stands out most in Lester’s music journey happened a lot closer to home.

“Getting to play with Charlie Daniels was a big one,” he said. Daniels, a Tennessee legend himself, was kind to Lester and encouraged him in those early days.

Daniels treated him like he belonged, like this whole crazy idea of pursuing music was something worth believing in. And sometimes that’s all it takes: Someone seeing something in you before you can see it in yourself.

“It was a great learning experience,” he said.

Perhaps more importantly, it was confirmation. Maybe this path wasn’t just a daydream after all.

But the stage is just one of Lester’s mediums.

Recently, he opened New Era Vintage, a passion project turned business venture, on Lebanon’s square. And it isn’t your average shop.

It’s part collectible den, part nostalgia trip, and part altar to all things wonderfully eclectic and deeply inspiring.

From the moment you walk in, you’re hit with nostalgia and color. Bits of history, pop culture, and creativity fuse together. It’s a mood, a feeling, a flashback. The store consists of vintage collectibles, old-school band tees, funky ‘90s toys, and vinyl records with tattered edges and stories engraved in their grooves.

“It’s a vibe for sure,” Lester said. “I’ve always loved cool, weird, vintage things,” he said.

But he’s really offering a feeling of rediscovery, play, and memory.

“Our goal is for you to walk out with something that inspires you, sparks creativity, or just makes you feel cool.”

This isn’t Lester’s first dance with vintage goods. He ran a booth at Antiques on 231 for years, curating pieces. But New Era Vintage is different. It’s louder, bolder, and more alive — just like the music he continues to write and record.

It invites people to rediscover the joy of expression, whether through fashion, fandom, or flipping through old records. It’s a love letter to the past, signed with present-day intention.

So, what would he say to someone sitting in a dream who’s too nervous to take the first step?

“If it gives you life, it’s probably worth working to bring it to life,” he said.

He believes in following that inner tug, even when the path ahead looks foggy, and especially then. Failure isn’t a stop sign but a rite of passage. He’s lived long enough to know the best stories don’t come from perfection. They come from persistence.

“A creative being made us,” he said, “and He assists in our creative efforts.”

For Lester, the process is spiritual. And failure is not the enemy.

“It plays a crucial role in every success story.”

Looking at Lester now, a singer-songwriter, vintage shop owner, and small-town creator, you wouldn’t know he once hesitated to share his voice.

But Lebanon raised him to believe in community, legacy, and showing up for the life you want to build.

And whether it’s in a song, a collectible jacket, or a serene moment between guitar strums, Lester does just that with each vintage gem and honest lyric. GN