Teddy Robb’s big “whoa” moment arrived at his meet-and-greet line during Nashville’s CMA Fest this summer.

“There was a girl from Texas,” the 29-year-old up-and-comer tells PEOPLE. “I say, ‘Oh, you came from Texas for CMA Fest?’ And she says, ‘No, I came from Texas to seeyouplay.’”

Whoa.

“Okay,” Robb says he thought, “this is actually happening.”

“This” is the career that he’s been dreaming about, hoping for and working toward since the day he moved to Nashville soon after college. And “this” is what happens after you sign with hit-makerShane McAnally‘s Sony Monument Records label and rack up 30 million streams on a song that’s now steadily gaining radio airplay.

Susan Berry

Teddy Robb

“I got rid of Plan Bs,” says Robb, who holds a bachelor’s degree in business from Kent State. “That was when everything changed. I remember actually having kind of an argument with my dad, and he was like, ‘I’m supposed to worry about you. I need to know that you’re going to be taken care of.’ I said, ‘Dad, I’m either gonna make it or I’m gonna die trying.’”

The spark for all this fire arrived late for Robb, not until midway through college. A high school football standout in his hometown of Clinton, Ohio (outside Akron), Robb thought he had a sports career ahead of him. But college football drained him of his love for the game — he quit after two seasons — and a failed relationship sent him to the guitar he’d messed around with in middle school and then put aside.

“People ask, ‘How’d you learn to play guitar?’” Robb says. “Well, you gotta get your heart broke first, because that’s the easiest way to want to dive into it. If you’re feeling sad, you don’t want to be out in bars and you don’t want to be around anyone. I just sat in my room, and I would practice for hours and hours, trying to figure out how to play music.”

Teddy Robb.Susan Berry

Teddy Robb

A turning point arrived one day when Robb heardGeorge Strait‘s “Troubadour” for the first time, on the car radio.

It wasn’t just that Strait was singing about the romantic life of a traveling singer. What struck Robb was that the lyrics were moving him — so much so that he had to pull over. “It was that moment where everything kind of stands still,” says Robb. “I was like, wow, I feel alive.”

And then Robb’s mind formed a question: Could he ever make someone else feel that way with his own song?

One more turning point arrived in a business class when the professor asked Robb yet another fateful question: “If you could be anything, in your wildest dreams, what would you be?”

Robb surprised himself when he blurted out: “I’d love to be a country singer.”

But when the professor learned that Robb had never even sung in public, he offered a challenge: “Go sing at an open mic and come back and tell me how you liked it.”

Robb accepted and discovered, to his delight, that “I got the craziest adrenaline rush ever.” The only thing he could compare it to was the highs he’d experienced playing football. “It was like, oh, I got what I loved about football back,” he says.

Paid gigs around his hometown soon followed, and after graduation, he finally took the plunge, packing up for Nashville and setting his eyes on the prize.

Teddy Robb.Matthew Berinato

Teddy Robb

His do-or-die mindset eventually translated into 300 gigs a year, playing cover songs at Nashville clubs, weddings, parties and any other place that had a mic and an audience. (Please don’t ever ask him to play “Wagon Wheel” or “Sweet Caroline” again.)

“I was just pounding it five, six, seven nights a week playing,” Robb says. Days were spent in songwriting sessions, where he worked to find his own musical voice.

An avid outdoorsman who loves to fish, hike and snowboard, Robb stepped away from the grind for a few months to take a regular singing gig in the Colorado ski resort town of Vail. Incredibly, that’s when he finally got his break with a chance encounter with a vacationing Grammy exec.

“He gives me a card,” Rob recalls. “He ends up connecting me back to Nashville, which is where I meet a producer. We start working on a project, and the next connection is signing a record deal with Sony Monument.”

This summer, Robb has been out pitching his single on his first radio tour — an industry fact of life that has a well-deserved reputation for being a grind. Robb, though, has been having a blast.

He thinks back to that 300-shows-a-year cover singer, and wishes he could tell him, “’You’re going to get the opportunity to present yourself to radio stations all across the country.’ I would have been, sign me up! I won’t let myself ever complain about it.”

Teddy Robb

That sunny nature — he has a smile that may well be contributing to global warming — is now helping him navigate all the twists and turns of this break-out moment. “I’m not afraid to say what I want out of life and put it out into the universe and believe that it’s going to come back to me,” Robb says. “When you have that intention and that positive outlook on life, I believe you’ll attract that kind of thing.”

Case in point: Not too long ago his publisher arranged a writing session with Leslie Satcher, co-writer of “Troubadour,” not knowing the song’s place in Robb’s heart.

Of course he shared the story with Satcher. She got emotional. As Robb recalls, she told him, “You know, sometimes I think I want to stop writing songs, and then somebody tells me that, and it makes me keep going.”

Today, Robb is more intent than ever to create music that gives listeners their own “Troubadour” moments.

“I get to actually impact someone’s life,” he says. “I don’t think there’s anything more important than that.”

source: people.com