Wednesday night in New York City, Brett Young was both country singer and entrepreneur, performing at a celebration for the new Southwest Rapid Rewards Performance Business Card. He was also part of a panel discussion with executives from Chase, Southwest, Google and Facebook.
When he landed his record deal, Brett admits he wasn't exactly prepared to run his own business.
"Nobody ever goes, 'Oh, by the way, you've just become the CEO of your own company'... At first it was terrifying," he confesses.
Before that, most of Brett's experience was as a bartender.
"The business didn't rest on my shoulders. If I poured I good drink, I got tips..." he recalls. "It's such a growth experience... to be put in a situation like this."
In addition to his musical endeavors, Brett stumbled on another venture: making clothing bearing the name of his publishing company, Caliville -- a combination of California and Nashville.
"Me and two buddies started putting it on hats and t-shirts," he recalls. "The hats were getting stolen off people's heads in Nashville before we were even putting them for sale on a website, which is all we've ever done."
"I'm California and Nashville," he explains. "People are seeing it and...going, 'That's cool, I like that.'"
"We can't even take credit for it. It was an accident, but it's because we've been ourselves from the beginning," he concludes.
Now as Brett and his wife Taylor prepare to welcome their first child this fall, he believes running his own business will even make him a better father.
"I don't think...we would be this confident and secure in what we have coming in our future, if I hadn't been pushed so much by being put in this position as a business owner," he tells ABC Radio.
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