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What Every Start-Up Can Learn From Country Music's Most Anticipated New Artist

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Every once in while in every industry someone comes along who you know is about to go viral. ‘Personal calculus’ is the main reason why venture capitalists back individuals first, and ideas second. The music industry is no different—ever mining for the next Blake Shelton or Beyonce the same way tech angels treasure hunt for the next game changing, Silicon Valley start-up.

If you buy this line of thinking, Drake White may just be about to become country music’s next Uber. And why every entrepreneur in every industry should take a few business lessons from this northern Alabama good ole’ boy.

I first meet White at 6:30 am in the lobby of a Brooklyn hotel across the street from the 24-hour Atlantic Avenue subway line. It’s a strange place to meet one of Nashville’s up-and-coming stars: still foggy from four hours of sleep (the train rumbles by every 42 minutes) and surrounded by hipsters who likely wouldn’t know Kenny Chesney from Times Square’s Naked Cowboy.

I’ve been a shameless country music fan for decades, but I don’t have a pulse on Music City’s start-up scene so I’d never heard White’s name until two weeks earlier when White’s PR company invited me to join him on the launch of his debut record, “Spark”, which was just released on August 19th by Big Machine Label Group. White’s record launch is about to take us 3,070 miles between five cities (NYC, Dallas, Wichita, Denver, and Los Angeles) in 24 hours by private jet (sponsored by Cessna) to perform five acts of paying-it-forward charity (more on this later).

When the elevator door opens for some reason I expect an entourage to spill out. Instead, there’s White—beat up acoustic guitar in one hand, beads on his wrists, two cowboy hats on his head, Ray-Bans already on (it’s still before sunrise), and a backpack in his other hand that he’s had since he went on a four-month walkabout in New Zealand six years ago.

“What’s up? What’s up”, White yells at me and two other writers across the lobby before giving me a fist bump. “Let’s do this!” If it’s true that you can take the measure of a man in the first ten seconds, White will never have an entourage no matter how big he goes.

White’s country music autobiography looks like it’s scripted to be a textbook American country-kid goes big success story. He grew up Hokes Bluff, Alabama, a town of barely 4,000 people northeast of Birmingham in the Appalachian foothills. He played wide receiver on his state championship football team, eventually marrying the high school sweetheart he could never have when he graduated. He took a few guitar lessons when he was 12 before deciding to teach himself.

“I learned how to play guitar to keep people’s attention around a fire,” says White, recalling his days growing up on four-wheelers, hunting, and fishing. “Playing music was also a way for us to stay out of trouble in a small town.”

If this sounds vaguely similar to a Palo Alto kid growing up writing computer code in a garage while his parents shuttled off to Hewlett-Packard during the day, it’s because it is. White’s gravitational pull to music and songwriting was genetically unavoidable, beginning with his grandfather, the town’s local preacher, who was famous for his boisterous sermons and using music as a way to elevate his flock to a place bigger than themselves.

“My grandfather taught me how to enjoy the spiritual realm of life,” White recently told The Boot. “I listened to him sing, and his sermons, and his scripture for a long time. So it can’t help but seep into my musical palate. The old soul, the gospel, and all the growls and kind of vibratos that you hear (in my songs), it’s because I grew up on Sunday mornings listening to it.”

White’s raw, gravelly, sedimentary sound—think Joe Cocker meets Jack Johnson—is for many critics salvation from the pop-trending “Bro country” that’s dominated the airplay charts for the past few years. Rolling Stone has praised White’s gospel howl as “electric” and “energizing”. The Huffington Post recently named White one of the “Top Country Artists To Watch in 2016”.

Predictably many of the standard red-dirt clichés have already been exhausted to describe White’s traditional country voice and songwriting: soulful, expressive, infectious, riveting. Similar, ankle-deep adjectives were heaped on Roger Federer when he exploded onto the tennis scene in 2001. But as any tennis fan knows, there is no vocabulary that can capture what it’s like to watch ' FedEx'  play live. Many Nashville music critics are now saying the same thing about White.

White at FDNY Station 288 in Queens. Courtesy of Peter Lane Taylor

It’s 7:30 am when we pull up to FDNY/HAZMAT 1 Station 288 in Queens. I'm still half way into my first cup of coffee. Most of the firefighters there who have shown up for breakfast with White have been up all night. White is ready to rock.

15 years ago on September 11th, 2001 FDNY Squad 288 watched American Airlines flight 11 hit the North Tower at 8:46 am right in front of their eyes. They didn’t even wait for the call. They suited up and drove straight to Ground Zero. The South Tower collapsed at 9:59 am after burning for 56 minutes. 27 minutes later the North Tower collapsed. Twenty-one firefighters from FDNY Squad 288 died that day, 53 children from which now in their teens and having children of their own no longer have fathers.

Given Station 288’s history, you wouldn’t be surprised to walk into an awkward moment first thing in the morning when some hotshot, up-and-coming musician with the press in tow shows up for a photo op at a FDNY station a few weeks before 911’s fifteenth anniversary. But that’s exactly the moment you would learn why the ‘personal calculus’ on White is that he’s on the verge of going big precisely because he keeps it small and real. If this video of White playing one of the songs off of his new album Spark in front of Squad 288 with the memorial plaques of their fellow firefighters lost on 911 in the background doesn’t make you tear up your heart may no longer have a pulse.

“Drake wins live,” says Trey Wilson, White’s manager. “Whether he’s playing on stage at Fenway (Park) before 20,000 people or around a campfire in front of a dozen friends. In music these days, glam is out and authenticity is in, and it’s Drake’s honesty and spirit that’s creating a narrative people can connect with. Being on tour and on the road for Drake is like a political campaign. When he’s out there shaking hands and kissing babies, a cult of personality just naturally follows.”

Back in the fall of 2012, the thought that White would be kissing any babies “on tour” besides his own nieces and nephews in a local bar seemed like a long shot. White was dropped by his first record label on October of that year on his birthday before he could put his first album together. For a thin-skinned musician or entrepreneur that type of early rejection would typically be soul crushing. Instead White pulled out his punching bag—literally—dropped 25 pounds, got down to 8% body fat, and started writing songs every day, determined to break through Nashville’s glass ceiling.

“That’s what art does to you,” White says. “Iron sharpens iron and you just keep on punching. (You) keep on punching until your product comes out. I’m gonna be an artist until the day I die. Don’t matter if I make money at it or I don’t. That’s the blessing and the curse. I do this because this is what I am supposed to do."

30,000’ in the air in a private jet is an unexpectedly revealing place to take the measure of person’s humility, or more accurately in White’s case, their perception of fame and success. Some people can’t get over their own inner battle with feeling privileged so they miss out on the pure joy of the moment. Others try too hard to make it seem like they fly private every day. Watching White stare out at the Rocky Mountains on the third leg of our cross-country journey from the Wichita Boys & Girls Club to the Denver VA Hospital, it’s obvious that the man takes nothing for granted while still appreciating everything that he’s earned the hard way.

“There are many different paths. And mine was just in a van with a trailer,” White says. “I wanted to have a group of guys that went out and did it the hard way and learned from people like Zac Brown and Eric Church, and these guys that did years of hard touring. There were definitely times where I was like, screw this. But now that I look back it’s a perfectly fitted puzzle piece.”

White’s ascent to becoming one of Nashville’s most anticipated country musicians in years would sound familiar to any entrepreneur precisely because it’s been thoroughly complicated and circuitous, meandering through an engineering degree at Auburn and a four month soul-searching trip through New Zealand in 2010, eventually landing him right back where started—playing music around a campfire. The only difference now is that the campfire has 20,000 people around it.

"Drake outworks everyone I know in Nashville these days,” says Wilson, “Because he knows he’s got one shot at this. But music isn’t a path to success or fame for him. He wants to produce a body of work that he’s proud of, that his wife’s proud of, and he knows that success will follow. Drake also has this rare combination of confidence and humility—and it all comes back to playing guitar and singing songs around a fire.”

Drake White and Good Morning America's Jesse Palmer. Courtesy of Tony Morrison for ABC

A year before White was cut by his first label, Wilson saw White play for the first time in a tiny, hole in the wall bar in Atlanta at the urging of a friend in 2011.

“It was literally the size of a living room,” Wilson recalls, “It was his girlfriend at the time in the audience, a few family members, two random people, and me and a friend, and he was playing with two other guys with a 3-piece drum kit and a bass. But he rocked like he was playing in front of 50,000 people. He eventually ditched the mic and just played unplugged and freestyle at the edge of the stage, and his energy . . . Man the energy.”

Give Wilson credit for spotting talent where others had given up before. When White became a free agent in 2012 Wilson pounced. You can’t say the rest is history because White is just starting to write his own. But White’s a pretty hot bet in Nashville right now. In June 2014 he signed with DOT Records, a subsidiary of Big Machine Label Group and his Music City stock has been on a near vertical curve ever since, simultaneously touring across America with some of country music’s most popular acts like The Zac Brown Band and Dierks Bentley. White’s grandfather would be proud. If you’re lucky enough to have a dream and to be good at it, never give up.

The byproduct of White never giving up is his debut album “Spark” which has been over two years in the making and features 11 of 12 songs written by White, a rarity in country music these days when many artists rely on independent songwriters.

“The idea of starting a fire from a tiny spark has always been so intriguing to me,” White explains of why he named his album. “That’s the way I have always lived my life; starting with a small plan and then it becomes this dream I didn’t even know to dream.”

So far White’s spark metaphor seems to be working from a business standpoint. "Spark" has already hit #1 on the iTunes Top Country Albums chart, and its first track released to radio, “Living The Dream”, is sitting currently at #20 on the country music charts. On August 23rd, White played ABC’s Good Morning America in Times Square. Not bad for a country boy from Hokes Bluff.

When we touch down in Los Angeles 3070 miles, five cities, and 19 hours from where we started in Brooklyn earlier in the day, White still somehow has some pep in his step getting off the plane. I’ve got a screeching headache and don’t want to talk to anyone. But fishing and protecting America’s oceans and rivers are close to White’s heart, and he’s got one more set to play.

When we get to Oceanside north of San Diego an hour later just after 10:00 pm Pacific Coast time, there are a few dozen families and kids remaining around the campfire sponsored by Salt Life and the Western Surfing Association. White still has his sunglasses on. He walks up to the crowd, kisses a few babies, and says a few words about how important the work is that Salt Life is doing around the world. And then he cranks it out again, free styling the lyrics to “Living The Dream” with references to fishing, surfing, and living on the water—playing to the crowd. And building his cult of personality.

It’s a fitting ending to a day of “Giving The Dream” when a blonde, surfer kid probably no more than 8 years old throws another log onto the bonfire just as White wraps up his last song. That’s ultimately the whole point about starting a spark. Music wouldn’t be worth a 1/10th of what it is to White if it didn’t provide a platform for giving back. I know. This sounds like it was queued up right from the record label or management team. But in White’s case, paying it forward is as much a part of his genetically-inherited identity as his vocal range courtesy of his grandfather.

White at the North Texas Food Bank in Dallas. Courtesy of Peter Lane Taylor

“My grandfather taught me how to be a gentleman,” White recalls at the end of the day. “Disconnect. Put down your phone. Put down your computer. Listen to the frogs. Watch the sun set. Stand up tall and stand up for what you believe in. To watch a man or a woman’s face instantly light up when a chord is strung is a powerful thing. I’ve seen it literally change people’s expressions on their faces instantly.”

Campfire jam anyone?

For more information on the great work supported by the organizations White visited on his “Giving The Dream” album launch please visit the following websites

Friends Of Firefighters

North Texas Food Bank (in partnership with Ford Community Fund)

The Boys & Girls Club of South Central Kansas

Musicians on Call

Western Surfing Association (in partnership with Salt Life)

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