Profile in Action — How A 26-Year-Old Took Elvis On His First National Tour And Came Home A Millionaire

The defining project of Jerry Weintraub’s life came to him in a dream.

In it, the marquee of Madison Square Garden read: Jerry Weintraub Presents Elvis Presley. Of course, when Jerry told his wife the next morning he wanted to take Elvis Presley on the road, she told him he was crazy. He didn’t even know Elvis.

At this point Weintraub was already a successful player in showbiz, running his artist management firm, Management Three, with Bernie Brillstein and Marty Kummer. His was a classic rags-to-riches Hollywood story: born in the Bronx, started in the mailroom at Lew Wasserman’s MCA agency, later becoming Wasserman’s assistant, and then going out on his own to carve his path in Hollywood.

Even though he managed artists like Jackson Browne, Jimmy Buffett, and his wife, Jane Morgan, Weintraub was delusional to think he could convince Colonel Parker, Presley’s prickly manager, to take Elvis on his first national tour. The idea was an insult to pipe dreams.

Elvis had spent most of the 1960s acting in films and making soundtracks for them. He’d been largely been written off as a serious musician and Elvis himself questioned whether he had the chops to perform again until he famously killed it in his 1968 Comeback Special on NBC—his first live performance since 1961.

But Jerry literally had a dream, and so he called Colonel Parker and pitched him on the tour. Of course, the Colonel shut him down. Elvis hadn’t been on tour in years, and he wasn’t about to start now. And when that time came, the Colonel would have his pick of the best people in the entertainment world for the gig.

Undeterred, Weintraub would call Colonel Parker every day for at least a year, hoping that if the Colonel did decide to take Elvis on the road, Jerry Weintraub would be the first name the Colonel thought of.

Then one morning, the phone rang. It was the Colonel. He wanted to know if Jerry still wanted to take his boy out on the road. After Jerry said yes, the Colonel gave him his terms: deliver $1 million to him at the roulette table at the Hilton International Hotel in Vegas by tomorrow.

Imagine finally getting the deal, after persisting in the face of ridiculous odds and daily rejection, only to be hit with terms you couldn’t possibly meet. There’s a Haitian proverb, “Beyond the mountains, there are more mountains.” While Jerry had reached one summit, it revealed another one he’d have 24 hours to climb.

At the time, Weintraub didn’t have anything close to a million dollars, which was a lot of money back then. So he did what he did best: got on the phone. He called everyone he knew, hoping someone knew someone who could help him pony up the cash.

Late into the night, a friend returned his call. There was a guy named Lester Smith who owned a lot of radio stations and was a huge Elvis fan, he might be willing to front Jerry the money. He called Smith and made the pitch of his life. Lester Smith clearly loved Elvis because he agreed to the deal without signing a contract or even meeting Weintraub. There simply wasn’t time.

Jerry landed in Vegas the next morning and delivered a cashiers check to the Colonel for $1million. Jerry Weintraub was a 26-year-old talent manager and he would return from Elvis’s first national tour a millionaire. Because of Elvis’s successful tour, Weintraub would later run tours for Frank Sinatra, Bob Dylan, Led Zeppelin, and John Denver. Later in life, he became a movie producer with hits like Nashville, Diner, The Karate Kid, and Oceans 11.

Weintraub would write in his memoir, When I Stop Talking You’ll Know I’m Dead: “When the man says no, pretend you can’t hear him. Look confused, stammer, say, ‘Huh?’ Persistence—it’s a cliche, but it happens to work.” How many times have we quit after a single rejection? Or failed followed up on an email after not getting a response? Or not even reached out for fear of being rejected?

Colonel Parker rejected Jerry Weintraub so many times that when Elvis was ready for the road, he remembered Weintraub’s name. After learning of Weintraub’s persistence first hand during the Oceans films, George Clooney called him a hurricane, a force of nature that could not be stopped. Too often we worry about hearing “No”, bugging busy people, or looking pushy when going for something we really want. It’s during these apprehensive moments, we’d do well to remember Jerry Weintraub, the hurricane that could move mountains.

Get two stories like this every month in your inbox by signing up at this link for the Profiles in Action Newsletter. Each one comes with further recommended reading based on my research, including books, articles, and interviews with the subject. Use the lessons within to get unstuck, keep plugging along, or do that thing you’ve always wanted to do.

This was previously published on Medium.

Profile in Action — On to the Next One: How Jay-Z Used Mentors to Get to the Top

Jay-Z was raised by a single mother in the Marcy Projects of Brooklyn. His father flew the coop when he was 10, and Jay-Z was largely left to fend for himself. With origin stories like this we often attribute outliers to God-given talent or an unceasing drive for success. 

It’s true that Jay-Z possessed both of those in spades, but he was also humble and savvy enough to recognize when he crossed paths with someone he could learn from to reach his final destination.

First, it was Jonathan “Jaz-O” Burks, an older rapper from Marcy who recognized himself in the young, hungry rapper. Jaz-O helped Jay-Z improve his rap skills, teaching him not to practice on his craft on the corner, so that when he would spit in the streets or a club people would wonder how he made it look so easy. 

Jay-Z then partnered with his high school classmate and fellow dropout DeHaven Irby to learn the drug game in Trenton, New Jersey. While selling cocaine he developed his penchant for profits, eventually expanding their operations to Maryland and Virginia where there was more room to breathe away from New York.

Later he would persuade rapper Big Daddy Kane to let him travel on his tour bus, earning his spot by rapping during intermissions at his shows that featured artists like Queen Latifah and Tupac Shakur.

Jay’s third and most fruitful mentorship was with Damon Dash. Dash was from Harlem and a hustler in his own right as a club promoter. Dash was skeptical of the rumors about Jay-Z’s talent at first, unable to fathom there was a rapper that good from Brooklyn. But upon meeting Jay, he knew he had the goods. 

Soon after partnering up, Jay and Dash tried selling Jay-Z’s legendary first album, Reasonable Doubt, to record labels, but they were met with a series of rejections. Undeterred, Dash decided he and Jay would start their own label, Rock-A-Fella Records and sell the album themselves.

They started by selling Reasonable Doubt out of the trunks of their cars, going anywhere to sell the album, even barbershops. 

Reasonable Doubt sold 420,000 copies in its first year.
With the hype they built from their ground game, they were able get an unheard of deal with Def Jam Records for the second run of Reasonable Doubt, splitting only a third of the profits with the company. Years later, Jay-Z would become CEO and president of Def Jam Records, usurping his mentor Dash when he bought out his stake in their apparel company, Rocawear.

Jay-Z’s friends and collaborators have attributed his ability to spot knowledgeable people and quickly absorb their wisdom to his humility and curiosity. By holding onto what Buddhists call “beginners mind,” or a child-like attitude of openness and lack of preconceptions, Jay-Z quickly recognized people who knew the landscape and ingratiated himself with them.

 Upon happening upon new territory, whether in hip-hop or drug dealing, Jay-Z was able to learn from, and quickly surpass, mentors who had been working at it far longer than he had. Instead of trying to go it alone (he probably could’ve), or being intimidated by people with more power and status, which would have flattened his rise, he swallowed his pride and sought out partners in crime.

 By ingratiating himself with people higher on the food chain, constantly asking questions, and internalizing their wisdom, Jay-Z was able to go from street hustler to the CEO of Def Jam Records in 10 years.

Get two stories like this every month in your inbox (before they’re published here) by signing up at this link for the Profiles in Action Newsletter. Each one comes with further recommended reading based on my research, including books, articles, and interviews with the subject. Use the lessons within to get unstuck, keep plugging along, or do that thing you’ve always wanted to do.

This was previously published on Medium.