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The Rich and Famous Reveal Their Struggles at Work — and in Life

Lauren Monitz
23 Millionaires Reveal Their Struggles at Work — and in Life

In their song “If I Had a Million Dollars,” the Barenaked Ladies sing about all the fun and lighthearted things they could buy with that kind of cash. That being said, making a million dollars is actually quite a monumental task. Building a net worth of that size takes an immense amount of planning and time.

These industry giants and celebrities weren’t always the polished A-listers they are now, and it certainly wasn’t a straightforward trajectory to the top.

Click through to learn more about the struggles these millionaires faced on the job and in life.

Selena Gomez

Occupation: Singer and producer

Net worth: $75 million

One of the most famous millennial millionaires, Selena Gomez has been open about how her personal health struggles have impacted her career. She took time off from her jet-set career due to depression and anxiety associated with lupus, a disease she has struggled with for years.

Gomez has spoken candidly about her road to success, growing up in Hollywood, living with lupus and the issues that led to checking herself into rehab. She told People she was taking a year-long break to focus on “maintaining my health and happiness.”


Tom Brady

Occupation: Football player

Net worth: $180 million

Despite being among the greatest of all time in the football world, Tom Brady struggles to maintain his position in a profession not known for its longevity or job security.

In an interview with GQ, Brady said, “I was the kid that was the 199th pick that never had the body for it. People didn’t think I’d play one year in the NFL, and now I’m going on my 17th year.”

Fighting to play past his prime and chase youth, he’s declared he intends to play until he’s 45, and he uses himself as a case study in his new book, “The TB12 Method.” However, analysts from ESPN consider this quest for physical transcendence a dangerous game.

Kylie Jenner

Occupation: Reality star and cosmetics mogul

Net worth: $300 million

The youngest of the Kardashian-Jenner clan, Kylie Jenner spent her entire childhood on TV.

In an interview with Complex magazine, Jenner was quick to note that “fame isn’t bad,” but growing up in the spotlight can be challenging.

“It’s probably the hardest thing,” she said. “You don’t know who you are. I didn’t know who I was a year ago, and I still don’t know exactly who I am now. You’re trying to grow up and make mistakes and everybody’s watching.”


Sean Combs (aka Diddy)

Occupation: Rapper, actor, producer and fashion designer

Net worth: $885 million

Sean Combs is one of the many celebrities who didn’t grow up with money. But that’s exactly how he got his work ethic. In an interview with CBS, he got personal.

“I was brought up by my mother and my grandmother,” Combs said. “My father was killed when I was 3. And one day, I had, you know, asked my mother for a pair of sneakers. And the look on her face that she couldn’t afford it — it just made me realize that I needed to step up as a man.”

It was that kind of drive that took him from working four paper routes to cleaning gas station bathrooms to topping the Forbes’ list of wealthiest hip-hop artists.

Cristiano Ronaldo

Occupation: Soccer player

Net worth: $460 million

Arguably the best soccer player in the world, Cristiano Ronaldo said his career almost never even got off the ground. In an interview with the Mirror, Ronaldo revealed how he used to sneak out of his dorm to do extra workouts because players and coaches said he was too small.

“It’s true, I was skinny,” he said. “I had no muscle. So I made a decision at 11 years old. I knew I had a lot of talent, but I decided that I was going to work harder than everybody.”

Justin Bieber

Occupation: Singer

Net worth: $285 million

Very few celebrities have had as many public faux pas as Justin Bieber. From erratic behavior to bizarre arrests, the singer fell into a deep hole that fans were unsure he could dig himself out of.

“It might seem awesome from the outside, but I’m struggling,” Bieber told Billboard. “I started going through the motions. I felt like people were judging me all the time. I came out alive. I came out swinging. But I was close to letting [fame] completely destroy me.”

Amy Schumer

Occupation: Comedian and actress

Net worth: $16 million

Amy Schumer makes a living based on her self-deprecating humor, but that doesn’t mean the trolls and insecurities don’t get to her.

“You have days where you’re like, ‘I am a lump of garbage and I should be on a curb,'” Schumer told PopSugar. “Every year you look back, and you’re like, ‘I was so great then and I was stressing about how I look, I just want to get back to that at this point.’ You know you’re going to feel like that year from now.”

Mark Wahlberg

Occupation: Actor

Net worth: $300 million

A triple-threat actor, rapper and producer, Mark Wahlberg is a hustler above all else. Growing up in the spotlight with the musical group New Kids on the Block, Wahlberg became addicted to drugs at a young age.

He told the Chicago Tribune, “I’ve never been shy about sharing my past and the bad decisions I’ve made and being affiliated with gangs, being incarcerated.”

His goal now is to inspire and provide hope that you can always turn it around.


Occupation: Singer

Net worth: $190 million

Even after her successful early albums, the soulful crooner found it difficult to create at the same level. In an exclusive interview with I-D Vice, Adele said she wrote a few songs for her album “25” and got rejected.

“My manager was like, ‘This isn’t good enough.’ Yeah, it knocked my confidence a bit, but I also knew,” she said. “And then I flew Rick Rubin over, to play him the songs and he was like, ‘I don’t believe you.’ That’s my worst fear: people not believing me. So I went back to the drawing board.”

Usain Bolt

Occupation: Olympic track and field

Net worth: $90 million

With a lofty goal to be the greatest athlete of all time, Usain Bolt is not what one would call humble. But that doesn’t take away from how hard he’s worked for what he has.

“Everybody says winning’s easy for me,” he told the Guardian. “I’m like, ‘Why would you say that?’ Yes, it looks easy. But it’s not. There’s a lot of work and dedication. It’s rough. I want people to understand that what they see on the track is because I work so hard to get there.”

Kenny Chesney

Occupation: Musician

Net worth: $190 million

One of the most successful country performers of all time, Kenny Chesney is one of the best examples of starting from the bottom and working your way up. He was fired from one of his first gigs at a local Nashville hot dog stand after only three days.

Even success didn’t guarantee things were going to be easy. Chesney told Hot 20’s Katie Cook about the time after his first No. 1 single took off: “It was a very unsure time of my life. I didn’t really know where my music was going to take me.”

Gordon Ramsay

Occupation: Celebrity chef

Net worth: $220 million

In the kitchen, you’re constantly under pressure. But with three Michelin stars and 35 restaurants under his belt, life couldn’t be better for Gordon Ramsay.

It hasn’t always been caviar dreams, however. As Ramsay explained in a Reddit AMA, “I came out of my training in Paris, after getting my ass kicked in some of the best restaurants in the world. I took some time off … to regenerate.”


Occupation: Singer and media mogul

Net worth: $500 million

Queen B leads a rather private life but has been known to give a rare interview or two on her success as a female artist. In a candid conversation with Elle, Beyoncé recalled her early days with musical group Destiny’s Child.

“The label didn’t really believe we were pop stars,” she said. “They underestimated us, and because of that, they allowed us to write our own songs and write our own video treatments.”

She asserted the label’s lack of faith was exactly what cemented the group’s future. It’s when “I became an artist and took control … we had a vision for ourselves … and created it on our own.”

LeBron James

Occupation: Basketball player

Net worth: $480 million

LeBron James’ success cannot be denied, yet he still struggles with blocking out the noise and judgement. He vented to Slam Online about being viewed as a stat more than a person.

“Where they rank me, who I’m better than, who I’m not better than — I call that barbershop talk,” James said. “That’s gonna happen. No matter if you like it or not, it’s gonna happen. It happens with the greatest of all time […] With Muhammad Ali, it’s who’s better, him or Floyd [Mayweather Jr]? Who’s better, Tom Brady or Joe Montana or Aaron Rodgers or Peyton Manning? It’s barbershop talk.”

Ellen DeGeneres

Occupation: TV personality

Net worth: $490 million

It’s been a whopping 20 years since Ellen DeGeneres shocked the nation as one of the first openly gay LGBTQ celebrities. Uncertain how it would affect her image and future, DeGeneres decided to embrace it.

“I wasn’t sure if I was going to work again, and although I was out, I was still trying to alter myself,” she told the New York Daily News. “I slowly gained the confidence to be authentic, and what I’ve learned about other people is that they strive to be authentic, too.”

Conor McGregor

Occupation: UFC fighter

Net worth: $120 million

From plumber apprentice to championship fighter, Conor McGregor never had it easy.

“When things were really bad I didn’t have a pot to p— in,” McGregor told Rappler. “Really, nothing. I’m not a stupid guy and it was hard standing in a dole queue.”

Howard Stern

Occupation: Radio personality

Net worth: $650 million

While he generally makes his money doing the interviewing, Howard Stern is much less comfortable on camera.

“I hate doing talk shows,” Stern told Jimmy Kimmel in an interview. “It’s so unnatural. Everyone evaluates you. How did he do? Was he funny? Did he pull his pants down? Was he farting? He wasn’t good enough. It makes my neuroses crazy.”

David Copperfield

Occupation: Magician

Net worth: $1 billion

You might know him from his sleight of hand, but this magician is not a one-trick wonder. The recipient of 21 Emmy awards and 11 Guinness World Records, David Copperfield has been named a “living legend” by the U.S. Library of Congress.

Copperfield told Forbes, “I’m blessed and cursed with never being satisfied. … Rarely do I feel completely satisfied with a show. Usually, I obsess about how each little thing can be enhanced, improved. It’s a difficult way to live.”


Blake Ross

Occupation: Founder of Mozilla Firefox

Net worth: $150 million

This young millionaire learned he suffered from an identifiable mental phenomenon by unwittingly clicking on a Facebook article about it. The rare condition is called aphantasia, which Blake Ross described as “being blind in the mind.” Being unable to conceptualize images has made it exponentially harder for Ross to communicate complex concepts simply because of his brain structure.

He described the condition and how it has affected his life in a Facebook post: “I’ve always felt an incomprehensible combination of stupid-smart. I missed a single question on the SATs, yet the easiest conceivable question stumps me … What did you do today? I don’t know.”

Andrew Mason

Occupation: Founder and former CEO of Groupon

Net worth: $230 million

Some CEOs are notoriously figurehead positions and well-versed at passing the buck. Not Andrew Mason. In fact, he perhaps took too much ownership.

“After four and a half intense and wonderful years as CEO of Groupon, I’ve decided that I’d like to spend more time with my family. Just kidding — I was fired today,” Mason stated in his departure letter, as reported by Tech Crunch. “From controversial metrics in our S1 to our material weakness to two quarters of missing our own expectations and a stock price that’s hovering around one-quarter of our listing price, the events of the last year and a half speak for themselves. As CEO, I am accountable.”


Pete Cashmore

Occupation: Founder and CEO of Mashable

Net worth: $20 million

Navigating the digital media landscape is never easy, and sometimes it involves selling off part of your core business. In the company’s major shift from digital publishing to mobile media, Pete Cashmore had to learn to roll with the punches and embrace an uncertain future. The announcement he sent to his team was decisive yet somber.

“Last week we announced a funding round to put Mashable on more platforms, including television,” Cashmore said. “This new focus means we have to change the way our teams are organized, and involved some very tough decisions. …Today we must part ways with some of our colleagues in order to focus our efforts.”

David Karp

Occupation: Founder of Tumblr

Net worth: $200 million

David Karp dropped out of formal high school at 15 and founded Tumblr when he was just 20. He admits the early days were a struggle due to the platform’s unexpected success.

In a Medium interview, Karp explained, “We hit a lot of scaling bottlenecks all at once.” His team had been “adjusting and expanding our infrastructure to handle all this new traffic every month,” he said. But “the traffic … really shot up like crazy.”

The numbers were staggering and unexpected, and a lot of updates planned for subsequent months were forced to happen much sooner than expected, creating a lot of chaos.


Matt Mullenweg

Occupation: Founder of WordPress

Net worth: $400 million

Responsible for a company that at one time powered 22 percent of the web, Matt Mullenweg called his creation of WordPress “basically a big experiment.” He knew the path ahead wasn’t always clear or straightforward.

In an interview with Mapping the Journey, Mullenweg explained how he transformed an open-source project into a platform used by millions of developers around the world, noting that the adaption was gradual — nothing happened overnight. Essentially, it was a waiting game to find the tipping point.

“The biggest challenge that we’re running into,” Mullenweg said, “is that people who are very comfortable or attached to the way that things currently work, can sometimes be scared of changes.”

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This article originally appeared on GOBankingRates.com: The Rich and Famous Reveal Their Struggles at Work — and in Life