Iggy Azalea: How Powerful Older Men Become The Reason For A Woman’s Lack Of Success – And How A Woman Starting Her Own Venture Becomes The Hardest, And Yet Most Rewarding, Step In Her Career

The latest two subject matters that were Demi Lovato have more than just being involved with Scooter Braun formerly managing their careers in common. They also both collaborated with Iggy Azalea in the 2010’s. Azalea was featured in Lovato’s ‘Kingdom Come’ from her 2015 album, ‘Confident’, and Grande’s ‘Problem’ from Grande’s 2014 album, ‘My Everything’. She simultaneously released her hit lead single, ‘Fancy’, featuring Charli XCX. It broke barriers! The year 2014 was Iggy’s year. It was a once-in-a-lifetime experience for her as she never amounted to that amount of success thereafter.

Azalea’s career had never been the same following her massive 2014 debut. In fact, I’d say it’s pretty safe to say that her career had failed in the past decade. There are more reasons for it than just an unsupportive management and record label. These include:

• Personal drama – Azalea’s public breakup with her basketball player fiancé, Nick Young, was ugly following his cheating scandal. She claimed she caught him cheating and torched his clothes in her fire pit. 
• Mental health struggles – Azalea granted several interviews in early 2016 about the mental health struggles she’d been faced with since her rise to fame. 
• Delayed album – Azalea’s second album, Digital Distortion, was delayed due to her personal drama. She teased its release in 2016, but by November 2017, it was still nowhere to be found. 
• Canceled tours – Azalea’s two headlining tours were canceled in 2015 and 2018, which means she never got to headline, though she was an opening act for Rita Ora, Beyoncé, Tyra, and more.
• Forbes headline – Forbes declared in one of their articles that “Hip Hop Is Run By A White, Blonde, Australian Woman”. 
• Halsey’s barb – In a 2017 interview with The Guardian, singer Halsey made a stinging barb at Azalea. 
• T.I.’s comments – T.I. suggested that Azalea had become an easy target for mockery and derision.
• Drama with her baby daddy – Azalea had a child in 2020 with Playboi Carti after a brief relationship. She’d previously publicly shamed him for not being there for their son and showing off as if he was on social media for public displays. In July 2024, Azalea claimed herself to be her son’s only parent, and said that her ex refused to be named in the birth certificate.

But on top of having a personal beef and drama with former boyfriends, former fiancé, and baby daddy, Azalea found herself beefing with her peers in the industry. When Azalea was nominated for a Grammy in December 2014, Azealia Banks certainly had a few words to say. In an interview on Hot97, she said, ‘When they give these Grammys out, all it says to white kids is: ‘Oh yeah, you’re great, you’re amazing, you can do whatever you put your mind to. And it says to black kids: ‘You don’t have s**t.’ And you can be sure that Azalea didn’t take it very well. She later tweeted, ‘Special msg for banks: There are many black artists succeeding in all genres. The reason you haven’t is because of your piss poor attitude.’ T.I defended Banks and gave Azalea a history of hip-hop and its origins on Twitter, now known as X, directed at her.

Azalea and Banks eventually reconciled, and they even made plans to collaborate together on Azalea’s second album, ‘Digital Distortion’. The album was eventually scrapped and the much anticipated collaboration never happened. Azalea wasn’t able to recover her public image following the feud. In 2015, she planned to go on tour as a headliner, but had to cancel following poor ticket sales. Some venues reported that just 20 percent of tickets sold. Those reports were later denied, however, by concert promoter AEG Live. That same year, Azalea was featured in Britney Spears’ song, ‘Pretty Girls’. It…BOMBED. It was a huge blow for the newcomer, and she didn’t take it well. Yet again, the rapper took to Twitter to play victim. She wrote, ‘its [sic] difficult to send a song up the charts without additional promo and tv performances etc. unfortunately im [sic] just featured…’. When Spears’ fans didn’t take the tweet too well, Azalea took matters to her own hands and tweeted, ‘my comment is factual, it applies to any song. I dont [sic] have to suck the womans [sic] a**hole 24/7 to be her friend, do i? bye girls.’ Spears later made her tweet and wrote, ‘Can’t wait to get back to Vegas. So thankful I have shows for the rest of the year to look forward to… #YouWantAPieceOfMe.” Game. Set. Spears.’

What followed was Azalea releasing singles for her sophomore album such as ‘Saviour’, featuring Quavo, ‘Trouble’, featuring Jennifer Hudson, as well as ‘Team’. Her solo single particularly, failed to top the charts. It peaked at number 42 on Billboard Hot 100. A year later, the rapper scrapped the project altogether and instead released a six-song EP with a completely different title to it. By that point, T.I, who signed Azalea in 2012 and was behind the release of Azalea’s debut album, ‘The New Classic’, and making it a success, admitted that his professional relationship with the rapper was complicated. He told XXL in 2017, ‘She’s doing as good as Iggy do. One thing I learned, man, is not to put no time on what she’s trying to do. … I’m not trying to rush her plans to suit mine.’

Once she left T.I’s record label, she joined Island Records, but only ended up being their artist for less than a year. Further disagreements led Azalea to leave Island Records record label for good and start her own. Through a distribution partnership with Emire, she started Big Dreams. In her 2018 announcement, she said, ‘I’m so excited to begin a new entrepreneurial chapter in my career with EMPIRE as my partner. The ability to have control of my own artistic future is a long awaited and monumental change in my life. I genuinely feel I am in the best position to achieve my creative ambitions.’ Then on Twitter, she wrote, ‘Proud to say I literally just signed my new deal/partnership! 2.7mil, can sign others, own my masters + 100% independent – I’m feeling like such a bossy grown ass bitch today!  Time to get back to ME. I’m so grateful & excited…’

Through her own record label, Azalea released two albums and an EP. The first album was 2019’s ‘In My Defense’, and the second was ‘2021’s ‘The End of an Era’. She released music videos for songs such as ‘Started’, ‘F*ck It Up’ featuring Kash Doll’, ‘Sally Walker’, and most recently, ‘Money Come’. I personally loved the music videos that Azalea made for herself. They had a different feel to them. They seemed more real, more intimate, more creatively vibrant. They were made with care and love rather than with a careless budget. It was obvious that they were made by a woman. There was a time where I couldn’t get enough of watching these newer music videos on YouTube. I’d say my favourite to watch was ‘F*Ck It Up’. The dialogue in it was also hilarious.

The public didn’t agree, though. The music she made for herself didn’t amount to much success, but she didn’t care because she wasn’t doing it for others, rather for her own damn self. By January 2024, Azalea announced her retirement from music. In a lengthy statement posted on X, she wrote, ‘I’ve always been someone who finds my joy in being creative & seeing my ideas come to life. For a long time I used music to deliver my big crazy ideas to the world,” she wrote. “I know a lot of people have this idea that I was ‘bullied away from music’ and that’s something I’ve always laughed at because I’d never be bullied out of anything! In fact, I’m too stubborn. I think I’ve even resisted changes within myself at times, purely because I don’t like being viewed as someone who quits. In truth what I’ve known for a long time is that I feel more passionately about design and creative direction than I do about songwriting,” she continued. “That’s why I want to let you know that I’m not going to finish my album. It’s been paused for a few months while I was giving direction for a different project & in truth I just haven’t felt the urge to go back to it. I feel really happy & passionate in my day to day life when my [mind’s] focused on that and so I want to stick to what’s undeniably best for me.’

When I initially started writing this blog entry on Iggy Azalea, I had the idea of writing about how her career as a music artist failed. Moreover, I was going to give reason that her persona, social media presence, and inability to shut up were the reasons for her career downfall. Getting into a public spat with someone like Britney Spears is NEVER a good idea. Getting into a public social media with your boss and your boss publicly defending someone that you’re beefing with is also not a good idea. Oprah once said, ‘Think like a queen. A queen is not afraid to fail. Failure is another stepping stone to greatness.’ Over the years, there have been other women who’d failed to make it in the music industry. These include Kesha, JoJo, Victoria Justice, who starred alongside Ariana Grande in ‘Victorious’, and even Zendaya, who’s literally killing it right now with her massive success – both in her career and her personal life.

Like Azalea, Kesha, previously known as Ke$ha, found instant massive success in 2010 with her hit single, ‘TikTok’. Unlike Azalea, Kesha never found herself beefing or feuding with anyone on social media. This was before social media was ever as massive as it is now or even in mid 2010’s. Her career downfall wasn’t of her own doings by any means. In between her ‘Warriors’ and ‘Rainbow’ albums, Kesha was involved in a legal battle with Dr. Luke, who managed her career. The battle began in 2014. There were 3 key takeaways from the battle:

• Creative control: Kesha had little creative control over her album Warrior, and some songs she wrote were removed against her wishes. 
• Fan petition: In 2013, a fan petition with over 10,000 signatures called for Kesha to be “freed” from Dr. Luke’s management. 
• Concert banners: Fans at one of Kesha’s concerts carried banners that read “F**k Dr. Luke”.

In 2016, a New York State judge rejected Kesha’s claims against Dr. Luke. The judge ruled that Kesha didn’t have enough evidence to prove her allegations to be truthful. In fact, the opposite. The judge also ruled that her claims did not constitute a hate crime. The legal battle was finally settled in June 2023. Kesha continued doing music, yet she never found as much success as she did when she started her career. The success she found with at the very start was a once-in-lifetime event for her, just like it was for Azalea. In 2017, Kesha released ‘Praying’, a song which was alluded to be about Dr. Luke. She then also released singles such as ‘Rainbow’ ‘Learn To Let Go’, and ‘Hymn’. And just like I did in Azalea’s case, I loved her music videos post her public battles with Dr. Luke than I did for her music beforehand. They told her story. They told her truth. It’s more than I could ever say about her music and promotional videos when she was under Dr. Luke’s management.

Unlike Azalea, Kesha never retired from music. She still continues to make art despite not ever finding the same amount of success as she did before. Like Azalea, however, she started her own record label. In an interview with Elle magazine published last October, Kesha said, ‘I’m about to make some major moves and shift this sh*t. I really want to dismantle it piece by piece and shine light into every corner. I hope my legacy is making sure it never happens to anybody ever again. I don’t believe in ownership in perpetuity of anyone, anything, on any level, in any business. That should not be something a human being can commit to. I feel like people want to own a beautiful thing. And it sucks for them, but you just can’t! We live in a time that’s more democratic. People can share whatever they want on all these different platforms. I’m excited to see what that means for the future of music – what the future of the world sounds like. When I was coming up, I wished there was some woman in pop music that I could have reached out to and talked to about stuff I was going through. I found more support from the rock boys – Foo Fighters, Dave Grohl, Pat Smear and Alice Cooper were very real, and helped me talk through things. So now I try to reach out to artists, girls and women, and just offer my services of life experience. I don’t believe you can create if you’re not feeling safe. The old guard, they’re falling. The old way of doing everything with secrecy – there’s no future there. So, like, those of you with deep, dark secrets, you better fucking run.’

This leads me to now talk about JoJo. She had a very similar story to Kesha’s. And yet, she was only 12 years old when her debut single, ‘Leave (Get Out)’ first came out in 2004. It was a jam, I’m not even going to lie. In an interview with Grazia published in September of last year, JoJo reflected on early start in fame, ‘I started putting out music so young. I wanted to try to make sense of what the past 20 years of my life and career have been and share some of the stories, the hard times, the weird times and the things that I’ve learned along the way. My mum was really just trying to make her daughter happy by letting me pursue this thing with my gifts and it was a tough time for her, and for me, but simultaneously the most exciting time – and exactly what I wanted. I think it’s very normal when somebody starts out super young for other people to be in the driver’s seat. It’s not something that I felt was wrong at the time, but I just never learned how to really take the wheel. Then I filed a lawsuit, and I was caught up in that for a long time, many years, and then the lawsuit ended. I didn’t even ask for money, I just wanted to be able to move forward. That period was like industry musical chairs, a lot of politics behind the scenes, people leaving labels and me not having an advocate at that particular label, boring industry stuff, but unfortunately that’s my story. I was deeply, deeply confused and I felt really shovelled around. I was angry. I was making so much music and fans were like “why aren’t you putting anything out?” I felt embarrassment and shame in ways that I had learned from childhood – numbing the pain with substances and feeling like I was doing a really good job of holding on.’

After a hefty legal battle, JoJo was finally able to re-release her first two albums under her own record label years later the day after she turned 28. Keep in mind, she started her career as an artist when she was 12. The rest of the albums she’s released have been made by her own entrepreneurial venture. None of which garnered the same success that she experienced when she first started out, but her freedom was worth a lot more than that. Through the in-between, JoJo also starred in a few movies, including 2006’s ‘Aquamarine’ with Emma Robert’s and Sara Paxton, as well as 2006’s ‘RV’ with the late Robin Williams, Jeff Daniels, and Cheryl Hines. For the most part, however, JoJo mainly concentrated on her career as a performing artist. Her 2016 single, ‘Save My Soul’ was about her dad, and it was directed by Zelda Williams, Robin Williams’ daughter.

If you’re a fan of Zendaya like I am, you will know that this is practically HER year to shine – both in her personal life and career. While walking the red carpet at the Golden Globes, the actress showed off her new engagement ring, which confirmed that she was engaged to her longtime boyfriend, Tom Holland. In a recent interview with Men’s Health, the actor recently revealed why the couple never walk on any red carpets together. He said, ‘because it’s not my moment, it’s her moment, and if we go together, it’s about us.’ He also opened up more about his private life with Zendaya and his plans for the future. He said, ‘When I have kids, you will not see me in movies anymore. [It’ll just be] golf and dad. And I will just disappear off the face of the earth.’ It’s a testament that Zendaya seemed to be in agreement with for her own career path, saying she wasn’t sure whether she wanted to continue working or not once she had kids. I personally hope she doesn’t. She’s SO good! She’s worked in the entertainment industry for more than two decades, and she’s not even 30 year. Most recently, Zendaya’s work included ‘Challengers’ and ‘Dune: Part 2’, and thus far, she’s not stopping there. She has the fourth ‘Spider Man’ instalment in the works, as well as the third season of her hit series, ‘Euphoria’.

When we think of Zendaya, we think of her as an actress. We tend to forget that she once used to be a singer. She even released an album in 2013, and even had plans to release a second album, though it never saw the light of day. In 2022, while discussing why she chose to step away from music and touring on Variety’s ‘Actors On Actors’ with Andrew Garfield, Zendaya said, ‘I was talking to Sam [Levinson, Euphoria director] about it earlier. I was like, I don’t know if I could be a pop star. It’s because as an actress, there’s a level of anonymity that I get to have, which I really enjoy. And I can sort my stuff, whatever it is, through a character, and nobody needs to know about it. Whereas in other ways and other means, it’s all you all the time. I like the idea that someone else, namely Rue, can take on these things. I walked away from music a long time ago, for various reasons.’ Garfield even asked if limits could be a reason for her uncertainty about returning to the music industry, Zendaya said, ‘Yes, limits. Learning what it is to me.’

In April 2024, Zendaya appeared on ‘The Jennifer Hudson Show’, where she further spoke about what led her to step away from the music industry. She said, ‘It (being in the music industry) didn’t kill the joy of music, but it’s when you put music and business together sometimes, it’s, it can not feel so good. So, you know, I think if the right timing and it came to – ’cause I like creating it, like again, for myself, but if there was a moment maybe I would, you know, put out a little something.’ Zendaya never truly stepped away from music following the release of her sole 2013 album. In 2016, she released ‘Something New’, a single which featured Chris Brown. Then in 2017, she starred in ‘The Greatest Showman’ with Hugh Jackman and Zac Eaton where she showcased her skills as a singer and dancer.

I wasn’t initially going to include this in this particular blog entry, but Zendaya’s take on the music industry reminded me so much of that of Lauren Jauregui’s. She was 1/5 of the mega hit girl group, Fifth Harmony, who competed on ‘The X Factor US’ in 2012. After hitting an enormous amount of success over the years, the girls went on an indefinite hiatus in 2018. In 2021, Jauregui appeared on ‘The Zach Sang Show’, where she opened up about the experience of being part of Fifth Harmony. She said, ‘I think that’s the path that we’re on right now. Because a lot of what happened to us wasn’t even us. It was all of the pieces around us. We were young adolescents thrown into the spotlight. Because remember, ‘X Factor’ is not even anything but a reality show that you’re on TV in front of millions off the bat, and I think we all just had our own way of processing that. And that affected the group in general. And that affected us personally. And I think that now we’re at a point in our lives where we’re healing from it, and we’re each doing what we were truly meant to do for ourselves. So many adults taking advantage of that naïveté. It’s abusive.’ In a leaked audio, Jauregui was heard saying that she and the rest of the group members were treated like slaves. Lawyer Dina LaPolt said that the group’s original contract was the worst she’d ever seen. She previously told Billboard, ‘I sat the girls in a hotel conference room and for five hours educated them on trademarks, copyrights and rights of publicity. Then I educated them about every agreement they signed, which [were] the worst I’ve ever seen in the music business.’

All former members of Fifth Harmony have since moved on with their own respective solo careers. Camila Cabello, who left the group in 2016, has found the most success. Jauregui, on the other hand, never found much success in the music industry following her time in Fifth Harmony. She’s released music here and there through her own record label, but if I’m being completely honest, it’s kind of…boring. It’s not mainstream and there’s not much depth to it. It’s like she doesn’t put much effort into it. In a 2023 interview with Uproxx, the singer opened up about her new career move as a solo artist and a businesswoman. She said, ‘I’ve learned a lot about being a businesswoman and about this industry in general and how it works. I’ve had my failures and I’ve had my mistakes made. I was really young when I got into the industry. I didn’t really have a lot of mentors or people who guided me on how to move. So, I’ve made a lot of mistakes. But I feel like I’m so grounded right now, and I have such a great team around me who really sees me and is mentoring me and guiding me in ways that I trust and allow me to relax into my creativity. All I ever really wanted was to be able to create from an authentic place and that’s a lot more difficult than it should be, I think. But I feel like I’ve gotten to a point now that I’m independent and I have full creative control, and I’m able to really move in ways that align with my spirit, and that’s all I’ve ever wanted.’

Sometimes, though, a woman’s lack of success isn’t necessarily at the hands of the people around her. Victoria Justice is another artist who’d failed to make it big. Unlike the women on the list before her, her lack of success following her time at Nickelodeon wasn’t caused by the powerful men that surrounded her. Her years at Nickelodeon were her prime. Following her exit from the company, Justice didn’t find much success in the music industry, nor did she find much of a success in acting. The reasons behind her lack of success include:

• Lack of individuality – some say that Justice didn’t show much individuality as an artist, and people still see her as the character she played on ‘Victorious’. 
• Record label split – after signing with Columbia Records, Justice’s debut single sold only 33,000 copies. She split from the label a few years later. 
• Hate train – some say that Justice was going through a hate train when she released her debut single. 
• Need for Nickelodeon machine – some say that Justice couldn’t do well without the support of Nickelodeon.

What we can take away from all these women on the list is that a lack of success in one career path that was caused by the people around who are much powerful than you shouldn’t stop you from continuing on to pursue other aspirations. In many cases, taking the entrepreneurial position such downfall a much more difficult, and yet rewarding step in a woman’s career. Though it’s possible that you won’t find a level of success you found at the hands of powerful men, your freedom is worth more than any kind of level of success. It doesn’t just have to be in the entertainment industry, but in regular life as well.

What Iggy Azalea’s career path has shown us is that sometimes it’s okay to choose – choose to let go of something you used to love, but now you know isn’t for you. Since retiring from music, she also quit OnlyFans, which earned her millions. In June 2024, the former rapper announced a new $200 million crypto venture and phone company – Mother Iggy – inspired by a meme that she came across. She shared with Forbes, ‘I’m someone that naturally has had so many memes over the course of my career; things go viral on purpose or accidentally. I felt like it was a space I could really engage with in a successful way.’ Then she added on X, ‘They used to laugh at me rapping and I got a number 1 single for 9 weeks straight. I could bet I know where this is headed… Laugh now, cry later I’m certain.’

I find that, in my own career path, the entrepreneurial journey has the hardest, and yet most rewarding one of all. It’s already hard to prove yourself in this day and age as a woman. Being a disabled woman is a completely different altitude of its own. My own journey hasn’t been easy. I got involved in entrepreneurship because the job market wasn’t kind to me. I was inherently because of my cerebral palsy. When recruiters saw that I had a disability as soon as they saw me, they strictly saw me for my disability rather than anything else that I could potentially bring to their company. They made assumptions about me that simply weren’t true, such as that I wasn’t able to type on a computer. If you’re reading this right now, how do you think all the blog entries you see here have been typed up?

No one believed in me, so I started believing in my own damn self. I started my freelancing business in 2016. Slowly but surely, I started getting clients left and right. People wanted to work with me BECAUSE of my story; because I broke down barriers. I felt so fortunate to have worked with all my clients, no matter how big or how small the projects were. With that said, there are several things you should know about what it takes to be a female disabled entrepreneur:

• Underrepresentation – People with disabilities are underrepresented in entrepreneurship, with only 0.5% of small or medium-sized businesses in Canada owned by a person with a disability. 
• Barriers – Women with disabilities face high barriers to entrepreneurship. 
• Success rate – When supported, people with disabilities have a 65% success rate in self-employment and entrepreneurship. 
• Diverse perspectives – Entrepreneurs with disabilities can bring diverse perspectives, skills, problems, and ideas into startups.

Now I have this blog, and I feel even more fortunate that people are interested and invested in my stories and everything that I have to say. It’s a truly rewarding experience. Being a writer, no matter in what capacity, feeds my soul. It gives me a level of freedom that I never experienced. And maybe I would’ve been much more successful had I’d gotten the opportunity back then to work under a powerful man back then, but I know that if I had, I wouldn’t have truly gotten to know just how skilled, capable and powerful I really am.