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Jessica Simpson and 25 More Celebs Who Got Richer From Their Second Jobs

Charles Sykes/Invision/AP / Shutterstock.com

Charles Sykes/Invision/AP / Shutterstock.com

Jessica Simpson transitioned from pop princess to business mogul with the launch of the Jessica Simpson Collection, a fashion and accessories brand that was bringing in $1 billion in annual sales as early as 2014 — enough that she never has to sing another note again.

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Simpson made her side hustle pay as much or more than her first career, which was hardly too shabby on its own — and she’s not alone. These 26 stars transitioned from actors to singers, models to moguls and rappers to fashion designers to add millions to their net worths.

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Jessica Alba

  • Net worth: $100 million
  • Her first career: Actress
  • Her second career: Household goods entrepreneur

Jessica Alba’s acting career brought her fame, but she gained fortune as co-founder of The Honest Company, which sells non-toxic household goods. The Honest Company enjoyed incredible success as a private company before going public in May. It raised nearly $413 million through its IPO.

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Tyra Banks

  • Net worth: $90 million
  • Her first career: Supermodel
  • Her second career: Media mogul

Although she started as a model, Tyra Banks built her empire as a media mogul, at one point producing and appearing in her own namesake daytime talk show as well as “America’s Next Top Model.” More recently, she served as star and executive producer of the TV movie “Life-Size 2” and worked as the host of “Dancing With the Stars.” She’s also cofound an ice cream brand called “SmizeCream.”

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Sean ‘Diddy’ Combs

  • Net worth: $900 million
  • His first career: Rapper
  • His second career: Liquor entrepreneur

You might know him as Puff Daddy, P. Diddy, Diddy, or Sean Combs, but no matter what you call him, there’s no denying that this rapper-turned-entrepreneur has become a serious mogul in the beverage space. The main contributor to Combs’ fortune — he earned $55 million in 2020 — is his vodka brand, Ciroc, Forbes reported. He also owns DeLeon tequila and Aquahydrate alkaline water.

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Victoria Beckham

  • Net worth: $450 million
  • Her first career: Pop star
  • Her second career: Fashion designer

Formerly known as Posh Spice, Victoria Beckham has left her pop star days behind to focus on her fashion empire. The one-time Spice Girl is now the founder and creative director of Victoria Beckham Ltd., a fashion brand that includes ready-to-wear dresses, handbags, shoes, eyewear and more.

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Lauren Conrad

  • Net worth: $40 million
  • Her first career: Reality star
  • Her second career: Fashion designer

Lauren Conrad rose to stardom in high school as the star of the reality show “Laguna Beach: The Real Orange County.” She went on to star in its spin-off, “The Hills,” and in 2009, she launched her fashion and accessories line for Kohl’s, called LC Lauren Conrad. She has also dabbled in real estate and penned several books, including The New York Times bestseller “L.A. Candy.” In 2020, she launched Lauren Conrad Beauty, a cosmetics line made from vegan, ethically sourced ingredients.

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Drake

  • Net worth: $250 million
  • His first career: Actor
  • His second career: Rapper

Before he was a rapper and hip-hop superstar known as Drake, Aubrey Graham starred on the popular Canadian TV series “Degrassi: The Next Generation” from 2001 to 2009. He released his first mixtape, “So Far Gone,” the year the series ended and landed his first No. 1 hit in 2010 when he teamed up with Rihanna for the song “What’s My Name?” He has since had several successful singles and albums, including “Views” and “Scorpion.” Drake released his sixth album, “Certified Lover Boy,” in September 2021.

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Ellen DeGeneres

  • Net worth: $500 million
  • Her first career: Standup comedian
  • Her second career: Television personality

Ellen DeGeneres began her career as a standup comic and reached new levels of fame when she starred in her own sitcom, “Ellen,” in the ’90s. Her star rose even higher when she became a talk show host for the self-titled “The Ellen DeGeneres Show.”

That said, DeGeneres recently came under fire from both former staff members and celebrity guests claiming the show was a toxic environment and that DeGeneres was not as nice as she appeared on television. As more and more stories began to emerge, Ellen offered a lukewarm apology, but it wasn’t enough. In May, she announced that she would be ending her show in 2022 after 19 seasons.

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Rihanna

  • Net worth: $1.7 billion
  • Her first career: Singer
  • Her second career: Cosmetics entrepreneur

Barbados native Rihanna made a name for herself as a pop star and has parlayed that fame into a lucrative entrepreneurial career. Her Fenty Beauty makeup line, which she co-owns with luxury goods group LVMH, made an estimated $570 million in revenue in 2018, Forbes reported. Fenty did $100 million in sales in its first 40 days alone, according to Vogue, and Forbes reported this February that the company had reached $1 billion in valuation. Rihanna also co-owns a Fenty fashion line and Savage X Fenty lingerie line.

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Dwayne ‘The Rock’ Johnson

  • Net worth: $800 million
  • His first career: Wrestler
  • His second career: Actor

Dwayne “The Rock” Johnson started his career in the pro wrestling ring but successfully made a transition to the big screen. He has since become a perennial contender for the title of the highest-paid actor in the world, which he was yet again in 2020 when he pulled in $87.5 million in a single year. He now commands $20 million per movie.

The Rock is also quite the entrepreneur. He founded small-batch liquor company Teremana Tequila, co-founded production company Seven Bucks Productions and, most recently, purchased the XFL with plans to bring it back in 2022.

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Kylie Jenner

  • Net worth: $700 million
  • Her first career: Reality star
  • Her second career: Cosmetics entrepreneur

Kylie Jenner grew up before America’s eyes on “Keeping Up With the Kardashians,” and at 21 years old, she was dubbed the youngest “self-made billionaire” by Forbes, due in large part to her Kylie Cosmetics line. Though the publication has since retracted that announcement, claiming that Jenner’s people purposely misled Forbes, the influencer is still worth an impressive $700 million.

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Selena Gomez

  • Net worth: $75 million
  • Her first career: Actress
  • Her second career: Singer

Before she was a pop star, Selena Gomez was a Disney star. She appeared on the TV show “Wizards of Waverly Place” from 2007 to 2012. Gomez released her first album as the lead singer of “Selena Gomez & The Scene” in 2009  and released her first album as a solo artist in 2013. Her success as a musician landed her on Forbes’ 30 Under 30 list in 2016. More recently, she released a swimwear collection summer 2021.

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Ron Howard

  • Net worth: $200 million
  • His first career: Actor
  • His second career: Director

Ron Howard is best known these days for his directing work as the acclaimed filmmaker behind “Frost/Nixon,” “A Beautiful Mind,” “Apollo 13” and more. But he got his start as a child actor with roles in a number of TV series, including “The Andy Griffith Show,” where he played Opie Taylor from 1960 to 1968. Howard also starred in the popular 1970s series “Happy Days” as well as the hit movie “American Graffiti” in 1973.

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Jessica Simpson

  • Net worth: $200 million
  • Her first career: Singer
  • Her second career: Lifestyle entrepreneur

The early 2000s saw Jessica Simpson rise to fame as a pop princess, then a reality star. In 2005, she officially added “business mogul” to her resume with the launch of her lifestyle brand, the Jessica Simpson Collection. Simpson sold a majority stake in the company in 2015, which was bringing in $1 billion in annual retail sales at the time, Forbes reported.

In 2020, Simpson debuted a memoir entitled “Open Book” that reached No. 1 on the New York Times best-seller list.

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Miley Cyrus

  • Net worth: $160 million
  • Her first career: Actress
  • Her second career: Singer

Miley Cyrus got her start on Disney’s “Hannah Montana,” which paved the way for her to become a pop star herself after playing one on TV for years. Music is now her main source of wealth, according to Forbes. Three of her albums as a solo artist have been certified platinum by the Recording Industry Association of America.

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Dr. Dre

  • Net worth: $500 million
  • His first career: Rapper
  • His second career: Electronics entrepreneur

Dr. Dre has had a prolific career in hip-hop as a rapper and producer — and he still brings in money thanks to his extensive back catalog — but his headphone company, Beats By Dr. Dre, moved him into a much higher income bracket. Apple acquired the company for $3 billion in 2014. Forbes estimates that Dr. Dre took home a little over $500 million from that deal, which helped him secure the title of the highest-earning musician of the 2010s.

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Ariana Grande

  • Net worth: $200 million
  • Her first career: Actress
  • Her second career: Singer

As with Gomez, Ariana Grande got her start on Disney. She starred on the TV show “Victorious” from 2010 to 2013 and its spin-off show “Sam & Cat” from 2013 to 2014. She released her first album, “Yours Truly,” in 2013 and went on to release two No. 1 albums within the span of six months: 2018’s “Sweetener” and 2019’s “thank u, next.” Her Sweetener World Tour grossed over $1 million per stop, Forbes reported. In July, she paid some of her fortune forward by partnering with Better Help to give away $1 million in free therapy.

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Jay-Z

  • Net worth: $1.3 billion
  • His first career: Rapper
  • His second career: Liquor entrepreneur and investor

Jay-Z released his debut album in 1996 and has released 14 No. 1 albums since then — second only to the Beatles. Though he continues to bring in big money through his music and touring, his business empire and investments are most of the reason his net worth grew by 40% in just two weeks, as reported by Forbes in March, when Jay-Z showed off his business prowess with a flurry of rapid-fire deals.

First, he sold a majority stake in his streaming company Tidal for $297 million, a deal that Forbes estimates netted him $149 million in stock and cash. Just one week earlier, he sold Armand de Brignac, his luxury Champagne brand, to LVMH in a deal that valued the company at $640 million.

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Kim Kardashian

  • Net worth: $1.4 billion
  • Her first career: Reality star
  • Her second career: Cosmetics entrepreneur

Kim Kardashian West is a household name after years of “Keeping Up With the Kardashians,” but her reality show paychecks haven’t brought her the most wealth. Most of her fortune comes from her cosmetics line, KKW Beauty, which was valued at $1 billion in 2020. The pop culture icon sold a 20% stake of the company in June of that year, bumping up her net worth significantly.

That signaled the start of a yearlong legal battle over licensing with KKW that ended with a California appeals court affirming an $11.5 million judgment in the Kardashian sisters’ favor. Almost immediately, Kim Kardashian announced she was temporarily closing KKW and starting a new brand altogether.

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Michael Strahan

  • Net worth: $65 million
  • His first career: Professional football player
  • His second career: TV host

As a star for the New York Giants from 1993 to 2008, Michael Strahan’s career earnings from his time with the NFL totaled $76.8 million, according to Over the Cap. While that’s no chump change, Strahan is now earning a $20 million annual salary as a host of “Good Morning America,” People reported. He is also a football analyst on “Fox NFL Sunday.”

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Heidi Klum

  • Net worth: $160 million
  • Her first career: Supermodel
  • Her second career: Business mogul

Supermodel Heidi Klum has made millions off the runway thanks to her lucrative business deals and television endeavors. She inked a deal with New Balance for a collaborative collection and also starred in several TV shows, including “Project Runway” and “Seriously Funny Kids.” Klum currently appears as a judge on “Germany’s Next Top Model” and “America’s Got Talent,” and has her own line of lingerie, Heidi Klum Intimates.

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Mark Wahlberg

  • Net worth: $350 million
  • His first career: Rapper
  • His second career: Actor

Mark Wahlberg first rose to fame as rapper Marky Mark. Although his musical career made him a teen idol, his acting has really produced the big bucks. Just like The Rock, Wahlberg pulls in eight-figure checks per project and is at or near the top of the highest-paid list year after year. He earned $58 million in 2020, making him that year’s No. 33 top-earning celebrity of any stripe, according to Forbes.

The rapper-turned-actor also co-owns a burger chain called Wahlburgers with his brothers Paul and Donnie. The siblings had a reality show about their line of restaurants from 2014 to 2019.

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Jennifer Lopez

  • Net worth: $400 million
  • Her first career: Actress
  • Her second career: Singer

Jennifer Lopez got her big break when she starred in the movie “Selena” back in 1997. Two years later, she released her first single, “If You Had My Love,” and successfully transitioned from “actress” to “singer-slash-actress.” Now, singing might be her biggest moneymaker. J-Lo earned a whopping $100 million over her two-year Vegas residency alone, according to Forbes.

She’s produced several TV series over the last few years and is currently working on five upcoming film projects.

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Demi Lovato

  • Net worth: $40 million
  • Her first career: Actress
  • Her second career: Singer

Demi Lovato first gained fame as the star of the 2008 Disney Channel movie “Camp Rock.” Her first album, “Don’t Forget,” debuted at No. 2 on the Billboard 200 chart that same year and Lovato has been churning out the hits ever since.

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Kanye West

  • Net worth: $1.8 billion-$6.6 billion
  • His first career: Rapper
  • His second career: Fashion designer

Rapper Kanye West has built up a music catalog worth $80 million, however, nowadays he makes most of his money from his Yeezy apparel line and sneaker partnership with Adidas. The Yeezy brand is valued at about $4-$5 billion, according to Celebrity Net Worth.

In a bizarre twist of events, Bloomberg listed Kanye’s net worth at $6.6 billion, which would have made him the wealthiest African-American of any gender in U.S. history. Forbes quickly called shenanigans and did its own evaluation. The results estimated the controversial celebrity’s net fortune to be more like $1.8 billion.

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Reese Witherspoon

  • Net worth: $300 million
  • Her first career: Actress
  • Her second career: Entertainment mogul

Reese Witherspoon struggled to find strong roles as an actress earlier in the decade, so she took it upon herself to create them. Witherspoon founded the production company Pacific Standard in 2012, which produced the films “Gone Girl” and “Wild.” In 2016, Witherspoon partnered with Otter Media to launch Hello Sunshine, which now operates a book club, audio programming with Audible, multiple podcasts and an Apple TV+ collaboration. In July, it was announced that Apple was considering buying Hello Sunshine for $1 billion.

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Rachel Zoe

  • Net worth: $30 million
  • Her first career: Celebrity stylist
  • Her second career: Fashion entrepreneur

Rachel Zoe started her career as a stylist to the stars and arguably became as famous as her clients when she starred on the reality show “The Rachel Zoe Project.” Since gaining reality fame, Zoe has launched a number of business ventures, including her upscale fashion line, the Rachel Zoe Collection, and her subscription service, The Zoe Report Box of Style.

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Andrew Lisa contributed to the reporting of this article.

Disclaimer: Unless otherwise noted, all net worths were sourced from Celebrity Net Worth and are up to date as of Dec. 15, 2021.