MONEY Entrepreneurs

13 Hip-Hop Artists Who Make Millions as Successful Entrepreneurs

These rappers know how to get paid.

Jamie Trueblood—Universal Pictures/courtesy Ever “Straight Outta Compton,” produced by rap titans Dr. Dre and Ice Cube, has been the #1 movie at the box office for two weeks.

“Straight Outta Compton,” which earned $60 million at the box office during its opening weekend, was America’s #1 movie yet again this past weekend, making it one of the biggest-ever August releases. Made for $29 million, the biopic of gangsta rap group N.W.A. crossed the $100 million ticket sales mark less than 10 days after its debut.

Among other things, what this means is that the rap world can add “blockbuster movie producer” to the long list of successful entrepreneurial endeavors it has spawned. The movie was produced by Dr. Dre and Ice Cube, the leading creative members of N.W.A. Dre and Cube are not only legends in the rap game, they’re representative of the many hip-hop artists who have been phenomenally successful outside of music, launching fashion lines, restaurant chains, luxury electronics, and liquor and beverage brands.

At first glance, it may seem odd that so many rappers become entrepreneurs. But think about it: Rappers use carefully crafted words, style, swagger, and images to sell themselves to the masses. They’re experts at making “Something from Nothing,” as the title of the 2012 rap documentary by Ice-T put it, and the most successful rappers know their audience incredibly well. After working so hard to sell themselves and their music, many rappers find it fairly natural to cross over and market other products and lifestyle brands to fans. And no matter if we’re talking song lyrics or the creation of a luxury brand of headphones, artists with roots in rap have an uncanny ability to remain relentlessly focused on money and “getting paid.”

  • Dr. Dre

    Dr. Dre speaks onstage at WSJ. Magazine's "Innovator Of The Year" Awards at Museum of Modern Art on November 5, 2014 in New York City.
    Mike Coppola—Getty Images

    In addition to being a gangsta rap pioneer with N.W.A., Dr. Dre is also the visionary who produced and called the world’s attention to rap superstars like Snoop Dogg and Eminem. And he’s been a hugely successful artist on his own, starting with his multi-platinum solo debut album “The Chronic” and continuing with this summer’s “Compton: A Soundtrack,” which was streamed 25 million times during the first week it was available on Apple Music.

    Speaking of Apple, in 2014 the tech giant acquired Beats Music and Beats Electronics, the music subscription streaming service and maker of flagship $300 headphones founded by Dr. Dre and Jimmy Iovine, for $3 billion. Dre’s net worth hit around $800 million as a result—and that was before the release of “Straight Outta Compton.” The deal landed Dre on Entrepreneur magazine’s list of “10 Entrepreneurs Who Defined 2014.” Also on the list: fellow musician Beyoncé, whose roots are in R&B, not rap.

  • Kanye West

    Kanye West during London Fashion Week Fall/Winter 2015/16 on February 20, 2015 in London, England.
    Danny Martindale—WireImage/Getty Images

    Kanye West is no stranger to haters. At the start of his career as a producer-turned-hip-hop artist, he struggled to be taken seriously as a rapper given his middle-class background and an aesthetic that didn’t match the stereotypical industry apparel. Well into his fame, President Obama called West a “jackass” for his infamous “Imma let you finish” interruption of Taylor Swift’s acceptance speech at the 2009 VMAs. But haters have hardly gotten in the way of West amassing his $130 million fortune—as he rapped, borrowing from 50 Cent, in The Good Life: “If they hate then let ‘em hate and watch the money pile up.”

    Beyond being one of the best-selling and most award-winning artists of all time—he’s sold over 21 million copies of his just six albums, and won 21 Grammys—he’s also founded his own record label, G.O.O.D. Music, is a part owner of the Jay Z-owned streaming service Tidal, and has directed a number of short films. And as the New York Times has pointed out, his movement into the world of fashion—from collaborating with A.P.C., Adidas, and Louis Vuitton to launching a women’s clothing label, DW Kanye at the 2011 Paris Fashion Week—has “widened the genre’s gates… for high-fashion and high-art dreams.”

  • Ice-T

    Actor Ice-T during an interview with host Jimmy Fallon on July 30, 2015.
    Douglas Gorenstein—NBCU Photo Bank/Getty Images

    Known mostly today for his starring role in both the reality TV show “Ice Loves Coco” and the 15-year-running cop drama “Law & Order: SVU,” Ice-T first came to fame as a groundbreaking gangsta rapper with hot-selling tracks like “Colors.” But Ice-T has been many things beyond actor and rapper. Before making a living from rap, he was a pimp, thief, and all-around hustler. A partial list of his non-rap ventures once he became famous include creating and fronting a thrash metal band (Body Count), founding an online music label way back in the Napster era, launching a podcast, doing voices for multiple video games, serving as a producer for 18 TV shows and movies, co-authoring three books, and organizing this summer’s first-ever Art of Rap Festival—a concert series that takes its name from the Ice-T-directed 2012 documentary, “Something from Nothing: The Art of Rap.”

    It’s understandable, then, that the word most commonly associated with Ice-T is hustle. “New Jack Hustler” was one of Ice-T’s most popular songs—used in the 1991 movie he also starred in, “New Jack City”—but “hustle” has been part of vocabulary for a long time. In fact, instead of focusing on rap for its artistry and insights into urban culture, Ice-T has referred to it as just another way to get rich. “Rapping is a hustle to me,” Ice-T said on the VH1 documentary “Behind the Music.” “I’m not one of those guys that’s like, ‘Oh I love the music.’ Nah. I love money.”

  • Vanilla Ice

    Robert Van Winkle attends the Student Filmmakers showcase at the 2015 Palm Beach International Film Awards on March 12, 2015 in Boca Raton, Florida.
    Larry Marano—Getty Images

    It’s hard to say which is more improbable—that a middle-class white kid named Rob Van Winkle would turn into the rapper Vanilla Ice and have the first rap song to top the charts with “Ice Ice Baby”? Or that a decade after he’d had a hit song, he’d reinvent himself as a home-flipping construction guru on the DIY Network reality TV show “The Vanilla Ice Project.”

    As he told the New York Times in 2010, when the show debuted, Vanilla Ice unwittingly got his start in real estate by purchasing several homes when he was “young and dumb,” and at the height of his fame and riches. After spending barely any time in any of them, he decided to sell—and made several hundred thousand dollars in profit on each sale. He then took up the idea of “Hammer Time” more seriously, strategically buying lots and foreclosed homes in Florida, adding some value with smart improvements, and (hopefully) flipping them for easy money.

    It’s hardly an easy thing to do, though. “Fixer-uppers can be a dream or a nightmare,” he has said. “Expect the unexpected. You have to have carpenters and know how to budget projects. There are a lot of growing pains you’ll experience in your first few projects. But if you play it smart, you will find success.”

  • Nicki Minaj

    Nicki Minaj at the Marc Jacobs Fall/Winter 2015 Fashion Show at the Park Avenue Armory, New York City, February 19, 2015.
    David X Prutting—

    The reasons Nicki Minaj is everywhere—all over social media with 20 million followers on Twitter, inside Madame Tussauds in wax, and soon, even on her own mobile game app—are only partially due to rap. Throughout her career, Minaj hasn’t been focused simply on making music, but on building a brand.

    And she’s been able to extend her unique mix of attitude, sass, flash, smarts, and sex to her own personal brands of perfume and beauty products (sold at HSN), a women’s wear collection for Kmart, and a fizzy wine called MYX Fusions Muscato, among other ventures. In fact, her approach to business is often used as a paragon for how young people—women especially—should handle themselves in the workplace, including lessons on how to take charge at the office, how to rebrand yourself when switching careers or companies, and the necessity of being bold and assertive.

  • Ice Cube

    Actor Ice Cube visits 106 & Park at BET studio on January 16, 2014 in New York City.
    Bennett Raglin/BET—Getty Images

    What with the “Friday” films and family-friendly fare like “Are We There Yet?” Ice Cube’s career in movies has been arguably just as successful as his experience in rap, first as a member of N.W.A. and later as a solo artist. Both of Cube’s worlds collide in “Straight Outta Compton,” the highly profitable film released this summer that tells N.W.A’s story. Ice Cube not only served as a producer on the movie, his son O’Shea Jackson Jr., plays the role of his dad on screen.

    Ice Cube’s transition to film started while he was at the top of the rap game, in 1991, when he was cast as Dough Boy in the critically acclaimed “Boyz N the Hood.” (Ice Cube actually wrote a song with the same name a few years earlier.) He has also been in the director’s chair, for the 1998 film “The Players Club” and the ESPN documentary “Straight Outta L.A.,” about the period when the NFL’s Raiders were based in Los Angeles rather than Oakland.

  • 50 Cent

    Curtis Jackson, aka 50 Cent, in Manhattan on Tuesday, July 21, 2015.
    Joe Marino—NY Daily News/Getty Images

    Given he launched his music career with the nine-times-platinum album Get Rich or Die Tryin’, it’s perhaps no surprise that Curtis Jackson, better known as 50 Cent, has long been a hustler. He got his moneymaking start as a 12-year-old on the streets of Queens in the late ‘80s; by the age of 18, he was raking in $5,000 a day on crack and heroin sales. Jackson’s time as a dealer culminated with a 2000 shooting outside his grandmother’s home that left him with a hole in his jaw, a piece of bullet lodged in his tongue, and a new sound: as he told Rolling Stone for a 2003 cover, “Getting’ shot just totally fixed my instrument.”

    Since his rise to music fame as the protégé of Dr. Dre and Eminem in the early 2000s, Jackson’s business spirit hasn’t let up. In 2003, he founded his own record label and clothing company, both called G-Unit. A partnership with Vitamin Water soon after landed him a minority stake in the company, which he later sold and then rapped about in his 2007 song I Get Money: “I took quarter-water, sold it in bottles for two bucks. Coca-Cola came and bought it for billions. What the f***?” 50’s more recent ventures include a headphone competitor to Beats, a high-end vodka label, and patented support technology men’s underwear.

    It was no small blow when the loss of a high-profile lawsuit forced the rapper to file for bankruptcy in July, just two months after having ranked fourth on Forbes’ Hip Hop’s Five Wealthiest Artists 2015, with an estimated net worth of $155 million. But the Chapter 11 filing doesn’t mean 50 Cent is broke—just a little low on cash.

  • Jay Z

    Rapper Jay-Z acknowledges a fan in Los Angeles April 16, 2014.
    Kevork Djansezian—Reuters

    Though Jay Z—whose real name is Shawn Carter—has gone in and out of music retirement over the past decade and a half, his status as an entrepreneur and entertainment mogul hasn’t wavered much. In addition to having owned his own nightclub, vodka company, and fashion line, Rocawear—which he sold in 2007 for over $200 million—Carter has also owned a lucrative share of the New Jersey Nets, which he later sold for a 135% gain. And in 2008, Carter founded the entertainment company Roc Nation, which in 2013 came to include a sports agency, new territory for the mogul.

    Jay Z’s net worth now sits somewhere around $550 million, but his investments haven’t all exactly gone swimmingly: Tidal, a subscription-based music streaming service owned by media technology company Aspiro, which Jay Z acquired in March 2015, was served with a $50 million lawsuit this summer. The news has prompted “99 Problems” jokes galore.

  • Snoop Dogg

    Recording artist Snoop Dogg arrives at the iHeartRadio Music Awards held at the Shrine Auditorium on March 29, 2015 in Los Angeles, California.
    Christopher Polk/NBC—NBC via Getty Images

    Hardly ever known by his real name, Calvin Cordozar Broadus, and most recently known as the “born again” Rastafarian Snoop Lion, Snoop Dogg boasts some of the most unique business ventures on our list. A major player in ‘90s West Coast gangster rap, Broadus was ushered onto the scene by Dr. Dre, who featured him on his first solo album following the break-up of N.W.A. in 1992; by 1993, Snoop was topping the Billboard 200 chart with his album Doggystyle. But Snoop’s image wouldn’t be complete without his ventures in filmmaking in the early 2000s—including the fist hardcore porn video to make Billboard’s music video sales charts and the Adult Video Network award-winning Snoop Dogg’s Hustlaz: Diary of a Pimp. In 2005, he founded his own production company, Snoopadelic films, dedicated to Snoop-themed films.

    In addition to having released his 13th studio album this May, Snoop Lion has become active in the world of venture capital. His estimated $135 million net worth includes a stake in Reddit, a high-end dog food company called DOG for DOG, and, as of earlier this year, Eaze, a California-based start-up that aims to deliver medical marijuana in 10 minutes or less. Dedicated Snoop lovers can also download his free sticker app, Snoopify, complete with not-free stickers of joints, chicken and waffles, Snoop’s face, and much else. According to the Wall Street Journal, the app was earning him $30,000 weekly in sales a month after its launch.

  • Pharrell Williams

    Pharrell Williams attends The 57th Annual Grammy Awards at the Staples Center on February 8, 2015 in Los Angeles, California.
    Dan MacMedan—WireImage/Getty Images

    By the time Pharrell Williams launched the funk/hip-hip trio N.E.R.D. in 1999, he’d already spent several years as part of the Virgin Records production duo The Neptunes. But cash wasn’t necessarily flowing: Pharrell told Seth Meyers on his show in April that he was fired from three different McDonald’s gigs in the late ‘90s: “I was only good at eating the chicken nuggets.” (He later got even by writing the “I’m Lovin’ It” jingle used in the company’s ads.)

    The new millennium ushered in a number of production successes for The Neptunes, including Britney Spears’s 2001 “I’m a Slave 4 U” and Nelly’s “Hot in Herre” in 2002. In 2003, Pharrell released his first solo single, and it helped prompt plenty of new business ventures. Beyond founding his own record label, Star Trak, in 2002, Pharrell has amassed some of his $80 million fortune in the fashion industry. He has two clothing labels (Billionaire Boys Club and Ice Cream), has co-designed a line of jewelry and glasses for Louis Vuitton, and last year designed a line of T-shirts for the Japanese clothing company Uniqlo. He’s also a co-owner of Brooklyn Machine Works and textile company Bionic Yarn, both of which fall within his creative collective, iamOTHER. And somehow, he still finds time for some killer creative collaborations, including with starchitect Zaha Hadid and, more regularly, the internationally acclaimed fine artist Takashi Murakami.

  • Mark Wahlberg

    Mark Wahlberg during the premiere of "The Gambler" in Los Angeles, California November 10, 2014.
    Kevork Djansezianmdash;Reuters

    Long before he was an actor starring in blockbuster movies like “The Departed” and “Transformers: Age of Extinction,” Mark Wahlberg emerged on the early ’90s hip-hop scene as Marky Mark—a pseudo-rapper name he took on perhaps to distance himself from the boy band roots of his brother Donnie, a member of New Kids on the Block. Marky Mark and the Funky Bunch had one major hit rap-dance song (“Good Vibrations”), and his six-pack abs and proclivity for dropping his pants helped Wahlberg become an iconic Calvin Klein underwear model long before Justin Bieber.

    As his music career fizzled out, Wahlberg turned to acting, earning critical acclaim for his starring role in 1997’s “Boogie Nights.” Dozens of films followed, and he evolved from an actor into a major Hollywood player, serving as producer (and real-life inspiration) for the HBO show and 2015 movie “Entourage.”

    In 2011, he and his brothers Donnie and Paul opened a fast-casual burger restaurant concept called Wahlburgers, which inevitably became a reality show of the same name on A&E. This past spring the company announced plans to open 66 new locations over the next few years, including 20 Wahlburgers in the Middle East, two at airports (Boston, Toronto), and a sprinkling of new restaurants in places such as Long Island, Florida, Philadelphia, and Las Vegas. Eventually, the Wahlberg brothers say there could be as many as 300 franchises around the globe. As Marky Mark once rapped, “If you ain’t in it to win it / Then get the hell out.”

  • arrives at the Oscars on Sunday, Feb. 22, 2015, at the Dolby Theatre in Los Angeles.
    Chris Pizzello—Invision/AP

    It seems appropriate that William Adams—or—had a couple of false starts before making it big as the founding member of the Black Eyed Peas. A debut album for Eazy-E’s Ruthless Records was shelved in 1992, and later fell through altogether when Eazy-E tragically died of AIDS in 1995. There was also a stint in the “Black Eyed Pods” before a name change and the addition of Fergie to create the rave-inspired hip-hop group we know today. After all, these days, Adams identifies himself primarily as an entrepreneur and businessman, with music coming second.

    But just as The Black Eyed Peas garnered enormous success—they’ve sold over 76 million records to date— has arrived at no shortage of success in the world of innovation. He’s channeled classes he took at LA’s Fashion Institute of Design & Merchandising into creating +, a fashion tech start-up most recently known for Puls, a competitor to the Apple Watch, and has partnered with Coke on Ekocycle, a project that promotes the use of recycled materials in the fashion world. He owned a founding share in Beats Electronics alongside Dr. Dre, and reaped the rewards when Apple bought the company for $3 billion last year. He’s Intel’s Director of Creative Innovation. And in 2012, he became the first artist to ever debut a song from another planet, when he premiered “Reaching for the Stars” from the Mars curiosity rover.

  • Diddy

    Sean 'Diddy' Combs attends the Sean "Diddy" Combs Fragrance Launch at Macy's Herald Square on May 6, 2015 in New York City.
    Ilya S. Savenok—Getty Images

    It’s been years since Sean Combs was topping the charts with songs like “I’ll Be Missing You,” his 1997 tribute to the passing of friend and musical partner Notorious B.I.G. But don’t feel sorry for Combs—a.k.a. Diddy, P. Diddy, Puff Daddy—who currently has a net worth in the neighborhood of $735 million, according to Forbes.

    With his Sean John clothing line sold in mainstream outlets like Macy’s, and with investments and partnership deals with huge companies like Diageo and upscale brands such as Aquahydrate and Ciroc vodka, Combs is the very picture of rapper turned entrepreneur. As for his advice about being a successful businessman, Combs told that it’s essential to research and understand a company before getting involved. Above all, pay close attention to how the business will make a profit. He’s a believer in the phrase, “If it don’t make dollars, it don’t make sense.”

MONEY Startups

Check Out This Business That Does Nothing But Give Away Free Stuff

And drives around New York City in a pink truck to do it.

When a friend told Anna Monzon about a pink van in New York City where she could win valuable free prizes, she was intrigued. “I love free stuff,” says Monzon, a 25-year-old commercial real estate agent who lives on Manhattan’s Upper East Side.

So Monzon began entering the contests, run by Claim it!, a New York City startup. First she’d enter a random drawing using the Claim it! app from her mobile phone. Then she’d hope for a text message on her mobile phone on a Sunday evening telling her if she won the drawing.

She got lucky and snagged several prizes. “The first thing I won were Beats headphones,” she says. “One time I won Air Jordan sneakers. I don’t wear them, so I ended up selling them on Craigslist.”

To pick up her prizes, there was one condition: She had to find the van—which changed its location in the city each day—and watch a short commercial. (She’d find where the van was parked from the company’s app.)

Monzon had plenty of company when she showed up: So far, the app has close to 100,000 users, according to Ali Abdullah, a former senior product manager at Google who started the now nine-employee business in December 2014.

Claim it! operates only in New York City and gives out prizes ranging from $25 Shake Shack gift cards to GoPro cameras. Revenue—as well as the prizes—come from advertisers who, Abdullah explains, appreciate that contestants have a 100% rate of viewing their 10-to-15-second commercials. Advertisers include P&G and Unilever Brands, Abdullah says. (He declined to say how much revenue the company brings in.)

Currently, prize winners must pick up their goodies at the van, but in the third quarter, Claim it! plans to start partnering with retailers. Users will be able to collect their prizes at retail stores, too. Recently, Claim it! did a test run at Crumbs Bake Shop, and has secured a variety of retail partnerships, he says.

Read next: From Trap to Table: Luke’s Lobster Serves Fresh Maine Catch

Abdullah came up with the idea for Claim it! after a period of joblessness, when he lost his family’s home to eviction and ended up living with friends. At the time, he says, his relationship with his girlfriend was strained and the only thing that brightened his days was receiving gifts in the mail from retired NBA star Al Harrington, whom he had befriended through Harrington’s sister, a friend. Among the gifts were a pair of LeBron James sneakers. “I had this idea: ‘These sneakers are extremely valuable’,” says Abdullah. “Should I wear them or should I sell them?” In dire need of cash, Abdullah sold that particular pair of shoes to the manager of a local store.

Eventually, Abdullah got back on his feet, found a contract job as a web applications engineer at the Clinton Foundation. But the spark of excitement he got from receiving the prizes in the mail stayed with him.

Influential investors have decided he’s onto something. Stephen Sadove, former chairman and CEO of Saks Fifth Avenue, bought a small minority stake in the business in 2014. Sadove met Abdullah at a business event and was impressed by the vision the entrepreneur showed in early demos of Claim it!

“My world was retail,” says Sadove. “I was interested in different technologies that could disrupt retail in some way. People like getting things for free. I listened to his thinking and the idea that people would view a short video to get free things. It was a very interesting concept. I decided to invest and advise him.”

Another investor is Harald F. Stock, president and CEO of ArjoHuntleigh, a medical device maker headquartered in Malmo, Sweden. They got to talking about Claim it! when Stock was having a beer in a bar near Manhattan’s Columbus Circle and Abdullah was sitting nearby, working on his computer. Stock found the entrepreneur’s approach compelling.

“On one side he’s very down to earth, very grounded, able to communicate and network very well,” says Stock. On the other, Stock says, Abdullah has impressive technical knowledge and visionary thinking. “That’s a rare breed,” says Stock.

Read next: How to Make Sure Your Small Business Outlives You

MONEY Small Business

Startup Makes Money By Giving Away Free Stuff

Claim It! lets users win prizes just for watching a 15-second ad.

When Ali Abdullah was homeless a few years ago, he was struck with the brilliant idea that would lead to his current, thriving company, Claim It! Free stuff makes people happy, so he would build a business around giving away free products that people actually want. By watching a 15-second advertisement on the Claim It! app, users are eligible to win prizes ranging from lip balm to pricey headphones. Investors understood the power of this business model, and he’s raised millions, including a six-figure contribution from just one investor.

MONEY Small Business

Entrepreneur Cooks Up Profits With His Grilling Invention

Brad Barrett was working in the chemical industry. Then he found his true calling.

MONEY small businesses

Immigrant Entrepreneur Launches High-Tech Mailbox Business

Nigel Thomas' American Dream was to start his own business. This is it.

Nigel Thomas and his family moved to America from the Caribbean when he was just seven years old. Education and having a thriving career were always important in his culture, but Thomas yearned for something bigger than that security. When his employer offered a severance package to employees, he saw his opportunity to fulfill his dream of owning his own company. The venture Thomas founded is GoLocker, a service that allows customers to get their packages at their convenience from lockers inside 24-hour grocery stores. With five sites in Brooklyn currently, he hopes to expand to as many as 15 locations before the end of the year.

MONEY Travel

Richard Branson’s Dream Project Comes Closer to Being a Reality

Virgin Atlantic President Sir Richard Branson
Rex Features via AP Images Sir Richard Branson

Virgin Group founder strikes again.

Richard Branson, the iconic, eccentric entrepreneur at the helm of the Virgin Group, seems to do pretty much whatever he wants. If he wants to give his employees unlimited vacation or a full year of paternity leave, he’ll do it. Heck, he’ll even give the greenlight to putting the Sex Pistols on credit cards because … why not?

At a press event on Tuesday in Miami, the man who has already helped launch successful airlines on multiple continents and is even venturing into space travel offered details about his latest travel operation. “It’s no secret that I’ve dreamed of starting a cruise line for a very long time,” Branson said.

But before Branson spoke to the press, he had to make an appropriately Bransonesque entrance at the event, held at Miami’s Perez Art Museum. “With characteristic flair, Branson arrived at the event in a helicopter that took off in a cloud of bright red smoke,” the industry publication Cruise Critic reported. “When he landed, Branson emerged wearing red shorts, a white shirt and a red captain’s hat while waving a Virgin Cruises flag.”

This week’s event was actually the second time Branson has introduced the forthcoming launch of Virgin Cruises. Last December, the Virgin Group said it would soon be “making waves” in the cruise industry with the new line. “We plan to shake up the cruise industry and deliver a holiday that customers will absolutely love,” Branson said at the time. “They’ll be sailing on the latest ships offering great quality, a real sense of fun, and many exciting activities all delivered with the famed Virgin service.”

On Tuesday, Branson and Virgin Cruises President Tom McAlpin offered more details about the operation. The plan calls for three newly built Virgin Cruises ships to be deployed by around 2020, with the first based in Miami and Fort Lauderdale for weeklong itineraries exploring the Caribbean.

Many of the specifics haven’t been announced—and apparently, quite a few haven’t been decided upon. Branson is asking interested travelers to visit to offer input on anything and everything they want in a cruise line.


8 Epic Business Failures with Donald Trump’s Name on Them

Donald Trump
Ian MacNicol—Getty Images Donald Trump

If the Trump presidential campaign fails, it won't be the Donald's first misfire.

On Tuesday, Donald Trump threw his name into the ring as an official candidate for president in 2016. “I’m using my own money. I’m not using the lobbyists. I’m not using donors,” Trump explained of his candidacy, before adding a heaping dose of trademark bluster: “I don’t care. I’m really rich.”

As for why he’s running, Trump pointed to his business sense and declared, “We need somebody that can take the brand of the United States and make it great again.”

Yet time and again over the years, the Trump brand has been featured in many embarrassing high-profile flops in the business world. Here are some of the misfires attached to the “Trump” name.

Trump Shuttle
In 1989 the Eastern Air Shuttle was reborn as the Trump Shuttle, complete with a large “T” on the tails of the planes and—no joke—”gold lavatory fixtures.” The goal was to create a top-notch luxury flight service—they even paired with a company that rented laptops, which was cutting edge at the time—but the operation was hemorrhaging cash within weeks and was completely out of business by 1992.

Trump: The Game
The original catchphrase for the Monopoly-like Trump board game introduced in 1989 was the Trumpism “It’s not whether you win or lose, but whether you win!” Sales were underwhelming, to put it mildly. But after Trump became a cultural phenomenon in the reality TV show “The Apprentice,” the game was back on the market featuring a new expression: “You’re fired!”

Trump Magazine
“The Trump Brand evokes elegance and TRUMP Magazine will reflect the passions of its affluent readership by tapping into a rich cultural tapestry,” explained a 2007 press release introducing Trump Magazine. A year and a half later, the quarterly periodical, billed as a “highly anticipated ‘must read’ among VIPs and influencers,” had ceased publication.
Billed as his “biggest venture to date in the $80 billion online travel industry,” Donald Trump introduced this travel search engine powered by Travelocity in 2006. The site was supposed to host “Trump Picks” and “Trump Deals,” and it was accompanied by the introduction of The Donald’s “first-ever email address” ( which he would be using to “offer travel tips and advice.” The site was shut down a year later.

Trump Casinos
The Atlantic City casino Trump Plaza, which was built in the 1980s at a cost of $210 million, was sold off at the “fire sale price” of $20 million in 2013, not long before several casinos shut down in the fading gambling destination. Trump insists that he cashed out the vast majority of his interests in the Trump Plaza and nearby Trump Taj Mahal long before Atlantic City property values tanked, but earlier this year he reached an agreement to keep his name on them.

Trump Mortgage
“Donald Trump is putting the suit and tie back in the mortgage business,” a 2006 press release explained of his brand new venture, Trump Mortgage. Whatever that means. Less than two years later, the suit and tie were back in the closet, or perhaps up for sale at the consignment store, so to speak, as Trump Mortgage closed up shop. Trump speedily downplayed the venture as well, saying, “The mortgage business is not a business I particularly liked or wanted to be part of in a very big way.”

Trump Steaks
AdAge described Trump Steaks, featured on the June 2007 cover of the Sharper Image catalogue, as like “a ‘Saturday Night Live’ spoof, but it’s not.”

Trump Vodka
Donald Trump made no secret of the fact that he doesn’t drink. Nonetheless, a decade ago he rolled out Trump Vodka and promised it would be “a major player in the vodka arena” because “it’s a superb product and it’s beautifully packaged,” and “there’s nobody who markets better in the luxury category than Donald Trump.” This is one “major player” that disappeared from the marketplace several years ago.

MONEY Startups

This One-Man Business Sells Millions Worth of Swag Out of a Garage

"Your Logo Here" written on canvas tote bag
Tony Garcia—Getty Images

One key lesson: Outsourcing.

Need a jumbo canvas shopping bag printed with your company’s logo? What about a twist-action ballpoint pen with your company’s name and web address on it?

Harry Ein is your man.

Since July 2010, Ein has run his one-person business, Perfection Promo, from the three-car garage at his house in Walnut Creek, Calif., providing swag to clients from corporations to sports teams. He started his business after departing a former employer in the same industry.

Since then, he says he has won business from clients including Microsoft, Safeway, Benefit Cosmetics and the NBA. This year, he projects revenue of $4 million at the profitable firm. In 2015, Advantages Magazine, a trade publication, named him the #1 sales rep of the year for promotional products.

Ein is one of the growing number of Americans who are creating businesses that are breaking $1 million in revenue with no employees other than the owners. U.S. Census Bureau counted 30,174 “nonemployer” firms that had revenues of $1 million to $2,499,999 in 2013, up from 23,176 in 2009—a 30% increase.

So how does Ein do it all as a one-man band? Well, he doesn’t, not exactly.

His not-so-secret strategy to keeping his firm ultra-lean is outsourcing. By reading industry publications and networking in his industry, he found out about a company called iPROMOTEu, in Wayland, Mass. It provides back-office services such as trafficking orders and collecting money from customers to independent firms like his. By affiliating with iPROMOTEu, he says he has been able to free his time to focus on sales. And it costs him less than maintaining his own staff. “If I didn’t have a billing company and all of that back end stuff, I’d have to have three to five employees,” he says.

Here’s how Ein built his profitable business to $4 million in annual revenue since starting it in July 2010.

Make the most of what you already know. When Ein was getting started, he picked a business in which he could use his natural gift for selling. In his late teens, Ein used the food money his parents left him while they were on vacation to buy a few Tickle Me Elmo dolls when the craze for them was in full swing and they were selling out. He brought the toys to a local mall and sold them to frantic shoppers who couldn’t find them in stores. “I was able to sell them for double and triple the cost,” he says.

After college, Ein worked as a sales executive at The Ad Solution, a provider of branded merchandise such as office gifts, getting crash course in his industry. He worked there nearly nine years before making the leap into his own firm. The knowledge and connections he built paid off. He says he hit $700,000 in sales his first year.

Live lean. Now that Ein is married and has a two-year-old son, he has the type of financial responsibilities that drive many people into the seeming security of a W-2 job. By working from home, he is able to reduce financial pressure on himself, keeping overhead at his business down and his commuting costs to zero. If he needs to meet with customers face to face, he goes to see them.

There’s an added bonus. Working from his home office gives him more time to play with his toddler. “We have a park that’s 20 yards from our house,” says Ein. “At 5 pm, I’ll try to take him over.”

Do the math. Ein decided on his current outsourcing model after talking with owners of other promotional products companies about how they were running their firms. One owner said that his company—which brought in $20 million in sales with 25 employees—had been better off when it was just one or two people, because of the costs and issues that arose when hiring employees. “Sometimes we’re not profitable,” the owner told him. That helped Ein settle on his own, outsourced business model. “You should do as much research as you can on what others in your industry are doing, and how you can streamline your business the best way,” he says.

While Ein isn’t averse to hiring employees, he finds he has the help he needs right now from iPROMOTEu. Meanwhile, he likes knowing he is keeping the people who make items like silk-screen T-shirts for him at other firms busy. “It might not be employees under my business name, but I know we’re putting people to work,” he says.

Don’t be afraid to talk with your competitors. Ein finds it more beneficial to share information freely than to play things close to the vest with rivals. “They are going through the same experiences as you,” he says. For instance, he’s never hesitated to recommend good factories to other firms. They, in turn, have suggested other plants to him. “People who don’t want to share anything hurt themselves,” says Ein. “When you can share ideas you can find resolutions that will help you, as well.”

MONEY Small Business

Brooklyn Entrepreneur Happily Works 7 Days a Week

Artist Sigal de-Mayo explains how she launched her business and opened her first store.

Sigal de-Mayo is the creative force behind Insiders1, a Brooklyn-based small business that creates wearable and usable art out of photo collages she shoots, designs and prints. After 16 years selling at street fairs and holidays markets, Insiders1 has just opened its first brick-and-mortar location in the Williamsburg neighborhood of Brooklyn. Wares range from leather gloves, bags, and wallets to silk scarves, clocks and puzzles. Her advice to other entrepreneurs: Make sure you have the passion necessary to dedicate all your time and energy to your company.

Your browser is out of date. Please update your browser at