Seeking fame and fortune? Don’t mind abdicating privacy? Try cruising the rich-and-famous road.

Rich and famous is a popular dream. But most rich folks aren’t famous. They own trailer parks or small businesses. They’re accountants or doctors, not living fantasy lifestyles. We think big limos, Super Bowl rings, Oscars, owning sports teams or making movies. This road is the stuff of grade-school career aspirations— baseball player, actress, Oprah, Tiger. This road’s riches can be planned for, though realistically it’s closed to most by the time we’re adults. It requires a young start. Kids dream of stardom. Such kid dreamers kid themselves. Be warned—though this road’s riches are legitimate, it’s hard work, and the odds of success are super slim.

This road has two forks. One is talent—LeBron James, Beyoncé, and Jennifer Lawrence. The other is media mogul—Ted Turner, Rupert Murdoch. The media mogul road is more attainable—you needn’t throw a tight spiral or look like Charlize Theron. You just need what any successful businessperson needs—perseverance, smarts, and luck. It happens later in life, too. But that doesn’t make the talent road less tempting.

There’s an occasional crossover here—talents who become moguls and vice versa, though it’s rare. Oprah (worth $2.8 billion)1 is the richest talent-mogul crossover. She parlayed a newscaster career (talent) into a talk show she produced (talent and mogul). En route, she starred in movies (notably The Color Purple, as a talent) and as Broadway producer (also The Color Purple, now as a mogul). Such blending is rare. Martha Stewart (worth $220 million)2 is a talent in her own mogul world. Talent/moguls tend toward bigger wealth than pure talents. And don’t forget those diminutive twins—Mary-Kate and Ashley Olsen. I’m too big a fuddy-duddy to know which is which, but their production firm and clothing lines make them crossovers—worth $150 million each.3

Another recent crossover, but this one initiating from mogul land, is pop-culture phenomenon Mark Cuban (net worth $3.2 billion).4 In addition to his other fine crossover qualities, Cuban is tough—cares not one whit what his critics say—even has a beyond-great sense of humor about it. In this sense, he’s a textbook founder-CEO (Chapter 1). The former bartender began building wealth as a dot-com cowboy, founding, a web radio station, with a college pal in 1995. Just before 2000’s dot-com crash, he made a timely sale to Yahoo! for $5.7 billion in stock.

Not only was his firm’s sale well timed, but he didn’t wait for Yahoo! to tank in the tech crash. He swapped a huge chunk of change with Ross Perot for the Dallas Mavericks, and he’s been annoying NBA officials ever since. By mid-2006, Mark had already been fined in excess of $1.6 million by NBA officials for his courtside antics and quick temper.5 For claiming the league was as poorly run as a Dairy Queen, Mark paid penance by donning a paper hat and serving soft serve for a day at a franchise in Coppell, Texas.6

In 2000, he cofounded 2929 Entertainment—a media holding company—and he’s chairman of AXS, a high-definition cable station. In 2007, he joined the cast of Dancing with the Stars—a reality show pairing athletes and D-list celebrities with professional ballroom dancers for a weekly dance battle. This qualifies him as talent as much as other celebrities who’ve appeared on the show. (Though he’s a bit of a cheater. At one point, he made a living as a disco-dance instructor.)7 Now he stars on a VC reality show, Shark Tank, where startup wannabes pitch their ideas to him and other “celebrity” investors. Hilarious YouTube clips abound.

My editor feared I sounded too mean-spirited in describing Cuban—particularly my last few sentences that don’t make him sound like a great talent—and that you wouldn’t like that. And it’s true—I really haven’t said anything laudatory about him. Well, I’m pretty sure it’s the other way around and that I haven’t said anything sufficiently nasty about Cuban to make him really like it. For him to love it, I’d have to rag on him pretty heavily. And I like him. OK, Mark, this is just for you: You’re a dirty rotten blah, blah, blah. Feel better? For the rest of you readers, my point is that if you’ve made a bundle as a mogul and want a taste of fame as well, you can go from the rich to the famous as a celebrity, just like Mark Cuban did.


So how do you become a rock star, NFL pro, or Jennifer Lawrence? This road’s journey starts young. If you’re past age 15 and starting football, you won’t ever go pro. Sorry. For acting, maybe you can start a bit later—age 18—though many start much younger. Any road requires industry and perseverance. Think of a 50-year-old, financially successful CEO—he’s likely been at it since he left college, maybe 30 years! But a 35-year-old pro athlete has been at it almost as long. Tiger Woods famously started golf at age two.8 His dad probably enjoyed that more than two-year-old Tiger did. But for winning the Masters at age 22—starting at age two seems right. As Michael Jordan said, “Being a pro is practicing when you don’t want to.”

Getting Started

Getting rich as a talent requires youth or a youthful decision. A 35-year-old newbie aspirant won’t make it in Hollywood, the NFL, golf, or pretty much anything—no matter what. That doesn’t mean older folks aren’t talents. Katharine Hepburn still starred at age 87. But she also starred young. Can miracles happen? Yes, but almost never. Glenn Close didn’t land her first movie role until she was 35. Soul queen Sharon Jones didn’t start singing professionally until age 40 and nabbed her first chart hit at the tender age of 54. The key? Recall the “almost never” part. Most celebs start very young. If you aren’t and haven’t, the cost of this book will have been worth it, because now is the time to stop wasting time considering this road and seek another.

If you’re young and determined with grit—now what? Practice. All day, every day. Successful stars start young but are also freakishly single-minded. Britney Spears and Justin Timberlake worked far harder as children than probably anyone you ever met. Pro athletes generally led monastic childhoods, rising pre-dawn, practicing before, during, and after school. So start waking at 5 AM now for wind sprints.

Want to be a rock star? Join a church choir, play guitar at the old folks’ home on weekends, play county fairs. Never decline a gig, no matter how mortifying. Have you seen The Voice? Pretty much all of them have been singing for crowds since age nine.

If you want to act, do it. Take classes at your local community college. Big cities have lots of choices. Classes are really just another excuse for practice. To self-teach, pick up Respect for Acting by Uta Hagen and An Actor Prepares by Konstantin Stanislavsky—the book on method acting. But find a local theater, improv class, or summer stock and just do it.

Sell Yourself

To succeed, you must sell yourself or you miss gigs. If you make it, you’ll have an agent selling you. (Entertainment and athletics are highly unionized. You must play by union rules.) But how can you get to needing an agent? Back Stage magazine lists casting calls in every major city for TV, films, voiceover, radio, you name it. It even has listings for nonpros like you! You can search and post your resume (skinny though it is) online at You need a headshot (8 × 10 black-and-white photograph—have a pro do it, or a very skilled friend) and a phone number. The listings tell you just what you need for the audition—a prepared monologue, an accent, eight bars of a Broadway tune. With Back Stage, a stack of headshots, and some postage, you’re ready. Getting the job—that’s up to you. It’s selling.

Eventually, you’ll need an agent. They’ll find you higher-profile work but also take a cut of profits. Agents are also listed in Back Stage magazine. Note: Never pay to audition or have an agent look at you. Real agents won’t ask for money until you get paid. If they want money up-front, it’s a scam. Always. Run. One day, like Brad Pitt, you can be picky. But at first, if someone offers you seven bucks an hour to wear a chicken suit and dance, start dancing. For more on getting started, Back Stage is a great source overall. (Read the section on “Avoiding Scams” first.) Also, pick up Breaking Into Acting for Dummies by Larry Garrison and Wallace Wang, which covers acting’s business side, from resume building to finding every kind of job and dealing with unions.

Eventually, you must join a union. You can’t get certain jobs unless you do, but then you’re bound by draconian union rules. Remember the 2008 Hollywood writers’ strike? Many writers probably didn’t want an unpaid four-month vacation, but if the union strikes, them’s the breaks.

Rock On

The same rules apply for would-be rock stars: Sell yourself and take whatever work you can. Walk into every bar and offer to play—for free! (Once you get a following, you can demand money.) Create a press kit—a picture, some reviews (have your mom write them—if you’re too old to have your mom write them, then you’re too old), newspaper clippings, and a CD. Hit as many venues and booking agents as you can. It’s a numbers game! The more people you contact, the better your odds.

Once upon a time, it was all about the studio album. Not anymore! With a decent computer, pretty much anyone can make a CD, and anyone can buy most any single song through iTunes. You can even make a YouTube video, like Justin Bieber. But to make it big, you either have to be a songwriter (see Chapter 8) or go on tour. Even big names like Madonna, U2, and rapper Jay-Z (more on him later) have abandoned traditional record labels and signed huge contracts—$120 million for Madge and $150 million for Jay-Z—with Live Nation.9 Live Nation, a spin-off from radio conglomerate Clear Channel, owns and operates hundreds of music venues internationally.

Before you can negotiate a $150 million deal, though, you must log hours on the road. So how do you find a “booking” agent? Same as actors! Again, don’t pay up-front. Second . . . sell! Booking agents are listed in the Yellow Pages or with your local union. Send them a press kit and invite them to gigs. Required reading: All You Need to Know About the Music Business by Donald S. Passman walks you through finding an agent and negotiating a contract. And for a clear-eyed look at the industry, read So You Wanna Be a Rock & Roll Star by Jacob Slichter or Everything I’m Cracked Up to Be by Jennifer Trynin. You may not want to anymore after reading them.

The Sporting Life

Athletes’ paths are better defined. High school sports star. Recruited for college. College standout. Recruited for pro team. If you don’t make it as a high school sports star, take another road. It’s very rare to enter top pro leagues direct from high school. Some have, like Kobe Bryant and LeBron James, but don’t try it. If you suffer a career-ending injury, you’ll at least have a college degree. Tennis champs generally don’t go the college route. Many baseball players go straight from high school to the minor leagues, but few of them ever make it to the Big Show. Olympic gymnasts’ careers are usually over by age 19, giving them time for college afterward, but they generally aren’t “rich and famous.” Tiger went to college! Sure, he dropped out (like Steve Jobs and Bill Gates), but first Stanford wanted him.

Pro athletes require an agent. IMG is perhaps the best-known sports agency and manages many huge names. For others, check the Sports Agent Directory ( Again, don’t pay up-front! They get paid when you do—always. Your agent helps negotiate better contracts and lands sponsorships and Wheaties boxes. That’s where the big bucks are (like lunch boxes and action figures for writers—see Chapter 8). So, to become a pro athlete: (1) Practice. (2) Finish high school. (3) Get recruited to college. (4) Find an agent. (5) Become the face of Nike. Easy as that. Now go do more wind sprints.


The talent road is youthful, but unreliable. Persistence has no high correlation with financial success. Nor does talent alone. No matter how talented an actor you are, odds are seriously against you ever being employed in acting. The numbers are scary. According to the Bureau of Labor Statistics (BLS), in any year there are only about 70,000 acting jobs. Not 70,000 actors—70,000 jobs (some as dancing chickens). No way to know how many wannabes are waiting tables instead. The Screen Actors Guild and American Federation of Television and Radio Artists (SAG-AFTRA—the TV and movie actors union) has about 160,000 members, but even SAG-AFTRA admits only about 50 earn, say, in excess of $1 million per picture. Only a tiny elite make much more. The rest, according to the BLS, make a median salary of $18.80 per hour—when they’re working!10 Recall those Dell computer commercials with the floppy-haired kid yelling, “Dude, you’re getting a Dell!”? He did countless Dell commercials for three years or so—and likely earned quite a bit. Then he got busted for drugs, couldn’t get work, and was relegated to tending bar at a popular Manhattan Mexican restaurant, Tortilla Flats.11 Years later he’s back in the biz, but there was a long drought.

Let’s assume 100 unemployed actors for every acting job (probably a low estimate). That means about a million and a half claim to be “actors” when their tax returns don’t so indicate. (Most don’t earn enough to pay income taxes.) So if there are 1.5 million of you and 50 big earners, you have about 0.003 percent odds of hitting it big. You might scrape out a living, but at that median hourly rate, you’re likelier making $25,000 a year than anything close to Jennifer Lawrence status.

Musicians face similarly daunting odds. There are no numbers for out-of-work musicians, but very few become the Rolling Stones. Or athletes! Odds are best for baseball players. If you play high school varsity, the NCAA says you have about a 0.45 percent shot at making the major leagues.12 Terrible! And you still must be a superstar to make a superstar salary. Minimum salary for Major League Baseball players is $500,000.13 Not bad, but you don’t get super rich on that because you don’t last long enough. If you can’t hit a fastball, try hockey—the odds are 0.32 percent you’ll play professionally—but the top pay isn’t so high. Pay is high for top football stars but the odds are worse (0.08 percent chance you’ll go pro). Basketball? Only 0.03 percent. Women have it worse. Varsity female high school basketball players have a 0.02 percent chance of going pro.14 They have fewer teams. It’s an unfair world. Still, overall those odds beat the odds of being Jennifer Lawrence.

You may say, “But Jennifer Lawrence makes $26 million a movie!” With that, you don’t need a lifelong career. One $26 million movie—pay your manager, accountant, trainer, chef, Kabbalah coach, and yoga instructor, take the $10 million left over, and retire. Fine, but to make the $26 million, you still actually need to be Jennifer Lawrence—and that requires having started young or possibly a Faustian deal with the devil. Which raises another trait for all the roads to riches! Folks making $26 million a picture aren’t interested in making one picture and retiring. They don’t quit—they’re tenacious and driven. You must be, too. I’m not trying to dissuade you—merely warn you. While on the talent road, you may want to cultivate other functional skills so transitioning to a more reliable road is less painful.

Not So Rich or Famous

This is also far from the richest road—even for those making it huge. No Forbes 400 member is a talent-only richie. Oprah is more of a mogul. The top-earning pure talent is Taylor Swift—taking home a reported $170 million in 2016.15 With mogul potential, Taylor should be Forbes 400 material someday. But take Madonna—something is materially wrong with the Material Girl. She made $76.5 million in 2016 and big bucks for decades, yet her net worth is only $560 million.16 Given her huge earning tenure, she’s lagging. She’s been huge for over 30 years—if she saved a mere $10 million a year and invested wisely, she’d have at least $1 billion by now. How much can rhinestone-encrusted bustiers cost?

Few actors accumulate astronomical wealth. Matt Damon reportedly made $55 million in 2016, beating his BFF Ben Affleck by $12 million. Ben’s onetime steady, the multihyphenate Jennifer Lopez, took home $39.5 million in 2016.17 These folks are about as big as you get. But if Madonna can’t reach the highest wealth echelons, they won’t, either.

A Short, Unsteady, No-Privacy Road

Then, too, talent life is fickle—an easy road to fall from. You’re only as good as your last movie, hit song, or home run—but also the lifestyle tends toward self-destruction. I needn’t dwell here, as it’s obvious from the news. Peer pressure, drugs, divorce; these all fuel self-destruction and don’t aid wealth-building. And—no privacy. The stars simply can’t go out in public without attracting a mob, putting them in physical danger. Don’t believe it? A friend of mine tried going with Whoopi Goldberg to the local 7-Eleven at 3 AM. They had to flee from the paparazzi for their safety. And Whoopi’s no tabloid fixture.

If you don’t do yourself in, your allies may. Boxer Mike Tyson accused his manager, Don King, of mismanaging his assets, and ultimately won a $14 million settlement.18 While Mr. King probably wasn’t the wisest custodian of Tyson’s assets, Tyson famously lived an excessive lifestyle, throwing money away with both gloves. Child stars are ultra vulnerable since they need scrupulous parents and ethical management. Gary Coleman (from the 1980s sitcom Diff’rent Strokes) earned at least $8 million as a kiddie star, much of which his parents paid themselves in management fees.19 He later sued and won. But his settlement couldn’t protect him from bankruptcy or, sadly, an untimely death. Corey Feldman (in a string of 1980s hits including Stand by Me) fell prey similarly—his folks left him with only about $40,000.20 Rip-off management isn’t all. Once-upon-a-time massive talents often don’t remain on top for long. Where is Macaulay Culkin now? On this road, you start early, must star early, and then stay persistent.

Hollywood demands youth and beauty. Pro sports require healthy joints. Even the music industry doesn’t favor the old. Springsteen, U2, and Madonna are still making hits and touring. Fleetwood Mac, with all members over the retirement age, took in over $75 million touring in 2015.21 All still huge, but that’s about it. Older acts are notable, though few, compared with the endless roster of young bucks on the radio. Ichiro Suzuki is a baseball superstar elder-statesman, yet his career is in its twilight. Few pro athletes are on top in their 40s. Actors have it easier than actresses. Harrison Ford, Liam Neeson, and Denzel Washington are still considered sexy. But not older actresses! Even though Dame Helen Mirren is probably more age-appropriate for Mr. Neeson, she’s unlikely to be cast as his romantic interest. Ditto Michelle Pfeiffer, who’s still got the look but gets cast as the family matriarch, not the love interest. Leading ladies, like athletes, are usually done by their mid-40s. This book’s first edition featured Cameron Diaz prominently. When was the last time you saw her headline a blockbuster? It’s no accident that onetime starlets Kate Hudson, Sarah Michelle Gellar, and Jessica Alba launched businesses in their 30s—the First Road is richer and more sustainable than life on the silver screen. These ladies were savvy enough to see it.

With ridiculously low odds on the far-from-the-richest of the roads, and lots of ways to do yourself in (or have your supposed allies do you in), are you sure you want to continue down this road? If you do, no one but you will ever stop you.


A more reliable way to wealth and celebrity is becoming a media mogul. Moguls straddle the breadth of media and entertainment. They own studios, cable companies, networks, record labels, magazines, and maybe sports teams. Moguls even produce movies and music. As opposed to talents, moguls are far richer. The Forbes 400 is littered with moguls:

  • Michael Bloomberg, Bloomberg founder and former New York City mayor ($45 billion)
  • Charles Ergen, founder of EchoStar ($14.7 billion)
  • Rupert Murdoch, News Corp chairman ($11.1 billion)
  • David Geffen, founded Geffen records and cofounded DreamWorks, college dropout and former mailroom clerk, erstwhile friend of the Clintons ($6.7 billion)
  • Sumner Redstone, owns major stakes in Viacom and CBS; he gave Tom Cruise a public upbraiding (which Cruise likely deserved) ($4.7 billion)22

It goes on and on—through George Lucas ($4.6 billion), Steven Spielberg ($3.7 billion), and beyond. You get the point. Not a single pure “talent” among the richest of the rich, yet plenty of moguls. Bigger bucks and longer-lasting opportunity! Murdoch is 85, Geffen’s a spry 73—both in their prime. It requires grit, determination, and business savvy, but not Jennifer Lawrence’s looks or youth.

Though I’ve listed the biggest of the big, there are obviously myriad minor moguls, too. Consider my friend Jim Cramer (estimated net worth $50 million to $100 million)23—a somewhat older guy (i.e., older than Jennifer Lawrence) who parlayed OPM success (see Chapter 7) into founding and then moguling into celebrity. There’s no escaping Jim—on TV, in books, everywhere. His high-energy, eclectic TV show makes him a legitimate talent. But Jim didn’t start there. Before, before his hedge fund, before Goldman Sachs, before Harvard Law, he was a journalist on one of California’s more unsavory beats—carrying a hatchet and gun for protection.24 Multitalented, Jim had big but not super-mondo successes on multiple roads before settling in as a mogul and talent. The point: You needn’t make it huge to make it here.

You can start small and build. Look at what’s available on cable today—500 channels or more! And with Americans increasingly fleeing high-tax states for less punitive ones, there’s increasing need for regional radio, news, and entertainment. But be warned: To mogul well, you need business skills. Read Chapter 2 on how to run a business and Chapter 7 on private equity. Buy enough little regional media businesses and you become the force to be reckoned with.

Mistakes to Mogul-ness

There’s really only one major mistake here—not diversifying. A perfect example is how those who concentrated in newspaper-based media have run aground. Newspapers, once hot, today are not. Yes, Rupert Murdoch may have bought the Wall Street Journal as a toy. But scour the Forbes 400 and you’ll learn lots of lessons. One: Newspapers are now a way to lose money.

It wasn’t always so. William Randolph Hearst’s fortune spawned generations of wealthy Hearsts—and made young Patty Hearst a kidnapping celebrity in 1974 (like Eddie Lampert in Chapter 7, but Lampert handled it better). Joe Pulitzer, of the Pulitzer Prize, built an empire. So did Si Newhouse, whose fortune continues after his death because he had the foresight to diversify outside papers.

Newhouse was and remains such a New York City institution—a Staten Island ferry bears his name.25 He became his family’s main provider at age 13 and took over his first newspaper, the Bayonne Times, at 16. (Even though moguls don’t need to, he started young. Like Jennifer Lawrence!) In 1922, at age 27, Newhouse bought his first entire newspaper, the Staten Island Advance, for $98,000, which he owned his entire life.26

For all his success, Newhouse only founded one wholly new newspaper. He was an acquirer of down-and-out papers he could turn around in an area soon to boom. Newhouse was a bootstrapper— a wise decision for any founder-CEO. (See Chapter 1.) He plowed everything back in, was ever cost conscious, and fought off unions as costly and contributing to poor quality. At one point, Newhouse’s media empire was America’s third largest, behind only Hearst’s and Scripps-Howard’s. Then he diversified—into TV, cable, radio, and magazines. When papers started declining, they didn’t take him down, too.

When he died in 1979, he left his two sons his firm, Advance Publications Inc., with 6 TV stations, 15 cable stations, a handful of radio stations, 7 magazines under the Condé Nast banner, and 31 newspapers—and the Staten Island Advance. Plus cash.

Side note: Successful wealth builders tend to have kids who aren’t. Maybe life is too easy for them. But not with Newhouse’s sons. Samuel and Donald kept building, adding high-profile magazines including The New Yorker, Vogue, Vanity Fair, and Gourmet.27 They are among the few who’ve been on the Forbes 400 every year it’s been published (since 1982)—a very tough feat. They’re now each worth $10.5 billion.28

The Newhouse empire thrived only because it diversified away from newspapers. You can’t find big new newspaper fortunes today. Big papers have withered from free Internet news. Small city papers withered further from losing classified advertising to the likes of eBay and Craigslist. The lesson: Don’t concentrate within one media area—diversify and be all media.

A Hipper Mogul Road

Much better than newspapers today? Hip-hop—it spawns boodles of cash. And hip-hop fortunes all seem well diversified. (Note: Like our pure talent friends, hip-hop mogul is a highly unlikely road. Start young and get a college degree in case it doesn’t pan out.)

Sean Combs (aka “Diddy”) founded Bad Boy—a media empire including a record label, clothing lines, a movie production firm, and restaurants. He’s been a performer, music and TV producer, writer, and even appeared on Broadway. In 2016, his business ventures earned him $62 million, and he’s worth approximately $750 million.29 Russell Simmons, another diversified hip-hopreneur like Combs, is worth an estimated $325 million. Simmons built his fortune with two record labels and a clothing line.30 (Hip-hop moguls all seem to have clothing lines.)

Andre Romelle Young (better known as Dr. Dre) joined the hip-hop mogul elite in 2014 via a slightly different path. Like all good impresarios, he launched his own label, Aftermath Entertainment, in 1996—and he remains CEO today. But the real payday came nearly two decades later. In 2008, Dre suggested he and record producer Jimmy Iovine launch a shoe brand. Legend has it Iovine said, “[colorful epithet] sneakers—let’s make speakers.” Soon they took the world by storm with wireless headphones that actually sounded good. Apple bought Beats in 2014 for a cool $3 billion, netting Dre about $500 million.31 He earned another $33 million in 2015,32 partly from producing the NWA biopic (and his life story) Straight Outta Compton. Today he’s worth about $710 million, and like Diddy, he has high billionaire potential.33

Also high on the list is Shawn Corey Carter (once accused of stabbing a rival in the stomach, for which he got three years’ probation), also known as rapper Jay-Z.34 When launching his career, Carter wisely took a stab at cutting out all middle men—the record label, distributor, manager, producer—to keep more himself. And it worked and paid off—huge. As a relative unknown, he launched his own record label, Roc-A-Fella Records, with friends. In 1996, they released the first Jay-Z album. In this way, he was a classic founder-CEO bootstrapper. He then started a riotously popular clothing line, Rocawear, which he sold in 2007 for $204 million. Though he sold the rights to the brand, Carter kept his stake in the firm and still directs marketing, product development, and licensing.35

Like any good media mogul, his income sources are diverse. He was formerly CEO of both Def Jam and Roc-A-Fella Records. He has a successful music career and his gig designing clothes. He owns the expanding sports club chain 40/40 Club. He has a film career, a bevy of hefty endorsements, royalties, publishing rights, and he manages other artists. (They’re called artists even if you can’t see what they do as very arty.) He’s been a spokesperson for Budweiser and serves as a marketing consultant for Anheuser-Busch. Like any true mogul, he bought a sports team—he owned a sliver of the Brooklyn Nets—but sold his stake in 2013 after launching a sports talent agency, Roc Nation. Now he bides his time with Tidal, the music streaming service he took over (leading a consortium of musicians) in 2015. Forbes estimates his 2016 income at $53.5 million,36 and his net worth is $610 million.37 Movie stars, eat your hearts out.

At the rate he produces, manages, acquires, designs, and creates—as long as he doesn’t allegedly stab anyone else (unlikely—his wife, Beyoncé, and daughter, Blue Ivy, keep him in check), he should be Forbes 400 material in no time. Like my Mark Cuban comments, my editor winced at the stabbing comments, seeing them as demeaning and mean-spirited on my part and likely to trouble you, my reader. Jay-Z would be actually offended if I covered him and didn’t mention the stabbing as he has promoted it himself as part of his bona fides in hip-hop-reality. If you want to take a stab down this road, you need sharkskin.

You also need a smart financial plan. Curtis James Jackson III (aka 50 Cent, pronounced “Fiddy Cent”) once seemed a shoo-in for the rapper-mogul hall of fame. His “G-Unit” brand had all the usual—record company, clothing line, sneakers, and licensing rights galore. In 2004, he became the face of Vitaminwater, basically a glorified artisanal Kool-Aid (with extra vitamins for extra cachet). But he skipped the normal cash payout and took a stake in the parent company, Glaceau, which paid out handsomely when Coca-Cola bought it for $4.1 billion in 2007. That bumped his net worth near $500 million, putting him on the road to the Forbes 400.38 But it didn’t last. He filed for bankruptcy in 2015—ironic for a guy who called his debut record Get Rich or Die Tryin.’39 Even big wealth is fleeting if you aren’t careful.


As a media mogul, you should flip to Chapters 1 and 2 on being a CEO and read the books listed there—the same lessons apply. For riches on the strictly “entertainment” road, try the books mentioned earlier in this chapter, as well as these:

  • Audition by Michael Shurtleff. This is the book for working actors, written by a guy who actually casts shows and films and knows what he’s seeking. Your first stop on the acting road is here.
  • An Agent Tells All by Tony Martinez. To act or be in any “entertainment” field, you need an agent. This book gives you valuable shortcuts from someone who knows.
  • Swimming with Sharks directed by George Huang. You got me, this isn’t a book. It’s a must-see movie for anyone considering a Hollywood career. This just may cure you of your obsession if you aren’t sufficiently and deeply motivated.
  • It’s Not about the Bike: My Journey Back to Life by Lance Armstrong and Sally Jenkins. Think you’ve had it rough? Try being told you’re as good as dead at 25. If you seriously want to be a professional athlete, read Armstrong’s tale to see if you have the grit. Don’t be deterred by Armstrong’s later admission of steroid use. The mental and physical struggle of his cancer recovery is still real.


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