CHAPTER 2

SUCCESS IS A PITFALL

In 2016, Ebro in the Morning interviewed a nobody named “Cardi B.”¹ Hot 97, which broadcasts the show, is a powerhouse in the world of hip-hop. The show’s hosts, Ebro and Rosenberg, are the industry’s established sentries. Their word is platinum. One bit of criticism or praise can make or break an artist’s career.

At the time, Cardi B’s marketability lived in the questionable corners of social media, where her outlandish Instagram posts had landed her a spot on MTV’s Love & Hip Hop: New York. Apparently, no critic of real clout took Cardi B’s music seriously. To them, she was an ex-exotic dancer who spoke poor English, who couldn’t rap, and who’d earned a small spotlight on reality TV only because of her cosmetic surgeries. At least that’s what Ebro and Rosenberg told her on air.

I’ve watched the entire 41-minute interview on YouTube. It’s uncomfortable.

Ebro and Rosenberg pepper Cardi B with questions about her body parts, her former career as a stripper, and her supposed lack of proper English. To her credit, Cardi B responds patiently, exuding conviction in her thick Bronx accent. When they start discussing her songs, Ebro grunts disapprovingly. Then comes the most damning comment of all. Ebro declares that when it comes to her raps, “We gotta work on that.”

Ebro’s diss could have ended Cardi B’s career right then and there.

But it didn’t. Cardi B wouldn’t just prove these incumbents wrong. She wouldn’t just make it in their world either. She would remake their world, and in record time.

In 2017, almost one year to the day after the interview, Cardi B released her first major-label single, “Bodak Yellow.” The song garnered critical acclaim, winning various awards, including Single of the Year at the BET Hip Hop Awards and three nominations at the Grammys. Many critics now consider “Bodak Yellow” one of the most influential hip-hop songs of its decade.

By 2018, Cardi B had broken Beyoncé’s record for the most simultaneous top-10 songs for a female in her category. By 2019, Cardi B’s debut album had made her the first female solo artist in history to win the Grammy Award for Best Rap Album. By 2021, critics mentioned her in the same breath as the greatest female rapper of all time, Lauryn Hill.

Less than a decade into Cardi B’s music career, and she already has more sway over hip-hop than the guys who dismissed her.

That’s what happens when someone disrupts an industry—when the rules everyone else must follow seem, somehow, not to apply.

When you look up lists of “Greatest Rappers of All Time,” you’ll likely need to scroll a while on any list until you find a female. Usually the first woman you’ll see on the list is Lauryn Hill, from her one studio album in 1998. Since then, if a woman wanted to make it in the rap game, she needed to curate an invite from a male incumbent: Da Brat had Jermaine Dupri; Nicki Minaj had Lil Wayne; Lil’ Kim had Notorious B.I.G.

That’s why Ebro never saw her coming, a woman who didn’t attached herself to a man’s name. A disruptor who created her own door, disrupted someone else’s universe, then left with all the trophies.

SUCCESS IS A PITFALL

The better you are at something, the more likely you are to become the Ebro (aka a doubter) of someone else’s innovation tale. Why? Because you’ve already achieved success one way, and nothing kills innovation like past successes.

Think about how hard leaving success is for you: You know how to land the financing you want. You know how to please the customers in your industry. You understand how to arrange the IT so everything runs smoothly. You’re efficient, so in your career, you’ve built an easy shortcut to what you want, and it’s hard to unsee it.

In a scene from the movie Pearl Harbor, two officers discuss how safe the military base in Hawaii is. One of them runs through all the reasons their stronghold is impenetrable. But Admiral Kimmel isn’t buying it: “The smart enemy attacks you exactly where you think you are safe.” Simple but profound. If you start to feel safe like Ebro, you’re in trouble. He had everything to lose and nothing to gain by thinking differently, so he didn’t bother. He thought he knew exactly how hip-hop worked based on proof from the past.

But past proof doesn’t guarantee future success. And companies (especially ones dedicated to excellence) make this exact mistake.

So what do you need to know to make sure your past successes don’t hinder your future?

1.   THERE ARE NO BEST PRACTICES. Don’t assume that a solution that worked in the past will work again; think of fresh ideas in every scenario.

2.   DON’T BE AN EBRO EXPERT. Avoid being defensive about your expertise; instead, take on a rookie mindset.

3.   DON’T FALL INTO THE RUSSELL WESTBROOK TRAP. Like basketball player Russell Westbrook, it’s easy to let past successes define your identity. But this is a trap that hinders your ability to succeed in the future.

4.   GO FROM 100 TO 0 IN SECONDS. Be willing to start back at the beginning. At zero. As a novice.

Let’s dig in.

THERE ARE NO BEST PRACTICES

On the outside, the top management consulting companies rely on supposedly smart, proven tactics to help their clients. After I moved into management consulting at Deloitte, I started coming face-to-face with this one idea frequently: “best practices.” With best practices, you find successful tactics that have been used by others and then help other clients apply them to their own companies. Top firms like McKinsey, BCG, and Bain all use this strategy of repackaging what once worked elsewhere. With a long list of clients and a storied legacy, Deloitte had many of these so-called best practices.

So that’s what I offered on all my projects, to all my clients—at first.

But not one of my original initiatives based on best practices ever succeeded. In fact, most of them didn’t even attract enough initial interest and traction to properly fail.

One of my early clients was a financial services company that needed to revamp its website and end-to-end digital customer experience. They were looking to shake things up, and they wanted an innovative way for their customers to understand and transact with the company’s products and services. I wasn’t exactly a customer experience expert, so I did the logical thing: I went through the playbooks Deloitte had issued to other clients to address similar issues. I lifted a success story and then repackaged it. (I literally used the same PowerPoints, processes, and steps.)

Did it work? Not even close.

This client wasn’t even interested in trying my “new” idea.

The same story happened with several of my other beginning clients. So, it didn’t take long for me to change directions, to start looking at every project as if it were a new beginning, a one-of-a-kind universe with no rules and a blue-sky opportunity. Unsurprisingly, clients started responding, projects started rolling, and innovation started occurring.

Now I’m able to crystallize exactly what Cardi B knew all along: There are no best practices.

DON’T BE AN EBRO EXPERT

There’s a fine line between having excellence and being an expert, but the subtle difference lands you on opposite ends of innovation. Excellence is the pursuit of being best in every situation—something every hardworking, ambitious worker should aspire to. But being an expert with supposed “best practices”? I’ll pass.

Zoom out and picture just how Cardi B accomplished what she did.

Before she touched a microphone, she developed a loyal following using social media in the most unconventional way. While other influencers were curating their perfect lives, with filters and aesthetically pleasing grids on Instagram, Cardi B swam in the wrong direction—she went raw, authentic, and unapologetic. She became the anti-Instagram, on Instagram. She documented the struggles, the past, and her insane adventures. She stood out in the best way possible. She broke all the “best practices” and had no “expertise.” And that’s exactly why people loved her, and how she landed a coveted spot on Love & Hip Hop.

But Cardi B wasn’t about to get stuck in this one success. After her Ebro in the Morning appearance, she declined her third-season appearance on Love & Hip Hop, going all-in on her music. Seven months later, she had a number one single. It was a pivot for the ages.

She knew not to become the “expert” that Ebro thought he was.

Here’s my question: How often do we brush aside the Cardi B moments in our own lives and careers, and opt, instead, to be the Ebro expert?

Consider his arrogance, his matter-of-fact certainty that Cardi B wasn’t going anywhere in rap, and ask yourself if you’ve done the same. Have you dismissed the intern because their idea seemed just a bit too green? When’s the last time you internally laughed at someone else’s new process because you knew, from experience, it simply wouldn’t work?

Ebro had proof. He understood hip-hop. He’d interviewed the greats, and he’d been there at big moments in hip-hop’s history. So he felt safe. And that’s exactly why he was disrupted. But what if we approached every day like Cardi B instead of Ebro? What if, even within your own specialty, you approached it as if you knew nothing? That’s the challenge—to walk into the office, and despite years of best practices and prior wins, you walk in as a rookie, a first-timer, who is all-ears for new ideas, who is not just trying to re-create yesterday’s success, but who’s galvanized thinking about a new future.

That’s the Cardi B challenge.

I have a simple hack to use, one that can help you determine if the Ebro mentality has taken up residence in your own mind. Simply ask yourself this question: Am I defensive about my expertise?

•   If you’re an accountant, and you’re defensive about the software you use, you’re getting close to the Ebro line.

•   If you’re the software engineer who knows that the Agile method is “always superior,” you’re setting yourself up for a Cardi B disruption.

•   If you’re a project manager who understands exactly how to motivate a team, so you do it the same way over and over again, maybe it’s time for a new practice.

Defensiveness is the critical component that Ebro was carrying with him. It blinded him to the danger he was in. He felt comfortable, reassured, safe. Yet, he was anything but safe.

If you’re utterly certain about how to accomplish a project, which software to use, or what methods are superior, to the point that you’re defensive of those practices, you’re ripe for an Ebro awakening. Cardi B never had time to defend her expert status. The moment she did well in one arena, she disrupted herself.

By definition, an expert is someone who knows how to do something well based on experience. Disruption, by definition, revels in the new, dabbles in the upside down, and dares to think differently. Bold Ones are courageous enough, and willing enough, to bounce from one idea to the next.

If you want the same haircut, you don’t want a disruptor; you want a process follower. You’ll get exactly what you had last time. But if you want a fashion-busting, trend-leading style, you’ve got to look your hairstylist in the eye, trust what will happen, and leap.

If something’s “standard” or “best practice,” you might as well say, “We’re on the downturn.” If you perform your design job the same way you did 10 years ago, you’re likely about to be replaced. If you project-manage your team using the same processes you used five years prior, your teammates may not be listening. If you approach problems with the same mindset you accessed five minutes ago, I promise you, you’re starting to become an expert, ripe for disruption.

Don’t be an Ebro expert.

DON’T FALL INTO THE RUSSELL WESTBROOK TRAP

There’s a reason we all have such a problem letting go of old tools, methodologies, and processes. They worked.

We’re all addicted to success. Failure feels awful, while winning feels good. We’ll take a quick, small win over a giant risk any day. In fact, we’re so excited about the feeling of winning, we’ll sacrifice true accomplishments for a mirage of it. Don’t believe me? Look no further than NBA player Russell Westbrook.

Westbrook is a former MVP and the triple-double king of the NBA.² He had 194 triple-doubles by the time I started this book. No other basketball player can touch that statistic.

He’s one of my favorite athletes to watch, playing with incredible intensity, barreling down the court with electrifying dunks. Watch him play, basketball fan or not, and you’ll think, He’s the best on the floor. And he’ll likely dazzle the commentators with his stats.

But those stats never translate to wins.

In fact, teams can’t get rid of Westbrook fast enough. He’s been moved from Oklahoma City to Houston to Washington to Los Angeles—all within three years.

The problem isn’t that he’s not good. The problem is that he was good. His style was successful for the Oklahoma City Thunder. There he gained such a badass reputation that he hasn’t been able to let go of his old style. He isn’t willing to try something new that will tarnish his stats. The risk is just too great. Apparently he’d rather lose games as long as his numbers tell him he’s doing well.

Overall, his identity is wrapped up in triple-doubles. It’s like he’s getting style points for his breaststroke but he’s getting lapped in the pool. I call this the Russell Westbrook Trap—an unwillingness to let go of identity.

One of my mentors and favorite ex-partners at Deloitte, Paul-Marc Frenette, used the following words when talking with oil executives. He’d tell them—to their face—you guys are so “fat, rich, and lazy that you can’t see the future.” (Yeah, Paul-Marc was a gangster.)

Individuals and entire companies fall into the Russell Westbrook Trap. Old bands keep coming back for “reunion tours.” Once-retired athletes keep coming back for an encore. Movie studios get one hit, and three sequels later, we’re seeing commercials for Fast and the Furious 34.

And the more successful you once were, the nastier the teeth of your own personal Russell Westbrook Trap.

In a now-famous paper, researcher Karl E. Weick identified firefighters who died while holding onto their tools. Tragically, in the fires he studied, Weick observed that many firefighters would have lived if they’d simply dropped the bulky equipment they were carrying. Instead, they ran holding weighty hoses, axes, and gear, which slowed them down so much they couldn’t escape the engulfing flames. Weick concluded his paper by proposing that the tools—which the experienced firefighters had once successfully used to put out other fires—had seared themselves into the psyche of the men to the degree that they considered those tools as extensions of their self-images.

Spielberg, one of the greatest filmmakers of all time, once got so mad that a new web-only studio—Netflix—was sweeping the Oscars that he suggested that the Academy shouldn’t allow Netflix to compete against him. Even the GOAT³ filmmaker had become a bit “fat, rich, and lazy.”

The more successful your former tools, techniques, and ideas were, the more they become ingrained in your own mind, until, eventually, you see these as part of you. To stop working the way you did previously would mean you’d become someone new (or so you think).

LET GO OF STATUS

Our identity is built not only upon the tools and methodologies of yesteryear, but on the status we receive from previous accomplishments. When others congratulate us on our projects, we want to repeat the action. When we work hard to ace a class, our GPA reflects an uptick, and we want to repeat the action.

Status is embedded in our DNA. When we win, others notice, we notice, and our status with our coworkers, our company, and our industries rises. Our brain says, That feels good. In his 1992 Class: A Guide Through the American Status System, Paul Fussell discusses how losing your current level of status is one of the greatest fears for any person in society. Russell Westbrook may not be winning games, but he does get to hear “triple-double” all the time. Giving that up isn’t easy.

In your own world, you must proactively decouple your psyche from the status that is so alluring, particularly as you gain success. When I say “proactively,” I mean it. If you want to practice disrupting yourself, then start by intentionally reducing your own status.

I assume you’re excellent within your career. Likely, you’ve earned some sort of accreditation that suggests as much: MBA, PMP, CFA, CPA, etc. These sit on our résumés, on our LinkedIn descriptions, and on our bios. They may be appropriate in those settings, but don’t let these letters attach themselves to your identity. Personally, I try to prevent having any designations beside my name. It’s just too easy to carry them as if they defined me. Plus, they intimidate others, or, at best, repel great ideas. If Ebro had been less of an expert and relied less on his own status, maybe he would have been the one to launch Cardi B’s hip-hop career. Instead of mocking her, he might have recognized that she was the next big thing.

Here’s the antidote to the identity and status temptation of the Russell Westbrook Trap: Get low on the totem pole. Whatever’s laying hold to your identity, lose it. Let go of the ego, and with it, all the status. You may have found out how to master yesterday’s methodologies, last year’s software, or your company’s politics. But those are stats. Are you—and your coworkers—winning games?

Status is alluring. Success lays hold onto your identity. To keep yourself free of the Russell Westbrook Trap, here are a few tactics:

•   PLACE YOURSELF IN “LOWER-STATUS” SITUATIONS. Come off the bench. Clean the floors. Be the assistant. Fetch your team’s coffee. Be the team’s driver. Take the middle seat. Take the bus. Greet the members of your team at the door. Deliver them lunch. Wherever you are on the totem pole—whether intern or CXO—go down the pole. There’s a heap of benefits to these practices—if nothing else, you’ll learn that your identity isn’t wrapped up in hierarchy.

•   SUBSTITUTE STORY FOR TITLES. Look, I get it. You worked hard for that degree (or that title in your company), but is that really the key that will unlock future innovation in your field? Try this instead: The next time you introduce yourself in the office, at a work lunch, or at a conference, drop the title, the school, or the big-name company you worked for. Instead, tell a story about what you (and optimally, your team) did. Stats are cute. Wins are hot.

•   LISTEN TO THE NEW KID. What if Westbrook were willing to watch younger players—and even learn from them? When you detach from your learned expertise, letting go of your identity, you’ll learn something new. The next time the intern, the inexperienced, or the hotshot shows up with a unique, even crazy, idea, listen. Sure, they may be green. But maybe they’re onto something.

•   WATCH THE MARKETPLACE. Every day, innovators are shipping hot software, new services, and hip products. Sign up, dabble on the fringes, and tinker in the latest. This will keep you inspired and fresh. There are a few hot communities where hip innovators connect to share their latest and greatest—one of my favorites is ProductHunt.com.

GO FROM 100 TO 0 IN SECONDS

Maybe you’re thinking, I’m not an expert at all. Well, you’re probably not tempted by the Russell Westbrook Trap (yet).

But the question for everyone—from the experienced to the novice—is simple:

Are you willing to constantly start at the bottom, at zero?

Disruption requires execution into the unknown, a faithful leap into something that you’ve never tried before. Baby steps—like listening to others and letting go of ego—are just that, baby steps. But when it comes time to jump, like Cardi B, you’ve got to be willing to be at the bottom. If you want to invent an entirely new product, you must be willing to know nothing about it. To create a new software program, you must experiment. To pioneer a new workplace culture, be willing to be wrong, a lot.

Incremental improvement is easy—you get to build on a foundation that already exists. But to start a company, build a new product, pitch a client in a new way, or forge a new line of business, you’ve got to be willing to start at the bottom, at nothing.

No one knows this better than producer Jermaine Dupri.

In 1990, Dupri noticed two kids, both named Chris, at Greenbriar Mall in Atlanta. They seemed like they were already celebrities—girls were commenting about their looks, and they had an aura of fame about them. He watched as they went up to a cookie counter, and the young ladies went wild for them, even giving them free cookies. By this time, Dupri was in the music industry, but he’d only collaborated with women, and he’d obviously never heard these kids sing, nor did he know if they even could. He’d never worked with men—not that they were truly “men” yet—they were only 12 and 13 years old. Still, Dupri did know these Chrises had some sort of “it” factor. So he gave them his number and told them he wanted to make them stars.

Less than two years later, they went multi-platinum under the name Kriss Kross.

Then Dupri did it again with female rap group Xscape, whose first album also went platinum. Next stop? Da Brat: platinum. In 1995, Dupri collaborated with Mariah Carey on a little song called “Always Be My Baby”: triple platinum. Usher, Destiny’s Child, Jay-Z, Lil’ Bow Wow, and Weezer all have one thing in common—Dupri.

Dupri talks about going from 100 to 0. Every time he scoops up a fledgling artist or collaborates with a star on a new song, he never views the experience as something to which he’s bringing expertise. Instead, he views it as his opportunity to start brand new, from the ground up, reducing himself to zero. While everyone else is trying to build on where they were yesterday, Dupri actively looks for the opportunity to start over. That mentality has allowed him to continually rethink hip-hop and R&B. Now he’s going into vegan ice cream (true story). Will it work? I don’t know. And that’s the point.

Staying at 90 and trying to move to 100 is the easy choice. Relying on best practices is the cop-out. Bold Ones take the risk, and they’re willing to be a rookie in a new endeavor. While everyone else wants to go from 0 to 100, Bold Ones have the guts to attempt Dupri’s 100 to 0.

An ancient Haitian proverb says, “Behind mountains are more mountains.” There’s always a new mountain available. If you haven’t found the top of one yet—start moving. But once you get there, recognize there’s another one out there, and to get to that one, you must descend into a valley. To find the new, you must constantly leave the high to embrace the low. Are you willing to travel the valleys, to restart, to reinvent, to be a novice, to fail, all the way back to zero?

I think there are three ways we can embrace this 100-to-0 mentality.

1. IDENTIFY YOUR NEXT MOUNTAIN

Bold Ones are willing to reduce themselves to zero, only because they have that next mountain in view. Dupri doesn’t drop down to nothing just for the sake of it—he’s eyeing the next prize. And every mountain is a newer, bigger one.

Identifying where you want to go is key. If Westbrook would visualize winning, he might be willing to give up his status as the triple-double king in exchange for a championship. So before you decide to dive down to zero, ask yourself, What’s worth going from 100 down to the bottom?

I get to speak with a lot of people across the globe who want to be doing something different than what they’re doing currently. They want to dabble in something new. They’re in accounting, but they want to be in blockchain. They’re financial advisors who are really storytellers. They’re CXOs at traditional firms, but they have wild ideas about their industry. They all tell me they desire to do something different. I tell them to make it concrete, real, to paint that next picture clear in their head. Dream up that mountain.

2. INCH TOWARD THAT MOUNTAIN

Actively identify where you want to be; then get a little flirty with it. You don’t need to change your job tomorrow, or present your hot new idea straight to your firm’s CEO. Instead, dabble, play, experiment. Give yourself some small wins. Later you can go bigger.

Start by actively learning skills exactly in what you’re interested in. Today there’s a new skill site for just about anything. If you’re a basketball player who wants to code, go to CodeAcademy.com. If you’re a coder who wants to learn basketball, go to MasterClass and learn from Steph Curry. Likewise for almost every imaginable skill, hobby, or idea—someone’s started the community for it already. Hop on board.

There may be other small moves you can make today—maybe you need to save up financially so you can start your own firm. Perhaps you want to move up in your company and you need a mentor. Take some action, anything, every week toward those goals. Be willing to work for free on nights and weekends to learn a new craft. Skip eating out to start putting some money away to save up for your own company. Whatever you must do, inch your way up the mountain.

3. USE TRAGEDY TO START OVER

I find one of the easiest and most practical ways of going from 100 to 0 is to seize moments afforded by tragedy.

When my father passed, I had to take over his accounting clients—starting at zero.

When the pandemic hit and all my speaking engagements were canceled, I called my team and asked how we could re-create the best livestream experience anyone has ever seen—starting at zero.

When you’re looking for somewhere to start with disruption, look no further than your next tragedy or upset. These are the moments when you can ask yourself, nearly risk-free, “If I were starting from zero, how would we start this?”

EBRO’S ERROR

If you walk into Ebro’s studio, you’ll catch a laid-back, T-shirt–wearing, hip-hop aficionado, a tattooed host who says what he thinks, plays what he wants, and rubs elbows with the gods of the hip-hop universe. A true rebel in loud, irreverent tones. This man, you’d think, answers to no one. The same guy that was in the studio the day Cardi B walked in.

But then, even with all his rabble-rousing, Ebro had become a slow-moving has-been incumbent, with old tools, outdated practices, and stale ideas, whose opinion was ultimately dismissed by someone he was trying to wave off, someone who would change his universe. He was the gatekeeper of a world he didn’t understand anymore. Once upon a time, his mindset had perhaps forged the path from zero to hero in the rap game. But by sticking to his guns and traversing the one path he knew, he missed who would become one of his industry’s greatest.

Copycatting what worked before doesn’t work.

Be willing to do what’s new, even if what you’re doing is currently working. Go from 100, to zero.

SECRETS OF THE BOLD ONES