Chess Not Checkers: How Kevin Webb Manages From Start-Up to Stardom

As fans, a rapid rise to fame is the type of energy we all love to witness. Who doesn’t enjoy the story of the American Dream, where someone matches talent with drive and ascends to unfathomable heights? That dream lives inside all of us who envision our wildest imagination becoming reality.

A Boogie Wit Da Hoodie is living that dream in front of our eyes. Seemingly overnight, he went from having a buzz around the Bronx to becoming a chart topping hitmaker. Success of that magnitude is never a coincidence, and anyone who reaches stardom by the age of 22 needs all the guidance they can get. What’s necessary is a coach, someone with enough experience to help an up-and-comer navigate new levels of fame. A person patient enough to advise with a hands on approach, while staying out of the way. For A Boogie, that person is Kevin Webb.

Kevin Webb is a well-known manager in hip-hop. It was with his help that Fabolous grew from a Brooklyn rapper buzzing locally to a chart-topping international superstar, and eventually a walking business with endorsements and partnerships. Webb has the special vantage point of seeing the rap game grow through two golden eras: the first being the mid-to-late 90s when rap took over mainstream America; and the second being the present in which the internet has put unbelievable power in the hands of the artist. The result is a deep knowledge of bootstrapping one’s way to fame through putting foot to pavement, and spreading the music city to city; combined with using the internet to create a market for an artist and leveraging that market to set the price when labels and brands come calling.

Webb used his unique mix of experience and natural ability to manage A Boogie’s growth from a kid with potential to a household name, but his tactics are applicable to anyone charting their own course to success, no matter the industry.

Own Your Path

As a freshman in college, Webb knew he wanted to manage artists and eventually start a record label. After being told that he should start promoting to make the proper contacts, he met DJ Clue. Webb also had a relationship with a young hungry rapper from Brooklyn. That rapper went by the name of Fabolous, and after Webb introduced Fab to Clue, the rest was history. They entered the game at a key transitional period. Biggie and Pac had tragically lost their lives, as rap was becoming ingrained in the pop cultural identity of America. A lot of money was being made, but there was an impeding changing of the guard for the new millennium.

“I was in high school wanting to manage, at 16 or 17. As a freshman in college, I wanted to start a record label. I was told I should start promoting parties to make contacts. I met DJ Clue and knew Fab from the projects. I connected Fab with Clue and that was the start. While going to a business school, they told me that by picking up business management I would be able to spread out in all areas. Understanding my path early on really opened my mind up to traveling. I let God guide me the whole time.”

When you feel it in your heart to pursue a vision for yourself, you’ve got to take responsibility for designing your life. We all have a path to travel, but many people are afraid to walk into the dark and find their light when the road isn’t laid out right in front of them. Webb understood that while he didn’t have all the answers, he was meant to be a part of the next chapter of hip-hop’s history book. He owned his path.

Rick The Ruler

Embrace Change and Get Creative

Webb would go on to achieve massive success with Fabolous. As we all know, Fab eventually became responsible for some of the biggest hits of the early 2000s, solidifying his star power and cementing his position as a respected lyricist. However, times do change and Webb eventually became an OG in a sea of new hopefuls ready to make their mark on the industry. Enter A Boogie Wit Da Hoodie, a young talent who was making waves in NYC just like Fab did two decades before. Webb saw history repeating itself, and stepped in to guide A Boogie through a changing music industry, adjusting to a new business model due to streaming and social media.

“The labels have an old system of thinking. They have a delayed reaction. They want to see a record build traction before dropping a project. In the past, you might push one single for five to six months. Nowadays, that shit has to hit in a couple months. Everything is sped up. You can’t wait and try to work a record. In my experience now, it’s strategy and time management.”

When your industry is in the middle of a massive shift, it’s time to get innovative as new standards are being set across the board. Too often, people count their trophies instead of focusing on the new season. Kicking your feet up on prior accomplishments is the easiest way to fall off. Creativity is the father of innovation. In order to stand out in any field, you’ve got to raise the bar with your work. How can you raise the bar without being knowledgeable? Like Webb, you should always have your finger on the pulse of your industry so that when change is on the horizon, you can adapt and set the play up for new wins.

Leverage Past Experiences for New Goals

Webb launched his management career during an era when artist development was the norm. As a veteran, he doesn’t see the industry placing the same value on artist development. A smart person knows that a lack of industry focus on a skill set doesn’t make it irrelevant. Now, Webb’s 20+ years of experience provides him with a product that’s hard to find.

“Artist development is non-existent. It’s all about the evolution of the manager. Managers are going to have to evolve or they won’t survive in this space. Artist development is a big space that has for lack of a better word, been forgotten. Me? I develop the artist and distribute worldwide. As streaming evens out and the lava cools, it’s a great time to enter and stake your claim. Look at Steve Stoute and United Masters.”

Rick The Ruler

Webb saw a space to provide a service to artists on the brink of a big break, but who lack the development and access to resources. Labels want artists with huge social followings, so they can quickly capitalize off of an audience without spending money to build it. Webb plays the space in between; he leveraged his past experience to fill a void and create another source of income. Through Webb Music Pro, he offers online management using a team of top industry professionals including entertainment lawyers, personal managers, bloggers, and radio promotion specialists. The lesson here? The game doesn’t change, just the players in it. Identify how to make your old experiences relevant as your industry evolves, and you’ll always sustain value.

Maintain Focus Through New Levels of Achievement

New levels bring new devils, and it’s easy to get distracted once that first big taste of success comes knocking. As his manager, Webb has watched A Boogie climb from a local sensation to sharing stages with Drake. Needless to say, A Boogie secured major bags in 2017 and along with that comes new temptation. As his stardom rises every year, Kevin has to help him navigate through it all.

“It was really like deja vu. Dealing with Fab and learning from those mistakes just made me stronger for A Boogie. You’ve got to be able to relate to the youth. There is no generation gap. He’s 22 and I’m 40. We used to kick it like big bro-little bro more than father and son. At the end of the day, he respected my seasoning in the game. I let him enjoy himself, he copped so much jewelry. I tell him to chill, but I’m not going to OD. I try to be better at having him save and advising him on economics, real estate, and assets.”

Always look at yourself as a business; you re-invest in yourself. The objective is to keep winning. Nobody wants to be the person bragging about what they used to have, but couldn’t keep.

Control Your Ego

Whether you fool yourself into thinking you can’t lose, or get so down on yourself that you forget how bright your light shines, an unchecked ego can lead to failure. In Kevin’s case, his success depends on his artist’s success. That means his job revolves around ensuring someone else is happy and ready to work, which could agitate the ego sometimes. Management is just like coaching, you don’t get credit for the wins, but you bear responsibility for the losses.

Rick The Ruler

“You definitely have to check yourself. You’re on call 24 hours a day. If your artist calls you and you don’t pick up or too much time passes, it could be a bad look.”

We can all name several times when work required us to check our ego at the door. Some may say it’s selling out, but in reality it’s just the nature of the beast. No one starts out as the person in charge. While you earn your stripes in whatever industry you choose, controlling your ego is the key to longevity. Webb’s path to music industry success is marked by a common thread of staying humble. Humble enough to submit himself to the process, embrace change, avoid distractions, and check his ego. Imagine what you can accomplish by implementing the same habits. Get to it, the world is waiting to see you win.