We asked Chris Webby, a 29-year-old independent MC from Norwalk, Connecticut, who made his first appearance on our pages in 2009 ("Who's Back"), to share the most valuable mistake of his nine-year recording career. Instead, he wrote a five-rule guide to achieving success as an independent artist.
I've made plenty of mistakes on my journey as an independent hip-hop artist. In the long run, they've made me a better rapper and businessman, but they also took a toll on my financial and overall success trajectory in the process. But that's the game. Even though I would consider myself a young veteran, I still learn new things all the time.
Below is my five-rule guide to achieving success in this independent battlefield that we call home. A lot of advice I was given early on in my career went in one ear and out the other, but hopefully, some of these suggestions sink in.
Rule No. 1: Develop a Bullshit Detector
Time and time again, I've made the mistake of putting faith into the wrong people and it dramatically affected how things panned out for me in the earlier portion of my career. People lie. People embellish the truth. If you don't know someone through someone, there's a high probability that they're full of shit. That's just the nature of the game, so get used to it. If you keep waiting for everyone to do what they promised they'd do, you might end up missing other opportunities and losing momentum. My new rule for everyone I work with is "under-promise and over-deliver." And always have a backup plan.
Rule No. 2: Keep an Eye on Your Money
Trust only goes so far when the cash starts rolling in...or stops rolling in. You must be aware of where every single penny goes. Get your business account(s) organized and streamlined. Earlier in my career, I had no idea how the money side worked. I was happy and content with being the rapper and solely focusing on the music and the shows. I know it's an exciting time when you catch some buzz for the first time and all your tireless hours of perfecting a craft are all of a sudden validated, but don't let that distract you from the boring business stuff. It sucks, I know, I hate math myself. But if I had been learning about and paying attention to it the whole time, I'd be a richer man today.
Rule No. 3: Constantly Reinvest in Yourself
This is a rule I've followed since the beginning, and it's been a staple of my success and survival all these years. The majority of what I make goes directly back into the Chris Webby machine and keeps the gears grinding. If you're an independent artist with no financial backing, it's imperative to stay active and productive. Keeping a rap career in motion isn't cheap. You're basically betting on yourself. As you begin to stack more chips, you'll have the choice to either blow it on things you don't need or make bigger career moves. The latter is obviously the correct decision for long-term success.
Rule No. 4: Work Hard as Fuck
You're the boss. It's on you to step up and do what needs to be done if need be, whatever the situation. You're indie and it's on you to perform at a level that allows you to compete in the same arena as the artists with the big label money. Don't be lazy. I approach every day with the mindset: "Based on what I've done today, would I promote myself or would I fire myself?" That mindset has made me grind at maximum capacity the past couple years.
Rule No 5: Be Cool to People & Remain Humble
Don't forget where you came from and don't become an asshole when you first attain some success. Nobody likes that Mr. Cool Guy attitude. It comes off as rude, juvenile, and insecure. Just be yourself. Being an independent entity in this business means you'll probably be touring a lot of the same markets too; that's your bread and butter. If you're a dick to fans, venues, or promoters it will affect your career in the long run. That goes for your crew as well; keep their behavior in line because it directly reflects upon you and how you're perceived by those around you. You want to be building relationships, not burning bridges.