Why Playing It Safe Can Be Risky

take risks


Last time on The Ten Laws of Indie Success…


…We covered The Law of Indie Success #2 Invest In Yourself. We looked at how Wiz Khalifa harnessed his self-belief early on in his career  and invested in his craft. He went on to establish an unbreakable relationship with his audience to create an irresistible brand which has lead to numerous brand partnerships and phenomenal success.


This week we take a look at the huge risks Sean ‘Diddy’ Combs has taken throughout his career to set new benchmarks in Hip Hop culture.


Law of Indie Success #3: Take Risks


There’s a saying, “Take risks: if you win you will be happy; if you lose you will be wise.” By playing it safe you may make money but you will never get paid for being a ground-breaker or trendsetter. By getting creative and pushing the boundaries artistically, you put yourself in the unique position to create a niche of your own.



Are you playing it safe and doing the same thing that everyone else is doing?



There is a ‘rapper myth’ which insists that we believe all rappers are from the streets and become entrepreneurial by selling drugs – almost a rite of passage for emerging Hip Hop artists. This couldn’t be further from the truth. Risk taking and entrepreneurialism is a mindset. A risk taker is someone who calculates risks and knows when and how they will make a return, at times taking a complete leap of faith. The greater the risk, the greater the reward, but high rewards come about as a combination of risk taking and intelligence.  It’s the difference between gambling your own money on your music career, or waiting to be signed by a record label or some other investor. Entrepreneurs tend to show a type of impulsive risk-taking that allows them to seize opportunities under stress in a way that most people can’t. An entrepreneur’s outlook is that you have to take a risk to find out if your idea will succeed.




Sean ‘Diddy’ Combs dropped out of Howard University after earning a position as A&R at Uptown Records where he had been an intern. After achieving success with R&B sensations, Jodeci, he grew increasingly conceited and was sacked from the role. On leaving Uptown Combs took a risk by taking Mary J. Blige with him, an artist Uptown Records were unsure of what to do with. He soon set up Bad Boy Records, producing The Source Magazine’s unsigned hype winning rapper Biggie Smalls along with a roster of other unknown artists.


Are you flexible enough to adapt?


Built into taking a risk is the possibility of loss. The first step then is to know the market you are working in, followed by trusting your intuition. No matter how unsure you are about the risk you are taking you must have faith in your decision and follow through with a steady plan.


Following the untimely death of the most successful artist on the Badboy label Biggie Smalls, Diddy made the transition from Producer to Rapper by recording “I’ll Be Missing You” featuring Faith Evans and 112 as a tribute to his best friend.  In 1998, the song won the Grammy Award for Best Rap Performance by a Duo or Group. With worldwide sales of over 8 million, including shipments of 3 million copies in the United States and over 1 million in both Germany and the United Kingdom, the song has become one of the best-selling singles of all time. It is currently ranked the 94th biggest song of all time according to Billboard.


“Make sure the odds are in your favour. And to do that, make sure that you are a master of that category that you are investing in, or you are trying to start a business in,” said Combs. “Any business I get into, I go and I do the proper studying and I do the research to make sure I thoroughly understand that business.”


By taking calculated risks in a variety of business ventures Sean ‘Diddy’ Combs has become the richest man in Hip Hop, worth $735 million. Diddy has a deal with Diageo’s Ciroc vodka that guarantees him a split of the proceeds if the brand is ever sold. He also owns a stake in clothing lines Sean John and Enyce, alkaline water brand Aquahydrate, new tequila DeLeon and multimedia network Revolt. Diddy founded Revolt TV with a renewed focus on music.


Make Sure The Odds Are In Your Favour


Book a 30 minute consultation to plan a strategy for your music brand. Find out how to…


·         Create your own niche

·         Remain flexible

·         Take calculated risks


Next time on The Ten Laws of Indie Success… The Law of  Indie Success #4 Engage Your Audience


Deb McKoy