Kardinal Offishall’s Five Reminders for Aspiring Entrepreneurs

Cormac McGee
Inside the Music Den
5 min readJul 29, 2016
Shoutout to The Come Up Show for the photo.

This week Startup Grind TO hosted Canada’s original hip hop ambassador Kardinal Offishall for its latest fireside chat. Kardi touched on many subjects, from music and technology, to the pains of social media, diversity in Canada and shaping yourself as a popular brand.

Listening to him, it’s clear Kardinal’s success has come because he refuses to stop hustling. His voice was raspy from playing back to back shows, after which he gets little space in his bed because his three kids want to share it with him and his wife. He had been shooting a music video with Neon Dreams earlier in the day, all while planning and promoting his Karibana House Party coming up on Sunday.

Kardinal’s experiences are transferable across industries, especially as a Canadian in a field where — when he started out in the 1990s — players from the north weren’t taken seriously. He dropped a lot of knowledge at Startup Grind, and below we’ve distilled it into five key reminders for aspiring entrepreneurs. (If you want a full recap of the event, check our live tweet session.) You may have heard these messages before, but not like this:

Don’t Get Caught Up in Your Hype

“Artists care that their show is sold out tonight, but what about six months from now? A lot of people get caught in their own hype, they don’t evolve then all of a sudden crowds are booing them and they don’t know why. The next time you see this performer it might be at Home Depot showing you where the lumber is. We always ask ‘What happened to this person?’ That’s what happened to them. They fell off.”

Before Prime Boys and OVO made it the 6, Kardinal’s “Bakardi Slang” popularized T-dot (as in Tee dot Oh) in 2001. This was one of Kardi’s biggest hits, especially in (insert your name for Toronto here), and people were loving it. But one hit is rarely enough, he needed a sustainable source of income. That’s why he started working with Universal as an A&R, even though — according to him — working for a record label as an artist is like putting on a Satan mask.

Watch What’s Going on Around You

“When some artists tour, they stop in the city, play their show, party and move on. In each city I went to, I made sure to do radio shows, meet promoters and learn about the scene there. People need to gather a real database of who’s listening to them and what they like.”

Kardinal credits much of his success to his effort and ability to watch what other artists around him were doing. “I was looking for what was working, but more importantly, what wasn’t, so I wouldn’t make the same mistakes.” In the 1990s Kardi, and a handful of other Canadian rappers—such as Saukrates and Choclair—literally carved their own paths. There was no system in place for growing hip hop talent in Canada. In the startup world, a support system is slowly being built — coworking spaces, meet ups and socials are easy ways for you to learn from other’s mistakes. But if you insulate yourself, you’re likely to repeat them.

Set Specific, Meaningful Goals

“I used to grind in the studio and make three weeks worth of songs, hoping that one of them would get big. After I started working at Universal I realized that doesn’t make sense, it was a waste of energy. I could go in and focus on making three really good songs and have the same effect on my career. There’s no point making a bunch of songs and just hoping one sticks.”

Rappers like Lil B and Gucci Mane have used the quantity over quality strategy to carve out successful careers, but for most that won’t work. If you have one great product, few people will likely care about the 25 other decent ones you made.

On the flip side, too many of us write goals down just for the sake of it. It’s an easy exercise that makes us feel like we’re working towards something, even if we haven’t really put serious thought into what it is. Setting big goals only works when you’re conscious of making steps toward them each day.

In Canada, You have to Tangibly Prove Your Worth

“In America, an awesome idea pitch can get you a big cheque. In Canada, you might get invited to the Christmas party.”

Like hip hop in Canada, most other fields are slowly growing to be more supportive of startups — “slowly” being the key word. The fact is there’s not as much money to go around in Canada as there is in the United States, especially when it comes to venture capital. People won’t invest in your idea here because they like it, but because you’ve shown results. We’ve had a number of people pitch us social platforms for musicians, which sound great, but we’re hesitant to take on. Not only do native platforms take a lot of time to build, but there’s no guarantee people will use them. We tell these applicants to start smaller — build a community on an existing social platform, then when you’ve built up a user base, we’ll support you trying to migrate them onto your own one.

Start smaller, show results, get help, expand. This is the reality right now in Canada. If you want to acquire funding quicker, you’ll probably have to try your hand in the States. Hopefully one day we won’t have to say that.

Be Unique

“Create your own unique plate. Don’t bring the same food to the party that someone is already amazing at making”

It sounds simple, but creating truly unique value is difficult. A quick online search to see if anyone’s building something similar to you isn’t enough to understand what’s out there. Really knowing your market isn’t talking to a dozen people around you, or meeting with a couple executives. We had a startup apply for membership in the Music Den, saying they had studied their market for a long time — three months. When they walked out of the room, our steering committee expressed their surprise, almost in unison, “They think three months is a long time?!” Dipping into the market for a quick look around won’t give you enough information to succeed in it.

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