Coolness of an entrepreneur

Gary Vee just came out with a shoe.  Used to be shoes were only for athlete’s.  It was that way through the 80’s and 90’s.  Then the 2000’s struck and Jay-Z came out with a shoe.  50 cent did the same.  They were hits, but the trend didn’t continue.  Recently Drake has helped collaborate on Air Jordan shoes.

But Gary Vee has changed the game.  He recently released a new shoe with K Swiss.  He sees it as a move that has a huge upside and limited downside.  If the shoe is successful he is the first entrepreneur to have a signature shoe.  If he fails, he will have a good story to tell his grand children and it will be something that his friends will tease him for – which he is cool with.

That’s something I like about Gary Vee – something I think that we all envy in successful people – the ability to laugh at yourself.  If you fail, don’t dwell on it, but laugh at yourself.

How can Gary Vee get a signature shoe?

Nowadays being an entrepreneur is a cool thing.

This is only a recent phenomenon.  Shows like Dragon’s Den and Shark Tank and the rise of apps that have disrupted huge corporations such as Uber and Airbnb have changed the game.  Entrepreneurship is now a seen as something desirable and an option for high school and college kids.

I’m fortunate that they had an entrepreneurship class in highschool.  I took it in grade 12.  Its where I discovered people like Stephen Covey and his 7 habits of highly successful people.  I devoured success literature.  I started looking at music as a business.  It’s a big reason why I was able to carve out a path to success.

Entrepreneurship may look cool, but entrepreneurs know its about hard work.  Long hours.  Demanding work.  I think one of the hardest things is self discipline.  Being your own boss also means you don’t have someone telling you what to do.  You need to motivate yourself.

It’s easy when the product is selling and you are on regular hours like others.

It’s a lot more challenging when boring business work comes up when your partner wants you to go on a date, or be with the kids, or your friends invite you out to a party.

Cool or not, I wouldn’t have it any other way.




Realistic.  It’s a word used by parents, by teachers, by some friends.

It’s a word despised by kids, by dreamers, by entrepreneurs.

We see it as limiting.

They will say “Why dream big?  You are not being realistic.”

Dreams aren’t supposed to be realistic.

I like to think of the saying – aim for the moon because even if you land on the clouds you will be okay.

If you only set your sights on the trees, you may not get hurt from falling from a branch to the ground, but you also won’t get the benefit of the chance that your dream can come true.

Of course there is also balance.

You can’t always have your head in the clouds.

I see rappers aspire to be the next Jay-Z, or the next Drake.

It’s great to have these aspirations.  But it can also set yourself up for failure when you don’t achieve their level of success.  Both of these artists are one in a million success stories.

What should you do?

I think the best thing to do is aspire to be the best you.

In the words of Oscar Wilde – “Be yourself, everyone else is taken”



I liked grants when they were on paper

I’m not being nostalgic when I say that I liked grants when they were on paper.

Back in the days when I had to print out the application and fill it in with a pen.

Back when I had to press CDR’s and print a label that I would meticulously apply on to the CD.

I liked having to go to the post office and mail it off.

I even liked having to drive thirty minutes downtown to drop off the application at the office if it was deadline day.

I liked all of these things because I know most people weren’t willing to do it.

They weren’t willing to put in the extra work required and as a result, the odds swung in my favour.

Now its more of a level playing field.  It’s easier to write an application.

It should be a good thing – grants are accessible to a wider variety of applicants.

But with standardization, it has limited the ability to stand out.

Back then I would print with colour.  My marketing plans were often more than twenty pages so I would get them coiled at Staples.  The attention to detail made it stick out.

Now everything is done at your computer.  It’s tough to stand out.

But not impossible.  Knowing the importance of sticking out, I continue to look for the extra step that I can take to separate from the pack.


Help Me Help You


I like to think of myself as a helpful guy.

I have a passion for helping artists and I try my best to offer guidance and advice.

But sometimes I get frustrated.

I often spend more time than I think I would… or should.  Sometimes it feels like its a waste of time.

This can happen a few different ways…

I can send an email to an artist saying that I need to get some information from them, for instance their bio and three Youtube links.  I won’t get a response.

Or an artist can say, “Can we jump on the phone and talk about this some more?”

It’s good to touch base with someone on the phone, but in many cases these phone calls turn into: “So you you need like what you said in the email?” Me: “Yep.”  “Okay and this other thing is like in the email?”  Me: “Yep.”

Or it can be something that could have simply been solved by sending an email.

In either case, my initial desire to help turns counterproductive.

As a result, it can turn me off from wanting to help other artists.

If you are looking for someone to help you, the best thing is to value that persons time.

Don’t make it difficult for them to help you.

Make it easy.

Then they will look forward to helping you, instead of looking the other way.


First Day Of School

Nothing like the first day of school.

It can be nerve-racking and exciting at the same time.

One thing that its not? Boring.

You don’t have be in school to feel the impact of the first day.  It signifies a changing of the seasons.  Summer to Fall.  Or in business, second quarter to third quarter.

Time to begin again.

It’s been years since I went to school so nowadays I live vicariously through my kids experiences.

As I see them get ready in the morning, it makes me think back to going through similar routine, but more than that I recall those same emotions.

One sticks out more than anything – nervous excitement.  Nervous because its something new and you don’t know what to expect.  Excitement for those same reasons.

Even when you aren’t in school, the first day of school can sharpen your focus on your goals.

First, it can be reinvigorating and help you to push thru and finish the year on a high note.

Second, it can get you thinking ahead and to focus on the goals that you want to achieve in the new year.  The next six months take you into the first couple months of the year so you realize its coming soon.

One thing that never changes – always making sure you look fresh on the first day.

Bring This Guy Back, He’s So…

Bring this guy back he’s so…


I was doing a show at a highschool and arrived at 7:45.  An early time to be preparing to rap, but also an early start time for a highschool that was beginning at 8:15 am.

I couldn’t imagine starting school at 8:15 as a highschool student.  I remember how tired I was in the morning.

Of course my day didn’t begin at 7:45.

I was on the road at 6:45 and punched the address into my phone.  I know it should take between 40-45 minutes but its the morning, its Toronto traffic, and I was set to be on three busy highways.

My alternative was taking the 407 – the toll highway.  My Iphone showed that the 407 wasn’t going to save me time.  It was 40 minutes on both routes.  As I jumped on the first highway, I noticed the traffic was getting heavier.  I could trust the Iphone but what happened if things changed half way through my journey?

So I jumped on the 407 and ensured that I’d arrive on time.  And I did.

I walked into the schools gym and they were setting up.

The main equipment that I need is a projector – which I cleared that the school had prior to my arrival.  I let them know that I use a sound system and if they had one that would be great.  They did – but it was on the same cart as the projector and looked like a small system that was better set for plugging in a video game system for playing in the living room rather than for rapping and speaking in front of a few hundred students.

But the vice principal assured me it should be okay and that the microphone was being plugged into the main system.  I went over to the teacher that was setting it up.  He passed me the lapel mic that I could clip on.  “Do you have a handheld?” I said.  As a rapper, I always prefer having a microphone in my hand.

He said they did, but then remembered that it had been misplaced so he connected a corded mic while he went to look for it.

After seeing that he hadn’t returned for a few minutes, I took out my own mic and replaced it with the corded one.

When the teacher came back in he was about to apologize that he couldn’t find the cordless when he smiled and said “Wow, you are really prepared.”

He didn’t even know about the sound system that was in my trunk, just in case this one wasn’t sufficient.

The vice principal came back.  She asked the teacher if he had his Macbook here because the presenter working in a separate room forgot his power cord.

I reached in my bag and pulled one out.  I had purchased a new computer a couple months ago but still bring my old one out to shows… Just in case.

That’s when the teacher said “You’ve got to bring this guy back.  He’s so prepared.”

I could have just relied on their equipment.  I used to do that.  Most times it would go well.  I’d say 95% of the time it would be fine.  But that’s also when I was just getting started.  Not a rookie, but less than 100 shows under my belt.  Now I have over one thousand.

I remember the times when the corded mic was connected to an antiquated PA system and it was scratchy and nearly inaudible.   I remember how the “sound system” was a small boombox equivalent to what I had in my bedroom as a teenager.  I remember how I didn’t regulate crowd size and now there was six hundred students listening to me and how I could hear that I didn’t have full command due to the sound limitations and felt powerless to do anything about it.

That’s why I also remember how buying the sound system was one of the best purchases I’ve made.

I’ve had it for over eight years now.  There is duck tape around it from dropping a couple times.  Sometimes I have to adjust the cord a little to make sure one of the channels works.  But other than that its fine.  And if it ever becomes a problem I won’t hesitate to buy another.

But back to the show.

Since I was prepared I had time to chill before the show started.  I was talking to the teacher and vice principal and surprised how I was only speaking in front of one grade.  They had two other speakers in to talk to other grades.

It’s something they did every year.

That’s when the bell went off.

My preparation could lead to coming back next year… and maybe the year after that.

I’m prepared for that email.




Cheating Yourself

I used to love it when we were able to mark our own tests.  Doesn’t matter the which teacher, they would always say the same thing “When you cheat, you are only cheating yourself.”

Sure, I thought.  I just wanted to get a good mark.

But as I’ve gotten older I’ve seen the wisdom in that statement.

I keep track of my gym workouts by putting them into a spreadsheet.  I always aim for four workouts a week.  If I do three – that’s decent.  If I do five or six – that’s great.  But four is solid.

I could fudge the numbers.  But whats the point?

When I only have a two workout week, it doesn’t look good but it reminds me that I’ve got to step my game up.

Accountability leads to greater results in the future.