Life, Values & Legacy: Our Chat with Grizzy Wynter of Montreal

We’re looking forward to introducing you to Grizzy Wynter. Check out our conversation below.

Hi Grizzy , thank you so much for taking time out of your busy day to share your story, experiences and insights with our readers. Let’s jump right in with an interesting one: What is a normal day like for you right now?
I wake up , do insanity for 30 min , mediate for another 15 -20 min , have a shower , get ready , go to work at my day job as a crisis intervention worker, come home do some video editing for clients and write some music or record a vocal take and pray and hit the sack

Can you briefly introduce yourself and share what makes you or your brand unique?
My name is Gerald ” Grizzy” Wynter , I am a Musical artist and Songwriter , A content creator and Videographer and Editor for my own company , Coldest Wynter Entertainment. I specialize in Social Media Marketing and video content creation. I Started off making music and performing for 10+ years, I have opened for Tech N9ne, Obie Trice , Cozz , Swollen Members , Kryple and Toured Across Canada and won awards for Best International Artists for the Binge Awards in 2021 in Los Angles and been Nominated twice by the Wavy Awards in NYC for Best Album (2021) and Best Production (2025). I have 2 albums that have hit over 100k on Spotify and other streaming platforms (Illuminate & DMGDZ) I recently revamped my business, Coldest Wynter Entertainment from an artist management business to doing solely Videography and Video editing with media marketing because I enjoy the work more. While I am not dropping music as frequently I am still working on projects and constantly writing new songs.

Amazing, so let’s take a moment to go back in time. What did you believe about yourself as a child that you no longer believe?
That I wasn’t good or that I wasn’t worthy of being loved. That belief stunted my growth and my self worth greatly as a got older only through therapy and a deep spiritual connection did I overcome these mental blocks I had put on myself.

What have been the defining wounds of your life—and how have you healed them?
I have had so much, I think the two that have really affected me was I was molested when I was 11 by a close friend while his father watched. Severely messed up. I buried that for a long time and it made me lash out in anger for a really long time. I also didn’t start dealing with the affects of that until I was in my late 20s. Keeping those emotions buried led to the other wound, Being a victim of gun violence at 18, I had problems with a deeply racist white kid in my school , we had fought previously where I had won but the anger had never left him, he attacked my home with bear mace while I wasn’t home and in a rage I agreed to fight him only for him to pull a pump action shotgun on me, I disarmed him and if it wasn’t for my friend I would of taken the weapon and used it on him myself but chose a better path thanks to him taking me down, later on he used the same gun and attacked my family home.
That action sent me on a destructive path in my early 20s of crime and drugs, that while I don’t regret I wish I had made better choices but through all of those things have me an ability to empathize with others who feel like they are about to give up and be what the world is telling them to be

I think our readers would appreciate hearing more about your values and what you think matters in life and career, etc. So our next question is along those lines. Is the public version of you the real you?
I used to think so, one of my ex’s told me once that she loves Gerald but hates Grizzy. I used to think that I was being myself at all times or at least Grizzy was just the heightened version of me but I realize its not.
Gerald is very laid back and observes the world, I think that’s why I took to being a Videographer and a editing because I can see thing for what they are in that way and make things beautiful.
Grizzy is more of my loud, unapologetic side , that is fearless and doesn’t wait for thing to come my way Ill make that way regardless.
I think in the era I’m in now I’ve excepted both sides and healed the shadow in both to create a fully formed person who is exuberant but observant, who will leave the world better than I came into it

Thank you so much for all of your openness so far. Maybe we can close with a future oriented question. What do you understand deeply that most people don’t?
That most people can manifest the life that they want if they start speaking it into existence. The thing is that most people have been programmed into not trusting themselves or instant gratification. If you believe you will be successful you will be but it doesn’t happen when you want it. I put it like this I do 80% of the work and god does the last 20% and you’ll be ok

Contact Info:

Image Credits
Gerald Wynter

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