We recently connected with Alex Cronin and have shared our conversation below.

Hi Alex, thanks for joining us today. Almost all entrepreneurs have had to decide whether to start now or later? There are always pros and cons for waiting and so we’d love to hear what you think about your decision in retrospect. If you could go back in time, would you have started your business sooner, later or at the exact time you started?

I don’t think starting earlier would have helped me.

When we started Permanent Vacation in 2016, I was in a completely different place. I was managing a music artist, out a lot, having fun, not really thinking like a brand owner yet. We had ideas, but we did not understand what it actually takes to build something that lasts.

You can start a brand at any time. That is the easy part. The hard part is knowing what you are building and why it should exist. I did not have that yet.

Over time, things started to click. I began studying other founders and brands I respected. I changed what I was consuming every day. I paid more attention. I started to understand how many moving parts there are, and how much work goes into scaling something properly.

What time gave me was maturity and patience. I learned how to sit with the boring parts of the business and not avoid them. I also learned that if you rush to scale before the identity is clear, you lose the whole point of the brand. It turns into something else.

Right now is the first time it actually feels clear. The identity makes sense. The direction feels intentional. We are not guessing anymore.

So no, I do not wish I started earlier. I think I needed that time to become someone who could build it properly.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I’m just a guy who wanted to create a brand with my best friends, and that’s how it all began.

I was born in the Soviet Union in 1986 and came to Canada as a refugee with my family in 1992.

I used to be a songwriter and managed a music artist in 2016 when I came up with PERMANENT VACATION. One day, I teamed up with my co-founder Andre, who is incredible at graphic design and apparel printing, and we made some hats for friends. That’s how Permanent Vacation started.

One of my best friends, Andrew “Quillie” McQuillan introduced me to a mentor, Shane Foran, who gave us our first big break by getting us into a store. Quillie passed away one year after we started the brand. Quillie’s optimism and passion is something that lives with us today as we build this brand in his honour.

Can you share a story from your journey that illustrates your resilience?

We started Permanent Vacation as a group of friends. It was simple. We made a few hats and thought it could be something.

About a year in, we lost one of us. Quillie was one of my best friends. I started the brand, but he made it feel real. He connected people, opened doors, and pushed it forward before it had any reason to move. He got us into our first store, and that changed everything.

Then everything stopped.

I had already lost my father in 2014. Losing Quillie right after was super devastating. By the end of 2016, I was shut down for almost a year.

When I came back, the mission felt sort of changed. It was not just something we were building anymore. It was something we were carrying.

We are still here. Still building. And a big part of that is to make this a success in his name.

How’d you meet your business partner?

I met Andre when I was about 15. I was a rapper in a duo called Cartel North, performing around Toronto.

One day, I walked into a recording studio in Andre’s basement, he recorded my track called “By Any Means Necessary.” Andre was always multi-faceted. He had the studio, but he was also printing t-shirts for local rap groups out of his garage, and back when CDs were big, he was duplicating and printing them. He even printed a number of CDs for Drake’s breakout project “So Far Gone.”

After that first session, we stayed connected, and years later, we started Permanent Vacation together.

Contact Info:

• Website: https://permanentvacationbrand.com
• Instagram: https://www.instagram.com/permanentvacation.xyz/

Image Credits

Jaden Trinh