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My First Company

Seek Discomfort Black Friday Drop is currently live here! If you order today you get 2 free flags with your purchase. Thank you for all the love and support, it doesn’t go unnoticed <3

Lisa Smart. 

I’ll never meet her and you’ve never heard of her.

But she changed my life. 

Lisa was the first stranger to ever order from my first company, Heart City Apparel.

I’d started Heart City out of my college dorm room in 2014.

Walking to and from school in Montreal I couldn’t stop noticing two things: the beautiful street art and the rampant homelessness. These two polarizing forces came together into one idea. I would sell clothing designed by street artists that would give back to homeless charities in their city.

I couldn’t have been more excited.

I selected the first street artist, found a manufacturer and built a basic website.

After an agonizing several months I’d emptied my bank account and was ready to go.

Prior to launch, I sent the website link to as many friends as I could, asking them to share it. I was certain this idea would explode. I had visions of raising millions of dollars for the homeless, of working with the Shepard Faireys and Banksys of the world and being interviewed by Ellen.

Expectations were at an all time high.

I clicked upload and waited.

Then waited longer…

Lots of my amazing friends shared the link and a handful even spent their hard earned money to support me.

My parents ordered two shirts and three sweaters. 

My cousin got himself a tshirt. 

And then after thirty minutes, the visitors on the site went to zero. 

Although I was thankful for the support of my loved ones, I was bummed that I hadn’t reached anyone outside my network. The insecurities of every first time entrepreneur started to creep in...will people who don’t know me care about this? Is my main customer just going to be my mom?

It was late so I went to bed. 

I got up the next morning and opened my email. There was an unread message at the top of my inbox. ‘New Order’, it read. I opened it. 

Lisa Smart.

She’d ordered one of my 20 size Small crewnecks.

I didn’t recognize the name.

Was she a friend of a friend? 

I looked her up on Facebook. I needed to find out who this person was. There were lots of Lisa Smarts but I wasn’t mutual friends with any of them. 

This may sound trivial but her anonymity blew my freaking mind.

Someone I had never met or known was confident and excited enough about my new company to order from it. 

They trusted me. 

They believed in my mission.

Lisa gave me a new lease on life. She convinced me that there was something here. That I needed to keep going. 

If it weren’t for Lisa I’m not sure if I would’ve continued the company long enough to meet Thomas. It was six months later that I met Thomas when his marketing class consulted for Heart City.

And now look at where we are. 

Just yesterday I was standing in our new 15,000 square foot warehouse walking around in awe. 

There are thousands of items being shipped as we speak to people I’ve never met. 

As I walked around the warehouse I couldn’t stop thinking about Lisa. I imagined what she would think if she knew that if it weren’t for her, there’s a chance none of this would exist. 

So this is a thank you to her, to you and to everyone who supports strangers’ dreams.

Your stamp of approval and your trust are the lifeblood of dreams. Just one purchase, one positive affirmation from a stranger, can keep the wind in the sails of a wild idea. 

As we continue to build Seek Discomfort, we want our company to support the world’s change makers. We want to back those who dare to take action on their dreams. We’ve done it with Anders. We’ve done it with Symphony. And we plan to do it for thousands more.

A stranger believed in me and that’s how I met Thomas, Ammar and Derin. Then you believed in us and that’s how we’re here today. 

It’s only right that we repay the favor. 






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  • Observation
    Seek Discomfort spelled and printed in the normal way is comfortable. Wondering your reasoning in becoming comfortable in your choice of print/spelling style of “Seek Discomfort”.

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