I F*cked Up: Three Entrepreneurs Get Real About Their Biggest Fails

Three things are certain in life: death, taxes, and making a lot of mistakes as an entrepreneur.

There’s no sugarcoating it: entrepreneurship is hard. It’s rife with challenges like financial instability, stiff competition, and unpredictability. It can be lonely and daunting, making it a challenge people think twice about before undertaking.

Many aspiring entrepreneurs never start a business because they know uncertainties are guaranteed and failures are bound to happen. But here’s the secret: business missteps don’t need to stop your momentum—instead, they can be the key to your path forward.

Failure is the successful discovery of something that does not work

Tobi Lütke, Shopify CEO & Co-Founder

Mary Young, Gregory MacDonald, and Vivian Kaye know all about business mistakes. All three are now successful entrepreneurs with established businesses, and they took some time to reflect on their biggest blunders and the lessons learned along the way. We won’t spoil any more details; here are their stories, in their own words…

I hit the jackpot and it (almost) got taken away from me

by Mary Young
CEO & Designer, MARY YOUNG

Mary Young portrait with collage design as backdropAs the founder and designer of my own lingerie brand, getting my line into a big box retailer was the ultimate dream. After years of scouring LinkedIn, reaching out to buyers, and showing up to their in-person trade shows, I managed to get an in with a buyer from Nordstrom—the holy grail of retail. I met her at a tradeshow, told her all about MARY YOUNG, and sent her samples.

A couple of months later, I got a purchase order for 11 stores. Jackpot! We rushed to get the orders out the door despite a tight deadline. As soon as they were shipped to their locations, I had to celebrate by treating myself to something nice. I went to the mall and bought new sneakers.

Bag in hand, smile on my face, and head held high, I was heading home that same day when I got an email from Nordstrom’s legal department informing me of issues with the product labels: the ‘made with’ materials label was not specific enough to meet US regulations. Nordstrom was about to send all my products back and not pay for the inventory. I stood at that traffic light corner, reading my email, dreams crumbling.

I was crushed. Deflated. Defeated. How did I not look at label regulations in the country? I thought they’d be the same as Canada, where my products were designed and sold.

Shortly after, I went into laser-focused solution mode. I spent days researching US label regulations and found a scrappy hack: cut off the labels on every product and print new stickers to place on the price tags. Thankfully, Nordstrom agreed, and their hero employees went to work, cutting and stickering.

Crisis averted and lesson learned: stay naive and stay agile. Life will throw the most unexpected curveballs at you.

I got my product on TV and everything went haywire

by Gregory MacDonald
Co-Founder, Bathorium

Gregory MacDonald portrait with collage design as backdrop

You know how they say the third time’s the charm? Well, they lied. I lost count of my failed pitches as I spent years sending my bath products to morning show producers. I was so close to giving up, but in January 2018, I got a congratulatory call: Bathorium’s products were going to be on Good Morning America’s Deals & Steals segment. Huge!

We had eight weeks to get a new production facility ready, make products, and open a fulfillment center in the US. We hired everyone we knew, from parents to friends and cousins. We hustled and got it all done. We felt good. The big day came and the segment went without a hitch!

Of the 22,000 KG of product we shipped to our Chicago-based fulfillment center, we sold and shipped 80% within the first 48 hours. Not so bad for a business that I started from my tiny condo in Toronto four years prior. 

I know, I know, this sounds like an entrepreneur’s fairytale. So what went wrong?

Well, of the 7,000 new customers who we thought were about to be repeat customers, only five came back. It turns out, Deals & Steals segment shoppers were deal shoppers, not brand loyalists. We were banking on the latter. The inventory in our new expensive fulfillment center was not moving at the rate we needed it to. Costs were adding up and the business was in financial free fall. I didn’t know how I’d make payroll or pay rent. I was so stressed I couldn’t even eat or listen to music.

I needed an action plan and I needed it, like, yesterday. We scrambled to start clearing our inventory in Chicago by offering the right discounts to the right people. We consolidated inventory, and got tenacious about getting our product into retail stores. Today? The business is doing better than ever and we went back on GMA in February 2020 for a redo—this time with all the learnings in our back pocket!

Onwards and upwards. (Though sometimes, you’ll go downwards).

I mixed business and pleasure… and it got personal

by Vivian Kaye
Founder & CEO of KinkyCurlyYaki

Vivian Kaye portrait with collage design as backdrop

I spent years working on my side hustle—a bridal decor business—at my 9-5. Things were going splendid as I scaled that company to 6 figures. But that all changed when my chill, supportive boss left and I got a new one that caught on to my ways. I was let go shortly thereafter, so I turned my decor business into a full-time job.

Without the pressure of the corporate office, I started ditching my hair relaxer for a more textured look that was more in line with who I was. As a Black woman, it felt liberating to wear high-quality, kinky, curly, and natural-looking textured extensions. 

Other women took notice, and they started asking me where I got my hair done. I was clearly onto something there, so I started a high-quality hair extensions business to celebrate the Black women who wear them.

A few years later, in 2014, I made $600,000 from that business. I also got pregnant—with my business accountant. He was good with numbers, and I needed help with them. He encouraged me to incorporate and go into the business as partners. That entailed giving him 40% of the company.

Big oopsie… because shortly after, in February of 2015, he left me and my son to move to another province, where it turns out he had another family of his own.

I’ll spare you the tough details, but what followed was a long legal battle to get his name off my company’s books. I fought with all the perseverance and grit I could muster.

In 2016, I made my first million. Alone. In 2017, I repeated that feat. I guess you could say the tenacity paid off.

Remember, just because you fucked up, it doesn’t mean you’re a fuck-up.


These accounts are edited and condensed from stories shared at Fuckup Nights Toronto, a speaker and community series for professionals and entrepreneurs. 

This piece originally appeared in the print edition of Shopify Magazine. Special thanks to Marsha Druker, Founder of Fuckup Nights’ Toronto Chapter.