Tell us about a time that you made a mistake or failed at something.

Sheldon Anderson
Sep 6, 2018 · 3 min read

One experience that comes to mind is when I failed at the t-shirt company, called. “Next Generation Apparel”. I designed First Nation’s casual apparel. My first shirt had a feather on it, with the name on the bottom. I started selling shirts out of my locker at University, made some sales, and was nominated for some awards, and even made a page on Shopify. I had a vision of making millions and changing the game of entrepreneurship. Even though I’ve never run a business before, but I had so much momentum — To the point where I decided to take a year off school to make this company happen.

I had orders from friends, university professors, and even old government colleagues. Originally, I invested $250 in the company — not a huge loss. However, I couldn’t fulfill all the new orders I promise without more capital, so I went to a bank (didn’t know how to pitch for investments) and was denied. I had some savings, and I just read, “The Upstarts: How Uber, Airbnb, are changing the world” by Brad Stone. There’s a story about the Airbnb guys putting their company on a binder full of credit cards until they were picked up by Y-Combinator and the rest was history.

I thought to myself, “I have some savings and I can get a credit card to pay for the new orders.” I thought I was going to be the Brian Chesky (CEO of Airbnb) of t-shirts! Biggest mistake of my young business life… I couldn’t fulfill all the orders because there were so many costs I didn't appetite and my credit card was maxed.

There was hope, a pitching competition with the grand prize being $500. If I won, I can fulfil all my orders and recoup some of my investment. This was it, my ultimate business challenge, one they’ll write about in my biography. I paid for coaching, practiced my pitch, even broke down the entire process of Dragons Den… I was ready. I remember the day was cold but I was red hot with excitement. We did some workshops and got ready for the pitch, I was ready. People began pitching their hearts out then it was my turn. I spoke with passion and certainty, I answered all the questions right. It was the perfect pitch. I crushed it, I started counting my money.

The winners were announced and my business didn’t even make the top three. I was crushed. I made some hard phone calls saying I couldn’t make the orders and that my company is now frozen due to no funds. Momentum has gone. This impacted people I was selling too, business organizations that wanted to see me grow (Shopify shut my website down, couldn’t keep it going), and my family. I apologized to all of them. Everyone was understanding, and it was just t-shirts — no big deal. I was more disappointed that I didn’t follow through on my word.

I learned more from losing that day; I needed a clear value proposition, business mentors, key partners, key stakeholders, and a solid business plan. Most importantly, don’t spend money you don’t have. Now I’m doing social media management for a smaller company and look to use the lessons learned from my first company to one day start an e-commerce/digital agency. I also just paid off that credit card…

Lesson learned.

Sheldon Anderson

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