By Katherine Hague (Founder, ShopLocket)
This is the story of how my startup, ShopLocket, found its first investor, Heather Payne.

In startup land, we spend a lot of time thinking about that elusive first dollar. Whether it’s from a customer, a bank, or an investor, they often say that it’s the first dollar that’s the hardest.

Every startup’s path to that first dollar is different, but each is surely equally reliant on pixie dust and the stars aligning. Here is my story.

How I Met My First Angel Investor

Heather and I first met at Startup Drinks in Toronto in August 2011. We had first connected on Twitter and decided to both show up at the event, grab beers and chat. At that point, neither of us had many female friends in Toronto’s startup community and I was excited to connect with someone I thought might be similar to me. Neither of us expected it to be the start of something quite so exciting – both personally and professionally. After all, it was just a beer.

When we met, Heather and I were both working at tech startups but had dreams of one day quitting our jobs and starting our own companies. Heather is a great connector (I learn this more and more everyday) and I soon found myself int of a small group of female “wannabe-founders”. We’d get together every few weeks to brainstorm, check our progress, and support each other as we planned our paths toward world domination.

For me, finding a problem worth solving had always been the challenge. I‘d come up with a lot of ideas I liked, but didn’t love. It wasn’t until last summer, when I was looking for a way to sell some cute t-shirts I’d had custom-made that things finally fell into place. I couldn’t find an easy solution for selling a single product from a website, blog post or Facebook Page.

Since I only had one product, an online storefront didn’t make sense, and with all the setup time and fees involved, it seemed too risky. All the other alternatives involved redirecting buyers to another site or designing a product listing from scratch. “Why was selling a single product online so difficult?” I wondered. The idea for ShopLocket was born.

Timing Is Everything

I kept my full-time job, but started working on ShopLocket on the side. And as I learned more about the potential size of the market, I knew I had finally found my problem worth solving. “Why doesn’t this exist?” I kept asking myself.

At the same time, Heather’s side project, Ladies Learning Code, was taking off. Her workshops for women (and men) who want to learn beginner-friendly programming and other technical skills in a social and collaborative way were quickly becoming wildly popular.

After running two sold-out, wait-listed workshops (and a launch party), Heather couldn’t ignore the opportunity any longer – she was ready to make Ladies Learning Code a larger part of her life. Almost exactly two months after meeting each other, Heather and I worked up the courage to leave our jobs, take a giant leap and become full-time entrepreneurs. Neither of us shared our plans to quit in advance but, somehow, we both resigned on the exact same day. October 22, 2011. Coincidence? Must be.

After my two weeks’ notice ran out, I started working on ShopLocket full time, while Heather got busy figuring out how to turn Ladies Learning Code into a self-sustaining not-for-profit. Now happily unemployed entrepreneurs, our support group became more important than ever. Knowing there were people we could call on to share our successes and failures made an enormous difference, especially in those first few doubt-filled days.

By early November 2011, I had my first working demo of ShopLocket and was eager to show Heather and the rest of our group. Although she’d been involved as I worked through the idea for ShopLocket, it wasn’t until she saw the demo that “it hit her” (or, at least, that’s what she says). She immediately understood the need for a product like mine. A solution for people with something to sell, who aren’t ready for a full-fledged storefront, but still want to showcase their product in a beautiful way.

Your Angel Investor Should Believe In You And Your Product

Heather may not work for a VC fund or be part of an angel network, but she believed in me and the product I was committed to building. As I wrapped up the demo, she told me she wanted to invest. I think we were both pretty surprised by that announcement. We decided to sleep on it before saying anything more. But the next morning, we both felt the same way – it seemed like a great fit, for me, for Heather, and for ShopLocket.

It took three and a half months to make it official, mostly due to lawyer-ing. But at no point did either of us have second thoughts. We made the decision, and went for it. Today, as we officially launch our beta, we’re both more excited than ever about ShopLocket’s potential.

Six months ago, I know that neither of us could have imagined what we’d be doing today. I’m sure Heather didn’t think she’d be running Toronto’s hottest not-for-profit startup, let alone that she’d be an angel investor. And I know I didn’t expect I’d be raising money to build an e-commerce platform (with, I might add, the support of one of the coolest new angel investors in Toronto).

Let’s just say that you never know where a chance encounter might lead. And that first investor?

Well, it doesn’t have to be as scary as you might think.

Editor’s note: Got a question for our guest blogger? Leave a message in the comments below.
About the guest blogger: Katherine Hague is the Founder of ShopLocket. Prior to launching ShopLocket, she was working as a Marketing Manager at Toronto startup ecobee. She has a passion for technology and entrepreneurship and have spent the past fews years active in the Toronto Startup community, is long time member of the Impact Entrepreneurship Group. Follow her on Twitter at @KatherineHague.