Interview: Jess Joss

Jess Joss is the Executive Director of York Angels, mother to a seven-year-old, and an all-around inspiring woman with a positive, humanitarian attitude toward investing that infuses all aspects of her life. In this conversation, Jess shares highlights from her investment journey, gives insight into what motivates her investments, and provides a few pointers for fledgling angels.

Meet Jess

Current roles: Executive Director, York Angels; Board Director, National Angel Capital Organization

Hails from: Greater Toronto Area

Education: Bachelor’s Degree in History and Diploma in Internet Business and Technology

First Job: at the cottage marina during Grade 9

Work Attire: I like to have fun with it. I wear lots of color, and I’m really into boots and throwing on a little leather jacket — I’m big on easy fashion.

Hobbies: Photography, spending time at my cottage, and enjoying the outdoors

How Jess began angel investing

I became an angel investor in 2009, and I joined York Angels early on because I knew some of the organization’s founding members. Two of my business partners joined at the same time, so with our holding company we started making investments.

Her first angel investment

The company was called Top Hat Monocle, a platform for in-class quizzing in university and college settings, making it easy for professors to glean whether or not the class understood what was going on. The founding members of York Angels had done a lot of due diligence and I was very young and green. I decided that sooner or later I had to take the plunge. So that was my ‘jump off the cliff.’ It was a good one!

This first investment came through York Angel, and some of the other angels that I'd gotten to know well were also participating. I think maybe there was a comfort level in that. As you start out as an angel, you’ll likely have to take big a leap sooner or later. Getting to know other angels within your organization makes that leap seem less daunting.

How she evaluates deals

I'm always looking at factors like: How does this investment work in terms of marketing? What is their niche? What is the makeup of the team? I'm really big on team. My colleagues tend to focus for the role a strategy plays — what's the plan for an exit? So we balance each other out well, though in terms of a thesis we are incredibly varied.

The motivation behind her investments

As an entrepreneur growing up in an entrepreneurial household, I certainly remember – both from my personal journey and from my family's journey – the people that gave us pivotal financing and advice. So for me, there’s that element of giving back by paying it forward for sure.

I also have a love of lifelong learning, staying engaged, and staying current. I really appreciate those people who, no matter their age demographic, are keeping abreast of what's happening in the world and its evolving influences.

Being a part of innovation [by investing in it] and supporting founders and their startups is a great way to observe, and shape, how the future is changing. I think supporting Canadian founders and Canadian innovation is an important, long-term strategy for Canada’s economic growth.

Advice for new angel investors

Educate yourself! Whether it be online, at seminars, or attending events, find a place where you feel included and remember that your opinions are valid. Get a mentor to guide you. Remember that though investors have varied investing styles and thesis, all styles are valid. Invest for what is right for you, and hold true to that.

If you already have a field of expertise, get involved in that area. Knowing you can actually help the company and its trajectory, rather than just providing the funds, can be very rewarding. Find an open and inclusive investment space and then sit back for a while, listen, learn and when you feel ready, pull out your checkbook and get involved!