Jess Joss

Jess Joss


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President, Equation Angels

Mentorship – Jess Joss

“Be strong in your goals but flexible in your methodology.”


Jess Joss is the CEO of Equation, a joint venture that brings together three angel investment networks, Co-founder of Insiteful Solutions, and Partner in Spyder Capital Corporation. Leveraging more than 20 years of business leadership, entrepreneurial expertise and investment experience, she played a pivotal role in the realization of Equation, and its impactful investment collaboration.

Jess’s passion for entrepreneurship was ignited during university when she founded a web development company that continues to thrive today. As the founder, she grew the business, evolving and scaling the business into an integrated online marketing firm. In 2001, with a proven business model, established revenue streams and new partners, Jess shifted her focus from leading Insiteful Solutions to investing in high-growth startups. With extensive business experience, Board and volunteer management expertise, Jess was appointed Executive Director of the York Angel Investors (YAI) in 2014. This built directly on her strong track record as an active angel investor with the group for many years.

Capitalizing on her entrepreneurial, business, and marketing acumen, Jess worked with the YAI team to grow membership by over 450 percent, and significantly increase deal flow, the number of deals completed, and amount invested per deal. This renewed energy and motivation earned YAI the honour of being ranked among the top five angel investor networks in Canada in 2015 and 2016; and first place in 2017 and 2018. During this period, YAI established the largest membership of angel investors in Ontario and second largest membership in Canada. Jess completed her work with YAI at the end of June 2019, preparing an opportunity that combined her investment and entrepreneurial passion.

In October 2019, Jess led the launch of Equation, after being announced as its founding CEO. This strategic alliance brings together three venerable angel groups: Angel One (Burlington), Golden Triangle Angel Network or GTAN (Kitchener-Waterloo) and the Southwestern Ontario Angel Network or SWO (London). This angel network is now the largest in Ontario, and second largest in Canada. Equation provides streamlined screening, pitching and due diligence for founders who are raising equity funding. And for the 200 member investors, it creates a unique opportunity to gain early and exclusive access to the most promising companies; negotiate the best deals; and make nimble investments. This is an stimulating and challenging role, and Jess enjoys working closely with amazing colleagues, angels and ecosystem partners. She is currently taking a short sabbatical and looks forward to returning to this exciting role in the coming months.

During this time, Jess continues to demonstrate leadership and make critical contributions to Canada’s entrepreneurial and investment ecosystem. She fosters early-stage innovation by coaching and mentorship; serving as a speaker at entrepreneurship and investment events; and judging pitch competitions. She was also elected to the NACO Board in October 2017, where she serves as the Marketing Chair, and member of the Team Enhancement (HR) and Finance Committees. She also served as Chair of the 2018 NACO World Angel Investment Summit (Conference).

A passionate connector of people, technology and opportunity, and fueled by a love of entrepreneurship, mentorship and angel investing, Jess works closely with ecosystem partners, dedicated angels and game-changing young companies looking to grow. She is committed to driving growth, customer, revenue and capital acquisition, exceptional exits, community and economic development. Building directly on these objectives, she maintains the transparency of the angel investment process, while cultivating collaboration, community engagement and deals.



Jess Joss

The full #OPNAskAnAngel talk

All right. So welcome everybody today we are at ask an angel and today we are with Jess Joss. And we’re very excited again to be able to dive right into the whole Angel community and ask Jess a lot of great questions and maybe we can start off just by giving a little bit more of a background on yourself. If you could kind of give that worldly view and then now we’ll jump in from there.

Great, thanks so much for having me today. Very much appreciate it. In terms of my background, like all good investors I am a history major. That prepares you for everything in life. Gives you a good context for where we’ve been at least. Started my first company right out of university that company still continues. It’s an online services program marketing etc website design and that continues today. I started investing about 11 years ago, 12 years ago. Joined York Angels which was my first angel group, and that was my initial experience as being a member within an angel group. Had done something investing previously aside of that group but once I joined an angel group I decided that that was definitely my preferred ammo to work with other angels and collaborate. And so after being an angel there for a number of years in 2014, I became executive director and had an amazing opportunity to work on the management side, grow the organization, work within the ecosystem, meet other angels from across the country and around the world, work with some great entrepreneurs, continued to do that until June 2019. So a year ago and then at that point in time I moved to a new organization. And that was an opportunity to work with three angel groups bring them together under one brand and one of one umbrella and that was called Equation. And the angel groups involved in that are GTAN to Kitchener-Waterloo, Angel One out of Burlington, and Southwestern Ontario out of London. And so I had an opportunity to work with some amazing angels, they’re really interesting entrepreneurs. I learn slightly different aspects of the ecosystem and the value of equation is bringing together more angels making it a faster and more efficient application process for the entrepreneurs fill your round quicker, and provide economies of scale, and values to our angel members. So that’s an equation which continues to grow and thrive. Over the winter of 2020, I took a leave of absence just to deal with some family health issues and so I’ve been working with that. But still keeping my toe in the angel waters and within the ecosystem.

Awesome. And well, we’ve known each other for about five years I think, four or five years, since we started this, I started going to York Angels. And I’m a big fan. So and I see that there’s a lot of great things that you’ve done for the community inside of that. So you obviously love investing. So I guess the big question is, what got you into investing? What was that trigger, that was really pushing you to go and say, you know what, I need to get in this space?

It’ interesting because I grew up in an entrepreneurial household. On my father’s side and watched him in the startup phase, startup two businesses one very successful. And at the time, there was investment but we would never have called it angel investing, it was you know somebody lent you money or somebody you know bought into the company because they believed it and so on. But I wouldn’t have known it as a child as angel investing. But looking back that’s exactly what it was in terms of the size and the scale of it. And as I grew up, there was an opportunity for I watched my father invest in other businesses. And I think, a lot of it pay it forward was how that started. And seeing that as an example because many entrepreneurs remember that one person or that piece of advice or that investment that was right at the linchpin, right at that critical moment, that really helped with the inflection, and then there’s a desire to do that again for others. So my initial motivations definitely came from that area. As an entrepreneur