Jeffery:
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.

Jess:
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.

Jeffery:
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?

Jess:
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 myself, I saw not only the value of the investment of money, but also the mentorship that I received when I was growing my business and how you know the connections the mentorship and having that really sort of sage sounding word was really important to me as I grew and developed my business and pivoted and and so on. So you know decide to provide that back and then when I came together through the investments I did on my own, they were good. but they weren’t it was a [sic]. I was very new to the field so it was certainly a lot of heavy lifting and then when I came forward to an organized angel group for me I found that, that was a great space. I liked sharing the due diligence, I liked the collaboration with other investors who brought different perspectives so I could invest outside of my wheelhouse then. I’m in a variety of verticals that are not my expertise but based on the relationships I’ve built with fellow angels who are experts in that field that was enough to help me make a decision to invest in something that’s outside of my wheelhouse. So for me, I’ve really enjoyed the collaborative angel investing experience but I think there’s, you know, I see it as giving back. Because I’ve had opportunity, I’ve had I’ve been, you know lucky, successful, whatever it may be and I think that’s important. I see it also as something that’s really good for our country. We’re you know a large country with a small population. But I think especially in technology, I think there’s an opportunity for us to really sort of punch above our weight. And I think that it’s an opportunity as Canada, you know for many many years we were very strong in natural resources, and pivoting into more tech and things that are more scalable, I think that’s good for the future of our country so that’s another reason why I like to invest. And it’s interesting once you’ve done it. It’s absolutely addictive because you you meet fantastic entrepreneurs, you meet some other amazing angel investors, you get addicted to seeing new, technologies and seeing trends… So it becomes something very quickly I think that you always want to be a part of because there’s a pulse and energy to it , and I think that’s also an optimism. As someone who is an inherently optimistic person, you know is there any act that’s really any more optimistic than starting a business from scratch with an idea. I mean there’s so many things that theoretically are stacked against you and yet it’s one of the ultimate acts of optimism. And I love to see that as people put in their blood sweat and tears to to move something forward and create. It’s an exciting place to be. So once you’ve done you know one or two angel investments, I certainly think, the bug bites you. And then once you’ve had a couple of exits, then you definitely yeah it’s a little addictive.

Jeffery:
Well that’s awesome. And so kind of like while you were going through and learning this, it sounds like and your father, Randy, was one I got to show him [sic]. Rudy.