CEO, Equation Angels

"Be strong in your goals but flexible in your methodology."

- Jess Joss

Jess outlines what she looks for in a start-up

Talk Takeaways

Jeffery talks with Jess Joss on her very entrepreneurial childhood and how this has help her become the entrepreneur and mother that she is today. She definitely believes that entrepreneurs need to have mentors. Ideally more than one since the cross-pollination of ideas is something that is really important and could potentially revolutionize the industry you are in.

As an angel investor, Jess looks into the team’s tenacity and the product’s market positioning before she commits on making an investment. On a pitch, while a product demo is great, she wants to hear more on the business plan and the business’ roadmap. This shows the entrepreneur’s foresight as well as the due diligence that was performed.

Jess finds that in both the entrepreneurial and investing world, at the end of the day, it comes down to your integrity and the relationships that you build. You need to be true to what you say you’re going to do and actually follow through. Aim to work together to collaborate and treat each other fairly.

About

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.

The full #OPNAskAnAngel talk

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. Work with him a while back. And I thought he was awesome like brought so much to the the atmosphere just when we were deep diving and everything to that effect. And what I found was that, and I’m curious, if this is what you found. Because you mentioned that based on the things that he did, you’ve got to learn from that and that helped you invest and you mean’t your mentorship and things like that. So was it pretty open?So was he sharing a lot of this detail growing up, so that you were like this is kind of cool because you mentioned today your son was, you know, running some charts and building some calculations on his growth of his business. So is it pretty open minded ? Is that the idea of of an entrepreneurial home?

Jess:
Yeah, you know interesting you say that. I think my first business was, before there were Costco’s etc, I was reselling candy in grade four at school, complete down to providing receipts and stuff like that. But you know the way I was raised, everything was incredibly transparent in terms of ownership deals. You know I also knew not to talk you know at dinner the night before the 15th of the month the 30th of the month. Because you know payroll in the early days was a problem. I had the opportunity, the thrilling opportunity, to plant the flowers in front of the business or help clean on weekends and stuff like that . So I know I was everything that’s incredibly transparent. and has always been when I was growing up. So I had a, you know a lot of sense of the ups and the downs, what it took, and I appreciate that now. I don’t think I realized at the time what a privilege it was to see both sides and to be included, I wouldn’t say in the decision-making per se when I was you know eight or twelve. But understanding what was going on and grew up with the business, I’m still to this date even though they have exited. I’ve still partners with employee or friends with employees, and partners from the original business and still see them. So it’s been you know built lifelong relationships but I definitely have learned, and I’m what I also think, I learned is a variety of perspectives, you know, I grew up in an entrepreneurial household with, you know, a particular bent but with the different partners, with the different people that I met through my formative years. I had a lot of opportunity to see different styles of Management, different styles of business and so on because we knew a lot of entrepreneurs. So you don’t realize how educational that is as a kid. Sometimes you’re interested it. Sometimes you’ve being dragged along because you know you’re needing a ride somewhere else but you know reflectively, I learned a lot at an early age or absorbed a lot, maybe, is a better way to put it. So yeah, so that certainly was very helpful and I’ve been incredibly transparent with my son in terms of what I, you know, we talk about. Like the portfolio we’re building, what type of companies, how manage an angel group, you know, by five he knew about patents and trademarks . It’s a hobby if nobody..[sic] You can love something but nobody pays you for it, it’s a hobby. And it’s only a company if somebody’s willing to buy it from you. And today was a lesson of ‘cost of goods sold’ and how do you have to sell at a certain price in order to make it a worthwhile business. So you know definitely a lot of open conversations. I think that’s important you know. And I do a lot of work volunteering, and you’ve done the same sort of thing where we work with you know high school or university students and I am so happy that they have access to early opportunities to explore entrepreneurship and business and so on. Which I think was not as available many years ago. And there’s so many interesting ideas being explored and learning at a really young age, and I think it’s a great opportunity because it’s also a mindset as well as a skill. So it’s seeing those opportunities. And I love working with you know university high school students etc and seeing where their mind goes for the future because they are the future.

Jeffery:
Agreed. And you mentioned that a few times that supporting the ecosystem or supporting small business is great for the country, it’s great for everybody to be able to come together, and one ninety seven, ninety-eight percent of the country’s made up a small business, you really do gotta figure out how to get behind it and it sounds like you guys obviously grew up in that mentality. You were starting companies when you’re a little girl, and you’re like hey I gotta sell some lemonade, I gotta make some money here. I love that. I can think back to a million things I did the same when I was a kid. And I’m not sure that you can just force yourself to be an entrepreneur, I think a lot of it is kind of innate in your ability to see problems break them down and try and solve them as a kid or growing up and you always hear those funny little quirky stories of what kids have sold and what things that they did and people got behind them. So, and one other thing I want to touch on because it is important and you mentioned it which was mentorship and it sounds like you had mentorship but was it something that was just provided in the family side or did you eventually grow into having other mentors as well, and make it part of your, call it your business portfolio, that you had to have a few mentors that helped you forward and is it something you would recommend to other startups?

Jess:
Absolutely. Yeah. So first of all I have I’ve had a wide variety of mentors with different skill sets and different act [sic], different areas that they excel in over the years and some mentors are continuing for many years and they’re more of a touch point, others are specific to a project or a business. I think it’s really important to have mentorship and I think what mentors provide is very invaluable. I also think it’s important to have that outside of the family because you have one, you know, I was very lucky I had access to a lot within within my family but there are different points of views and there’s different ways to doing things so I always see a variety of mentors is really useful. I like to solicit lots of opinions and lots of information and then create my own, my own version, my own plan, my way forward. So you know something I would definitely say to entrepreneurs is to have Mentors, but ideally don’t have just one. And the reason I say that is because your mentor may be absolutely world-class in that one particular vertical that you’re in but the cross-pollination of ideas, is something that’s really important and what works in the different industry you know could be something new and revolutionary in your industry and having people that are at you know, different stages in their own development and come from different backgrounds provides you with a real. really, sage advice and a real breadth. So highly recommend mentors. You can call them different things. You can call them mentors, you can call them business advisors, you know depends on how you’re structuring the relationship. Some people will say, “oh I want you to be on my board” and let’s take a step back from an investor’s point of view or from an interest point of view. Being on your board has a fiduciary responsibility to an incorporated company, whereas being an advisor does not, so you know I think for a lot of people, it’s a lot more attractive to be asked to be an advisor versus you know the fiduciary responsibilities of being a board member. But soliciting a variety of opinions, being able to brainstorm, and just understanding different aspects that you know somebody else has gone through and done the journey. As a teenager, you have your parents who are willing to give you a lot of advice and you don’t want to listen to it because they’re your parents and they don’t know anything. But you know in the business setting, why not take advantage of people that are willing to share some of their experiences and form your own version, the best hybrid version based on you know two or three different mentors experiences in your own gut. I think that makes everything stronger.

Jeffery:
Agreed. That’s great and it’s a good thing for startups to look at this as being a smart way to conduct business is to get information and and advisers that can bring in different perspectives into your fold, because your business is gonna shift and change every day, and having people that have different experiences they’re gonna help you with that.

Jess:
Absolutely. Makes you more resilient

Jeffery:
Agreed. Yes. And you need that big time. Never know what’s gonna happen in a day, tomorrow or what happened yesterday so you got to be ready for all of it. So In the scheme of the investing, you’re starting to jump in, you’ve done lots of different things, you’ve got deal flow, you’re starting to work on there. Is there a set number of companies, that you like to invest in per year? Is there inside your portfolio, you have an idea of every year I’m going to do X or is it not that calculated how do you look at your portfolio from that side of things?

Jess:
So the way it’s set up is I have two business partners and a pool of capital. We’re been investing for eleven, twelve years now. Twelve [SiC] thirteen years, eleven of them through formal angel groups. We’ve invested fifty five rounds so about 40 companies, 45 companies, 55 rounds. there’s not a set. So unlike a VC, there’s not a set number calculation of this much has to be invested each year etc and so on. So it’s partially based on opportunity, it’s partially based on bandwidth, at the time in terms of to invest takes a fair bit of time even if you’re doing it collaboratively with other angels, to do a thorough job of the due diligence, to weigh the options. So being a member of angel groups or multiple angel groups, you know you’ve got a fair bit of deal flow coming in plus you have the deal flow that you know comes directly to you, so assessing all that takes time and that’s a bandwidth issue. And then in terms of capital we divide it, so that there’s capital for new investment, there is also dry powder for our existing portfolio companies because you always want your existing portfolio companies to do well. And sometimes they need another route in order to be able to do well or you want to double down when they’re doing well. How many more cliches can I get in one sentence? That’s a lot there and so we don’t set a particular number right now, we’re in a point of we have a powder for additional, we are doing some new investment but a limited amount right now. We’re on the cusp of a couple of our largest investments are exiting within the next couple of months and that repatriates capital so that and you can start the investing again. And I think that’s something that you know everyone is building their own portfolio so it’s important to take a look at how 10 and 30 investments over the lifetime of an angel see a return on investments. We’d begin, two times, three times exit and you’ll have a couple that do well. So building a robust portfolio of companies that stages companies that are in different industries really helps sort of make your portfolio overall strong. People love metrics some people do it on gut, but there you definitely need to diversify your portfolio.

Jeffery:
Is there any specific verticals that you look at or have been looking at or is there something in your portfolio you’re trying to fill? So there’s probably some gaps, so are you looking at healthcare? What is your kind of now going forward planned and or what have you been looking at in the past that really interest you?

Jess:
Yeah. So I mean, if you look at what we’ve got, we’re vertically agnostic. We have everything from hardware to vodka tequila to Health to a horror film. So there’s you know quite a breath within that in terms of a vertical fill right now. When we repatriate, you know based on having that exit in the next couple months, I think the real focus will be there then is technologies or opportunities that help companies adjust and manage to the new to the new world order as it evolves helping them be more efficient and more effective in terms of delivering to customers etc. We have done limited amounts of pure health care, in terms of Pharma, we have one Pharma related one that’s a really long way that takes deep pockets, so I think, you know for us we wouldn’t necessarily go back into Pharma vaccine and stuff like that. But med tech, med tech is always interesting but our comfort zone is certainly our experience collaboratively as the team is pretty you know a lot more SASS-oriented SASS software, hardware that’s you know, a lot of where the background is. So as I mentioned before, if there’s an opportunity where a fellow angel is an expert within that field we would invest by doing collaborative due diligence with them so there’s a pretty broad range we have, you know, our companies range from fairly early stage post concept, post revenue, to ones that have gone public, to ones that are being acquired at a very high you know sort of very large very established companies. So I think you know the look the next one for us in terms of stage of companies is a little bit further along sort of post already post revenue post… post concept, post revenue, but maybe a little bit further along and getting into a really solid scaling position based on the stage of the company. But the vertical, we’re fairly agnostic and, frankly, a lot of it comes down to team. I think a team is sort of first and foremost, you know, sometimes you’re looking at a company, and team and market are the you know two things that are absolutely, incredibly important, Because you can’t you can do a little bit to tweak the team, you can do a little bit on the markets but the reality of it is the easiest you know part of the equation to adjust is the the product market fit adjusting the product if that’s the the type of company but team and the actual industry that they’re in those things are harder to to influence. So those things are the key components. And for us, vertical, or not into one particular one.

Jeffery:
Okay ,no that’s great and that you’re open-minded to other areas too. And you bring your partners in to kind of figure out what’s the best positioning work with the range of groups. So that’s a lot of great collaborating to make a great decision. So as an investor, it sounds like you’re kind of next play is going to be more of a series, a versus, a pre-seed or seed round or is it still kind of dabbling in a bit of all of that?

Jess:
I would definitely say it’s still seed round. Series A is a pretty deep pocket definitely seed round but maybe slightly later seeds, slightly more mature companies, that are closer to the cusp. As an investor, you know the earlier invest you’re taking greater risk but the price points lower, later you invest the price point tends to be higher so just to sort of round out the portfolio that we have we’ve got a lot of early-stage ones, we have a couple exiting so sort of that sort of later that mid stage is probably where we you know collectively need to be within our portfolio. Yeah.

Jeffery:
Okay no that’s great. You mentioned that you have follow-up investment which is great, having that process involved, it really does help. It gets other investors interested as well because you’re falling on to investments that you went into. Do you have any preferred materials that you look for when it comes to the DD side either on documentation or on team, like is there anything there if you tie that all together? These are must-haves. They’ve got to be really awesome and I’m looking for these things.

Jess:
Well, I mean a full due diligence room is something that I don’t think any entrepreneur should even go out and start having the initial coffee dates without. I used to hear a lot that angels were very slow and when you dug into the process, angels, in you know people that were saying, didn’t have a full of completed due diligence, didn’t have all the documents together, they didn’t have the financials and so on. So due diligence can be fairly efficient when you work together as a group. If you’ve got to populate the due diligence room, yes you need to check certain things you need to do your behind-the-scenes due diligence but I think a lot of it is meeting with the team, understanding the strengths and weaknesses within the business and really walking through that. So that’s a deep dive and then some of it is the research that you do on your own. But yeah, as an entrepreneur if you’re getting ready to ‘raise’, your due diligence room should be 99% completed. Before you even set foot outside to talk about the fact that you’re getting ready to ‘raise’ and easy enough you can Google, you know it’s pretty easy to Google and find out you know, what a standard due diligence room is, but sometimes it’s just a matter of collecting a bunch of your documents and getting everything up to date and having some rejections ready and so on and then build from there. But for me as I mentioned before, you know, team is certainly something that’s you know really important . if it’s a product, obviously you want a product demo. And I would clarify for our entrepreneurs that a pitch is not a product demo. It may touch on some of the product elements but it is certainly not. The pitch is the business plan, the pitch is where you’re going. And I’ve seen so many people get bogged down in the process of presenting, and all they want to do is they want to tell you every single feature that they’ve ever done, yes, but that’s not your business. You know that’s how your product works. But if I’m doing due diligence, I do want to see all the nuances of the product and you know sort of kick the tires so to speak but that’s not for your initial pitch. But again you know I would say team is you know number one ,foremost most important .

Jeffery:
Brilliant. So you look at the team, you’re ready to go, is there any format that you like? You like preferred shares, do you like safes? Is there something that kind of really tops it off? Or you put the entrepreneur? What’s the [sic] how do you look at it that way?

Jess:
Majority of our investments are preferred shares. Preferred shares with incentives for the entrepreneur. Personal opinion is that you know, safe tends to be for very early-stage companies and works really well in an incubator accelerator format where you’re putting a lot through because I tend to invest a little bit later on where it’s post concept post revenue. Safe is not necessarily a solid choice for us. Yeah we have done some convertible but pref shares is, are, a real happy zone.

Jeffery:
I like it. Yeah noted. So that’s that’s great and some good feedback is there I guess when you’re working with these startups, do you take a leading hand in maybe leading around or even before that, you jump into working with the entrepreneur to help them and mentor them through that process so that you get to that end goal. Is there, are there other ways that you look at outside of just investing in money? Is there other things that you try to do with the companies you work with?

Jess:
Yeah so I think you know as an entrepreneur, when you’re when you bring on an investor I think it’s really important to engage them, and engaging them can mean many different things. Some advisors will have or investors will have a great knowledge of a year specific industry but others will have a great network that you can tap into. So you know there’s different ways of looking to engage your angel investors. From our point of view, you know, we’d like a board seat but the board seat doesn’t specifically have to be us because as we invest through an angel group it’s somebody representing the Angel interests although their fiduciary responsibility becomes to the startup. So you know different companies have different roles. If there’s an area of expertise that we can bring on even without a board role but being an advisor based on some connections, or things like that we’d like to bring that to the table. So it’s a case by case scenario whether we add value. No one certainly myself or my partner’s, we’re not ever looking to distract the entrepreneurs, we’re adding looking to provide opportunities connections value and so though it depends on the industry and the vertical, There’s some where we just have, we can do some introductions but beyond that we don’t have a lot that can move that company for. If and then there’s others where we’re yo know one of my partner’s is incredibly entwined and they’re you know two days a week and helping walk it through to what’s going to be you know their exit come this all. So it depends on a particular case but I think it’s one of the values again collaboratively investing with other angels is you always have that touch point you know that there are angels you know, somebody’s on the board, you’re they’re [sic] sharing different perspectives within the board setting. And I think that’s important so as the decision-making goes forward and the company moves from startup to scale. I think it’s good to have people with experience from various stages.

Jeffery:
That’s great. You mentioned one thing which was value, so there’s obviously good exchange of value you’ve got it done through this ecosystem of our system if you will, of looking finding investments, figuring out how you want to work with them all the way through mentorship, supporting them, board seats and now you’ve kind of decided you know there’s a value here, I can help out. Can you look back at all of the companies that you invested in, worked with, had a touch point with, and can you pick out maybe one or two things that you really think stand out and why these companies eventually became successful?

Jess:
Yeah. So I mean I think if you [sic]… tenacity of the team is certainly something that just [sic] it can be very challenging to see a company through to the growth cycle. But having the industry knowledge but also be strong in your goals but flexible in your methodology and I think that’s something, that for sometimes for entrepreneurs can be challenging and the ones that the succeed really well do have that and what I mean by that is as an entrepreneur your company’s your baby, and your startups your baby, so you love it but being objective enough to see you know where you want it to go but being aware that the path you know based on research dialogue etc you may be on a path and realizing that a pivot it would be appropriate for your company and sometimes people have a hard time taking that objective data because the company has become their baby. So you know the entrepreneurs that are very strong, that can see a different way forward, to get them to the end goal of being what they deem a successful company but that there might be a slightly different path for them to take because there’s been an evolution within their ecosystem, within their industry. So I think people being open to that, that’s a strong skill set that I’ve certainly seen with you know with some of the more successful entrepreneurs. And I think you know another example of one that’s been and I’ve seen that you know in that company went public and they were very [sic]… the leadership there from the original founders was very strong but they also were very good about taking advice from people that had maybe from different industries but they had gone public before different things like that and I think that allowed them to be much savvy beyond the years of the company because they had that collective wisdom and they solicited it. When I look at some other companies I think, ones that have actively communicated and engaged with their investors have really benefited from that and so I can think of you know sort of two examples there one would be a company that I met at a conference, over you know a buffet years before they were investable, in fact they were just you know literally an idea on a napkin. But that entrepreneur forged a relationship, and this was pre-investment. By every quarter keeping in touch, giving an update every time they said they were going to do something, this was the next step, following through except and so on. Not in pushy way, not in an aggressive way but really built a lot of trust and a relationship and I knew this was someone that was determined and dogged because that continued for three years and when I ended up investing they were still a little bit earlier, it was a small amount, a little bit earlier than I would normally invest but the reason I did it was they built three years of trust and I you know and I really felt strongly that they were going to do everything in their power to continue to be a success and grow. Another company you know I think has utilized another portfolio company that I think has utilized their investors really successfully was all of their production was in Asia. and in late 2019 they started to realize that they were going to have production issues and very quickly reached out to their angels and their investors to look for local production opportunities found we’re able to reach will find everything locally and because of what they do in terms of the sanitation of cell phones and tablets in hospital school of sick settings except etc. The pandemic has been a real boon for their business and they were able to control their supply chain have it local and the introductions all came from all the local suppliers accept, or came through their Angels, and came and because of the introductions they were able to very quickly jump on those relationships and move forward which has been invaluable to the growth of their business over the last couple of months. So you know wise entrepreneurs, engage with their angels, they actively ask for not day-to-day operational help necessarily but insights and then they tap into them and continue to keep them in the loop and I think those are the partners that have seen great success.

Jeffery:
Oh that’s great. You make a great point, is that if the entrepreneur is willing to be open minded and listened to their audience, they’re also open minded to dive in and learn more from the people that have done that before, so the more questions they can ask, the more benefits they’re gonna get from it. So there’s a true value exchange there for sure. Is there, along this journey you’ve been on, has there have been one great story that you’ve got to tell about a startup or an entrepreneur that you thought just beat all odds and really just knock down doors and this I don’t know it could be anything I’m just a great story that you think that just really emphasizes the struggle but the wins that an early-stage company can go through ?

Jess:
Well, certainly I think Clean Slate which is the tablet cleaning tablet one tablet and cell phone cleaning one. They had, you know they I met them initially as a pitch competition through a Queen’s University summer build a business program. So you know they kept in touch, they were able to incorporate, they you know patent technology etc and so on, so they did a great job that way. And now their timing, its right so they have really they were well structured well placed and they were growing well but the market changes for them, in terms of what’s happened globally, has been really beneficial. In terms of other ones I look at one that we’re in that’s in health we’ve been in that for a while, it was a company that I had been around longer so the investment was probably it was above angel level you know, as in like post a million versus you know blow a million. But it it has been doing roll up, it has acquired another one of our portfolio company. It has created some very strong relationships with some other ones. So they’ve really become their strategies to become a full suite of product focusing on health working very closely with governments and and so I their exit I think will be substantially stronger and this is one that all you know we hope that’ll exit in the next little while. And I think it’ll be substantially stronger because they realized they couldn’t do everything themselves internally but they found some other great complementary products and tools, you know tacked them, brought them together so they became a one comprehensive solution and that from a purchasing side on a government is one-stop shopping one group to that. So I think that was a really strong strategy and I’m really excited for them because they’ve put in so much hard work and it’ll be I look forward to seeing them reaping the rewards that they deserve not just financial but also I think you know the full acknowledgment of what they have really built as a phenomenal system so you know you’re proud of different portfolio companies, for different reasons you know you just want to see them succeed, invest in them because you believe in them. There’s a lot more impersonal ways to invest. So you know I think there’s a relationship to be had with every entrepreneur and you want to see them succeed and some do well, some don’t, some do better than you expected. So it’s nice to see the trajectory and those that have really gone above and beyond to see it come back to them.

Jeffery:
Well said and yeah I second the motion. I love that. That’s great! So we’re gonna jump into more of high in the sky crystal ball kind of thing so is there any predictions that you can say that you feel they’re gonna happen over the next 12 to 36 months? Where do you see the world kind of shifting, where we’re going through obviously this pandemic it’s shaping up, it’s getting better, you know where do we net out in the next 12 months from an investment standpoint, and then where do you see us in the next 36?

Jess:
I think you know from an investor perspective, so first of all, a lot of people as you love are doing their initial screening remotely using technology. S0 that’s something that allows for an element of efficiency. So I think that you’ll find that a lot of organizations are doing a lot more virtual in the early side of the pitching, and even when COVID restrictions are loosened I think that you’ll see that a lot more will remain virtual that having been said, I do think that you know Angels as a whole, those that enjoy angel groups, also enjoy the networking etc so I think there will be opportunities to not every pitch competition is going to be virtual for the rest of our lives. So as I look going forward, I think that there has been a right sizing of start-up evaluations or there will be that might be a controversial opinion but I think that when we look at our eco-system and we’re looking at Southern Ontario, it’s not necessarily the same as being in the valley and but valuations definitely have been creeping up and I think that you know it’s a strong time to invest as evaluations are going to be a little more or one might stay realistic there and depending on how you look at it. I think that, as well by and large I think angel investors saved you know investors have been around a long time will see an opportunity and investing in a period of time like this whether it’s the better valuations, whether it’s realizing that there’s an accelerated innovation cycle going on right now because we have to and people are forced to change the old habits and adopt new ones. So you know there’s a lot to be said for investing in this time. I think the initial wave of investment will probably be, you know angels will look probably first to their portfolio companies to make sure that they have been able to help their portfolio companies because you’ve already gone in on that once, you want to make sure that they succeed. So I think that’ll be sort of the first priority in terms of investing and then I think the next area of investment is likely to be ones and I touched on this earlier but companies that are helping industries adapt to whatever the new norms are going to be so in terms of delivering the products and services in a way that is more efficient, perhaps socially distanced, perhaps rejigging their model in order to be able to do that not you know that’s not applicable to a services business you know your hairdresser is going to do things under new guidelines but it’s not going to revolutionize their their business industry but there are going to be industries where they will never go back to the old way of doing things. And so a a product or something that helps them adapt to this new world and be efficient and effective and move forward I think is a great area. I think that there’ll also be investment in healthcare, in terms of you know whether it’s devices, whether it’s testing etc. and so on that’s not mine, necessarily my area, but I think that there will be angels that definitely see this as an area world solutions. You know the greater good and investing in that area. So I think that’s one that will I think probably medical devices and personal protection and different things within background will be areas that you know initially will be of interest because people can see how they are applicable when it comes to investing you know you’re looking for a company that fills that need that is the category killer in a particular area and you know right now there’s a lot of opportunity for companies to have first mover advantage and really come up with you know come up with nimble solutions. Right now and I think that’ll be attractive to angels and then as you know we look further out and we’re looking we’re at 12 and we’re at 36 months, you know I think the things that we’re gonna look at is, as an angel, I still have to hold to my portfolio stance and what I mean by that is that you know the 10 to 30 companies, the different stages, for us I use different verticals, some people go deep into one vertical. But you still have to come back to your thesis and so as an investor I still have my thesis in terms of the age stage where I bring value and what I’m looking for so I think that people may vary their verticals and they may vary the stage that they invest out a little bit right now, because we’re in a, it’s a unique opportunity and a unique time where there really is an opportunity for nimble startups to excel very quickly but I think to some degree. People are going to return as investors to their original thesis because there was a reason why they had that thesis, why they we always have to update our thesis, we always have to continue to educate ourselves but there is a stage or a vertical or a way of investing that works for an investor’s portfolio and I think that you know those elements will continue to be there.

Jeffery:
that’s great and it does sound like there’s gonna be some pull back to learning, seeing what the landscape is like and then kind of jumping in to the opportunities that are going to help expand in healthcare or in areas that are self protecting or businesses that are looking to be remote.so there’s gonna be a lot of tech plays. So that’s great, great insight. Is there anything that you would share out to the entrepreneurial world or even to the investor world, some final thoughts and comments too as we all are big cheerleaders for the startup communities, is there anything you’d like to share that you think to kind of end this off from from our time spent together?

Jess:
Thank you. I love this ecosystem and I love it because of the dedicated optimistic people both on the entrepreneurial side, on the accelerator and incubator side, and also on the angel side. I fundamentally come out everything from a relationship perspective. And so I would say that both for the investors and for the entrepreneurs, the relationship should build your reputation. Your word and how you interact with people follows you throughout. It”s our investment community whether it be Southern Ontario whether it be Canada and it’s a fairly small community and I think it’s important that we work together to collaborate. We treat each other fairly and we look at everything from a win-win in Pollyanna as it may be, but a win-win opportunity because we’re partnering together, angels are partnering together, angels are partnering with entrepreneurs. So I think it comes down to relationships and acting with integrity and being true to true to what you say you’re going to do and I think those are the sustaining relationships. So you know, they [sic], you may reinvest in a second company that the person does because of that relationship. You may find angels that you really enjoy collaborating in, co-investing with because of that so how you conduct yourself and being true to you know your values and how you treat other people carries you through every aspect in life and includes you know starting a company or investing in collaboratively.

Jeffery:
That’s brilliant. I like it. And to end on that note I’ve taken lots of notes which I always enjoy sharing because people might be wondering why I’m like head down and because I’m writing like crazy but I haven’t found a way to stabilize this table yet but I have found a way to keep writing quickly but I do appreciate all your time today, Jess. I enjoyed actually, I will probably send you a message and tell you that this take didn’t work just so that we can talk one more time.

Jess:
I know my answer will get better and better. By the third take it will be even better, right?!

Jeffery:
But it was brilliant and the video came in perfect. So I’m glad you came to network so that was awesome and I really enjoyed once again getting to learn more about you and how you work on the investment in the entrepreneurial side. It’s been fantastic, so thank you very much again for helping and joining. It’s what we’re all about and I’m glad that we got to learn more about you and we will share that with everybody in the upcoming weeks we’ll share more details back

Jess:
Well, I’ve always enjoyed collaborating with you. You are an ecosystem builder and a connector which is the areas I love to be in. So I look forward to our our paths crossing again in person I know you’re loving being behind a laptop, I’m looking forward to the in-person side of it and I will see you again soon but thank you for this opportunity. It was a great conversation and always fun.

Jeffery:
Awesome. Thanks, Jesse. Have a great day thank you.

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