"Mentoring is a mindset. Being a student of life, being a student to give openly, and willing to receive information, and to process it in a way that is going to either make a change for you or what the job you’re trying to accomplish."

- Jason Daley

Jason outlines what he looks for in a start-up

Talk Takeaways

For this interview, Jeffery Potvin talked with Jason Daley and explored the topic on mentorship at a whole different capacity. To be a student of life and how mentoring has the power to really propel an entrepreneur forward. One of the main takeaways of this discussion was on building relationships. For the startup team, when risks are mitigated and the team is aligned in their expectations, the business execution can be a successful execution.

His insights on artificial intelligence and augmentation as one of the verticals opening up in the next 12 to 36 months are interesting and worth looking into.

About

Jason is a venture catalyst and portfolio entrepreneur with a unique talent for the Art of the Startup. His talent manifests all the business essentials around a great idea and bringing it to market by leveraging his business acumen, strategic connections, and his exceptional talents. Honed over 20 years of professional experience in a multitude of high growth industries with an emphasis on Media & Entertainment, Web Technologies, and Real Estate. Jason is a proven catalyst to help clients achieve their business goals, he is also a sought-after advisor, community builder, angel investor and speaker in the startup community.

Jason is a recipient of Ottawa’s top-40 under-40 (2012), multiple Bootstrap award winner and has received Invest Ottawa’s Rising Star CEO Award. He’s also received volunteer service recognition from Carleton University’s Student Association, Alumni Association and the Sprott School of Business.

Core Competencies:

  • Business models, planning, value propositions
  • Venture financing, investment, deal brokering
  • Branding, Corporate Strategy, Communications, Go-to-market plans, Business and Partner Development
  • Pitching and public speaking
  • Sales Funnel – Lead Generation, Business development, Sales closing
  • Integrated Marketing (design and execution) – Traditional, Guerrilla, Social, cross media, PR, large scale event mgnt, advertising, sponsorship
  • Film/TV/Web production

The full #OPNAskAnAngel talk

Jeffery:
Okay, awesome. Well welcome everybody. We’re super excited today to have Jason Daley on AskAnAngel. So, Jason, we like to jump right into things so why don’t we just throw it over to you. Maybe you can give us a breakdown of kind of where you’ve come from, a bit of your past, middle ground, and the future of Jason and all the great things you’ve been up to.

Jason:
Yeah, happy to do so. So I started in technology domain as my career back in the 2000’s, you know, the bubble when we were building the infrastructure. I worked for a company that was building the wavelength switching, allows us to have, you know, video on our hand devices now and that was pretty novel then because I had to learn about how you built the infrastructure, all the protocols, the wavelength switching, and they gave me a big thick book with the ISO model and said, “You got to learn all this in every chapter. You’re going to talk to another engineer in the department and you’re going to get the deep download”. I was the eighth employee of the company. It’s called Meriton Networks. It grew and scaled up to 250 and I was the emcee of the Christmas party. And I always had mentors along the way and that’s actually one of the most beneficial things I’ve found throughout my whole career. It’s definitely a theme. You probably… so talk to that later on but the fast facet there was I learned what technology innovation looked like, how it got funded. I was the executive whip boy (self-described) that I wanted the hard project. I wanted to dive in deep and support what was going on under this machine, this bubble that was bursting open, and ballooning, and we’re scaling. I wanted to understand all the mechanics underneath it and that brought me for almost close to three years. They had an exit to Xtera public company. Although, they were three years too short of when one of the major telco companies were going to be changing out their infrastructure and putting in this new equipment. So, it was just a little bit too soon. The burn rate exhausted and they had to basically go around and say, “Hey, we have to really shore up the business. Do you mind taking a package?” And I was so disillusioned, like, what? I was seemingly fundamental to the sales the marketing. I opened up accounts with 27 different major Telcos to get our series B round and I was just like, “What are you serious?” I understood now. Being a manager, being a CEO, there was families that had to be taken care of. There was critical technology had to be delivered against SPEC. And I was in a unique scenario where I was transitioning to a national sales role but I didn’t have any accounts. And so it put me into a scenario where I had to learn to be humble. I had to learn what matters. Let the technology and the customer had to be served. And so I didn’t realize that until I started doing my own business nine months after. I jumped into my own practice of doing consulting, helping innovation get deployed within different environments. That, let’s just say I thought I was gonna go sell the tech. But what did I do? I had mompreneurs. Some of my first referrals were an author and she enjoyed the working relationship. But I had all this blue chip training and I’m trying to fit into mompreneur, who’s only got so much time, it’s a side hustle, she wants to make money, and she knows where she wants to put it, but I can’t take all the tool sets I was working with. I need to put it into something that’s going to work so it came down to fundamentals. It came down to the value proposition, boiling it down. And when I discovered C case and all that work around, the lean startup, and the business model canvas, it just opened up more where that’s where I had to go. I needed to go help take great ideas, great founders, and move their ideas to market. And now the tools are there readily and the cost of starting a startup are vastly lower than trying to build, you know, an infrastructure tech company that required, you know, close to 90 million dollars of funding throughout. Where now you can do this for sometimes under ten thousand dollars. You can get a decent business opportunity where you can start generating at least a little bit of revenue. And from then, I discovered that I’m going to do some investment where I see the best and brightest ideas. I’m going to put some my own dollars and my own capital behind it. Yeah, so, that was maybe about a decade ago and that’s how I stumbled into it is based on doing consulting. I felt that I could work with some of the best and brightest. But I got us I got to do the sweat under the caller. I got to roll up my sleeves. I got to be in the fire. I’m on that founder’s journey with them and that’s been my my career ever since.

Jeffery:
Oh, it’s amazing. So, if you take your past experience and the last 10 years, it sounds like you found a really good solution on how to work and operate as a consultant/almost operator with some of these startups based on your earlier experience. You mentioned one thing that’s really fascinating and I always got to go into the subject, which is mentors. And you mentioned that you started off having mentors. Can you give us a bit more understanding of what mentors were able to help you with and where that helped you move into where you are today?

Jason:
Yeah, I appreciate that question. It’s something so important to me. I’m with the executive at Carleton University. I’m on the alumni and we created a mentoring program just to address this challenge because at a university, it was not easy to find someone in the industry to be mentored. And what I end up looking for out of my first starting career was someone that had a skill set that I knew could be really impactful, internet oriented, how do you take technologies and implement them. I got two offers I was told by my my parents “Try and find two offers to know your value. Know your worth so you’re not having someone dictate your worth.” You get the market to do so and I end up getting offered from Export Development. I did an internship for six months and I could be supporting a country/regional manager doing risk assessment. This has imports to what I’m doing now. But I also got an invite by a mentor who is doing internet marketing, James Madue, and it just seemed so important that I get involved in something that is going to shape fundamentally the way we are going to interact and do business in the future. And so I took ten thousand dollars less, right out of school, with debt, to be mentored. Like, I took on the chin right then and there that this was the time that if I’m going to make any grade in the technology I got to learn from someone who’s leading the edge of that curve and that’s why it’s so important to me. It’s the mentoring. So, you get mentored and you should mentor is the way that I look at it when I’m in a career like this because there’s always someone who has a skill set that can offer more experience and more insights that gonna help you navigate your path forward.

Jeffery:
So, when you reached out and took this role with the mentor, did you kind of foresee where you wanted to go with the mentor? And were they able to help guide you through that? Or were you kind of leading the charge and they were filling in the blanks as you moved along?

Jason:
So, how we made arrangement with the mentor early in that relationship was that, from the offer I had it included that I would have a book meeting, 30 minutes Friday lunch to be able to have discussions about not just work. It was about what I see in the business and what I wanted to understand. We end up being every two weeks, which was more than enough because sometimes it stretches to a full hour. And so, I put it into his calendar. I was pretty brazen to asset of a senior manager VP level but he was going to lean on me and I was head-hunted for my previous job and he said, “Okay. I’m going to take you under my wing and we’re going to expect a lot out of both of you, one another”. And so that’s… I mean I led some of it but then the discussion came inside of it is I need to learn what is my missing. I come from a business background but I’m in a technology domain and every boardroom I’m in is always talking about the advances of how this technology is differentiated from the next. So, I had to get schooled and so he would assign me time to talk to the product manager some of the engineering and later on it ended up becoming part of my unique relationship while I was an internal informal conduit of information. Before you know, the quarterly updates were pretty typical. I would be providing some informal updates, different team groups, or I’d be assigned by an executive who’s on travels. “Get Jason to sit in the meeting and provide the update”. And as a 20-something, that was really a valuable experience that I never sat alone at a lunch table. I was always getting harangued and asked about where directions were heading and that was beneficial because I learned by the experience of connecting with my colleagues. So, that to say sometimes your mentoring relationships are also to the left and right of you as you work with teams and colleagues.

Jeffery:
So mentoring comes from everywhere then. It’s not just that you have to go out and try and find it but there’s mentors out there, even if they’re sitting in front of you, working with you, you’re going to learn something from everybody. You just got to be open-minded to it.

Jason:
That’s right. Mentoring is a mindset. Being a student of life, being a student to give openly, and willing to receive information, and to process it in a way that is going to either make change for you or what the job you’re trying to accomplish.

Jeffery:
Well, I love that. And you mentioned that you started a program with Carlton University. Is that around mentoring? Can you give us an idea of how that looks, and what it’s about, and how it came about?

Jason:
Yeah, there’s two aspects that I helped. One is the university alumni program that has 80,000 alumni around the world were all invited to be participating and to put up their hand that they would be an alumni mentor to a third or fourth year student. It was put into a software system so they could be done through matching but they finessed it with personal hand matching, which was something I felt was important. But it was managed through a process of understanding that — here’s the guidance and here’s several different interaction points where it could be facilitated with in-person mentoring. And mentors met other mentors so there’s professional networking development that provided a benefit that for everyone so that collegial and that student mentor relationship. I went a little step further and I helped to also spawn a incubator for young entrepreneurs at the university. It was called Hatch and it was for the student, just like me, that didn’t want to go to the university to get a normal job. I wanted to create my career. I was an entrepreneur and I didn’t see opportunities. I wasn’t getting recruited at that point. I had to go find opportunities and I wanted to replace those missing elements and help bring something to Carlton. So, we worked with the student association. Shout out to Fahad Altab. He was the president of CUSA and we came together with another student director, Renee, who went on to work with Startup Canada and we put together a program that was providing a weekly get together, a brown bag lunch series education, and I was doing full Thursday open office hours. I was meeting every half hour mentoring the next entrepreneur on their businesses. And that was just important to get it going the first year to show that we have businesses that can be built by students in a safe environment, less risk, access to academia, lots of mentoring, and the talent pool is their friends and colleagues. They get really excited about it. And we wanted to light the fire to hatch the possibilities. And now that’s been running now. I think it’s in its sixth year and a lot of campuses have them now and I’m glad to see it. We took notes from other campuses so it just takes a lot of time and effort to lift a new concept inside an institution. And now that we’re in the world where technology and tools are readily abundant, it’s really important to build an ecosystem, especially inside a university as it’s so integral to how startups get launched and the technology innovation that’s required.

Jeffery:
Oh, that sounds amazing and congratulations on setting that up. It’s huge.

Jason:
Thank you. Appreciate it.

Jeffery:
Is there some metrics that you can take around this? Because then, when I like to explore this mentor piece, I’ve had mentors throughout my day but I went to them and said, “I want.. you know, your marketing, I’m not. I want to learn about marketing so can I be you be my mentor?” and I did that at different places throughout time. I only had one person ever come to me and tell me they want to be my mentor, which I thought was phenomenal. And he was a lawyer and Chris was an awesome guy and I remember that when he just flipped me over and said, “Go look at this book”. So, when I pulled it off the shelf and he’s like, “What do you see in there?” and I’m like, “Uh, it was a hockey card. It was a goalie” and I’m sorry I was a baseball card. And he says, “Well that’s for you”, and I was like, “Okay”, and he’s like, “You know what, I want to be your mentor. You’re going to run a big company. I need to be your mentor”, and I was like, “Okay. I don’t know how this works. Sure”. And he was phenomenal. I learned a ton from him. And so, what you’ve been doing with the students, do you see any metrics where I already have any metrics that with this connection process that’s occurring, is there a lot that you’re seeing these students? Come back and say, “You know what, I learned a lot but not only did I learn a lot, I made some connections. They helped me get into this space more”. Like, what are the the KPI’s that you get out of this because for me, I think it’s an untapped space that people really should look at, trying to figure out can I be more tactful. Just like you’re gonna find an investor, you can find someone that can mentor you in a space you don’t know a lot about. And even like you said a half hour or an hour every two weeks is more valuable than hiring somebody to work for you to do a certain job. I’m paraphrasing for you but you know, do you have any KPI’s that really knocked us out?

Jason:
I wish I could offer more KPI’s. Our program, at least with Carlton in the mentoring program, as a recommendation of a monthly meet, my communications with my two mentors they they always assign me the young entrepreneurs to be mentored by me personally. I ask for it. I want to work with them because they… you can’t replace fire in someone’s gut. So if I could put a KPI for that, how bad does that burn inside of them where they just cannot extinguish it no matter what the rest of life will try and extinguish that burning desire of an entrepreneur’s heart and that passion. I want to provide them more fuel and more flame so luminous, you know. How luminous is that fire in their belly? That would be amazing, but I look at it ways to the way their character. I look at how they interact, what matters to them, why they commit themselves to certain volunteer activities. If they haven’t done any, I say go look at a few of them and tell me what might interest you to get involved because part of your role in university is the relationships you make and mentoring is just one. But the breadth and long standing relationship you’ll hold the rest of your career can start in the university environment. And the best ways to do it is to align on a purpose, on a activity, or a mission often around different student groups and activities and that’s where you can find those lifelong relationships you can leverage throughout the rest your career. So I’d often say find two or three of those type of groups and tell me why it matters to you and then we can orientate some of our conversations about getting involved there or how you get involved. But we also had Hatch, which already had a group getting together every every week. And so that became a metric about showing up. So much about business is showing up, you don’t have to have all the answers, be open when you don’t know, and ask the right questions, so that you learn as you go. And those are sort of the composites of you know what makes a good metric but meeting regularly really helps build a cadence and to get ready and be prepared for that opportunity. I highly recommend when you meet your mentor, think about it ahead of time, prep your questions, be more insightful so that you can get the most of that dialogue.

Jeffery:
And verify the fact that you’re using somebody’s time so go there with all the hard-hitting questions so that you leave with something of value. It’s like booking a meeting. You have to have some ask in that meeting and if you don’t have an ask then ask to be introduced to somebody. There’s always a positive that you can take from anything that you’re going to do with someone. But I do like the that whole aspect of preparing yourself before you go in so that you come out with an end result that’s going to bring value back to you. And it might even bring value back to your mentor as well.

Jason:
I’ll put a point of reference for that alone, Jeffery, would you say about this value exchange… sort of the law of reciprocity and something that I sometimes speak to with my mentorees that you might have um a grand vision and a whole lot of energy put towards achieving that you just feel impatient on how you go get it. But don’t forget there’s steps along the way and when you are leveraging someone’s time, or resources, or network, value that and there’s certain things you can do. And I’ve had even some of my tenants, my real estate property so I use that as a way of doing investment to normalize the ups and downs of startup and tech investing. But I even had mentorees inside my properties because I wanted to be close enough to to see them through their journey even though they weren’t in my university. So I didn’t want to say “No, you’re not in my university. I can’t be available to you a mentor”. But if they happen to be looking for a property I put them in and they, even to this day, three years had it’s been the top number one sales in scholarship service painting. For three years, he still does a job every year to say thanks. And it’s like, he trains his staff on one of my properties. That just… it just… to him, it makes great sense. I go over. I spend some time. I’ll bring some, you know, food or lunch and you know. But that relationship has been established on a foundational reciprocity. And so, maybe everyone else who’s looking for a mentor might find something that they’re already doing that could be valuable to their mentor.

Jeffery:
No, that’s brilliant. And I’m a big fan of “Everything you do in life is a value exchange”. Nothing’s for free, but you got to find a way to give back and take at the same time. It can’t always be take. But I like the fact that people are repaying back the same thing when they’re working with you that they’re seeing the value and they’re continuing to kind of flourish it but find ways to keep those touch points. And I think that’s pretty valuable. So, you’ve kind of gone through. You’ve built this. Now, I know you’re doing a lot of unique stuff as well with startups so maybe give us a better idea or a bigger idea of the whole startup ecosystem in Ottawa and how you’re working behind that. So, I know you work with a bunch of different groups and there’s a lot of exciting things that you guys are doing.

Jason:
Yeah, thank you. Well, the way that I work within the auto ecosystem is I have a mindset. I put roots into the ecosystem first and I nourish them before looking to have anything in exchange back. Give to your community the resources will be more robust and available to to you later in later on. And inside of that… So, I’m on the board of the Ottawa network. It’s about supporting founders in their early parts of their journey as they come out of the their early stage where they have their ideas and their prototypes. They have an open demo night that we host every every other month. So we have one coming up in july 30th. And I look for talented founders. Have a discussion with them and then give them the floor and it’s it’s a very much a nurturing space. It’s about helpful feedback and understanding where this person has this idea and where they’re coming from and where they need to go and we, that community, is offering some supports and where need to go. I’m looking for a raise or needing this type of talent to be working on my project so there it’s an ask of the community to help. And I really enjoy the the demo nights. I know you do them as well. They’re always some of the most exciting aspects of coming out on an evening when you’re already busy tired from your day’s work but you get refreshed from people presenting their hearts and their businesses. I’ve been involved through Carlton’s startup ecosystem, Hatch entrepreneurs, young entrepreneurs. They naturally progress either into lead-to-win, which is a more codified university accelerator. And then, they’re also referred and matched over to invest Ottawa, which is our RIC or Regional Investment Center. And inside of that, they get more resources that they need to cement their businesses and to move forward. Selectively, I work with founders that have needs in ways in which they either need a three types of capital, which is what I do as a venture catalyst — is a term I use. I work on that early founder stage where you’re getting your concept together, to prototyping, to first customer traction, then your growth being investment ready. And I will invest my network, my intellectual capital, my network capital, social capital, and then my financial capitals as a hurdle. So all that time I’m in alignment, I’m working on your project and I’m not taking any fees until there’s a milestone that a hurdle rate where my time and my money are viewed by a third party or another Angel Investor and that becomes full sweep. So it means I’m on your journey. I’m not taking early stakes unless we reach a milestone that is a major one and it has validation from another industry associate. I had to learn that was the fair process because I would often lose out on promises or businesses not coming to fruition. But I love the grind, I guess. It’s not always my wife and family but I love the journey and learning the experiential learning. So, I’ve made this model. So, I’ve done now closer to nine/ten different investments, mostly of that sort of description and it was important to me that I build trust with my network of those that want to invest alongside me because I’ve done the preparedness and the some of the diligence work and the guidance to get the company forward.

Jeffery:
No, that’s awesome. And I like the fact that you mentioned that you build trust. I think a lot of people tend to just jump into something thinking that they’re so valuable that they’re going to get a lot out of this and the other person should just believe them. And there’s a lot of in this space a lot of people that are just looking for equity and they walk away or they don’t produce anything and they just want the chips and then they leave. So, I like that I really like the fact that you’re in there. You’re doing a lot of great work. You’ve got a couple of different verticals or buckets that you’re focused on. And money’s the last one because you’re trying to build and get into there so that you really believe in their vision and get behind them and then you start to produce the other aspects. It’s going to help them bump their business and grow it. So you really are… you’re almost the CEO helping in, doing all the right things, and then, at the right time you’re you’re also saying, “Hey, wait. Don’t sweat it. I’ve got some cash. You want to put into this too”. So, you’re really bringing a lot of value into that game.

Jason:
Yeah, yeah, thanks for saying that. You know how hard it is with all your work that you do with OPN. Just getting to the milestone being selected by OPN to be pitched. What happens everything leading up to that? Maybe you’ve never had the experience. Maybe you’re so passionate about a problem you want to solve but you don’t know the ecosystem. You don’t have the connection points. You don’t know what’s expected. It is pretty daunting task. Leading up to that first night where you’re going to pitch in front of a whole room and deliver, right? That takes some coaching and mentoring so that’s going back to our early conversation. That’s where I started from it. But I had some wins. I work in innovation. I work in technology. And when I have wins I keep dry powder aside waiting for the right thing that’s going to be fitting. So, I have two current files that I’m really excited about and my scope of work always gets bigger in terms of the opportunity. But then, it gets less in terms of how many I can put time and effort into it.

Jeffery:
You can’t do everything, right? But you want to.

Jason:
Yeah, yeah.

Jeffery:
Oh, that’s amazing. And I think there’s so many similarities between how you operate and what you do and what we do at OPN and I think that there’s, you know, there’s a ton of synergies just from how you approach business, how you look at things, our backgrounds, so I really like that. I think that there’s a lot of um synergies in gel there for sure. So, now you’ve kind of gone through this journey. You’re working with startups. You’ve built a lot of cool things in Ottawa. What’s your favorite part of this outside the grind? There’s got to be more than just the grind. I know the grind’s exciting but that can also be a lot of work. So, what’s the part that you really enjoy about investing?

Jason:
It’s the relationship and the hands-on learning because… I read books. I can’t stay focused on completing a full book most times. But when I’m inside a business and when I’m learning by being immersed into just the whole sphere of it all, I cannot help but internalize it and it become part of my scope of now net new learning by doing. That’s something I find so energizing. I look forward to getting up in the day to do the work. Sometimes I can’t sleep until I can get messages across through slack or the email saying, “I’ve discovered this”. Everything seems to find… it boils from, you know, what they call it… the ethos and opportunity starts finding. So I’m really connecting into those aspects of synchronicity. When I’m really aligned with a founder and then the relationship comes from that because they feel authentic genuine support. I’m doing it because I feel I can help you, not… and I often have to say no when I feel there’s a misalignment. I just can’t get excited or it’s not something I’ve already drawn to but when I see it, I do. And then my best story to share on this… I know you have some questions but I’ll just jump right into it. I’m currently… yeah I go into it? All right. I went to out to California for some business about growing one of my portfolio investments and it wasn’t gonna move as fast in terms of timelines as I was hoping. So, I was coming back saying, Okay, I gotta look at, you know, what I might take up. I had an open bandwidth slot of my time and energy to put in. And I met a founder who was just went out to the west coast. He was meeting with, you know, Sand Hill, a bunch of different VC’s and he was kicking the dust going, “Oh man, this is tough”. But I was just about to fall asleep in my, you know, in the middle seat with it, which I hate inside of an airplane, but this guy just… there’s something about him. Just had a quick few words and we just gravitated towards a conversation about why we’re there, what about our families, and we didn’t get into business until maybe 35 minutes afterwards. And then it was the rest of the whole flight. Didn’t get a wink, you know, on the red eye. We talked for four and a half hours straight. This is Tom Albert. He is the founder of MeasuredRisk. It’s an AI tech company that is providing risk services for large enterprises. And I’m going wow. I see alignment because first, it was about what we talked about as people, as you know, men coming back from battle so to speak. And so, we use this analogy in our own sort of working relationship is that we’re going to take that hill, we’re going to rise by, you know, lifting others, and we build teams based on core strengths and expertise. All these sort of euphemisms around a military establishment because they’re selling to the department of defense. And some of the company’s best assets of individuals are all from that background. So, we really resonated with that and I end up wrapping up my consulting practice to jump on and be uh the CEO. And we’re gonna… that’s gonna be the current priority for the near future because the goal was to raise fundraising for a seed round and we’re getting to the short end of that possibility right now so… And that’s seven months later so sometimes these journeys don’t have to take a long time. The more that you put time into executing, which is ultimately answering one of your previous questions. My favorite thing of business is execution and successful execution. Because the win feels as good as anything when I played, you know, competitive sport so I look for that too.

Jeffery:
That’s awesome. Well, congratulations.

Jason:
Thank you.

Jeffery:
It’s probably the most congratulations I’ve had in a talk. This is great. That sounds huge. You’re going to be a new CEO and that’s it. You’re moving a business. So, I love it. That’s awesome. You mentioned and I want to explore this just for a quick second. You mentioned how you do things to build trust and build relationships. CEO’s of startup companies, they are brand new usually. They have a tough time selling into companies. I probably predict 95% of all CEO’s and startup companies they’re builders not sales people and that’s what their shortcomings are. That’s where they end up going down in flames because they can’t figure out a way to sell, or they don’t even want to try. And they try to lean on other people, or they lean on other people for finance, and they don’t really understand all the business fundamentals. But one thing that they can really do better is relationships and that’s going to allow for those other pieces to work better. So, you mentioned the things that you do to get comfort level with the CEO. Is there’s something that you can share that helps startup CEO’s better understand how they can manage relationships, or at least start new relationships with investors, or with their team better so that they are more in control of their position, so that they can still grow their business without running into other problems they’ll be able to foresee them coming because they’ve built that relationship?

Jason:
So, to to summarize your question, I would say is there certain things that I do to imbue trust and with the startup founders and the ceos I’m working with. Yeah. One of the things I find that… it starts without an expectation we’re going to work together. Let’s actually spend some time having conversation. So I like to do sometimes long walks, you know, not too long but, you know, on the campus, a beautiful campus, like Carlton or have… invite them over for a roundtable of beers with some of my colleagues. So, I first invite them into some of my network and have them sit down with guys just having beers and I expanded to women founders as well. So, I work with a lot of female founders so I invite someone that comes together that might be a good suitable relationship to that individual. So, I think about where they’re going and I try and put people in front of them in a social environment first. And no expectation, but I also get the benefit what do you think of that founder about their… how they resonate with you? Is there’s ways in which how they describe their opportunity that you like? What would you like me to explore more about this opportunity? Because it’s going to move from a social back to a, you know, professional. So that’s one of the things I do. I’ve also hosted people over my, you know, for patio drinks. I have an interest previously in a restaurant and a brewery so I invite them there sometimes to get to know the founders I’ve already worked with. So, showing that there’s a cadre of other like-minded entrepreneurs that you can tap into. So, you leading your organization doesn’t have to be single-minded focus. You can call it a mastermind. So, I build informal masterminds with get-togethers once a month. Not as robust as OPN. I love to be in Toronto. I’m going to take one incoming soon. But I do it informally around either one of those establishments or somewhere that’s going to be fitting for that founder. So I roll it out first without, you know, without shiny blanket promises. Just enjoy some beers with people that might be good connections for you. That imbues a lot of trust. And then I show them my process. I have an infographic about my process and then I have some KPI or metric case studies of the works I have done. And I show them how I’ve worked with them. And that… and then the other thing is time. Open lines of communication and time. I don’t rush it. If it’s too rush and for whatever purposes there might be something there that is causing some strain or stress that just might rush the wrong way on the opportunity overall. So I let time tell. So typically, it takes me about two to three months before I might even consider jumping and onboarding to a new project.

Jeffery:
That’s awesome.

Jason:
Likability factor helps too.

Jeffery:
What’s that?

Jason:
The likability factor.

Jeffery:
Yep. Well I like that you process it through and now if I’m an entrepreneur, I think I can relate to that and I am an entrepreneur, but if I can relate to that from a different side is that, the value that comes back is that… you need to be more personable, you need to be able to open up lines of communication, and you need to do things that will help bring people together. And you’re doing all those things by putting networking, little networking events together, which makes someone feel comfortable. It’s allowing them to see that you understand where they’re coming from and where they’re going. But you’re also getting in, you’re rolling up your sleeves, you’re doing a little bit of the hand work, you’re introducing them to people, which again makes them feel comfortable that you’re guiding them. But you’re also not afraid to open up your network and share them around so that they can get more experience. And now they’re going to lean on you because they’re going to start creating opportunities with those people or with those groups. And then they’re going to come back to you to kind of help structure that. You’re going to get feedback from everybody else to see how they were dealing with and managing it. And then that’s going to build a nice little relationship with you and that person to open it up to go forward. I i love it. I think that it’s a great way to spin it back from a startup perspective on the things that they need to do in order to work with investors, or work with teammates, or even work with outside constituents, or people that have an interest in their product or in their in their structure. Is it sometimes you got to go above and beyond, you got to go for that beer, you got to try and take yourself out of your element, and you have to be open, and I… for me it’s the hardest thing in the world. I always use the analogy that there’s a hundred doors or a thousand doors in front of me and only job I have is to pick the locks and open the door. Problem is that I’ll open them but there’s a lot of people inside that room. But I don’t want to go in the room, and I don’t really want to talk to all those people because that’s not my thing. So I’ll pick the locks but I’ve got a team that I’m gonna shuffle in and I’m gonna go to the next one. And then when they start to warm up and get everybody comfortable and feeling great, I’ll jump back in and be the, I don’t know. I won’t say I’m the party favorite. I’m certainly not gonna be that. But I’ll jump back in and share stats and information to make them feel comfortable that they’re being taken care of by a great team. But the team has already delivered all of that and that’s really it. So, I’m just kind of that in and out person that supports it. But I love the fact that you’re really getting them to trust you and feel good about it and then be able to build metrics and KPI’s to help them through that. So, again from the startup perspective, I think that that’s a real win for them but they also need to learn from that because that’s going to help them build a relationship with you. Because I find that a lot of startups and CEO’s they’re standoffish at the beginning, right? They’re like, “Oh, just another person trying to take equity or another person trying to get in and take my business”, because they’re super defensive. Versus saying, “Hey, wait. Maybe there’s some value here and you’re creating that value” so…

Jason:
I have one more suggestion that probably would work with anyone. If you want to help a charity run an even–I usually run two to three events a year– and with anyone I’m, you know, building relationships with, I invite them and I tell them who might be there. And sometimes if I want to know what they’re made, of I ask them if they can do something to help. How they respond says a lot because if I’m a person that wants to build community. I start with community first, and I seed it, and I grow it. If they, and I’ll speak it verbally this is who I am, but if they don’t see the worth and nurturing of that community element that I’m putting forward by going to the front of the room and hosting, or chairing, or things of that description, then maybe it’s not the same fit. But I i think anyone can do that. When you’re at the front of the room, people can now understand who you are. You don’t use the mic to tell your whole story, no. But the fact that you do it tells your story. And that’s just part of the makeup. My mother was a community activist and during my formative year, she was making certain that Hydro Ontario was not putting massive electricity lines through the back of schools. She helped change that from being a policy now where you don’t see you know electrical lines running through the back of the school system, right? So, I felt I saw the worth our whole community rallied together and I had tight-knit relationships out of it. So, I often will leave from the front of the room, do a community event, invite those people that need to be connected, and then I’ll check in on them and and introduce and and host. So, that’s the way I do it. Not everyone is comfortable doing that way but if you do it purposefully, you can define it any way you wish.

Jeffery:
That’s awesome. You’re a community connector. You’ve got the direction and the flow so that’s amazing. We need more people like you, Jason, that are just moving people around. You go talk to that person. You over there. Yeah, I think that’s brilliant. No, that’s awesome.

Jason:
I do the business of it all like, you know, I crank out the, you know, the business and the sales and the tech. But my enjoyment level comes from bringing people together and seeing, you know, when you shake all those different sort of brilliant people together, what molecules come out of opportunity.

Jeffery:
Well, I’m sure there’s a lot of sales that come out of that because connecting and making people feel comfortable is certainly a good way of doing that. So, brilliant. I love it. I think your consulting background has really helped you thrive in this space of being able to find ways to connect. So, I love it. So, I i think what we’re going to do now is we’re going to jump into maybe one more question then we’re going to go into rapid fire questions. In all of the experience that you’ve gathered from the investments, working with startups, building an accelerator, the networking, all this great stuff, is there one or two things that you can pull from this that would say, “You know what, if you’re a startup and you’re going to get into your own company, here’s two things that I think really define and make a startup. You need to have tenacity, you need to do this”? What are those things that you think really drive that out so that an entrepreneur watching this or listening can really think in the back of their head, “You know what, I got to write this on my vision wall and I got to make sure every day I’m looking at this because that makes a big difference to how I’m going to build this”?

Jason:
Yeah. Definitely I’ve been finding through the theme through all of my engagements with startups it was team alignment–the team competency, the capability, and the vision being aligned. Everyone can be excited at the front but you then have to assess it against the other thing. What risks are we going to level up and hit because that’s when the team has to come together and go through it, over it, around it, that’s what a team that’s aligned on a vision can see problems and surmount them. So how you manage risk and how the team aligns is the two two things I find are always within the control and the dialogue of a founder and his team. You can decide what risks you want to take, you can bootstrap and not take on funding, you can go after the big industry titan, or you can go find a very nimble value-added opportunity, you can make an area of approach and make a great business out of it by managing the risk. So you have to make those questions weld, well-known, and research, and then discovered. And so those are typically what I like to drive in early on about how this team came together, why, where everyone’s alignment and commitments are, and what risk do you see, do you understand them, and how are you going to go over overcome them.

Jeffery:
Awesome. I like that well managing risk and in alignment, those are two big players, two big pieces. And you mentioned it earlier that the alignment comes to execution. And you love executing so if you can’t align a team to execute you’re going to be all over the place, people doing all different things, and then your risk factor is going to change because you’re going to be risking on things you shouldn’t even be talking and tackling because you didn’t align your team. So, brilliant. I love that.

Jason:
Yeah, great summary. You do a better job than I do.

Jeffery:
No, that’s good man. No, that you did it. I’m just like, just writing the story, man. Just making the story work. But I love that. All right we’re gonna do the rapid fire questions and then we’re gonna go to the crystal ball question. So for now, let’s go. So, quick rapid fire. I gotta explain rapid fire because I’ve seen other ones where you’re like grab fire people go for an hour. So, rapid fire, just whatever comes to mind. All right. And some of this you’ve already talked to but that’s okay Wow many companies do you or dollars do you invest per year?

Jason:
so I invest up to 50,000 in a year.

Jeffery:
Okay, any… Sorry… Any reinvestments that you do and percentage?

Jason:
I’ve done uh reinvestment and um that will I like to match my stake to keep my position.

Jeffery:
Perfect. Any notable companies that you would like to share in your portfolio?

Jason:
Two. Primarily at MeasuredRisk right now, which is AI technology. Also Greenery, which is brand licensing and green products for stationary space. And then Events.com, which is scaling up crazy. So that was three.

Jeffery:
All right. That’s good. Perfect. Any specific verticals that you like to focus on?

Jason:
Yes. Definitely web technologies and I also like to do entertainment and real estate. Entertainment is not so much. It’s more content and technology interfacing and… yeah.

Jeffery:
Okay. Do you have any preferred terms that you like to invest on? If it’s safe, preferred shares, common shares, that type of thing?

Jason:
Because I’m on the founder journey, I like safes as an instrument. It allows for, you know, that future equity negotiation but I am moving more towards prefs as it’s hard to get your liquidity back, right? So, you want to make certain you’re in good position for that.

Jeffery:
I like it. All right. What is your timeline for investment? You did mention that you could take two to three months.

Jason:
Yep. Usually about two to three months and… but I’m also on the journey with the founder so I find if you’re raising a friends and family around, conclude matters within six months. If it’s towards a seed, it could be up to 18 months. It depends on how ready you are. And that’s helping you get there.

Jeffery:
Perfect. Do you lead rounds?

Jason:
I’m not as yet but I use due diligence checklist to make certain all is ripe and ready, yeah.

Jeffery:
Any… Do you take any board seats?

Jason:
I have, yes, and I will be with MeasuredRisk’s upcoming.

Jeffery:
Is there anything that you will heavy on when it comes to your DD?

Jason:
The technology value proposition getting validated.

Jeffery:
Okay, value validation of tech. It’s a good one. Okay. All right. So that’s pretty much it for rapid fire questions. You did very well. You went through quickly so no penalized points. You still have 10 points. Okay, so last last question is the crystal ball question. So, based on where the markets are today, where they’re going to be and all that good stuff, in your crystal ball, can you give us any predictions of maybe verticals that you see opening up in the next 12 to 36 months? Or, even on your side things that you’re looking for in the next 12 months which may change in the next 36? So kind of crystal ballish any predictions that you have that we can all live and learn from.

Jason:
Well, I feel it’s probably best insight and I’m playing in it so that says a lot. I’ve decided to leave one of my professions consulting to jump right in Artificial Intelligence technology and augmentation of the executive decision maker. It has been utilized for very specialized industries but the general purpose ability to help individuals in different verticals, healthcare, defense, logistics, etc, they need tools that providing insights and anticipatory intelligence and this is something we focus on MeasuredRisk. So, when I caught that from my consulting background, I realized I was always augmenting the executive and how they made decisions going forward. And there was always challenges or I produce, you know, some print doc and always annoying and because it never got fully implemented. AI, you can codify it, build dashboards and alerts that are very specific or very generalized, and is going to change. And there’s 2.9 trillion dollars of AI augmentation new business that Gardner is anticipating by 2030. So, if that’s not a big enough market to pursue making better decisions in business… that’s my crystal ball prediction for everyone.

Jeffery:
No, I like that. And you know what, since everybody’s going to be a little bit more distanced and separated that a lot of these types of choices and conversations need to take place in the background, and you need to get information and answers quicker, and that augmented style of management is going to come into play, and I think you’re right. There’s it’s… Well, it’s a massive market for one but two certainly adding in some AI and some machine learning is going to really help propel that decision making. And you know what, there’s a lot of decisions that are buried so that information can come up from somewhere and help, right?

Jason:
Yeah. It’s… We have a lot of biases already how we filter out information because we’re always bombarded by information. But you need something to be able to alert you to something you just wouldn’t otherwise see. And that’s ultimately… isn’t that what an entrepreneur is about? Is seeing something that others don’t see and pursuing it rightly and opportunistically. That’s why it really resonated with me to step in in such a large role and look forward to updating you and the audience, the future how that goes.

Jeffery:
Yeah, no, I’m excited looking forward to it. So well, I think there you have it. We’ve got a good prediction. We’ve got a lot of insights. You shared a lot of great information and as I always do, I took lots of notes. And we’re gonna rip through all this and put together a nice little story line and some follow-up material for it in the show notes. But I do, Jason, want to thank you very much for joining me today. It was a great conversation. I think we’re probably going to talk for at least another 10 hours on all of this because there’s just so much content and material when it comes to helping and working with startups. And at that, I want to give you the last word so the last thing that you want to share to startups, or to investors, anything that you want to say that would really help trigger them, or excite them because you do like to share that energy. But I give you the last word. You can say anything you like.

Jason:
Life is a journey. Entrepreneurship is a journey. It’s all your ups and downs that make it worthwhile. So, choose your moments. Live it well. Hope to meet you sometime in the future.

Jeffery:
That’s brilliant. I was going to write that down but it was so fast. I was like, you know what I’m going to have to go back and listen to that but that was a great line. So, I love it.

Jason:
You’re a great interviewer. It’s a pleasure. Thank you–you, your team and your organization. Look forward to interacting more often.

Jeffery:
You bet. Well we’ll chat a little bit later. I’ll send you a text or we’ll chat. But outside that, Jason, thank you very much. That was phenomenal.

Jason:
Yeah, fantastic. Have a great day to everyone else too. Cheers.

Jeffery:
Thanks, Jason. Well, there you have it. That was Jason Daley from from Ottawa. I love Ottawa. Such a nice nice nice city. So many things to do. Wilderness is brilliant and amazing. But Jason followed up with so many cool things so we really got to explore the whole side of mentorship. I know we’ve talked about mentorship before but not at the same capacity of this, as this. We really dived into how this mentoring really does help an entrepreneur move forward. And he built a whole ecosystem in Ottawa with the university just to talk about mentorship. And phenomenal information. He really dove into that. And one of the things I really want to pull out of this was that it’s all about relationships. How you build them. And then the second thing was execution. He talked about that all the time. How are you going to execute to be awesome? And I think that he really knocked a lot of those things home. His two main things that he talked about from a CEO perspective or from a business is managing risk and alignment, team alignment. And that’s big because we didn’t really get into that in a lot of other discussions. But I really do like that he emphasized on team and how team aligns on the same execution and the same plan. So, lots of great information. Jason was great. I look forward to our next talk have an awesome day. And thank you for tuning in. And you know as you mentioned, life is a journey. And he went on with all this entrepreneurship’s a journey. You know what, you gotta live, you gotta learn, take the risk, and go for success. I’m paraphrasing. Thanks, Jason. Have a great day.

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