Jeffery:
Welcome. We’re super excited to have you join our asking angel. We might have to change that name because we’ve been interviewing angels and VCs all over the world, but we just call everybody angels. So maybe we’ll just be sticking with that and we won’t tell what an angel is, we’ll just say that all good people, um, but yeah. Welcome. And the best way to start is if you can share a little bit about your background, kind of your journey, what you’ve been up to, and where you are today…
Dony:
For sure.
Jeffery:
And then the only other ask is if you can share one thing about you that nobody would know.
Dony:
All right, let’s go. Um, I come from I’m from I’m from just outside Toronto. Canadian, Um, Just grew up in Ancaster, just inside of Hamilton, sort of in the early stages of, you know, going twenties and thirties. Serial entrepreneur, a bunch of different verticals, everything from hospitality to, some land development projects to, uh, my dad was a huge environmental scientists and, you know, helping out on some cleantech initiatives, and really in love with entrepreneurship. I applied for a renewable energy permit here in Ontario on a what I thought was going to be a land development project and was awarded one of the Green Energy Act renewable energy permits. I was very surprised. I would love to say it was, you know, a whole bunch of planning and intelligence that led to that. But it was, you know, a significant component was locked, and so I had to learn a lot about renewable energy and ended up developing one of the largest solar farms in Canada. I monetize that project or the development work to a Panasonic anchored private equity firm called Corona Group. They were about a three quarter of a billion dollar fund. and I was sort of, you know, um, my first real exit if you want to call it that of significance. And it was pretty transformative from a personal like financial perspective. Gave me a bit of breathing room to sort of step back and think about what I wanted to do next. And so I actually went back to school, and I did my masters degree in entrepreneurship. The sort of process of exiting on that solar farm made me very aware of a lot of the gaps I had in my skill set.
And I ended up being on the project, kind of the de facto finance guy. And I use that term really, really sort of, you know, that these are intentionally, you know, quotation marks around it. I had no clue what I was doing. It was baptism by fire. You know, I stepped into my first meeting or one of my first meetings to finance the project, and they were discussing, you know, some guy was discussing with me the terms of debt surrounding the project he was talking about live or And I literally thought LIBOR was a guy. So I went home and was like Googling who is this LIBOR? And it was like, okay, that’s the London interbank exchange rate. Okay? And I don’t know, I don’t know, you know, it was very humbling the process. So anyways, I went back to school and I thought it was a great chance to fill in some gaps.
And so I focused on venture finance within a masters degree in entrepreneurship. Uh, And so coming out the other side of that, the gentleman who was running, uh, managing partner at Coronal, who bought my solar farm. He did really well at Coronal and sort of transitioned off and had been investing on his own as an angel. And thought it was time decided to take it to the next level and start his own fund.
And when he was looking back along his journey, um, he was sort of looking for people who he got along well with and respected and amazingly, asked me to come join him. And that was sort of the genesis of my joining Checkmate Capital. And so for the past two years, I I moved from entrepreneurship to the dark side of Venture Finance, and I’ve been working with checkmate capital as a partner, put my own money in, and off we go. And, uh, so, you know, we’re sort of somewhere between a family office and a venture capital fund.
We do take investment, but we also are definitely unlike a venture capital fund. We use mostly our own money. We have a few different verticals that we invest in. I guess we’re just a group of guys that got together and really love supporting entrepreneurs. And so if you can convince the guys something’s good, we’ll invest in it. But that seems to fall along our personal interests.
And so everyone on the team is interested in, You know, I think we all have big hearts, so we tend to invest in things that help people like health and healthcare and healthtech, biocide drugs that have the potential to change people’s lives in a positive way. We also have sort of this renewed sustainability lens where we like agtech, we like, waste to energy, waste to resource, we tend to take a view that things that are being thrown away are cheap to get. And if you can turn them to something of high value, then that’s a great business model. Uh, and that sort of seems to be the lens personal lens. And I guess checkmate funds around are sort of investment thesis. And I’ve been rambling, um, the That’s sort of my background. And what got me to where I am today and something that nobody like nobody knows about me, including, like, my loved ones?
Jeffery:
Well, you can choose. It’s more of a…
Dony:
I mean, okay, like from the perspective, whatever you want?
Jeffery:
It could be anything out there.

Dony:
I’m an award winning filmmaker. It’s sort of a passion, in that time after I sold the solar farm, I have a love for visual storytelling.
And, um, I made, you know, three award winning documentaries, uh, around themes that resonate with me. One with a documentary about mangrove forests, which is a really important ecosystem people don’t know about. And a couple about animal assisted therapy where they’re using animals to help people facing profound physical and psychological challenges. Uh, but interestingly enough, that skill set has actually been preposterously important in business because ultimately the structure of telling a great story and the tools associated with crafting a compelling narrative apply all through business every time you’re pitching, Every time you’re trying to, you know, talk to an investor or market your product. Ultimately it boils down to the same principles of storytelling, and so it’s been a very transferable skill set. If you want to call it that.
Jeffery:
That would be huge. Just being able to take something and build a narrative around it and then going out into the world and everybody’s coming to you with the narrative of something that they’re trying to sell and you’re looking at it going (sound) (inaudible) got a little bit…
Dony:
And the myth is that the myth is that it’s an art that only creatives have access to, and the truth is that it’s highly technical. There are standard structures and approaches that you can learn and you can develop and you can cultivate. You get better at you know, you don’t have to just say you’re born a storyteller. Some people have an aptitude for, like everything, but the skill sets associated with being a great storyteller are absolutely learn-able. So that’s something that I continue to try and cultivate as far as the craft, and it’s something that continues to benefit me even if I’m not making films,
Jeffery:
No, that’s awesome. Yeah, I feel the same way. It’s, uh, for me it’s It’s really all about telling a great story to get people interested, understanding what you’re trying to do. And that’s kind of how we help, right? We’re that in between, accelerators, incubators and funding. And we really try to get you to understand what you’re selling because a lot of time people just don’t understand it. They think it’s just selling a widget. This is what I do. But there’s a lot more to it. And then tying that story into all the other aspects of your business makes a big difference in having that creative mind. It’s not about coming up with the most clever ad. That’s not what a creative mind does. It’s coming up with, like you said, that technical aspect and being able to really hone in on the real problem and the real focus and pull that out.
Dony:
Mapping out your customer journey and understanding which hurdles are trying to overcome with your marketing materials and then using those highly technical things — to them, yeah, sure have some fun. Come up with something clever, but the process of getting there, you know, 90% of it is non creative, 90% of it is just super technical on that, you know, I I think it’s a lot of people who are skilled at it. They hide that they don’t want you to know that 90% of what they do and so valuable can be learned. But you know, it can be.
Jeffery:
Well, eventually. I think it becomes almost like a I guess, in a way it’s processable — like it’s kind of like a 10 step thing you’re going to go through each time. And if you can get yourself into that mindset, sure you can do that.
It’s like a golf swing. If I stand there and going to hit the ball, and I go through the tilt my head, put my shoulder back, push my butt out, Then I got to do this and then I’m gonna shoot sure every time you can do that, but that doesn’t mean you’re going outside the box.
You’re not thinking things. That comes from time experience and being through the crux of life, so that’s pretty amazing. Uh, and I love the idea on on that you’ve had three. I’m actually I want to watch these. I’m going to go through them. The mangrove one. I believe I actually have seen it. And I’m gonna double check when I go into it. Is it online?
Dony:
Yeah. Yeah, they’re online. I’ll send them to you.
Jeffery:
Yeah, I think I may have seen the one, because sounds very familiar. It’s only because I watched so much stuff. It’s not funny, but a good content. So I may have checked that one out already. But either way, I’m excited to see them. I feel like I wrote a screenplay five years ago, four or five years ago with a writer, and she was phenomenal. And, uh, if you’re ever looking for a great writer, actually I can introduce you to her. But we wrote one and we picked it around for a while, and then different versions of it started coming out. But it’s still out there still pretty cool, like eventually one day I’ll put some time back into it, but we enjoyed ourselves whipping through that. It was very, I guess when you’re learning something you’ve never done before when it comes to It was a lot of fun you can imagine
Dony:
For sure, for sure.
Jeffery:
So just to take a step back to and I really love the fact… when you sold your company.
One thing that always comes about and people always ask, like, what did you go through? How did you figure this out? How did you know when it was time to sell those things that really drove you to doing this? And why? What made you actually decide that it was time to move forward. And like you said, enjoy what you had built the outcome of it. What got you to do that?
Dony:
Perfect. Teetering on bankruptcy.
Jeffery:
I’m sure that’s not being much (Inaudible)
Dony:
So much stress. Way too much debt, personal debt and personal guarantees. And I was done with it.

Jeffery:
Oh, really?
Dony:
I went through the textbook definition of the founder’s dilemma. I don’t know if you’re familiar with it. No last sermon from Harvard University essentially studied entrepreneurship, and he realized that the data shows that, um, a couple things data shows a couple things.
One, uh, upon first receipt of external capital, like 66% of founders will no longer be control of the company within three years. Two, If you look at companies as a firm, as an enterprise, and you look at their and you look at their sort of valuation enterprise value, companies where the founder is still in control of the company, generally speaking, are worth less within five years. As opposed to and so, you know, um, I received a solar farm contract for, you know, a three megawatt solar farm that, you know, layman’s terms approximately $3 million a year for 20 years, $60 million. I wanted every cent of it, and I wanted to be in control. So I tried to finagle my way through this project to maintain as much control as possible. So I gave up no equity. And, you know, one or two partners, etcetera, etcetera, etcetera. And you know, all of the assumptions I made about being able to drive this forward were incorrect. You know, the permitting took longer than I thought it was. The costs were more expensive than I thought they would be. The curve balls that got thrown at me in terms of litigation and whatnot. It got really, really, really challenging. And so the dream of retained ownership fell apart. But then, you know, I switched gears and decided. Okay, fine. The best way to monetize all this work is to sell it. And it turned out being really great.
It turned to be amazing. But I can say that, like, more challenging than the financial pivot, if you want to call it pivot, Um was the fact that the personal sense of failure that I had represented to so many people that this was my project, I was going to take it all the way and own this thing for 20 years.
And I was going to be the first non institutional solar farm owner like everyone else. I was doing this with big companies, and I was a guy, and it’s like, Wow, you know, like, I’m gonna do this. And I told so many people I had the perfect plan. And so to then go back to those same people and say, Hey, you know, it didn’t work out. That personal sense of failure was more profound. And and and that was the more bitter pill to swallow than just the financial strategy pivot. But I did, and I had to and and, um, you know the process and everything. Now, in retrospect, I’m so thankful for. I gained more, have learned more, then I ever would have just if everything went perfectly and smooth. You know, I think I’m a better person for the for the way it transpired. But I would love to say I was the architect of some, you know, phenomenally well crafted exit strategy. No. I had tried so many times to become the king and realized that, um I didn’t I couldn’t be the king, but I could I could make some money and let someone else, you know, own the project. And so that that was sort of the the path tumultuous path to to exit.
Jeffery:
Which isn’t a bad thing. So the thing is that you realized it, whereas a lot of people may have taken more debt on and more problems and the food or whatever and not been able to produce the outcome. What was that moment?
Dony:
You last (inaudble) All that had gold fever during the gold rush until you’re in it and then, uh,
Jeffery:
This is why my uncle didn’t come here. This is crazy. Yeah. So what was the part that made you change, though? Did you wake up one morning? Just say I’m tired. I don’t wanna do this. Or was it like, staged events that occurred? And you’re like, I can’t do this And I got to do this.
Dony:
It’s the culmination of multiple things stacking on top of each other. And, you know, you wake up every day and you’re excited to work on something. It’s your dream project. And then at a certain point, you go. Wow, I’m not happy like this isn’t a dream anymore. This is This is just This is actually a source of unhappiness as opposed to happiness. At that point, it’s like, Why are you doing this every day?
Why am I getting up fighting over this thing every day? It’s not even making me happy anymore. So, you know, I think one of the other cool things that came out of it is that that I negotiated a pretty interesting agreement so that there’s some retained performance benefits. I kind of stay involved with the project for the rest of its life and even though it’s not in any capacity an owner. But I can still go up there and look at it and, you know, 100 acres covered in solar panels. I helped make it, and I’m proud.
Jeffery:
It’s amazing!
Dony:
I’m proud of what I achieved so…
Jeffery:
Well, you know something that’s huge, what everybody would want to accomplish.
You were able to do that. I mean, just building a company, building a big contract and selling it. But you came up with all of that. Regardless of the pitfalls and the roller coaster ride that you went on, you still were able to make that determination move forward.
Dony:
I would argue that almost any business person, um, probably probably sugarcoats a lot of the elements of challenge and and often either intentionally So either consciously or subconsciously, um, um discredits the amount of luck that’s involved in any successful venture.
A lot of things have to align for something to be successful beyond just a good idea and and, you know, to the credit, so many entrepreneurs out there who have great ideas. It’s not always that you didn’t have a good idea that something didn’t pan out. There’s also a lot of luck that has to align.
You know, I define luck is when skill meets opportunity. So as long as you’re continuing to work on your skills and being open the opportunity, absolutely you will be quote unquote luckier and luckier person. But it’s ultimately variables that are external to your control that have a lot to do with, um, the success of a venture. And, you know, one of the one of you know in the business world, there was sort of a switch from the SWAT analysis of companies, strengths, weaknesses, opportunities and threats to something called Porter’s Five Forces, which is the preferred framework now. And Porter’s Five Forces sort of the acknowledgement of the fact that when you look at strength, weaknesses, opportunities and threats, you’re really inward looking. Porter’s five forces is like outward looking, and it’s actually saying external factors have more at play on your venture than internal factors.

Jeffery:
And that can come down to covid like things that you don’t expect it happened. One minute you’ve got a roller coaster ride in the next minute
Dony:
You’re going to plan for it. You could have planned for it. I have so many friends. I I my, my first ventures are in hospitality on a bar and a nightclub in the city of Toronto. They’re very successful. And through that huge network in the city of hospitality, you know, hospitality players, they’re just rock.
And and, you know, some of these guys were like, you know, they felt like they had ATMs. Like they just they could just open another bar with their name and they would just print the money. And they’re just, like, how can I find another location to rent? That was the biggest challenge. And all of them are just like, like, you know what happened there.
Still in shell shocked and then tangential, you know, like, to that industry. You know, people in, you know, um, events or people in applied technology and equipment for events. They’re all rocked right now. There’s no possible way they could have, you know, anticipated what what’s happening is,
Jeffery:
Or even how to embrace it if it ever did happen? And how they would pivot through that right? It’s It’s not one of your main main thing of focus. You’re just focused on your business for now. And now I think you’re gonna There’s gonna be a lot of measures built into how people run their companies or how they rent out their apartments or how they do everything.
There’s always gonna be this backwards back and your head thinking, Wait, can you do this? Is this there? Is this there? Because if we ever get hit with this again, I need to protect myself. So there’s gonna be businesses that were blue chip or just steady growth, things that are now going to be taking a beating and be classified as high risk because you don’t know what that possibility is with that right? Like commercial real estate. I’m here right now. They’re rocked and everybody’s like they’re probably pumping stories, though, like crazy saying, “Oh, no, everybody’s coming back in the city” and then you’ve got the real data coming back. You know, the city of Toronto lost 50,000 people in the last 12 months, starting from July 2019 to July 2020 and that’s the most ever, and that’s pretty big. So now you’re gonna say, well, that just seems like a minor. 2% will now put covid in there. Now you’re going to have a bigger change. You’re not gonna get taxes. So there’s cascades everywhere, right? And it’s got to be re planning and thinking about these things. Now when you build a company. So you made this pivot, You sold the company. How much of this… And you mentioned a little bit about this. But how much of this is listening and interacting with your environment to come up with this choice that you made? You mentioned it’s luck. Well, a lot of luck is just sometimes listening to what’s going on. A lot of times you want to be pushing it out. You’re like, I don’t have time to this. Don’t want to listen. But that moment someone shared some real valuable insight that you could have thought about.
But you’re not really thinking of luck or thinking of opportunity. How much of that came into play when you were doing this?
Dony:
Exactly like you said. Um, you’re working. If you want to be luckier, You better open yourself up to more opportunities. And I think the losing the tunnel vision opens the opportunity. Well, then I was able to act When? When? Something that I wouldn’t have seen before presented itself. And so, you know, um, yeah, I would say If you want to increase your likelihood of luck, then you know what I learned was to just keep it.
Keep a wide, wide lens on the opportunities that are around you at any given time.
Jeffery:
And did that help you change and sell? Like because you now have more opportunities? You knew more people when you went in to sell. You knew who to go to right away. Or did you kind of have to vet it out?
Dony:
Trial and error man, you have to figure it out. I never sold a multimillion dollar solar farm before, you have to fake it till you make it.
So the first three meetings, you go in and and, um and you’re meeting these. You know, savvy sharp M&A focused renewable energy funds. And what do you do? Like, you know, you listen to what they have to say. You try to understand what they’re talking about and you learn, every second you learn and by the fourth one, you know what you’re doing.
And you’re not surprised when they tried to, you know, put some like Einstein’s equation on the board to explain, to wear solar farms, not worth anything. And you can just laugh and say, well, you know, I like Einstein’s equation that you’re trying to, you know, fool me with.
But you know, the guy before you offered me 10. So you know what you got to know? No matter what your equation gotta be 10 and you just you you learn how to handle yourself, and and I really feel like, you know, um, it’s one of those things that, um you know, while I’m very, very happy with and and extremely cognizant of the of the skills gained through my education, it is one of those things that you really learn best by just doing. Accepting the fact that you’re not going to be perfect the first time. Uh, you know, one of my favorite anecdotes is that there’s a famous comedian named Charlie Murphy. Um, he was on the Dave Chappelle Show. Eddie Murphy’s brother be really quick. Yeah, he bombs, he bombs on stage the bombs and it comes back. And he says to his brother, Eddie, he goes, You know, Eddie, I bombed to downstage. I’m really bombed, and I need to be cheered up.
Eddie looks at him and says, You know, f you. Who do you think you are? He’s like me. Chris Rock, Richard Pryor, Jerry Seinfeld. Every single one of us have bombed. What makes you think you’re better than us for the best five comedians on the planet and we’ve bombed? Why do you think you’re not gonna bomb? And it was just like, you know that that really story really stuck with me because it’s so applicable. I was just reading today that that on the success of Airbnb’s IPO their their seed round was turned down.
They got turned out by 75 investors before their first investment and that’s Airbnb. And it’s like those guys got slapped in the face 75 times. You know what makes what makes you think that the first time you go with your your fun to go raise some capital from LPs? They’re going to say yes. What makes you think the first time you’re an entrepreneur? You know, it’s your first shot at it. And so for me in this project, it was like, you know, I knew that I had never done this before, so it’s just like all right, I’m gonna suck the first three times I do it, but, you know.
Jeffery:
But you’re not closing on the 1st meeting, so you’re going to learn as much as you anyways.
Dony:
You have to accept it, accept the fact that, you know, until you do something, you’re not going to be good at it. And, you know, like there’s some statistics out there. You spend 10,000 aggregate hours or something, and you eventually become good at it.
So just get on that path to spending 10,000 hours doing something, and if that’s being an entrepreneur, then be an entrepreneur for 10,000 hours. Then you get good at it. Yeah, you just got to stay in the game.
Jeffery:
Yeah. Malcolm Gladwell has pushed that. Well, I’m a big fan, and I do agree. You gotta put time and you gotta focus. You gotta be hyper driven, but you gotta be open in mind.
You got to listen and take all the insights from everybody and then decide for that down into the right story or the right narrative that you need in order to grow and build. And then when it comes to the crunch time, ask questions and ask lots of them because it’s pretty crucial because that equation can screw a lot of people.
Dony:
Yeah, I agree.
Jeffery:
Honestly, amazing experience. Having any sort of M&A experience is going to be doing anybody well, when it comes to investing and working with entrepreneurs.
You mentioned that you went back to school, and it wasn’t in Paris. Was it online?
Dony:
How did that work? Yeah, absolutely. It was the first. So HEC Paris, people don’t know much about North America, but, you know, I want to call it the Harvard of Europe
Jeffery:
Massive School. Yeah, I wanted to go there..
Dony:
why it’s more presidents in France than any other school. Uh, consistently ranked number one business school in Europe, Consistent rank talk during the world. Really, really an amazing, you know, school elite, elite school. And they offered their first online master’s degree, executive master’s degree and entrepreneurship. I was one of one of the 1st attendees. It was a phenomenally transformative experience.
I think one of the myth of entrepreneurship is this, Like this guy who goes and build something in the garage, He he says, You know, he drops out of college because college teaches you to become a robot and they’re bad and you go and you be an entrepreneur in the face of school and the truth is that, much likeSilicon Valley in its approaches has disrupted quote unquote entrepreneurship, the top academies in top schools in the world and now even down to all schools in the world, I would say, um, they have sort of assembled and consolidated all of the most powerful contemporary frameworks associated with trying to get a really customer centric product out into market, how to actually apply tools and methods that increase the likelihood of success of entrepreneurship. And so for me, I kind of went in there cocky. And I just want to learn the venture finance side and then was completely reshaped as an entrepreneur by, you know, customer centric city.
You know, um, instead of trying to just come up with great solutions, which is sort of my entrepreneurial approaches like, Yeah, I come up with great ideas like, sort of kind of reshape my thought process into being like, really listen and look at what problems people have. There’s ways you can help to create value for people with big problems. And it’s a different mindset. From the perspective of entrepreneurship and as an investor now, you know, um, it’s something because we’re really concerned with making money. We’re really concerned with the problem that you’re solving not so much how good your solution is. If it’s if it’s a great solution to, um, you know, a problem not only have one or two people have or they don’t even have.
It’s just a really cool solution. My dad’s a scientist. You have this all the time. Incredible technological solutions to problems nobody had, um
Jeffery:
or didn’t happen yet.
Dony:
Or only if you are living in a, you know, zero g and an environment filled with, you know, some type of weird gas that it would be a really applicable solution. But, you know, like for Earth, for Earth, Where? Where? You know, Right now, and you know, I think it really gave me a healthier lens and that, um it took the ego equation out of entrepreneurship as well.
Like stop trying to think of this as some way to validate how smart or how good you are as a person and try to think of the entrepreneurial journey as something that helps other people solve a problem.
Jeffery:
I like it. No, that’s very cool. Haven’t been a big fan of that school and followed it, and it’s somewhere in the line of the next 10-20 years for myself. But I will do that. I want my PhD, so I got to take some time to figure it all out.
Dony:
It’s really cool. I gotta ask now to come back. I actually helped teach the MBAs now. On the topic of the founder, the same story to share with you. I now shared the MBA class there, about going through the founder’s dilemma. And some other aspects of the thing, but yeah, and in association with the creative destruction lab in Paris. I’m teaching the MBA. Helping teach one lecture at the MBA class.
Jeffery:
Amazing.
Dony:
It’s pretty cool. It’s pretty cool to come full circle from student to helping me with the on the other side of it.
Jeffery:
Totally agree. Well, that’s wicked. So now take all of this stuff that you’ve done, and it folds into what you’re doing today at checkmate. Maybe give us a bit of an idea. You talk a little bit earlier about the types of verticals you invest in.
What things do you look for when you’re working with entrepreneurs? What is it that you hone in on? And how is the business kind of shaped around your past experiences to get you guys where you are today.
Dony:
For sure. So okay, so we’re typically seed round investors. I would say in a lot of cases, it’s different because we do invest in tech. But we also invest in biocide and life Sciences. So there’s a bit of a different let’s say, um, there’s a bit of a different journey in that you know, in tech, what you’re really looking for is, you know, people who have developed a prototype or something and they started to find their product market fit and and now they need money to sort of, you know, accelerate the process of taking their product to market.
In biocide, people have found some type of a molecule or a drug, and there’s still six years away from being able to sell it. So it’s not. It’s not a lot of the language you hear associated with sort of investor and entrepreneurial investment is not applicable because you’re not looking for someone with products who has achieved product market fit.
But, um, that said in both cases were typically sort of the first institutional capital that an investor gets so well will lead a seed round. Um or, uh, sometimes series A but typically a seed round, real seed round, where you know, they’ve done their friends and family. They built something. They’ve got something here that now looks like there’s a way to take it to market and or in the case of drugs, there’s a clear regulatory pathway to receiving, you know, approval for this thing to be used.
And so they’re looking for investors, and, you know, we’ll come in and give them that sort of, you know, mid six figure check that they use in association with sort of the deal. We structure with them to go out and also bring in, you know, some other angels and high net worth individuals.
And to finish the round and, you know, we’d be seen as the lead. Uh huh. Part of the reason why you know, our thesis is that, um we get very we stay very involved with our embassies story about the companies we invest in. And, um um, we see that as our way of de risking the investment. So our ability to help and to leverage all of our entrepreneurial experience and financing prowess. And, you know, our global network of potential licenses and, you know, customers. If we can bring all that to the table beyond just a dollar, then then wow, that’s a lot of help that should help this company succeed. And so, therefore, be a less risky investment.
Jeffery:
I love it, and it does help when you have a lot more hands, make less work, as the old saying goes. But if you’re able to help guide but also bring a lot more to the table, it brings a lot more value for your end goal, which is helping that company get the next stage.
Dony:
It kind of answers the second part of your question, which is what do you look for in companies. And so then the human factor becomes super important for us because if we’re going to help out, we’re going to be involved.
You know, we’re investing early, so, you know, we’re seven years away from a liquidity event. Um, we’re with you, and we’re together, and we’re interacting a lot for a long time. It has to be fun. And it has to be, you know, a situation where you look forward to talking to this person and excited to help them and, you know, so mutual respect, alignment of cultures, like business culture. All of those things are are really important.
And they have, you know, they have a lot to do with the person, and not even their skills. Just like, you know, is the first 10 minutes of our conversation of our phone calls like unintentionally spent just to catch up because we’re so excited to talk to each other. Or is it, like, you know, an awkward silence and, like, you know, reading the notes. And if you’re going to get involved with the company for seven years and you’re a small team that spends a lot of time together, it’s got to be a human connection.
Jeffery:
That’s a good point. Uh, that’s that’s built over time, right? That’s focused on helping each other and being, uh, for (inaudibleO
Dony:
For us, it often starts right at the at the vetting stage where you know we’ll go and we’ll typically. And when we begin diligence on a company, you know, we’ll ask them to go get some stuff for us, you know, like we want.
We want that and and, um and do they deliver? Are they, like Do does? Does the founder actually come through and give you more than what they said they were going to On certain things? We have a We have a Canadian company we invested in, like, shamelessly plug them because we love them. But, this 1st, 1st real Canadian investment. It’s a group in Toronto called like Tyga, andwe were their first institutional investor. We, um and and they have this incredible thing where they’re taking the breast smoke that’s discarded from breast milk banks, and they’ve patented the way to isolate the most powerful antibodies. And these can be used to treat all sorts of illnesses that have really no treatment for it. Everything down to actually showing efficacy against covid, diseases of the mucosal space, uh, seem to be really amenable to these antibodies that they’re able to isolate. And it’s from a source that’s being discarded. It’s a really incredible company. And so when we first met the founder and we asked him and we said, Hey, you know, like we’re kind of worried about the supply, you know, like, will these breast milk banks go and be able to?
Can you talk to one of them and just have them document the fact they’ll supply? He got it from like 20 you know. He came back to us with, like, a rolodex, and we were just like, Whoa, we didn’t even ask for that. We had a documentary with LOIs and this and that, and it was just like, Okay, we love working with this guy. This is awesome. And then, you know, on top of that, we started chatting and we got along really well.
It was like it became really comfortable to make that investment because, uh, you know, we really felt like there was something there where we earn that mutual respect, and it’s like I said, it doesn’t has to happen after the investment, the whole process of learning and earning starts before.
Jeffery:
Yep. Mutual. There’s a mutual accountability on both sides
Dony:
.Absolutely.
Jeffery:
No, I love it. And that’s some great advice. Um, right now, what we’re gonna do just because we’ve gone through this great journey and I loved it. It was awesome to learn a lot more about what you’ve done and how you’ve got to hear. We’ve got some rapid fire questions. It’s been, too. If that works for you.
Dony:
Let’s do it.
Jeffery:
Alright right. Okay, So the first one isn’t as rapid fire only because it’s kind of ties to what you do. But so what got you interested in investing in early stage companies?
Dony:
I’m not interested in one thing. I have a really, really diverse set of interests. So investing allows me to dabble in so many different things. I can have a conversation in the morning about the efficacy of the treatment of a drug against cancer. And in the afternoon, I can be talking about soil and compost. And then in the evening, before I go to bed, I’m talking with an edge computing company, and to me, that is like, you know, that’s like the juice of life is getting. And entrepreneurs are so smart and they have dedicated their lives to these things. And you just get to, like, feed off that energy.
and so I feel so privileged and lucky. And the reason why I’m so attracted to it is like that ability to interface with the smartest people and so many different, um, capacities.
Jeffery:
I’m gonna take that recording and put it beside my name went on LinkedIn. So when they push play, it will just say that. Because I totally agree with that. Because that’s exactly how I look at the generalists. Wake up.
Dony:
I got excited even talking about it. Yeah, like, pumped up
Jeffery:
Very good. I almost swore there. It was very exciting. I like it. That was good. Okay, so what’s your favorite part of investing?
Dony:
Favorite part of investing, I would say probably origination. Origination is awesome. So origination is the finding of opportunities. And so I attend all of, like, the startup events and pitching contest and investor contest and you know getting to see and hear all these incredible ideas. Um, you know, 1% of them are appropriate for checkmate. But it doesn’t mean I don’t get to hear, like, 80 incredible ones like they’re just not right for checkmate.
But, oh, wow, it’s It’s It’s It’s remarkable. Um, just got back from something, or I can go back. I was here and watching, I think called the Needham Growth Conference investors only. But, you know, top 100 fastest growing companies in the world or us at least, and just listening to what they’re doing and the different exciting things they’re working on. And I feel so privileged again, just such a privilege to be able to be part of that. And so, you know, origination
Jeffery:
Awesome. Love it. How many companies do you invest in per year?
Dony:
We’re doing everything right. Let’s say maybe 10.
Jeffery:
Okay. Any Well, you mentioned verticals where you can share it again. The verticals you focus on.
Dony:
Yeah, health and biosci, ag tech, waste to resource would be probably our main — where right now, our entire team actually comes from renewable energy.
And so we have, like, you know, energy and energy lens as well. We’ve done some energy investment. And right Now we’re starting a new vertical that we’re all really interested in that smart cities.
Jeffery:
Okay, awesome. Uh, do you have any due diligence requirements that you look for before I make it a commitment?
Dony:
Too many. We have a huge check closely send out. You know, I think our team probably from the from the from the starting point. In bio side, we have we have a pretty we have a pretty specific lens around I p we we want good defendable. I p um you know, I think we’re probably less worried about you know, these massive addressable markets were willing to operate in a more niche space. If there’s a clear trajectory to an industrial purchaser and exit, that’s that’s, you know, reasonable.
Um, we don’t have external capital, So we have a longer picture as well as much like, you know, not yet at least. Maybe we’ll have a formal fund in the future, But for now, you know you don’t you don’t need to be. You don’t need to be out in four years.
Jeffery:
Okay. Timelines for investment. Like start a conversation to the end.
Dony:
Wow. I want to say three months, but it typically takes five.
Jeffery:
That you mentioned that you guys lead rounds, which is cool. Anything material wise, like outside of material, the things that you really focus on when you’re making an investment. The founder of the team you mentioned IP,But is there something else that really is the nuts and bolts to the investment?
Dony:
Yeah. For us, we want some aspect of our network or our skill set to provide an unfair advantage to the founder. So, for instance, you know, a lot of our team comes from Panasonic and has big routes into that. That industry is there some way. We really help you like Oh, man, if we just landed this company as a client and and this company, this would really fly.
And it’s like, Oh, we happen to know that those guys great, it’s perfect. Let’s like, Let’s throw you some money. And then once you’re ready, we’ll just we’ll just walk you over to, you know, Frank. That’s the kind of circumstance we love. You know, um, some way in which checkmate or our network and affiliates just just gives this company the edge. Uh, and I think I think you know, that’s sad for for founders, because there’s no way for you to know that, other than maybe researching us.
But, you know, um, we love that synergy component.
Jeffery:
Okay, love it. Any, uh, any preferred terms that you like to invest on, Like perhaps shares common shares?
Dony:
We typically are convertible note, Three of our team are like hardcore ex milbank. I’m in a lawyer’s, so, you know, they have a sophistication with the documentation process that I get to sit back and let them work their magic, they can be pretty pretty pretty.
Uh, they can be pretty sophisticated with the stock, but to be honest, convertible note is typically the form of investment we take.
Jeffery:
Okay. You do follow up investments or take seats
Dony:
We’ve done follow up. Follow on all the way up to pipe. We’ve gone. We’ve gone the full way series. You know, seed to series X and then and then you know, pipe
Jeffery:
Perfect. Do you lead rounds?
Dony:
Yes.
Jeffery:
Sorry. Sorry. Wrong question. Looking the wrong one here, do you take board seats?
Dony:
Uh, yeah. It’s, uh, almost non negotiable.
Jeffery:
Okay
Dony:
if we’re not the lead or we’re not, we’re not thing. But again, because of the synergistic relationship with our investments, or we’re a lot more than just a cash investor.
It’s typically welcomed.
Jeffery:
Okay. No, it makes sense. Yeah, and totally needed when you guys are trying to be close to business to help them out.
Okay, so we’re gonna jump into probably one last question. Then we’re going to some quick personal questions. So the last question is, uh, there’s always a heartfelt story where you had an entrepreneur where she or he basically came from almost losing it all to just covid hit, and they just took off like a rocket ship. Do you have any kind of stories? If you can name names if you want, it’s totally up to you. But just something that really blew your mind, Um of. And it could be a hard story that people just won’t be able to understand. But it could be anything. It’s just something that comes to mind around what it takes to be an entrepreneur and and how tough it is or how great it can be if you overcome the toughness,
Dony:
How great it can be. It’s always hard. I think I think the one little mantra I’m sticking to right now these days, as I stall to answer the question is like, you can be overweight or you can exercise. Both are hard. Choose your hard. You know, you can have a failed marriage, or you can be alone. Um, both are really hard. Choose your hard. I mean, sorry. You can have a successful marriage, or you can have a failed marriage.
Both are hard. Choose your heart. Um, you know, you can you can You can You can, um you can be an entrepreneur or you can go to work. Uh, built, I don’t know. In office. Both are hard. Choose your hard. You know, it’s choice and people who people who choose to go on the entrepreneurial journey.
Um, they’re making a choice, and it’s hard. Uh, but But if you’re the kind of person who wants to be an entrepreneur, typically it’s really hard not to be. So you pick your hard both. Both are going to be hard. And we’ve had founders. I’m not gonna go into specifics of which company, but, you know, we’ve had founders lose loved ones.
Um, you know, lose their spouse and and and have to continue on. And then, you know, the entrepreneurial journey is providing them that, you know, sense of meaning and fulfillment that, you know, before, you know, maybe only that person provided and you know, that that’s been beautiful to see. Um, and at the same time, you know, um, I’ve seen the dedication to or the need for entrepreneurship too. You know, we really, really have a bad impact. And people stay with an entrepreneur journey when you know, maybe not the right decision to make.
And so, um, it’s it’s, um I I wish some of the mythology of entrepreneurship was removed because it’s challenging, and it’s hard, and it’s just a choice. And there’s lots of great choices you can make. You know, often I don’t wanna take up too much time, but even with funding like I’m an investor, um, venture capital investor, very specific type of investment.
And often entrepreneurs confused investment with validation of an idea. Because we’re like seed and early stage investors that first time you land an angel. Wow means I’ve done. I have a great product. The only thing that makes the product grade is the market. If they choose to buy it, that’s the only real validation of your product from a commercial perspective. And so the trap entrepreneurs fall into where they care more about getting venture capital investment than they do about launching a successful product for so many entrepreneurs, I see they come and tap me on the shoulder and ask about funding and, like you’re not even right for venture capital. You know, like this is a lifestyle business.
And then there’s some, like judgment associated with that lifestyle. Businesses are the best if you can find them, don’t have a VC sitting on your head. You know the guys I know that drive Ferraris and Lamborghinis, they all have lifestyle businesses. They don’t like auto body shops, so they have, like, some like things and you know, they live in mansions and they drive Ferraris and no judgment about lifestyle businesses.
They’re just they just don’t follow the trajectory required for venture capitalists to make money. That’s fine. It’s totally fine. You get loans, you bootstrap, you make a business. It does great. It’s great because people want to buy, buy the product that makes or the service itself.
Jeffery:
No, I love it, I love it and that was very well, said I. I agree. So now we’re going to jump, and the reason why I agree with that is because people have not dived into all of these components enough to understand each piece of it.
So they have to leverage and utilize some measure to feel that they’ve got to win, and then they use that to keep building their next steps. They just need to shift around with what that wind looks like, and the wind doesn’t always have to be around venture capital or getting winds from the angels. It has to be winds that I got from my clients and then I’ve got market product, our product market fit, and then I’m going to be able to get those other winds. Those should be intrinsic value that gets added in after. Because when you build something great, VCs are going to find you.
Dony:
Yeah, Absolutely. Or you got a margin already and you don’t need VCs. (Inaudible)
Jeffery:
Exactly. All right, well, we’re almost at the end. It’s been fantastic. So we’ve got three questions.
Dony:
Okay?
Jeffery:
Your favorite movie.
Dony:
Ponette. French film about a little girl who loses her mother in a car accident. Unbelievable. It changed my perspective on film.
Jeffery:
What’s it called,
Dony:
P O N E T T E. No, just a stunningly beautiful film.
Jeffery:
And which character would you play in the movie
Dony:
In that movie?
Jeffery:
Which character represents you like, what character would you be?
Dony:
The little girl has a best friend, but they are like, you know, that it’s a very funny friendship, but his name is Mattias. I would be Matias in the film, like a minor side character.
Jeffery:
Awesome. No, Perfect. Alright, I was just going to start with your favorite sports team, then get into these.
But it came out faster because you’re in movies. I got so excited. I was like a movie question first, but favorite
Dony:
Raptors. (Inaudbile)
Jeffery:
Raptors, all right, I love it. Well, I do these questions because I learned from one of the one of the startups that we work with. I listen to their podcast, Um, and they interview, um, they have a couple of different ones, but the main one is that they interview sports celebrities in basketball and whatnot.
But they also have one where they interview the moms of basketball players. And it’s really awesome because they get to learn so much about the individual that you wouldn’t have got just by talking to him or in the case of the basketball, they do women’s basketball to which is phenomenal. So they bring all these people in together in their podcast, so it’s pretty awesome. And they always asked little questions at the end that are more personal, and I’ve never done something so personal. So I thought, You know what? I’m a challenge myself to find out something personal at somebody, and those were the best because I learned so much from the film that someone likes, but the character they pick, So then when you watch it, I actually learned more about that person thinking, Oh, my God. I can see how that blends. Yeah, that makes sense. It’s cool. People pick a character so close to themselves that it actually represents a lot of it’s pretty cool.
Dony:
That’s fascinating
Jeffery:
So, yeah, so I want to say Donny one, I’m so glad we got to finally do the interview. And I’m glad that we’ve been chatting this over this whole period of time and learning a little bit more and seeing all the things that you’re doing and you’re doing awesome stuff in the ecosystem, I’m gonna follow up with you after all of this because I’d love to continue chatting and picking brain and sharing some of the stuff we’re doing and and see where that may tie in with yourself.
But in the best of how we always like to close off our shows, we want to give you the last word. And that is to share anything that you want to say to investors or to start up any advice you want to give them. But we turn it over to you for the last word.
Dony:
Oh, my goodness. Right now, at this time and this day and age, I just want to wish everyone health, happiness and success. You know, uh, the top of that You speak health. You know, um, I spend every morning I wake up, and, um, I feel very I have a lot of gratitude for being in a circumstance where, you know, I’m not worried about my health, but I worry about everyone all the time right now, and my, my, my fellow Canadians and my fellow humans, Uh, all I do is just wonder if I could take a moment to anyone who’s listening and sincerely wish you good out in the next little bit. Um, you know that that for me is enough
Jeffery:
also. Well, I appreciate it, man. Fantastic. Thank you so much.
You did a phenomenal job as I always do. Took lots of
Dony:
notes. Thank you so much. Really appreciate it. Love what you’re doing. Love your support for the community. It’s so needed. And, you know, um, look forward to our next conversation.
Jeffery:
You bet I’ll book out something for you, but in the meantime, keep it up, man. You’re doing awesome. Thank you very much. For time.
Dony:
Chest go.
Jeffery:
Well, that was awesome. And so many cool. things just from the schooling, the types of investments they make.
I love the fact that he’s a Raptor fan, and I gotta check out this plan. A movie that sounds really
Dony:
cool.
Jeffery:
Um, and the film that he took his film, learning to tie that into creativity around helping startups and what he wants to invest in. So, um, and I like some of the stats who wrote about the 66% of, um, companies that receive funding. I will be taken over because they won’t operate. And maybe there’s a way to change that so that entrepreneurs will stay just as hungry as they did when they start. And then looking at this Porter’s five forces. Very cool. Um, either way, Donnie. Fantastic. Thank you very much for your time. Thanks, everybody, for joining us.