Angel Investor | Managing Partner at Canada Startup Company
Ajay Malhotra | Angel Investor | Managing Partner at Canada Startup Company

"This world's not made by people who give up. It's made by people who kept going."

- Ajay Malhotra

Ajay Malhotra on the importance of innovation.

Talk Takeaways

Angel investor, Ajay Malhotra, talked about his diverse educational background in Computer Science, Commerce, and Information Technology. He also shared a personal story of his struggle with Immigration which eventually led him to launch a new website,

Ajay explains how bringing in talent from all over the world to Canada helps the country in the bigger picture. He also discussed that entrepreneurship is 99% perspiration and 1% inspiration. The idea only comprises 1%, and the founder’s execution and discipline will determine how successful the startup is going to be.


An Experienced Entrepreneur and Angel Investor with Startup mentorship experience at MaRS Discovery District (world’s largest urban incubator) and Toronto Business Development Center ( Canada’s first Incubator ) and more.

Having been in the Startup Visa Ecosystem for 4+ years, we have leveraged our 10 divisions, mentors, advisors and strong due diligence to help over 65 international companies with over 216 founders enter into the Canadian market successfully through the Canada Startup Visa Program.

Canada Startup Co’s Venture Studio has worked with immigrant entrepreneurs:
– From 20+ countries in the world ?
– From over 35 different industries
– Working with both RCICs and Immigration Lawyers
– With various senior management, professional, startup or business ownership experience
– Understanding and navigating the Peer Review and Judicial review processes
– Advised, mentored and introduced founders to connections and partners in Canada

He’s been a serial entrepreneur invested-in and growing companies in Enterprise Software, Home Building, Fin-Tech, Algorithmic Trading, Digital Advertising, Enterprise Software, Virtual Reality and more.

Being the “best in the world” is not just a cliche with him, it’s practise – Ajay was a national level table tennis player, then the first person in a country of a billion people to have dual principal level certifications on IBM Lotus Domino. His last few exits were the world’s most flexible workflow engine and the worlds most configurable ERP system framework (core engine).

Ajay moved to Canada in 2009 after spending 10 years in USA. Today, he invests all him time and energy supporting Immigrant Entrepreneurs. CSC guides, mentors, invests-in and supports Immigrant Entrepreneurs in making things happen for them and their families in their new Country of Canada.

The full #OPNAskAnAngel talk

Transcription for Ajay Malhotra

Jeffery: Welcome to the Supporters Fund Ask An Angel. I’m your host Jeffery Potvin. Let’s welcome our investor for today and that is Ajay Malhotra. Thank you very much for joining us today Ajay.
Ajay: very welcome Jeffery, such a pleasure to be here.
Jeffery: Well we’re super excited not only because you’re here today to talk about all the great things you’re up to, but we actually get to work with you usually on a monthly basis through York Angels. and I enjoy actually working with you because I think you asked some great questions and you really know how to tackle the startup community. so we’re going to get a lot out of today’s conversation. So glad you’re here and maybe the best way for us to start is if you could share a little bit about your background from the Comp Sci side of things. I think you’ve been to many schools. you’ve done a lot of great things in it. It’s amazing. you’re kind of like a jack of all trades. you’ve done a lot of stuff. So, I’m excited to share all of that. but maybe, a little bit on the background too on the businesses that you’ve worked for and now kind of where you’re at today with Canada Startup Company.
Ajay: absolutely! Um, “Jack of All” usually comes with a caveat, right? It also means master of none. but i think i took my masters pretty uh early on, right in terms of getting mastery in one subject. so i used to be one of the leading programmers. in fact India’s number one programmer. On Lotus Notes and Dominance, I was the highest certified person in the country, before I left the country. In terms of background, yes, I have my Computer Science education. I have a bachelor’s in Commerce, as well as a master’s in IT. and Then I did a couple of courses in Artificial Intelligence and Financial Markets from Stanford. and you know it’s been a learning experience. It’s been a journey. So what I’ve always done is really taken on new things and then figured out what I need to learn. You know what I need to get under my belt to be able to achieve what I need to achieve in that scenario. and that’s one of the things i look for in founders too, people who have that attitude of throwing their hat over the wall and then figuring out how to climb it.
Jeffery: That’s awesome.
Ajay: I mean that’s pretty much it. Yes, I’ve worked in a few different countries. I’ve worked in Malaysia, worked in Singapore, and in Seoul, South Korea. i’ve worked in Washington DC, in Silicon Valley, San Jose California. and then i’ve worked in Miami extensively. and now about 12 years in Canada. Yeah, I’m old. You can’t even tell.
Jeffery: I swear to god, you look like you’re 25 to 30 years old.
Ajay: But you’re kidding Jeffery. you’re a great liar.
Jeffery: no, the video will prove this well. So Ajay, in this experience that you’ve built up, not only bouncing from different countries, working for a lot of big business and of course going through and getting educated in all these different sectors which I love, because I’m the same. I just love education. I love learning and I know the world’s trying to change the way we are learning and how you learn. and oh, you don’t need a degree. You don’t need an mba. just go out and get real life experience. I’m not sure I really believe in that. I really do think that a lot of our habits and a lot of our learning abilities come through education, from structured education. It really does help. so now, kind of fast forward through the education system. and you’ve really dived a lot into that comp sci and deep tech. Can you give us a little bit more of a better view of when you were working for motor oil, when you’re working in these companies, how did that experience really shape what you’re doing today?
Ajay: Oh yeah! So can I agree to disagree on one point though? I totally believe in the education system. I actually used to work for a company called NIT, which was India’s largest company. in fact, the world’s largest company by the number of people trained. I used to be part of the curriculum development side of things before I jumped on to being the Lotus Notes expertise side of things. and one of the things that we realized is education can only build a base, right? and then from there on, you need to leap up to any level of achievement that you want to get. today we hired a lot of co-op students from the University of Waterloo. We actually run a very successful co-op program and we realized that some of the smartest candidates still do not have specialist knowledge to get stuff done right. but at the same time, i’ll come to your point as well. but at the same time, i am a big believer in what Khan Academy or Sal Khan believes in, which is to avoid “Swiss Cheese Education”, you know. so just like swiss cheese, you have so many holes. so the goal is to avoid that, to make sure that you’re kind of complete in terms of your education. So I think some form of a degree or some form of a curriculum gives you that complete composure, that completeness to your education without swiss cheese holes in the middle. but at the same time, that thing would just make you well rounded so as to say right? but to be able to make any impact in life, you have to have a sharp edge. so you have to develop that edge. they’re gonna make you like a blob, well grounded. but if you wanna chop some wood, you’re gonna have to sharpen yourselves. and that edge comes from you becoming a specialist and a super specialist in one domain and that will only happen in the last three. because you know, necessity is the mother of inventions and you don’t have a necessity to get to that point in education right? The job of a university is to get candidates good enough so they can find a job. so they’ll get you good enough to find a job. From there on, if your goal is to make a unicorn, if your goal is to know to be the best in the world at something, then from there on, it’s on you to sharpen your skills. so coming back to your point of working for a lot of different organizations. So yes. I mean , I worked for Motorola. I did projects for GE. I worked for Citibank and I worked for Bank of America. I was a consultant all through and through which gave me such a huge amount of diverse experience. One of my first projects was with the Bank of America where I actually started my career. and selling for Bank of America, most people don’t know that they think that i have more of a tech background. but in the first two years of my career, I was actually just selling banking products. and from there on, i went on to work for Reserve Bank of India, the different establishments of India. and from there on, Prime Minister’s Office of Malaysia, Motorola Innovation Center, GE, Citibank then Applied Materials, then Saratoga Systems. There was a small CRM company in Silicon Valley called Saratoga Systems. I don’t think they’re alive anymore but I worked for them, then worked for Maximus in Washington DC, then Export Import Bank, then Royal Caribbean International. From there on, I thought that I was ready at that point to launch my own company. so being in the United States, you had to be very watchful of the Visa Situation which i had a huge amount of difficulty navigating that area. and that’s why one of the things i’m trying to do now is to help as many founders as i possibly can in terms of immigration. and in fact we’re launching a new website called “” so i’m funding that project. we’re very close. In fact, I believe the first Alpha Release is already out. so you know, it’s pretty much crappy right now. but it’s out and it’s a way of putting something out there. and saying how it works so very big on, making sure that immigrants, first generation, second generation, whosoever it is, any kind of disadvantage, entrepreneur gets a leg up in what they’re trying to do. at least they get the foundations correct and they get the networking that they require to make things happen. That’s pretty much been my journey till now.
Jeffery: I love that. and when you talk about this, what i find fascinating about your background, and of course a lot of investors, is that there’s such a vast array of Angel and VCs that all come from banking. it’s almost like it’s set in the blood of while working in a bank, they’re teaching you about startup businesses. they’re coming in. they’re pitching. they’re looking for money and everybody in a bank seems to just wrap their mind around how a startup or a business works. and then they go on to be investors. I swear everybody I invest in has worked at a bank or in some capacity, works in the investment space which I love, because they understand numbers. They understand how business works. they get the real raw insight and then they work from there. so that’s amazing. that and a lot of your background has gone through the bank system from tech or from a business perspective on selling, etc. as you mentioned. but i think it does carry so much value in this startup ecosystem, when it comes to numbers and making investments and to kind of pull back a little bit on the baseline for education. I love that. you’re saying that, that is a baseline because what makes a big difference about going to university or college is that you’ve created that baseline. your education level has got to this standard uh which creates the base. and then if you’re going to be something bigger, better, you’re going to have to educate yourself. you’re going to have to go to that masters. you’re going to have to go take all this learning that you’re going to do through Ted Talks and everywhere else. you’re going to build up your specialty and become that security expert or become that banker. all that information has to come from your drive to execute and get something to completion. so I, all heartily agree with that, that there’s such a big room after you finish that baseline. Exactly. and it’s important to finish that baseline. We very recently hired a programmer who claimed to be pretty good at VR technologies. but he had just finished high school. and guess what, despite his level, best in terms of attention, effort and potential. He could not achieve as much because the baseline was not there. but at the same time, when we get people from Borderloos Bachelor’s Programs and Masters Programs and Computer Science the basis there. So even if they’re struggling on one thing or the other, it probably takes a couple of hours to help them out and get them going on. It’s because the foundation is there. so it’s very important. as you correctly pointed out, they become a lot stronger on creating and solving problems. whereas if they don’t have that baseline, their problem solving may take longer, or just not being able to understand all the different components that go into trouble shooting. So I think that baseline really creates a lot of people that now can figure out how to work with other people. They can be practical. they can be technical. They can just dive into things and I think that makes a big difference. so i’ll give you a very quick example right. so one of the sprint planning meetings that i was in and i’m very technical. so i love to geek out right, with the developers, and um so i remember one of the architects was pointing out the fact that we were using a pre-ordered Traversal Algorithm. it’s a mouthful i know. but he’s like we’re using that and that comes with an update anomaly. So what we’re now doing is switching over to the MYSQL version, eight point something because that has recursive queries built in. and um you know, so most people with a Computer Science background said, that makes sense. So how were you maintaining the pre-order three traversal? and he said, I had a left and a right field, and you know, and those were the causes. and they’re like, yeah, I understand. and I remember this guy who’s extremely sharp in his domain and he was there. but he didn’t have the fundamental basic level of education. and he’s literally like scratching his head and saying, do i say something and look stupid, or do i just not say anything at all? So yeah, you’re right, hundred percent. get your foundation, get a strong foundation. but remember, it’s just a foundation. it’s just a plateau from there on, it’s your ability to move hard and fast. and you mentioned something else, that’s pretty interesting to dive into. and you kind of alluded to. you kind of have to, after you have that baseline, you have to build the structure of execution or how to keep propelling yourself forward. So I think, when I look at founders and you kind of alluded to this, you have this criteria that you’re looking for about how a founder should work. or the things that they should do, how high on the list is execution to you when you’re looking at a founder?
Ajay: It’s all about executing Jeffery. I mean, people say, oh I have an idea. I have a really brilliant idea and I think uh it’s a million dollar idea. or a billion dollar idea. and i tell you, ideas are worth exactly what you can sell them for right, which is zero. if it’s just an idea, the rest is all execution that piles up on it. It’s 99 percent perspiration, one percent inspiration. inspiration is that idea, the rest 99 percent is the execution so 99 of all i have. huge respect for uh for managerial talent who bring execution discipline into an organization. I have a huge respect for sales talent which adds to the bottom line of the organization. I think you know Google, and I’ll give you an example here. so i’ll, for the audience, i’ll specify why i’m bringing in Google, right. Everybody talks about the fact that the smartest people in the world kind of go and work for Google, okay. But why is it that still today 96 or 98% of Google’s revenue comes only from search engine advertising right? they’ve had a decade, 15 years they haven’t been able to create a single secondary source of revenue because they geek out and they respect geeks. but they do not expect people who could bring sales, who could drink traction, who could bring execution discipline and I think those factors are important. I mean look at Google. even doing their pixel phones, they try to just basically stay in the shadows of Apple. so it’s always Apple going ahead and launching something the next day. and Google said, ah, we were left behind. Let’s do something good enough to get there. and that’s one of the things that I look for in founders. Are these guys going to? and why do i look for it, because primarily most businesses that are there today are the types that the winner takes all approaches required in those businesses, right? so i look for a person who’s going to have that execution discipline, to be in like the 24th mile and then still keep putting all the energy in. and that’s what’s required. you know you’re there. you literally feel like you’re winning. but still you’re beating. You know, you’re kind of competing with yourselves. you could say that. I want to be even better. I want to be even better, right? and to some extent, it’s borderline between, some kind of psychological. I don’t even think of those things. but like so i wouldn’t know the names. but almost borderline where you could say, hey this person is a psychopath. but some amount of that is required to bring that execution discipline.
Jeffery: I love that you say that because I was told that I shouldn’t use that term, which is, I look for psychopathic or psychotic founders. So I had to change that. and I now look for founders that have extra gear. they’ve got that sixth gear. Everybody’s working on five and they’ve got this extra gear they can just kick it in and that helps them just keep getting stuff done, just keep plowing forward. I think it was when they looked at Kobe Bryant and a lot of the superstars. They said they just have one extra gear. they can be out playing but they just have that one gear that you just don’t have and that’s what i look for in a founder is that they have that gear and it sounds like that’s the same thing that you’re looking for, which is that psychotic or um a little bit of the uh crazy side. but that crazy side is just that they have this other gear to hit that 24 hours or hit that extra mark that’s going to bring them over and above on thinking and execution in their business. I remember I invested very early on. i invested in a founder where i went on a hike with some of these founders, and this person was almost a psychopath, in the sense that we were in a very long hike as everybody got tired, this person started demonstrating you know, maybe he didn’t get tired, but at least he started demonstrating the fact that he was not tired at all. and he made everybody feel even more miserable. and trust me, i got about 12x back from him. So, that’s what you need when everybody else is getting tired. could you still keep going on? It’s all about execution. it’s all about getting done. I love that you’re right. it’s when you hit that extra gear, so many more things can happen and more people get behind that because then that starts to drive out scaling. It starts to upset the business, investors, people that are buying into it, people that are reading about it, they start to see that this has such fast legs and that they need to be part of that and then herd mentality jumps in and everybody wants to be part of that. so that’s some great insight. Now that you know these businesses and you’re making investments, you decided to kind of jump more into this space. you talked a little bit about how you’re working with Bypoc bringing in immigration and helping them get into startups, or even get into a country working on startups? Can you give us a little bit more understanding of how that process works and how you guys are kind of reinventing how that space is going to look? Because it’s something that’s obviously coming up really close to being pushed to the market that you’re working on.
Ajay: Absolutely, you know, one of the things that happened with me personally is, i was in the united states and i was getting my H1C and all of that stupid process. I mean that thing feels like a never-ending loop of things. and then every so often, you would need to fly out of the country, get your visa stamped, come back. there was that huge sense of instability. and then one of these years we were coming back, i believe it was 2007 or 2008, we were flying back from France. so me and my wife decided we’re gonna have to celebrate valentine’s in France this time. We went there and had such a good time in Prairie. As we flew back into the Miami Airport, this guy pulled us over and said, son, I’m not sure I can let you in the country. At that point, I had a successful business there. I had employees there. I had a house there. I had dogs there. that just scares the crap out of you. you feel like, oh my god, somebody could literally pull the rug underneath my feet. At that point, we decided that we needed something stable first. When we looked and we moved into Canada, it gave us that really beautiful foundation of a first world country, a social safety net and a fairly easy immigration process, and straightforward immigration process in the United States or ST on lawyers and processes. and i have a huge bunch of just notices for actions, seven nine sevens, one four zeros, 485s, you name it. it’s all there. so it was one of the things that i decided to do a few years ago when i saw some founders struggle with that thing in Canada. so my personal experience was so seamless, so beautiful, that i didn’t think anybody would struggle with it. But a few years ago, I noticed that people were struggling with it, and especially with the startup visa process, and this was very close to my heart. I’m a very innovative person. I like to always work on new things and these were people who, I believe, were creating the next set of businesses. and so i wanted to really help and support them. and i realized that the visa process was really hurting quite a lot of them. It was long. It was arduous. It was very expensive to go through a lot of lawyers. and at that point, i decided to jump into it. and as i jumped into it, i realized that i could streamline some of that. and a lot of people absolutely love that. and then down the line, we realized that there was some education component that was missing as well. So now, we’re in the process of launching what we believe is the world’s most comprehensive education program for startups. As an acceleration program, we call it the “Karman Line”, which is the name of the virtual line at 100 kilometers above earth, where space really starts. So that’s what we’re up to, hoping to provide them the right education, the right mindset, the right understanding of the market, the right connections here to make sure they can really flourish our goal. and we keep our money where our mouth is. We reinvest literally all the dollars that we make in consulting. we go ahead and make sure that every company that we’re bringing in, we have an ownership stake in them. so we’re not like regular law firms doing consulting. We take a stake in every one of them and our goal and hope is to grow at least a few unicorns from there. We believe that Canada has about a 37 million population and I can be pretty sure that a country like Iran or India has more than 37 million programmers there. So just because of the population dynamics, a large city in India is the same as Canada’s entire population. So our hope, dream and goal is to be able to import quite a few of the good programmers and founders into Canada and help them build the next set of businesses. People make mistakes saying that, hey TD has always been here, and they look at those businesses and they think that past performance is an indicator of the future, which it never is. The average lifetime of a business on sp 500 is 16 years. the average price earning ratio, i believe today, would be 28 or something. which means you’re paying 28 x today for the hope that they even survive 28 years. but on an average, they’re gonna survive 16 years. So at this point Canada or the US as a country needs to start laying down the ground foundation. We’ve got to start planting the seeds in and that’s why it’s called seed investment. so we’re going to start planting the seeds to make sure we can grow the oak trees for the next 15 – 20 years.
Jeffery: I love that and I think that’s a fantastic initiative to build up in a sector that Canada is deemed as being stronger in. and it’s great that you’re being able to bring talent into the country that’s going to be able to be that next generation of, not only founders, but employees, teams, investors that are going to really help drive the country forward into the next millennium. but that’s pretty exciting to hear. Now, I guess taking that is that broad. you mentioned India and Iran. is that just those two countries or are you opening this up to any country that’s looking to find great talent and immigrate to any country?
Ajay: we’re open to the entire world. We’ve had some very successful founders from china. We’ve had some very successful founders from the United states. In fact, the prime reason that I started this off was a founder from the UK. So yes, we’ve had founders from all over the world. and a lot of them are doing real cutting-edge, fabulous work. my thinking is that some of these guys would actually build the unicorns for tomorrow. These guys would actually build the neo banks which would potentially replace TD. I’m very passionate. I’m very driven about it because I could see that happening.
Jeffery: I love it. No, that’s very exciting. and this kind of makes me think that while you’re kind of bringing in all this great talent, where does this fit for? and in the eye of using ai and machine learning, where do you see this technology changing? Do you think that bringing in this great talent into Canada is going to make us stronger, better, uh even more competitive against the silicon valleys of the world or Switzerland, Sweden or Finland where they’re doing a lot of phenomenal things in Europe? Where do you see this all fitting together?
Ajay: So you know, as an investor, we always have to speculate every day. and we get very good at it. so you look at a company and you start speculating. so they are telling you their time and their forecast but your mind’s already racing ahead and saying what could they potentially capitalize on, how much would they be worth in five years. so we get very good at it. Needless to say, we always keep doing it. to the audience, please take it with a pinch of salt. it’s just my opinion. but my thinking or vision that i’ve drafted out, or my kind of view of what’s going on could happen. I believe that crm and ERP systems ate a huge portion of manufacturing slack out. so they literally chew the fat out of all of those processes. The reason we haven’t had massive inflation despite tons of qe and tons of money printing is because our manufacturing processes have gotten leader, leaner and smarter. And there’s been just in time and all of that innovation that’s happened in that area. but at the same time, these systems were able to do that but they were not able to do anything for services. so prices in terms of services have been rapidly climbing. an average lawyer used to be worth about twenty dollars an hour. Now they’re about four hundred dollars an hour. So I think artificial intelligence is where people feel people do not agree with this most often. but i think what artificial intelligence is going to do is going to bring that level of efficiency and cost reduction in services. and that’s i think the next big set of companies. so, they will go ahead and achieve that. but beyond that, i think we could capitalize this in the next five to ten years. By the time we have some form of artificial journal intelligence coming in and then beyond that, I think it will be really at that point that artificial general intelligence is slightly smarter than an average human being. so, you would let it provide more services and more information. is a great example that system’s been able to digest about five million different documents to be able to spit out what you should look for out of the hundred different immigration programs of Canada and where your probabilities would be higher. I’ll be hard-pressed to find a single lawyer in the country. maybe there will be one but not a lot of them who would know all of that information. so, the ability of AI to be able to assimilate all that information and then be able to spread that out really rapidly and learn very effectively I think would cause the same implosion and prices that erp and crm just in time caused in product. and at that point, Canada or any country would need to be focused not on services but on innovation. right we used to calculate the economies of most countries in terms of agriculture output. that was primarily the largest part of GDP. and then from there, it moved over to manufacturing. from there, it moved over services. Now it’s very rapidly moving over to innovation. Okay, you’re gonna have to create new things. you’re gonna have to bring something into existence that was not in existence before. and I think the moment we jump into innovation at that point, one of the areas that’s been very much behind the curve is the entire synthetic biology, life extension. I was reading some material off lately. Where is the lifespan, that’s a book there. I’m not yet done with it fully. but the concepts are that an average human can very easily lift over 180 years. and the theoretical maximum on your life is about 800 years. so we do have those as the next few items we could look at.
Jeffery: I love that and I guess to unroll that a little bit, innovation is so impactful to the GDP to your comment that they estimate that 50% of the GDP growth is associated with innovation. so that’s only going to keep increasing. so that is such a significant change in how they used to monitor it to how they’re monitoring it today. and I think that on the Canadian side, there’s certainly a lot of opportunity for innovation to move forward. I don’t remember the gentleman’s name but in 1967, they wrote a paper and they said where does Canada want to be in the 2000s and they came back and said, we are going to be management. we’re going to be the thinkers and we need to shape the economy to go to that state. so people are going to employ Canadians to go all over the world to help them build and grow their economies. and you know that’s how the markets changed. and it has to keep going that way which is all around innovation. So hopefully we’ve been able to prove that and continue to grow that model out as it is shared because it makes a big difference. and it’s a huge impact today on how our GDP is going to move forward. and immigration is going to play a big role in that, absolutely. I mean, as global warming happens, which is going to happen right north, passages are going to open up. People don’t realize how close we are to Russia there. so we will have to defend our territory. and with a population of 40 million, we cannot defend this land. so you know, you’re going to need it. and your military force is a factor of your GDP as well. so you’re gonna have to grow your gdp at least two and a half times. you’re gonna have to grow your population two and a half times. I can’t see Canada being able to defend our coastal territory without a population of at least 100 million people.
Jeffery: It’s a very interesting point and you’re right that we have a very vast area of land which is under populated. but in cities they’re saying we’re overpopulated. so i guess in terms, there’s a lot of outside growth that can occur but it’s to support the economy, to support the growth. but even, eventually it could be just supporting the country for other means as well as the world continues to shift and change. Absolutely. China is getting stronger. Russia and China have a lot of economic benefits or ties with each other and Russia has always been a little bit aggressive. if you look at their entire history, you’re gonna know. you prepare with the hope that you never have to go to battle. but if you don’t prepare, then there is a good chance that you have to go about them for sure and you can’t always lean on everybody else. and that battle could be just a battle of brains which is around innovation. and who’s the smarter, quicker, faster country to be able to maneuver and make things happen quicker. so um but on that, i’m gonna kind of shift a little bit. and what question i want to dive into is what are the, you know we mentioned before, the one major thing that really interested you about execution and that really drives you about making investments? Are there maybe three or four top level things that you can share that you look for when making an investment?
Ajay: um, you know the d7 of venture capital that everybody looks at? the team technology attraction, so i go through that too. but you know, i always go back to the same founder that i was telling you about where he delivered 12x versus i lost quite a few different investments which every angel loses quite a few. I mean that’s the right passage. and i remember the one thing unique about him was when everybody else will stop, he will still keep going. so i always typically look at the energizer bunny. so it just keeps going. That’s my number one thing to look at. The second thing that I look for is, I never invest in companies who do not have a tech partner or who do not have a partner who’s actually going to manage the delivery part of it. So if I’m investing in a biotech company and they do not have a guy who can actually whip up the miracle whatever they’re selling, I’m not investing in it. because you would never invest in a restaurant that does not have its own kitchen. Would you? That’s my second biggest point and I think I’m able to disqualify about 99 of the companies with just these two criteria. number one, the guy has his own kitchen and number two the fact that the two or three founders energize their bunnies. could they just keep going on and on? because at the end of the day, look, you know they’re going to have to fight the world. they’re going to have to outwork everybody else. That’s the execution discipline. most of this stuff, you could teach them as long as they’re coachable.
Jeffery: agreed with that. and I like the analogy. I guess I could put a bit of tire iron in it. It’s that today there are a lot of ghost kitchens that are coming up and there are a lot of places that are working that way. So I wholeheartedly agree that in order for that to be successful, you need these things. but with innovation and change, and turning things into cookie cutter, nowadays you can have somebody that’s writing no code and they’re still being able to build a hundred-million-dollar business off of no code. so there is some risk level of trying to understand. and where the world changes to it, it’s also looking at. and i think we were on a call where someone was pitching and their founders were spread all over two continents, they didn’t have an office and they were raising funds. and in your mind, you’re saying, how does this work? like am i putting the money in here that goes in the US? and where is the revenue recognized? and who owns this entity? is this someone i want to invest in? but that’s the world we live in. so it’s now trying to pair in all of these changes in deciding how impactful is that going to be to make money that company. and can i get on board with that you’re 100% right. i mean, world’s changing and change is the only constant. regard the fact though is that a few companies will actually end up capitalizing on that change. but no code and low code frameworks make it much easier to get the job done. and i haven’t yet found a company that took something which was very easy to do that a lot of other people could do and make a unicorn out of it. so you know a few of them would be successful by the time everybody else catches on. so my goal will always be to invest in stuff that’s extremely hard to do, that not a lot of people in this world can do potentially and thereby, i think, my odds of success would be a little bit higher.
Jeffery: I love it. That’s great. and I totally agree with that. The people that got to work the hardest are the ones that find their way to success. it takes a little bit longer but they got to put a little bit more into it. but at the end of the day, if it was easy, everybody would do it. During your 20 to 30 years that you’ve been working with big tech, now working in startups, I always like to get this heartfelt story about kind of what it takes to be an entrepreneur. and maybe you can share a story that you’ve seen where she or he as a founder really just totally blew your mind away on what it takes and how amazing it is to be an entrepreneur. and maybe you have a story that pops in mind that you could share with the community.
Ajay: absolutely! I met this one entrepreneur in Goa, India, of all places. Again, he had the few key characteristics that I look for – extremely hard working, extremely technical. so he could basically take a thing apart but wasn’t getting much success anywhere. and those are the kind of individuals that I would look at supporting. and I remember that we supported him at that point to get his first version out there. The next time I heard from him he was selling the product in New York and he’d landed a few big accounts in New York. then unfortunately, the whole covet situation caused some of this stuff to shut down in New York. he had opened up a mechanism of being there permanently on an H1b visa or something like that where he was employed by his own company and some legal way of doing it which he had to now get back to his roots. so now we’re looking at bringing him into Canada instead and saying you know what a more stable, more equitable foundation. but you know, taking somebody who was struggling and considering himself as a misfit in the culture and the atmosphere and then giving them the leverage that they’re actually able to go to top-tier firms, and this was in the digital advertising space. so going to top-tier digital advice categorizing firms in New York and selling them their product very happily, that’s one of the things that comes to my mind. so it’s a great story. so he was able to overcome the barriers that were thrown in front of him and then shift and keep using that accelerated sixth gear and driving himself forward. I mean they were, oh my god, so many things that went wrong. You know, I can’t even tell you everything that went wrong in that business. and it goes wrong in every business. One of the things that I learned from one mentor of mine was, hey listen, the first day you get sued is not that you did something wrong. but think of it like you’ve achieved something. No, now you’re worth being sued. So yeah, as you grow your business, anything and everything will go wrong. That’s where the sixth gear comes in. you just keep going. you keep going regardless. you keep going.
Jeffery: oh, that’s awesome. That’s great.
Ajay: Yeah, someone told me once that when you’re getting sued, that was you earning your stripes. and i looked at it and said, you know four times, i’m getting, this is ridiculous. so i don’t want to earn any more stripes. It’s time to do business. so i get it. It’s part of life. but it’s also how you persevere and overcome adversity and drive forward. and do it in a clear thinking way. and i think that makes a big difference on the potential and the opportunity that’s going to be in front of you. this world’s not made by people who give up. It’s made by people who keep going. so if you are the kind that’ll give up then, you’re not getting my money and i think you’re not getting JP’s money either.
Jeffery: I have to get you to repeat that line. I gotta write that one down. That’s awesome. so the world’s not made by people who gave up. the world’s made by people who kept going. Yup, i write down every single line that i think is amazing. and then that way, i can reference it later. so that’s a great line. so you’ve made it into my uh excel spreadsheet of awesome lines.
Ajay: Thank you JP.
Jeffery: Yeah, that’s brilliant. Okay, good. alright now. we’re gonna transition into the rapid fire side of things. so in the rapid fire, just pick one or the other. It’s pretty straightforward. Okay, first question, founder or co-founder?
Ajay: co-founder.
Jeffery: unicorn or four-year ten times exit?
Ajay: four year ten times exit.
Jeffery: brand or tech? tank ai or blockchain? first time founder or two three times founder?
Ajay: double failed founder.
Jeffery: Okay, well that’s a good twist. I like that. first money in or series a?
Ajay: First money in.
Jeffery: angel or VC?
Ajay: angel.
Jeffery: board seat or observer seat? safe or convertible?
Ajay: note, i’ve done both. Obviously as investors our preference is economical.
Jeffery: lead or follow?
Ajay: follow.
Jeffery: equity or interest payments?
Ajay: equity.
Jeffery: favorite part of investing?
Ajay: speculation and ideation.
Jeffery: I like that, speculation. number of companies invested per year?
Ajay: close to 15.
Jeffery: brilliant. preferred term? any preferred terms that you like?
Ajay: right of first refusal. vertical of focus. um as i mentioned ai for right now. and then the next evolution, which would be my personal evolution as well, getting into biotech.
Jeffery: I love it. well we already talked about what things pop out of the startups and you mentioned two things. so we won’t go into that. Alright. Now we’re gonna go into the personal side. So one thing about you that nobody would know?
Ajay: crazy man. so i have been fired three times for being an overachiever [Laughter] Jeffery: Alright, that’s my first time hearing that. That’s brilliant.
Ajay: Okay, the first company fired me because I would stay till late and study and they couldn’t understand why that was. so they thought that i was unhappy with that job and wanted to switch. six months later I was the highest qualified person in that particular domain and their team came to me for training. The second time I got fired was because I was given, in my opinion, almost a clerical job of manipulating data and publishing it. and I had written code to entirely automate it. I didn’t realize that I was shooting myself in my own foot. and The third time I got fired was in Washington DC where I wrote an excess control system for an erp which they didn’t understand. so i was told, couldn’t you write simple code? Why do you have to do magic? I wasn’t fired. but I realized that it was time to move on from there.
Jeffery: That’s awesome. I love that. great story. book or movie?
Ajay: book.
Jeffery: Superman or batman?
Ajay: Oh man wow. Batman fights crying.
Jeffery: pizza pop or ice cream bar?
Ajay: ice cream.
Jeffery: five minutes with Bezos or Oprah?
Ajay: five minutes with Bezos.
Jeffery: alright, arsenal or anything?
Ajay: (sadistic laugh) I like that.
Jeffery: Arsenal or Manchester united?
Ajay: I’m not into sports at all. so okay, alright so that one won’t work. You know, I’m more a believer of doing your own selves so I’m not a spectator kind of a guy. That’s probably what you gathered from me, wanting a boat seat too but not wanting to do a little bit of hard work in terms of leading around. but very few people know that. I used to be a national level table tennis player. So I like to play but I don’t like to watch. I’m sorry.
Jeffery: That’s okay. you can be an inaugurated arsenal fan. I’ve been looking for Arsenal fans. so that’s good. Alright, bike or rollerblades?
Ajay: bike.
Jeffery: trophy or money?
Ajay: trophy.
Jeffery: beer or wine? Alarm clock or mobile phone?
Ajay: mobile phone.
Jeffery: hotel or hostel?
Ajay: hotel.
Jeffery: king or rich?
Ajay: king or rich, as if they’re not synonymous. Rich, yeah it comes with less liability. Yeah, less things you have to do. social pretense, so less social potential.
Jeffery: Is Trump an a or b on his efforts?
Ajay: Donald Trump, you mean?
Jeffery: I’m sorry I meant to say Trudeau. Trump was another question that I was avoiding. okay Trudeau, is he an a or b on his efforts today?
Ajay: I give him an a. I love this guy so I think it can get better. Does it usually get a lot better than this? it doesn’t.
Jeffery: Okay, I like it. The other question was does Trump go to jail for his taxes? all this tax evasion, yes or no? would you want him in prison for tax evasion?
Ajay: I mean you know Trump’s one of many exactly.
Jeffery: So I just avoided the question because I was like, I’m tired of trump. so i just took the question out which is all good. Alright, we’re almost there. even though i’m a die-hard liberal, in which case in the United States term, it makes me a democrat. but you know somehow, i still feel that a lot of the agenda that Trump brought forward was actually fairly good for that country. you know they have been losing out on trade talks. they have to get smarter and wiser about what they need. Do I believe in people wearing white dresses and conical hats? No, I don’t. but i think a lot of their agenda was good for the country. it did shake things up. I think the question I should have is, without Trump, has life become boring? Because it has become boring. it became boring without josh i believe. yes, he did that as well, then he would get lost halfway in a sentence and he’ll go like, you know fool me once, shame on you. Fool me twice and then he’ll get lost. He’ll be like what do I have to say next? then he’ll say no, you basically cannot fool me twice. [Laughter] Ajay: yeah you should have written half this stuff down. it would have made life a little bit easier for him. It’s all good.
Jeffery: Alright, what is your favorite movie and what character would you play in the movie?
Ajay: I’m a big sci-fi fan, so you know Captain kirk. any star wars or star trek movie, sorry.
Jeffery: Perfect, that’s awesome. favorite book?
Ajay: a favorite book that sticks around for very long with me is Jim Collins’ Good to Great.
Jeffery: Okay, it’s a good one. I like that.
Ajay: I think some of the companies that he’s referred to there which he pointed out as great have now disappeared. but that and one of the first books that i read was Bill Gates and i’m trying to remember the name. it was all about the DNA of an organization and if i remember the name, i’ll teach you that name.
Jeffery: perfect! I’ll look that one up. Alright, last question. What is your superpower?
Ajay: What is my superpower? i believe, just like how ai works in terms of taking in numerous amounts of data and then spitting out a particular result about it, i think that’s pretty much my superpower. I can look at, you know, 250 balls up in the air and 250 different dimensions of data and then be able to analyze them. and say, oh no. But you know we think this is what’s going to happen next and this is what this company should focus on.
Jeffery: I have a red button. I’m pushing it right now. Yeah, man that’s awesome. I actually had an image I’d throw up with. but i’m a big fan. it works the same way with my brain, just loves data. just scramble it, come up with nanoseconds of feedback. but i think that’s a great skill to have. It is being able to sweep away all the clutter and all the things that don’t need to be there and just go after what makes the most sense and push forward on.
Ajay: That’s brilliant. I love that. Well Ajay, I want to say thank you very much for all your time today. I know we had a bit of a minor glitch. maybe no one will ever know. we’ll be able to edit through that power outage but at the end of the day, it was fantastic getting to chat with you. I learned a lot, took lots of notes as I always do. I’m old school so I have to write things down so that I will never forget it. but the way we like to end our show is we like to give you the last word, so anything that you want to share to the investors or to the startup community? we leave it to you. but thank you again for all your insights and for sharing that was brilliant.
Ajay: thank you again JP. and this was such a pleasure talking to you and i’m kind of old school too. last words i would say, you know, from a perspective of where the world’s going next, i think innovation is extremely important for a country like Canada where we have massive amounts of natural resources, innovation is extremely important. we’ve been till now. We always practice our life as if we’re sleeping next to an elephant. That’s how our politics are. That’s how our innovation strategy is. People have been telling me that even IRCC, which is Immigration Refugee and Citizenship Canada, also looks at companies coming to Canada as people who could exploit the American market. I think it’s been good for a while. It’s been good for us. but i think what we have to do is like, China build the country from within. I think that’s one of the things that we should start doing. The demands for the United States are going to be different than the demands for us. They want to focus on Spanish. We will focus on French. they would want to focus on paving as many roads so Ford can sell more cars. That’s probably not an important thing for us. For us, it would be about bringing more tourism into the country or exploiting the north or being able to mine underground. I don’t know why the hell are we not investing as much on hyperloop technologies and on underground tunneling technologies. I mean today you could have a second city 100 kilometers north if you tunnel all the way underneath. you could spread your population. you could mine the entire area or significant deposits if you could just mine underground without destroying the environment. so there are technologies and innovations that are going to be relevant to our country and we have to develop them. and i think we have to have open arms to the best talent in the world coming over to us. America was not built only by Americans. they had the largest brain drain from the rest of the world into that country. In Canada, we’re going to do exactly the same. and then we can invest in them. we can’t just bring them to the country. i think we gotta empower our angel networks to be able to effectively give them that first dollar, that first guidance to be able to grow those people. and the reason why i think that’s fantastic, i’m going to have to introduce you to an investor from Estonia or they’re building an underground tunnel into Estonia and these guys are awesome. His name is Custa and we did a double segment with this because it was so phenomenal on how they set this up with tunneling to Talon which was from Helsinki to Talon to connect those startup ecosystems and those two countries together. and exactly what they did is exactly what you’re talking about which is finding ways to be innovative. tunneling underground, moving and dispersing people and being able to do it effectively without affecting the rest of the world, the ozone and everything else around us. so i love that. some great advice which also shares the fact that there’s a lot of stuff that entrepreneurs can start thinking of and start mining their own opportunities in Canada. and there are a ton of them. We just got to start being more innovative and thinking outside the box. There’s a great idea for an entrepreneur. Hey, you know Mr. Trudeau, I’ll build all your tunnels for free. just give me mining rights to every deposit that i come as i tunnel through it. We know there’s diamonds in Canada, there’s gold in Canada, all of that stuff. if i’m tunneling through it and i hit that pocket, that deposit is mine. but i could tunnel for free.
Jeffery: I love Ajay. you’re a brilliant man. Thank you very much for all your time today. We will obviously stay in touch and look forward to seeing you at the next screening meeting. but thank you very much again for your time.
Ajay: Thank you so much. It’s such a pleasure being here.

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