Cory Janssen. 17 Years Post-Exit: Insights from Investopedia’s Founder

35:52I think of selling as you have an asset that was illiquid, but you know very, very well, to now you've got liquid assets that you probably don't know anything about managing. So I'll give you two examples. Once we sold, we didn't do anything stupid. We didn't go buy a Lamborghini or anything like I shouldn't say that's stupid you know what I mean like we didn't we put money just in unnecessary exactly right and it's totally fine but like we we just we like for the first few months we said we're not gonna do anything we just kept ourselves kept it in treasuries right yeah but so I'm Canadian we sold in U.S.

36:33dollars we had everything just sitting in U.S. dollar you know cash basically the Canadian dollar the exchange rate right after we sold went from like something like 1.25 1.3 to par so on paper we were losing tons and tons of money every single week every single year so and we did all the right things right like we yeah we weren't and then so so then you're like calling the bank and putting in place these like complex sort of like fx callers and hedges on this i don't remember like i mean wasted 100k or something like this on some almost costless collar, right? To like protect downside, right?

37:17But it was, it was, it was a different type of stress. And again, the whole, the whole thing of like, okay, check. I want to, at entrepreneurship, I'm good on this. No, all of a sudden you have all these other problems, but you realize you're actually under equipped. How do you pick a wealth manager? Where do you go? Everyone's calling. Everyone wants something from you, right? How do you do philanthropy well? You know, like, do you just keep on giving when someone asks you what if you don't have a philanthropic plan right you know never mind getting into the family office side of it actually managing in that way if it's of that scale um and then so i was managing internal capital and you know i'm a big buffett disciple read everything he's ever had um and this was the financial crisis so i remember i was buying amex's stock and you know you know like the value style so i went down bought a little bit more gain down follow up more so you're kind of dollar cost averaging in right and then and then the market crashes in 2008 and so meanwhile so i'm literally down like seven figures on this one stop oh wow and i hit my position limits like i had like a good policy statement everything i had went through right and and i remember watching on cnbc like an amex was like at 15 bucks or something like that and buffett was going i would buy more of it if i could right like i'm i'm you I'm already at a 10 % threshold.

38:42This thing is like, Amex will never be this cheap again. You can probably go check the stock today. It would be probably a 10 or 20 bagger from that point. But I'd hit my position limits. I tried to be disciplined, right? And so meanwhile, I'm down this massive amount. Now, in the end, it came back up and I made money off it. But that round trip, holy cow. I mean, I never had that amount of stress in the business running it. So I sum it up this way. Beforehand, your net worth was here, right? And every month, every quarter you go up and you're happy. Now your net worth is here, but there's a little, you're still way higher than it was, but that delta, the change of that month, that was very stressful, right?

39:24And so this whole idea of like, well, you're this superstar. You just had this X, you have this, but you're actually a shitty investor. Yeah. And even myself, no matter how many books you read, you don't know until you're down. Until you're down that and in something until you're in it and you've, you've hit it, like you can't, it's almost like the same thing on a business. You're not like, you know, until you've had struggled to meet payroll. Right. It's like, I don't say you're not an entrepreneur, but like that's sort of like most entrepreneurs you've talked to, like they've, they've at one point been like, okay, I got a frigging mortgage the house or it doesn't matter if you're Richard Branson or anybody else, you've had to go all in.

40:00Right. Until you felt the pain of that on being an investor, you know, you haven't, you're not sort of battle hardened, right? Yeah. You know, most people I talk to admit that they went down financially before going up, because you also have this trend, especially these days, to go into angel investing or trying to buy another business, thinking that you can combine lifestyle and, you know, running a business all in one if you buy a business. So that basically takes me to to the next topic I really want to explore with you like what did you do next in terms of you know a new business professional investing I made about after you realize you're a horrible investor and in public equities yeah the one example I'd like to think I'm not not the worst it wasn't a great market for that right but i of course i had a bunch of wins as well i i actually i had a bloomberg terminal i would my claim to fame was be like you know the one guy with a bloomberg terminal in some industrial park in south edmonton right like you know and and i was actually just managed i spent all my day managing capital right so i did do fairly well in terms of um just but i was like like it was like rights offerings spinoffs merger securities just really esoteric like kind of deep value stuff right and and so but spending when i was spending 40 hours a week just reading like i i could do okay right that so but um kept on getting drunk so as i saw opportunities locally i made investments not no really know what i was doing and probably had too big of a position limit and then what i've learned is like when you start buying private companies and you're the biggest investor there, when things go down, you're now the bank.

41:54And so the mistake that I've made over the years is going in and then wanting to be a good partner versus like, as much as everybody gives private equity, you know, heck, like, sometimes you got to cut your losses, right? Sometimes you got to put something in the liquidation. And so I've always took I took my entrepreneurship side of being a good partner. And applying that to the financial world isn't necessarily the best approach has been my experience yeah absolutely so so my public stuff was okay uh some of the private stuff was there but then people kept on saying hey why don't we do the investopedia for this industry that industry think like really traditional boring industries that hadn't yet moved online so corrosion mitigation or industrial safety so we i took a couple million bucks threw in um you know built a platform to cookie cutter other pedia sites so essentially i built a cms like keep in mind wordpress for those who are technical wasn't you imagine 15 years ago you know you actually need to build from scratch you wouldn't today um but we launched about 10 of these uh different websites and they were okay but i think the lesson there as i reflect on it is that i didn't want to be operational and so i built the tech platform and said hey you know we'll be your partner from the technical side and try to get others to come in.

43:16And, you know, we didn't call it a venture studio, which I'm an adventure studio today, but like on paper it worked perfectly. But I think what I didn't realize at the time was how much of it is the founder that really is just driving it. How much that grit, if you have someone that really wants to get it done, like how important that is. And so we had some success, but, you know, my life is now good. I'm not going to go back working at that point, 70 hours a week jumping in on it. Right. I want to almost mentor and coach from the sidelines. And it just didn't work like that. The sites that we ran ourselves that we can control, we actually made some money with like not it wasn't the best level.

43:59I mean, they were very profitable. But, you know, trying to have that passive income stream and replace that Anastasia was like actually super tough. Right. Because remember, interest rates went down to nothing. and so you're putting all this money into these new businesses and you're like okay like i've got like an infinite runway but even after five years of not taking a paycheck and just putting stuff into it you start feeling it right so so you closed them that's what you did um no well no we have we've we we ran a bunch of them so what happened actually this is how how i got into ai in 2015 yeah i so we had a bunch of freelancers so the what i did differently is i built this platform so I didn't have to hire any local employees.

44:42I could hire freelancers around the world. And so we were spending so much on those freelancers that in 2015, I approached some professors at the University of Alberta for a project around algorithmic content generation. So 2015. Again, very early on. Gen AI was not, there was no hype. It wasn't even the term yet. So the technology that enables large language models called transformers came around late 2017, early kind of 2018 so we're early and um you know i like to uh joke with with with with nicole my partner that you know hey i was i was a visionary here and uh she says when you're three years early you're wrong she's right she's wrong we're two years around but but we're we're early but what What I didn't realize at the time is that how a lot of the underpinnings of AI were actually developed here in Canada.

45:40So deep learning was invented in Toronto by a guy named Dr. Jeffrey Hinton and a student at Yoshibengio, as in the guy, Yann LeCun, who's in New York now. But out west here, there's a gentleman by the name of Dr. Richard Sutton. He literally wrote one of the first textbooks on reinforcement learning. um so like to give you an idea like it's call it a top 10 top 20 school depending how you measure it on the planet for at least the academic side of ai and so there's a very small tech ecosystem here though and so we have all these all these people coming from around the world coming to study under these profs getting their master's or phd and i looked at this i said this might be the best place on the planet to actually there's a surplus of data scientists and machine learning engineers so it's a complete accident we just we were hiring for own business instead of hiring two engineers i heard four and then people kept hearing that i could do this ai thing and then all of a sudden we're like wait maybe there's a model there so cori on the personal side of things why did you keep working if financially you didn't have to was it this passion was it something else Yeah, good.

46:51Because I probably skipped over it. So as I really thought about it, because I didn't know myself, I didn't know what I wanted to do. I mean, that's sort of the unhappiness in the first couple of years. And I thought, okay, I want to be an investor, right? And it was okay. But what I miss is building stuff, right? And that might make sense in my mind anyway, right? Of like, you know, because I really don't have to justify it to anybody else, to be honest, right? But it's like in going through of like, what do I like doing? I like creating teams. I like going from zero to one. I like that early stage for my idea and building out something.

47:34And can that become a business? And I love talking with, you know, technical teams and being able to actually like translate between the business side and where there's an opportunity that like I love building. I love building businesses. And once I learned that, then all of a sudden I'm like, you know what, I think I can build a business model around that. and and it just so happens on the backdrop of ai i thought like that there's a good and again park the the rationale for it but like it really is was around a matter of like finding my purpose you know not having that when we sold always just saying add another zero because i wasn't gonna be like okay i'm just gonna add another zero or two and like that's what i want to do like that's i kind of thought initially that what it was and i'm just gonna just gonna invest and it's certainly easier to sit there in front of a Bloomberg terminal and just read all day but I just I wasn't happy so you're basically saying that you were not getting much joy out of let's call it passive investment investing even though it's never passive but but sort of not not creating value great exactly wanted to build and create value again well and yeah like it's building stuff is fun, but it actually took me two, three, four years to figure out.

48:55Yeah, no, absolutely. And even thinking back, I'm like, why did it take me so long to figure out like, duh, right? Like, I don't know what he would like, you know what I mean? And I think that's where, that's where this podcast and groups like Tiger 21 or YPO are so important where now Now that it's not like the early 2000s where we've got all these groups online, we have an ability to connect with people around the world. I think I could have fast tracked that if I had those right conversations before I sold, after I sold, the whole way through. Absolutely. Right? Definitely. You just need to take the time.

49:34It's almost like, I don't know, it's self-discovery or maybe just weak on that side of like knowing who you are, right? Like at that point. Yeah, but it doesn't have to take that long, right? If you ask yourself right questions, you can get there much faster. But how do we know what questions to ask? When I had my first exit, exactly the same situation. There was nobody around, no peer organization that focused on it. Now we are in a much, much luckier position to make these decisions. Did you feel embarrassed or ashamed that you didn't know after the first one? Of course I did. But now that it took me, I'm sort of embarrassed that like even talking about it, like I'm, I just feel a bit here.

50:22Like I almost feel like I think that's one of the reasons it took me a long period of time is because I didn't, I felt embarrassed to talk about it. Yeah. I think normalizing the problem is one of the most important things to do early. And this is exactly why it's so important that we hear stories from other people saying, oh, I have no idea what to do. I remember that for a while I actually blamed myself. I was beating myself up for, you know, being confused and not knowing what to do. Yeah. Which is just so unfair. And if somebody just told me it's perfectly normal, I think I would have saved a lot of time and effort and energy.

51:00Yeah. Yeah, exactly. Absolutely. One, yeah. And one conversation could save you a couple of years. Just, I like how you phrase that of like knowing even what questions to ask. knowing like and listen once you've sold okay you've sold great right but then you know knowing do you want to do board work do you want to get back in the game do you want to just invest like there's no right answer but if you had that framework to ask you those questions before sale post sale and that connectivity with the others that are there i don't think it needs to be a long period of time at all i yeah i think no yeah no one can tell us what we individuals individually really should do.

51:40I think people may have very different desires, situations. But the questions to ask are actually exactly the same. We may answer them differently. And another thing I noticed that there's so much hubris, there's so much pride and overconfidence that sometimes we just don't think that what others are going through would apply to us. And we're just overconfident. Talking about romanticizing, we talked about how we romanticize working for an acquirer. But I also found that post-exit, most of us over-romanticize three things. One is retirement. And some of us just go so crazy into retirement and reject work, reject business.

52:29And that's another way how we waste so much time because we reject something that we should actually explore. And then another thing, we romanticize professional investing. That's what you mentioned as well. I did that as well. We think that we can just become professional investors overnight and we'll be passive and our money will just grow automatically while we're having fun. And that's just a romantic idea. And then of course, another thing we romanticize is starting a new business because that also is not that easy. We need to start it at the right time for the right reasons and the right kind of business and for that we need to know ourselves quite well yeah so you would you agree i totally agree and the first two i think are a hundred and a hundred percent i would say my comments or my experience on the third one the first business i started i sorted it off the side of my desk saying hey i'll take my capital and knowledge of technology and allow that to scale it.

53:35And again, we made money on it, but it didn't scale. The difference now, I remember back in the early days of Investopedia, Wags and I would work all day. We'd be going back and forth between classes, frankly, and back to it. And then we would drive home and we'd write terms all night And we'd be, you know, chatting with each other on, back then it was probably like AOL instant message or I don't know, something like that. Right. But like we would, we would go back and, you know, you'd, you'd have a Ryan Coke and, and just bang out more terms or I'd send off cold call emails. Like I, like all we did was our life.

54:14I mean, we both had girlfriends, you know, that turned into wives after a while, but we, we, we literally just worked. I don't know. Like it didn't feel like you're working 80 hours a week because that's what we love doing. Well, when you're starting a company in your 30s or 40s, and you've got capital, well, you've got a different level of lifestyle, you've got a different burn rate, you've got, you know, often a family, all these other things that tie into it, that make it a lot more difficult to go and go all in. And I, I mean, with what I'm doing right now, I mean, I think there is a debate.

54:50Some days you wake up, you're like, why did I go back to the 60 or 70 hour weeks? Right. And, and like, I love doing it. That's the thing. I absolutely love doing it. But then, you know, you, you know, there, there is this beforehand, you had no options. You had to do it because there was nothing there. Right. And so the solution was, or failure was not even an option. Now, what I've done a bunch of times when I've gone in, because I've said like, I want prioritize my time and then I put capital to replace my time for me that hasn't worked if anybody can figure that out I'll give them I'll pay them a million bucks right like I have I have not been able to necessarily scale that right like I'm still I'm still going like I'm an entrepreneur I'm a builder right and I'm trying to build the right systems around me and so now what I'm having fun doing is building that scalable system but it still needs to be me in the flow I I've now come to grips with, I like being operational and I need to do that to succeed, at least at this stage, for where my next company is.

55:54So Corey, your kids are now 17 and 15, so you're quite an experienced parent. Any parent experience, but yeah. You also mentioned that your girl was born basically at the same time when you exited. Exactly. April 1st and we closed on April 12th. Amazing. So your story of an existed founder is as long as your story of a father, which is just fascinating for me. How did you reconcile and combine these things? Oh, man.

56:33We did have the flexibility as the kids were born to take some time off. I found that, you know, I was home for, I don't know, I want to say six, nine, 12 months. My wife might say three to six months. Like, I feel like the great things we had, the flexibility to travel more, to be that, like, I didn't go back to work right away on that. And so I feel like, especially when the kids were younger, we had a lot of flexibility there. And as I look back at all the trips we had and, you know, it was nice to be able to go because you don't have a day job. You know, we would go in in March and hang out in Palm Springs and beer on the pool.

57:18And again, as a Canadian living in the frozen, you know, north. Right. Like there's things like that that we did that I think gave us a lot of flexibility. um and then you know frank came to sports and being able to do that right so i think that it allowed us when the kids were younger to be really really present many exited founders find their purpose in children at first before they move on and find purpose somewhere else did you feel that probably not for myself to be honest but i think for my for my wife i think yes right and again there was also the dilemma and and what i think is actually a very a hard problem that actually very few people acknowledge in terms of like you know your partner there and and and the difference in terms of the freedom to make those decisions and the and the and the difficulty around that um but yeah for myself probably i mean you want to be a good dad um but i i mean And I guess part of me wishes maybe it's like, oh, you're just, you know, everything was just like that.

58:24But that's just not, there's this balance between wanting to be a great dad and doing that versus dedicating your life around that. That just didn't come, right? I mean, maybe I feel a little bit guilty about that for not feeling that way. But to be honest, it just, that's not how I'm built. You know, I'm actually very happy to hear that you did it that way because I see so many stories when exited founders feel so guilty that they hadn't spent enough time with their kids before. And obviously, you didn't have the kid while building a business, so you were lucky in this sense. But there's so much guilt accumulated, then they make the decision to go into full-time parenting, which is great for some time.

59:07But if you get stuck in it for too long, then you are in that situation when, you know, you no longer are fit for your next business or you're confused. And it becomes much, much more difficult. And then you settle into this parenting, full-time parenting situation. But I also noticed that for most people who go into full-time parenting after selling a business, they only really last for about a year of genuinely loving it. And then they want to move on and do something else on top of it. But sometimes they get stuck. So I think you were extremely lucky that you didn't have that burden of guilt from being a non-present father when you were building a business.

59:53Yeah. Well, but, you know, now again, so I've been at this current one for six years. We have, I work with my partner as well. So I would say that as, as the kids have been in their teenage years, that if, if you asked my, especially my daughter, she would tell you that we work way too much and we're never around. We're always traveling. Right. And so, you know, there's this, so I do have some guilt over that now we're doing. But there's some guilt. We were as present as you can get for the first 10, 12 years of your life. And then, yeah, we started this other business. And so you try to balance that off.

1:00:35And so sometimes with travel schedules and that. So the guilt came maybe the second company around on that. But I don't know. I'll be interested in talking to my kids. But aren't you an amazing role model, though? Because you show them a life of somebody who cares a lot about contributing. And it doesn't matter how much we tell the kids about it. Unless they show their parents living this kind of life, they will not have a model. In my heart of heart, I hope that's the case. I believe that'll be the case. I think involvement in the community, the philanthropic side, and then the business of trying to build something meaningful i'm i'm hoping that when my kids or adults will have a conversation around that and and i listen like teenagers are tough right and so teenagers are are at the best of times mad at everything and and and uh and so you know there's certainly there's certainly a guilt even even though you know that there's certainly a piece of going and this kind of gets back to the the core idea well should we just have not started our next business like you know because it's interesting because like we've talked you know my whole purpose has been around being able to build and start something again and and again not not tying your your identity to the company but tying it to the building and like that like being able to achieve something meaningful and at some point you're like you're doing that versus is, you know, you, I could just stay at home and, and be, not just stay at home.

1:02:22I don't want to say it that way. Staying at home is, can be the most important thing in the world for what I'm saying is I could not work and just be picking the kids home up from school. And then there's not, you know, the entire time and being there, you could do that. I, I, I wouldn't be happy with that. So I, I think I'm doing the best job I can at being a dad. I think I've been a great dad. I think I've been there. I'm not sure your teenagers need you. I'm not sure your teenagers need you 24 seven. They probably want their friends more than you. And then there's that too, right? And I think back to like, hey, I'm around way more than my parents.

1:02:55But like, you know, growing up in the 80s, like, hard to think of like, you know, how we were raised and, and hey, you know what, head out in the street and it's like, you go play street hockey and ride your bikes around and like, we'll see you for supper time and disappear for six hours. Right. Like, like we do so much more than back then. Right. but versus what society is saying or what so many other parents are on right now like they're yeah um you know like never mind like salesman like never around right like so so there's an interesting parallel there and like your purpose versus kids and again the strain of freedom the freedom to make the right decisions and then how that then manifest itself when you're trying to balance those things yeah true corey this leads us to the hottest question in our take tiger 21 community which is how to raise kids with wealth what approach did you take um how to avoid them being entitled lazy so we um are i mean unless my kids watch this something they don't know any of the details and uh the one thing that's come up um just as an as an aside with our house like friends will come over and it became pretty clear in in elementary in primary school when people come over said you have a mansion right and so the kids didn't know any different up to that point like like i drive a honda accord right we've taken nice vacations but with like that they don't there's not a whole lot of ways they can see it and so um we've um we're very much taking the approach of keeping thing i mean they know we've sold the company they know that they know clearly from our house that we're not poor but it's very much taken the approach of saying hey we'll get them their education and we'll support in that way but trying to but i mean the plan is really to have them on their own like they're gonna have to work they're gonna have to do the things they have to create their own life and you know if if even even if if we both got hit by a bus the estate plan they won't get a dime until they're way into their adult ages so that they don't, so that they can, we want them to have all the opportunity in the world and, but be able to pursue and figure out who they are without being impacted by this.

1:05:29And so I think a lot of people have that idea, but how we've actually implemented it is just to try to keep it as separate out. Like we don't, we're not looking for them to work in the business. We're not looking to work in a family office. It's go do what you're going to do. And it's not just find your passion. It's figure out what you can do. That's meaningful. Figure out what you can do where you can actually earn a living and contribute to society and be happy. So are you inspiring them intentionally to become entrepreneurs?

1:06:01To my dismay, I think the hours we work might actually be doing the exact opposite. I wish I could, but it pains me. Like my daughter said, she'll never start a company because she sees how hard her parents work. Right. And so we'll see, again, it's teenage years. We'll see what happens over time. Right. And so I, again, we're getting some dicey topics here. Right. But like, I don't know that I'd want, I kind of do think of being an entrepreneur as a disease. Right. Like, you know, certainly people can nudge you along to it, but once you get into it, you can never go back. And I don't want to unfairly push someone into it who is not in their blood.

1:06:49I mean, it should be in their blood. You know what I'm saying? Yeah, it kind of should be. It should be, right? Corey, I wonder, are you doing enough to show them how fulfilling that hard work is? Oh, no, that's a good question.

1:07:12um i'll have to ruminate on that one the fact that i can't say yes probably gives you your answer sorry for putting you on the spot like this but it was just a logical it was a logical question but these are the most interesting questions these are the most difficult questions right so again i'm from i'm from a small town in the middle of nowhere i've always said that i want I want my kids to be comfortable. We don't have a family farm anymore, but like, you know, out riding horses and, and, and in rural Alberta as in New York or London. Now our kids don't go to private school. Our kids don't go to that.

1:07:53And frankly, as they've been exposed to some of the stuff, like, especially through YPO, it actually hasn't been super good because we've, you know, like our kids go to public school they they they don't have like fancy cars they don't have all those other things and so even tying into sort of second and third generation wealth and exposures that frankly they get ostracized a little bit and so it's interesting trying to strike that balance being sort of like just i don't want to just say middle class like just being sticking to your roots but then also being able to be comfortable anywhere to me that's success right and so we've spent a lot of time trying to less on the entrepreneurial side but more about trying to like being confident anywhere right because like it's one thing if you grow up in manhattan right and you're always there and you're always in that circle right but when you you when you've grown up in and you know in smaller you know in the middle of of the country right it's different i don't No, I think it's quite hard to raise kids in big cities, too, for different reasons.

1:08:55There are all these confusing messages. Oh, totally. People in big cities tend to say, oh, it would be so much easier to raise kids somewhere in Canada in the middle of nowhere. Well, and so I do think it's easier to be there. But I also want to have them to be successful so that when we go to New York, that you're not just, you know. It's this balancing act. It's wanting both, right? It's wanting those kind of like the authentic roots with the ability to have a global mindset. Right. And so finding that balance there, that's been a tricky parenting exercise. Yeah. Okay. So what's your mindset today comparing to when you sold the business with respect to operations and systems and all of it?

1:09:38How would you summarize that? Oh, I think way, way more, like in terms of like the operational side of the business, I mean, just way more sophisticated in terms of like actually having a value-based organization that's driven by impact. Like success now, yeah, I want to make a lot of money. I want to build a billion-dollar software company. But what would be really successful is being part of a team that used AI to cure cancer. or building applications that have, you know, a material impact on energy transition and climate change. And so, you know, we talk like applying AI to elevate human potential is our purpose.

1:10:26So it's building tools that help people make better decisions and applications that we think are going to change industry. So like we would have I would have never thought about that in my 20s. So I think from a high level, there's that. I think there's a different level of, I know I'm an amazing CEO for the first 50 people. I know now that I'm not necessarily from 50 to 250, I've got work to do. And so I need to find the right mentors and people around it. Like I know my areas that I need to improve on, I think, right? So I heard some really important things here, Corey, which I want to make sure we emphasize.

1:11:02So it sounds like you have this rare balance between being aware that you want to continue achieving and create more wealth on the financial side of things. And yet you are primarily driven by the desire to contribute, to contribute the best you can based on all your experience and understanding of the world. Is that the correct description? build something right like yeah you know to so yeah so you basically want to want to keep working right you don't want to retire and not do anything and just see your your account grow which is where so many people get stuck but i love i love working i love the challenge i love i love bringing together teams and and finding new ideas and and probably the biggest positive plus energy things.

1:11:57I love talking with other entrepreneurs who have ideas, right? And like, can I help her succeed in this business? Can I help him in terms of capital? Can I, right? And so like that, that gets me going. It just took me like a decade to figure it out, right? So Corey, I'm loving this so much and I'm getting so inspired. And I wonder if you can help a category of exited founders that get stuck in that retirement situation. And I have, I know you're listening to my podcast, so you probably heard guests who were incredible exited founders. They built these fantastic companies. And I talked to them like 10, 13, 15 years after their exit.

1:12:40And they've been in this retirement all this time. And they tell me how great their lifestyle is. but then when I ask them, okay, do you have a sense of purpose? They don't. And they say, oh, not one day I know I will build another company. And what worries me in this situation is that would they still feel fit in business sense, like entrepreneurially fit, right? Because then it's very hard. You have all these habits around your lifestyle, right? you've relaxed and you're not entrepreneurially fit anymore right but yet they really really want to build something again so what would you what would you tell these people because you obviously you avoided this trap successfully well but it i mean usually i would go into d like because again when i sold and then a couple years to earn out and then i was investing and then dabbled with it I would say the biggest thing I learned is that going halfway in didn't work for me.

1:13:48And so I think it's probably a mistake to get right back in the game, like in six or 12 or 18 months. It's like, hey, take some time. And hey, for a couple of years, our kids were young and we traveled over 100 days a year. And like I there's lots of amazing things there. um i everybody's different and some people being completely passive and working on that and say hey maybe you want to do more philanthropic goals i i i think that that you could have purpose in philanthropy in a big big way for sure yeah if your purpose is building and if you do want to get back in the game being able to to to acknowledge your current situation and and like that it's just because I thought doing it the next time around would be easier.

1:14:40Building a company is always freaking hard. It's always hard, right? Exactly my conclusion too. It's always your entire life, right? And so I guess I made, you know, as I'm talking to it, I made two mistakes. I went half in trying to thought that I could almost mentor back and forth and replace my entrepreneurial grit, if you want to call it, I guess, but like with, with capital that has not worked for me. That's made bad investments and, and, and being a good partner versus a good investor are different things. Um, and, and then, yes. So then, and then understanding that it, it is just thinking that because you've had one exit, like, yeah, you've always learning is you can scale it up first to this, that things you could do better, but there is a natural growth of businesses and you can't just fast track the entire process at all.

1:15:34And it still is all encompassing. Right. And, and, and how do you build a situation with now with kids and different things around that to acknowledge that like, you can't be that same 22 year old. So that's, that's where I let down. So I, you know, I, and listen, if someone's listening here, I'm more than happy to have a conversation, just ping me on LinkedIn on this or anything other topic. I think the whole lifestyle versus work or contentment versus purpose, it's such an important dilemma. I actually published an article recently about that. I call it the exited founder's dilemma because it's so common.

1:16:14And just based on all the stories I've heard so far, I came to the conclusion that the best approach to this is to focus on contentment first, focus on lifestyle, on recovery, on your health, but for a period of time while figuring out answers to questions. But then if you do decide to have a business and really have this sense of purpose, it's not very helpful to wait for too long because then it gets harder. It's this balance. You can't start a business too early before you answered very important questions and before you rested properly but also it's very hard to do it too late like timing is so critical that resonates that resonates with me big time and i've seen that people like i i i can think of half a dozen examples like that that waited too long and now you see this with people retire whether it's sort of parents or grandparents or you know you know kind of just forget not not just entrepreneurs when people retire all of a sudden And they're so busy, right?

1:17:18You know, they go to New Mexico or wherever, and they, you know, or they go to somewhere in the Caribbean. It's like, they're so busy. Well, what did you do? It's like, oh, well, I had my workout. And then, you know, met for lunch. And then, oh, my goodness. And then, like, you know, I had a doctor's appointment. And that was two hours. And you're like, you did all that stuff when you're raising a family and running a business. And so even entrepreneurs, once they've gone, you fall into that trap. And so I think you're right. That really, really resonates. It's the Goldilocks. It's like that right away is too quick.

1:17:55But then there's almost an expiry date where then you're out of your network, out of your connections. and and and then you develop self-doubt right then you're not even sure you can do it and then there is more there is more to overcome if you if you try to do it later but another another thing i found is that um we only get a sense of purpose when we work when we sacrifice when we accept a duty we don't get a sense of purpose from just pleasing ourselves like like if we are stuck in self-indulgence it's not going to give us a sense of purpose so whether it's building a business or whatever it is it will have to be work and yeah and i think if if people don't have a clarity of on what actually gives us a sense of purpose early on we are looking for a wrong thing or we just ignore that in our romantic ideas about how wonderful it would be for us to just enjoy life all day long and i think the advantage that you have the second or third time around is that you can choose something that your work is tied to the impact that you want to have exactly this this sense of contribution yeah it's what you were talking it's so important to understand what it is i'm actually contributing to this world right there is a point in our life when when it when becomes very important because I think humans, you know, early on, we're just learning to survive.

1:19:29But once we've learned to survive, once we've learned how we've learned the skill of securing resources, we naturally want to contribute to give something. And if we're not given, then it becomes a very unhappy existence. Yeah, totally. And you can almost through the Elon Musk, Bill Gates comparison there of, of, of Musk saying, I'm making more of a difference through my companies for climate change, interplanetary, yada, yada, yada versus Gates and the foundation. And neither is right or wrong, but like, I think it gets there. Um, it, it, it, it, it really is the thing though, that I, if I can build on your, on your, on your last comment there's almost this like safety i think what you know how much can you ever be really safe and so there's this debate of like okay if you put x million away and just have that in treasuries or have that in cash and we know we'll never have to work over again i'm gonna do it but i always find that like all the amazing you almost always go on all in and in some ways like entrepreneurship is like a disease, right?

1:20:43Like you're always like, well, I've always got a backup and I can go higher and I can always, and you could always put in more capital and we've done that. Like, you know, and, and so is there a way to have that balance? I think that's something that I'm still striving and trying to find. Like you would, you know, you want to make sure that your kids are okay in your state and you've got a lot done, you know, and it's easy on, in theory, but I'm curious, like your thoughts on that one afterwards, like Like, you know, is it even possible to say I'm going to take X amount, put it away. And this is my thing here, because what happens if you go through and you and you go through all that and something's not going well, you're always going to go back to like all the resources you have.

1:21:23Right. Or I don't know. I mean, have you do you see what I'm saying? Like the safety in that side of it versus like almost having a free role in the next business, whereas when you're first starting out, everything's on the line. So you're totally in. Whereas, you know, is it ever possible to not be completely in? You know, I actually found that creating financial stability and some sense of safety is extremely helpful for the next business. And that realization, unfortunately, came to me a bit too late because I was very much into this. I'll go all in in my first attempts to create sequels after the first exit.

1:22:02But later I realized that if we actually have sufficient sense of safety, and that's a very personal feeling, we need to figure out what sufficient means for us. But if we have that sufficient safety kind of put aside somewhere, we stop worrying about finances. A lot of energy and motivation gets released. And then we focus so much more on our contribution because we feel safe. Like if you think about, you know, the Maslow pyramid, we have the financial safety rate right at the bottom. And if we are worried about it all the time, then our focus is there, our motivation is there, our energy is there.

1:22:38And once we have this sufficient satisfaction on that level, we naturally want to do other things. Yeah. So I personally came to the conclusion that if early on we actually take some boring but necessary actions to have that stability and to decide what part of our exit wealth we want to play with and what part of our exit wealth we devote to stability, it's very helpful. Yeah, that resonates. I think that is something to strive for, that mental model. um i it it makes me think of um something branson has said and i'm not friends with richard branson or anything like that we were on necker island once and so we had some time uh we could hear his experiences and you know he talked about on his way to becoming a billionaire you know mortgaging his house two or three or four times right like he was like this like consistent you know and so you and so you see these stories of of being on the edge right and And then when you're on the edge and you're having the discipline of like, OK, I'm putting this in my safe pile, but then always having to go in more, always trying to come into that.

1:23:47And I mean, like like even like Tesla four years ago is one month or whatever, one month from bankruptcy. And now it's a trillion dollar company. Right. And it's all these stories of like being like all all in all the time. And so it'd be nice to not have to be all in. And I think your way is something that is like a mental model that all exit founders should think about in terms of like, how do I get to that? because can that unlock more of me not having that unnecessary stress maybe? I think this kind of masochistic approach, financial masochism, often comes from the idea that if we're not hungry financially, we will not have motivation.

1:24:24And for some people, it's subconscious. For other people, they realize it and they say, as an entrepreneur, I have to always be dissatisfied. And we risk our money to put ourselves in this situation of being dissatisfied because we're so scared of being satisfied, it feels like death. If I'm satisfied, I'm no longer motivated. What I found is that it's actually based on ignorance of the fact that our motivations over time naturally change. And while fears and greed are great motivations for the first business, there are motivations of duty and love that are much more appropriate for our later ventures.

1:25:06And it's perfectly okay to be satisfied in terms of greed and even personal fears. It's perfectly fine to be beautifully content and then still be very, very driven to do work because we love it, because we feel it's our duty to contribute to the world with whatever it is we know. And out of genuine care for other people, our employees, our customers, whomever we can influence. And I think the lack of understanding of those higher motivations actually keeps people trapped. Like I like to ask my guests on the podcast about how they interpret Steve Jobs' famous phrase, stay hungry, stay foolish.

1:25:51And what I find is that many people interpret that as financial hunger. But if you look at Steve's own life, even superficially, it's very obvious that he was never motivated by money. He could never possibly have said that phrase, meaning money. What he meant is that hunger to do what you are meant to do. In his case, it was creating beautiful and useful products for people, right? In your case, it may be using AI to elevate humanity. yeah but that's a different type of motivation it's actually much more powerful but to fully embrace that motivation it's actually very helpful to be financially secure to feel financially secure like like for me for example you know my mission is is helping these amazing people who created so much value to get unstuck and actually keep creating value keep making our society better And I feel if I'm, if I'm contributing to this, this is so important.

1:26:53This is what makes me, you know, get up in the morning and work. And I'm so lucky, so grateful that I don't need to do it for money, because it wouldn't be the same thing. you you that is a really really interesting train of thought i i'm gonna you know and i'm gonna have to think about that process that for a while because i as you say that i'm like i have 100 done that myself it's almost like that that financial math or mess financial masochist right Right. But I'm curious, maybe maybe a related concept. Because people talk about when is enough for business, but like when can you be or when, you know, when is enough for from a financial perspective?

1:27:40But when is enough for what you've accomplished, what you've built? Right. And how do you strike that? Is it creating that balance with staying hungry and having that sort of that edge, but then also being satisfied with what you've built? Like I find this, I mean, we're taping this in December. I always found a hard time at the end of the year because I'm always unhappy about how much I've accomplished out the year. even if sometimes you look back at it and rationally, you know that, okay, I've actually done a lot of really great things. You know, it's like, you know, it's almost like, well, do you need that edge?

1:28:19Like that edge cause, well, that, that sort of angst, it causes angstness anxiety versus in the same way that you're talking about on the financial side, if you can have that, can you open it up by just being satisfied and being present of those learnings and then building on that? See what I'm saying there? Like it's, I find that's been one of the hardest things about the next time around, right? It's like, I should be doing more faster. No, absolutely, Corey. But I also wonder if you can reframe this into thinking, oh my God, there's so much more I can do and be inspired by that. Because that's essentially what it is.

1:28:57You feel you haven't done enough because actually you just see how much you still can do. And that's a very different angle. which may be more inspiring, more energizing. Yeah. It's almost like you've thought about this a little bit. I'm a big mental models fan, right? And so I'm always trying to, like Charlie Munger talks about your latticework of mental models. And, you know, you can have having that success at a young age, like at 27, I think builds almost this hubris and whatever of saying like, okay, I maybe there's a little bit of luck on timing, some good hard work on that. Maybe there's, you know, there's definitely some, you know, great things we did on, on that.

1:29:42But then I think being more humble in terms of where you've got weaknesses or where you've got areas that need to be going on and being able to, you know, we all understand the concept of growth mindsets, right? But it's not like a, it's not like you're always just in a growth mindset. it's really easy to get emotions involved and then fall back into these other areas right and so thinking of this as it's no longer just like that I'm on one path as an entrepreneur but at every different stage it's like reinventing and reinventing and reinventing and as you hit those inflection points being open to talking to the right people or learning from others and leaving that hubris behind leaving that and just saying at this stage how do I surround myself with the right people to know what that next stage is right so thinking of it as more of like that journey um you know if if i could go back to my 27 and 28 year old self and and convince him of that that would have been amazing and so hopefully hopefully even talking about some of it the mindset and these things of it like you know versus just dismissing them right um hopefully there's hopefully there's one nugget that someone can take or there's something of that there's an experience to go like, wait a minute.

1:30:58Right. And then, and then to what you said beforehand, being able to do that and having those conversations and those relationships to be able to then ask the right questions of yourself, that that's it. That, that to me is like, is what I wish I knew faster, but Hey, know that now. And I still got, you know, at least 30 years and hopefully with all the long, maybe we can invest in some longevity stuff and hopefully it's longer that then you can do more you know more stuff for longer and that and have more fun right and and and build more relationships with amazing people around because like there's never like now now is the best time to be building stuff like the the opportunity that's out there technology it's like the next decade's going to be amazing and so anyway i could ramble on about that but like there's that you asked a very difficult question so let me pause there versus at the risk of rambling on the bottom line is that uh if if only you knew what you know now earlier on say you know you sold your business and you knew that you know it's this new purpose it's this you know sense of contribution that should be pulling you forward because what what we're doing we are stuck in this selfishness for a very long time we're like oh how can i make my life even more comfortable how can i invest and get you know half percent more return we are so absorbed by things that are essentially very selfish and they never give us the sense of fulfillment and then early much later in 10 years 15 years we think oh my god if only i knew how beautiful it is to be pulled by something significantly less selfish but at the same time embrace some selfish needs, right?

1:32:47Embrace the need for self-care, embrace the desire to grow our wealth without guilt, right? If we knew how to create this balance, that's what I'm really trying to achieve. I'm trying to bring people like you and show your story to those who just exited to show them, look, you know, don't believe me, but look at Corey's story. Here's how the way that Corey fucked up. exactly this is how exactly don't do that but then look at where he is today and maybe you can get there faster if you learn from from his experience and ask yourself the right questions and if we can support each other and build those connections right like even 20 years ago we would have named i mean well never mind that podcasts weren't a thing right but like yeah you'd go to conferences here and there you'd meet someone but now the connectivity or like like you know and and again groups like ypr tiger or whatever right like you go you know that entrepreneur who just sold in india who's moving to dubai and that that will be like what's to me what's inspiring is like hearing stories of what other people are doing and then going oh man oh look at how much more is out there look at this and it's always that that that positive energy conversation that additional piece of it that that like that that that makes you ask another question or or see something in a different way right like that's what's so exciting now right that's what's exciting right now about about being able to build and invest and and and uh um but it's just about conversations and and trying to be trying to be open and again get rid of the the hubris and the closed-mindedness of my 27-year-old self and and and just even on this one like you know I don't I've been on a lot of podcasts I've not really had a question that's been like so that I've not really how do you actually answer that so whenever you have that question it's like okay that's something I need to think about but I also think that lots of people underestimate how important it is to be intentional about the skills that we need to learn early on and one of the skill I think is so important is this skill of creating inspiration deliberately whether it's by talking to other people or to be to exposing ourselves to what's really inspiring and important in this world like I can see for example that you're so inspired by what's happening in AI and I can see it gives you energy and you are feeling oh it's now is the best time to create because look at all this exciting stuff right but imagine if you didn't know that if you didn't put yourself in in in this information field where you get the inspiration and i think this is just so important intent being intentional about inspiration that that's a good yeah yeah how many people actually do that i think you know inspiration we've isn't it natural just think of inspiration as like something randomly that happens right but you know to seek that out i i like that yeah but but if you if if you expect it to happen randomly you can you have no control over it right you just you just sit there waiting for random things to happen to you and this is how we waste a lot of time and energy totally totally well and and and i mean i think there's also some dynamics are like when you talk about the skills around this i mean there's also and to be not to completely stereotype but i think most most guys most men would probably have more of an issue with that because it's you know you've got to you've got to be vulnerable and open up and talk about the areas you're bad and then and then even acknowledging that like hey even though you're really successful in this one area there's all these other soft skills there that maybe you're not so strong at right you know and i mean again that's where some of that sometimes the peer-to-peer groups come in but you know it you know there's there's no there's no course there's no like roadmap right like a lot of it is that's i think that's and maybe that's more what you're building out but it's it the tricky part is being able to actually build out that you know those frameworks and you know the question i definitely want to to create more of that i think it's extremely important that's it's not just communication skills but it's also the way we feel inside it's this non-transactional mindset with respect to other people um and that we we need to and sort of this this ego that that prevents us from from opening up because we think everybody wants to see us as heroes you know sometimes i approach a person and i want to interview them and they're like oh no no wait wait wait i i want to first make sure that my new business is success and if it's success I'll come to your show and I'm like no no no I want to talk to you now because you're struggling well Anastasia that's what I find interesting I said that to you because I mean some of the headlines of that I'm like oh no my exit wasn't as big as you know I didn't have a billion dollar exit you know you know I you know I listened to that person you know three shows ago I'm not as big as him right you know like so I mean I did that same thing to you and it's natural and it's natural but I think it's by overcoming this we can open up right that's a muscle we need to build and we do it a couple of times we see that actually people love us more when we are more vulnerable we get this positive feedback from the world and that that's when it becomes easy but it's the first step that's hard oh no you're right well i mean it it i will admit it is intimidating talking about all the all the things that you've messed up you know in a good situation right after an exit right and all the uh all the emotional stuff there it's uh you know emotions uh I'm told that emotions aren't exactly my strong, just strong, sweet.

1:38:43So, you know, I'll keep on doing stuff like this, like to work on it, right? Well, I think you're way above average in my book.

1:38:56Corey, thank you so much. I loved our conversation so much. I need to let you go because otherwise it will continue for hours. But I will ask you the last question, which is the same question I ask every single guest I have on this podcast. How do you want to be remembered?

1:39:14I want to, there's two elements. I want to change the culture and mindset of Canada and where I'm in Alberta in terms of to be more entrepreneurial driven and to embrace business. So that's more of a societal piece of it. And then, you know, if we're talking from a business perspective, I mean, I think the most important thing is that my kids over the long run respect me and have learned and have given them the opportunity. But, you know, if I could make a dent in cancer, if I could make a dent in a major disease, if we could actually bring together the problems in the healthcare system with data and AI.

1:40:03I'm on my deathbed. And, you know, cure is a big word, right? And so, you know, the goal is defined in my head, like I'll know it when I've accomplished it. But if I can bring together those different groups, bring together the health side, the AI side, and figure out how to kind of throw enough capital behind that, that would be success. Yeah. This is so beautiful. Thank you so much, Corey. This has been so much fun. Positive energy conversation for sure. We'll have to do it again. Plus two. Plus two.