Cory Janssen. 17 Years Post-Exit: Insights from Investopedia’s Founder
Episode - 47
Cory Janssen. 17 Years Post-Exit: Insights from Investopedia’s Founder
My guest today is Cory Janssen, co-founder of Investopedia.
Cory sold the business 17 years ago, but what came next was far from the smooth ride he or anyone might have expected.
He spent years in painful trial and error, half-heartedly starting new ventures while avoiding real work, experimenting with professional investing and retirement.
None of it satisfied his deeper need for the sense of purpose he felt while building Investopedia. Everything changed when Cory went back to building and working.
But this time it felt different. His focus shifted toward unselfish, larger impact goals. His new non-monetary motivation gave him powerful drive and a clear sense of direction and alignment.
Today, Cory finally feels deeply fulfilled, energised and joyful. There is so much to learn from Cory's story and we are so lucky he agreed to share it openly. It's rare, raw and packed with specific practical insights for anyone navigating the complexities of post-exit life.
What We Discussed:
00:00:00 Introduction
00:01:40 Guest Introduction: Cory Janssen’s Story
00:04:00 Founding Investopedia: The Early Days
00:10:55 Deciding to Sell Investopedia
00:22:15 Regret After Selling: Financial and Emotional Impact
00:35:10 Working for the Acquirer: Lessons Learned
00:46:50 Negotiating the Sale Process: Tips for Founders
00:56:20 Post-Exit Struggles: Managing Wealth and Purpose
01:07:10 Challenges of Professional Investing
01:15:30 Rediscovering Passion for Building: Transitioning to AI
01:26:15 Balancing Parenthood and Entrepreneurship
01:37:30 Raising Kids with Wealth: Avoiding Entitlement
01:40:00 Closing Reflections and Key Takeaways
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Anastasia: [00:00:00 - 00:00:04]
Why did you keep working if financially you didn't have to?
Cory: [00:00:04 - 00:00:38]
Because I hadn't. I didn't know myself. I didn't know what I wanted to do. What I miss is building stuff. I like going from 0 to 1. I like that early stage from my idea and building out something and can that become a business. And 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 it just so happens on the backdrop of AI, I thought like there's a good and again park the rational. But like it really was a matter of like finding my purpose.
Anastasia: [00:00:40 - 00:01:56]
My guest today is Cory Jensen, co founder of Investopedia. Corey sold the business 17 years ago, but what came next was far from the smooth ride he or anyone might have expected. He spent years in painful trial and error, half heartedly starting new ventures while avoiding real work, experimenting with professional investing and retirement. None of it satisfied his deeper need for the sense of purpose he felt while building Investopedia. Everything changed when Corey went back to building and working, but this time it felt different. His focus shifted toward unselfish, larger impact goals. His new non monetary motivation gave him powerful drive and a clear sense of direction and alignment. Today, Cory finally feels deeply fulfilled, energized and joyful. There is so much to learn from Corey's story and we are so lucky he agreed to share it openly. It's rare, raw and packed with specific practical insights for anyone navigating the complexities of post exit life. Hello Corey.
Cory: [00:01:56 - 00:01:58]
How are you? Anastasia?
Anastasia: [00:01:58 - 00:02:46]
I'm very well. Corey. I am so excited about our conversation today because for me, you are such a unique guest. You've tried so many things that many people in my audience are only thinking about. You've made a lot of mistakes. You romanticized things that many of us are still romanticizing and you learned the hard way why certain things should not be romanticized. And I want us to go very deep into those traps because you and I both know that sometimes we get stuck in those traps for years and that's exactly what we're trying to avoid. And that's my mission with this podcast. To help people not get trapped in those things and move through the post exit journey as smoothly and efficiently as possible.
Cory: [00:02:47 - 00:03:00]
Totally. And you know I've been looking forward to this. It's like you've become the Joe Rogan of exited founders. Right? So no one goes as deep. So I'm looking forward to sharing the good and the bad and the Stuff that people don't talk about.
Anastasia: [00:03:01 - 00:03:47]
Well, thank you so much. Flattery will get you everywhere. Right. So Corey, to kick things off, I want us to talk about Investopedia, the company that you sold 17 years ago. Oh, you're dating me now, but I personally owe you a great debt of gratitude for creating that company. After my own exit, I found myself drowning in conflicting and biased investment advice and Investopedia became my anchor, trusted voice of reason that I could actually rely on. So thank you for that.
Cory: [00:03:49 - 00:04:05]
People have either never heard of it or they come up and they say, like, I would have never gotten through my MBA or my CFA without you. Right. So it's kind of an interesting thing where it's that niche product that was there that if you've been in finance, you know, especially that generation, you know, so I appreciate that.
Anastasia: [00:04:05 - 00:04:42]
No, it's absolutely fantastic product. And you know, the first time we met, I immediately told you that I'm so excited about Investopedia and love it so much. And even today it's still the one source that I fully trust and get educated from. Another reason I want us to focus on that company first is because, as you know, this podcast is about how founders feel post exit and we talk about emotional, intellectual, social, financial challenges, but so many of them are deeply rooted in what happened before an exit.
Cory: [00:04:42 - 00:04:43]
Yeah.
Anastasia: [00:04:44 - 00:04:50]
So your turn now. Tell me about Investopedia, why you started it and why you sold it.
Cory: [00:04:52 - 00:06:55]
So we started. So I actually started Investopedia with a friend of mine, also named Corey, his name is Corey Wagner in the late 90s. So technically we started working on it in 99, formally incorporated in February of 2000. And for those who are good at stock market trivia, the peak of the NASDAQ for the dot com bubble was in March of 2000. So we literally were like right at the end of the first dot com bubble and I was actually still in university, I was a second year college kid. And I'd like to say we had some amazing plan, but essentially we would go and we'd be studying after class and at that point and this sort of, it's funny to think about now, but all these startups would raise money and then buy ads in Business 2.0 red herring, these big magazines. So these magazines would be thick with ads right from all these.com startups. And so, you know, what are a couple 19 year old kids gonna do? Like we gotta start a dot com. So we, we actually brainstormed a number of sites. I mean Invest PD was only one of them. But you know, essentially wrote out the biggest, baddest website we could think of. Sort of Yahoo Finance meets the Street.com meets the Motley Fool. And basically all the sites we loved said, can we create something better? As we actually got down to doing the work, we realized we probably didn't have the resources or the skill to do everything. So we just started off on the education section and we did that because we figured if you can write the content timeless in a timeless evergreen fashion, we could get to the rest of the fun stuff. It turned out that we actually kind of stumbled upon this, you know, this niche that, that no one else was really focusing on. And so it just became educational content and tools. But it was really by accident, to be completely honest.
Anastasia: [00:06:55 - 00:07:04]
Yeah, you were very early in this game because obviously now online education is booming. But back then it was such an unusual idea, wasn't it?
Cory: [00:07:04 - 00:08:36]
I mean, this is before MOOCs, before anything moved online. I mean, there's no Coursera, there's no. Yeah, I mean there was no, I mean YouTube was sold at, you know, I don't have to check the exact date, but like it, you know, this is before social. So like the Web 1.0, 2.0, it was a different world. Like, you know, I remember it was a huge day when we got listed on Yahoo, right? It wasn't the same search engine optimization game that it is today. And there, there wasn't the same mix. So often entrepreneurs will ask me about that sort of formula and they said, hey, things have changed so much. Like you can't use that same playbook. But it was really just about, you know, creating great content. And at first it was us writing, like we would just lock ourselves in a room and you know, while we were studying for our CFAs and going to school, we were just cranking out content and over time, you know, attracted a couple hundred contributors. You know, think like a small hedge fund manager, a cpa, you know, and we'd write really, really in depth content. But the world was actually changing because, you know, at that point people were still just hiring a bunch of journalists, sticking them in a room in Manhattan and launching websites. Like the whole idea of creating your own content, I mean, it sounds just obvious now, but that was kind of new, right? And so building the system from like, because we weren't journalists, so we didn't know what we were doing, that was actually our edge. We just tried to create stuff that we wanted to read.
Anastasia: [00:08:36 - 00:09:00]
But it's amazing how you went from there to where you are with AI and we'll talk about it later. I don't want us to jump all the way there yet, but I want this interview to show your whole, your whole path, how your thoughts developed from those very early days to today. But let's talk about how you decided to sell and why.
Cory: [00:09:00 - 00:12:32]
We initially, I mean, keep in mind this is know, early 20s, right? Like we were, we were hiring people out of our classes at. I live in Canada in University of Alberta. Like, I would go to my class and like there'd be, you know, people that would be working internships that like, were in that same class that were working for us. So our first goal is we just wanted to pay off our mortgage. And you know, I think at that point it was like, I don't know, a few hundred K, right? And so we're like, okay. Like we, and we had just, you know, okay, that's amazing, right? And then, well, how do you set the next goal? Well, we want to be millionaires, right? And you know, you'd kind of get through. Like, because we never raised capital, we actually had to just, you know, make money the old fashioned way. It was just. And, and Investopedia was a cash flow machine because you create the content once it's timeless, it's like an annuity. And so because we had costs that were low and you know, we were just a couple kids doing this and really just focus focused on, on, on literally month to month cash flow. You know, we get to the year and do kind of a bonus out. And so, you know, eventually a couple years later, we said, okay, well we want to, you know, we want to be worth a million bucks. And I remember at some point we passed that, we're like, okay, well now what's next? Okay, well, I don't know. I guess you add a zero, right? Like it was at that point, it's not really didn't have anything to do with values and purpose. I mean, that's just who, you know, we were just a bunch of immature kids. And so at some point though, you can only sell. Like our, our big clients were like E Trade and Charles Schwab Ameritrade. Like this was the first kind of the golden age of discount brokers. I mean, it's almost hard for younger listeners now to think about with Robinhood and all this stuff that is free. Like it was it. This was a big thing that you could trade stocks online, but you can only sell these brokers so much advertising per month. Before that, you actually have to show up in New York with A tie. Right. And, and absolutely, like, we hadn't, we hadn't met really any of our clients in the first few years. Like, we went to one conference in Vegas where there was sort of one ad network that we sold through and you know, we almost became like bigger than the rest of the ad network. Right. And so we, we had managed to. Because again, this is before video calls and all as well. Like, we were cold calling people to sell ads. Like, no one really knew that it was a couple of 20 something year olds from Canada that were doing this financial education site. And so at a certain point we realized, like we were getting so many inbound requests, we said, okay, well we're wasting all this time when all these brokers are calling and kindly dialing for dollars. And you can always tell when it's somebody on the other end just sort of filling you into their CRM, trying to get information on said, you know, let's. We either need to kind of like really figure out how to sell and build out a whole sales team across the US or we need to partner someone that knows what's going on there. So let's run a process. So we hired a banker from Silicon Valley. As a guy, he actually taught the negotiation class at Stanford, which you can come back for, and so decided to actually say, like, let's actually go with and do this formally because we're just wasting time on everything else. Right? Like every time people are calling now, I mean, I've got. Oh, and we could get into all the things of like, what we did wrong there and that, because I would never do that again. But it was like completely opportunistic. We weren't really thinking about that from like a real, you know, like again.
Anastasia: [00:12:32 - 00:12:45]
Keep in mind, actually, Corey, I would love that. Can we go through the things that you wouldn't do again? Like, what would you tell people who are about to exit, what to be aware of.
Cory: [00:12:45 - 00:13:02]
We did one good thing, which is as we went down the process, we, my partner and I, we both wrote down on a piece of paper how much we wanted to sell for and what we would do with that money after the fact.
Anastasia: [00:13:03 - 00:13:03]
Okay.
Cory: [00:13:03 - 00:13:33]
And it was funny. Like, it wasn't even. It had nothing to do with the value of the business. It was like, well, I think I need, you know, a couple million bucks for a house and I think I need, you know, you know, like this much for, you know, public equities and I might want to start another business. I want that. Like, it would. We both literally just kind of like did on literally, literally on a piece of paper we didn't show each other. And we put that in an envelope and we sealed it and we put it into the, into, into the debt. We still had, you know, paper then.
Anastasia: [00:13:34 - 00:13:35]
Cool.
Cory: [00:13:35 - 00:14:55]
Now that was really valuable because when we got really in the negotiation process, we were pissed off because, like, you know, there was an, There was a tax issue and it was going to cost us a few million bucks or whatever. And so then, you know, we were all angry, but there's so many emotions in a sales process. It was grounding because we went back and we looked that paper and said, wait a minute. Six months ago, we said we would have sold for this. We're already going to sell for more than this. Let's like, let's keep things in context. So that was actually a really good tip. And I think as you get through motions, I tell entrepreneurs that all the time, just writing down what your expectations are so you're grounded. That was good, but it wasn't based upon what I wanted to do in my life and purpose. And like, you know, we, like, if, if. I know for, for myself. If, if, if your, your goal in life is just another zero on wealth and it's not about creating something. I mean, there's something like, that doesn't work for me. It's just sort of doing it. Money's important. I want it for the money. Don't get me wrong. This. I'm, I'm a capitalist. But it's. We were so immature. We weren't really thinking about, like, what was next or why were we selling or what were we going to do with that. It was just, well, that's what entrepreneurs do. Right? Like, that's, that's how you win the game of founding a company. You sell.
Anastasia: [00:14:56 - 00:14:58]
Have you ever regretted selling?
Cory: [00:14:58 - 00:15:00]
Yeah, big time.
Anastasia: [00:15:00 - 00:15:01]
Yeah. Really?
Cory: [00:15:02 - 00:15:17]
The purchase price wasn't disclosed. It's never been online. And I agreed with my partners that we would never talk about it. And you know, so, like, it was. But we do know that it changed hands a few years later for a significant amount more. Right.
Anastasia: [00:15:17 - 00:15:18]
Okay.
Cory: [00:15:18 - 00:16:30]
We think even like, you know, 100 million more. Right. And so you kind of go, so there's now. And everyone says, okay, well, hindsight, you know, and that's true. But, but again, the. There, there, there. It wasn't just like when we were thinking about, like when you have a business that is throwing off significant cash and you're having fun doing it and you're building something meaningful and you're making a difference in people's. Lives. I don't think we realized how, like how good we had it because afterwards we'd go out and try to replicate that and it's like, wow, our business, man, our, our margins were pretty good, man. We threw off a lot of cash, right? So I couldn't replicate that with buying another business. We had a great team that like we, you know, it was, it was a relatively small team, like under 50 employees. But like, you know, we could have scaled it in a different way. And so there's the regret from the financial point of view. But then I think as I reflect back, I was more unhappy after I left than at any point in my life.
Anastasia: [00:16:31 - 00:16:32]
Why is that?
Cory: [00:16:33 - 00:18:12]
So we sold in 2007 and then the first year was okay and, but then there was a financial crisis. Right. And so even though we were actually doing okay, when, when there's pain at head office, then you need to feel pain as well. Right. In one of the subsidiaries. So I always remember Tim Forbes had flown up to Edmonton after the deal and you know, he came up in his private jet and oh, it's Tim Forbes. And, and I said, okay, you know, Mr. Forbes, okay, we got the deal done, now what? And he just turned to me and said, don't it up. He was awesome. Huge respect for, for him and the Forbes family. But you know, I was on my own. We were basically on the own. For the first years we had a two year holdback and so for the first year we just kept on doing the thing and it was still fun. I mean, you didn't have the equity upside, but you're, you know, you wanted to do good on it. But then, then like any organization, they start integrating in the acquisitions and then all of a sudden you're dealing with and all there's all these loops to get through and you're no longer in control of your own destiny. And so it got frustrating. So I, at that point, I remember driving to work one day and I love to get to my desk early in the morning. Like you're thinking, you're, you know, I've got like a 20, 25 minute commute. You're thinking about the day. It's almost like, I don't know, it's weird. It's almost like cathartic, like this meditation going through. Like I, I actually I, I, but I, I really, I realized for the first time when I was driving into work one day that I didn't want to go to work and I'd never felt like that in my life. So.
Anastasia: [00:18:12 - 00:18:20]
Yeah, so you didn't expect that. You, you thought your motivation will stay the same. Right? You probably didn't think much about it.
Cory: [00:18:20 - 00:18:39]
We just didn't think about it. And that's, I mean, you know, like, I mean to, to summarize up your previous question. I mean, the bottom line is we didn't, we didn't even know the questions to ask ourselves. We were just saying, okay, well you know, our goal was to get to a million, then the goal is get to 10 million. And, and so like that's what you do, right? Like so just, just.
Anastasia: [00:18:39 - 00:18:47]
Yeah, we focus so, so much on money and we think, you know, we're just selling something, like another object, whatever, a car.
Cory: [00:18:47 - 00:18:47]
Right.
Anastasia: [00:18:47 - 00:18:57]
But selling a company is so completely different and people completely underestimate how it hurts us emotionally.
Cory: [00:18:57 - 00:20:34]
It's your identity and you can work off that, you know, but it's also because we hadn't done the work on, really on. I hadn't done the work. I'll say I. Right, like that I hadn't done the work on understanding my purpose and what drives me. After we left then I was like, I was just sort of like grasping. I had no idea. Like I, I didn't know. Like you should be happy and you don't get any. Listen, this is, this is a high class problem, clearly, right. Like, you know, but even in groups, like I've been heavily involved in EO and YPO and, and these peer to peer groups and tiger 21 groups like that and, and I'm a huge, I'm a huge proponent of, of, of peer to peer learning. Right. And, and, and learning from others experiences. I mean just like, I mean there's a lot of that here in this podcast. Share from experience, learn from others experiences versus advice. But within my forum at the time, no one had sold and so you can't get that same level of understanding or empathy. Like there's nothing, you know, there weren't the communities online or, or other places to go to hear what people were thinking about. And so you're like, you're almost feeling guilty. Like you're like, okay, like I'm richer than I was beforehand, I should be happier, you know, but it affects like, you know, you're, it's not just your baby in your business. Like we're always going to build a knowing that we sell one day, but it's like your identity and then like we get into the knock on effects of your family. But then because I was young and immature and didn't really know what I wanted to do in my life. It just, it came through as like stress and unhappiness.
Anastasia: [00:20:34 - 00:21:38]
No, absolutely. An exit can come can create so much confusion. I want us to slow down a little bit because I want to explore that experience you had for two years working for the acquirer. So in my observation, there are basically five things that people tend to romanticize when they agree oftentimes too easily to stay with the acquirer. And one of those things is that they think they will learn so much working in a big organization. Another one is that they think they will still have as much control over the team and then that the motivation will stay the same. And we touched upon it just now and then the last thing is that people assume that their earnouts will be exactly what was agreed. So I would like to get your view on those five things. How it worked for you, whether you had those illusions in the first place and what you learned in those five aspects.
Cory: [00:21:38 - 00:23:47]
Oh, Anastasia is such a good topic. And this is what like, I mean, and this is where I think it's not just, I mean those thinking about selling. This is, this is such an important area. So part of the reason we sold, again I alluded to this that you know, it was us doing the sales. We needed to build a sales team. We were like, and, and it almost sounds kind of laughable like well, you just build out a sales team. Right. Well and again if you put yourself in the mind of a 25 or 26 year old kid and again this is, there's no venture capital. And so I had some mentorship from family and that as well, but not at the scale we were doing. We thought oh, we're going to get, you know, Forbes actually was the gold standard for, for selling at that time. They certainly were. And, and I, I would say it's slightly different. We did learn a little bit, but what we learned, we did learn something but we learned to, we, we thought that we were going to get like a, an MBA in selling. And then what we came in to found at, at that point in digital media it was like oh, it's whining and dining. Yeah. There's some elements of this in terms of like incentives and how you lay out plans and there's some tactical things there. Right. But like it wasn't complicated. You kind of saw that the incentive plan, you're like oh, that's all it is. Oh, that's not that different from what we were doing beforehand. Okay. So and then you know, at that point in New York it was like there was the Forbes had a Forbes yacht. Right. And so you could, if you had a large enough client, I think it, I, I'll get the number wrong, but it was like a big one. Like, it was like, I, I want to say like 100 to 150 people on this boat. Right. So you'd go at Chelsea Piers and it would go up and that, you know, and, and you know, to be a, a brilliant night. And the kind of rule was you weren't supposed to talk business. And, and so when I saw how Forbes set up like the, the sales team and that, like, it was like, I wouldn't quite go say that we didn't learn anything, but we were underwhelmed after we saw it and got a glimpse to it. We're like, we could have done that. We could have learned that on our own. This was like, you know, pretty simple.
Anastasia: [00:23:48 - 00:24:02]
Yeah, I can totally see how that probably added to your sense of regret that you felt, I guess, that you could have figured that out yourself and got into a better end financial exit eventually.
Cory: [00:24:02 - 00:24:51]
I. And I've heard from you, like, we think we're going to learn a whole bunch more about all the other parts of the business. Like, no, we were, we were okay. Like, big organizations succeed because they have this scale, because of this stuff. Usually they're not, usually they're not good at innovation. Usually they're not good at building new products. Usually they're not good at culture. Like, there's all these things. Like, I remember all of a sudden we had this thing where like, we never saw anybody face to face. So people would show up at the office in, in, in shorts and flip flops, like, including me and Wags. My found like, like the founders. And we remember at one point getting like the handbook of like, well, you know, men should wear slacks and women should wear blouses. And I was like, like, what are we in, like the 80s here? Like, it was. And so there's all these things. It was actually the opposite. It was all these things that we think that we were actually doing better. Right.
Anastasia: [00:24:51 - 00:24:52]
So, yeah, fascinating.
Cory: [00:24:52 - 00:25:37]
You know, there. And there were some tw. Like, you know what? There's some great people there. There was one general manager and you know, he would be really. And then the digital ad business, like, how he would negotiate and kind of get, you know, the budget locked in and, and how he would negotiate with sort of the big players in terms of trading off, like, margin for like, certainty. And so like, yeah, I mean, you can always learn from people, but if you're gonna sell to learn. I would really question that assumption. Control over people. Like I said that last example of the employee handbook, like we just had to throw it. Like we had to adopt that employee handbook. HR said we had to do that. And so we're kind of like, well, if someone from New York wants to fly out to Edmonton and see that we're not wearing slacks, then so be it. Right.
Anastasia: [00:25:38 - 00:25:52]
Another sort of expectation that's very common is that people think life will be less stressful once they work for an acquirer. There will be less responsibility on their shoulders. Would you agree with that?
Cory: [00:25:53 - 00:25:57]
It was so stressful. Stress to me is not being in control.
Anastasia: [00:25:58 - 00:26:00]
Like, yeah, okay.
Cory: [00:26:00 - 00:27:29]
It was like the number of nights that I went to bed super angry because you'd get some email and like you would, you would give your opinion and you try to, like you're trying to learn how to be like an employee as well. Right. And so, so part of that is probably not just on the other side of the acquirer. It's probably on the side. There's probably, it's. I want to say 50 50, but you know, as you. We're not. If you're, if you're the average founder, I don't think is. Most aren't meant to kind of fall into line. I mean you've had success by always challenging the status quo. And so as we make really what I thought were dumb decisions, I would get super, super upset and frustrated. Right. And so even though like wasn't the same economic upside, somehow there was like all these negative energy conversations. I don't know, sound cheesy but like I, I don't know, I, like I'm. And I'm not that spiritual a person. But I always feel like you have a good conversations, like positive energy, right. You have a bad conversation takes away. Right. Like I, I spend a lot of time now thinking about like, hey, if I, who can I be around where I get energy? Like I feel better after that conversation. How do I avoid those? There were just a lot of negative energy conversations. And I think it's because that lack of control. And then after a point, I mean you just kind of throw your hands up and go, okay, tell me what to do, boss. And it's like this passive aggressive thing. And then it's like, it's so painful because like that's not who I want to be. Does that make sense?
Anastasia: [00:27:29 - 00:27:31]
Yeah, no, absolutely.
Cory: [00:27:31 - 00:28:31]
Our, our investment banker. He was, his name was Stan Last. Anyway, he was, he was awesome, right? It was tough. Is awesome. He really, really did A great job for us. Right. So he, he actually negotiated with three parties. We had three term sheets and he didn't go exclusive with any one of them. So one of the things he meant, which is a gutsy move, typically in that point when you know when you have that term sheet, you would then go exclusive. Right. But the second that happens, you lose your leverage. So one of the things he negotiated away was instead of an earn out, it was just a holdback. So, you know, we didn't actually have to hit any numbers and it was in cash. So I think you raised a really good point on if whenever I'm talking to another entrepreneur that's going to sell, would you be happy with the amount today if you never received another cent? Because I've heard of so many situations where like you don't get another cent. And so we were fortunate enough to be able to actually negotiate that out, but we still needed to stay around for two years.
Anastasia: [00:28:32 - 00:28:53]
I have so many stories when people just didn't get any earn out or they got so much less. Also there are some other interesting stories that people would give up on the earnouts because they hated working for an acquirer so much that they would actually give up on the money. But then they regretted that they didn't negotiate the deal differently.
Cory: [00:28:53 - 00:29:09]
Exactly, exactly. Right. And I feel like, I feel like sometimes, I mean the playbook is for a large corporate to make life as difficult as possible knowing that there's a chance that the founder will take off and not stick around for that extra money.
Anastasia: [00:29:09 - 00:29:13]
So it does sound like you had a good investment banker, good job.
Cory: [00:29:13 - 00:29:41]
But the mental model that I think what you get to in this romanticism is what cash you get on close and if you get equity and you can hedge that in a way, I mean the Mark Cuban way he did that with Broadcast.com is hitting his widely documented. So. So stock isn't bad if it's liquid stock. Right. Or if there's a way to actually protect your downside. But thinking of that in terms of the purchase prices, what you have on that day, if you would be unhappy with that, don't do the deal.
Anastasia: [00:29:41 - 00:29:44]
Yeah. Did you get any equity as part of your deal?
Cory: [00:29:44 - 00:29:45]
No, it was all cash.
Anastasia: [00:29:45 - 00:29:46]
All cash? Yeah.
Cory: [00:29:46 - 00:29:56]
Yeah, because. And also because. Because the acquirer was a private company and so there was like we were so. So there wasn't really an option to receive cash.
Anastasia: [00:29:56 - 00:30:04]
For someone who is about to sell and is debating whether to hire an investment bank or not, what would you say?
Cory: [00:30:05 - 00:33:28]
You got to get the best so two things in professionals get the best investment banker that knows experience in your industry. So the right lawyers that actually not your lawyer that's being around a lawyer that actually does deals, you actually have to switch your lawyer, in my opinion. And then third, the right tax planning. So the tax planning actually saved us the most. We had this great guy from, it was funny from, from, from PETA, from Price Waterhouse that showed up on the last couple days and ended up, you know, his fee was outrageous but he made us back 10 times his fee. Right. And, and I think that's true regardless of whether you're us, Canada, Europe or anywhere else that you know there's, there's always ways that the right, the right tax planners can get in. So he was actually the best bang for the buck. I would say that the investment banker. So at one point we weren't actually in the room but being able to negotiate back and forth and like he did, he did create significant value. We, we structured it so that we, we knew we could get an offer for X right. Because we had unsolicited offers. So his fee we negotiated very little up to that point. And then an escalating clause if it got over a certain amount. So he was really incentivized to go for the, go for the any extra incremental dollars and did an awesome job at that and more so than we could have done on our own and also knew the market better than we did in terms of who was and made that call to actually not go exclusive. So that was worthwhile. I the, the mistake we made is we, we need to do a better job negotiating at the onset like from that hold back when what's paid is it paid on the overall? I've seen this happen time and time again. The fee is based upon the aggregate transaction price. But then if you didn't receive 20 or 30% of it, you shouldn't pay your fee on that until it comes afterwards. But of course every investment banker will want that fee on close. Right. So that made for some fun conversations on, on the day the wire came in. But I think the main thing is like what I didn't realize that after doing my first material deal is that switch between investment banker and lawyers. Like the lawyers are the worst people at the onset because it's costing you so much money. But once you've actually decided to go with one party and you go from that negotiation to the sale purchase agreement, then your investment banker is actually your worst enemy because he or she can't do anything else and now it's the lawyer to protect you on the reps and warranties. Like the investment banker could care less on your reps. Right. And so managing those teams often I, I think it's one things like my, if, if I wish we had someone who'd gone through the process because like, if, if someone was going to sell, I mean, for someone like yourself that sold multiple times, if an entrepreneur came to you while they were in a deal process and gave you the structure of the deal and said, like, help me see the forest through the trees. That's where I think as entrepreneurs we need to help each other out because we're always going to be outmatched on their side. They're going to do 50, 100 more deals in their career. They're deal professionals most of the time. But most founders only ever get one or two deals in their life. Right. And so we're totally outmatched.
Anastasia: [00:33:28 - 00:33:30]
All right, so shall we move to post exit?
Cory: [00:33:31 - 00:33:31]
Sure.
Anastasia: [00:33:32 - 00:33:42]
So you're free from your employer two years after your exit. What. How do you feel?
Cory: [00:33:42 - 00:34:06]
There's a family dimension, there's a financial dimension and then there's sort of like a emotional purpose side of it. I don't think my partner would mind me saying this, but like, it was actually way harder on because we were having kids at this time. So actually my daughter was born 12 days before the deal closed.
Anastasia: [00:34:07 - 00:34:08]
Wow.
Cory: [00:34:09 - 00:38:24]
It was a slightly stressful. Right. So, so there's one dynamic of like, oh, sorry, I'm getting called to New York while we've got a six month at home. Wasn't always a fun conversation. But then I think that the difficulty was that there was this extra lay of guilt on my partner because, you know, she had her career, I met her in business school and as, as, as she's making decisions for her personally, she's like, well, should I keep on going with this job that I have now when we've got all this money in the bank, while we have the pressures of motherhood and what time to stay at home? And so again, without telling her story and going into that, you can imagine that dynamic where beforehand, if you didn't sell well, you just, you know, you take your maternity leave and you go back to work and you kind of continue on. The freedom to not have to work actually creates massive stress and a massive problem. And, and, and I, I think especially for mothers, a huge amount of, you know, I'd say motherly guilt. Right. So it, yeah, it, we've talked about that a lot since that point. I Mean, and again, I'll leave it at that because again, it's her story, not mine. But I do think that that's one thing that I didn't foresee. Right. Like having more money is always better, right? Well, sometimes actually, you know, the, the guilt that comes from that can be, I mean, it's hard. There's choices that you have to make then like sometimes that freedom results in choices that are emotionally painful. I think of selling as you have, 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, like, you know, we didn't do anything stupid. We didn't go buy a Lamborghini or anything. Like, I shouldn't say it's stupid, but 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 going to do anything. We just kept ourselves, kept it in Treasuries, right? Yeah, but so I'm Canadian. We sold in US dollars. We had everything just sitting in US 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 month. 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 collars 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. But it was, it was, it was a different type of stress. And again the whole, the whole thing of like, okay, check, I want it 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, and actually managing in that way if it's of that scale. And then, so I was managing internal capital and you know, I'm A, I'm a big Buffett disciple, Read everything he's ever had. 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, it went down, bought a little bit more, came 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 stock.
Anastasia: [00:38:24 - 00:38:25]
Oh, wow.
Cory: [00:38:25 - 00:39:14]
And I hit my position limits. Like, I had like a good policy statement. Everything like that 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 know, I'm already at the 10 threshold. Like this thing is like, the Amex will never be this cheap again. You can probably go check the stock today. It'd be probably a 10 or 20 bagger from that point. But I'd hit my position limits. I like tried to be disciplined, right. And so meanwhile, I'm down this massive amount. Now in the end, it came back up and I, I made money off it. But that, 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. You know, beforehand, your net worth was here, right? And, and you, you, every month, every quarter, you go up and you're happy.
Anastasia: [00:39:15 - 00:39:15]
Yeah.
Cory: [00:39:15 - 00:39:31]
Now your net worth is here, but there's a little. You're still way higher than it was. But that delta, the change over that month, that was very stressful. Right? And so this whole idea of like, well, you're, you're this superstar, you just had this X, you have this. But you're actually a shitty investor.
Anastasia: [00:39:32 - 00:39:35]
Yeah, that is so true.
Cory: [00:39:35 - 00:40:07]
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 replace. It's almost like the same thing on a business. You're not like, you know, until you've had struggle 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 gotta freaking mortgage the house or it doesn't matter if you're Richard Branson or anybody else. You've had to Go all in. Right. Until you felt the pain of that. On being an investor, you know, you have, you're not sort of battle hardened, right?
Anastasia: [00:40:07 - 00:40:46]
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 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.
Cory: [00:40:48 - 00:40:49]
I made a bunch of.
Anastasia: [00:40:49 - 00:40:52]
After you realize you're a horrible investor in public equities.
Cory: [00:40:52 - 00:42:19]
Well, 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 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 I was actually just managing, I spent all my day managing capital. Right. So I did do fairly well in terms of just. But I was like, like it was like rights offerings, spin offs, 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, I could do okay, right. That so, but 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. And 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.
Anastasia: [00:42:19 - 00:42:21]
Yeah, absolutely.
Cory: [00:42:21 - 00:44:22]
So, so my public stuff was okay. 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 took a couple million bucks, threw in, you know, built a platform to cookie cutter PD sites. So essentially I built a CMS. Like keep in mind WordPress for those who are technical wasn't imagine 15 years ago, you know, you actually need to build from scratch. You wouldn't today, but we launched about 10 of these 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. And you know, we didn't call it a venture studio, which I'm going to venture to 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 the, the sites that we ran ourselves, that we can control, we actually made some money with like not. It wasn't an SP level. I mean there's, 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 then down to not. And so you're putting all these 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.
Anastasia: [00:44:22 - 00:44:26]
Right, so. So you closed them? That's what you did?
Cory: [00:44:27 - 00:44:55]
No, well, no, we, 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. I could hire freelance 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.
Anastasia: [00:44:55 - 00:45:00]
So 2015, again, very early on gen was not.
Cory: [00:45:00 - 00:46:39]
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 you know, I like to joke with, with, with, with Nicole, my partner that, you know, hey, I was, I was a visionary here. And she says when you're three years early, you're wrong. But she was right. She's wrong. We're two years earlier on, but, but we're, we're early. But what I didn't realize at the time is that how a lot of the underpinnings of AI were actually developed here in Canada. So Deep learning was invented in Toronto by a guy named Dr. Jeffrey Hinton and a student at Yoshi Bengio, as in the guy Yan 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. So, like, to give you an idea, it's called a top 10, top 20 school, depending on 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 and 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 density. We just, we were hiring for own business. Instead of hiring two engineers, I hired four. And then people kept on hearing that I could do this AI thing. And then all of a sudden we're like, wait a minute, maybe there's a model there.
Anastasia: [00:46:39 - 00:46:50]
So, Corey, 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?
Cory: [00:46:50 - 00:48:28]
Yeah. Good, because 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 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. And, you know, it's, It's. I don't. It makes 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. I like going from 0 to 1. I like that early stage from my idea and building out something, and 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. 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 to. 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. You can 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.
Anastasia: [00:48:28 - 00:48:41]
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 sort of not. Not creating value.
Cory: [00:48:41 - 00:48:42]
Great. Exactly.
Anastasia: [00:48:42 - 00:48:44]
You wanted to build and create value again.
Cory: [00:48:45 - 00:48:55]
Well. And yeah, like, it's. Building stuff is fun, but it actually took me two, three, four years to figure out.
Anastasia: [00:48:55 - 00:48:57]
Yeah, no, absolutely.
Cory: [00:48:57 - 00:49:14]
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, 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.
Anastasia: [00:49:14 - 00:49:15]
Yeah.
Cory: [00:49:15 - 00:49:29]
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.
Anastasia: [00:49:29 - 00:49:34]
Absolutely right. You just need to take the time. Yeah.
Cory: [00:49:34 - 00:49:41]
It's like, it's almost like, I don't know, self discovery or I'm just weak on that side of, like, knowing who you are. Right. Like, at that point.
Anastasia: [00:49:41 - 00:50:07]
Yeah, but it doesn't have to take that long. Right. If you ask yourself the 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.
Cory: [00:50:08 - 00:50:12]
Did you feel Embarrassed or ashamed that you didn't know after the first one?
Anastasia: [00:50:13 - 00:50:14]
Of course I do.
Cory: [00:50:14 - 00:50:15]
Now that it took me.
Anastasia: [00:50:15 - 00:50:15]
Yeah.
Cory: [00:50:15 - 00:50:29]
I'm sort of embarrassed that, like, even talking about it, like, I'm. I just feel a bit here, like, almost going, like, I. 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.
Anastasia: [00:50:29 - 00:50:51]
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.
Cory: [00:50:52 - 00:50:52]
Yeah.
Anastasia: [00:50:52 - 00:51:00]
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.
Cory: [00:51:00 - 00:51:02]
Yeah, yeah, exactly.
Anastasia: [00:51:02 - 00:51:03]
Absolutely.
Cory: [00:51:04 - 00:51:33]
One. Yeah. And one conversation could save you a couple 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.
Anastasia: [00:51:33 - 00:53:09]
Yeah. I think no. Yeah. No one can tell us what we individually should do. I 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 is so much pride and overconfidence that sometimes we just. 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. And 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 are having Fun. And that's just a romantic idea. And then of course another thing 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.
Cory: [00:53:09 - 00:53:10]
Yeah.
Anastasia: [00:53:10 - 00:53:12]
So you would you agree?
Cory: [00:53:12 - 00:55:53]
I totally agree. And the first two I think are 100 and 100%. 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. And again, like we made money on it, but it didn't scale the difference. Now I remember back in the early days of Investopedia, you know, 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 just bang out more terms or I'd send off cold call emails. Like I'd like. All we did was our life. I mean, we both had girlfriends, you know, that turned into wives after a while. But like 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 mean, with what I'm doing right now, I mean, I think there is a debate. Some days you wake up, you're like, why did I go back to the 60 or 70 hour weeks, right? And I love doing it. That's the thing. I absolutely love doing it. But then, you know, there is this. Beforehand, you had no options, you had to do it because there was nothing there, right. And so the solution 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 to 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 him a million bucks. Right. Like, I. 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 still, like, I've now come to grips with, like, I like being operational, and I need to do that to succeed, at least at this stage for where my next company is.
Anastasia: [00:55:54 - 00:56:08]
So, Corey, your kids are now 17 and 15, so you're quite an experienced parent and I'm really cute. You also mentioned that your girl was born basically at the same time when you exited.
Cory: [00:56:08 - 00:56:13]
Exactly. April 1st, and we closed on April 12th.
Anastasia: [00:56:13 - 00:56:26]
Amazing. So your story of an existed founder is as long as your story of a father, which is. Which is just fascinating for me. How did you reconcile and combine these things?
Cory: [00:56:26 - 00:57:36]
Oh, man. We 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 6, 912 months. My wife might say 3 to 6 months. Like, I. I feel like the, the great things we had, the flexibility to. 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, 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 be around the pool. And 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 and then, you know, when it 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.
Anastasia: [00:57:36 - 00:57:47]
Many exited founders find their purpose in children at first before they move on and find purpose somewhere else. Did you feel that?
Cory: [00:57:47 - 00:58:42]
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 the, the difference in terms of the freedom to make those decisions and the difficulty around that. But yeah, for myself probably. I mean, you want to be a good dad, but I, I mean, I guess part of me wishes maybe it's like you're just, you know, everything was just like that, but 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, 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, how I'm built.
Anastasia: [00:58:42 - 00:59:53]
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 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, but if you get stuck in it for too long, then you are in that situation when you know you, you no longer are fit for, 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.
Cory: [00:59:53 - 01:00:47]
Yeah, well, and, 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 the kids have been in their teenage years, that 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 that, you know, there's this in. So I do have some guilt over that. Now we're doing. But there's some deals there for like the, you know, like, like we, we were as present as you can get for the first, you know, 10, 12 years of your life. And then yeah, we started this of course. And, and you, so you try to balance that off and so, so sometimes with travel schedules and that I mean that, but yeah, so, 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.
Anastasia: [01:00:48 - 01:01:10]
But aren't you an amazing, 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.
Cory: [01:01:10 - 01:02:45]
In my heart of heart, Like, I hope that's the case. Like, I believe that'll be the case. Like I think involvement in, in the community, you know, the philanthropic side, you know, and then, you know, 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, 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 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, you know what? You. I could just stay at home and, and be, not just stay at home. I 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 this not, you know, the entire time and, and being there. You could do that. I, 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 and I think I've been there.
Anastasia: [01:02:45 - 01:02:51]
I, I'm not sure your teenagers need you. I'm not sure your teenagers need you 24 7. They probably want their friends and then.
Cory: [01:02:51 - 01:03:41]
There'S that too, right? And I think back to like, like, hey, I'm around way more than my parents. Like, you know, growing up in the 80s. Like, part of me thinks 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, you know, like never mind, like salesman, like never around. Right. Like so, so there's an interesting parallel. Your purpose versus kids. And again, the strain of freedom, the freedom to make the right decisions and then how that then manifests itself when you're trying to balance those things.
Anastasia: [01:03:41 - 01:04:03]
Yeah, true. Corey. This leads us to the hottest question in our Tiger 21 community, which is how to raise kids with wealth. What approach did you take how to avoid them being entitled, lazy?
Cory: [01:04:05 - 01:05:52]
We are. I mean, unless my kids watch this, they don't know any of the details. And the one thing that's come up 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 we've, like, they don't. There's not a whole lot of ways they can see it. And so we've, we're very much taking the approach of keeping things. I mean, they know we've sold a company. They know that. They know clearly from our house that we're not poor. But it's, We've 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 going to have to work, they're going to have to do the things. They're going to have to create their own life. And you know, if, if, even, even if, 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. And so I think a lot of people have that idea, but how we've actually implemented 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 them 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.
Anastasia: [01:05:52 - 01:05:57]
So are you inspiring them intentionally to become entrepreneurs?
Cory: [01:06:00 - 01:06:52]
It to my dismay, I think the hours we work have have might actually be doing the exact opposite. I, 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 like in 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, 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, and I don't want to unfairly push someone into it who is not, it's not in their blood. I mean it should be in there, but you know what I'm saying.
Anastasia: [01:06:52 - 01:06:54]
Yeah, it kind of should be.
Cory: [01:06:54 - 01:06:55]
It should be. Right.
Anastasia: [01:06:55 - 01:07:04]
And so Corey, I wonder, I wonder, are you doing enough to show them how fulfilling that hard work is?
Cory: [01:07:04 - 01:07:17]
Oh, now that's a good question. I'll have to ruminate on that one. The fact that I can't say yes probably gives you your answer.
Anastasia: [01:07:19 - 01:07:25]
Sorry for putting you on the spot like this but it was just a logical, logical question. Question.
Cory: [01:07:25 - 01:08:50]
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. And 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 these 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 just say middle class, like just being, sticking to your roots but then also being able to be comfortable anywhere. To me, that 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, in, you know, and smaller, you know, in the middle of, of the country, right. It's different.
Anastasia: [01:08:50 - 01:09:05]
I don't know, it's. I, I think it's quite hard to raise kids in big cities too for different reasons. There are all, all these confusing messages. Oh, 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.
Cory: [01:09:05 - 01:09:27]
Well, and so I do think it's easier to be there, but I also want to have them to be success so that when we go to New York that like you're not, like you're, 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 of course finding that balance there, that's been a tricky parenting exercise.
Anastasia: [01:09:27 - 01:09:40]
Yeah. Okay, so what, what's your mindset today comparing to when you sold the business with respect to operations and systems and, and all of it? How would you summarize that?
Cory: [01:09:40 - 01:10:56]
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, actually having a value based organization that's, you know, 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, on, on energy transition and climate change. And so, you know, we talk like applying AI to elevate human potential is our purpose. So it's building tools that help people make better decisions and applications that we think are going to change industries. So like, 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.
Anastasia: [01:10:56 - 01:11:28]
So I heard some really important things here, Corey, which I want to make sure we emphasize. So 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.
Cory: [01:11:28 - 01:11:29]
Yeah.
Anastasia: [01:11:29 - 01:11:30]
Is that a correct description?
Cory: [01:11:31 - 01:11:33]
Right. Like, yeah, you know, to.
Anastasia: [01:11:33 - 01:11:48]
So, yeah. So. 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.
Cory: [01:11:48 - 01:12:13]
But I love, I love working. I love the challenge. I love. I love bringing together teams and finding new ideas and, and probably the biggest positive plus energy thing is I 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. That gets me going. It just took me like a decade to figure it out. Right.
Anastasia: [01:12:14 - 01:13:29]
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 this fantastic companies. And I talked to them, like 10, 13, 15 years after their exit, and 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.
Cory: [01:13:29 - 01:14:21]
Well, but it. I mean, usually I would go into detail 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. And 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 years our kids were young and we traveled over 100 days a year and like there's lots of amazing things there. 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.
Anastasia: [01:14:22 - 01:14:23]
Yeah.
Cory: [01:14:23 - 01:14:45]
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. Of course building a company is always freaking hard. It's always hard, right?
Anastasia: [01:14:45 - 01:14:46]
Exactly. My conclusion too.
Cory: [01:14:46 - 01:14:48]
It's always your entire life, right?
Anastasia: [01:14:49 - 01:14:49]
Yeah.
Cory: [01:14:49 - 01:15:58]
And so, 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, my entrepreneurial grit if you want to call it. I guess I don't know 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. 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 learnings you can scale it up faster. There's that things you could do better. But there is a natural growth of businesses and you can't just fast approach at all. And 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, and I, and listen if someone's listening, I'm more than happy to have a conversation just ping me on LinkedIn on this, this or anything other topic.
Anastasia: [01:15:58 - 01:16:58]
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 founders dilemma because it's so common and 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. Like 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.
Cory: [01:16:58 - 01:18:03]
That resonates, that resonates with me big time. And I've seen that people like 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 necessarily just entrepreneurs. When people retire, all of a sudden they're so busy, right? You know, they move on to Mexico or wherever and they, it's, you know, they, or they, or they go to somewhere in the Caribbean. It's like they're so busy, all that. Well, what did you do? It's like, like oh, well, I had my workout and then you know, you know, met for lunch and then oh my gosh, goodness. And then like, you know, 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, and, and, and so even entrepreneurs, once they've gone, you, 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, but then there's almost an expiry date where then you're out of your network, out of your connections and then.
Anastasia: [01:18:03 - 01:18:56]
You develop self doubts, right? Then you're not even sure you can do it. And then there is more to overcome if you try to do it later. But another thing I found is that 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. 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 I think if people don't have a clarity on what actually gives us a sense of purpose early on, we are looking for 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.
Cory: [01:18:57 - 01:19:10]
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.
Anastasia: [01:19:11 - 01:19:45]
Exactly 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 it becomes very important because I think humans early on we're just learning to survive, but once we've learned to survive, once we've learned the skill of securing resources, we naturally want to contribute to give something. And if we are not given, then it becomes a very unhappy existence.
Cory: [01:19:45 - 01:21:38]
Yeah, totally. And you can almost do the Elon Musk, Bill Gates comparison there 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. It, it, it, it really is the, 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, Dean, 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 and then do it. But I always find that like all the amazing. You almost always go on all in. And in some ways, like, entrepreneurship's like a disease, right? Like, you're always like, well, I've always got back up then, 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, it would, you know, you want to make sure that your kids are okay in your estate and you got all that done, you know, and it's easy on, in theory. But I'm curious, like, your thoughts on that one afterwards. 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, right? 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?
Anastasia: [01:21:38 - 01:23:06]
You know, I actually found that creating financial stability and some sense of, of safety is extremely helpful for the next business. And that realization unfortunately came to me a bit, a bit too late because I was very much in, into this. I'll go all in in my first attempts to create SQLs after the first exit. But 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 the Maslow pyramid, we have the financial safety 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. And once we have this sufficient satisfaction on that level, we naturally want to do other things. I personally came to the conclusion that if early on we actually take some boring but necessary action 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.
Cory: [01:23:06 - 01:24:14]
That's. Yeah, that, that resonates, I think. And that's, I think that is something to strive for, that mental model. It makes me think of 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. 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 it was like this, like consistent, you know, and so you, and so you see these stories of, of being on the edge, right? And then when you're on the edge and having the discipline of like, okay, I'm putting this in my safe pile, but then always having to go in more, always trying to come into that. And I mean like, like even like Tesla four years ago is one month or whatever, one a 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 Exited 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?
Anastasia: [01:24:14 - 01:27:04]
I think this, this kind of masochistic approach, financial masochism often comes from the ide. We're not hungry financially, we will not have motivation. And 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, 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. And 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. 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. And 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, 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 for me, for example, my mission 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 contributing to this, this is so important. This is what makes me get up in the morning and work. And I'm so, so, I'm so lucky, so grateful that I don't need to do it for money, because it wouldn't be the same thing.
Cory: [01:27:06 - 01:28:42]
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. Financial masochist. 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. But when is enough for what you've accomplished, for what you've built? Right? And how do you strike that bat? Is it, you know, 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? Like, that edge? Cause, well, that. That sort of ang. It causes angst, this 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, it's. I, I find one of the hardest things about the next time around. Right. Like, I should be doing more faster.
Anastasia: [01:28:43 - 01:29:09]
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, and be inspired by that. Because that's essentially what it is. You 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.
Cory: [01:29:09 - 01:29:12]
Yeah. See, it's almost like you've thought about this a little bit.
Anastasia: [01:29:12 - 01:29:13]
Yeah.
Cory: [01:29:13 - 01:31:50]
I'm a big Mental Models fan, right? And so I'm always trying to, like Charlie Munger talks about your lattice work of mental models. And, you know, you can have having that success at a young age, like at 27, I think builds almost as 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. But 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, 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, you know, if, if I could go back to my 27 or 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? 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, right? 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've still got, you know, at least 30 years and hopefully with all along maybe we can invest in some longevity stuff and hopefully it's longer than that, then you can do more, you know, more stuff for longer and, and have more fun, right? 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 is going to be amazing. And so anyway, I could ramble on about that but like does that. You asked a very difficult question, so let me pause there. Versus at the risk of rambling on.
Anastasia: [01:31:51 - 01:33:10]
The bottom line is that 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? Embrace 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, don't believe me, but look at Corey's story.
Cory: [01:33:10 - 01:33:12]
Here's the way that Corey fucked up.
Anastasia: [01:33:13 - 01:33:26]
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.
Cory: [01:33:26 - 01:34:45]
And if we can support each other and build those connections, right? Like even 20 years ago we would have, 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 you know, and, and again groups like YPO or 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 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, 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.
Anastasia: [01:34:45 - 01:35:38]
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 it's. Is so important is this, this skill of creating inspiration deliberately, whether it's by talking to other people or to exposing ourselves to what's really inspiring and important in this world. 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, 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.
Cory: [01:35:38 - 01:35:54]
Important, intent, being intentional about inspiration. That, that's a. Yeah, yeah. How many people actually do that? I think, you know, inspiration, we, 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.
Anastasia: [01:35:54 - 01:36:10]
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.
Cory: [01:36:11 - 01:37:02]
Totally, totally. Well, and, and, and I mean, I think there's also some dynamics there. 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 gotta, 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's, 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 the tricky part is being able to actually build out that, you know, those frameworks and you know, question.
Anastasia: [01:37:03 - 01:37:48]
I definitely want to, to create more of that. I think it's extremely important. It's, it's not just communication skills but it's also the way we feel in, inside. It's this non transactional mindset with respect to other people and that we need to, and sort of this ego that prevents us 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 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.
Cory: [01:37:48 - 01:38:04]
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.
Anastasia: [01:38:04 - 01:38:23]
And it's natural, but I think it's by overcoming this we can open up. Right. It'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.
Cory: [01:38:23 - 01:38:47]
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, all the emotional stuff there, it's, you know, emotions. I'm told that emotions aren't exactly my strong, strong, sweet. So, you know, I'll, I'll keep on doing stuff like this, like to work on it. Right.
Anastasia: [01:38:48 - 01:39:12]
Well, I think you, you're way by above average in my book. Oh, Corey, 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?
Cory: [01:39:15 - 01:40:25]
I 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, you know, if we're talking from a business perspective, I mean, I think the most important thing is that my, my kids over the long run respect me and, and have learned and I've given them the opportunity. But you know, if I could, if, 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. I'm on my deathbed. If, if I. Because it. And you know, cure is a big word. Right. And so, you know, I've, 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, the health side, the AI side and figure out how to kind of throw enough capital behind that, that that would be success.
Anastasia: [01:40:26 - 01:40:31]
Yeah. This is so beautiful. Thank you so much, Corey.
Cory: [01:40:31 - 01:40:34]
This has been so much fun, positive energy conversation.
Anastasia: [01:40:35 - 01:40:36]
We'll have to do it again.
Cory: [01:40:36 - 01:40:36]
Plus two.
