E51: Big Deals & Bigger Lessons with David Kassie

This podcast is brought to you by Ginsler Wealth. The information discussed today is meant to be general in nature and not tailored to your specific investing circumstances. This means that you should talk to your regular Ginsler wealth advisor or your own advisor before acting on any information we discuss today. Nothing in this podcast is intended to be a solicitation and past performance does not guarantee future returns. This episode is in our series of Lessons with Leaders, so get your notebooks out. Today on the Limited podcast, we speak with David Cassie, Chairman of Outcome Asset Management and Chairman Emeritus of Canacore Genuity. We talk about his investment banking career, leading strong performers and big deals and his biggest lessons. Let's go. Well, welcome everybody to another episode of the Unlimited podcast today. This probably falls into the category or the series that I call our Lessons with Legends we have today. David Cassie, Chairman of Outcome Asset Management and Chairman Emeritus of Canaccord Genuity. He is well known in the Canadian business circles and what we're going to do is cover, I hope, his backstory, his move into banking at Wood Gundy and ultimately, I guess, CIBC, what life was like as a banker in the 80s, 90s, 2000s. And we'll also cover his exit from CIBC with the launch of Genuity. I was there at the time. It was a big, a big day, big shock at CIBC and the evolution of Genuity to Canaccord and, and to his current role, as I said, as Chairman of Outcome. So David, thanks so much for joining.

My pleasure. Good to be here, Brian.

I'll give the sort of not super long but not super short, quick formal introduction of you, but then, as we always do, we'd love to hear sort of you tell the story of your evolution. So again for our listeners, David is Chairman of Outcome Asset Management and Chairman Emeritus of Canaccord genuity as of August 2024. He was chairman or executive chairman of Canaccord Genuity since May 2010 and was chairman and CEO from April to October 2015. David was principal chairman and CEO of Genuity Capital Markets from November 2004 to May 2010, at which time Genuity was acquired by Canaccord Financial. He is the former Chairman and Chief Executive Officer of CIBC World Markets and the Vice Chairman of CIBC, where he was there at, I guess, Wood Gundy and CIBC from 1979 to 2004. He has extensive experience as an advisor, underwriter and principal. He sits on a number of corporate boards, is actively involved in community and charitable organizations, and is a director and Former chairman of Baycrest Health Sciences and was formerly on the boards of the Toronto International Film Festival Group, the Hospital for Sick Children and Ivy School of Business. He holds a BCom with honors in economics from McGill University and an MBA from the University of Western Ontario. So again, welcome There's, I mean, as I read the bio, you've been a chairman and CEO for many places and many, many years. So obviously very senior, very experienced and really looking forward to hearing, hearing the story.

Okay, well, maybe I'll start, Brian with a brief executive summary. I mean you gave the titles, but just in terms of my journey and then talk about what I'm up to right now and then we can circle back to anything of particular interest. So as you mentioned, I left what today is Ivy Business school with an MBA in 79. And really my career has been in six acts, if you will. The first act was an Investment banker from 79 to 88, 89 at Wood Gundy. In those days we were generalists. We did everything, every type of product, every type of industry and it was really a very heady time before anybody knew what an investment banker was. That was kind of my formative years, heavy, heavy on learning. In the 88, 87, 88 time frame, the Canadian banks, if people aren't familiar, were allowed to buy the investment dealers which were all partnerships at the time owned by individuals. And in Wood Gundy's case, CIBC bought Wood Gundy. I had decided as and after that happened that I didn't want to be an investment banker any longer. I wanted to be a principal. And they didn't do that. And I was actually going to leave, but they suggested I do that there. So I started a merchant bank called CIBC woodgundy Capital with Gundy actually still had a minority interest from the partners. So it was important that it was a joint venture, if you will. And I think I was one of, if not the first person to walk around with a real business card that had both the bank name and the investment dealer name in it and doing something that covered both sides of what at the time was a very controversial cultural get together, which was a commercial bank and an investment bank. This is back in the late 80s. I became chairman and CEO of CIB. What became CIBC Capital Partners at the time CIBC would Yundi Capital. I did that for about five years full time and then I was asked to take over investment in corporate banking and then shortly after taking that over, build it out into a global investment bank. So for the next 10 years, from 93 94, I was head of initially investment, corporate and merchant banking globally and then ultimately my last five years as chairman and CEO of CIBC World Markets. So the Act 2, if you will, was the merchant bank. Act 3 was basically a senior executive CEO, business builder. I was doing deals as well, but really building an organization. I spent the vast majority of my time outside Canada, particularly in the US was semi stationed there for a good part of 10 years. And then in 04 succession occurred at CIBC. I had been the designated successor. About a year later, just to make the record clear, about a year later started Genuity. So Genuity was a fluke, I can talk about it later as, as to how it happened. But that ended up being Act 4 for me. It was a straight startup, no premises, no clients, no revenue, nothing. And there we were, hired about 100 people with part, you know, it started with two partners and yeah, it was interesting times to say the least. We did that for five years, then sought to have some sort of monetization. Ended up merging with Canaccord to be Canaccord Genuity. That became Act 5 for me. I became full time executive chair of that briefly as you mentioned, stepped in to be chairman and CEO in 2015 when the CEO tragically died in doing a triathlon, did a succession and then carried on as Executive Chairman. So from 2010, April 2010 till this past August I was essentially mainly full time executive chair of Canacort Genuity for various reasons including not wanting to have a lifestyle where I traveled all the time. I stepped down in August, this past August was asked to carry on as Chairman Emeritus. All that means is I go to board meetings, the odd strategy session if invited and a handful of investment banking clients. But my, my full time gig now is Chairman of Outcome Asset Management, you know, working with Noah Solomon and Beth Philp, which is Act 6 for me, which is kind of late in late career. But you know, I feel very, you know, energized by what we're up to. It's got best of class performance over the last five years in its equity income fund. It's an algorithmic strategy, albeit steeped in investment theory. And you know, it's small right now we're about 250 million of assets under management. But you know, basically with me now joining Noah and Beth, be doing this full time. Yeah, I'm pretty confident we'll take this to at least several billion over the next three to five years and then we'll go from there. It helps of course when you have the best investment performance, because that's very critical. And yeah, I'm very, very enthused about that because it gives an opportunity to help primarily Canadians right now with their wealth giving best performance. There's a chart we have where the difference between a 10% return a year and an 8% return a year, which is 2% on a $10 million investment, is over $20 million. That's the difference. The magic of compounding. So it's a big deal. I think it's an area that's notwithstanding how invested Canadians are is not well understood, ironically. And I think if we can add value to, you know, Canadians with their wealth for their retirement, you know, that feels like a worthy objective. So that's. That's where I am today.

Okay, well, got lots and lots of questions, but let's just start for a second back from the current, just because you're on the topic anyways, can you just dive into a little bit more about outcome? You said, you know, an area or investment approach that some Canadians or many Canadians don't understand. Maybe just describe what's happening over there a little bit more and why and or how the firm has generated the performance. You vote lined?

Sure. Well, maybe I'll step back a bit because it kind of puts it into context. Noah Solomon was at Goldman Sachs for about 10 years when I met him in 2008. So it was still genuity. And we had one principal business at the time. In addition to being an M and a investment bank with a little bit of capital markets, we had a $400 million private equity fund. Given my background. And we had intended to get into the alternative asset management space, but I didn't see anything. I had many conversations with portfolio managers at brand name money managers who wanted to be owners, but they all kind of had a very similar approach that looked a lot like the index. And, you know, the returns were okay, but they weren't great. And the approach certainly wasn't differentiated and we didn't want to do anything unless it was really differentiated and excellent. Noah described. I met him by happenstance in New York in 08, early 08. And I was introduced to him and he had described to me what he was doing. And it was kind of an aha moment. I loved it. Number one, the returns were really good over a long period of time. My experience back at CIBC World Markets, where we had lots of those types of strategies as they were great until they blew up after one to three years. So his approach sustained. It had very low volatility Which I liked very low drawdowns and terrible markets, meaning it didn't go down nearly as much. And I really liked the fact that it was algorithmic, it was steeped in investment theory. But he had algorithms that I guess in Today's parlance used AI. It went through 25, 30 years of data to develop the algorithms. So I really liked that. My experience with investment committees was that they weren't great decision makers. They were too emotional to, too early, too late to what they read in the Wall Street Journal. So I liked the fact of an unemotional algorithm. Long story short, Noah joined to be 5050 partners with Genuity in 2008. We gave him notwithstanding it was obviously a very challenging time during the financial crisis. We gave him some partners capital to incubate the strategy and a year later it was the only strategy that I knew of that had made money in the prior 12 months. So we went out, we raised probably about 100 million very quickly. But then did you know the genuity. It was the five year anniversary, we ended up doing a merger with Canaccord. I had told the 40 plus partners we would look at some sort of monetization. And the two, it was a publicly traded investment bank. The two principal businesses were not included. As the largest shareholder at the time, I didn't think it made sense to have them included. They get no value there. So I carved out of my time to carry on for a small minority of my time to be given fiduciary obligations to be chairman of each of the private equity fund and Noah's business. The private equity fund we ran off over the next five to seven years selling all the underlying investment investments in Noah's case, you know, sort of very slowly marketing over time. He decided that he wanted to change the strategies after a few years to something as he liked to say, for the next 20 years, not the last 20 years. And it's really about seven, eight years ago that we did that. And the Canadian Equity Income fund as I mentioned, which is a very clever algorithm, pretty simple, it's basically, I mean it's a little more sophisticated than this but dividend yield divided by beta and 50 large cap dividend paying Canadian stocks that everybody know every company in the portfolio. But the magic is that the algorithm weights them in a way that maximizes the benefit of dividend yields divided by beta which is a proxy for volatility and that has produced the best returns. And most Canadians would know this, but 90% of managers underperform the index over the last five years, roughly 90%. This is one of the few that actually outperform the index, so adds value. And that's one of the reasons I'm just so enthused about this because yeah, and it's sustainable. We know exactly why it does exactly what we expect it to. So very, very excited about that.

That's great. Okay, so that was what you ended your overview with. Maybe go back to the beginning, you know, and I was in the investment banking business as well, but much started much, much later than you. You joined wood Gundy in 1979. Eventually the banks could buy these private or principal owned investment banks. But what was, what was banking like in, you know, the 80s, 90s? You know, I've always heard stories of wild, wild things. You never know what's true or what's not true. But what was it like, you know, becoming a leader in that area for that first act, I guess of your career? What was life like then? And as always, feel free to compare to now because times have changed for sure.

So I have to say that first 10 years was unbelievably exciting. I was like in my early to mid-20s when I started and would. Gundy had a dominant market share at the time. And you were working with CEOs and CFOs of every major company taking companies public. And the big difference, just to compare it to today, you know, and obviously the world has evolved. But you were a generalist then. Pretty much. You know, I worked on bond issues, I worked on equity issues. We didn't call it this, but I worked on securitizations. I worked on virtually every industry today. It would be highly specialized, sometimes within an industry, you know, like a little piece of an industry. So I worked on tech, oil and gas, mining, forest products, consumer insurance, banks, real estate. You know, if I had a major, if you will, during that time I worked on, which was very exciting because it kind of changed the whole capital markets. I worked on all the British privatizations that were undertaken by the Thatcher government. So I was commuting from around 84 to 89, not every week, but pretty frequently to the UK and occasionally to Europe as Wood Gundy was almost on every one of them, the lead advisor. British Telecom, British Airways, British Gas, British Petroleum, which was an interesting because, interesting deal because it happened during the crash of 87 British Water authorities, British electricity boards, et cetera. So it was a pretty, pretty heady time.

How did this Canadian investment bank become the lead advisor on all these British deals?

So the format that Her Majesty's Government, hmg, that, that, that was your client, if you will. Her Majesty felt a little bit like James Bond. The, the format was that they hired a UK advisor, the company or the industry being privatized or the company being privatized hired an advisor. And then because they were so large, these offerings and the UK market, the London market was pretty small by comparison. They hired a lead underwriter advisor for each of the U.S. canada, Europe and Japan. So in each case there were four. In addition to the uk, there were four separate lead advisor underwriters for those markets. Ironically, of course, the US being the way they were, tried to talk Her Majesty's government to letting them handle Canada.

But the 51st state, you mean?

Exactly. But the British obviously were very sensitive to that notion and told them to hit the road. And that's why Canada, which hit way above its weight for the TSX at the time and in terms of distribution. But yeah, obviously Canada was a relatively small country compared to those other markets. But as I said, we more than held our own. So that's the reason why Canada and Wood Gundy was the lead advisor for all these offerings.

Okay, got it through that and then I guess CIBC acquired Wood Gundy and as you said in act, maybe three, I can't. Lots of acts, hopefully I get them right. You know, you took a real leadership role, obviously leadership management, like what, what was the challenges or the, you know, some of the interesting parts of that role of becoming sort of a leader of a much, I assume was a much larger organization, obviously clearly doing an amazing job. But as your leadership roles kept progressing, how do you shift from banker to leader and any interesting challenges or lessons from doing that? Hard to lead bankers in my experience. Not that I was a leader of bankers, but I was a banker and saw the personalities.

Well, you're absolutely right. So very insightful observation. So Act 2, which is I started a merchant bank which, you know, we were only about, I don't know, I'm going to say 15 people and we grew it to about 30, 30, 40 people over time in the US, UK and Canada. Initially, you know, that that by comparison was relatively easy management wise because it was relatively few people, you know, in terms of the transition, ironically, I remember to your point, I had not been a manager, I had been a leader of a team, if you will, in investment banking, but not building a business. And I guess my, you know, my observation would be having been an Investment banker for 10 years at Wood Gundy, which was as good as it got at the time, there was Very little management at Wood Gundy. You know, it was a partnership, everybody did deals, every, it was client oriented. So it was a wonderful culture that way. But you needed to be a self starter and not really care about getting a pat on the back or et cetera. So I had never had a performance review or anything like it. By the time I finished that stint I kind of thought that there should be, not for me, but just generally. So I remember going overboard when I started the merchant bank doing these 360 performance reviews where I literally would talk to 10 to 20 people in a person's orbit below beside and above them and give them, you know, a very detailed performance review. Strengths, weaknesses, areas for improvement, very constructive. People were initially really cowed by that because nobody had ever done that. But you know, I remember one, one fellow who is a very talented guy ended up leading the group eventually said to me, he said, you know, he said, he came in one morning, he said, you know, I didn't sleep last night. He said you gave me my review. And he said nobody's ever talked to me like that. I was a little taken aback. But you know what, I'm, you know, I really thank you. I took it to heart and you know, he really upped his career. He was very talented but he was kind of coasting in his own words. He said, you know, I just do what I have to do. And all of a sudden he got really motivated and et cetera. So yeah, so they actually, they actually work. So that was, you know, that was a very different, it was a little bit of a laboratory for me. Obviously 90% of my, 95% of my time was doing deals and what today would be called private equity, private credit, bridge loans, hedge fund like strategies. So it was kind of an all purpose merchant bank that we grew from initial capital of 50 million to at its peak 5 billion almost 10, 15 years later. But the, the real challenge management wise was when I was asked to take over investment in corporate banking in 93, 94. Yeah, I decided and CIBC at the time, in part because so many of the woodgundy senior partners had checked out after the takeover, had fallen from first or second place to last place. So it was basically a rebuild in addition to building it out in other areas of the world, particularly the US and it was, I have to say it was exhausting because I came up with a strategy that I thought would differentiate us and take advantage of the merits of the commercial bank, the corporate bank and the investment bank, albeit they had two completely different Cultures and that was really challenging to bring those cultures together with both sides. And it was like fighting an election. It felt like fighting an election campaign every day. But I have to say it took a few years. So that's not something that goes fast. But from 93, 94, I would say 96, 97 in particular, it was really working and none of the other banks had done it. So yeah, it was a differentiated strategy and a very powerful one and it vaulted us back into first place. But the real lessons were, boy, it's hard to deal with people and cultures and you know, you really have to be hands on and deal with each individual, you know, on a personal basis, etc. So very challenging.

Well, I remember. So I was in investment banking after undergrad, that went back to grad school, came back, I was at National Bank. I started at First Marathon. Obviously they got acquired, but I was at national bank and got a call from the leader of the financial institutions group at CIBC at the time asking me would I want to come over. And to be honest, I wasn't sure if I was going to do investment banking the rest of my life. But the key decision for leaving national to come to CIBC was that CIBC was number one, they were the top. And so I figured, well, I don't know if I'm going to do this the rest of my life, but why not do it at the top firm and see how things, you know, see how it goes. And CIBC was great. Ultimately I decided as I, you know, as I sit here today, to move to the wealth management, investment management world. So I guess in some way your, your leadership that got you to number one was something that got me interested in CIBC way back when. And then speaking about that, so I joined CIBC in 2004 I guess, and then very shortly after a whole bunch of people disappeared one day from CIBC and they, they went to Genuity. Maybe you could talk a little bit about. You launched Annuity with some partners and a whole host of people came with you. So how did you get folks to follow the leader there and take the big plunge from what was probably a pretty secure, stable thing at cibc? I remember it was a big shock that day when a whole bunch of people literally just on the same day basically disappeared.

Right. So I left in just. Everybody gets a chronology. I left in early February 04. Yeah, Genuity was a fluke. I was, to be fair, it was separately after me and they didn't report directly to me. They were I think co heads of investment in banking or Canadian origination. I can't remember what it was called. But Phil Evershed and Dan Davio, each with their own particular circumstances and at different times, left in the ensuing six months and they had worked obviously closely together as co heads. They approached me in, I'm going to say around June of whether they wanted to start a new investment bank, whether I'd be their partner and do that. I have to admit that at that point, first of all, I was going to take a year off and I had already taken four or five months off. I hadn't had any time off since college. I was probably going to move to New York was my thinking. And it was. I was going to be in private equity, you know, either a name partner in my own fund or a partner at, you know, a brand name fund. So that, that's probably what I was going to do until they approached me. Yeah, we worked, you know, I remember having sitting in my garden having a conversation about, so what are our aspirations? What are your aspirations? What would this look like? Can we come up with a business plan that where this would be meaningful enough, et cetera, et cetera. I was traveling much of that summer, so we kind of worked on a business plan intermittently, came back in the fall and said, okay, this is really interesting. The reason why it happened. What you described is we decided to go ahead. I went and you had to apply for an IDA license. I remember calling Joe Oliver, who our former minister of finance, he was the head of the IDA at the time. I think it was called the ida. They've changed their name so many times. And I said, joe, I'd like to file for a new firm and get a license. I said, is this a confidential process? We don't want anybody know about it. We don't want to start talking to people for another four or five months, you know, you know, call it in the new year. And he said, it's absolutely confidential, David. I said, okay, great. I send in the application the day after. It's a headline in the newspaper. And how did that happen? Well, apparently so I called up Lilo, say I called up Joe. And I said, Joe, like you told me it's confidential. He says, well, it is. But I said, well, what's the process? He says, well, we send it out confidentially to every investment dealer because that's a notification. I said, that's like skywriting. There's no bigger gossips than investment bankers in our industry anyways. So all of a sudden I'm going to say this was September. We're getting calls and emails from everybody. You know, we had already, I had already gotten some from people saying, what are you up to if you do something, you know, I'd be interested, etc. Etc. But we started getting just a flood of calls. So yeah, we must have interviewed and we wouldn't talk to anybody. I should say this, we wouldn't talk to anybody, whether it's at, whether it was at CIBC or any, anyplace else, without them signing a. You approached us, you know, having been run a bit, you know, run one of the biggest, the biggest platform. Yeah, I didn't want to be accused of poaching anyone, et cetera. So they literally, to see a business plan, they had to say I approached you, which was true. Like we didn't reach out to anyone directly. So, you know, we probably interviewed, I don't know, 200 people plus over, you know, I had to put an addition on my house. So the, the joke was my office was over our garage. So the joke was genuity started over my garage. So, yeah, so we interviewed a lot of people. We started day one with about 100 people in, you know, December, January, and you know, of which frankly only about 20 were from CIBC World Markets out of the hundred, you know, notwithstanding the headlines, it wasn't exactly a CIBC World Markets firm. But anyways, obviously the lawsuits, the lawsuit came from CIBC because I think they were really concerned about how many people were going to leave and they thought that would have an impact on people not leaving. That's what happened. And so we started the beginning of 05 effectively and you know, it was, that first five years was pretty interesting, I can tell you, because, you know, I, I not only did I interview a lot of people, I interviewed a lot of people, spouses, you know, because they were. People were leaving jobs where either they were guaranteed or effectively guaranteed. You know, you, you kind of knew what you're making. So yeah, you could be making, you know, let's say a million dollars. You know, at one of the investment banks with bonus, your salary might be 150. But you know, on average you had an 850 bonus. In a bad year you made 600. In a good year you made a million and a quarter or something like that. But that's the type of people, you know, you can move the fulcrum there a little bit depending on the area, but that's the type of people. And all of a sudden they're coming to a place where they were going to get a 150 draw. No guarantee. No. We had no revenue. We couldn't tell them they were going to get a bonus and they had to write a check for the equity.

Right.

That's, you know, like that's, that's a leap of faith. Notwithstanding, it was treated as if it was, you know, like, you know, we have lured people away with, you know, pots of gold or something. No, you know, and the money, the money, we had no outside investors. The money was, you know, the senior partners. Initially I mentioned Phil, Dan and myself, then others joined. Yeah. From various areas and, you know, and everybody wrote a check. Basically, at the end of the day, we had over 40 partners.

Amazing. And so I want to ask you a little bit about the entrepreneurial side of that, but I mean, sounds like for that process and through your career, you've interviewed, you've hired hundreds and hundreds of people. You know, what are the traits of the people that you're, that you've hired over time that have proven to be, you know, you know, the best measure of success or the best foretelling of success? And what sort of interviews do you have where you say this is not going to work, like, not like for us.

Yeah. So I mean, if I go back over all the acts, if you will, they're all different environments.

Right.

So if there's a theme of, you know, and I made my share of mistakes. No, no, the one actually, big one, that still bothers me, but, you know, I think I've been good at it. But I would say the number one feature of successful hiring is fit. Fit being the skill set, the, you know, psychological mindset, the objectives, the aspirations of the individual joining to the environment.

So how do you figure that out in the interview though? Because aren't people going to tell you hopefully presumably exactly what you want to hear if you're smart?

Well, I'm very well, first of all, you know, their background, you know, I, I. So it's not about being smart, you know, that it's clear how smart they are or not smart. They, but, but fit isn't about that so much. It's about, you know, do their skill set and objectives match the environment. So for instance, you know, getting somebody, you know, who is really good at CIBC World Markets with the power of a loan book, you know, as a draw to clients and in a. I tried to make it as an entrepreneurial environment as I could, but yeah, it was still a large organization with controls everywhere, as it should be, versus genuity, where you had nothing. Basically, you Lived by your wits. You had no natural advantages except your ideas and abilities to convince a client to trust you, not the firm, you.

Right.

Whereas when you have a brand in an organization and a huge toolkit of different capabilities, you know, and the same person who's really good at genuity might not be good at CIBC World Markets and vice versa. In fact, you know, that's one of the things we knew at genuity. There were a couple mistakes we made where the person was really good in a bank environment. They weren't, you know, it's not that they weren't good, it's just that they weren't happy. It may in one case. I remember the fellow, he was so nervous, you know, because he wasn't, he didn't feel secure and I'm pretty sure he was hearing it at home because he couldn't, he didn't know exactly what he was going to make, etc. It was a bad fit psychologically. There's nothing wrong with their skill set and you know, the type of person they were. It was just a bad fit.

Right, okay, got it. Just as we wrap up a little bit on the banking career acts. 1, 2, 3, 4, maybe just for fun, any sort of big major, exciting, transformative deals that you worked on that you think have an interesting story. Good story, bad story, Funny, I think you had mentioned to me it took four seasons public, you've met with, you know, government leaders, you don't have to talk about those if those aren't the exciting ones. But that stuff's exciting to me.

Well, there's quite a few as you can imagine. Yeah, probably the one that we were at CIBC World Markets anyways I was best known for was Global Crossing where Global Crossing was a fiber optic cable project of laying fiber optic cable across the Atlantic Ocean. And it was an $800 million infrastructure play. And it was the first non telephone company consortium led fiber optic cable project where we were going to have outside investors and the telephone companies would only be customers, not owners. We went and raised 800 million, greenfield project finance. Now we happen to have as an organization a huge amount of expertise because we had lent money and advised on the previous two projects, one called flag, fiber optic link around the globe, et cetera, which were telephone consortium owned. Long story short, as part of the 800 million there was a, I'm doing this from memory, about $100 million equity account. A lot of it was, you know, debt, high yield, senior pref, et cetera. But $100 million equity account of which we took $30 million in our merchant bank. That 30 million turned out to be worth 2 billion. And the reason why, so it's the stuff that you dream of, in addition to all the fees that the organization made from underwriting debt and taking it public and the high yield and the M and A advisory and et cetera, et cetera, you know, and the reason why is because it was in the, we financed and built it in the late 90s and it was just when the Internet boom was taking off, right? And previously the vast majority of what was transmitted was voice. All of a sudden data took off. You know, think of the BlackBerry in everybody's hand and you know, what happened with data and Atlantic Crossing became Pacific Crossing became Global Crossing as we built out other. And all of a sudden we had this giant company where data had just taken off. And I can't remember but I'm going to say at its peak, this $800 million was about, I don't know, 50 billion market cap, which was a lot in those days, like really huge in the public markets. You know, eventually the, the Internet bust and etc. Etc. But you know, we managed to make a gain of approximately $2 billion. So that, that's, that was a good one.

So that's what I call a big deal. Let me, let me talk about small deals maybe because I know that now you're a pretty active angel investor or maybe you have been for quite a long time. Maybe talk a little bit about that. You know, how do you find opportunities? Everyone wants to find these, you know, these age companies that hopefully will be big winners. What are you doing on the angel investing side? How do you find them? How do you vet them? Because, you know, pretty risky. Yeah, how's that, how's that going?

You know, because of my background at the merchant bank, we did some, you know, earlier stage stuff. Probably the, the one startup that comes to mind just because it was probably the first angel investment, albeit it was on behalf of the bank, was Sleep Country Canada. Sleep country was started by an old friend of mine, Steve Gunn and others. And I think the initial capitalization was 2.5 million and we wrote about 20% check on that. And I remember going to get an approved investment committee and I couldn't get it approved because we didn't do startups, right. So I ended up, I had an operating budget, so I expensed it and the, you know, and it ended up being sold, I'm going to say for about 200 million to Bain Capital and then came back public as an income trust for 400 million. So, yeah, we did very well in it. And I always remember, because it was an infinite irr, because I had to write off the investment as an operating expense. So I had that as my background. So I started doing it after I left cibc because everything I had done prior was obviously for the bank, you know, so I did quite a bit, I have to say. I'm not doing much now. I'm busy with outcome and, you know, I'm at a stage where I'm not looking for more. I'm harvesting what I have. But to your question, yeah, I think it's a really difficult area to be consistently successful at. And you're really going to have. It's like vc. You're going to have eight losers and two winners. And you better hope that your winners play for the losers. Unfortunately or fortunately for me, the first investment I made was a huge winner. So I thought it was easy. I'm trying to remember what I invested. I think, yeah, it was a 20 bagger, you know, so I thought, boy, this is easy. And, you know, a few, a few other early ones were five baggers. And then all of a sudden you take your eye off the ball because you're busy building genuity or you're building Canaccord genuity, because, you know, which we spent. You know, I've spent 15 years with the two CEOs, including my own smalls for short stint. So you're very busy. It's difficult, is what I'd say.

Amazing. So just the last maybe few topics before we have to go here. I don't know, you know, how much you want to dive into this, but, you know, like, let's call it the state of Canada and the state of the world. Right now we're talking. We really don't have an operating government. Trump continues to threaten tariffs on Canadian goods. There's unrest in the streets worldwide. Any thoughts on what's happening today and maybe more specifically, what's your advice to whoever is leading this country? I'm not sure who's leading it right now, but any, any advice to whoever is or will be leading this country from your vantage point?

Yeah, I mean, advice. I think I got to be careful here. You know, I wouldn't be too reactive and cowed by what comes out of Trump's mouth. You know, he throws a lot of stuff at the wall. Regardless of what you think about them or whatever, you know, that's, that's what you're dealing with. So you got, you got to Understand that. I think you stick to your own principles. I think it's really important to have a Plan B. Yeah. Look, on, on, in one paradigm, you know, he's all about winning the press conference, so you throw people at the border, etc. You have to remember, NAFTA, according to him, was the worst trade agreement in history, notwithstanding. When you actually analyzed it, the US had done exceptionally well, as had Canada and Mexico. He renegotiated or had his minions renegotiated. I would say. Never mind. I would say the Wall street journal said 1% or less of NAFTA substantively was changed and now it became the best trade agreement in history.

Right, right.

So history repeats itself. Now we find ourselves where it's the worst trade agreement in history, notwithstanding, he negotiated it and we take advantage. It's just rhetoric and, you know, you got to take it with not even a grain of salt, a salt mine. But having said that, he, he's got a lot of people around him, you know, who have that type of viewpoint about trade, you know, so not about Canada per se, just about trade, if that, if that comes to be. I think we really need a Plan B, you know, where, you know, it's a real sea change. I'm not, I, I give the likelihood of a Plan B a low probability or the necessity of it, but I would have one.

What does that look like? What's Plan B?

Well, somebody pointed out the other day, I think it was Europe, somebody in Europe. Maybe it was Macron or somebody. I can't remember. I read, you know, there are seven and a half billion other people not in the United States. Maybe we should have free trade agreements with the rest of the world. You know, if, if, you know, if he, he's not interested. Right. You know, you look at Canada, you know, we, we have a lot to offer. Now. What it requires is intelligent industrial policy, which, to be fair, I'm not sure we've had much of. There's not a lot of people in our government, at least in elected government, with backgrounds in that. That's not why they run. They didn't run to make Canada an economic powerhouse. Many of them ran because of other issues. So, you know, I think it would be really important to get, you know, have. When you see what some of the European countries have done, Switzerland, the Scandinavian guy, they really get together and figure out what's best for the country. Yes, they disagree over certain social issues, but at least in terms of industrial policy, if I can use that term, they figure out what works for the country, we've never done that. I'll just take one example, lng, which is to me the biggest no brainer in history. And we didn't take advantage of an industrial policy to say look where the world's going, we can be a powerhouse in lng, but it means we need pipelines and we need facilities and we need them on different coasts and areas and we can deal with just about anybody and provide that. But we never did it. And to me that's what we need to correct as an industrial policy, almost regardless of whether the US stops with the Canada's our enemy nonsense.

Right. Okay, good. Appreciate that. Maybe last formal question here. With all your experience, everything we've talked about over the last little bit just now, what would be sort of the number one piece of advice you'd give to whether it's young folks starting a career in finance or whether it's, you know, someone in the middle of their career. Best piece of advice, how to be successful in maybe career, maybe life, maybe they go together and maybe the flip side being anything you wish you had known earlier in your career that would have helped propel you forward?

Well, I give the same advice that I give my two daughters who you know are doing very well in their careers. You know, find something that you love and are passionate about life. You only got one life, right? Why not live it at least on the career part of it doing something you really like and if you don't like it, it's not worth it. And it's a lot easier to be really good or excellent at something that you love than something you don't, that you're indifferent towards or you're ambivalent about. So I think that's really important. I think self knowledge is really important. I remember having one conversation with a fellow, this is way back. Well I guess it would have been early CIBC World Markets former somebody who had been an investment banker. And I was meeting with everybody and saying where do you see yourself? What's your career aspirations, et cetera, et cetera. And this one fellow, he told me what his career aspirations and I remember thinking, you know, the bubble in my head was you got to be kidding, you're terrible at that. So he had no self knowledge. Now you know, I ended up asking him to take on. He did have a lot of good strengths though, so. But it was about fit. So I ended up, you know, asking him to take responsibility in areas that I thought he was really good at notwithstanding. That wasn't what he envisioned himself. Yeah. And he Ended up having an unbelievable career and having very senior positions in the Canadian financial institutions industry. But, you know, if he had just done what he wanted to do, he wouldn't have succeeded because he didn't have the skill set.

Okay, great. Okay, last question. Maybe put you on the spot for a second. We ask everybody that comes on the podcast. You know, our theme over here is unlimited your wealth, unlimited. And we always like to ask just to get to know the person a little bit better. If the world, the world's unlimited, you could do anything you want. You could have done anything you wanted. You can still do anything you want. If you weren't, you know, chairman of, you know, CIBC genuity, you know, outcome, etc. If you could do anything you want or could have, what would you be doing? Or what would have you been doing?

That's a, That's a good question. You know what? I guess my philosophy, and maybe it's about keeping yourself happy, is not to second guess. I, you know, I've had a really good career. Can I say that's the only thing that would have made me happy? No, but, you know, I've really enjoyed it. You know, it's been terrific. I mean, the only area, you know, and fortunately I'm six two, probably six one now as I'm shrinking. Yeah, I played college basketball. You know, in my dream, I would have liked to have been bigger and played in the NBA and then maybe had a career doing that. But, yeah, having said that, I had no aspirations to be involved in professional sports. You know, you get to. In my point of life, social impact investing has been very important to me. That's been a theme of my, A big theme of my angel investing, of actually giving back and, you know, hopefully making money at it as well, but doing something that makes the world a better place. You know, I love basketball or pro sports or some pro sports, but, you know, I don't think that's social impact investing. I think that's entertainment. So, no, I wouldn't want to do my. Have my career only doing that. But as an individual performer, if you will. Yeah, I would have liked, loved to. You know, there's no greater thrill than hitting the winning three or, you know, whatever.

Right.

You know, back in the day. So that, you know, that was, that was always quite thrilling.

Amazing. Well, it sounds like you've hit a lot of winning threes in your career and you've won a bunch of championships as well. So, look, thank you so much for your time. Really appreciate it. Great conversation. And, yeah, wish you all the best and thanks again.

Okay, thanks for having me, Brian.

Okay, bye. Bye.

Bye now. The unlimited podcast is hosted and produced by Brian Gensler and is edited and mixed by myself, David McMillan. This podcast is not to be taken as investment advice. If you like what you heard, don't forget to rate the podcast and follow us on social media at genslerwealth. Thanks for listening and see you next time.