Latest / Unstuck Pod / Help Founders Get Focused (Hugh O'Reilly and Jamie Schneiderman)
Transcript
- Jamie: Hi everyone, welcome to the Unstuck Pod. really excited today to have Hugh O'Reilly here with me. And so wanted to introduce him and then pass it over to Hugh. welcome, and then please could you jump in and let everyone know about you, some of your background, your journey. Love to hear it. Hugh O’Reilly: I look forward to it, Jamie. Jamie: So yeah, so so so like let's start with what have you been do so you've done a lot of interesting things. You've worked in a lot of interesting places. let's talk a little bit first about where you've been. So what kinds of things have you done in the past, and then where is it taking you more recently? and what are you doing? Hugh O’Reilly: Sure. Well, I mean, problem is when you get to be my age, Jamie, like I could I could use suck up all the rest of your time just talking to you about the past. But in any event, started my career ⁓ really in politics. After school, I worked for Bob Ray. ⁓ I worked as chief staff to a cabinet minister. That's how I got into pensions. And then I was on Bay Street for many years, was a partner at Tories. After my wife and I adopted two kids, I decided it'd probably be better if I was at a smaller firm. Nothing slowed down, but I went to a smaller labor side firm, ⁓ started working with jointly governed pension funds, and probably the most prominent ones I worked with were the Hospital of Ontario Pension Plan as well as OP Trust. That led me ⁓ into the president and CEO of OP Trust, which I did for a little over four years. Got to do a lot of things, learn a lot of things about running a an in pension investment fund, a lot of things about innovation in terms of within the organization and also the innovation economy. Because one of my I have to do a shout out to this person, ⁓ of my ⁓ friends from Law Days is a guy named Salil Munjal. He's one of the most creative and interesting ⁓ capitalists in the country. He's now the managing partner. partner of Yale Town Ventures. He got me out, he got me tuned into the the innovation investment world. I was part of the innovation roundtable for the TMX, which issued a report and pointed to the lack of capital in the in the growth equity area. I left OP Trust. I spent some time pondering what the next chapter would be, ⁓ I got active in a couple of think tanks, CD Howe and Global Risk Institute. Got it, stayed ⁓ active in ⁓ innovation becoming the executive director of Innovate Cities, which was a ⁓ smart concept originally, became a data contract con ⁓ trust ⁓ concept. And then I've I work with a number of organizations, charitable not-for-profits on their boards. I'm also on the board of a couple of startups. And I like to provide advice and mentorship to startup entrepreneurs, either formally ⁓ the context of being on a board ⁓ just informally when you come across and you meet these amazing people. Jamie: Right. Hugh O’Reilly: who are active in that part of our economic ecosystem. And I just despair at the po at the fact that not enough is being done to support these people. So how was that for a nutshell? Jamie: No, no, that was great. I I loved it. ⁓ and and I think it's I think it's a very I I think not everybody has has sort of seen both sides of the coin, right? Where they've worked in and around larger organizations, larger scale view of the world, and in your case, government as well. So it's government and big finance and big law and obviously corporations. And then you flip over on the other side. And actually I do want to spend the time understanding and talking through your experiences with ventures in particular. And and so, you know, you mentioned a couple of interesting things, a lack of financing or finance solutions, if like, or or just ⁓ access to for venture. You know, I would go a step further and say that there's just a lack of infrastructure and support in general, a lot of talk and not a lot of ⁓ support for those things. But I I'd love to hear from you who has seen it and who has been part of it and has discussed sort of trying to do it. What are the things you're seeing first there? and and then I again I want to move into some of the advice you're giving to these ⁓ firms, ⁓ venture firms. Hugh O’Reilly: Well, I I what you just talked about in terms of a lack of infrastructure and support, that really resonated with me. And w and you know, too often we think of this infrastructure and support as being something that needs to be a lot more institutionalized. ⁓ And we about it in grand terms, ⁓ but ⁓ my what's needed are some smaller things. ⁓ I think ⁓ people who've been fortunate enough to have had a career like mine need to be prepared and willing and wanting to help out these organizations as they're growing. And things that we can do to help entrepreneurs include there's mentorship, there's talking about our experiences, there's helping with them with the budgets, but there's also most important, bringing them into our networks and introducing them to people. And that's a risk that I I I don't think enough people take where we're prepared to make introductions and you know I could introduce you to someone Jamie and if they don't like you that's not on my that's not on me that's on you and them but I think we have to be prepared to do that. I think we have to be prepared to help out with strategy. entrepreneurs it's like you know it reminds me of my of my first wife Right. She had a lot of reasons why she didn't like me ultimately. But one of the things she didn't like about me is when I would introduce her to w like when we met up with old friends of mine, I'd forget to introduce her and it would bother her. And I did it. And I, you know, I didn't do it on purpose or anything. the I just see an issue with a lot of young entrepreneurs. They, When they think about their tech, they don't necessarily understand that some of the things that they just take as table stakes and no big deal are big deals to those of us who are who are more involved in who've had had more involved in you know kind of regular life. Two examples come to mind. One is around AI. like I'm really lucky. I've met a couple of people. ⁓ Wally Tranholm is one of them. Mae Ma Mavencurve is another. They're incredibly smart people. they've actually identified some of the stuff that corporate world misses out on in terms of AI. And they're a position to develop tech that can bridge that gap. And I think they're going to do it. And by that I mean tech that can where the where the what the AI does, how it operates, what's working, what it make sense? Can you get the AI to monitor itself? All of those things. They think about those things because they're incredible people and they're really smart. And ⁓ know, I I ⁓ I think about AI, ⁓ Bednar, who's someone I've been fortunate enough to meet a couple of times, ⁓ wrote a column in the globe, I'm gonna say, a couple weeks ago. And she talked about people are just willy-nilly implementing AI. They don't and ⁓ don't, first of all, they don't p t understand the AI. Jamie: Mm-hmm. Hugh O’Reilly: Well. Two, they don't understand what the AI is even doing within their organization. And things like data sovereignty and that operates, who's got control of your data, people are necessarily focusing on. So I see but these are the things that when I see young entrepreneurs, they think about this stuff, but they don't necessarily call it out. And sometimes ⁓ I'll call it And sometimes it's because I think I'm embarrassing them because I don't understand. things as fully as I should. I think I told you this story, Jamie, the time we chatted where I was talking to Mai about a particular product she was working on. And I was saying, you know, we should like, I think the trick here is developing a software for this. And she's like, I can get the AI to do that in two days. Whereas two years ago, what I was saying was insightful. Who knows what's going to be insightful two weeks from now? Jamie: Yeah. In in fairness, Hugh, I I would like you to know it's that change that you just described is far less than two years old. So so that is a very, very recent change to to say those things. and I think a lot of companies are behind there. I I I wanted to like so I think y you're making some very interesting points. I I wanted to talk first. So so you talk about introductions, right? Or like networks, right? How do you get people in the networks? ⁓ one of the things that I've always in my experience that I've seen is that ⁓ organizations, ⁓ the the the powers that be, if you like, say we want to help ⁓ stage companies, we want to help tech, and then it's all ⁓ into the it's only about strategy and advice and other things. ⁓ the only comment I would make there is In a lot of cases, the folks that wanna help have no idea what that world is what the world is that they're really walking into, right? Hugh O’Reilly: 100% because an example that I would focus on is you'll have a young entrepreneur starting their business and it's say it does three or four things. And say one or two of them generates revenue at the moment. But the other two things are the dream and the other two things are the disruptor. The problem when you get people like me involved in the business, we want to bear down on where you're making money. Right. Because what investors understand, ⁓ I I I mean investors they're there, they're smart, they do their thing, but the thing they really do is count. They count how many customers and your revenues. And when you're to when you're in an early stage and it's technol technology risk, you need to do more than that. And and you need to also understand that some of this stuff like some it won't work. Jamie: ⁓ for sure. Hugh O’Reilly: But sometimes things that don't work up coming up with better solutions because while you're ⁓ something else isn't while the main thing wasn't working out, there's other things that come along that are the opportunities. Jamie: Yeah. No, ⁓ and listen, I I've had I've I've been in and around investors. I've raised a bunch of money. ⁓ I had an investor that was a little too focused on l you know, looking back at revenue. And by the way, I'm not saying that looking back and the numbers are not relevant. Of course they're relevant, and I think there's a lot of factors around that. I think the real thing that we we need to think about, and you mentioned it is you always have to be thinking about what is the potential here. How are we going to capitalize on the potential? So it's where is it going? And it can't just be about future, future, future. Don't worry about it. I don't mean it like that, but I'm saying it's sometimes you have to ⁓ you know, a lot of times I tell companies and startups, you have to go slow to go fast. So going slow to go fast is get it right. What if you've got it right, if you figured out all the pieces, then scale. There's nothing stopping you from scaling. But if you don't think it through right now. Then you're gonna be in real trouble. And I listen, of the company, almost every company I work with gets to a point where they can't do that. Like where they've ⁓ ahead and now they've hit a wall because they can't figure out how to get to the next step. And so sometimes it's no one wants to hear we have to take a ⁓ minor step back, just think, redo it and move forward. But that's like a ⁓ are mindset things. So here you have these opposing mindsets where you have a venture once go, go, go, go, go, go, go. And bigger organizations that are like, well, where's the revenue? Where are you at right now? And so it's so let me ask you a question. I wanna I wanna understand for how how do you bridge those things, right? One, ⁓ ⁓ if you're bridging them and you say it's about networks and it's about helping them grow, like w how do you prove to companies, I guess, ⁓ on a one-to-one basis, that you're gonna go and deliver those things? Hugh O’Reilly: I think it's hard. I think that's why there's a place for I think a place where venture fund capitalists could perhaps, and this is just coming to mind as we're chatting, Jamie, ⁓ could do more or do better is to understand that to that they need to be an active bridge between the new economy and investment And by being an active bridge, I mean helping those where things are at, explaining how quickly things are going, understanding the incentives and the motivations of the institutional investors. ⁓ problem the one of the big problems you have when you're on an institutional investor ⁓ ⁓ you're managing a big chunk of money, you need to invest a big chunk of money in order to keep the machine going. ⁓ I think it institutional investors need to either come together and develop cooperative models where where they invest as a co-op. So they contribute 10 or 20 million, whatever it is, and then they have a some capital and they can invest into the new economy. I think that the new economy could play, could help institutional investors understand ⁓ they're maybe at risk or where where traditional businesses that they're active in are going to get disrupted. Look at the SAS model. This model may already be dead. Now, even if it is, and and then the other thing I'm hasten point out, even if it is dead, Warren Buffett his business by, I think the description he used to the businesses he bought, the there was the last puff of the cigar where you can make money. So there's lots of last puffs of cigars that are out there. And then the other thing with ⁓ I and the SaaS model is AI can come up with the solutions that some of these organizations have built their business on. Jamie: Yeah. ⁓ yeah. Hugh O’Reilly: And then how do they adjust? And then favorite example I like given, but this really discloses my age. At the turn of the century, now when I was a kid, turn of the century meant you know 1900, but now it means the year 2000. But at the turn of the century, there were a lot of organizations, conglomerates that owned logistics businesses. They were getting out of those businesses. I worked on those transactions. They were getting out of them because they viewed them as buggy whip. Jamie: Yeah. Hugh O’Reilly: businesses. And then what ended up happening is the Internet of Things in particular blew not more than a mere puff of the cigar. They blew life into those businesses. And I think that's the other hard part about understanding where we're at when we're at this, we're at a major, major inflection point. And the level of disruption that's coming is not well understood by anybody. Where and we always, you know, there's that thing about, you know, we We take Filet Mignon technology and we turn it into hamburger. Like we're disrupting. You look at some of the technology disruptions that have occurred. It disrupts the low wage economy, like hospital workers, cab drivers, stuff like that. ⁓ think is going to be very different than that. Very different. And I think organizations that are looking just to, you know, automate their call centers or whatever, okay, but really is that come on. ⁓ You're not you it's like I often think my car is gonna remind me at when I park it that hey, you only use 10% of my computing power, or one one percent. And I, you know, we could be in that world very quickly with AI. And I don't think grasping that from a governance point of view, from how do I implement it as an executive, this is wild. Jamie: Yeah. Well, I felt I I I think ⁓ very interesting when I see and talk to people who are in and around it versus people who are not, and just how big the gap is there in terms of where they think things are at today. gigantic right now. And as you said, think ⁓ you know, this is moving so fast and it's changing s so significantly. It's the inflection point that ⁓ Nobody knows what it's gonna be. ⁓ but yes, there's I I think what's most interesting is we don't know where it's gonna go, but it should create, and I think it's already creating lots of opportunity to bridge, right? And that's where there's a ton of those who can jump on this, take advantage of it, and not just find the the low there's low-hanging fruit, but I think there's real opportunity. You mentioned it ⁓ early on. Hugh O’Reilly: What's funny in conversations I've had this week, you know, there's because I've really intrigued by the in the AI in the legal field. And you, you know, you hear about the horror stories where the AI made up cases and stuff. But then that helped me really understand what AI isn't is and isn't, and then the role of a human. Because when you're when you go out and you start your practice of law. And they you'll often hear people say, Well, I didn't learn this in law school. No, you didn't. You learned how to think. And then you take things to their logical conclusion. So when you think about the AI and where it's made up cases and those sorts of things, that's actually thinking like a lawyer in the sense of it's taken things to its logical conclusion. And where the human role in that is the ability to offer insight. And use experience. Because I I I had a disagreement with ⁓ friends about this this week. I don't think AI is ever going to reach the insight point. But the logical conclusion point, it's there. I don't mean like it will offer insights, it'll monitor things and the rest of it, but when you take when you take it when you take it to the next level, how you articulate taking it to the next level, that's the role for the human. I think. But regardless, I think we need to understand that the way AI operates, it's gonna take everything to its logical conclusion. And those conclusions will demonstrate human beings aren't very logical. Jamie: Huh? Yeah. ⁓ I so so it's funny because you just described the the insight versus logic and my opinion about it. Not to I don't want to we can go down a rabbit hole. We could spend probably hours talking about this, but but for me, the the idea is that the insight is the input, right? Like the it's like the the deep thinking, the challenging the idea, the the the initial input to an AI to AI that needs to come from a different place. And that's what I've seen. AI will then, know, can pull logic and rational ⁓ information all together to then construct that into something. But it but ⁓ in, garbage out, like in a lot of cases. And so prompts or inputs or but but insight is the idea there. Hugh O’Reilly: And the difference between inductive and deductive reasoning. Right? Because 100% believe AI is gonna outperform humans on deductive reasoning. But it's the inductive part. And then when you think about how we're using it ⁓ where do where we're putting the horsepower, like ⁓ on. And then ⁓ I I don't know, corporations seem to be obsessed with call centers, right? Jamie: Yeah, interesting. Totally. Yeah. It's all yeah. No ⁓ yeah. Hugh O’Reilly: Obsessed. So they offshore them. And then you know you have the frustration of dealing with people. It's not their fault, but they don't, English isn't their first language. So as soon as you're off the script, you got a problem. I wonder about that with AI. How quickly do you go off a script? Right? And deductive, inductive, and how you solve for that problem. I think someone who can start working on that, like when to put your hand up. Jamie: Yeah. Interesting. Hugh O’Reilly: Like getting the teaching the AI to put its hand up, so to speak, and to say, okay, I'm at the end of my runway. ⁓ having having an AI capability that can come in and act like a a sentinel. I watched too many of those Matrix and Terminator movies. ⁓ it would act like a sentinel and it would say to the person up the chain, Did you know? Did you know AI is like ⁓ know ⁓ Jamie: Ha ha ha Well, I think you're gonna see I think you're go I think you're starting to see with agents and other things, you're starting to see at least capability that says, Hey, your job is to go and do these things. So it's it's as opposed to ⁓ just input output information. Yeah. So I it's moving there, but if you look at the percentage of companies, especially like that are adopting AI in an in an agent way at this point, it's it's a in it's low. It's really, really low. I mean, we talk about it like it's everywhere, but it really we're not we're barely scratched the surface ⁓ at this point. Hugh O’Reilly: and and I'm not meaning to offend anyone or any organization. There's no way that most organizations understand the ⁓ capabilities, limits, and potential of those things. It's just not how corporate land operates. Sometimes it does, but it's like, you know, why is it being implemented? Well, we're implementing it because everybody else is. ⁓ a big push going on. Jamie: Do it, do it, do it, Hugh. Hugh O’Reilly: It's going to save us money. Generally speaking, actually not a very good skill set of corporations, generally speaking. Like they'll do massive headcount reductions, and when they grow back to prosperity, they hire people back. ⁓ And ⁓ really that shows you how difficult it is to move out of traditional business models ⁓ is one place I would thought that a company could take real advantage of cost savings is remote work. Because if I reduce the space I'm renting, that goes straight to profit and loss. Even that they're struggling with. So then how are you gonna, how is that mindset gonna you fully use the capability of AI, fully understand it, and be able to it, to supervise it, to monitor it, to report on it, to regulatory authorities, to the board, to more senior people. These are big issues. ⁓ wife is arriving. Jamie: Yeah. It's all good. It's all good. It's all good. It's all good. well better the the dog than to you that way. The the the the no I I would say that ⁓ these are Hugh O’Reilly: He's talking to the dog. Jamie: Well, there's so many questions, so many interesting things. Let let me week again, we could go on and I think ⁓ you and I will have to chat again. Let let me let me ask you a ⁓ short question, and then we'll have to wrap up. So your work well ⁓ do your best. ⁓ the the we're all good. We're all good. ⁓ you're working today. So so we ⁓ you know, a lot of the conversations have come from the point of view of large organizations and how they view. Hugh O’Reilly: Does that mean a short answer? Jamie: you're ⁓ you said, I'm advising, I'm working with, I'm trying to help early stage companies. ⁓ What the things that you're finding most there and the places where you're you you think I'm helping the most right now, that you could probably encourage others to to think about if they have it, if they have the capability to do? Hugh O’Reilly: Well, i I think we all like to think this, but I like to think I have a trust relationship with the founders I work with so that they can talk to me about whatever it is that's on their mind. Two, I like to think I help people focus, but I think you also need to need like it's I I I ⁓ been really hard for me to understand is the people who are founders of these companies are incredibly smart, they're incredibly creative, ⁓ Focus isn't necessarily their biggest skill set. And that's that's okay, but you sometimes have to remind them, get them to focus, push them on things. Sometimes they get discouraged pretty easily. And you have to be prepared to listen, to hear it out, and not to be a not to be ridiculously optimistic, but to be helpful and keep pushing them in certain directions. Jamie: Yes. Yeah. I agree. I owe that's the if there's one thing I tell people you're not focused enough and that's one of the things you've got to do. So we agree on that one. And it's very hard when you're in it. You grab whatever you can, you kind of, you know, you're trying to figure it out. and focus is not really a core strength. ⁓ but there comes a time where you have to get into that, otherwise you'll lose it. So I think it's great to have somebody external like you, who can say, you know, you're doing too many things or you're not doing the right things, where are we gonna go first? And I think that's super helpful. so So let me Yeah. Hugh O’Reilly: Last point, it me for interrupting you, Jamie but I also think when you if you're fortunate enough to be put in a ⁓ like I've been by various founders, you also have to bring a humility with you. Right? Because sure there's stuff I know, ⁓ you you don't have that sense of humility and listen and think about it is they're saying and take it to that next step, you're failing those people. Because there's not one founder who's involved me in their organization who's thought, you know, Hugh's gonna know more about AI than me. God help them if they thought that. Or Hugh's gonna help with the coding or Hugh's gonna do this. That's not why I'm there. And you've gotta remember that. And sometimes they chase they chase things that you think and like, why are you doing that? And then it makes sense. So you have to have that kind of you really humility is very important when you're helping people up. And it's hard because they all like Jamie: Mm-hmm. Hugh O’Reilly: the founders I've helped, they treat me like, you know, ⁓ I I'm a member of the royal family sometimes. And you're thinking, like, know, I'm not. ⁓ Jamie: Well, they're doing impressive things. but they're good at what they're good at, and you're good at what you're good at. And like I think these are this is how the two come together, right? ⁓ The of the ⁓ truth the end is the no one gets there alone, right? Everybody needs help. You need help, you need advice, you need other perspectives. Your your point is, well, these founders need my perspective or another, excuse me, another perspective, whether that's yours or somebody else's. But you at the same time can't just go in and say, I have all the answers, which of course you don't think you do. You know that you're hearing another perspective. It's the combination of those things to get to the best possible place. And as long as everybody's willing to listen to each other, mention trust, doesn't mean I'm gonna do everything you say. Trust means I'm gonna listen to you and hear you out properly, because I trust your opinion. Doesn't ⁓ but we can have an open discussion about it. So anyway, I think it's fantastic. I think it's great. ⁓ ⁓ so so so for those who are listening, how people find you, reach you? ⁓ what are the ⁓ where can they get hold of you if they're if they're trying to do that? Hugh O’Reilly: I'm on LinkedIn, which works. they can email me. My email is now I'm going to show that I spent a little bit of time in the military. ⁓ I'll the fanatic alphabet. So it's H is in Hotel, ⁓ is in Mike, B is in Bravo, O'Reilly at gmail.com. Jamie: We will put we'll add some ⁓ links into the ⁓ description so folks can find you. But ⁓ Hugh O’Reilly: And I would also like, I would encourage people to have a look at both Data Asset Store, which is a startup I'm involved with, Land Logic. And my Maven Curve runs a consulting firm called I think I think it's called GPS. And she is incredible. Yeah, so is Wally from all of the people I'm working with, but sh she is a particular talent. Jamie: Awesome. Well, Hugh, thank you so much. I really, really appreciate it. This is great. so thank you for your time, for your insight. So great. and for everybody who's ⁓ listening, watching, thank you for doing so. And ⁓ until next time. Hugh O’Reilly: Thank you, Jamie. It was nice of you to ask me to do this.