How Toufic Boubez Built 5 Startups Without Taking the Top Seat

Transcript

[00:00:00] Toufic: A lot of people go into finding a partner or a co-founder. They look at it a lot more from a number or logic perspective, some skills matrix. I have these skills; I need somebody who completes these skills. That’s really good and important. But for me, what trumps all that is the culture, because I’ve been through it, as you mentioned, a few times, and you’re going to be deep in the trenches with this person. You’re going to argue with this person. You’re going to have big fights with this person. You’re going to deal with really stressful situations, whether from a value perspective or dealing with external circumstances, dealing with people, and so on.

[00:00:39] Intro: Welcome to Signal to Noise by Riviera Partners, the podcast where leading executives share how they cut through the noise and act on what matters most. We go beyond the headlines to explore the pivotal decisions, opportunities, and inflection points that define their careers and shape the future of the companies they lead. It’s time to cut through the noise and get to the signal.

[00:01:00] Eoin: Hi. I’m Eoin O’Toole, managing partner at Riviera Partners. I lead our venture practice here. My teams and I, I think, have now delivered over 700 seed through Series B product and engineering leadership searches over the years, and a further similar number at Series C plus. So a lot of pattern recognition, a lot of experiences learned and shared with founders over the years that we can all learn from today. I’m very grateful to welcome Toufic Boubez to the podcast. Toufic has an incredible background, both as a five-time founder, which means a special kind of insanity, perhaps, as Toufic can tell us all about later on, through to working at some of the largest companies like IBM. He was a senior leader at Splunk. So he’s seen the entire spectrum of company life cycles. And I’m hopeful today that Toufic and I can get into a few topics that add some value to founders. We understand his lens on the world.

[00:01:57] Toufic: Thank you. Thank you for having me.

[00:01:59] Eoin: So, Toufic, there’s a lot of noise, I think, in the market right now, whether that be AI, whether it be macro market signals, or whether it’s the global environment that we’re living in. What are you paying most attention to right now? What are you looking at as noise versus what do you think is a signal out there?

[00:02:18] Toufic: So for me, one of the biggest signals I’m tracking right now is the emergence of MCP, Model Context Protocol. How familiar are you with that? People think of it as another spec, but it’s not just another spec. For me, it is a fundamental shift of how we are going to be working with AI systems moving forward, especially agentic AI systems. This is how we’re extending their capabilities. It enables different tools, agents, LLMs, what have you, to kind of share state and learn from each other and act and collaborate. And to me, that’s what will take AI from where it is right now to the next level. So that’s the biggest signal for me as a biased person in AI being immersed in the AI field. I’m sure there are lots of other really interesting and important things going on in tech right now, but for me, that’s the biggest one.

[00:03:08] Eoin: I’m sorry, just to pause you on that. For those that are less familiar with it, how market-ready is it? Obviously, AI is not a static thing. There’s a lot of future states that we’re anticipating. Where do you think that is in terms of product readiness, market readiness?

[00:03:20] Toufic: It’s market-ready for sure. We’re using it. I know a lot of people are using it. MCP servers are cropping up left and right every day. I spend a lot of time reading every day as part of my job, and I think this is how, kind of, as a leader, you have to be always on top of things. And there’s not a day that goes by without hearing something about some MCP servers or somebody’s enabled another MCP server. And they’re so easy to write now with tools like Copilot, so that’s a real thing. In terms of what am I tuning out so much, but, again, just being, again, very biased, I think there’s a lot of hype around this escalating “war of models” and the primary account. It’s very interesting. But to me, that has become noise now. That’s not the fundamental of how AI is going to evolve. It’s not just adding more parameters. So for me, the real impact is not going to come from just… can we start reasoning? Don’t get me going on the whole spiel about, like, you know, these reasoning models that are not really reasoning models. So that’s the noise for me, this hype around that.

[00:04:26] Eoin: That last piece, maybe we won’t get you going, but you’re right. There’s a lot of conversation. “Are LLMs really AI? How close are we to AGI?” There are dissenters who would say that it’s really just neural network search versus true AI and that we’re still maybe a decade plus away. So maybe a bigger conversation for another day, but there’s a lot of distraction if you want to find it, I think, right now. So…

[00:04:49] Toufic: Agreed.

[00:04:50] Eoin: Flipping just into your own background. I know in the intro, we talked about it, but having been a founder, having been a CTO, having been a CPO, and you’ve been at a variety of scales of companies, from as large as it gets to a two-person startup. Talk to me about when you’re thinking about opportunities that you want to spend your time on, because I know you’re incredibly dedicated when you’re in. You’re all in on what you’re doing. It’s a huge investment for you. What are some of the factors that go through your mind when you’re evaluating any opportunity? And then specifically, how do you think about making this leap to be a co-founder?

[00:05:23] Toufic: For me, at the risk of sounding arrogant, I am at a point in my life and my career where it has to be fun, what I do next is fun and it has to be impactful. So these are, in terms of opportunities, the two major criteria that I use to say, “Hey, is this something that I want to do?” It has to mean something to me and have an impact, and it has to be fun. I hope that doesn’t sound too arrogant. So that’s in terms of the opportunity. In terms of being a co-founder and finding the right co-founder, you’re going to hear me use this word a lot: culture, culture, culture. That’s really the major headline here. So a lot of people go into finding a partner or a co-founder, and they look at it a lot more from a number or logic perspective, some skills matrix. I have these skills; I need somebody who completes the skills. That’s really good and important. But for me, what trumps all that is the culture, because I’ve been through it, as you mentioned, a few times, and you’re going to be deep in the trenches with this person. You’re going to argue with this person. You’re going to have big fights with this person. You’re going to deal with really stressful situations, whether from a value perspective or dealing with external circumstances, dealing with people, and so on. If your values and your cultures are not really, truly in alignment, for me, that’s the recipe for disaster. That’s why I put that above anything else.

[00:06:52] Eoin: Yeah. And you used the word values there. I think that’s super important. If you can understand where the other person is operating from, at least you can trust the intent and what’s behind that, and then you can usually figure it out from there. Right?

[00:07:04] Toufic: Exactly. It’s 100%.

[00:07:06] Eoin: Talk to me about how important the 360-degree view of that human is as opposed to just the work context, especially at your stage now. What is affecting your co-founder isn’t to do with what’s going on at the company, it’s home and it’s other stressors and things like that. Like, how do you even think about vetting for that in a courtship process?

[00:07:24] Toufic: It comes… I’m going to use another word that I’m going to use frequently, which is trust. Right? So in conversations with this person, you have to judge, kind of, the level of trust. We always talk about high trust. As a matter of fact, I don’t know if I may, as a side, the way Boris and I met and we kind of clicked. My current co-founder at cat.io, at our first meeting, we both brought the same thing, which was incredible. I said, “Hey, do you know Simon Sinek?” And he says, “Yeah, I have this video.” I’m like, “Are we talking about the same video? I was going to show you this video.” And there’s this video of Simon Sinek on YouTube that talks about how the SEAL teams choose people for their teams. I don’t know if you’ve heard it, which is high competence and high trust. And high trust trumps everything else. And so we both, Boris and I, approached where we were going to bring that to the table and discuss that in terms of that. That’s a big indicator for me. But, of course, you have to be in tune with this person’s life. They have a life outside of work, and that affects everything else. And that’s an important aspect for me to get to know each other on a regular basis. I don’t know if we’re… we’re kind of, at some point, we’ll talk about remote organizations or remote work and things like that, but if we do talk about it, that’s actually comes into play. So we are a remote organization by choice, and we can talk about that a little later. But I want to bring in the personal aspect of that. Because we are remote, we make a point to know what’s going on in each other’s lives on a regular basis, and so on. And we have a lot of in-person meetings to kind of facilitate that. And that’s really, really important to building trust and building teams, for sure.

[00:09:03] Eoin: Fantastic. No. I appreciate that. And I have seen the same Simon Sinek video, by the way. And like I said, if you have low competence but high trust, they would take you as a teammate over a low trust, high competence person, which I think is crucial. So I’d like… you two spent quite a bit of time getting to know one another before making this jump. Right? This wasn’t a standard interview process of three to five rounds and then asking formal questions back and forth. Right? There was more to it?

[00:09:29] Toufic: Of course. As I said, I hate war terminology, but in essence, you go into battle with this person for the next several years, hopefully, for good and bad, especially for the bad. It’s easy to be friends when times are good.

[00:09:41] Eoin: Let’s talk about that a little bit because I think conflict is often an avoided topic. It’s an inevitable necessity, I think, for the survival of an early-stage company that you disagree. And while you touched on earlier, some founders will hire for complementary skill sets, a lot of folks tend to hire in their image and likeness and look for people who agree with them. So what does conflict look like at cat.io with you and Boris? How do you resolve it? What form does it take?

[00:10:06] Toufic: I win every time. That’s how we resolve it. Neither of us are conflict-avoidant. We actually talk about it. We make sure to bring everything out on the table. So just between the two co-founders, for example, we have had conflict, surprise, right? We have disagreed on things and we have gone into a room, a virtual room, and closed the door and said, “Hey, let’s talk it through.” And we have talked it through. We’ve disagreed, and then come to a resolution either one way or another, figuring out a way through it. Every single time we have managed to do that, and that’s an important factor. Another area now goes beyond the co-founders when it goes to the team. A habit that we have, that I’m very, very particular about, is having a retrospective every two weeks. And the whole team gets together and we go not just over the sprint, we actually surface out really, really sometimes awkward situations. “How are we going to resolve that now, and how will we resolve or avoid this kind of issue in the future?” And we’ve had some uncomfortable meetings where it didn’t quite get personal, but it was to that level of, “Look, this is not working for us. How are we going to fix that?” And we resolve it, and we’re much, much better for it as a team.

[00:11:25] Eoin: Yeah. I think at times of conflict, particularly in early-stage companies, you see a lot of people in the team, co-founders often, will leave or be exited from a company because they deem conflict as not a culture fit, where the reality is it’s either a gap in communication, a lack of curiosity somewhere, or just a need to disagree and commit. And that conflict should be, I think, celebrated and rewarded, which it sounds like it is in your culture, because it’s necessary to sharpen the knife, I think.

[00:11:50] Toufic: Absolutely. I mean, sorry, if I may just in everybody’s personal life, I don’t want to presume. I’m married, and we’ve been married for a very, very long time, my wife and I, and we still have conflict. I sometimes worry about people who don’t have conflict anywhere. It’s like, “What’s going on here?” Anyway, I don’t know if I should be saying things like that, but you know…

[00:12:11] Eoin: Yeah. No. I hear you on that. Yeah. For sure. Turning that into just more specifics about cat.io, I know, obviously, when you first met Boris, there was a set of ideas and concepts that were in place in an initial strategy and direction. You’ve made some pivots along those ways and some shifts. So give me a sense of how what it started like, what it’s looking like today, how you made some of those decisions, particularly interested in some of the approach to the technical decision-making that needed to happen to get the platform to evolve the way it has.

[00:12:39] Toufic: I think the first thing is to accept that whatever you set up, whatever you think about in the early days is going to change. I always use the analogy, and if you have anybody from my team on this call, they will roll their eyes, but I always use the analogy of the cone of uncertainty. Going into the future, the cone of uncertainty widens and widens going to the future. So you might have some things that you decide on upfront, but you have to accept that things are going to change. That’s the first thing. From a cat.io perspective, the initial problem that we’re trying to solve hasn’t changed. That is fundamental, and that is the impactful thing that we’re trying to solve. Of course, we had Canva designs and Figma designs early on, and we had an approach to the architecture early on. And as we evolved and we started talking to people and we started actually doing the implementation, we’ve had to change some technical foundations of things. On the technical side, we’ve gone against the grain to a certain extent early on, which paid off really well for us. For example, we were the first ones to start building actual multi-agent systems, agentic systems, when it was even before it started being a buzzword, to the point that when we were building it, we didn’t have frameworks like LandGraph or AutoGen or anything like that, so we had to build our own. So this kind of thinking… so this which brings me actually to a fundamental principle that we have as a company that we talk about all the time, which is principled thinking. We approach every problem with this thing about principled thinking. What is the problem? What are potential solutions? Can we research them? Can we actually go and find a solution for them? And then ratifying that. And we have also this concept of collective decision-making where we ratify these designs. So we have a process, kind of like the RACE process, that we go through. So that’s on the technical side. On the approach to customers, again, that has evolved too. We came out with a particular thesis about who our RCPs are, and then we went to the market and we started talking, and then that has evolved. That has narrowed to a certain extent. In a way, it turns out there is a sweet, sweet spot that we need to focus on, and so we’re putting all our efforts into that. So again, I think in a startup, especially in an early-stage startup, you just have to accept that change is going to be happening all the time, and you have to be able to embrace it. And you can’t be really, really too tied to your solutions. I come from a Bayesian… Bayes’ theorem rules, runs my life, even in personal life, which is an oversimplification. But in essence, you get new information that changes the outlook. Then you move. You get new information that changes your outlook. Bayes’ theorem rules everything for me, and that’s an approach that we have in the company too.

[00:15:30] Eoin: Must make, as the CTO, building a technical architecture that can both be robust and provide room for all of that ambiguity, it’s got to be a difficult set of trade-offs. So how do you think about architecting for the cone of uncertainty?

[00:15:43] Toufic: I think it goes back to what I said earlier, which is you have to accept that you will have to change things. So I think these are just best practices. Try to avoid hard-coding stuff as much as possible. Decouple things from each other. Use configuration instead of code as much as possible. There’s a lot of best practices that have evolved over the years that allow you to change things when you need to and be able to pull something out and replace it with something else or change direction to a certain extent without having a huge impact on the rest of the organization. I mean, I can go on and on. There’s… it’s a well-established set of best practices for sure. I think, fundamentally, you have to be accepting that things are going to change and think about it early on.

[00:16:26] Eoin: Has AI fundamentally changed any of those best practices and rules that we’ve seen out there?

[00:16:30] Toufic: 100%. AI has changed a lot of things on many levels. Code generation, for example, has been a big thing for us, like Copilots. So for example, the way we were doing one of the first things that the cat.io platform needs to do in order to give you good recommendations is it needs to integrate with your system so we can know what you have deployed, all kinds of stuff. When we first started, we were thinking very, very differently about those integrations, how difficult and how many of them are we going to do. And now with AI, we can churn out these integrations very, very quickly. We changed our approach to our architecture and also to the evolution of the roadmap. Right? So that’s an important thing. The other important thing that I think, and actually I wrote an article about it just a couple of weeks ago, that’s on LinkedIn, and on our website on the blogs. I wrote a blog about it, which is AI has gone from being an external system that you call to being an integral part of your stack, just like your data layer or your database or your messaging subsystem. You also have your LLM or your AI layer, at least for AI-forward companies like us.

[00:17:41] Eoin: So that’s probably a good segue to talk about how that impacts how you think about hiring and the team. I think it used to be that you needed certain types of engineers for certain types of tasks and points on the journey. AI and Copilot are making greater efficiencies. How do you think about hiring engineering and the scale of an engineering org today versus, say, ten years ago when you were in a similar role?

[00:18:04] Toufic: Speaking since we’re still on the AI topic, the engineers that I hire right now need to have good exposure to AI, and they need to be using Copilot, Cursor, or whatever. The coding test that we give, you will not be able to pass it if you’re not using some kind of Copilot. There’s a disqualification right there. Now, I know there are a lot of people that talk about Copilots replacing engineers. I don’t find that as true. I find… I’m a big anime guy, so I don’t know if that goes well with the audience. I think of the Copilots as a mech. You just go in, and it multiplies your skills more than anything else, but you still need to guide it. So that’s to me how I view AI and Copilot. So when I’m hiring engineers right now, whereas maybe a few years ago, people would think of using some kind of external tools as cheating, you know, LeetCode and cheat codes and all kinds of stuff, and you would look for that. “Oh, he’s cheating on the coding test,” or “she’s cheating on the coding test.” Right now, it’s like, “No. No. You’re not cheating? Okay. Well, sorry, you’re not good enough then.

[00:19:13] Eoin:It’s quite a turnaround. Another topic for another day, but I think the same thing is going to be true in the education system over the next decade and how you maximize leverage as opposed to avoid it, and it’s an interesting new frontier.

[00:19:25] Toufic: There are pitfalls that we have to be careful of. And, again, you’re right. That’s another topic for another conversation, but you have to be very careful of the pitfalls. But if you avoid the pitfalls, there’s… it’s a huge multiplier.

[00:19:38] Eoin: Absolutely. You know, the patterns historically for early-stage companies, there were quite discrete windows of “zero to one,” “one to three,” “three to ten,” “ten to twenty,” “twenty to fifty,” “fifty to a hundred.” And they were often viewed as “horses for courses” at points in that journey. I think to your point about being able to accelerate integrations, accelerate code, the velocity at which you can ship, are you seeing those windows compress and therefore it’s changing the type of talent you need that can go “zero to twenty,” for example?

[00:20:07] Toufic: I think the windows are compressed time-wise, but I don’t think the talent compresses at the same scale or at the same rate. I don’t know that you will find people that will go “zero to twenty.” I could be wrong, of course. It’s just personal opinions here.

[00:20:21] Eoin: I tend to agree, but yeah, yes.

[00:20:22] Toufic: I think the “zero to one” has gone from maybe, I’m just using numbers out of thin air, but you know, maybe from two years to maybe one year. But you can still find people who go from “zero to one” and “one to three” and so on, the same people, but “zero to twenty” is going to be really, really hard to find. They’re rare unicorns. If you find them, that’s great. But I think the time scale has compressed.

[00:20:43] Eoin: You’ve done this founder journey now multiple times over. What are some of those signals you’re looking for as to whether you need to evolve your team or somebody is starting to break on that continuum about their ability to continue to scale with the company? If you have signals or signs, I’d love to understand those.

[00:20:59] Toufic: There are quite a few signs that you can think of. The first sign is when the leadership team starts getting overwhelmed. That’s when you need to start layering in specialized leadership, proactively, hopefully, but also intentionally. So another flag for me is when I start spending more time on process than actually moving the business forward. That’s a strong cue for me that the organization has outgrown its current structure, and you need to start looking. I hear stories how Jensen Huang of NVIDIA has, like, dozens, I think, I don’t know, of direct reports. I personally don’t buy into that, for example. If you have too many people reporting to you, I think they’re being underserved. The service to them and the service to the I don’t mean to tell Jensen what to do, but as for me, that’s time to bring in the next layer. But so that’s kind of from the structural perspective. The other thing is when the company shifts phases from, like, building to scale, to product-market fit, to go-to-market, and so on. These are specific transitions that I’ve lived, that you live through, and then you need to bring in leaders who specialize. We talked earlier about “zero to one,” “one to three.” You do need leaders to come and specialize at that stage. You can’t brute force your way through it. Example, like for us at cat.io, we just recently hit that moment on the go-to-market side. From the beginning, it was founder-led sales, which you expect at an early-stage company. We’ve been doing all the selling, all that kind of stuff, but we are now clearly past our PMF. And we needed to bring in somebody who’s just going to focus on the go-to-market part. So we just brought in a seasoned go-to-market executive who just started just a few days ago, as a matter of fact, because now we’re in that phase. So you have to look for these kind of cues and signals, whether it’s organizational or process or phase of the company, and bring in the right leadership at the right time.

[00:22:58] Eoin: I think stage relevance is very overlooked often, and I think either there can be the same fundamental skill set, but what needs to be applied and fully agreed. You know, typically up to about 3 million in revenue, you can brute force your way there and you still may not have product-market fit. And you can convince yourself you do, but when you’re going from three to ten, it has to be repeatable, scalable processes, and you need someone that knows how to run that. Completely different. Yeah. Fantastic. I had a presentation I did recently with Rene, who is the founder of build.com, taking that company to great success over the years. We talked about both the founder to CEO transition for some founders. But just for anybody who’s wearing that founder title, when are you wearing your CTO hat? When are you wearing your founder hat? And do you look at those as discrete responsibilities?

[00:23:40] Toufic: I do. This might be controversial, but I do. As a CTO, I’m really, really focused on the technology, the product, the team, optimizations, all that kind of stuff. And as a founder, I’m focused maybe a little bit more on kind of the health of the company, the health of the business, fundraising, and from time to time, those two things clash in a certain way, and that’s why I’m like, I go to Boris. I’m going to take my co-founder hat off, Boris, and put my CTO hat on, and you’re going to be the… the founder. Let’s have that discussion.

[00:24:18] Eoin: Yeah. It’s interesting for solo founders how to go about getting that same thing. I think that’s where choice of investors, boards, advisors that you can trust in those conversations, but that’s hard because it’s a head and a heart element to it. Right? So…

[00:24:30] Toufic: Oh, yeah. Really hard. Yeah. And I, and I love having co-founders. Every one of my startups, and I’ve had several as you mentioned, I’ve had co-founders. I think it’s hard to do the journey on your own.

[00:24:40] Eoin: I tried it. I had… I can tell you for a while. Then I brought in a co-founder later.

[00:24:44] Toufic: And good for you. I mean, I… I admire people who managed to do that. I really sincerely do. It’s really hard. I couldn’t do it.

[00:24:50] Eoin: I’d say I did it really poorly. So yeah. But, uh, no. It helps when I got the co-founder. Lesson learned. Transitioning then, you touched earlier on the fact that you are a remote company. I know that was an intentional choice early, and it’s part of your identity. We’re seeing lots of disparity across the market based on geo, based on role type, about the appetite to be in office or remote. What made you make that choice, and what are some of the structures you use to make that work?

[00:25:17] Toufic: The first one was that Boris and I are… we’re on different coasts. So that factor by itself makes it relevant. So from day one, we were distributed when we started building the team, building product. But more importantly for me, the data is pretty clear. People might disagree with it, but when it’s done right, remote teams are happier and they’re more productive. And for us, it’s also a strategic advantage because going remote opens up a much broader talent pool, and also it gives us a competitive advantage to companies who are not remote, who insist on return to office. So it lets us hire the best people wherever they are. We have people in Vancouver, in Toronto, in New York, in Philly, in New Zealand. It opens up the world for us to get the best talent, the best-matching talent that we can get. Now, how do you make it work? We rely on constant communication. We have a shared virtual office, which is… has been a game changer for us. Kumospace, if I may plug it. We’re not getting paid by them. We use them a lot. It keeps us connected in real time. So we have virtual offices. I can go knock on Boris’s door or on anybody else’s door and say, “Hey, can I chat with you about something?” even though I’m in Vancouver and they happen to be in New York. That’s a big deal. The other thing is that we have every Friday, we get together Friday afternoon, just for a little happy hour and chat and whatever. Constant communication. We have AMAs every week. I mentioned the retrospectives that we do every other week, and then once a quarter, we bring the whole team together in person. We pick a really cool location, and we just get together for a whole week, and we just bond. We work hard, we play hard. We just bond. So it’s been an incredible experience for us. It’s been really, really good, and I, honestly, I wouldn’t do it any other way right now.

[00:27:09] Eoin: It can be a false positive to have people in the office that you assume there’s communication happening that doesn’t have the level of intentionality that you’re describing that ensures that great communication is happening. Right? I think it’s a huge check-in the box.

[00:27:23] Toufic: Bingo. Actually, that’s an excellent point that you make. Yes. For sure. The intentionality. You’re absolutely right. That’s a great point. Having intentional, great communications because we are remote.

[00:27:35] Eoin: Fantastic. When it comes to then decision-making, it sounds like you all can be on the same page. You can take action and move forward faster. Because I know that’s one of the other critiques is that decisions are getting made in islands and in silos, but it sounds like you’re mitigating that fantastically well. So…

[00:27:49] Toufic: Again, intentionally. I love that word. I’m going to start using it more often.

[00:27:52] Eoin:. And so for you as a leader, something I know I personally have struggled with and I’ve witnessed many around in the world of tech, as an organization evolves, your leadership style has to evolve. As teams grow, there are different types of needs to be met. Do you have a whether a framework or a philosophy on leadership and how you continue to kind of meet the needs of an organization as it’s changing under your feet?

[00:28:16] Toufic: I don’t necessarily have a framework for the growth aspect of it. For me, it’s more about, I promise you I would use that term more often, is about maintaining the culture and the trust. And so even as you grow, the leadership style doesn’t really change and should not change, really. People should expect the same thing whether they are used to be reporting directly to you when you’re like a five-person company or whether now there’s a couple layers between you and them. Like, when I was at Splunk, it was a huge organization with multiple layers reporting to me, and still people felt free to come and talk to me directly. And that level of trust is really… that should not change. But I don’t have an actual framework, sorry to disappoint you on that level.

[00:29:02] Eoin: But it sounds like consistency breeds trust, which then leads to ultimately how people can anticipate what to expect from you in whatever environment. So that’s great.

[00:29:11] Toufic: Exactly. You put it in a better way than I did. Thank you.

[00:29:13] Eoin: Excellent. To turn it then to the other side of that coin, right, there are a lot of difficult decisions to be made early in a startup’s life, at all points, arguably. But, you know, particularly, we talked about architecture. You talk about things like remote versus on-site, but there are also decisions around potentially dealing with challenges based on, you know, performance or personnel. In that whole spectrum, can you give us an example? And it doesn’t have to be from cat.io, but a particularly difficult decision that you’ve had to make, how you came to that decision, how you reconciled with it thereafter, and whether you think it was ultimately the right thing for the company.

[00:29:47] Toufic: I think the hardest decision for me as a leader and as a CTO and as a co-founder is letting somebody go. And mainly because the way I build the team is based on this kind of vetting of trust and culture. Sooner or later, especially in large organizations, I hate to use that term, I can’t, on the spot, I can’t find a better term, but somebody slips through, for lack of a better term. I apologize. And then so the question is, how do you deal with that? That’s typically for me has been the hardest thing. So you have to do it humanely, and you have to do it with respect, but you have to do it. You have to do it as soon as you see it. And that’s the other important thing is, there’s the adage, like, “hire slow and fire fast.” That’s actually a really important part is that you cannot let these things linger.

[00:30:36] Eoin: I think you see it a lot where there’s founders operate from a place of fear because they fear somebody has this institutional knowledge or there’ll be a cultural ripple, but never have I met somebody who let somebody go who thought, “I shouldn’t have done that sooner.” You know? And then so, and then it’s particularly, I think, acute at an early stage because, yes, they’re buying into the products, the company, but really at an early stage, they’re buying into you. And if you’ve brought them on under your name and said, “trust me,” and then you have to turn around and let them go, hopefully, you’ve built through values, through trust, the understanding that they know that you’re doing that for the best of the business and hopefully for the individual, right? I think. So it does feed back to that leadership style.

[00:31:12] Toufic: And actually, that leads into another concept that I have. I don’t know if that’s a framework or because you asked me earlier. But for me, I’m a big believer in self-organizing, self-healing teams. So I guess you could call it a contrarian. Things that I do is that I don’t really give a lot of credence to individual OKRs, as an example. My teams get scored on a team level, a team basis. You sink or you swim as a team. So when somebody in the team is not pulling their weight or performing, that easily self-corrects, or there’s a consensus among the team that, “Look, this person does not fit with our team,” and that makes the decision a lot easier to let that person go. We’re going to talk a lot more about that, you know, that’s actually one of my pet peeves about individual OKRs, but maybe yet an… yet another topic for another conversation.

[00:32:03] Eoin: It’s fascinating because there’s also the “80/20 rule,” right, where, you know, 20% of your team are delivering 80% of the value. And I think in a construct like you’re describing, the bottom 20% that are driving the least are become a little bit more self-evident, and there’ll be less of an appetite for those high performers to keep dragging that weight along, right, and to sharpen the org.

[00:32:20] Toufic: Absolutely. Because having the individual stuff, even in the best-meaning teams and best intentions, fosters a little bit of that competition that is unhealthy sometimes on a team. Yeah.

[00:32:34] Eoin: I was going to say it’s a fine line between healthy culture that self-corrects and self-heals and that turning toxic, I think, pretty quickly and people pointing fingers left and right as well. So I think you have to have a lot of buy-in, I would assume there. So we’ll just add maybe two or three more questions if you’re good. One that I saw on here that I thought was good was just, and I struggle to answer it myself, “In one word, what does great leadership mean to you?”

[00:32:57] Toufic: That’s an easy one. Integrity. Integrity, without it, nothing else holds up. Vision, strategy, all that kind of stuff. You know, if you don’t have integrity, you don’t have the trust of your team. You don’t have the trust of your team. That train’s going to get off the rails. Ask me another one. That’s an easy one.

[00:33:15] Eoin: I’ll ask you one I asked a group of product leaders recently. It’s a bit of an off-the-cuff one. But in a high-stakes, high-pressure moment within the company, picture everybody sitting in the room and you enter. What theme music, what genre of music accompanies you as you walk into the room? What’s that energy that you bring?

[00:33:32] Toufic: I have the music. Probably Ska. A high-energy, sense-of-humor type of person, you know, snappy, making jokes. I think I’d be a good question to ask my team. Yeah.

[00:33:49] Eoin: Your team says it’s the Jaws theme song.

[00:33:56] Toufic: Or like the old… Yeah. Yeah. Yeah. “Oh, he’s here. He’s here. He’s here.”

[00:33:59] Eoin: You know? Yeah. No. I like that. That’s fantastic. You have lots of great answers on that one. I think yours… that’s a great one. I can, when you said it, I can immediately kind of picture your energy in the room. And like you say, you’re making things happen and moving it around, but it’s light and it’s upbeat, and there’s a tempo to it. Yeah. Right. Awesome. Very good.

[00:34:14] Toufic: Thank you.

[00:34:15] Eoin: Excellent. Maybe last question then for you. If you had one piece of advice to other founders, you’ve been through this gauntlet many times, what’s that one piece you would give them?

[00:34:26] Toufic: So many pieces of advice. Can I get two, maybe? Sure. Forget the hype. Build your company for resilience. Don’t follow the shiny object and the hype. Just, I use that term, you know, “don’t half-ass a bunch of things, just full-ass a much smaller number of things or maybe one thing.” So that… that’s the first thing, don’t have that. And the other one, there’s a big operating principle for me, which is “Culture eats strategy for breakfast any day.” I think Peter Drucker said it, but that is such an underrated and operating principle. So just keep that in mind as a founder. It has gotten me through so much over the past twenty years of startups.

[00:35:04] Eoin: I’ve lived that too. I’ve hired for skill and whiffed on culture and been sorely disappointed, and then I’ve hired on culture and values and trained on skill and never been disappointed. It saves you a lot of heartache.

[00:35:14] Toufic: Skills can be acquired.

[00:35:16] Eoin: Absolutely. Well, first of all, thank you, Toufic. This was incredibly helpful. Like I said at the top here, I’ve done a lot of work with early-stage founders, and finding people who know how to cut through the noise to get to the signal like you do is rarer than you would think, and I think there’s a lot… I think your team can be lucky to have you. So really appreciate it.

[00:35:34] Toufic: Thank you so much.

[00:35:35] Eoin: I think that wraps up the episode for today, and check out what Toufic and the team at cat.io are doing. I think there’s a lot of great to be had there as well.

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