
Unicorn Leaders · 2026-02-19 · 1h 8m
Samuel Witherspoon's journey reveals how a small Ottawa team of 30 people outmaneuvered defense giants like Palantir, Lockheed Martin, and Raytheon by understanding an industry still operating with 1990s analog processes. After starting as a lawyer who clerked at the federal court, Witherspoon noticed massive inefficiencies in data management - courts still relied on banker's boxes of paper and manual scheduling with drafting boards. He initially tried solving this through online divorce services, which he abandoned due to lack of purpose. The real opportunity emerged during professional services contracts for the Canadian Armed Forces and U.S. Special Operations Command, where Witherspoon and co-founder Bennett observed employees stuck with Word, PowerPoint, and Excel managing complex defense workflows. Rather than competing directly with entrenched contractors, Anvil positioned itself as a purpose-driven software alternative addressing real analog problems in military operations. The company survived the feast-and-famine cycles of government contracting through disciplined capital management, employee-first hiring (avoiding independent contractors), and a deliberate values exercise that meant saying no to lucrative non-defense clients. Today, Anvil software runs on active military operations and holds official partnership status with Canadian Armed Forces agencies - a testament to persistence through incremental growth rather than explosive disruption.
While clerking at the federal court, Witherspoon observed massive inefficiencies in data management - courts relied on banker's boxes of paper with no search functionality and manual court scheduling with drafting boards. This insight into analog processes in large organizations became the foundation for identifying similar problems in the Canadian Armed Forces and defense sector.
After about a year and a half selling online divorces, Witherspoon felt no mission or purpose behind the work and was ashamed to tell people what he did. He concluded that without underlying purpose and care for the mission, he wouldn't persist through difficulties, so he and his co-founders decided to pivot.
Anvil won Built in Canada Innovation Program (BCIP) challenges for the Public Health Agency of Canada's vaccine screening and disease monitoring work around 2016, which provided credibility to then bid on a U.S. Special Operations Command project - their first defense-focused contract that became the springboard for Canadian Armed Forces work in 2017.
Anvil managed cash conservatively by saving during profitable periods and spending strategically during lean times, while also uniquely hiring only employees rather than independent contractors. Co-founders including Bennett sometimes forewent salaries to maintain payroll and avoid the volatility most consulting firms manage through contractor models.
Observing that the Canadian Armed Forces and defense organizations still managed complex workflows using Word, PowerPoint, and Excel - replicating analog paper processes digitally - Witherspoon and Bennett realized there was a massive software opportunity. A pivotal values exercise forced them to say no to profitable non-defense clients and commit fully to building product in the defense space.
Computed from the transcript - who did the talking, and the words that came up most.
Samuel Witherspoon was a lawyer who walked away from a safe career to co-found a tech company. The first thing he built? A platform for selling divorces online. He was ashamed to tell people what he did for a living. So he sat in a boardroom with his co-founders and asked a dangerous question: what if we burned it all down and started over? That question launched a 12-year grind into one of the most guarded industries on Earth - Canadian defense intelligence. Someone told Sam that no one ever makes the transition from services to product, especially selling into government. His response? "Watch me." Today, Anvil's software runs on active military operations. Their unofficial company patch is a cockroach. The motto: Hard to Kill. In this episode, Samuel shares how a team of 30 competes against billion-dollar American defense contractors, why Canada's sovereignty moment is opening doors that didn't exist two years ago, and what it really takes to outlast giants when you can't outspend them.
Transcribed and scored by The B2B Podcast Index.
Speaker A: It is. It's a constant failing on my part to not, like, end that soon enough. And the harm that, like, you are not aware is being caused elsewhere in the team is, Is almost inevitably more significant than you're giving it credit for. And so I think the biggest challenge I've always had is, like, the second bad behavior starts to materialize, number one, like, correct it. If they don't accept the correction, that's pretty much the end of the relationship.
Speaker B: There's a moment a Sam Witherspoon can't shake. He's sitting in a boardroom with his co founders, and they've been selling divorces online for a year and a half. He started as a lawyer. The business was working and money was coming in. But Sam, um, was miserable. I was ashamed to tell people what I did for a living. He told me. No mission, no purpose, just transactions. So in that boardroom, co founders looked at each other across the table and asked a very dangerous question. What if we burned it all down and started over? Here's what makes Sam's story worth your next hour. That moment of walking away from a working business was just the beginning, because the thing he chose to build next, a defense intelligence platform called Anvil, put him directly in the crosshairs of the largest American defense contractors on Earth, whether it be Palantir, Lockheed, Rython, these companies with thousands of employees and billions in government contracts. Sam had about 30 people and a belief that the entire defense establishment here in Canada was still solving problems the way a 1990s law firm did. Bankers box, uh, full of paper that no one could search. Perhaps Excel sheets that were still outdated. And someone once told him, nah, uh, no one ever makes the transition from services to product and selling into government.
Speaker A: Jeez.
Speaker B: His response? Watch me. Today, Anvil software runs on active military operations. Their unofficial company patch a cockroach. The motto underneath, hard to kill. They are official partners with many the Canadian armed forces agencies. In this conversation is about what it takes to outlast giants. Why sometimes the only way forward is to stop playing their game entirely. Sam, um, welcome to our, uh, David versus Goliath podcast. I'm excited to, excited to have this story. I'm excited this story because it's a homegrown story here in Ottawa. I'm excited because, Sam, you and I have done some work together and we've become some good friends over the last little while. So I feel like I'm. I've got a backdoor insight to some of the crazy shit that you've had to actually try and do as an entrepreneur. Um, and I'm excited to tell your story in both this book that we're writing and in this podcast, because I truly believe it as one of the perfect cases of a David versus Goliath. A small little Ottawa team of engineers and hackers who are trying to figure their way out in this defense industry, you know, go through this crazy journey of professional services to productization, different team members and different people who are coming to it. So, Sam, tell me where this, where this starts for you in terms of how you got into this space, into the defense space, into, uh, data analytics and software.
Speaker A: Yeah, you, uh, you sort of keyed in on it, which is, I've been wrong a lot. And I think what's drawn me back into this industry is the. Is the sort of, like, mission and purpose component of it. So about 12 years ago, I clerked at the federal court. And while I was there, I experienced, you know, sort of firsthand the challenges of, you know, fragmented data ecosystems in their circumstance. It was frankly, you know, huge piles and piles of banker's boxes full of paper. And the bigger the case, the more complex the case, basically, the more paper you were forced to sift through. When it's paper, there's no control f. There's no way to sort of speed through that process in any way. And so you end up wasting a ton of time with those, uh, paper copies. So the original premise, when I left my clerkship, completed my articling position at the court, joined practice, was, is there an opportunity to start something to solve that problem? And so tried that for about a year. Sort of realized pretty quickly that the government of Canada does not work with people with great ideas, uh, all the time. And so we looked around and said, like, well, where could we sort of inject ourselves in that process, sort of front run the court and, and take over a huge volume off of their plate and then use that as the bargaining chip, as the sort of, like, negotiating point to, to inject ourselves into solving that problem for them. And so family law was a. Was a very logical, logical point of entry. There's a huge amount of family law cases every year. The court is involved in many, many of them, unfortunately. And there's a population of desperate individuals who can't afford a lawyer in that circumstance. So we worked away at that for maybe like a year and a half. And in the course of doing that, I'll be like, brutally honest, I did not like the work I was doing. I was ashamed. Tell people about what I did.
Speaker B: You were, you're selling, what was the line you were selling? Divorces online.
Speaker A: Yeah, I was singing divorces online. Yeah. It was not good. It felt purposeless to me. It was, you know, there, there wasn't a, ah, There wasn't a mission behind it.
Speaker B: But the key insight, the key insight that drove it was, can I control f this box of paper?
Speaker A: Yeah, yeah. How can I get through like huge volumes of information quickly.
Speaker B: Yeah.
Speaker A: And, and more effectively or efficiently that than I previously was. And so, you know, to do that we sort of.
Speaker B: That's, that's interesting because, because that insight you had to be in the industry because, because you would assume like, well, you can. I can control off my own files. Right. Like as a individual or like. But I guess you're looking at legal systems, governments, you're looking at more archaic data management that has not evolved.
Speaker A: Yeah, yeah. And I think the, the other challenge that, you know, any large organization has, it's not just the government of Canada, it's, it's any large organization is that at that size and scale change is very complicated and very cumbersome. And so, you know, the sort of tyranny of the status quo for them is, is always present. It's like, well, it's, you know, this is how we've always done it. It's easier this way. We know how this system works. I remember, uh, one of the first weeks I was at the court, I walked in, I was introduced to the court scheduler and I walked into her office and she had a giant drafting board and you know, there were 30 something judges at the time on the federal court. Each, each one had a line, she had a giant ruler and she managed the entire court schedule in her weird little like, paper format with like special codes so that she could remember what was what. But like if she got hit by a bus tomorrow, like the court schedule would, would come crashing down. I remember thinking to myself, like, yo, there's calendar apps.
Speaker B: There's things that have solved this already. Solved. This is a solved problem.
Speaker A: Yeah, but, but you know, she'd been doing it this way for 30 years. She was really good at it. Like, you know, there was never an issue. And so like, you know, why ruin a good thing in that circumstance was the sort of prevailing attitude. I'm sure she's retired and like the system has evolved since then. Maybe not.
Speaker B: You know, that's such, it's so interesting because that is one of the themes that we constantly see where the Davids have opportunities to disrupt. It's These sort of industries, the space where it's like, that's always worked, but the problem itself is sort of already solved somewhere else, but it just hasn't been applied here. That's, I think the, you know, maybe that key insight for you initially as you start this. And, you know, I think, I think there's a, you know, false myth sometimes where we talk about entrepreneurs and they come up with, they start their, their business with this huge vision idea of how they can change the world. And I love how simple. You're like, no, we're trying to control f these files. Like, it's like such a simple insight. I'm not. I just know there's a better way of doing this. And I'm going to try and find a way in. And I'm going to find a way in through family law. That's the, That's.
Speaker A: Yeah.
Speaker B: Now you do family law for a little bit. You hate it for a year and a half.
Speaker A: Yeah. Got investigated by the Law Society for unauthorized practice of law. And sort of what I found.
Speaker B: Found guilty.
Speaker A: No, no, no, no, no. Uh, I mean, there's, there's, there's no guilt or innocence in those. Uh, it's, it's regulatory. But what, what I sort of learned from that experience was if I don't actually care about what I'm doing, like underlying the, the, the work that I'm doing, I not going to persevere through it. I'm not going to persist when it, when it gets hard or challenging. And so I didn't care about the purpose. I didn't care about the mission, to be blunt. Like, I didn't care about the people getting divorced. It was a means to another end for me. And, you know, it, it wasn't worth persisting at. And so we, like, uh, I remember the office we were in. I remember the people we were talking about it with. We sort of sat around a boardroom table one day and we're like, none of us like this. We don't want to keep doing this. But, but we've got cash in the bank. Like, what could we do with this? That's where like the initial pivot. Pivot started.
Speaker B: Yeah. And what was the first project that you got in the pivot?
Speaker A: So I think the first project we did was actually for a furniture company called Steelcase in, in Michigan. And what we ended up doing was building the meeting transcription software. So we, we knew there was opportunity at the time in machine learning. And so, yeah, we, we identified, you know, the, the transcription opportunity was a Pretty significant one.
Speaker B: That's hilarious because now it's, yeah, it's, you know, every software ClickUp has it now and uh, notion has it, Google has it. Everyone's got this meeting transcription AI Right, that's, that's, that's, that's cool. So you start on this pivot towards sort of machine learning, professional services projects and you sort of just picking up
Speaker A: projects where you can, you know, we said like we don't have a great product idea right now, but we have, you know, an opportunity to build a business and services and we'll figure things out there. I, you know, I think we had identified specific industries we wanted to work in, but we also recognized to penetrate them you need some sort of customer. Like you can't show up as customer zero or have them be, you know, your, your first customer. And so it was, you know, we, we had a, a bit of a destination in mind but eventually we ended up getting there.
Speaker B: Yeah, so what, walk me through some of those stages. What were some of the early customers? What do they evolved in? When was the moment for you where you're like, okay, we're in the industry we sort of want to play in and now we're, you know, we've got something here that feels like it's got some legs.
Speaker A: Yeah. So the sort of stages we went through. We knew we wanted to work in Canada and so one of our earliest projects outside of what I mentioned with Steelcase was we did a bunch of work for the Public Health Agency of Canada. This is well pre pandemic ironically. We worked on vaccine screening and the National Advisory Council on Immunization, uh, basically like the immunization approval process. So automating information extraction and assessing, you know, the efficacy uh, of vaccines, so building them systems to manage that information flow. Human. Huge amounts of, you know, open source research is, is available. How do you harvest all of that information to help them make a recommendation? As the council on is this a safe effective vaccine? So we did that. That project got chopped after the first phase due to lack of funding.
Speaker B: Ironic eh?
Speaker A: The second one was actually open source disease monitoring and this is probably like 2016.
Speaker B: Um, so how do you like you take on these projects? I'm just curious like you don't have any experience in vaccine or open disease monitoring. So like what's your playbook? What's your thought on this? Like okay, I'll, we'll bid for the contract and find a bunch of people who can model this out. Like.
Speaker A: Yeah, so at the time these were coming out as Challenges under a program called the Built in Canada Innovation Program. Bcip.
Speaker B: Yeah.
Speaker A: And so you didn't have to have any experience. You just had to like put your hand up and say you could do it and like prove, you know, through credentials or whatever that there was a, there was a chance you could. So we, we were successful in two of those and then from there we actually were able to use uh, that as a springboard to deliver A capability for U.S. special Operations Command in the States. That was a big deal for us at the time because it was the first sort of, you know, defense focused project. But it was also uh, us you know, really leveling up who we were delivering for and, and the sort of complexity and, and duration of the project. And so from there we were able to use that contract to come back and begin working for the Canadian Armed Forces. So that was probably 2017 is when that, that really got serious for us.
Speaker B: And that was, that was exciting times because like it's a pretty big professional services deal. You, you build up the team to be able to actually accomplish it, uh, to work through it. And how are you, how are you at this point funding the whole operation? So is it, how are you getting the team together to make this happen?
Speaker A: I mean that was a lot of the contracts were milestone based so you know, we, we knew what we could earn but we were running you know, as lean as possible. You know, sometimes my, my co founder Bennett and I were not, not taking a salary for a while to, to be able to make payroll for other folks. So you know we were, we were doing it sort of in the semi old fashioned way of, of like grit and determination.
Speaker B: Yeah, yeah, yeah. You know, I think one of the, one of the themes of your story as I, as I think uh, through is like survive long enough that you can just get the next thing right. It's this, it's this scrappy adaptability. You know, can we just get through this next year? Because I know there's another thing, you know, there's another milestone. So you take on these kind of pretty Large contracts within U.S. special Operations. You're working to deliver them, you hit some milestones, you unlock the next pieces. What's going well at this point and where do the obstacles start to show up in this professional service business that you built?
Speaker A: Yeah, so I mean I think, I think first and foremost my spirit animal is the cockroach. Uh, we, we've made so like later on in the story we'll get to it, but we, we've made sort of like Unofficial mission patches, which there's a few other startup founders in the defense space who. Who now have them.
Speaker B: And you have a cockroach on.
Speaker A: Yeah, it's a cockroach.
Speaker B: And.
Speaker A: And it says hard to kill. And. And like, the. The objective for many companies in this space at this point should be to be hard to kill as a company. It's. It takes a lot of, like, persistence and resilience to. To survive in. In this industry. So, like, you don't get to make these big, splashy announcements. It is like a slow, incremental compounding grind.
Speaker B: I think that's so interesting because, again, it is. It's almost. It's not about. It's not about winning. It's about just not losing long enough.
Speaker A: Yeah, yeah.
Speaker B: Like, if I don't lose long enough, I can compound little things that just break through in this machine that we're trying to enter and help improve. I was taking us back to your professional services moments here, uh, which, which is like, okay, so you get some big contracts, you know, something's going well, you're finally getting in some money, you're getting more narrowed on defense, you still got some other projects. What is working at this point and what is not? What is still extremely, like, challenging as you're building this business?
Speaker A: Yeah. So I think professional service businesses are very addictive. You get to have, like, continuous sort of incremental success if you're good at it. And we are good at it. Like, we're good at our jobs. That's something. I've been very fortunate. I have lots of people around me who are good at their jobs. But it's very addictive because the customer is going like, oh, my God, I can't believe you solved this problem for us. And you're going like, yeah, it's me.
Speaker B: I'm the. I did it.
Speaker A: Um, and, you know, I'm sure lots of other people could have solved the exact same problem for them. We just got the chance. Right? But I think that, you know, the. The challenge that professional services presents is like, you kind of hop onto a treadmill and every time you bring on a new person to bring on additional capacity, the treadmill speeds up. And, like, there's never really a time where the treadmill slows down or, like, you know, you don't feel like you have to run a bit faster the next year to continue to grow and, you know, sustain your business. And so what we started experiencing was two main problems. The first is the customer has these, like, epiph. Episodic contracting mechanisms. So you'd show up, you'd work, you'd deliver a solution for six months, whatever, and then they wouldn't have had a sustainment plan beyond that six months. So the contract would drop off. And the way most of the traditional services firms have solved that is everyone is an independent contractor. So like, you don't have a contract, you don't eat, you don't get paid. We only have employees, we don't do the independent contractor thing. And so it was a very different mindset that we, that we went in with and, and I think it's why we were able to deliver such outsized, uh, results for a team at the time of our size, like 14 people probably. Ah. And I think that as we started to experience these like, up and downs, we became sort of like Keynesian economists. We would save in the good times and then we'd spend it to sustain in the sort of like lean times. And what it meant was like, we kind of hit like a steady state at that size where if we didn't find a way to, to endure beyond that or like grow beyond that, we, we were just going to continue to operate at about that, that size. I think the other thing that, that we saw was, you know, much like my experience at the Federal court, much of the business that we were working in, in for the Canadian Armed Forces was extremely analog. It was extremely, like, it's not paper driven, but they'd taken that paper process and replicated it with like Word, PowerPoint and Excel are now users. But at the time, the customers, you know, employees were not particularly efficient at doing the work they had to do. And so the way they solved it was just working harder and like, you know, burning people out. Uh, and so the challenge that we saw became like the opportunity, the point of entry for like, hey, there is a software solution for this. And I think that, you know, when we finally sort of flip that switch and we're like, we are a software business now. I'd be lying if I said, we looked around and said like, are there competitors? We had no idea who else even made solutions like that. And I think to a degree to this day, like, we only know who our competitors are now because like, people compare us to them as opposed to us like actively going out and seeking them out. Yeah, it's been weird that we've never really done the market scan, uh, to assess that.
Speaker B: Uh, yeah, yeah, I think that's interesting. It's just sort of focused on you, sort of focus on the immediate problem. Your customer had the immediate next problem, you sort of identify it. But how did you know? You sort of. You come to this insight around the fact that within Canadian defense and analysts are still very analog. That's because you're in there with them, right? You're getting contracted as professional services to help solve key problems. And you're in there and you're watching them work and you're like this, yeah, this is bananas. And so, and so the professional services sort of was your Trojan horse, got you in there. You sold them what they already knew they could buy because they're used to buying and contracting. You get in there to try and help them and you realize, oh, my God, you don't even have the tools for me to help you. Like you're. Now you're causing me more work. Because even trying to just help you is, Is challenging. There's probably a number of insights that you come to during that professional services period. I mean, one, you sort of identified that whole feast and famine challenge of these contracts, especially for public service or these massive contracts. If it was a lot of small contracts, you could sort of, you get less maybe of a feast and famine, you know, but these massive contracts with, you know, that sort of fall off and then you've got these employees who are sitting there and nothing to do, no work to do. You know, law firms or consultants firms sort of solve that with a lot of like little mini projects that they've got going on. What insights drive you, you go, we need to be product, we need to be software. This is, you know, see a bit of the analog, a bit of the challenge of the professional services. I remember us doing an off site. And I remember, I remember us, uh, a couple things. One, it was like, okay, we've been doing professional services for just anyone and everyone. We've been mercenaries. We actually were, we were. You had Canadian Tire, you had, you had all of these sort of things. And then it was a moment of like, hey, we can't be anymore, and actually became one of your values. That we're not mercenary. Uh, we are gonna choose an area, we wanna have impact. So I remember us doing a very powerful values exercise at the time. And some values exercises can be complete bullshit. Like, uh, you know, like, we've all done them, um, we've all been part of companies that do them. That doesn't go anywhere. But I felt that one was powerful. Cause it was a decision making, it was a narrowing of like, because you had to let go of, uh, well, paying clients.
Speaker A: Yeah, you had to say no.
Speaker B: Yeah, like, that, I think is like, that's the. How did that. How did that feel? Take me to that one. Like, how do you say no to well paying clients who are. Who are feeding your payroll at this time? And how does your co founder, Ben the CFO go? Okay, I'm gonna say no to cash coming in.
Speaker A: It's a good question. I. So, So I remember there were a couple things. One was we'd already been talking about building a product to solve, like, some of the problems we'd experienced have this memory. And I can't remember who. Who told it to me, but. But the comment was like, no one ever makes the transition from services to product. I'm not saying we're there yet, but like, no one ever makes the transition. I was like, yeah, watch me. But I didn't just set out to prove some random person who I don't even remember now wrong. I. I think that the way we did it was Bennett was equally frustrated with, like, constantly having to manage those, like, cyclical waves. And we all agreed that, like, we are better off to fucking burn the boats and, and, you know, go all in on this than to continue to endure that, like, cyclical drama. And, and the sort of, you know, the. Honestly, that, like, uncomfortable feeling in your stomach that, like, do I know six months from now that another contract will materialize or do I need to let these people go? Today we were all kind of tired of that constant, like, base rate anxiety over that. And so that was. I think it was an easier decision to turn away, like, well paying clients than you might imagine. Yeah.
Speaker B: Yeah. Because it almost came to a point where, like, I don't want to run this business.
Speaker A: Yeah. Oh, yeah, yeah, yeah.
Speaker B: So it wasn't even.
Speaker A: Yeah, it was like back to the, like, it's.
Speaker B: Yeah.
Speaker A: Why am I doing this? Yeah, I don't care about the things I'm doing for the most part. Like, I, you know.
Speaker B: Yeah, I remember the. So. So we do the values exercise. We get narrow on who you want to serve, and this is when that sort of blurry vision that you had earlier on starts to crystallize more and more. Right. Like, we clearly want to serve the defense industry, and you get more narrow on that. So what is it today? Who. Who do you serve today? What's the. What's the, uh.
Speaker A: Yeah, so I think our primary focus remains supporting the Canadian Armed Forces. Department of National Defence. Canadian Armed Forces. It is, you know, deeply important to me that, that Canada has the tools and the equipment required to. To actually be effective in A modern fight. And I think that, you know, it's been a long time where we haven't really invested the, the time and attention in that. You know, successive political parties have, you know, reduced funding to, to the Department of National Defense, Canadian Armed Forces. And so, you know, for the first time in a while, I'm optimistic that that change is coming. But I think that fundamentally what we are doing is very, very similar to, to where we started like 12 years ago. It's like we gotta make things more accessible, easier and more available to more people.
Speaker B: Like, it's still, it's still the control F. Ah.
Speaker A: Of the control F. Like it sounds so silly, but it is still control
Speaker B: F. Cause there's massive amounts of data.
Speaker A: Yeah, it's still fragmented. It lives all over the place. Yeah, it's, it's, it's truly still a problem. And I think it's, it's not unique to, to D&D Caf, but like every big organization has the same problem. The number of times, you know, you, I'm sure even in your organization, like the number of times you're like, where is this document? It's like, why are we still asking that question? Um, that is the, that is the, the problem.
Speaker B: Years you had this insight that you could build software around this, but your own team struggled with that insight initially and it's taken a while to build software around it. So from that moment till you had and software that you could deploy, how long was that?
Speaker A: It's gotta be 2020. Yeah. With us, SOCOM, we had built some infrastructure behind the scenes just to enable the massive amounts of audio recordings that we were, that we were receiving and to manage the different machine learning models we were training and deploying onto devices. So like the, the first nugget was already there. Um, from that we. But, but like we've never used that code base since. So like, I don't want to leave you with the impression, but like we built something, but you built an internal competency. Yeah, but we, we started to understand, you know, there, there was some efficiency to be gained there. Then working with D&D Caf, we were able to pretty quickly get a working prototype live. Was it amazing? Like hell no. It solved a very specific problem for them. We ended up actually deploying that on an operation in 2021. And so that would be the sort of like horizon of like 2020. We're, we're having that argument.
Speaker B: Yeah.
Speaker A: 2021, we have like a minimally viable product that is now operationally deployed and offered. You know, I think an extremely high amount of value to the customer on that.
Speaker B: Yeah, yeah, that's pretty quick turnaround.
Speaker A: Yeah. Yeah, we didn't a lot of money to do it.
Speaker B: No. You then go through changing this team, uh, from a professional services team to a product software team. There's some pain around that change management there. How was that process like?
Speaker A: Yeah, I mean, the thing you optimize for in a services organization is not the thing you optimize for in a product organization. And so in a services organization, you need the most tolerable consultant you can possibly put in front of the customer for the lowest dollar amount you can possibly find them at. Yeah, I had, I had a friend who ran uh, like, they're called like body shops in the industry, but basically they, they like are the staffing companies for the government of Canada. And his expression was always, you know, my business is selling B minus consultants to C minus customers. And, and, and like, it kind of is reflective of what that system, you know, optimizes for is. Is you want the cheapest tolerable consultant you can deploy. That team is not a team that can build a product. No, that team is a team that can go in and, you know, keep the customer happy. Ish. And so the shift there was either upskilling those people and we did do some of that, or, you know, finding off ramps for those people to. To, you know, land somewhere else where that skill set is still valued. Because there are still lots of body shops in Ottawa where that skill set is valued though, that they can, you know, continue having a successful, productive career. Just not with us.
Speaker B: Yeah, yeah. And yet you had to overhaul quite half the team almost.
Speaker A: Yeah, maybe. Maybe a little more than that. Pretty m significant churn through that period, for sure.
Speaker B: And I mean, that's interesting because as, as when you're building the team, you know, you're able to off ramp and overhaul team members. But you as a leader and Bennett as the founder, as co founders, there's no, there's no off ramping. You guys, you guys have to change. You guys have to adapt. Your skill set has to evolve. There's a few moments of your skill having to evolve, right? There's like the early moments of this being, you know, a family law sort of thing. Uh, then the early moments of just like getting a bunch of contracts, then you sort of hone in on defense contracts, preferential services there, you know, for government of Canada, and then going over to product. Your skill, your leadership, your ability to bring a team together has to constantly evolve and change. Look Back at Sam from five years ago, eight years ago. How have you changed? And then what has stayed the same? What are those characteristics that you're like, you know what? I'm still this way, and. And I'm thankful for it because it. It's allowed me to get through some challenges or here's parts of me that had to mellow or I had to figure this. These skills out.
Speaker A: I can turn this around on you and say, like, f. What have you observed change? Because I think we've worked together long enough that you probably have some answers, and I can. I can build on that. So, like, what have you seen change?
Speaker B: Yeah. Yeah, that's. That's. That's a good one. That's, you know, so. So the one that. The one that comes to mind. There's. The immediate one that comes to mind. Sam's a fiery spirit. Like, there's a. There's a fire. Fire to you. And I think that I've not. It's not that I've seen the fire mellow out. It's that I've seen you point the fire elsewhere. I think that in periods of professional services, and I see this in myself, because, like, uh, again, a professional service business is this feast and famine that when we're in the famine period, that fieriness turns inward sometimes on our own teams. Right. Like, we're frustrated. Why aren't you doing this? I'm always the one having to do this. There's this real. But it's a flaw in the system and not completely a flaw in our people. It's just the way we've designed the business when now I've sort of seen you turn that fire outward towards the Goliaths or the industry. And so using that fireness, that energy, that, uh, brilliance towards speaking up, advocating and moving things at a systems level versus sometimes internally. So that's where I see, like, a shift from, like, being inside the house to outside the house. And that happens because I think you built a strong executive leadership team that's taking care of the house now more than, uh, more than before. So that's. There's. There's something I've seen. Yeah.
Speaker A: I think. Fair. I definitely am fortunate to be in a bit better of a position to advocate more broadly for what has been historically a very challenging industry to operate in. As a newcomer, I think from my perspective, what's changed is, like, the problems that I'm now having to solve have changed, and so that's forced me to develop new skills. You know, I remember in high School, I had a deathly fear of public speaking and like, yeah, look at you now. Look at me now. Now I will willingly go and sit on a panel on stage. You know, I think one of the other ones that, that still I personally recognize in myself. And maybe that's, that's the other thing that's changed as I am much better at sort of like introspecting on what's consuming my, my energy. But part of the role of CEO is to be like out advocating for your company. And that means, you know, attending events. I've had to start to develop those skills and figure out how to, how to navigate like uncomfortable social settings for myself. And so, you know, how has that changed? Well, like, I took my wife to, to one of those events, uh, a few, a few days ago, and she's like, I didn't recognize like the person that was like walking around the room talking to people and like, I, I've had to develop that as a skill because it's not something that I was, unlike you, innately born with.
Speaker B: Yeah. Yeah, I love to see that. I think the other piece is you've, you've gained further conviction in some of your intuition. I would say a younger Sam had less conviction in those contrarian opinions or willing to voice them. And now it's like, no, I'm, I know I know something here and I trust my intuition more. Which has allowed you to be, I think, more effective as a leader also. Just interesting to, to reflect on. So, so 2021, you get, you get, uh, an MVP into the caf. And I remember a product meeting we're having and we're in there, but this product is absolute shit. And, and, and you're frustrated. One of my analysts can figure out a way to get the tool to do what it needs to, but that doesn't make it a product that actually can function on its own yet. And so you're still bridging this gap for a number of years of needing essentially your own professional services team with this sort of product that you're creating. Walk me through those years at uh, 21. 2021 year and sort of in growing with the caf.
Speaker A: So I mean, I don't think any, any product team ever releases something that they are proud of the first time or like any time. It's always a compromise. And I think, you know, the, the joke, like it works on my machine is, is so persistent in the industry because like, you know, the, the, the engineering team's job is to build the minimum amount of stuff they possibly can with the time you've allotted them and products job is to go like no, this is like the minimum standard I'm going to hold you to. And those organizations should always be in some level of conflict or tension over that. But the sort of transition we made, we had a bunch of you know, failed product starts effectively with, with different product leaders. The product journey was we, we basically built a search interface and a task tracker integration so that you could search against like you could task someone with something, search against the data repository. That's what got deployed very, very quickly and was very effective. But it tells you sort of how simplistic the tools available were.
Speaker B: Um, that's so interesting, right. Like there's part of your David strategy. It's like you built a two feature
Speaker A: uh, product search and like nothing new or novel about either of those. Don't misinterpret whatever right.
Speaker B: Like there's no crazy innovation you yourself in through a Trojan horse. And then you said we're going to build you guys a software ah, that's going to allow you to search all this stuff that my team is having to search for you already. And then we're just going to help you track tasks so that they're not tracked on an Excel sheet.
Speaker A: Yep, that's it.
Speaker B: So basic. You know, it's one of I mean Claes Christian's book the Innovator's Dilemma. He goes, you know, the innovator builds a shittier product for a smaller market. I think in 2021 you were still, you were still searching for other customers to deploy to. But there is a moment where you go, you know what? Forget all any other customer. Yeah, one customer in this case and a very simple product that can just get us in there. How was, how does. I mean, how did that feel?
Speaker A: Felt liberating to be, to be honest. It was, it was. You know I can't remember exactly when we made that decision. It's a few years ago now when we made it. I think it created an advantage as well where every other sort of competitor that was, you know, long established, they sell to a huge variety of different governments, they work on you know, a huge variety of different use cases and our sort of like no, we're fixated on this single customer and we're going to make sure that they are super frigging happy with whatever we do. It let us go and you know back to that sort of like professional services mindset to an extent and bolt on with them and say we are going to make sure we Deliver mission success at whatever cost to like the company. And you know, we continue to promote that mentality internally is like, we're there to make sure that they have mission success, not to, uh, not to, you know, win another contract. Like those things come, we trust that they come. Now this is like, we make you successful, we do the things you need us to do and you know, even some of the things that you may not know, you need us to do. And you know, we trust that the rest will come. And I think that that's enabled us that focus on like, relentless focus on our main customer and like, you know, outsized impact in delivery has been a real differentiator from some of the like legacy defense primes that, that you know, we would be competing against.
Speaker B: Yeah, and, and you again, I think your, your, your strategy early on was we didn't even know the competitors. So you know, like, we sort of walk in and realize we just want to solve this problem really well. But then you start to get to know the competitors a little bit, you start to see where they're winning contract there starts to become this, uh, the Goliath starts to become very apparent and the space that they hold. And I think, as you just noted, they're sort of doing everything for everyone in this space. They're these massive software conglomerates. And you go, you know, here's David's slingshot moment, right? Like you go, here's one client, very narrow. But there's, there's also this attitude of, of I think you said, like this mission crew, we're going to make sure this rep, because they're also not paying enough for your growth just yet.
Speaker A: And I think the, you know, you've characterized it in a negative light and I think it's actually been, you know, in hindsight a positive for us. So by having to operate lean, by having to, you know, figure out what we can do with the minimum amount of resources, it's actually sort of converted into like an unofficial design philosophy of ours which is like, well, we can't just build every feature. So like, what is the most impactful feature right now that you know, moves the ball five yards further down the field? And I think that what it means is also like, if you add a feature, sometimes we also have to take a feature out that isn't getting the user traction we want because we still can't afford to maintain, uh, an ever growing sort of topology of features in the application. And so is it frustrating that sometimes we have to say, like, we can't do that? Right now, like, yeah, I'd love to have infinite money and just, you know, do whatever the hell I want.
Speaker B: Isn't that when we make our most mistakes?
Speaker A: Right, yeah.
Speaker B: Yeah.
Speaker A: You know, watching, watching companies now that are, that are raising money on, on like the hype that has suddenly entered the defense market. I think it's going to be a real burden for those companies in the future. They don't understand the customer. They don't have, you know, direct feedback and access. And even if they get that, they're going to have spent so much money and created so much, you know, outsized expectation from their investors that it's going to be like a real boat anchor around their neck where they have to charge more and more money and deliver less and less. And so I, I think there's, you know, not, not to mention that like, in my view, venture doesn't lend itself to, to the defense market. You, you are making a bet in a market you don't understand. It takes five years to, to actually enter the market, to get your clearances, to be able to hold your own clearances, to be able. Abilities to talk to the people whose problem you think you know how to solve, only to learn that like they don't want that problem solved absent that access. I think it's, it's a really, really risky bet that a lot of people are taking right now.
Speaker B: Um, no, you're right. I think, I think the, the leanness here is the sort of superpower. It is the, the advantage that you have because you can now work at a speed and uh, an ability to be focused on more than ever.
Speaker A: It is unequivocally luck that put us here. And I think the only thing that allowed us to be in a position when we got lucky to like actually run through it is survival like that. We've been here for long enough that like, I think this, the sort of like lesson that I've taken away from this is like by surviving and persevering through this, you put yourself in a position to get lucky. You know, it's like it feels like there's often this sort of, you know, mythology that's created around companies that are successful where it's like, no, no, it's like they're just, you know, a brilliant individual. Like, I'm not a brilliant individual. I'm, I'm lucky that this is a moment in time that I'm hopefully going to get to be a part of. But like the trade off there is like the way we got there is, is really fucking Boring.
Speaker B: Yeah.
Speaker A: Grinding it out for years and years. But we put ourselves in a position with more at bats. You know, the, the famous Michael Scott quote, you miss 100% of the shots, you don't take Wayne Gretzky. But, like, that is the, that is the fundamental challenge, right? Is like, you, you got to have the at bats. If you're, if you're not getting, if you're not getting at bats, you can't get hits. Like, it's, it's pretty fucking simple.
Speaker B: So what are some of the key strategic heuristics that you now hold on to as. As this, as, uh, knowing that you're. This David going up this next kind of. You know, one of the heuristics we're talking about is survival. Like, survive long enough to get lucky. I think that's. That, like, I'm gonna survive long enough so you can get lucky is, is, is a, is an interesting one for me. So that one seems, seems fitting. What are some of the other ones that you go, you know, here's some strategic heuristics that we, we run. Um, by now, this, this is sort
Speaker A: of the challenge we have is like, we've been so sur. For so long that it's like, I don't think we know when it's time to make a bet.
Speaker B: That's, that's interesting.
Speaker A: Like, it, it's, it's, it's. It's the challenge. Um, so you've, you.
Speaker B: Which is interesting. So then you're characterizing the majority of your actions to be. Not. They're, they weren't bets. They were known.
Speaker A: You were close to. Known as, like, as close as humanly possible. Yeah, we are. We are getting to as close to certainty as we can before we, we make a decision.
Speaker B: So you're, uh, at like, 90% certainty? Yeah. Yeah. So that's interesting. So what does, what does 80. Yeah, what does 80% certainty look like? Right? Is, is, is maybe the piece that you're toggling with.
Speaker A: Yeah, I mean, the, the, the other one that, that I, I, I keep thinking about while we're sitting here is, is like, you know, for a while, Bennett and I, I mean, since, since we've been working together, we've joked about like, oh, that's a champagne problem, and, and like, a champagne problem being like, oh, uh, that's, that's a problem once you've, like, you've made it and you get to, you get to pop the cork. And, and like, the reality that we've confronted is like, there's always More champagne. Problems like you, you're always having to solve the next problem. And like, the problems are different and, and, and the, the barriers are different, but, like, I'm not sure any business ever suddenly just, like, goes like, all right, we're done. We've done it.
Speaker B: Like, got no problem.
Speaker A: Yeah, yeah, game over.
Speaker B: Um, and if they do, they end up the Goliaths of the industry where.
Speaker A: Yeah, yeah, that's right. That's right.
Speaker B: Sitting on their laurels.
Speaker A: There's enough they're taking in.
Speaker B: Yeah. Too much hurts, they're taking in their profits. And eventually someone comes in and. Let's. Let me flip it then. What do you think your Goliaths, the big competitors in your industry, are blind to right now that you go, there's, uh, this is where I think they're blind to and not seeing. And that's going to be maybe their demise or what allows you to compete.
Speaker A: Yeah. So I think a lot of our Goliaths in the industry are American. And watching the sort of, like, general reputation of. Of America tank has been sad for me. Like, I won't lie.
Speaker B: Like, I was very, very. It's a very moment in Western society.
Speaker A: Yeah, yeah, it's been sad. But I think that the, the thing that a lot of them are blind to is that, you know, the rest of the world has taken notice that America is not as trustworthy a partner as they once were, that they will, you know, step over your corpse to make a buck at some point. And I think that that is starting to materialize in places where, you know, they would have traditionally been the easy incumbent. And so it's opening doors for us in places where, you know, two years ago it would not have been, you know, even an open conversation. So I think that's one place that I'm not sure they're blind to it. I'm just not sure what they can do.
Speaker B: Correct.
Speaker A: I think the, the other piece that, that they're blind to is that not everyone spends at the rate that the. I, uh, mean, no one spends at the rate that the American government spends on defense. And the, the way they price and compete in most markets is incredibly punitive to the people who are actually paying tax in those markets. And so I think that people are much more sensitive today to, like, localized sovereign industrial benefit as opposed to what they were maybe two years ago. And I think that when, when big American companies come in, they now just tell you how they think you should operate versus being a collaborative, collaborative partner. So I find, uh, you know, my experience has Been that that is increasingly off putting especially as we are seeing, you know, the geopolitical tension and frustration mount around the world. And so again, I'm not sure they're blind to it. I think there is just this, you know, brash American behavior that is, that is now starting to rub people the wrong way.
Speaker B: That's so interesting. Yeah. I mean and it's not necessarily something they have done. Right. Like it's, it's, what's interesting is like the landscape is, is changing underneath them. Right. It's, it's, it's not their misstep, but it's a political misstep or you know, decision that has led to, led to this.
Speaker A: I mean they're making money hand over fist out of the department of War in the United States. So like they do play a role in, in all of this. You know, they, they've placed people in the, in the current government to a lobby, I'm sure.
Speaker B: Yeah, yeah, yeah yeah.
Speaker A: Not none. Canada. They've placed them in the, in the US Government to, to exert influence. So they have played a role. Um. Has it been economically beneficial? Like. Yes, absolutely. Look at their, you know, many of them are publicly traded. You can see it.
Speaker B: Yeah.
Speaker A: But it's at the expense of the rest of the world.
Speaker B: Mhm, mhm, mhm. And that's, that's you know, when, when Goliath gets a little too greedy lining their pockets. Right. And, and not, and, and because, because you know the other insight, you know I asked you earlier what are some of the heuristics. You sort of said it earlier which was oriented the mission like you were going to help the client achieve their goal. And it's not a checkbox of like well we deployed software. You have it like it's your users not using it or not making it. No, no, we're going to make sure we get you all the way to accomplishing your objective. I think that's beautiful because you've blended this professional services mindset with software. And, and I think in a way, I don't know, like I, I, I uh, I'll go off on a limb here but do you think that's the evolution of, of certain software? Because like you, you, you see the big software enterprise like Salesforce, you can't implement Salesforce without a huge implementation like uh, professional services to the point where Salesforce has lost a ton of customers to simpler products that don't take so much work to configure. Right. So this sort of large enterprise than meeting implementation team was was this play. But it's like, what if we simplified the software, still gave you an implementation team, but was focused less on just the software, but actually helping you achieve your goals.
Speaker A: Yeah. So I think, I think the, uh, the sort of software as a service model that exists in, in relatively simple applications does not exist when you're talking about, like, the accompanying organizational transformation and like, process transformation that needs to accompany, you know, deeply complex, you know. Yeah. Policy, regulatory, oversight. Like, there are so many more barriers, hoops, challenges that the average customer in defense has to. Has to jump over than there is in like installing an app on your iPhone. Yeah. So, like, yeah, you can, you can leave that up to the customer on an iPhone app to adopt. Uh, but when we're talking about deploying something that is like, in a sensitive environment, handling sensitive information, dealing with things that people are sensitive about, I think that the adoption burden, the adoption hurdles, the tyranny of the status quo in those environments is way higher. And if organizations aren't deliberate about that transformation and it requires bolting on external experts to make that, to help them make that leap. I think if, if you're not doing that as an organization.
Speaker B: Yeah.
Speaker A: You're kind of setting yourself up to failure. You're creating that, like the field of dreams. It's like, if I build it, they will come.
Speaker B: Yeah.
Speaker A: And you know, repeatedly that.
Speaker B: So now you sell them. Change management.
Speaker A: Yeah. Unfortunately, I don't like those words, but like, yes.
Speaker B: What are the type of leaders you've needed around you and, and you. You've had to change some of the leaders seems to change quite a few over the years, but there are some that have done well. And lastly, what kind of leadership team have you had to be. Have you had to establish in order to survive this long and not pull your hair out?
Speaker A: I have pulled my hair out. So when we're talking about leadership team, I think, uh, there's a book, the Hard Thing about Hard Things, Ben Horowitz. And in it he talks about how the team from 1 to 10 is not the team from 10 to 100 is not the team from 100 to 1000. And I think one of the best reflections in that book, you know, he says something like. And like, make no mistake, when you're reading this book, like, I'm talking about you as well. And so, like, I'm conscious of the fact that, like, at some point maybe the company outgrows me. But, you know, when you're, when you're early days, you need people who can do a lot of different things. You don't need a ton of specialists. You need. You need generalists who don't have a ton of depth but have, have a lot of breadth and maybe one or two specialists that are, that are, you know, effective at the sort of thing you're focused on. As we've, as we've sort of matured through this journey, we've now started to recognize when we need a specialist for a particular role, and we've done a much better job of defining that in advance and bringing that on. But I think that, you know, still, fundamentally what we need is, like, people who are independent. I, I don't like micromanaging. I don't like hovering over people's shoulders or telling them what to do. I would much rather they go out, make a mistake, come back, go, like, here's the mistake I made. What can we do to fix it? So, you know, I don't want to micromanage people. I think the, the other main piece that, that I've, I've learned. And, and in, in fairness, I was told this like, 25 years ago on one of my, like, first jobs. I was working construction up north. I was building, uh, I was helping, like, build custom homes. A big, big.
Speaker B: I didn't know you were doing that.
Speaker A: Yeah, yeah.
Speaker B: And, uh, was carpenter. What were you.
Speaker A: I showed up and I was like, dude, I'll carry tiles. I want to learn. Managed to last past the first week and then worked two full summers there. It was great. But I was working on this. This guy's like, massive. It was like a 20,000 square foot cottage. Like, unbelievably huge cottage. Yeah, yeah. And. And he was the former, like, CEO of Mobile One, something like that. He'd drive up from Arizona every summer, stay in the Muskoka, and then drive home, you know, as soon as it started to get a little bit cold. And. And I remember, like, when he found out that I was just like, doing like this as a summer job, he was like, oh, what are you doing? Asked me a bunch of questions. And the advice he gave me was like, Sam, like, whatever else you do the rest of your life, make sure you're a good communicator. And, and like, I kind of like, yeah, yeah, uh, sure, I'm gonna be an engineer. Like, I'm gonna build shit. Like you. You don't know what you're talking about. And like, sure enough, the thing that pisses me off the most is when people can't effectively communicate, when they cannot want, need, when it's like, I Have to spend energy to get the thing out of them that they're trying to tell me. Drives me bananas.
Speaker B: Yeah.
Speaker A: And, and I think that the, the, the lesson I learned retroactively is like, should have listened to him a long time.
Speaker B: M. Like when less than 1. Yeah.
Speaker A: Like when smart people tell you think, don't dismiss it outright. But, but I think that, you know what, what I'm starting to value more and more amongst the, the team that we've got is like their ability to communic. This is the problem. These are the potential solutions I've identified. You know, breaking problems down, communicating them. Clearly that makes my life easier. I get it's not all about my life being easier. But like this is, this is a place where like, if you need me to expend effort on your behalf, telling me why I'm expending the effort and what you need me to expend it on.
Speaker B: Yeah.
Speaker A: Uh, so much better than having to figure it out after a two hour discussion.
Speaker B: Yeah. Yeah.
Speaker A: Can't sit in another fucking meeting with no purpose.
Speaker B: And so, and so how, how do you, how do you encourage communication? How do you make better communication part of the culture as a team? Both executive team, full team. Like you've, you've done, you've, you've made some strides on the team, overall team culture. Right. Like, you, uh, know, early on after the pandemic, you said, hey, we're coming back to the office. Like, I want people in, I want people chatting, I want people engaged. So, so how have you built, I mean, some practices around communication? Is there anything that you're like, you know what? This is work to, to create a better flow?
Speaker A: Yeah, I, I think, you know, we, we still operate hybrid, we still have some fully remote employees. But I think the, the, the observation we made early on in the pandemic was like, no one was properly equipped to, to function well in the pandemic. Stuff immediately reverted to the like lowest cognitive threshold possible, which is text. And so like you'd get a slack message and then you read it in whatever fucking tone you wanted. You work yourself up, you respond. And so you know, for me personally, I like, like one on one interpersonal engagement, but like one on one. I'm, I'm, I'm. That, that's a, that's a happy place for me. And so I think, you know, encouraging people to come back to the office, incentivizing it. What we've observed is the people who come back to the office and, and like engage the, the, the things that are important to me. Communication skills, you know, team development, collaboration. They've dramatically exceeded the people who are fully remote. It's not an indictment of remote work. I'm sure we could do a much better job of better integrating fully remote and fully in the office. But the camaraderie that gets developed by being in the same place as other people every day, it's hard to replicate that. We fly people in now. We do things to bring everyone together because we recognize the value of it, but it's almost impossible to replicate.
Speaker B: Mhm.
Speaker A: And so I think, you know, from, from an executive standpoint, I could not imagine having a fully remote executive. That just doesn't, it doesn't make sense to, to me right now. Yeah, maybe at some point in the future it would, but it, it doesn't make sense. And I think the, the challenge is like at the executive level, the, the friction is the highest. It's like you have to be capable of, of fighting, but fighting fairly. Do I expect you to be in the office every day? Like, fuck, no. Work from home, do what you need to do. But like when we are going to have hard discussions, we are going to make time for each other and be in the same fucking place to have it.
Speaker B: So. Yeah, yeah, I love that you're hitting on that because I mean, you know me and you know my work and how much I love the importance of productive conflict and just debate. So like, what is your reflection on the value of productive conflict on this massive journey that you've had of building Anvil? Are there moments where you, you think back, hey, you smiled. So I'm thinking, yeah, I mean, I
Speaker A: mean you sort of started this off where like, you're uh, a contrarian. So you're wrong a lot. And it's like, yeah, fuck yeah, I'm wrong a lot. But I think that the, the people around me who have like sat there and forced me to like, reason or think better, that's, you know, that's, that's been a, uh, the single biggest enabler to, to becoming more effective. You know, when I, when I first started my clerkship, I, I, I clerked for a judge. Bigger, big scary man, lovely. Like I, I think the world of him. So don't, don't misinterpret that statement. But like, but like very intimidating. And, and I remember one of the first times I walked into his office with my first like bench memo, which is like, you write up like, you get a case, you, you're, you're told, effectively like, tell me what I Need to know about it and tell me what you think the decision should be. And I passed it over to him and he sat there and read it for like 10, 15 minutes, end to end, probably multiple times. And then he looked up and he just started hammering me with questions on what I'd said. And I'm sitting there in a suit, like two weeks in, like, yes, and terrified. And. But like, he forced me to get better at the, like, logical reasoning component of it by having an argument with me. Not a. Not an unfair or an angry argument. By having that, like, that, you know, verbal combat. And what I, what I've like, come to appreciate is like, if people can show up and, and, and have that, like, verbal combat, we all start to think better about the problem. And so I like that.
Speaker B: I actually really like that it is through debate and it's through verbal combat that our ideas get better. You know, I. Obviously teasing you a little about being wrong contrarian, because it's when the contrarian is right that they're outsized. Right. That's the whole, uh, uh, yeah. And. And so, and so what I've enjoyed seeing or participating in with your team is when we've had these strategic discussions and we've got everyone in the room and we are debating ideas and challenging those sticky notes up on the board and having these moments. I feel like there's real magic, there's real value in it. And it gets tense, you know, it should. It should. What have been some moments that you reflect on where some of the best. You feel like good decisions came out of, like, good debate and conflicts or any moment that comes out where you're like, you know what? We had a big conflict. We had a big debate over this. And it was only through the tension that we got to a place that was better. Do you have a specific example?
Speaker A: Yeah, I remember, uh, one of those retreats, there was a moment where Brad turned to me and said, so we're just building tableau or like, power bi or something. And I remember, like, just rage building inside of me. But he wasn't wrong. Like, there was truth to what he was saying. It just wasn't. I wasn't expressing myself well enough. And so what he was seeing was like, we're just building like, a visualization tool. And that is not what we build. But I think that it was a moment where, like, we'd been arguing for a while at that retreat about like, you know, what specifically is the value add that we are adding? And Brad had heard we are building visualization Layers on top of the information. And I think that that was a very productive, like, argument at the end of the day, but, like, the moment where Brad is like, so we're just building tableau. And I was like.
Speaker B: Because it also makes you realize what the other person. It makes you realize the gaps in your communication.
Speaker A: Yeah. Yeah.
Speaker B: Okay. So all I've been able to communicate is to get you to this point. Like, I'm. I'm doing something wrong.
Speaker A: Five years later, we still haven't built tableau.
Speaker B: We have visualization to. It's because there was a map. At one point, there was a map and there was data points. There still is a map. Yeah. I wasn't sure because we went from search and task manager. Where are we now? Search task.
Speaker A: Search task map, Map annotation services. Yeah. Some data pipelines.
Speaker B: Yeah, There we go. It's expanding. Uh, yeah. Uh, that's.
Speaker A: Scope creep.
Speaker B: Scope creep. What have you changed about your conflict style or the way you approach conflict over the years as a. As a leader? Because we know it's important. We know it's good.
Speaker A: Yeah. I think probably what's changed the most for me is I've seen it with some other people where the fun for them is the argument, as opposed to, like, why we are having this argument. And so make no mistake, I still enjoy a good debate. One of the things that you've actually helped me recognize is, like, when it's important, when you're wearing a CEO hat, like, what you say ultimately does go, like. Like, there is no debate at the end of it. If. If you just, like, say, yeah, well, fudge you, I don't believe you. I'm doing my way. And so you either go in with the intention of, like, actually getting feedback, or you just tell them what you want to do. But there's. There's no middle ground there.
Speaker B: Yeah.
Speaker A: Um, you got it. You got to, like, pick a fucking lane and live with it. And so I think that, for me, probably the most important one over time has been, like, knowing when I'm making a decision and I'm not willing to listen to other people versus when I want feedback and I want to be challenged. And I want to have that discussion and being clearer about which lane I'm in, because straddling it is, like, the most basic place.
Speaker B: Now, you've had some interesting dysfunctional team members over the years. There's the brilliant, difficult to work with because they're sort of kind of on their own. But then there's the brilliant difficult to work with an I'm gonna add that, like, you know, kind of egotistical piece or. Anyways, you've had some difficult and not naturally a place. How have you dealt with them in the past? What have lessons learned around dealing with?
Speaker A: I think a lot of those people in my past. I think the. The lesson that I continue to learn is, like, when you get that first sort of like, red flag, there's probably not too much more rope you want to give that person before you. You make the decision to, like, move on without them. It is. It's a constant failing on my part to not, like, end that soon enough. And the harm that, like, you are not aware is being caused elsewhere in the team is. Is almost inevitably more significant than you're giving it credit for. And so I think the biggest challenge I've always had is like, the second bad behavior starts to materialize, number one, like, correct it. If they don't accept the correction, that's pretty much the end of the relationship. Yeah, I've never successfully lived by those words. Is the. Is the reflection. And so the lesson that I expect I will continue to learn is like, you know, gotta make the correction. Gotta make the decision sooner. Faster.
Speaker B: Yeah. Uh, because it comes harder and harder to make the correction.
Speaker A: That's right. Yeah. Oh, absolutely. It's like you start to try to find, like, weird patterns to. To. To escape the situation instead of recognizing, like, no, I have full autonomy to end this right now.
Speaker B: And I think you, uh. I think that's part of. When I'm talking about the growth in a lot of leaders is the growth in the conviction of your intuition. Because before we would doubt ourselves more and more and more. Like, uh, am I the crazy one? Maybe it's just me. I'm not getting along with them. But as your leadership grows, as your confidence grows, you go, no, I've seen this pattern before. I'm aware of it. I'm not going to feel good about it. But that conviction in your own intuition is key. So we've talked about some of the strategies. I like this focus on conflict and kind of the importance of it. I think about the different debate points where you have to assemble your team to go, okay, we're not loving divorces here. There is no love in divorce. That's the name of that chapter. There's no love in Divorce. So there's a debate that the team has to have around where we want to go next. And then you pick up a bunch of professional services contracts, and then there's a debate, a point where it's like, hey, we can't just be professional services for everyone. Who are we going to be? And it's sort of this debate over choosing defense, and then there's this debate and conflict around burning the boats and go, okay, we can't be professional services for all these different things. How do we. And there, there are these pivotal moments where you had to allow for really good debate and conviction to show up and, and, and, and create. So I like that. And I think that's, uh, a. It's a good theme for us. So we've covered strategy, we've covered some things about the team. We've covered some things about your leadership. What's next? What are you excited about here? What's the future of Anvil? What. What, what should we be looking out for?
Speaker A: Yeah, I think at the, at the moment, we're, we're sort of grappling with the, uh, the next set of champagne problems, which is we're growing faster than we ever have. And so, like, over the last week, we've basically added 10 new people. We're doing. We're onboarding and training in groups now, which is, like, not something we've ever had to grapple with for, for efficiency. Yeah, I, uh, You know, Brad's. Brad's in on weekends building desks because it feels like an operations problem. Like, poor Brad.
Speaker B: Everything. Everything feels like.
Speaker A: When he told me he was doing that, I was like, dude, I'm buying pizza for everyone to build these desks. Like, let's just. Yeah, so I think there's, you know, there's. There's a whole new set of growing pains and things that I don't know that are going to be the, the next chapter of this. But, yeah, I think it's, it's, it's an exciting time to be in the defense industry, for sure. How that materializes is still like, you know, we're focused on survival, not letting our head get too far in front of our skis and.
Speaker B: Yeah, yeah, yeah, it comes back to survival. Survive. And let's ride this new wave and see where the wave takes us. That's awesome. Well, Sam, thank you. Thanks for sharing your story and your insights and the journey. I think it's been a pretty, pretty cool journey to be a part of. Pretty cool journey to watch and a, uh, journey that I'm excited to write about and tell stories about. So thank you for sharing with us.
Speaker A: Thanks, man.
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