Guy Filippelli: From Military Intelligence to Venture Capital | Episode 003 | 06-27-24

In this episode of "From the Ground Up," we feature the fascinating story of Guy Filippelli, Managing Partner of Squadra Ventures. Guy describes his experiences from a military intelligence officer to a successful entrepreneur and venture capitalist. He provides a unique perspective on guiding startups, drawing from his time at West Point and Oxford and his commitment to being a leader who inspires growth.

Guy emphasizes the significance of defining your brand and creating a name that sticks.  He believes having a military background has shaped his business and leadership approach. He shares insights into every startup's critical first 100 decisions and how Squadra Ventures guides and supports entrepreneurs through these pivotal moments.

We also discuss the current global landscape and its implications for technology and venture capital, offering Guy's perspective on how he approaches these complex challenges.

A recurring theme in Guy's journey is the profound impact his father had on his drive, ambitions, and direction. His father's guidance and support gave him the essential foundation to build his life and career.

Guy highlights his dedication to philanthropy through the Commit Foundation, which aids veterans in their transition to civilian life.

Don't forget to like, comment, subscribe, and share this episode for more business startup stories and business insights! Thank you for listening.

owners about their successes, how they got to the place they are today, the journey that they traveled, the perils that they overcame, and the successes they had. And our hope is in this conversation that, that we can bring something to budding entrepreneurs, existing entrepreneurs, and maybe even some that have been through it once and are thinking about doing again. I am thrilled today to have my guest, Guy Filippelli. Guy, welcome to From the Ground Up. Thanks for having me. Absolutely. Guy and I have known each other for quite some time. It's usually about this time, Michele. I like to do my disclosure, and that is, not only are we friends, but we're also investors in Guy's current firm, which we're going to get to. And Guy does an absolutely wonderful job in his current position, but we're going to get there. Guy and the Filippelli family is also a small client and a happy client at Verdence. You are, and we enjoy having you and your family. Thank you. Guy, let's get started with a little bit about your background. So, Guy is a managing partner of Squadra Ventures, which is an early stage venture fund, but a very unique one. It's in the defense, in cyberspace specifically. Guy spends a lot of time in Washington, DC and the surrounding area. But before that, Guy has already been successful in other businesses. Guy was the CEO and founder at RedOwl Analytics, which you had an exit, and a good exit also. Berico Technologies. Did I pronounce that correctly? That is correct. And before that, Guy's career gets even more interesting. Guy spent some time in intelligence for the Army, where he traveled all over the world and And really had some unbelievable experiences, which we'll talk a little bit about that today. And Guy was also a West Point grad, so he went to the military academy at West Point and finished his, education over at Oxford. Guy, you've been around quite a few places. Now I'm in Baltimore. And now you're in Baltimore, and you're. And you're doing Squadra Ventures. Well, welcome. We're going to. We're going to kind of dig into this a little bit and walk through each one. I I have a quick question for you because. Because I love the story and I've heard it, but I'd love for everybody else to hear the story. Squadra, where'd you come up with the name Squadra Ventures? Yeah, it's, you know, when we were first a couple, there's a good lesson in naming. I feel like, in hindsight, but when we were first thinking about launching a fund, the original, I think, instinct that I had was to try to find a name that described very clearly what we were. And I know you're a branding guy, and you get into these things, like, I mean, make it up. Defense Venture Fund. Obviously, we wouldn't call it that, but something that would. You would read it, and you would know exactly what it was. And I was talking to these guys one day, and they said, if you choose a name that is obvious to everyone when they first read it, the name defines you. But if you find something that's got some meaning, but nobody really knows what it means, then you can define the name. It's really, you know. And that was a really pretty cool realization. Sound familiar, Michele? Maybe like, Verdence. And it does. And I remember, you know, this was also at a time where it was like people were naming things, numbers. So I was thinking, like, 1802, which was when West Point was founded, and all these things and sitting around bouncing names one day, and somebody said, Squadra. And I just took a step back, and I'm fortunate enough to be able to speak Italian, and I knew that that was the word for team, and I thought, wow, it encapsulates so much for me of who I want to be if I could. I'll tell you one other quick, interesting story about that process. So I'm working with this branding fund, branding firm, who were great, but they came back, and then we got into colors and fonts and all this stuff, and they came back with this business card proposal for us where it was like this harsh font, black and red, aggressive kind of a look. And they said, you're the general. You're in charge. And I said, you don't get it. That's not who I want to be. I want something softer. I want to be. I don't want to be that. I don't want to be the decider. I want to be the guider. I want to be the influencer. And they said, but that's not who you are. We had gone through this back and forth for hours over the course of weeks, and I said, look, I understand I paid you a fixed fee for this engagement, okay? But one of two things is true. Either we didn't spend enough time together, and you don't understand who I am, or you got it completely wrong. So if you would like, I would augment our fee here, and we could take another shot at this. And we did. They came back a couple weeks later and they said, you know, we got it wrong. You guys were, you're the sage, you're the guide, you're the teacher. And we ended up with this beautiful font and color scheme. And I've loved the brand ever since. It's a great brand. And we kind of went through the same thing. I really thought we were really close. Right on. Super Awesome Capital Wealth Management. It was just, we were, it was a close, it was a close second, close second. Verdence Capital Advisors. But you're right, it's got to say who you are. And I love the name and I love that. I love that phrase. Right? I'm not the general, I'm the guider. That's so much about who you are, who I've gotten to know you to be. And so here's Squadra. And that's what you're doing right now. I mean, of all the technical things that you do in a description of your fun, at the end of the day, you are taking startup entrepreneurs and you're guiding them. You're delivering your experience, your knowledge, but more than that, your technical capabilities, right. Your decision making. And you're really unlike a lot of other firms. So we're obviously very familiar with the whole venture space. It's put some capital and really drive, drive a numerical outcome. That's not what we get from you when we see you with these entrepreneurs. I think that's not part of it, but that's not what it is. Well, I've said, I like to say I have come to appreciate there are different ways to build great venture funds. And I think I've come back to maybe three different ways. And a lot of people mix pieces of this, but you can simply, one, you can bet a sector, if you bet a sector, and that sector massively moves up, you're going to be fine. Two, you can just simply focus on getting access to the very best deals at the right valuations and, and at that point, truly hope that those companies grow. And I think that's a pretty good product where your skillset is assessing. And clearly, we've got to have pieces of that, too. But the third thing is, you can actually think of your actions post investment as a piece of the alpha. And so when we, and for us, one of the things that I try to get everyone on my team to appreciate, I don't even in many ways, think of ourselves as investors. I think of ourselves as company builders. That is a whole different mindset. And I also would say, as you move earlier in the venture chain, it's critical. I always found it to be almost counterintuitive that the younger the entrepreneur, the more willing a firm was just to just throw money. If you look at the way a great private equity firm works, when Vista or KKR or Toma Bravo or TPG comes in and buys into a company, they don't just say, oh, let's hope, call us in a year and tell us how it went. That happens a lot in early stage venture. And I always found that to be really counterintuitive and wrong. And I would even say it happened to me as a young venture backed entrepreneur. I didn't really have a lot of experience. I was given a lot of money. We figured it out. But I look back on it and I call startups the land of 100 decisions. You know, I think, excuse me, you know, it's not, if you look at the first four or five years of a startup, there's, there's about, in an order of magnitude level, there's about 100 decisions that are material in nature, from hiring to branding to product to go to market to sales to partnerships to pricing, you know, the whole stack. And what I found interesting in my own experience was my investors, who were great human beings, didn't really help me make those 1st 100 decisions. They asked me what those decisions were at the board meetings and they're hypercritical, right. And we're phenomenal Monday morning quarterbacks in many cases, but, but you know, they didn't, and by the way, they weren't designed to do that. This is really important though, point I want to make too. That wasn't their job and that wasn't what they had sold me either. Just to be clear. They, they saw their job as, hey look, we're going to provide money for great startups and the ones that go well, you know, we're going to put more money and if they don't go well, we're not. I, when we decided to launch Squadra, I really said, let's try to engineer from the ground up a firm that would see its mission as a firm that helps entrepreneurs make their 1st 100 decisions better. That's awesome. That's awesome. And you said it From the Ground Up. This is why we really wanted to have you on for everybody listening, because we get entrepreneurs who come in and we talk about from the ground up, you're doing it every day over and over and over again, building from the ground up, taking people through that process. One day we're going to get off that ground. That's what I'm excited for is when we can actually get off the ground. Well you're doing pretty good at that. Well let's, let's take a step back. And how did you get to that point where you could be that person, that guiding light, if you will, for these new startups to make those hundred decisions. So it goes all the way back to a young italian kid who has to make this decision on going to school. And I really think it's awesome. Every time I meet someone who has gone to one of the academies and you made the decision, you had the opportunity made decision to go to West Point. Walk me through that. I think we probably have to wind back even a few years before that. I mean how I grew up, I was the oldest of three kids growing up with a tremendously tough but loving father who was not super academic. Was not certainly if you looked at his resume was not entrepreneurial. He worked for railroad and he was a big tough guy. When I was a kid though, he always, I was always sort of challenged by him whether it was like I remember being, well we didn't take vacations as a kid, you know, we didn't really have money for vacations. But one, I think I was like 13. 1st time we all loaded up in cars and we drove down from Cleveland, Ohio where we lived in the city of Cleveland down to Myrtle beach and that was where we went. We caravan down there by the way, eight of us squeezed into a two bedroom condo that they had rented for a week. You know, I don't, I don't even know how we did the things we did. But you know, like a mansion, right. And that, you know I, we literally had, we had, we had no, maybe more than eight of us. There was, I'm sorry there was ten of us in a two bedroom because we, me and my cousins, there were six of us in the living room and the two adults had, you know, the two adult couples, my, my mom and dad and my uncle, my aunt had bedrooms and my dad in the car. We get in the car, we're like driving through the night, you know, and I'm in the front seat and he says you're going to navigate, you know. And that was 13 maybe. Yeah, 12/13. You know, you're in charge of the map, you know. And, but I could give you 20 examples like that when I was a kid where it was like my dad bought dad Guy, You go put this together and, and, and you know, I was called Guy Guy as a kid. That's what all my uncles and my Guy Guy. I was very, very challenged. And what happened was, I had done extremely well in school, relatively speaking. And all these college letters start coming in. My dad would just. He always, like, kind of control the mail. So there'd be like this. This was like, this stack of mail, and I would end up with, like, some pile of all these college letters that would clear him. And then one day, I come home and there's this neatly unfolded envelope with. That's kind of laid out on the table, you know, very precisely. And it's the United States Military Academy. And I look at my dad, and I. He's, like, laying on the couch. And I said, “Dad, is that?” He said, well, I said, “what's this?” Because it was an odd presentation of this particular document. And he said, “oh, you got a piece of mail today. I thought you might be. I thought you might be interested in it.” And I said, okay. And this is, like, after 250 letters that have just, you know, ended up in piles, put in the basket. And he said, “well, I can take off work if you want to go check that out. I see they got an event, you know, next Friday.” Okay. We went down to an auditorium. I think it was at Ford Motor Company in Detroit. We had moved to Detroit. And all I watched the whole time was my father looking, like, just eyes wide open. And I couldn't. I didn't even watch the speaker. I was, like, enthralled by, like, my dad's reaction. And at the end of the presentation, he looked at me, said, “Guy Guy this is for you, buddy, that you're gonna.” And he said to me,“you're gonna write your ticket. This is for you.”Michele So it's the only school I applied to. God bless him. He knew you and he knew it. He really did. And, you know, I wanted to quit. I don't know. I mean, I could. By the way, I could be 7 hours on this podcast. But I will. I'll try not to let myself do that, but I gotta. I'll give you a good one. Did Michele give you that? Look, I didn't, but this is the first guest that's kind of gotten me teary in the first 15 minutes. I'll tell you a couple of. I could really jerk some tears here. But my, my. I come home, and I go to school. I go to West Point. I hated it. That's hard. And I missed home, and I felt like I wasn't good at it, and so I didn't want to be in the Army, really. And so I came home and I had a plan. I was going to leave, and so I wrote letters to some Ivy League schools for transfer paperwork. I actually requested transfer paperwork, and I had this whole plan. I got home at Christmas and I sat my dad down and I said, “I think I want to leave.” And it was the hardest conversation I had ever had in my life. And my dad looked at me and he said, “Guy Guy, I don't think you have enough information yet. You've only been there for four months, five months.” He said, “do two years. The only thing I ask you do whatever. But if you do two years and then you decide to leave, because that was the last point you could leave before you sucked in, I'll still be proud of you.” Wow, that's powerful. And, you know, it was a great lesson for me that I will hope to apply. At one point, as a parent, he gave me an out. He gave you an out without letting you quit. And I stuck it out, and I came back with a spring in my step, and I came back and told my buddies, I said, “I'm leaving after year two, but my dad's going to be proud of me.” And that about four or five months after that, no, maybe just the beginning of my second year is when it all clicked and then it was game on. Yeah. That's amazing. And for, you know, again, for everybody. Listen, we try to point out some takeaways here and there. It is more. You're probably prouder of overcoming that than even getting in in the beginning, right? You had it. You had the feeling. That's a moment a lot of people get to, and it's a hell of a lot easier to walk away. And your dad pushed you. You had the right guidance and you stayed with it. And how great did that feel walking down the. Walking down the aisle of graduation? It was amazing. And what did he look like that day? I mean, you know, it was incredible. And I'll tell you. So I graduated, and then I got this scholarship to go over to Oxford. It was amazing. And while I was over there, this is probably, I'll tell you one more powerful conversation about my father. He really didn't He and I were, in so many ways, so different. I didn't like anything that he liked, and vice versa kind of a thing. So he kind of stayed away from a lot of my decisioning, you know, like, didn't really try to influence me. But I had gotten over there and I was about I was on the scholarship. I was drawing a full salary from the Army at this point because I'm a lieutenant in the Army, I'm getting a stipend from the British government, I'm getting a huge housing allowance from the US Army, and I've got, like, 26 weeks of vacation a year for two years as a student. This was like I was learning that, and I'm basically making more money than he was at this point. I'm 22. So I call him up and I didn't know that. This was probably one of the kind of, one of the last real conversations I had with my father at the time. But I called him up and I said, “how much money you think I should save?” And I had prepared for this conversation because I thought he was going to tell me saved 90% of it, because that's what he would have done, an old italian guy. That's what they do. And he said, “well, what are you going to do with the money?” And I said, “I'm going to travel. I'm going to travel, I'm going to throw parties. I'm going to have fun. I had this whole, I'm going to go to Italy, where I'm going to go here, I'm going to travel Europe.” And I knew he would dial me back and say, save 75, 80% of it. And he said to me,“Guy Guy, spend it all.” And I said, I was shocked. And I said. He said, “I never took a risk my whole life.” Isn't that amazing? He said, “you're going to be my boy. That takes risk.” Isn't that amazing? That's amazing. And just so you. My father and my relationship were almost identical. He was a teacher and a juvenile corrections officer. He worked two full time jobs his whole life trying to get us by. My mother, who was italian, was home. And on multiple occasions, I would go to him to have this conversation. And to the same point, I remember the day he said to me, he was like, “Leo, I can't give you advice here. You're in a place that I don't understand.” And he didn't. He didn't understand the risk we took. He didn't understand the mentality behind that, but he was incredibly proud. And that is fuel, right? Having that from the man that not only do you look at and look up at the most, but is the harshest critic and the biggest supporter. So when you hit that just right, that's powerful. Well, I've always said, I say this to people who lose their parents. The day my dad died was the day he went from being somebody I talked to every week, to somebody who was on my shoulder every day. Yeah, yeah, yeah. I say on our website, there's a question. Who's the person you'd want to have dinner with that are alive? Always say my dad. Because you don't know the power of that relationship until after they're gone. Of course, we would have a burger and fries. We wouldn't go out for anything too fancy. So that's powerful. And your dad got you in the right frame of mind, but you did it right. He just got you refocused. And then you go through this and you. You get through West Point, which is a tremendous accomplishment. You go to Oxford, and then you start an intelligence career in the Army. I mean, this is some pretty heady stuff, your technology. You got into intelligence. You are seeing some pretty amazing things back then. Well, I think just for reference, this is the nineties, right? Well, this is. Right. I graduated 97, but I come out of Oxford, you know, it's basically 2000 when I come back in the Army. Now, many people listening to this podcast, if they were, if they were anywhere near the Army, would snicker at, you know, the term military intelligence, we always call it a great oxymoron, but it is an interesting field. What it really meant, and this was central to my own journey when I was trained as an intelligence officer. What that really meant I was trained to do was use a set of analytic tools to help my boss, who's the decision maker. So let's say you go into an Army battalion or an army brigade, and the boss is you're fighting a conventional war against the Russians or the Chinese. And if you think about the fundamental decisions that the commander has to make, he's got to make decisions on where to put his troops. He's got to make decisions on which direction to go. He's got to make decisions on which weapons to employ or which defenses to build. He's got to make decisions on when to do all these things, right? And so my job as the intelligence officer, just to be clear, is just to make sure, given all the data that we have coming in to support us, that I'm synthesizing it to make sense of it for him. Right. So it's really, it's a pretty rational kind of field, right. And it actually is one that trains you good. Pretty, pretty trains you to have to possess good strategic thinking, I would argue, in many ways, because that's what your course of action analysis. Where are my information gaps? What do I need to go do? And etcetera. So what was really interesting, though, was that 911 happened, and I was in Germany, on my way to Germany, and I had just come out of the officer advance course, and we had just gone through this long training on all these tools that we had. We had these big workstations with all these tools, and they were all designed to either do one of two things, support, like peacekeeping operations, because this is like coming out of Bosnia and all this stuff, or prepare for a war against the Russians, God forbid, the Chinese. So all of a sudden we're going into Afghanistan, and none of the To fight a counterterrorism war. None of the tools that we had were capable of even being used. So it's like imagining, I don't know, in the finance world, if you were, you know, if you had a whole bunch of tools to manage an options trading organization, you decide you want to now go into wealth management. You don't have any software to manage that, what that needed. So I happened to be working in an organization where the boss's boss's boss was this Army two star general who was in charge of the senior intelligence general for the Army, basically, at the time. And he understood this very, very clearly, and he said, “look, we're going to rebuild. We have to rapidly build a new software stack.” And he goes and puts out this note and he says,“I'm looking for young Army intelligence officers who have backgrounds in computer science, who could run software projects because we need to build new tools and we need to build them right now.” So I went to my boss and I said, “hey, sir, I think I could do this.” And he flew me, flies me back to DC, and I interview, and I get this job. And my boss, the senior guy, the two star, becomes a huge force in my life. I work for him basically for the next five years. He ends up becoming the director of the NSA. Throughout that. In that time period, I went. I went from Germany to Italy to Afghanistan, came out of Afghanistan, came back to NSA as one of his special assistants, and then went to Baghdad on his behalf. And I spent a year running what turned out to be one of the bigger projects that that agency had ever taken undertaken with respect to trying to figure out ways to use data to support offensive targeting operations. And so I had this incredible. It turned out it wasn't just the fact that I got to be an intelligence officer, because my point of that statement is, in many, many contexts, 5/10 years as an intelligence officer isn't all that interesting, I would argue in hindsight. But this, you know, for the luck of the draw, in some ways, I had this, I would argue almost like Malcolm Gladwell like opportunity where I was truly in the right place at the right time and able to seize it and able to go and do some spectacularly interesting things, working for some visionary people and getting known for being somebody who would get it done. You know, I think that's, and that's what I try to convey to a lot of people. Like I spent a lot of time talking to young Army officers today. I'm like, look, do your job, dominate your job and build, generate reputation for yourself as being somebody who can just be massively dependent on. Yeah, absolutely. I'm hearing a couple things here. One I'm hearing, so basically your job was and you developed yourself an expert in helping people make 100 decisions, right. But just on the battlefield. Right. So it's the same translation it's always been about, right? How can data drive decisions, drive quick decisions of significance? Yeah, that's a powerful skill. And also, I love what you said about the young Army officers as well. We do it with kids at a college. My son who played football, his football buddies from college will call and we have that same conversation. And for anybody out there who's just starting their career, listen to those words. I call it being outcome oriented. Right. Not being task oriented. Don't look at the person next to you. Don't look at, try to compare everything day by day. You know, don't look for the immediate gratification. If you just stay focused and all you do to your point, get things done, stay outcome focused and just drive as hard as you can for the people who, um, who you respect, you, you're going to be successful. What's just going to happen by osmosis? You're going to be successful. I would also add, you know, stay, don't ever The one thing I try to also get across there is the importance of dominating your particular job first. You know, I think the one sometimes what super smart people, the mistake they make is they see a job as maybe below them a little bit and they think that what they're going to do is prove that they can create a lot of value around their job and that becomes a really kind of inappropriate security blanket for them. And so it's like, look, I don't care. I think I learned this in the Army too, though. Hey, you get a tour where you got to be the supply officer for the battalion. Just go dominate being the supply officer and you'll have your chance to do something different someday. But you're not getting that chance if you don't dominate that. And I come back to it a lot with people where I'm like, look, I think as I progress through, I always make sure people on the team, I think when I'm, I always try to, maybe sometimes I don't always do it, but I always try to make sure that my people understand, like, what do I actually need from you? Yeah. Yeah. Well, and be patient. Right. And be patient. Be patient. Your time will come. Just keep doing it. What I always say is when you're, when you're young and you're looking out, a year seems like an attorney, two years, like, seems forever. When you get old like us and you get more gray hairs and you've been through a lot, you look back that year as your eyes blinked. I mean, it was just, it was a moment, a passing moment. So I think that's great advice. So you did that, by the way, if you could tell it quickly, you were an intelligence officer and you met another intelligence officer in the Middle East, and you tell a great story about him wanting to take you to his ranch. Well, I was asked to go. I've never told this story publicly before. I think I've told this on a golf course. See what I can talk about here. I was asked to go over to Saudi Arabia, and I spent like three weeks over there working with the Saudi military, and I built a pretty good relationship with this one Saudi colonel. He may or may not have been part of the intelligence service, but he says to me at the end, after three weeks, I don't know if you've been to Saudi Arabia, but not, it is an interesting place. And you go out to a restaurant. It's a dry country. There's no alcohol. You go to a restaurant. There's a place in the restaurant for men, and there's a place in the restaurant for women and families, and that's where you sit. I would go back to my room every night and eat a sandwich in my room for three weeks. And I was fine. I mean, I didn't really care. So the last day, the guy says to me, “Filippelli, what do you do tonight?” And I was like, “well, the same thing I've been doing the last 20 nights.” And, you know, he says, “you come to my farm. You come to my farm tonight.” And I was like,“all right, I'll come to your farm.” So

00 at night or so. He starts driving me out into the desert. And if I didn't say at one point I was a little bit scared, I would be lying. I did wonder if I had made the right call at one point on this trip, but all of a sudden, we get to the. There's a few lights that I see. I mean, we're just driving through sand, and all of a sudden there's a few lights and. Son of a gun. We're at a farm now, not a farm that you would recognize as a farm, but a bunch of camels and goats in the fire like a bonfire. And he says to me, “you are thirsty. You want the drink?” And now I realize I'm being honored. And he's probably, I'd heard, like, they have maybe a stash, maybe a little bit. Not your bourbon, but maybe some Johnny Walker or something. So I say, this is the goal. I say, “yes, I'm very thirsty. Very thirsty.” So he goes over. All of a sudden, a guy pops up from nowhere, and the guy walks, he yells at him, and the guy walks right over to the camel and milks the camel right in front of me and comes back with this warm 95 degree bowl of camel milk that I have to now honor him by drinking. And it was kind of like a vanilla hot chocolate. That's how I at least mentally mapped it as I was sipping it. Right, right. You went from the scene from Casino when they're driving out to the desert to Dairy Queen. That's amazing. What a story But it just. That story speaks to your life. I know. Guy has a great story about playing football in Europe, and he had never played in the States and suddenly found himself the quarterback for a team in Europe. And then he's in, you know, he's in Saudi Arabia drinking milk from the camel. No, I think all the events that I've had, all these events in my life, like, a lot of funny stories have come out of it, but a lot of things have not worked out, and a lot of things worked out better than I thought. But even when they didn't work out, I've always tried to make some lemonade out of the lemons. Right. Sounds like an entrepreneur to me. Sounds like an entrepreneur. Right. You take the moment, you analyze the moment, you make the best of it. Yeah. Yeah, absolutely. That's fantastic. So I drank the milk. So you drank. I think we have our title. That's pretty good. So then you come back, and not to spend too much time on these, because I think the story really gets interesting. But you did have a couple startups. You ran them well. They were successful. You had a couple exits, and. And you and I got to know each other, post read out. But pre Squadra. I'm excited to tell this part of the story. Yeah, no, I did. I had two. The first company I did was, we'll get into the entrepreneurial, maybe lesson learned here, because there is kind of a pattern of the first company I did met the pattern of I knew exactly what I wanted to do, and I knew exactly how I thought at the time I could do it well, which was I had been five years in the Army running government contractors. And I know you've got a bunch of government contractors as clients, but I had been around for five, six years, these government contracting firms, as my, you know, as my client, as my customers or whatever. I was the customer. And I was, in many ways, I was always forming opinions of, like, how I would do it a little bit differently if I was running that company. So when I formed Berico with Nick Hallam, who was my West Point close buddy, was actually my pleb. But one of my, to this day, you know, my number one, I. We knew what we wanted to do. We knew how we wanted to do it. And then it was just a question of executing. And there was obviously things we didn't know. But there was a North Star from day one. And so, in hindsight, that company went extremely well. The second company, and we sold it, and it was a life changing moment. And there was, it was. It was a very interesting journey. The second one, I did something a little dangerous, in hindsight. I followed the pattern of what I'll call wouldn't it be cool if, you know, like, investing in, like, a bourbon company or something like that, you know, and Devil's River bourbon and rye, all your liquor stores. And I, and I didn't have the. I lacked a couple things with that second guy said, I'm going to build a cybersecurity company. I'm going to sell software to hedge funds and public companies and this, and I'm going to start a new company in the middle of Baltimore. I don't. I don't know anybody here. I don't have anybody, but I'll figure it all out because I'm awesome, you know? And that turns out to be a pretty dangerous entrepreneurial pattern. And we made it a win because we don't lose. But it was a tremendous amount of effort to pull that out. And what was, I look back on it again, go back to that land of 100 decisions. It wasn't disastrous, but there were points in time where I'd say, let's say the first 30, 30 decisions I made, man, do I wish I could have ten or 15 of them back and make them a little differently. And so when we finally sold that company, I had learned so much from it, and I had also learned so much from interacting with the venture capital industry, that now, it was actually funny enough, back to pattern one, where I said, okay, I've spent the last five years interfacing with the venture capital industry as a customer, essentially. And I actually had very strong opinions of how I would do it differently. Right? So I knew I didn't have the track record, but I knew essentially what I was going to do and how I was going to do it. And, you know, again, we've learned. We learned so much every day, even now, five years later. But when we met, I came in here and told you and team that I was going to do this. And I think people, you know, and you were not unique. I think a lot of people were looking at me going, and you have no idea how complicated this is, how hard this is going to be. But I did, you know, I knew it was going to be hard and I was. But I also, I just felt I had enough intuition of that industry where I could go in and chart a path. Right. Yeah. I mean, I think if I remember correctly back then you were all right, I know I'm not retiring. Right, right. So I have to either do this again with a startup or I'm going to do this fund thing. And to your point, I have experience now and I know I can, I can deliver value to a lot of people. And I thought that was incredible and yes, difficult. And we had a lot of conversations about formation and structure and just to be clear, you were one of the truth of the matter and the reason why I am here today, I told you, I don't really do a lot of these because despite the healthy, I don't want to say skepticism, but the questions you asked me and your team challenged me on early on, you were one of the first people to back me, to support me, and I'll never forget that and I appreciate it. But it was the other point. I'll say I knew I was getting into a 20 year journey and I will tell you I'm in year five and I think that's probably true still today. I think it's going to take me another five years to get great at this and then it'll be ten years to execute hard at a level, hopefully of greatness. And then it's along that way starting to think about transition. So that's now I have to think about how do I get to. Because the ultimate objective would be to have this firm live far beyond me. And that's unique. Too often what this world is that you're in is just raise capital, hit a couple home runs, and if you get through a fund or two with big numbers, then you're kind of on Easy Street and you almost start to manage things differently because you get so much capital that you stop being the coach, you stop being the guide. And I think that's what's, there's a couple things that I've noticed about you and your management style, to hear you comment on them, and maybe the form of the question is what is it that is so different about you? My observation is a couple of things. One, what we talked about, the guiding and the coaching and the hands on delivery. But one of the other specific to this environment is that rather than go do a startup company, you're doing a startup fund, but you're, you're running it like a company, not like a fund. You're running it as an enduring company. And I think the other thing is for all those who know the kind of lead investment startup world, I was just on a due diligence call just the other day, and the manager said those words, those words that you hear in this marketplace, yeah, we'll probably knock it out of the park on three of them. A bunch of them are going to fail and a few of them will get out of there, kind of break even. And if that happens, we'll have a successful fund. And every time I hear that, I cringe. Right, that that's a successful fund that I'm going to invest in 15 companies and three are going to be fantastic. I get that those are the numbers. I get that that's the startup world is hard, but when I watch you, you're really driving at a zero fail rate. You're trying to make all of these entrepreneurs successful. And it's about them. It genuinely is about them being successful. I'm fascinated by that. You're uniquely different in that manner. Well, I think that some people would tell you that, you know, maybe there's people that would tell, say to me like, you're inefficient, you're, you're, you're allocating your time incorrectly. I've even said, if you gave me a choice and you said, guy, you, you know, you, you can control the future. I have a genie in front of me. And you're going to invest in ten companies. And scenario one, you get to have two successful, three, okay, five fail. But the two successful will be so successful that you're going to five x the fund for your investors. Okay, scenario two, you're going to have two be really good. Not, maybe not as great, but are going to be great. Three or four are going to be awesome too. But you know, at a little level, a couple of them are going to be just okay. And then the last two, you're going to get your money back. And maybe, maybe one failed and you gave it everything, but it failed and you only ended up three and a half x ing or four x ing the fund. I mean, let's even just say three xing the fund. I would rather have the latter than the former. Right. I just, it's, it would, it would, I really would. And I think it comes back to me of truly why I'm doing it. I am not truly doing it for, quote, the money, you know, I want there. I'm looking forward to being successful and being able to do things with that money and certainly be more philanthropic and help my family and do intergenerational things and all those things, that would be great, of course. But, you know, when I look at why I get up and what I obsess about and what I think about when I lay in bed at night and what I think about when I jump out of bed in the morning and what I enjoy. I enjoy. I enjoy helping these entrepreneurs win, you know, and I. And I. And I hate losing. Yeah. Yeah. I mean, the parallels divergence, which is why we're close, are remarkable. Right. We left Merrill. We left the conflicts of interest. And today in this business, we could sell products. We could start going down the road of independent broker dealer to do fee based stuff. We could exponentially increase our revenues. That's not who we are. Right. You have to be outcome oriented. You have to have. You have to have a culture. You have to have a belief system and stick by it. And here's what happens. Those successful entrepreneurs that would have otherwise failed, because they don't get the coaching, maybe their guy, Phil Pelley. Maybe the first one's okay, but then the next one, and then the next one. And I think if you always do it right, there's success on the back end. Well, I think the other side of it, for us in our business, again, we're not. It's not why we do it. But I think an ancillary benefit of it is that we will get the referrals, you know, the word on the street, over time, for us, amongst entrepreneurs, which is who we really care about, Will. Yeah. Will come back to us. It'll draw the best founders to us. Yeah. Well, I could see it in your fund one, which was successful, and you had to drive hard to get opportunities and fund two. The opportunities are coming at you because of how you treated people in fund one. And by the way, the success you've had, the numbers have been great. The successes have been amazing. So tell me a little bit. I just want to go to a couple more things here. So I look at the state of affairs today in the world, right? We have God, by the way, history repeats, right? If I sit here and I think about an asian power who's trying to take over the US, economically and otherwise, buying up land, buying up businesses, I think about Russia invading a free country. I think about a war in Middle East. I think about high inflation. I think about high oil prices. I think about protests and all of that, and the city's crime. Rep of course, we could be talking about 1980, sure. Right. And that was Japan and it was Afghanistan with Russia, and it was. So history repeats itself. But now we're getting into this interesting moment where technology is adding some real fuel behind that pattern. And so we're not to get you talking about politics or about China specifically, but, but more from the standpoint, as we look at the current world today and we look at how fast its moving and we look at where your position, youre right at that center point of how do we stay ahead of everything thats going on? How do you see this moment, especially in the business youre in? Is it a fire hose coming at you or how do you stay focused and how do we collectively manage this moment? How do you see that? Well, first of all, I, by the way, I'm willing to go anywhere you want to go politically or anything like that. But first of all, I actually believe that in many ways, 1950 to 1990 was a bit more of an anomaly in world history than anything else. So I actually think if you look at history, it has looked a lot more like what today looks like. I mean, even when you look at technology, you can look at technical innovations over time that, quote, change the face of warfare. Look at the tank, look at the plane, look at guns, right? Look at anything that rockets. I mean, you can go back to cannons, you know, so when people learn how to harness new things, it's pretty dangerous. I mean, even when you look at, you say, well, you look at the cyberspace and you realize that even within the cyberspace, here's what makes I don't, you know, the things that make current conflict somewhat unique right now, for what it's worth, there's a whole slew of things that do, though, make things unique. Number one, you have on the cybersecurity side, you have not only a nation state threat from China, from Russia, from North Korea, from Iran in many cases, but you have a global criminal threat. Now, you could say, well, that's like pirates. It is. There's an analogy there, but truly, the fact that both of those things are so strong, that's important. Second thing you have, which makes it really complicated, is you have what is unique. You have very confusing attribution. So one of the things that makes cyberspace so crazy is that we don't know, actually know. We think we know. And the best attackers make you think it was somebody else. Right. Right. I mean, if you want to go, you know, so, so that becomes really hard. The third thing that you have today is you've got, with respect to warfare, some of the most interesting things happening right now. If you even compare, say, for example, what's happening in Ukraine versus what's happening in Israel, in many ways, what's happening in Israel is, and I'm not even talking political, I'm talking military fundamentals as it relates to you, of implication of warfare and implication of technology. You have in some ways an extension of what we experience in Iraq and Afghanistan, where you have a fairly technically unsophisticated foe, comparatively, and you have a very technically sophisticated country, nation state. And you have, what we've been calling for 30 years, asymmetric, pretty asymmetric warfare conditions where, what does that really mean? It means we control, in many cases, there may be dispute on the ground, but we control the air. We control the air waves, right? Like I say, we, the nation state controls the air and that controls the airwaves. And there's, generally speaking, a pretty strong symmetric advantage of force and capabilities right now. Pivot over to Ukraine, very different. Generally speaking, you've got a much more symmetric environment from a capabilities perspective. And not to oversimplify it, but you have now a return to almost World War one, like trench type conditions, but yet you have this hugely technical battlefield that's then combined with old school minelaying. I mean, crazy conditions, right? So the implication of all that for us, I mean, for the United States, in some ways, the only real positive of this for us is that we're at least not the ones getting killed or maimed right now. And we're able to effectively observe and audit the conflicts and make decisions on how will that. Because at the end of the day, clearly China is doing the same thing. And the Russians, you can say all you want about weakness in the russian force structure, they will learn from this. You're going to face a smarter, if you ever, if it ever came down to it, a smarter Chinese threat, you're going to face a much smarter, more capable Russian threat. And you're also seeing evidence of how anyone who, and again, I say this to my, I asked my eleven year old the other day, my daughter, she said, we were talking, I said, you know, why the United States, I'm just asking her, you know, why the United States never, never gets, why you shouldn't worry about a war in our backyard? And she said, well, because we have the oceans, dad. That's a very insightful, I think I was 20 when I thought about that. Now, I know who's taking Squadra Ventures, but if we place ourselves, if we decide to place ourselves in other places, which, if we follow the history of this country, we will. There's some very, very, I don't want to say scary, but very, very concerning things that we're learning. And it's going to have massive implications. It is having massive implications right now in the way that we're buying and deploying things so that in our, and again, our business. Why is that all important to me? Because it affects the kind of startups we invest in. Because we're investing in these companies that we think will add value in that progression. They're just on that lead edge. Just on that lead edge. That's. That's right. A couple questions just to, you know, hit a couple main points that I think really speak to who you are. I mean, we've heard you about a leader. We've heard you. Your history is remarkable. Your company is, is building all these great entrepreneurs, but not just entrepreneurs, not just people making the new widget to sell, but people are protecting us. People are serious in the, in the, in the community. You're serious about. You mentioned your philanthropic wish. You want to have a moment? You want to do more with philanthropy. You went to West Point. You were in the Army. You're around that constantly. And I know you are committed to a foundation called Commit Foundation. Yes. And it's one that I didn't even know about until I saw you online one day on a video, and I immediately decided to send something over. You were very convincing because it's an amazing foundation, but it's one that flies under the radar a little bit. And even though veteran charities are so important to everybody right now, and I think probably we have more attention to it than we've seen in a long time, there's a group that's getting missed, and that's who you're focused on. Yeah. Thank you for asking about Commit. I have a, I have some strong opinions on the veteran space. I think that could come off in main, I don't want to say controversial, but they could be maybe misperceived if I don't qualify it properly. When I look at the veteran space, I think this country has gotten extremely. We all care about soldiers, sailors, airmen, marines who have given their lives or their health, if you will, to this nation. Right. And there are a lot of, you look at the conflict in Iraq and Afghanistan, you look at the thousands who were killed, you look at the tens of thousands who were injured. You look at, and even beyond that, those who've had their families screwed up from men and women continually deploying overseas, putting their lives at risk. However, I also believe that if you look at the pool of veterans who deployed and served in those conflicts, you're talking at this point of millions of people, right? Many of whom came back. So when I look at my peer group of people I went to West Point with or soldiers that I serve with when they got out. And if you were a, if your son joined the military and served for 4, 5, 6, 10, 12, 15 years, deployed to Afghanistan, deployed to Baghdad, kicked ass, gave his heart and soul to his nation, had the hardest jobs, did the hardest things, did amazing, got out, and he's ready to go into the next phase of his life. Okay. And what's out there to help him? Well, he's not physically or mentally wounded, and so he's not going to wounded warrior. Right. But this is, so there's nothing, there was nothing out there for him or for her. And so that's where there was a, there's been a few. I mean, we're not the only one Commit is, I would argue, one of the best. But there's a couple others out there. Honor Foundation comes to mind. But these are organizations that focus on helping incredible high potential, high performing men and women who have all dedicated themselves to their country for a certain period of time, transition to the next phase of their life aggressively. I always like to say, how do we help make the next greatest generation? Right now? Giving money to, again, this is where it gets confused. Giving money to Wounded Warrior. I'm not saying don't give money to Wounded Warrior, but what I'm saying is that's a very small part. I'll ask the question. I'll say to people today, I said, how many Americans soldiers were wounded in combat last year? And people will say, I don't know, like, people guess, they'll say, I don't know, 5000. I'm like, where? You know, maybe five. And you don't even. We can't even talk about them because they're not deployed anywhere that we're aware of. Right. The truth of the matter is, how many soldiers transitioned out of the military last year healthy? 200,000. 200,000. Okay. So now I also fundamentally believe that the tilt towards patriotism around wounded veterans is also hurt the desire of parents to send their children to a military academy or join the service. And so I actually think there's counter productivity to it. So anyway, I'm on this sort of, I've always, for the last ten years, been very, very passionate about helping men and women, I like to say, accelerate out of their military career, make the first hundred decisions. Well, and that's what it is. And so if anybody is ever interested in learning more about that stuff or being a part of it, like we've got, we just hired this incredible new CEO, JC Glick, who's came out of the Ranger Regiment and had his own incredible, you know, interesting transition. And it's just this ball of energy. And he is so passionate. He is built for this job. We serve about a thousand veterans a year. Like, we affect the lives of a thousand people a year with this foundation. It's pretty cool. And we're going to do more. And so that's Commit. We're going to do an event in Baltimore. I'd love to have you a part of it in some way. Absolutely. Absolutely. Commit to it. I'll commit to it right now. Absolutely. And I love that concept. Right. So create successes, show the successes, and more people will want to be a part of it and bring people. Bring people. My wife's sister's fiance, Justin. Hey, Justin. He served. He was helicopter pilot. He was in the mix in a couple of bad places. And he's transitioning through and going to school. Yeah, I mean, all the help you can get is. And he's not a, you know, again, yeah, he probably, he's not a Wounded Warrior. You know, I go to these events sometimes and I. He still lives. The fact that his whole life was surrounding 100% not just what he was, not just that he was there, but having, having regimen lifestyles. And this is when you eat and this is where you go, and this is what you do, and then suddenly you're just like, okay, go ahead, go make a living. Well, they, the, there's a lot of parallels. Like, I know you're in the sports world. There's a lot of parallels professional athletes go through when their sports career is over. There's this existential point in life where it's like, what now? And that's a pretty harsh drop off. So that's 100% there. But I think that when I go to an event that's a military type event and let's say there's a military nonprofit raising money, it's, you know, I don't, it's a lot, it's sort of the easy button is to parade a veteran on stage who's lost his leg or his eye, and it tugs at the heartstrings of everybody in the room. But I, but, but I, but, but again, I, but I don't think it represents the greatness that beyond that part of the spectrum. And it doesn't, again, for me, it doesn't motivate people in that room to actually embrace the military. It employs a degree of almost guilt. Oh, I didn't serve, so therefore, I better support with my check. And I've always sort of just been anti that from a nonprofit perspective. I'm like, look, I just want. Want people to invest in making America better. They are a great piece of a much, much bigger situation. I'll say one other thing on the veterans and post service stuff. Look at. I don't care what party you're a part of. Veterans in Congress are the glue that's going to hold this nation together, because they may not believe in what each other believes in, but they respect each other enough. Cause they serve together. That's right. And there's. We see that every day. I was on a. One of my good friends who actually used to work for me, Pat Ryan. He's a congressman in New York. I was literally in a room with him last month, and he was with Rob Whitman, who's a congressman from Virginia. And you could tell they're friends, you know, Republican and Democrat. I mean, we look at. We need more of that. And it's why I'm so. Yeah, we need more of that. It's why I'm so deeply. I'm such, you know, again, not why I'm such a deep and passionate supporter of Wes, of our governor here. It's because. Not just because his policies, but because of the human being that he is. And, you know, I was very proud to support him and host some events for him and stuff. And I remember the first. One of the first events that we did at our house. I basically stacked the entire room with Republicans, and I told him that, and he walked in with a smile on his face. And so I think there's something about. I think a lot of that traces back to military experience, because you walk into a platoon. I remember my first platoon. Nobody looked like me, nobody thought like me. And, you know, it takes all of about an hour to start to see the beauty and all that. Yeah. Yeah. Incredible. I have one parting question. This one's a serious one, so get your head around this. You get a call to national cooking contest. Mm hmm. Guy is an expert chef. You gotta make one dish. It can be pizza or it can be meal. Walk me through what's gonna win. One dish. What's gonna win. What's the guy Philippelli, winner. That's gonna differentiate you from the. From the crowd? I mean, it's such a tough. It so depends on the day, what's going to differentiate me from the crowd. You know, I would probably. I would probably revert to a pasta that I learned how to make when I was in Italy. And when I was, you know, even though my grandfather, you know, was born in Italy, came to America as a young boy, our family lost touch. When I was 22, I wrote 400 letters to everybody in Calabria that had my last name looking for my relatives, and I found my great grandfather's youngest brother still alive. I mean, there's so many more stories to tell here. But I went over there, and I lived with this family for several weeks, and I call her my aunt. She just passed away last year, by the way, in her nineties. But I stayed with her and her family, and she made an extremely simple pasta. And in the south of Italy, in Calabria, they don't even use egg in the pasta. Flour. It's just flour and water. But they make these incredible shapes, and they don't use rolling pins and they don't use machines. It's all rolled out by hand. And they take this reed, like, basically a plant reed that they dry. And you learn how to make what you would think of, like a bucatini kind of a thing where there's a hole in it, you roll it out. And I would make that because I would enjoy the process of making it, by the way, and I would get really emotional, just like I would, by the way, I would do it for me, I would enjoy that process. And I would just make a nice, simple, nice simple sauce along with it, with the right amount of cheese. And that's. That's the dish. Yeah. We used to do the regatta and yakis, but we would. We would. We would put the finger right in the middle, roll it back. So almost cavatelli. So it was. Yeah. Well, there you go. I always. For some reason, I keep finding my way back to food at the end. Michele, I don't know why. It's definitely a theme that you have there, but that was. I'm drooling I'm like, wow, I know we're making italian tonight. Well, also, I would. I would also full disclose I was over been the guys. And his pizzas are off the charts. He has a pizza oven that gets, like 1300 degrees, and the pizzas take about two minutes to cook. And they're magnificent, and they're true italian style pizza. We'll have you back. Well, guy, this was fantastic. Thanks for coming in and spending some time telling us some stories. I feel like we should do three more of these. You have so many great stories, but I think what I'm most. What I take away from this conversation is what I know about you, and that is you're passionate about whatever you put your mind to. You're passionate about the love for your family. You're passionate about your cooking. You're passionate about your Italian heritage, about your service to the country, about the people who've come after you. And you're passionate about your business. And what I think makes me proud to be involved with squadro is you. And for those listening guys, communications are detailed and they are fantastic. As an investor, it shows that he cares about us, and what's written in there shows he cares about the business owners. And I just think your passion is your story, Guy. And I really appreciate you being here. Thanks for being on From the Ground Up, and I thought it was fantastic. Thanks for having me. Absolutely. Yeah. And I also want to thank you for joining us. And one word comes to mind that I keep hearing over and over again, and not to sound cliché, but you're invested. You're invested in so many different meanings of that word. So it's been a pleasure to talk and hear your story. Thank you. And speaking of invested, listen to the Verdence Capital Advisors podcast on Spotify, YouTube. Let's see if we get it right this time. Michele and our website, that's. You got it. Yeah. And we will have video. Thanks, everybody. And thanks, Guy. Thanks