Life on Mars - A podcast from MarsBased
Life on Mars - A podcast from MarsBased
Road to CTO #1: From economist to coder: why Charles Chase never went back to corporate
In this episode of Road to CTO, we sit down with Charles Chase, a serial entrepreneur and investor, who shares his journey from aspiring accountant to building multiple successful companies, including Velocify. Charles reveals how a pivotal moment in the late 90s sparked his passion for programming, leading him to abandon his original career path and dive into tech.
Despite mastering coding, Charles chose not to follow the traditional route into CTO roles. Instead, he embraced operational leadership, seeing company-building as a form of engineering. He believes creating systems, processes, and teams requires the same careful design as good software.
Now based in Barcelona, Charles shares his unique perspective on entrepreneurship, emphasizing the psychological qualities needed to succeed. His investment philosophy focuses on the person behind the product, prioritizing vision and problem-solving over the product itself.
🎬 You can watch the video of this episode on the Life on Mars podcast website: https://podcast.marsbased.com/
Hello everybody and welcome to Life on Mars. I'm Alex, ceo and founder of MarsBased, and in this episode we bring you Charles Chase, a serial entrepreneur and investor who created companies like Velocify, affinity and many other ventures, and we discuss with him his career as a serial entrepreneur and how to become a technical co-founder or a CTO, even though he has opted not to be a CTO in many cases, even though he taught himself how to code. He taught himself how to be a technologist, but he only served as a CTO in one case in his career. But we discussed this and more of that. We discussed also building companies, investing, the differences between the US and Barcelona, and how to be a newcomer to a startup ecosystem. So, without further ado, let's jump right into this episode and then, you know, you tell me about your arrival on St Geordie Day last year.
Speaker 2:Yeah well, first of all, happy St Geordie Day last year. Yeah well, first of all, happy St Geordie Day. If any of my American friends listen to this, I guess you can correct me, but my understanding is St Geordie Day is kind of like Valentine's Day and maybe some other stuff wrapped in one, and my son, who goes to a Catalan school, is learning the story of the dragon and how the rose came about. But the cool thing for our family with St Jordi's Day is, you know, before we decided to move here, we came and did a. You know, we had been in Spain a number of times and we knew we loved it. But we came to revisit and see the schools that our kids might go to.
Speaker 2:And that was on St Jordi's Day and it was not a great day to fly in because it took about an hour and a half to get here in a cab, Because if you're in Barcelona on that day, the whole city is just like it's not an official holiday, but it's like a holiday. The streets are crazy, Anyway. So today, waking up and seeing everybody celebrate, it was really kind of special for our family.
Speaker 1:Well then, welcome to Barcelona, Welcome to Life on Mars. Actually, thank you for agreeing to do this. I really like your profile. We met a few months ago, just to give some context to the audience. We met a few months ago and your profile is very interesting because we oftentimes we get a lot of American expats coming over to Barcelona, right, but rarely ever they are on the technical side of things.
Speaker 1:Usually, you know, retired investors or people more like on the CEO slash CFO, more like on the business side of things, right, or ex-VP at a given massive multinational, ex-vp at Apple, ex-vp at a given massive multinational, ex-vp at Apple, ex-vp at Vodafone, or something like that. But in your case, like well, we should. I think Barcelona is in severe demand of more experienced serial founders that come from the technical side of things. So that's why I wanted to highlight a little bit your career, if you're up for it. So where do we want to start? Do you want to give some? Highlight a little bit your career, if you're up for it, so uh yeah where do we want to start?
Speaker 1:do you want to get?
Speaker 2:I don't know if you remember how we met. But basically, when I got here, I really wanted to understand what the technology kind of startup ecosystem was. So I think I googled barcelona startups and startup grind came up. Your name came up. I think I sent you a cold email, correct, and, and. So, yeah, you're my friend, you're my first, you're one of my first friends here and one of my and certainly my first kind of like startup friend, and, and, and, and you've been so generous and introduced me to so many cool people and and and and taking me to events, and so, um, yeah, it was just I. I've spent so many years, um, building things myself and being around other builders that, um, when I got here, I just wanted to see, see what was happening and who was building what, and um, it has I there's.
Speaker 2:There's so many surprises that I would never have guessed. First, of how vibrant the community is here, but also just the insane amount of opportunity given so many factors that we can talk about in from investors and how they look at the market, and I think Barcelona and Spain, I in general is such like a. It's such a like a underdog market, like. I think if you look at Europe, you know, everybody thinks about Berlin and the UK. But there's so much cool stuff and there's so many amazing founders here, but yet my sense is that they're undervalued. And so, you know, the entrepreneur or the early stage investor in me is like oh my gosh, that's an amazing opportunity for me because you know I can do things and maybe I have a competitive advantage.
Speaker 1:You know, so that's cool. This narrative sort of brings me to one of the realizations I've had over the past few years, which is Barcelona has the potentiality and the capacity to become a tier one startup ecosystem. Yet I think it's better if we don't. Right, why? Because you know it keeps valuations down. It keeps the cost of talent down as well. It keeps the cost of talent down as well. It brings other founders to initiate and start up their new companies here, precisely because the cost of starting up is lower than in other vibrant ecosystems.
Speaker 1:At the same time, you more or less get everything you would get from every place else. Maybe you don't get tier one else. Maybe you don't get tier one, um, I wouldn't say talent, but maybe infrastructure like you would get in silicon valley, you would get in london, you would get in tel aviv or berlin and stuff like that. But it's a trade-off, right. At the same time, it's kind of like where do you want to be? Like the small? The small fish in the big pond, the big fish in the small pond, or you can be like a really cool fish in the best motherfucking pond of all time. Right, and that's where I think Barcelona should place itself.
Speaker 2:Yeah, yeah, I mean, the people I've met here are so motivated and so smart, and I've only been here six months, so I can't imagine where we go from here.
Speaker 1:Tell me more about your arrival, because actually your story sort of resonates with mine. When I arrived first in the US, I didn't know anybody, so I called email people, one of which was people at Startup Grind, but the other people I messaged I remember the first people to respond to one of my cold messages. I arrived in San Francisco on Christmas Day 2013, and I called a message from the plane the Barcelona San Francisco Association, something like that and a very high-level person replied to me and first I didn't holy fuck, I'm meeting this guy tomorrow and he was like a VSTOPTR VC serial founder, like chairman of 27 associations, stuff like that. And so he said I got 30 minutes for you, miguel Valls. I'll never forget the name. He opened me the first doors in San Francisco, which in turn, they open more doors.
Speaker 1:So that first contact, it's always very important. That's why I try to be that kind of person, even though I'm not high level, as he was. But I try to open the doors to somebody else because you never know right. Most of all, I like to be an ambassador of my own city. So, but you took the first step, you called, message a few people to see what was going on. So what's the thought process behind? Like I'm going to reach out to tech leaders in the industry.
Speaker 2:Well, I mean the kind of stepping back the you know the impetus for us moving to Spain, and so you know I'm married and we have three, three kids and you know the impetus for us moving to Spain was really about trying to provide our kids a maybe a broader viewpoint on the world. You know we were the kids had first grown up in Los Angeles and then during COVID, we had moved about an hour and a half south to a really small beach town called Solana Beach in San Diego, california. It's a really idyllic place to grow up and to have kids, but it's a little insular, right. If you never left, you would not really understand or have a very broad perspective in my viewpoint. So we had come to Spain a number of times. My wife's sister is married to a Spaniard, so we've spent a lot of time here. So you know there was a window. You know you need these windows right. Like during COVID, there was a window and that got us to San Diego.
Speaker 2:Like during COVID, there was a window and that got us to San Diego, and the window that brought us to Spain was my oldest was about to start his freshman year in American high school, which is this really kind of seminal, important time in a young person's life and I knew that once he started high school in the US it would be hard to kind of get out at high school in the US. It would be hard to kind of get out. But we slowly started this conversation when he was still in eighth grade, which is, you know, kind of the end of primary school there, and he was all for it. My oldest is really adventurous and if he wasn't adventurous and if he was really set on staying there, we wouldn't be here, right? Because the kids had to buy in. So you know, we came out here and when we came out here I wasn't working on any projects. I was.
Speaker 2:You know, I basically tell people I'm on sabbatical. You know, I can't tell I'm 50, I can't tell people I'm retired. I can't tell I'm 50. I can't tell people I'm retired. And so we got moved in and my wife and I have went out and were tourists in the city for many, many days. But then I felt like, okay, I need to start meeting some people.
Speaker 2:And so I'm a builder, I want to build things, I want to support other builders, I want to hear about what people are building. I just I like I don't know, I like geeking out on things getting built. You know it's been that way my whole life, right, like when I was a kid. I just love building things and whether it's software or Legos or a company, I just it really excites me and so I just wanted this, I wanted this like here and see like what are people building here? Obviously, I know about some of the big companies, like global and stuff like that, but I'm much more interested in like what's that one person, that one guy or girl building that they're really passionate about? And that was that was the impetus for for trying to get into the ecosystem, because I need that part for my spirit. I need to be part of the building of things or hearing about it, and that really fulfills a big part of my professional life. That was the impetus for that?
Speaker 1:how do you become a software engineer? When did you want to start like programming, coding?
Speaker 2:uh, take me back to that, yeah time so I, when I was in college, um, I studied economics and accounting and I was really set on becoming an accountant and a CPA. I actually graduated college in 1996, and I had a job at a big accounting firm called Price Waterhouse, and what happened was I graduated a quarter late, so I was, instead of graduating, travel around Europe were, you know, not going to happen. So my father had a software company. Although my father was not a software engineer, he was like a marketing guy and actually a really good product designer, and so he had been working in the software business actually since the 70s, before there was even really software.
Speaker 2:He was doing all this consulting and then they had their first software was on the mainframes, um, and so in 97, um, his company was thinking about taking their, uh, their their software, which was like a very kind of traditional client server where you had, you know, these kind of fat clients probably getting too technical here, but you know you had a bunch of software installed on a person's computer that talked to a server, and my brother-in-law, who was a CTO at that time, kind of got this idea or got this inspiration to create a web interface, and if you think back, this was super, super, super early. So they were going to create a web interface for their product. They were thinking about doing it in like 96 or 97, which was really, really, really early, and so I went there to help them, not in a programming role, but like in a I don't know, just a do-anything kind of role, right.
Speaker 1:A webmaster. We called them webmasters back in the day.
Speaker 2:And I just got interested in the. I got interested in the building and actually my brother-in-law who I owe an incredible debt to, basically one day gave me a book on HTML and I went home I read this book on HTML. I was like okay, cool. And then he set me up like a little sandbox and I started building little HTML pages. Then he got me a book on JavaScript and I started reading that, started doing that, and then I think the thing for me the big like aha moment was I don't know if you remember, but Microsoft used to have this web server called Internet Information Server IAS.
Speaker 2:Yeah, and they had this technology called Active Server Pages, asp, yep, and with ASP you could from a web page, make a call to a database, query the database and then write to the page a table or whatever right. I'm getting goosebumps just thinking about it now, because the first time I saw that happen which was probably in like 1997, 1998, that I saw this thing happen it was like black magic. It was the coolest, freaking thing I'd ever seen and I was hooked. Like that was it. I was hooked right then I was like there's no way I'm going to be an accountant, I want to be a programmer. So I called Pricewaterhouse, I told them I wasn't coming to join my audit class and I just dove in headfirst and basically my brother-in-law just kind of mentored me and he let me play around and he taught me and back in those days, like we would, there was no stack overflow, so we would buy books. So you would buy. I don't remember like Rocks Press had these. Remember the red Rocks Press books.
Speaker 2:I have a library of them and you'd buy one on kind of everything. So I stayed with my, my dad's company for a while but, um, you know, for for one of a number of reasons. Uh, you know, working, working with your father is not always the easiest thing in the world.
Speaker 2:So I really wanted to be a programmer. So the way I kind of got into being like a real professional programmer was um, there was a, there was an application for a job at, um, at, uh, at a web, a web I guess they like a web design company in Venice California, classic kind of web 1.0 startup. It was a converted, uh, converted loft and um, the requirement was you needed to, like you know, be an expert, an expert in VB and ASP. And I just literally bought books on Roxpress, learned as much as I could, somehow survived the interview and then I just learned on the job because the guy next to me was doing something and he was cool and he kind of taught me on the job and that was it.
Speaker 1:And from then I just was self-taught, or reading or learning and and loved every minute and never looked back and that's one thing that hasn't changed over the years is you're asked like tremendously difficult technical questions in the interviews, yet on the real job it's kind of like squashing bugs and moving data up and down, and that's it like no. Yeah, yeah, yeah, you data up and down and that's it Like no.
Speaker 2:Yeah, yeah, you just figure it out. But that that was my first. That was my first experience and and and I don't even think that job is, is, is is even like on my LinkedIn. But this is like. This was my first kind of real job being paid as a programmer, and I was as happy as you can be and and I knew right then that I had gotten really lucky. I feel like I've gotten really lucky in my career because, you know, when I started my professional career, the web was just taking off and it's like if that wasn't happening I'm not saying that I wouldn't have been happy as an accountant, but like I'm so blessed that the timing worked out, that I was really starting my career when the web was really starting to blossom and I just got to ride that wave and and and see, see it from the beginning, or close to the beginning.
Speaker 1:It's. It's funny, there must be something in the water of like the big well, like the big consultancies that they create the best entrepreneurs. Not because we went through them Some of you even skipped them altogether but they kind of like scare away some really good talent that they probably wanted to join them because that's where you forged yourself right In the flames of consulting and whatnot. But then it's like no, I really don't want to do this, so I'll create my own business instead. I'm ex-Devoid so I can relate to that.
Speaker 2:I mean, I also think it has a lot to do with how things are at home when you're growing up. I think you know, when I was growing up, I saw my father always had his own company and so I just assume that that's what you did. I assume that everybody was an entrepreneur. I just assume that that's what you did. I assume that everybody was an entrepreneur. If I had grown up in a house where my parents were lifelong, were lifers at GE or some huge company, maybe that's a path I would have taken. But I think a lot of this is formed by the things you see and hear at home.
Speaker 2:You know like another one is that when we were growing up, you know my dad had gone to Stanford Business School and so we would always go back to Palo Alto, to Stanford, for football games and reunions and stuff. So even before I went to college I knew I was going to go to business school. I knew I would get my MBA, maybe not at Stanford, but it was kind of one of these things where it's like it was just it's. It's something we talked about a lot and it's something I saw and I I just I knew from a young age, even if I go and become a programmer, eventually I'm going to go back to business school because I don't know. I just thought that that was sounded like a cool thing to do and that was all. That was all kind of brought to me from my father, and so I'm very lucky that I was.
Speaker 1:I was brought up in that very entrepreneurial environment it's funny, everybody my family was an entrepreneur to you and that that was the reason why, precisely, I didn't want to become one, because I saw them all like you saw this failing. Yeah, I saw the struggle, I saw the grind and I saw them like being like all the time, like having to suffer the highs and lows and more lows and highs actually, and having to fire people downsize the business every two or three years I'm like fuck, no, I don't want to do that.
Speaker 1:So it's funny how two different just no, it's interesting you say that.
Speaker 2:it's really interesting. You say that because my father went through the same thing. My father had incredible highs and incredible lows and we basically only my father's business survived because my mom always had a steady job to even out the peaks and valleys. And I, even though I saw that I probably just didn't, maybe I just didn't like process enough, and now that I look back it's like, oh my gosh, like there was such.
Speaker 2:I now know where the peaks and the valleys were, not because like there was any suffering or anything, but like I do know that he went through that grinder and, um, you know he never had like incredible success, but but like he just made it work and and and, uh and and was able to kind of grind it out, um, but but and and. And. Also I will say like I've realized over the years that to become an entrepreneur you have to, or the start of business you have to have like this really irrational naivete about you, like you honestly have to have something wrong with you because, like, because no, I've realized this Like you have to.
Speaker 2:you just have to have this irrational belief that somehow you are going to solve a problem that others can't. And if you think about that rationally, it's, it sounds crazy. Um, and and so you know, I've actually found that the older I get, maybe, the more rational I've been, which is actually not good for me as an entrepreneur, because I'll talk myself out of doing things before I even start, which is totally the wrong thing to do. And, and, and, and and uh. Luckily, when I started my first company, I was so naive that we could do something that we, we were able to do it. And, and it's crazy, you, you really have to, you have to like.
Speaker 1:It's crazy, you really have to, you have to like, you have to have something a little off. I'm convinced we're neurodivergent people right.
Speaker 1:Yeah, and, by the way, I'm the same like. I agree with that. And there's another thing. One thing that strikes me as very interesting from your profile is that I didn't know that you wanted to be an accountant first, but that intersection of business and technology, that's where the most interesting profiles appear. Let me rephrase this Basically most of the people I admire the most in this industry are people who are both technical and they speak business, maybe they come from the technical side and they learn business, like in my case.
Speaker 1:Maybe they come from business but they taught themselves how to program. And then this intersection it's very obvious there are not so many people that can be both a CTO and CEO right or COO in your case, like when you were mentioning your first company, I'm assuming Vel and CEO right or COO in your case, like when you were mentioning your first company, I'm assuming Velocify right. So if you want to take me back to when you started and how did that come around?
Speaker 2:Yeah, so what had happened is so I was. I had some great roles in engineering as a, as a just a programmer, but, like I said, I kind of always knew I wanted to go back and get my MBA and so when I went to, I went to business school at USC for my graduate degree, which is two years, and after my first year I was convinced I wanted to go into venture capital, which is looking back.
Speaker 1:It's the craziest fucking thing I've it's so fucking idiotic what happened After my first year of business school.
Speaker 2:I really wanted to be a venture capitalist and so I was very involved in the. We had a club at school called the Entrepreneurship and Venture Capital Group. It was kind of like one group together and our mentor was the head of the entrepreneurship department and he knew a guy. Every great story starts with somebody knew somebody, right? So, like my mentor, this guy who was running the entrepreneurship department, he knew a guy who we would call him today an angel investor, but that term didn't exist. So this was 2002.
Speaker 2:So this guy, his name was well, I won't say his name, but we would consider him an angel investor. He was a guy who, with his own money and maybe some external investors, was going out and investing in startups by himself, supporting them, helping them, sitting on boards, helping them work through all the nasty problems everything from like personnel issues to legal stuff, to raising capital and so I got an internship with him in the summer between my first and second years of business school, and it was an unpaid internship and a lot of other people in business school were getting proper internships where they're making money. I remember my girlfriend at the time thought I was the stupidest person in the world because I was like I'm going to go work for this guy for free Nobody works for free, but I don't know. I felt like I needed to just get this experience. And it was really good because I basically just shadowed this guy for three months or two and a half months and helped him with modeling and helped him with investments and helped him with docs and was on calls with the lawyers. But, more importantly, I sat in all these meetings with all these entrepreneurs and I learned something really important that summer, which was I didn't want to be the investor, I wanted to be on the other side of the table, I wanted to be the guy building, because those guys were the ones who were having the fun.
Speaker 2:And so when I went back to school in the fall for my second year, I totally changed my perspective. I was like, Nope, I don't want to be an investor, I want to be. I either want to start a company or I want to buy a company and grow it. And that totally changed my focus. And so the way that Velocify which previously was called Leads360, the way that company came about, was while I was in business school. A close friend of mine and I were doing some consulting just to kind of keep the rent paid, because when I was in business school full-time we're not working USC was a very expensive school to go to and we were doing all these different kind of consulting projects. And, as every great story starts, my friend knew a guy. And what this guy?
Speaker 1:knew was.
Speaker 2:This guy knew people buying mortgage leads. So this is 2003, 2004. And you were surfing around, you'd get served with these different ads to refinance your house or to get a loan to purchase a house, and this was big business. These leads were being sold and it was a huge business, and what I came to find out was that there wasn't great software to manage these leads. Actually, we knew a guy that was buying a lot of leads and he was actually trying to use Salesforce, which you know, if you know Salesforce. Salesforce is like the seminal B2B CRM, right for lead management and sales kind of pipeline management. But the problem he had with Salesforce was Salesforce was really meant for a B2B sale, which a B2B sale is like a longer, slower sale, whereas trying to convert somebody who just clicked the form on the internet to get you to do a loan for them was a very hyper, hyper fast B2C transaction, and so you needed a different type of product for that. And so I don't know. This guy just described this problem and the light bulbs kind of went off and we said well, we can solve that, we can create basically a B2C version of Salesforce, which is the best way to sum it up and we said okay, we're going to create this company. It's going to be called Leads360. We're not going to sell leads, we're not going to be part of the selling of the leads, but we're going to create a web app and we're going to get the people who pay us for the software to tell the people that are sending them the leads hey, don't email me the leads, send them through Leads360 and my salespeople will be on the Leads360 app and when a new lead comes in, it'll pop up and they'll jump on the phone and they'll try and convert these guys. And that basically started.
Speaker 2:August of 2004 is when we kind of got that inspiration and we had a really good group of people. There were actually four of us at that time. What happened is there were three of us guys who were kind of talking about doing this, and originally I was thinking about being the CTO USC. I paid all this money to learn how to I don't want to say not be an engineer, but to learn how to do things more than just be an engineer.
Speaker 2:So I was like I can't be the CTO on this. We need to bring in somebody who really is better than I am and who knows how to do this stuff, because I was a little bit removed as well. So we actually went to a very close, another close friend of ours and recruited him in and so the four of us kind of set about and again we had this naivete that we could somehow solve this problem and through, honestly, like a lot of wind in our sails because, despite what people tell you, you need a lot of wind in your sails that you have nothing to do with. There was a lot of wind in our sails and a lot of things went right for us and we had a lot of success and that was kind of our first experience building and it may be kind of hard to see through the camera, but I've got a lot of gray hair and I probably got half of those gray hairs working on that company.
Speaker 1:Do you remember the tech stack, the initial tech stack, and is that something that changed over the years? Yeah, it was NET.
Speaker 2:Yeah, it was NET. It was NET and ASPX. The database was. I think it was actually IIS was the database? No, iis was the web server, the database, sql server, stored procedures, all that kind of stuff, wow, blast from the past.
Speaker 1:Oh yeah, that tech stack still haunts me at night.
Speaker 2:Yeah, but it served us okay, I mean it served us well and it worked out because we were able to get there was a lot of engineers who knew that stack and we were able to get get a good team around it, so that's great um, but it's funny that you sort of intentionally remove yourself from potentially being the cto of your own company, right, and let me, let me.
Speaker 1:Let me tell you why, like most engineers, most software developers, they dream of becoming a cto, right, and that's why I wanted to cover these today. Um, I've got the feeling that not enough podcasts, no, there's not enough content on how to become a cto. It's kind of like people simply become one cto. It's like angel investing. How do you become an angel investor? There's not not a lot of literature out there. You either are one one or are not. It's binary, right, but the CTO is much more complex. The CTO is a gradual process. Of course, you can label yourself as a CTO of your own one-man show if you create a company and I'm founder and CTO Well, yeah, a CTO of what You're actually writing code. But you could have been the CTO, but you decided to take on this operational role, maybe because you were sitting at the intersection of business and technology, right, and then, with Affinity, it happened again. You also were not the CTO. So is that also intentional or what happened there? Why did you choose COO of all the titles available to you?
Speaker 2:Yeah, I mean I think so I'm not a huge fan of the titles or labels. I mean I love building and in some cases when I've built things I've been the most technical person there and great. So then give me some technical title, right? And, by the way, like I don't consider myself some great CTO Like the size of teams that I've managed had never been terribly big, and being a good CTO takes skills that, honestly, I don't even really have right, like I'm probably a much better engineer than I am a CTO. Because I'm probably a much better engineer than I am a CTO, because once you're a CTO of a large organization, your role is so much more about management and people at any of those kind of C-level roles, right.
Speaker 2:And so I always thought of myself as an operator, like I. Just so, when I got out of business school and I said, hey, I don't necessarily want to program, it wasn't because I didn't want to build, I just didn't want to build software, I wanted to build a company, and I look at the two very similarly. I want to do it in an efficient way, I want to do it in an elegant way, I want it to be able to scale right, like I look at building a company the entity, the people, the processes, the products as exciting as building, you know, the actual software, right, and so operations to me always just felt like something that suited me, and and and so, and so I I've never really considered myself like a, you know, like a technical co-founder. Um, because I always wanted to have a really wide perspective. I want to, I want to be part of the strategy discussions, I want to be part of the legal discussions and, yes, I want to deeply understand the technology because and yes, I want to deeply understand the technology because there's actually I have this need to really deeply understand anything I do it's like a real kind of psychosis want to understand the technology down to the, as far, as close to bare metal as possible, because it just helps me. I just feel like I need to do that to understand the business as a whole.
Speaker 2:But I don't necessarily want to be the tech person. So like I've been in roles where I am the tech guy, but but even in those roles I was still with the CEO on strategy and all these other things because I've spent so many years and I've seen so many situations from every aspect of company building. That it's like to kind of to silo yourself and say, okay, I'm only going to be working on the technology to me was just never going to be fun, right. And so, like, even as an investor right now, like when I look at at companies that I'm trying to invest in, I have an advantage over a lot of investors because I can deeply, deeply understand the technology. I mean not every technology, I mean some of the stuff we've talked about at your quantum computing is a little bit over my head but, but I can at least grasp what we're trying to do here, but then I can have thoughtful comments on all these other pieces of the business.
Speaker 2:So I think, if you look at my career, the one thread that has gone through all of my experiences, that is that there has been there. There's technology, and I've gone kind of in and out of these engineering roles. I mean, um, I think, um, building software is something that I'll probably always love. I I don't kind of know how to do it anymore because I'm, you know, I'm kind of removed, but, um, I'm, you know, I'm kind of removed, but it's, it's really, it's a really powerful tool. It's a. It's a good thing to know, but it's also really good to be well-rounded, right, I mean, particularly if there's one of you, or two of you. You know you're you got to be able to put input in all these different areas, but you're.
Speaker 1:I mean, I don't know if that's the most accurate adjective, but I think you are a fire starter. You're the kind of person that wants to get involved in the initial stages of the company Probably that skills too much. Then you're not interested anymore and you sort of want to be a generalist because you like solving puzzles and that sort of like hits close to my case as well, which, like when we created Marsbase, I was a CMO because it was in charge of marketing. I was not even CEO and, like you, I don't like roles. The reason why I adopted the CEO role and I think that's something that I've never explained, but it's because potential clients want to talk to the CEO, not to the CMO. Cmo is kind of like the Ryanair of the C-levels, you know. It's kind of like a super low cost or second level, and so it's more like an outwards looking title. Inwards. The three co-founders are more or less like CEO-ing around the company and the three of us could be the CTO and the CEO and the something else. Right?
Speaker 2:Yeah.
Speaker 1:So I sort of understand that. I see that by being a generalist and this entrepreneurial mindset allows us to create a company, At the same time, while this is very good in the initial stages of a company, eventually you hit a level in which you sort of required to change the mindset and delegate, optimize, outsource, eliminate, hire for specialists. I'm starting to feel like this in March. I think we're a little bit early, but I'm now feeling like we're required specialists in a couple of areas, have you like? Is this description accurate or I'm totally?
Speaker 2:off the mark. No, it's totally accurate. I'll actually tell you an experience.
Speaker 1:I had. Where's the level, where's the limit?
Speaker 2:Well, I'll tell you an experience I had where. So when we started our first company in 2004, there were four founders. One of the founders was bought out along the way, so then there were three of us and the company got to a point where it was getting really big and, frankly, I was getting for lack of a better term bored. Like I love the early your term. Fire starters is great.
Speaker 2:I'm going to steal that from you, but I love some of those kind of like those like early, early problems, and when our, when that first company got to a point where the were ones that just weren't very exciting to me, I, I, I, I felt disinterested, and I am the kind of person that I am. I have a personality flaw where I have to be all in on something. If I'm not all in on something, I you'll lose me. I just it's just how I am. I'm like it's. I have a hard time being really giving in when I'm not giving it all, when I'm not really invested mentally, and so when I started mentally checking out, it became very clear to my co-founders, and so I was the first of the three of us sorry, the second of the four co-founders to exit the company. And so I exited the company in 2009, basically took some time off, actually got married, and when I was thinking about what I was going to do after that, I found myself at this really tough crossroads, because I'd spent all this time becoming this really general operator and I had no real specialty. I wasn't a programmer, I had no kind of like special skills, and I felt like my two choices at that fork in the road was I either start a new company or I get hired to like run another company, like in a very kind of general role, and it was. It felt very awkward, I felt very kind of lost because I was like I don't have any discernible skills Like what do you, how do you apply for a job when you your? Your last job was, you know, kind of building a company, I don't know. It just felt very foreign to me, and so what I ended up doing was I ended up getting an iPhone another amazing window for me where I got an iPhone and I saw all these apps on the iPhone and I was like, oh, that's cool, I can make these. And so I taught myself how to do that. And I was like, oh, that's cool, I can make these. And so I taught myself how to do that. And then I learned enough that I then got another job as an iPhone developer, as an app developer, and that started this whole other phase where I went back into engineering.
Speaker 2:So like I was out of engineering, I went back into engineering and I loved it. I was like as happy as can be. I, you know, really could just dive into the, into programming, and I really loved it. Um, but but um, you're right, you can the entrepreneurial journey. You can find yourself in kind of odd, odd, odd spots. You know, um, and I I don't know. I just feel very fortunate that I've been able to kind of like figure things out and get through different kind of valleys or kind of connect valleys in the career. And so if you look at my resume or you look at my LinkedIn, it's not going to be the most beautifully manicured timeline, right, it's like it's got some spots here and there like they're.
Speaker 1:Anybody that tells?
Speaker 2:you. Otherwise is probably lying because, like the reality is like you're right as an entrepreneur, if you have, you know, it's like I've had a tiny bit of success and a ton of failure and you know and, and, and. So have most people. So it's like anybody that tells you that it's all good and they're killing it and all this other bullshit. It's like most likely a lie.
Speaker 1:But in the corporate industry, you know, gap years or sabbaticals are seen as a perceived as something lazy or perceived as something negative, whereas when I see that in serial entrepreneurs, taking gap years means you've had success because otherwise you would have chained, you would have concatenated companies because you were failing. So I need to start fast because I'm running out of money. If you take, more often than not, gaps of two or three or four years, like in your case, that means you were a little bit well off, so that means you could actually spend or at least afford that time. Or because you didn't include your freelancing gigs, as you mentioned. Right, but at least it gives you the impression that, wow, he really took time to enjoy himself. Think, maybe, experiment, live a little bit of life, travel around get some experiences and then, you know, create something new.
Speaker 2:And I don't know. We've been very fortunate to have that. Yeah, I mean, we're very fortunate to be able to live in this great city. We're, you know, fortunate to be able to spend a lot of time with our kids. We're fortunate that, you know, we don't have to work multiple jobs, which a lot of people do, and so we recognize that it's definitely a special time.
Speaker 1:But it's funny because you said you didn't want to be the CTO and you wanted to kind of like, didn't want to box yourself into just being the CTO and not being able to work in other areas of the company. Yet in one of your most recent job experiences return mates you were the CTO, right? So how did that happen? Like why, in that case?
Speaker 2:Well, again, it's because it's just timing. So what had happened is so we sold the first company Lease360, that got renamed to Velocify. That company sold in 2017, 13 years later, and so everybody did very well. I started doing a lot of kind of family planning, estate planning and talking to a lot of advisors around what to do with money and investments and stuff, and just it's because the way my mind works, I started using all this software that these big banks and were giving me to kind of get visibility into my assets and things, and I was like, man, this software sucks. And so I basically was like I'm just going to create my own. And so I basically spent about a year and a half building a. It's essentially like a family office platform for me and my family and it's like mint on steroids, because at that time there was mint and then there was this other platform called personal capital and then there were all these kind of institutional platforms and I needed something in between, because I've got assets that none of these things could manage, like crypto, and I've got a bunch of these angel investments and I just had, I wanted things done in a certain way. So the product guy in me was like, fuck it, I'll build my own platform. And so what happened is I was like, okay, I haven't programmed forever, I've got to relearn how the kids are doing this now. So I basically said, well, I don't want to learn front end, I'll just do the back end, because the back end was always more natural to me. So I got a front end developer in Ukraine and me and this guy basically built this platform that, by the way, I still use today to manage all of my family's affairs. It's really awesome.
Speaker 2:And so when I was kind of done building that, this opportunity came around where a good friend of mine knew a couple entrepreneurs in LA that were looking for a technical person to join their team, and it just happened that I had been. I just spent a year and a half getting up on like the latest and greatest in development, and so it was like, oh well, charles can help you, because not only does he have all this experience building companies and he can invest in the company, but like he can literally roll up his sleeves and like build the whole thing by himself. So that's what I did. I joined these guys in LA and, despite having a family and and you know a wife and three kids in San Diego. I took the train up to LA, uh, twice a week, would stay on the the founder's couch. I literally, you know, I'm, I'm a, I'm an older guy and I'm, you know, sleeping on this guy's couch and we're building this product day and night. It was super fun.
Speaker 2:It was like this, really cool, like renaissance, and in that role I was, you know, like I was the CTO.
Speaker 2:I built the kind of whole first not the first data version of it before I came, but we rebuilt the whole platform, hired the team, but with those guys they were really great guys. They're just fantastic entrepreneurs and I think that they knew that I had a lot of experience to bring to the table and they never treated me like a CTO. They always treated me like an equal. They always, you know, they gave me tons of equity and they always asked for my opinion on everything from legal to strategy and I was able to help them because I had kind of been through all that. But then, yes, I still did all the engineering and built out that team. But again, it was one of these things where it was like right place, right time, you know, like if you came to me right now and somebody wanted me to be the CTO, I'd be like I can't do it. I don't know. I don't even have VS Code on my laptop anymore.
Speaker 1:But five years ago you know fairly enough, you mentioned like when you started was 20 years ago, there was no Stack Overflow, it was not even close to getting started. But five years ago we had Stack Overflow, we had Google, we had Reddit, we had all of these documentation everywhere. Nowadays you even have, like, if I wanted to become the CTO of something, I would be going to chat GPT, basically just asking questions, cursor, blah, blah, blah. How did you do it five years ago? Because, after so many years of not actually being in the trenches, so much of technology, what was the thought process? What tools did you use? Was it books? Was it courses, was it, I don't know, diy everything? No, courses, was it?
Speaker 2:like I don't know diy everything or no. Actually I I'm trying to think of how I figured it out, but um, the technology changes a lot like five years ago.
Speaker 1:You know containers where, everywhere, but like 20 years ago, that technology didn't exist. How did you bring up to catch up with everything?
Speaker 2:I'm trying, I, I, so I was. I talked with a developer, I was talking with a guy and we were I was trying to think of's called AppSync, and it was basically a way to you know, it's kind of one of you know how AWS has all these integrated products. It was a way where you could really quickly launch a. It's essentially like a GraphQL server that talked to a. At that time you could use, you know, different databases, but I think we used like a Postgres database and it made it just made development super easy. It was like, as you know, like with development, it's all about like layers of abstraction, right, like you've got bare metal, like you've got the bare metal and then you've got like, how many layers of abstraction are you at Right, like um, and so this was a tool that was pretty far removed and and and made it really easy to kind of build, spin up a backend.
Speaker 2:I. I had never used GraphQL before, so I had to learn GraphQL and that was a fun thing, but I also another theme that I will share with you is because I'm somewhat of a. I like to torture myself. I always force myself to like learn something new. So, like, for some godforsaken reason. I decided, oh, I'm going to do this thing in GraphQL. And I had never even heard of GraphQL. But I was like, oh, I love it, it's super cool, it looks super elegant and it was hard as shit to figure out, but once I figured it out it was super cool. And so sometimes when people ask me like, oh, how did you choose to do this? It was like, well, I talked to a guy and he kind of turned me onto this thing and I've always loved AWS and they seem to have nice tools. And I just started playing with it and I was like, okay, cool, this works. And you know, kind of off we went and then, you know, the front end was all you know, react and TypeScript and JavaScript, but I was not on the front end of that side. But yeah, I mean the tools.
Speaker 2:Now ChatGPT, I haven't. I know that you're super deep in the ChatGPT and, by the way, I use ChatGPT and Perplexity pretty much all like a lot every day. I've actually used it a lot more since I met you. You've definitely inspired me to use those tools more and I, the more I use them, the more I them I'm. I'm still kind of like not sure which one I love better chat, gpt or perplexity, um, but um, they're amazing, so good, and so I'm not really sure how guys are using them today. I mean, I know there's things like copilot and, and everybody's got a, a companion or a tool. I'm not sure how people are using it today. I don't know if developers are saying like, hey, write me a, you know, write me some function to do this. That'd be amazing. But, like I, I never had the opportunity to do that and I, I I'm not. You know, I've got kind of mixed feelings on it a little bit well, I mean you should try.
Speaker 1:You should try it. It's interesting. It's not going to solve all the world's problems, but at least it helps you get rid of the blank canvas syndrome. And, for instance, I'm kind of like the super, like a person that finds a lot of trouble in deciding the stack of things or how to organize project folders and stuff like that, because I'm you know, I'm kind of like this, I'm a perfectionist, so it it is helping me to get rid of perfectionism. Just because it's like get shit done right. It's like, oh, I want this. It's like that Boom, no excuses, it's done already. You can debate whether you would reorganize. You know the assets here and these other like organization of folders.
Speaker 2:Right, you're doing PTSD, talking about folder structure?
Speaker 1:Exactly no, but that's the thing like for me, it up until now it would have been an excuse, or, oh, I don't know. React I'm not going to start a project until I master react and I start with. No, it's not, I need a react project for this. Like boom, it gets it done, and like you start building on something, so it activates a certain part of your brain where you are able to kind of like correct, connect and um, and maybe like calibrate if you want, instead of figuring out the stuff. That it's kind of like it's binary, it's done or it's not done, but uh, it doesn't really require a lot of gray matter, right? So, um, the more mechanical tasks you don't need to figure out. Then after that you can perfect it to your brain's content and whatnot, right, and so it. It works precisely like that.
Speaker 1:Hey, now write a controller that does this. Or I want to rewrite the views and react instead of like pure rails application, whatnot. It will do it, but because you and I have got the domain expertise, we're able to see all the implications, because the the problem with this kind of AI is like it really does that, but because it's an AI, it just executes. Like the context is pretty limited and so some of these decisions doesn't like it doesn't take into account long-term vision, whereas you would do it. So it gets the job done for that context, for that specific prompt.
Speaker 1:But maybe this changes too much in the backend or changes other parts of the application that, if you're able to spot it, you're like, yeah, but don't do this, don't do that.
Speaker 1:You should actually scope like a zero in, like a little bit, limit more the scope of the prompt, otherwise it will just touch the entire application and you don't want that Like, oh, write me just a model and do only this, but do not specifically do the blah blah, blah, blah, blah. So the more accurate you are. That's why I've been writing a lot about spaghetti prompting lately, because there's a correlation between spaghetti prompting and spaghetti coding and I think that it actually happens. Same with AI. I see a lot of people who are like, oh, yeah, I got an app in React running in 10 minutes and like, look at this. But yeah, great, that's a zero to one, but the one to five it's going to take forever because you will be iterating 10,000 times. It will not work and then you will ask it to solve this bug, but because it doesn't really understand everything and you don't understand what the AI is doing, you're not able to correct it and therefore you would be just beating around the bush all the time.
Speaker 2:So that's why I'm skeptical but optimist.
Speaker 1:Yeah, before wrapping it up, because we're close to an hour now and I want you to have some kind of space to give advice to aspiring entrepreneurs who might be looking for somebody like you, like you specifically speaking about like technical enough to run as a CTO, but who can decide whether to be the CTO, the operations guy or these fire starters who get shit done. Basically, where do you find people like you?
Speaker 2:Yeah, I mean, I think it was the question where do they find people like me?
Speaker 1:Yeah, and more importantly, how do they keep you around in these companies?
Speaker 2:What I'm most interested in doing right now is until I have some inspiration to able to bring to kind before they even have anything right, I think. I think one of the interesting things that I found here in Barcelona is my sense is that the investors are a little bit more conservative here. They want to see some things. They want to see kind of more progress where, like I, want to back people based on them as a person and not what I think that they're building. Because a lot of times, like I got this question recently from Notch Merner they said do you invest based on product or do you invest on person? And my answer is person all day, because the product is going to change and the best entrepreneurs that I've backed have always had changes in their products. It's just the nature of it. It's an organic thing. If you invested based on a product and then the product changes, you might get kind of disappointed, whereas I want to invest in people who have a thesis and have a, an idea of how they want to solve a problem, but, by the way, like that, the way you solve that or way you approach that thesis might change. And so you know what I'm looking for in this ecosystem and the conversations that I love to have are just with people who are trying to build stuff and who are inspired to build things, and I don't only do technology investments One of my best investments is a beauty company in Los Angeles but I want to meet and be inspired by other builders and I want to be basically the first check. I want to invest before anybody else invests, because it's at that point that I can help the most. It's at that point that I can help with all the things, from helping them legally or helping them do advice on hiring and advice, obviously, on technology. But you know, the bigger a company gets, the less they need, they need me and also the less I get. I'm interested, right. So, like you know, one of the things that I'm trying to do is is is just talk to as many interesting people as I can who are building cool things and and my advice is always free building cool things and and my advice is always free and if I'm, if I, if I'm excited enough, I'm going to want to, I'm going to want to, I'm going to want to, you know, back it up with with some money, and I'm at a really fortunate place right now where, you know, I can support other entrepreneurs, which I think is super cool, and and and I I kind of consider it like planting seeds, like I want to plant seeds and I want to water them, and that's what I'm really good at, um, and I'm really good at.
Speaker 2:I think I'm really good at um betting on people Like I. I I have an intuition about people and I feel like I'm I I have a pretty good track record of of, of betting on the right people, um, and so that's, you know, it goes full circle to why I reached out to you originally because, like you know, when I met you, you're an amazing person. You're, you know, you're very modest person, but you know, you're one of the most well-connected people in this town and so, like there's so many great people here and I just want to hear what people are up to and if somebody needs support, before some they need a check and before other people write a check, like I want to talk to them because I probably will take more risks than others will, and part of that is because there's a little something off with me.
Speaker 1:There's quite a lot of things to unwrap here, but basically, thank you for the kind words. The respect is mutual. That's one Second. The interest the thing that you mentioned about keeping you interested is very important because I think one of the most common mistakes entrepreneurs do when hiring or when trying to fish for technical profiles is like oh, they want somebody to produce code or hire engineers.
Speaker 1:And it's like well, that is not interesting. Most technical people, they're not driven by money or aspirations or fame or whatever. They just want to solve real problems. And if the problems are not interesting, they will not join your company. So, and if the company they might have a short-term problem, it's okay, but then you will not keep these people for very long because, like, the interest dissipates over the years. So, yeah, you raise a really interesting point.
Speaker 1:And the other thing that I think is really interesting from your profile as well and that's something that I also share in my sort of pitch when I'm pitching entrepreneurs where I want to invest, in whom I want to invest, is I'm a technical person. Right, and precisely, there are not so many CTOs or technical people investing that can audit your technology, that can vouch for your architect, or that can help you hire a CTO investing that can audit your technology, that can vouch for your architect or that can help you hire a CTO that can help you audit or inspect your API or sort of like figure out integrations and stuff like that. So I think that's actually a very good value proposition for an angel investor. That sort of distinguishes us from other profiles. Before we wrap it up and we're way over time, but this is getting very interesting and this is a signature question of the podcast is what has been your most expensive technical fuck up so far has to be yours.
Speaker 1:We have to own up to it most expensive, yeah one big fuck up that he like, oh jeez, it kind of like wiped out production database or I mean, don't worry, no pressure, somebody set their office on fire and so you're not going to top that one Pressure's off.
Speaker 2:Hmm, I gotta think about this one. I mean, most of my fuck-ups are not technical. Most of my fuck-ups are human fuck-ups.
Speaker 1:Okay.
Speaker 2:Let's go for that one, and the most kind of issues I've had in my career, the most kind of challenges I've had in my career, are not technical ones, they're people ones and they're mostly focused around just having high EQ or, in my case early on in my career, having very low EQ. And so when I was building my first company, I really was not concerned with the human side of things. I was trying to build a great product and I was trying to build a really successful company, and I didn't really give a shit about how people felt, or I didn't really care about how people thought about me, and I think that created a lot of issues for me, because, you know, building companies is a a human endeavor, right? Like? I don't care how technical the product is or the software is or whether it's quantum computing. Humans are building these things. These humans need their act, and it took me a long time to figure this out and I'm still figuring it out how to be a more emotionally intelligent person, how to really understand the lens of the people that are working with you and working for you.
Speaker 2:That changed everything for me. So, like, I've never burned an office down, I've never deleted a production database. But I have, you know, really killed some relationships. I've, I've, I've turned a lot of people off. I've been a complete asshole. Um, you know, uh and uh it's something that I've worked on for the last 15 years is really trying to be a, uh, more emotionally intelligent person, a more understanding person and um, and yeah, I'd, I'd say that's, that's my, those are my big fuck ups and and and that's the stuff that I kind of try and work on.
Speaker 1:Thanks for sharing, thanks for opening up. You've been extremely generous with your time and with your advice. Any parting words? I'm rolling out the carpet for you, so 30 seconds. How can we help you back?
Speaker 2:Yeah, I mean. I just say, if anybody listens to this pod and is trying to build some stuff, whether you're in Barcelona or not, I'd love to talk to you. I'd love to share with you anything I can and, like I said, I'll share with anybody for free. I'll tell you my unfiltered thoughts and if you're doing something really exciting, I'd love to invest.
Speaker 1:And we will see you building something. If you don't find anybody else doing something interesting, We'll see Charles if you don't find anybody else doing something interesting.
Speaker 2:We'll see.
Speaker 1:Charles, thank you very much.
Speaker 2:Thanks, alex, great to see you Awesome.