Inside CTOx with George Reyna (Final).m4a Thu, Nov 13, 2025 0:00 - George Reyna Like I knew there was a way to help people. A buddy of mine actually had said, Hey, check out this link. You know, it sounds like it's right up your alley. And so, you know, I was reading up the, uh, you know, the, the front page and I was like, holy cow, like this is, this is screaming my name. Like I need to, I need to check it out. 0:18 - Donna Welcome to Inside CTOx Podcast. I'm Donna, head of membership and partnership. And today we're stepping Inside the minds of some of the most innovative tech leaders out there. This isn't just a podcast. It's a place where CTOx journeys come alive. Where stories of struggles, breakthroughs, and growths unfold. We're here to unpack the experiences of real CTOs navigating through our CTOx Accelerator and Membership Program. So sit back, tune in, let's get into the story. Welcome to another episode of the Inside CTOx Podcast. Today, I'd like to introduce you to George. Powerhouse of transformation in tech. From leading enterprise level digital overhauls in the real estate sector, to helping companies unlock real value through strategic innovation. George has a knack for making big, complex shifts feel seamless. But what makes him truly stand out within the CTOx tribe, since joining CTOx, George has been orchestrating something quite special. Something that most tech leaders could only dream of He is relocating his entire family to Spain, all while keeping a fully operational, globally connected business thriving. Proof that freedom and high performance can go hand in hand. Welcome, George. 1:45 - George Reyna Thank you so much. Glad to be here. 1:47 - Donna So Spain, wow. That's a big move. 1:51 - George Reyna Yeah, yeah, definitely. 1:54 - Donna Are you excited? 1:55 - George Reyna I'm super excited. We still live in Europe when I was growing up way back in the day and so I've got a taste for, you know, what that life is like, It's totally different and I'm just looking forward to just having the family immerse in the culture there and just, you know, kick back on the beach and enjoy life out there. 2:16 - Donna That's fantastic. You're going to have a lot of jealous listeners. Cheers D-Boy. Idea of it. Fantastic. So, so thank you for sharing your journey. Thinking back to, to before joining CTOx, what was happening in your career or your life at that time that just made joining CTOx feel like the right move? 2:38 - George Reyna Yes, good, thoughtful question. So before I joined the program, I was actually just trying, like I knew what I wanted to do and I knew what it kind of looked like in, you know, the grand scheme of things. I didn't know that there was like an actual name for, you know, what I wanted to do. And so, you know, before joining the program, really, I was just trying to figure out how to, you know, put the jigsaw piece, you know, together. And so, you know, just coming straight off of leaving corporate, I had, since 2012, been working for a major organization handling product management and strategy on that side. And so, you know, I knew that there was a lot of empirical wisdom that, you know, that I could leverage and, you know, in my, you know, expertise in real estate and how much of an opportunity there was, like, I knew there was a way to help people. And so, you know, I would grab this strategy, I would grab this framework and try to, you know, create like this smorgasbord and, you know, for some folks, it made sense, but like, there needed to be structure. And a buddy of mine actually had said, hey, check out this link, you know, sounds like it's right up your alley. And so, you know, I was reading up the, you know, the front page, and I was like, holy cow, like, this is screaming my name, like, I need to check it out. You know, set up a session with the team there and got onboarded I think it was the next day. 4:14 - Donna Oh, so you're a quick start. Oh, good. We like that. So talk to me about real estate. Where did that come from Is that a family thing? Is that local to you? How did you get into real estate? 4:28 - George Reyna Good question. So I have always been business minded, right? I've tried, you know, ever since I was a teenager, try to, you know, come up with new ideas, new ways to make money and, you know, just try to, you know, make a good and cool business. And, you know, real estate was, you know, always the at the top of the list for, you know, passive income and income generating. And, you know, it was just a it was it was a keystone for really how to build wealth in a lot of the area that I was interested in. And so, you know, at first I was looking at real estate from the lens of like an acquisitions piece, like I would actually buy the real estate, I would be making the deals. And although I can, my expertise aligned more on the tech side. And so because a lot of the people in real estate, a large part of my network, wanted to do the talking, wanted to do the relationship building and whatnot, but didn't have any framework behind it. I was like, heck, yeah, like, I've got an answer for you. This is what you do. And these are the dots that you connect. And so it just kind of naturally grew into this, you know, wild, wild ride that we bring here today. 5:44 - Donna That's fantastic. So, you know, when we think about real estate, that's not a tech, it doesn't seem like at least it's a tech focused industry. So, you know, for the listeners thinking, Oh my God, what are you even going to do in technology for real estate? Give us a little bit of an overview of the type of tech you work. 6:04 - George Reyna Yeah, yeah, definitely. So you hit a really good nail on the head because there are very specific industries, real estate included, who are just incredibly slow to adopt technology. And a lot of a lot of the success from real estate comes from just honestly from the older folks who just have tougher skin and was able to, you know, weather the storms or they have capital to, you know, to be able to have that kind of cushion. And so when you've got these older folks or these, you know, startups or entrepreneurs who are just used to just like, you know, pounding out elbow grease to get a deal done, nobody's, you know, everybody's got a spreadsheet, a Google spreadsheet or, you know, back of the napkin that they're using. And so, you know, being able to come in and say, hey, this is how you should structure your CRM. These are the automations that you should be and it's your pipeline. The ideal end state for this whole thing is like, I want for you to have an easy button, like a big red easy button. You just push the button and just watch stuff happen, watch the magic and automations and all that fun bot stuff, you know, kind of just take place and really just, you know, automate as much as we can for the business. And that's really where I come in is, you know, helping out business owners automate their processes, their pipeline so that it's more effective, more purpose-driven, implementing AI where we can and just helping folks who are kind of later in the game to stay up front and make sure I'm tagging them along in this crazy, crazy space of ours. 7:49 - Donna Later in the game, that's a great phrase. So talk to us a little bit about, you're one of the younger members in C2OX, I hope you don't mind me saying. So how do you, as this young, cool guy, face up against these guys who are later in the game? What approach do you take? 8:11 - George Reyna Luckily, I've got a pretty solid network. And so the word of mouth has spread pretty quickly about my skill set. And so luckily, I don't have too much of an issue when it comes to saying, hey, here's what I can do, because everybody knows, at least in my network, what I can do. There are a lot of new faces that come across my desk. And I have my hat backwards. I've got tattoos. And I wear T-shirts and running shorts sometimes. And that's who I am. And it doesn't matter how I dress or what I look like, if I can change the game and move the needle in some unbelievable ways and just create magic for your organization. I mean, at the end of the day, that's all that counts, right? It doesn't matter how young I might look. Mind you, I am trying to grow a little bit of something. 9:10 - Donna You think that's gonna make you look more older, more distinguished? 9:15 - George Reyna I tried growing it out, but it looks ridiculous. 9:17 - Donna It looks good so far. You've done so far so it looks good. So, you know, we talk a lot in the C2X about, like, leadership. So, you know, it's just not always being about the smartest guy in the room. So what has been some of the leadership tactics that you've used? 9:42 - George Reyna A lot of the leadership tactics that I use are really just I mean, kind of aligned to what you said, right? Just like acknowledging the fact that you don't know everything, and just trusting in my own abilities and my own skill set, and knowing and being confident in what I know, which is a lot. But coming from corporate, there were so many different personalities, so many different people that I had to get along with, shake hands with, and kind of put a fake smile on. I've, you know, I've gone through, you know, different situations and even challenging times trying to get through from, you know, on the people side. But it's really mold me to be able to service a wide, very wide spectrum of different folks, right? And so when you come to these leaders, you know, whether it's a fast talker, you know, you know, black and white kind of guy, or if it's a slow talker who just likes to kind of, you know, spend the next 20 and it's talking about grandma's potato salad. Like, there's a way for you to just, you know, make sure that, like, as a leader, here's what we're going to do together. Because it's not just, like, the way that I look at leadership is less about me being the expert, right? Like, I, not to toot my horn, but, like, I know a lot of stuff, right? But I don't ever want to be framed as the expert. Because a lot of times what ends up happening, is when a business owner sees an expert come on board, what tends to happen is they're like, okay, so you know everything, and you probably should help run the business, right? Like, what should I do now? Does this, like, should we do this? Like, and it's a collaboration thing, right? That leadership is ensuring that the integrity of what we're, you know, coming in and shaking hands together on is a collaborative effort. And so being able to just, you know, come together, say, you know, we have different, unique ways of contributing effort. Here's how I'm going to do it. Here's what I expect out of you. And, you know, we just have that conversation and it's, it's, it's really, really been beneficial, you know, with that approach. 12:00 - Donna Yeah. Oh, that's good. That's good. And you seem to be like, just staying very true to you and, and, and humble, if you don't mind me saying. How important is, is that that kind of staying who you are in this kind of crazy world that we're in right now? 12:17 - George Reyna Yeah. So for me, with my analytical brain, I have to stay true to who I am. Because when I put on that face, or when I put on the extra smile that doesn't, when it doesn't feel right, I feel like it's a lie. I feel like I'm lying to myself. When I get into an engagement with these business owners, I don't like to portray myself in any way, just being naturally who I am, standing on my own values and my own moral beliefs and my own ethics. And just standing in that space, knowing who I am, I think that in itself inherently allows for some of that confidence to come out. And, you know, it's, it's, it's relatable. It's, it's, it's very, it's very people, person to me, because that's how I connect. When I, when I pretend to know something, or if I pretend to do anything in any way, like, I need to have, I need to be able to fill in space, like, even like, so when I first started off, like, you onboarding calls and discovery calls and whatnot, I had to have a script. And understanding that, like, a lot of these folks don't, like, they can tell you're reading the script, right? And so being able to, like, naturally engage and be able to answer questions honestly and, you know, without getting caught off guard and they ask a question I wasn't really prepared for, like, that's the kind of stuff that was like, oh, man, like, what am I doing? I have to reevaluate, like, who I am, what kind of service I'm providing, what I'm offering out there. And so just making a decision, figuring out what it is I want to do, who I want to serve, who I want to be, who do I want to become, who do I need to bring in to help me grow, what do I need to forego to have those things happen for me. They're all decisions that I have to make internally for myself, and that stuff really does speak volumes. 14:28 - Donna Oh, that's so nice. Thank you for sharing that. So let me ask you this, as a technologist, a leader and a father about to move to a whole new world, what does freedom look like to you now as compared to maybe 10 years ago? 14:47 - George Reyna It's a good question. 10 ago, let's see, ago, 10 I was a guy who just wanted to do well. And I didn't really even have that part figured out. I knew that, like, there's a lot of George in here and George has a lot to offer. And so I didn't know, like, how that part would evolve or what would unfold before me. And so what's crazy is everything that I've done, like everything that I've wanted ever since I was little, I've always imagined me just like, you know, if I had if I wanted a Mustang, I would imagine, you know, the Mustang parked out in front of the house. If I if I wanted a house, I'd imagine the literally the house that I live in now. I actually the previous owners probably thought it was a little creepy, but I knew that this house was for sale in the neighborhood that I've always wanted as a kid. The house was for sale. I parked in the driveway and I imagine like, oh, this is me coming home. I didn't live there. I live somewhere entirely different. But long story short, bought the house. And so for me, back 10 I knew that when I was going to be in my 30s, I was going to be successful. I was going to have my own business. I was going to have my own money. I was going to have my own freedom. And so call it manifestation, call it whatever you want. But it's It's all about just, you know, making the choice and, you know, really just acknowledging the fact that, like, the things that you talk about with yourself really do matter, right? And so I guess in another way to say, like, my manifestation now is being out there in Europe, being out there in Spain, And I imagine me and my daughter riding a bike on the beach and, you know, just enjoying walking the cobblestone streets with my wife and just having, you know, tapas and wine and going to the wine country, going to Paris and going to Italy for my birthday. Like, these are all things that I've made up in my mind, have an actual scene in my movie, and it's all a matter of time. And so that's what I'm looking forward to. I'm just creating those stories for her. Myself and for my family today. 17:20 - Donna Wow. That's, that's amazing. Wow. Oh, I'm really, yeah, I can, I can, I can see that as you're, as you're talking about it, I can visualize that. I'm sure it's so much more clear than you. Um, and that's, that's a wonderful, like what a journey to go on from kind of where you were, um, to kind of where you are now and, and, and what you can, what you can do with that. You know, in CTOx, we see a lot of this like transformation. Shift, you know, they come in almost like one person and then, you know, six months later, they're just, they feel like a completely different person. What part of the process within that CTOx Accelerator did you really take the most from in terms of that transformation? 18:02 - George Reyna I think for me, it was, and it might sound cliche, but it was very, it was very a whole division trust the process. A lot of, a lot of the things that were, because like you join T2X and they literally tell you exactly what you need to do. And so for me, it was like, I don't, I would, I would find ways to call it self-sabotage. I don't know what you want to call it, but like, I don't know if I want to go with this vendor. I don't know if I should do this. Should I work on this part? And so just being able to say like, okay, let me just go through this and see, you know, how this evolves and how I can make it mine over time, for me has been the biggest thing is because, you know, when I have someone to help guide me, you know, whether it's the community, whether it's the Slack, whether it's Leo or Marisa or you, whoever, you know, whatever wizard comes on in our, it's been incredibly helpful. And just trusting you guys, honestly, it's like, there was a book that I Read, I forgot which one it was, but essentially, all it was saying was like, when it comes to real estate, for example, you could figure it out on your own. But if you know someone who's got a strategy that works, just try it out. 19:30 - Donna And so that's kind of the way I've adopted how I, you know, stepped forward into this thing is just like, there's a strategy here let me just trust the experts here see what happens and yeah I had no problem making it mine but yeah it was just kind of following the steps I think that's it I think you've just nailed it there is like you know follow the steps and then make it your own it's like everybody's on a different journey so everybody's interpreting this in a slightly different way and I think that's what's so exciting when you see the the community you have such wide range of people just from every possible background. Even though they're one thing in common, they're all CTOs, but just from such a different array of experiences and they can all use the same proven processes, but making it their own. And I think that's a real exciting thing. So last question before the last question. If you could pass down one lesson to the next generation, of CTOs coming up fast behind you, what would your one piece of advice be? 20:38 - George Reyna If I could choose one, it would really be about just, I think most important is how you show up. And, and that means so many different things for me. It's like how you show up to your calls, how you show up to the client, how you show up for your family, how you show up for for yourself, it's important because there are so many things that we hold so much importance to that just don't matter. They don't even matter. And so just being able to acknowledge the fact that you've got people that look up to you, how you show up is incredibly important because it means everything. And to be able to show up as your best self. And I think that there's a lot that comes from being able to do that. You give yourself grace. You give yourself permission to be who you are. You give yourself the ability to manage your day to day a lot better. When you know who you are, you can show up authentically in a way that's just relatable It's connectable. It's just, it feels good. It feels good Inside. And it's extremely purpose-driven. 22:04 - Donna Well, thank you. That's great advice. And you clearly live that advice. I can, you know, I speak from experience on that. Okay. Our last question. You don't know, you don't know anything about this, but we've done this on the other podcast and it's been so much fun. So I'm gonna ask ChachiBT right here, live, a question, a thought-provoking question, and you have to answer it regardless of what it is. Are you ready for the challenge? 22:38 - George Reyna Let's go. 22:40 - Donna Okay, so let me just bring up ChachiBT. Here we go. Okay. Hello, ChachiBT. We love a bit of spontaneity, so we Who better to challenge us than AI? What question would you like to ask a fractional CTOx at this exact moment in time? Okay. It's thinking. Okay. Okay. 23:12 - Donna This is an interesting one for you. 23:14 - Donna If your next client project. Had zero budget but infinite trust, what would you build and what would it reveal about how you truly want to lead? 23:32 - George Reyna That is a great question. 23:33 - Donna That might be the best question we've had yet. I'll be honest. And I know you've had experience with zero budget. Yes, I have. 23:46 - George Reyna I think the two biggest things that stick out to me are alignment and boundaries. I think that when you form a really great relationship with an individual and just everything they do just is super aligned to everything that you stand for, it's easy to say, let me help you out. And especially for those who are just starting out, who don't know how to like, you know, snag a, you know, a multi-figure retainer, you know, sometimes we kind of don't have a choice to, you know, kind of prove ourself before, you know, that door, that gate is completely open. So, you know, when it comes to doing free work, For me, it's like, let me, I'm going to still give everything. And literally just two days ago, I had a really, really great friend and, or have a really great friend, not had. And he's telling me about this really, really amazing business idea. And I'm like, heck yeah, that sounds so cool. And so he's like, you know, tell me what it would take to bring you on board. I'm kind of cash strapped right now. I was like, okay, well, I totally understand. I'll tell you what, let me just organize some notes. Let me come up with a 30, 60, 90 day plan, put a real solid action plan together. Let's put it in front of us, see what that looks like, And then you tell me if we should have a conversation about doing business together. And so I had spent a couple hours everything together, and gladly, because for me, it's like, I don't want to do something halfway, right? And so just being able to stamp my name on it, I gave it my full effort. And later on that evening, packaged it all together for him and said, what do you think? And he's like, oh, it looks solid. OK, cool. Here's what a retainer looks like, And so, and ultimately he decided, he was like, you know what, here's what I'm gonna do instead. 26:13 - George Reyna And so I'm like, you know, it's perfectly okay. 26:15 - George Reyna Like I am totally, you know, fine with that. 26:18 - George Reyna Like you put it out there in the universe, you better make it happen. 26:23 - George Reyna And you know, it's, if I didn't have any other thing and anything else to do, I'd love to like, okay, let's spin something up together. 26:33 - George Reyna But, you know, there's a lot on my plate right now and I gotta make sure that I'm stewarding, you know, my family's trust, my time, and, you know, just being able to make the right kind of choices. 26:46 - George Reyna And a lot of times with boundaries, it's like, when you establish the boundaries for yourself, like you're gonna have to say no to a lot of stuff you probably might've kind of bent little backwards for before. 27:01 - George Reyna But by establishing those boundaries, when they're confronted, nobody really likes it. 27:09 - George Reyna It's always like this kind of, it's kind of like a weird kind of like nasty feeling. 27:14 - George Reyna But like, you're able to walk away with, I mean, your dignity, you're able to walk away with your professionalism, you're able to walk away with just, again, going back to who you are, being able to stay And honestly, just exercising those boundaries, saying no to the smaller projects or saying no to the free work, you do that enough times, you're going to have 20 clients at $200 a pop. 27:42 - George Reyna And you're going to go crazy. 27:43 - George Reyna I've been there. 27:45 - George Reyna And so saying no to those kinds of things and allowing the space for my capacity to be allotted to what I'm here to do has allowed me to take on the clients that I want to work with, who are able to pay the kind of tickets that I'm charging for and whatnot. 28:03 - George Reyna So yeah, that's the... 28:07 - Donna That's it. 28:08 - Donna Stay true. 28:09 - Donna Stay true. 28:10 - Donnar I think that's been the one thing I've seen from you over and over again. 28:14 - Donna It's like, stay true to who you are, stay true to the, regardless of what the project is, regardless of what the client or the budget or what have you. 28:23 - Donna staying true is what's going to keep you right. 28:26 - George Reyna Exactly. 28:28 - Donna Great. 28:29 - Donna Well, George, thank you so much. 28:31 - Donna This has been so much fun. 28:32 - Donna I really, really appreciate it. 28:34 - Donna Thank you for sharing your journey, your insight, your wisdom, so much wisdom at such a young age. 28:39 - Donna We're blessed to have you. 28:40 - Donna So thank you very much. 28:42 - Donna And we'll see you again soon. 28:44 - George Reyna Absolutely. 28:44 - Donna See you. 28:45 - Donna Stories, experiences and advice you hear today are incredibly valuable, not just for CTOs, but for the broader tech community and leaders. 28:54 - Donna To our listeners, thanks for tuning in to Inside CTOx. 28:57 - Donna Don't forget to follow us on social media, tag us, and share your favorite insights from the episode. 29:03 - Donna We love hearing your feedback. 29:04 - Donna Make sure to subscribe and check in again for our next episode, where we'll continue to explore the stories behind the tech leaders shaping the future. 29:12 - Donna Until next time.