Inside CTOx with Glenn Antoine (Final).m4a Mon, Feb 23, 2026 0:00 - Glenn Antoine He's like, your passion is flying. He's like, you'd fly every day if you could. He said, you love volunteering for all types of different aviation things. He's like, you've got 20 years background in aviation. Why is that not your niche? And I went, I don't have a good answer for that. 0:16 - Donna Welcome to Inside CTOx Podcast. 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 CTO 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 Inside CTOx, where we decode the new playbook for tech leadership, freedom, and scale. Today's guest is Glenn Antonie, a fractional CTO, CISO, and trusted M&A tech advisor who's flown more than planes. With a background in both naval and general aviation, Glenn brings cockpit level precision to software, cyber and due diligence. He's helped over 200 founders and investors de-risk critical tech bets before exits, acquisitions, and inflection points. But Glenn doesn't just do tech. He sees it like an aircraft system. Every part matters, and failure simply just not an option. Since joining CTOx, his ambition has really taken off, and he's here to share his story and insights. Welcome. 1:53 - Glenn Antoine Thanks, Donna. Happy to be here. 1:56 - Donna Glad you could make it. So now you joined CTOx way, way, way back at the end of last year, towards the end of last year. Tell us about the exact moment that made you decide this thing is for me. Was it a pain point? Was it a vision? Was it a dream? What was it? 2:19 - Glenn Antoine It was colleagues. Some very close friends, colleagues that I've known for years. I was at a transition period and like many of us, I'd like to think I'm not the only one. I had been, I was way lax in getting caught up with them and so I was blessed to be able to meet them in person, have coffee and just get caught up. And then I started talking about our career professional side. And I was talking about different ideas I had, things that I was looking to do. And at that point in time, the job market wasn't particularly strong. And while all of them are local to my area, they don't know each other and didn't know that I was to any of them and five different people over a two-week period asked me, said, why would you look for another job? They're like, you need to be a CTO, CISO. And by the way, can you help my clients? And that was an aha moment for me because it was something I just took for granted that I was doing without really thinking about it or understanding how Not really, probably not assigning the correct value to what I was providing. And that was an aha moment for me. And then fortunately, a friend, another friend and colleague reached out to me a couple of days after that. He's like, hey, have you seen these guys? And he sends me a link to CDOX. And he had actually spoken and he had told them about me, and so I'm reading the link, and I get a text. 4:18 - Donna Sounds about right. 4:20 - Glenn Antoine And that was a turning point for me. Yeah, and then you joined, and a year later here we are. And here I am. It's been one aha moment after another because I have a love-hate relationship with being really focused on a project because oftentimes you don't lift your head up above the weeds to look around and see what the rest of the world is doing. This has allowed me to do that in a grand fashion. All the team around and all the different members and the support that you provide. It's been, you know, that concept or that pitfall of working in a vacuum by yourself. It goes away. I mean, when you're surrounded by this many people, if you don't get something out of it, it's because you went and and laid down and went to sleep and forgot to wake up. I mean, it's been fantastic. And just being able to collaborate and network and talk to other people and things they discover and they share with the group, it's like, oh, that's great. I may never have stumbled across that because I would have had to have had the exact circumstance the right trigger to try something that they were doing, yet I can get value out of it. 6:06 - Donna Yeah, we definitely encourage like, you know, members learning from each other. You know, I think that goes a long way to just feeling supportive and feeling like I can help other people within the community. But we do love to push people outside their comfort zone. So just a little, just a little. So like, you know, what was your comfort zone moment where you're like, oh my God, and tell us what you did to push outside of that. Niche. 6:40 - Glenn Antoine Just sum it up with one word. Yeah. And here's the thing. My wife has a background in medical, was in the medical field for a long time and worked with a number of doctors had highly specialized niches, incredibly successful, highly sought out, on and on. So they're not your general, you're not going to go see them if you need a, you've got a cold or you sprained your ankles, but they had these really tight niches. And so I know it works. 7:17 - Donna Yeah. 7:19 - Glenn Antoine But implementing one was, I'm like, and it's the whole fear of loss. 7:27 - Donna Yeah. 7:27 - Glenn Antoine It's thinking about what am I giving up? Instead of what about what am I gaining? And it was great. I was talking to Marissa and Lior. And Lior asked me, I was telling him about all the work I was doing in the M&A space. And that was probably going to be my niche. And he's like, why? And so I justified and explained and went, he goes, Okay, that's really good. What else? And so I further spent time justifying it. And he's like, okay. He's like, I agree with all that. But he's like, what's it really? And at that point I stopped and I'm like, okay, Lior, I'm walking into a trap and I can't see it. 8:17 - Donna He gets the hard hitting questions. Lior, he knows what to ask. He knows when to push. 8:23 - Glenn Antoine He made a few simple statements. He's like, your passion is flying. He's like, you'd fly every day if you could. He said, love volunteering for all types of different aviation things. He's like, you've got 20 years background in aviation and you've got all this experience that applies directly to them and you're bringing this other real world experience to the table. And he's like, why is that not your niche? And I went, I don't have a good answer for that. It's so, so simple, but I couldn't see the forest for the trees. 9:10 - Donna Yeah. And this is why you sometimes you just need that other person to ask the right questions. And then you have the answer. Like your answer is yes, this is absolutely the right niche, but you need somebody to ask the question. 9:25 - Glenn Antoine Absolutely. And from an aviation perspective, such a tight knit community, I never meet a stranger. I can be flying across the country somewhere, land at some small remote airport and immediately have a connection with someone I'm talking to that I met 30 seconds before the conversation. I mean, it's a neat community and such nice people. And I've said all along that when I'm working in that vertical, I never work a day in my life because it's all aviation. And so it's hard to get better than that. And, you know, if If I'm going to be adding value to a leadership team or founder or business owner, to me, that's a great way to spend my time. And oh, by the way, as an added bonus, if they're on or near an airport, I can fly to go visit them. So I can combine, get a flight in that day and get some work done while I'm at it. 10:46 - Donna Yeah, combining business and pleasure and what a way to commute. Fantastic. So what was, aside from niche, what was the thing that shocked you most, either like personally or professionally through the program? 11:01 - Glenn Antoine I can tell you right now, the thing that I undervalued and didn't fully understand the impact would be the group of people. I expect to learn a lot from people such as yourself, and Leora, and Marissa, and the list goes on. And some of the guest speakers that you guys pull in that provide a ton of value. But just the collaboration and talking with other members, intuitively, I knew that would be there. It, it was really surprising that I didn't fully understand the impact that would have. That's been huge. 11:48 - Donna Yeah. 11:50 - Glenn Antoine It just, it's, um, that and, um, you know, little things that, like you said, just having someone else ask that right question, the number of times that I've been at a perceived sticking point, if if you will, or I think I've got some kind of blocker and someone such as yourself, just a simple question or what if you did this? And then I'm like, yeah, I could have thought about that. 12:23 - Donna Well, as I always say, look, you can't see the label when you're Inside the jar, right? It takes somebody external, whether that's the coaches or whether that's the other members in the community, but like they can look at your situation and be like, well, obviously, why not this? In the same way that when you go into a company, you're looking at their problems from a whole different perspective, a whole fresh set of eyes, and you look at it and probably go, yeah, why don't you just do this? This is so simple. So they're experiencing the same thing that you are. But we hear this over and over again with the community is so strong here with CTOx. Is there someone in particular that from in the community that you've built a special kind of friendship with? 13:09 - Glenn Antoine To pick one person would be tough because I enjoy talking to so many. And here's the piece that really bugs me. I've been so busy the past three months. I haven't had as much opportunity to connect with some of the newer members. And that's driving me crazy because it It's one of those things, I've been blessed to be, have these opportunities show up and bring this new work to the table. 13:42 - Donna Yeah, you've been busy. 13:45 - Glenn Antoine It takes time and it takes brain cycles. And with some of these projects, especially in the M&A space, or if a founder is working to, as you mentioned, It can be some kind of inflection point that's coming up, or there's something urgent that's driving the engagement. I have to make sure that they've got my full and undivided attention. 14:14 - Glenn Antoine Of course. 14:16 - Glenn Antoine And so that has made it challenging. But I mean, yeah, and there's some members have come and gone, and I'm still talking with them. It was a couple months ago, I had, two months ago, I had a former member reach out and say, hey, can I run some questions by you? And it was humbling that they thought of me, everyone they had met, and it was great just to get caught up and find out what they're doing. And so it's, you know. 15:01 - Donna Yeah. Members, members for life. 15:05 - Glenn Antoine Absolutely. I mean, the connections again, the connections are, you know, priceless, but that would be old MasterCard. 15:18 - Donna MasterCard. Yeah. Yeah. For everything else is MasterCard. Excellent marketing. Excellent marketing. Getting there. But yeah, like with the you know, the community like the it's so strong. It's so positive. Everybody really wants to to support each other, which is and give each other advice and be able to show what I love to hear is when members are sharing stories, both of their sort of life before and after, or during CTO X, you know, that's, it's really great. So you've had not just members, but you've helped over 200 hundred companies in pretty high stake moments. So like, tell me how that has changed sort of like before CTOx and like now, after all the things you've learned from Lior, from the other members, like how do you navigate those companies now versus before CTOx? 16:13 - Glenn Antoine So it's a combination of both because with each and every one, I tell people on a regular I could look at 10 different companies, all hosted in, pick one of the major cloud providers, Azure, AWS, they could be using the same tech stack, they could even be in the same or adjacent verticals, and no two of them are the same. Because there's so many different dynamics on how they're operating, the vision the founder has, And when we're on, so you talk about some of the discussions we have within the CTOx group in terms of the workshops. I mean, to me, that was an aha moment. Just sitting down with a team for a half day and having a workshop and going through and having that discussion. As that sounds, that's in essence exactly what I do on the M&A side if I'm in a discovery session for a technical diligence. We have two, three, four hour sessions and it's sometimes they can, you know, and I've been on that side of the table, sometimes it can feel like you're taking a test or you're being grilled, but done properly, it should be very conversational. And in all reality, you know, if I take a look at it, it's really like having a mini workshop to understand where they are currently, why certain decisions were made, because just because they have X in place, it may not be, quote unquote, a typical best practice. However, if there was some strategic decision behind that, and it wasn't just a willy-nilly kind of, well, let's just, or it wasn't forgotten, like some kind of legacy wasn't forgotten. Which I see legacy code all the time. And so that the whole concept of sitting down with a team or a foundation or leadership team and having a workshop to help put a roadmap together for the next period of time, whatever that may be, depending on their objectives, is not unlike what I wind up doing on the M&A side, because often coming out of that, we have findings and we'll have a 100-day plan. What do you need to get done? Sometimes it's pre-acquisition. What do you need to get done before you close? What do you need to be doing in the first hundred days, in the first six months, in the first 12 months? And it's just, it's about prioritizing and having constant discussions within the CETX group about, and actually listening to people like Lior and others that have helped founders from small to massive and over a long period of time. Period of time, it's allowed me to pick up ideas or a different way of looking at it again. Because I've been looking at it one way doesn't mean it's necessarily the right, or it can be better. And so hearing that is huge. 19:59 - Donna Yeah, just having that kind of other person to like bounce ideas off, that be Lior or as you said, like the other members, like we see this come up time and time again. Like there's such value in that, that I just, it's, it's, again, it's hard to put a price on it. Um, but yeah, just being able to, to look at that differently than if you're like an employee or, or you're coming in, um, just kind of from a, from a solo lens. Uh, so it's, it's, it's fantastic that, you know, you guys have that, that opportunity, you know, to do that. 20:31 - Glenn Antoine Absolutely. And going through and talking about putting a good statement of work together for Atari, they may be contacting you to ask about remediating some legacy technology or doing a security audit or doing a code assessment to understand code quality and code vulnerabilities and all that. That's very seldom is that just didn't just wake up and decide they want to do that. What's the business reason for that? And the discussions where you're always taking it back to the business value and the strategic side of it, and tying that to, you know, the task. So keeping it very strategic, and then tying that back to the tactical things that need to be done, and then prioritizing that Because oftentimes you can find low hanging fruit that makes a huge difference as a value in a very short period of time. 21:37 - Donna Yeah. I love what you're saying about that. There's not just one way to engage with the CTO. There's not one way of doing this. It's looking at each individual situation and saying, okay, what is their problem? What is the possible solutions? Like what are the options to get us there? And it's not, it's not cookie cutter. It's not, as you said, like, it's not the same for everybody. So like, we love that the members can, can come in and they've learned to, to look at like every individual situation and say, okay, what's right for, for, for this particular company. Like, fantastic. 22:14 - Glenn Antoine I just had a conversation the other day, uh, this last week with a, uh, founder business owner, and he's all excited about some of the AI that they're putting in place. And I was like, cool. So I started asking questions and I'm like, all right. So at the end of the day, what, what are your efficiencies and what's the ROI? What are you getting out of this? And it's like, well, the, you know, these different workflows are getting easier and this and that. And I'm like, okay, great. So, so what I'm like, well, how do I measure that? How do we know that it's successful? 22:53 - Donna Mm-hmm. 22:55 - Glenn Antoine And he's like, you suck. He's like, why are you? 23:01 - Donna He burst his little AI bubble. 23:04 - Glenn Antoine But we started putting some metrics around it, and then we had something to drive towards. 23:10 - Donna Yeah. 23:11 - Glenn Antoine So, I mean, of course, AI is, everyone is looking at it. And so that's an easy one. Everyone wants to jump on the bandwagon. But what are you really getting out of it? And, oh, by the way, are you putting proper governance and security controls around it? 23:32 - Donna Yeah, you're absolutely right. Like, I think it's, you know, it's one of these hot topics right now. Everybody wants to jump into AI. And I think the difference, and other members have talked about this, is the difference if you're just the employee, you're just like, yes, sir, yes, sir. But when you come in as a fractional CTO, you're able to have that difficult conversation, you're able to have that pushback and ask the question, hey, where's the ROI in this? And if they can't provide the solution, then okay, let's get into this. So like very, very different approach than if you were just a regular W2 CTO for a company. 24:09 - Glenn Antoine Absolutely. So it's, I enjoy it. It's just, I It's rare that I don't get to the end of the day and A, I've learned something new and B, I've added value or helped someone in some meaningful way. 24:31 - Donna That's great. 24:33 - Donna That's so good to hear. So let's say 12 months from now, end of 2026, what does success look like, end of 2026? 24:45 - Glenn Antoine I am more engaged in just the aviation vertical and some of my support. I've got some, I've got a good network around me that are helping as additional contract support. Having them take some of the load off my plate and some of the other where it doesn't necessarily need my expertise. And I can just provide oversight and guidance. And so I'm still there as the co-pilot. They're handling the majority of it, but I'm there as the co-pilot to oversee, help with communications and that kind of stuff. And yet I'm focused a bit more on the aviation side. And I've had, two or three conversations over the past four to six weeks and had various colleagues go, um, you do realize you're the bottleneck, right? 25:54 - Donna A good thing about being a bottleneck, which was not something I anticipated. 26:03 - Glenn Antoine Yeah. That was, that was not even on my radar. 26:06 - Donna Yeah. Yeah. So, So with all of your knowledge and your experience over the last 12 months, what is one piece of advice that you would give to another CTO that was in your situation only a year ago and they're hesitating to go fractional? 26:29 - Glenn Antoine Wow. It is. First off, anytime you make a change like that, you're stepping outside of your normal box. So you've now stepped outside of your comfort zone. And that's always a bit intimidating, but what if you, and for me personally, and I would say this, I would venture to guess that pretty much every CTO, CISO out there. They have so much value to add. And what if they, you know, if I'm if I'm in one entity working, there's nothing wrong with that. Don't get me wrong. I've had some very fulfilling roles. The piece that I enjoy the most is the diversity of getting to solve different types of problems that I would never get to solve if I'm just in one place. So if you like being challenged a little bit and you like trying to solve new and interesting problems and you know, you want to kind of stretch out and you learn. You learn so much that I really think it's challenging to do if you're just in a single entity working. So if any of that intrigue you, jump. Build your parachute on the way down, just jump. 28:10 - Donna Just jump, build it on the way down. I love that. I love that. Well, thank you, Glenn. Now we have our Final segment. And as always, we're going to do something a little bit special. I'm going to ask Chat GPT live, right here, right now, for a thought-provoking Timely question, completely generated on the spot. And Glenn, you have to answer it. Are you game? 28:37 - Glenn Antoine Sign me up. 28:39 - Donna Okay, so let me bring up my chat GPT, our favorite. Hello, chat GPT. We love a bit of spontaneity. So we thought who better to challenge us than AI? What question would you like to ask fractional CTO Glenn? At this exact moment in time. Okay. All right, all right, it's thinking. Okay, here we go. Glenn, Chat GPT would like to know if every product you touched for the next year could only succeed or fail based on how well you communicated to non-technical stakeholders, to non-technical stakeholders, how screwed would you be? And what would you change starting tomorrow? That's a sassy question from ChadWT. 29:50 - Glenn Antoine Actually, I love this because on, in an M&A diligence, I have such a broad audience. I'm working with investors, I'm working with tech leadership, I'm working with C-suite, and then sometimes middle management. So, in my single discussion, I may have to change the way that I'm approaching all these answers. So, I'm well-equipped Because from an investment standpoint, it's not about the technical details of it. It's about what is the risk? What's the impact to being able to scale? How does it impact our investment thesis on down the line? So it's under the hood and at the bottom line, the technology but the investors they you know at the end of the day and many leadership at the end of the day they could care less if it's node.js or c-sharp or if it's an azure it's what are the costs what's my overhead can I scale it you know here's an important one can I hire new resources as they're needed If I'm using little abstract, I mean, every now and then we run across some very abstract technology or some strange language that somebody made up in their basement and someone thought it was cool and adopted it. It may be fine for that, but the chances of me being able to go hire a new resource, if that one decides to leave or they win the lottery or something, and they walk out the door, is incredibly challenging. So now all that tribal knowledge just walked out. So translating all that into the business strategy and how it applies to the vision and the investment thesis, that's a daily discussion. 31:59 - Donna That you're well-equipped for. That was a good question for you. 32:04 - Glenn Antoine It was. 32:07 - Donna It would be less nice to some of the others. 32:11 - Glenn Antoine And here's the thing, I get it wrong. 32:16 - Donna We all do. 32:16 - Glenn Antoine I mean, if I'm talking to someone that's been through enough cycles and they have some technical background and they understand some of the technology and a question is presented to me and it's slanted to the technical, the engineer in me, my initial reaction is to respond in the technical. And two weeks ago I responded and there was crickets for a minute and the gentleman on the other side was very gracious and he said, that was a great answer. Unfortunately, I understood about 20% of it. And I apologize. 33:01 - Glenn Antoine And I apologize and I say, That's my fault. 33:05 - Glenn Antoine And I said, I just, because of some of the phrases you used, I was like, Oh, we can go right to the tech. 33:11 - Glenn Antoine And so I re and he's like, Oh, when I rephrased it and summed it up the way I should have to start, he's like, that makes perfect sense. 33:21 - Glenn Antoine And, uh, it was very kind to me, but it was like the minute there was silence for more than a couple of seconds, I'm like, I went, I went way down the rabbit hole. 33:32 - Donna You knew exactly what you do, but you were able to put back. 33:35 - Donna And that's a sign of experience in that field. 33:39 - Donna So, Glenn, thank you so much. 33:42 - Donna I really, really appreciate you joining us today, sharing all your knowledge and insights. 33:47 - Glenn Antoine Thank you, Donna. 33:49 - Glenn Antoine It's been a pleasure. 33:50 - Donna Stories, experiences and advice you hear today are incredibly valuable, not just for CTOs, but for the broader tech community and leaders. 33:58 - Donna To our listeners, thanks for tuning in to Insight CTOx. 34:02 - Donna Don't forget to follow us on social media, tag us and share your favorite insights from the episode. 34:08 - Donna We love hearing your feedback. 34:09 - 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. 34:17 - Donna Until next time.