Nicolas M. Chaillan Podcast Transcript
Nicolas M. Chaillan joins host Brian Thomas on The Digital Executive Podcast.
Brian Thomas: Welcome to The Digital Executive. Today’s guest is Nicolas Chaillan. Nicolas Chaillan is a serial entrepreneur, cybersecurity expert, and former chief software officer of the US Air Force and Space Force. He led the modernization of software practices across the Department of Defense. In 2022, he founded Ask Sage, one of the first generative AI platforms to achieve the highest security authorization level in the Department of Defense.
The company was acquired in 2025 for $250 million. Chaillan has founded 13 companies since age 15, starting his first in France, built and sold over 180 software products, and brings more than 25 years of experience in cybersecurity, software development, and government modernization. He published Replacement, a 2026 bestseller, and recently founded Unbiased Headlines, an independent media organization managed 100% by AI agents.
Brian Thomas: He manages his investment portfolio and raises his three daughters. Well, good afternoon, Nic. Welcome to the show.
Nicolas M. Chaillan: Thanks for having me.
Brian Thomas: Absolutely, my friend. I appreciate it. I’m really excited. You’ve got such a, an illustrious career. Worked in the Pentagon, obviously, as the chief software officer, et cetera, and we’ll go, kinda go into that.
But if you don’t mind hailing out of Orlando, Florida, I’m in Kansas City. Just really appreciate the time. Let’s jump right into it, Nic. Yeah. You’re a self-taught programmer who started coding at the age of seven in Marseille, France, and founded your first company at age 15, which is amazing. Going on to found 13 companies and ship over 180 products before becoming the first chief software officer of the US Air Force and Space Force.
You’ve said AI wasn’t a career pivot. It was the same instinct: build the thing, sell the thing. Walk us through that arc, if you don’t mind. How did a serial entrepreneur from France end up reshaping software across the Pentagon?
Nicolas M. Chaillan: Well, as you can imagine, it’s pretty rare to get a, a French born citizen in the Pentagon. In fact, I, I don’t think there were any others. And the chief software officer role is, is so critical to be able to consolidate kind of the software vision and also the delivering the, the speed we need to be able to move at the pace of relevance in, in the Pentagon. And, building software for jets and bombers and space systems and nukes is quite complex.
And coming from industry, that was, for me, a, a big shift. But, it was very interesting to be able to bring the entrepreneurial skill that I, that I have to really kind of reshape the way we build software be able to do over-the-air updates like, Tesla does, but on jets which was, amazing.
And also enable software to become kind of the differentiator in the next battle so that, wolf fighters have a chance of, winning the next war. So that was probably the best three years of my life, but also the most frustrating ones, because y-y-you have high stakes. I– The pace of the Pentagon is, is always challenging.
I, I send people Pentagon leaders to SpaceX, and I would joke that, if I leave them there for two weeks, their brain would implode because they, they can’t comprehend the, the velocity and the speed of SpaceX compared to what, we do at the Pentagon. And, you know, we, we have these two bubbles, right?
The the complacency bubble, as I call it, in the Pentagon, and the kumbaya bubble in the Silicon Valley, where they don’t really understand what’s going on in the world, and they don’t understand China and the challenges there and how we need to win. And, and that was always super interesting to try to pop, both bubbles so we have actually a chance as a nation to, to win against the, the Chinese Communist Party who, you know, who they’re, they’re not waiting for us to figure this out.
So, AI is just like this next big challenge that we can’t a-afford to, to miss, but it’s also gonna disrupt everything we know. It’s, it’s for the first time, actually, in, in January, when we moved to AI agents and real end-to-end agentic work where, we went from, augmenting humans to replacing them.
Whether we like it or not, it’s happening. And that is, for the first time, something that actually scares, scares me and, and, for the future of, of my kids and, and the nation. So that was a big disruption in my life when, when finally, AI was able to completely replace coders and designers and accountants and, and a lot of other jobs.
Brian Thomas: Absolutely. And I appreciate you sharing some of the responsibilities you had obviously in the US government. And, and I agree, I worked in local government for a, a, a while. But big difference in private sector the pace. It’s, it’s, it is frustrating, but, Right … you did such a great job there. And I, I agree, AI is right now at the forefront and I think we need more guardrails in place.
I love the technology, but it, it’s getting a little bit out of hand. And you’re right China’s not waiting for us. So, thank you. I appreciate that. So Nick, as the first ever Air Force and Space Force chief software officer, we talked about that, you drove DevSecOps continuous authority to operate and modern software practices across the entire Department of Defense.
You famously left in 2021 frustrated with the pace of change. We talked about that. What did the experience teach you about why government modernization is so hard, and what did you accomplish that you’re most proud of?
Nicolas M. Chaillan: It’s very tough to make stuff stick in the, in the building, when the new administration came in you have new leaders appointed, and I was reporting directly to those appointees.
And it’s very frustrating, when you spend, three years kind of educating and, and teaching the leaders why all this matters. And then you get new people that often don’t really understand any of it, and, and, and you’re starting almost back from zero. And after three years, I also started to feel like I was becoming part of the problem.
I think it’s super important that you don’t become yourself complacent. And when you spend, three years in the building, and you’re starting to get used to the, the lack of velocity of, of the place and you start to forget what is normal and what is a normal deadline, and, and I would start shifting my timelines.
And then I realized, wait, maybe it’s time for me to go back to the commercial side, do more things, and then maybe come back, right? And the first time around, it’s very difficult to actually make an impact because you spend two of the three years to learn how the building works and what, what you need to do, right?
So, and understand the problems, which are very complex problems. That’s why you saw, the Dodge thing was a disaster, right? They brought mostly young kids that were mostly too arrogant to listen to people to, to do what’s right and understand what’s going on. I was arrogant, too, don’t get me wrong, but at least I was listening.
And, and also I had a, I had a more experience, right? I was a little bit older, although I was still, 35 or whatever. But they, I took about 18 months to understand what’s going on. I wanted to move fast, but, those are the reality of the situation. And then, then you get 18 months to get stuff done, and then you have a new administration, and you have to restart everything, and then you get questions like, “Oh, should we invest in cloud or laptops or, or network?”
And I’m like, “We need all of it, I don’t know what you’re talking about.” So it’s not a, it’s not a decision point, you, you gotta, you gotta fund all three, and, and when that’s the kind of decision that you hear the new administration, back then talk about and, and a lot of those people were, coming in in the building, that is very frustrating, and I couldn’t do, I couldn’t do another, another three years of, of educating.
So I thought it was pretty healthy for me to, to leave. And, and my hope is, particularly having sold a, a company, now my, my 13th company having enough money not to care at all. I didn’t care before, but now it’s really, like, obvious. And, and, I, I think you can make a huge impact when, when you go in and you, you don’t ask for forgiveness, you just get stuff done.
I, I find it, everybody was talking about firing me all the time, but they never did, right? So, I, I think you can, you can get a, do a lot of good if you actually don’t think about what’s next in your career, and you’re not trying to get one of those cushy jobs, in some of the defense contractor primes after you leave the building, so.
Brian Thomas: Amazing. Thank you, and I appreciate that. You did highlight some things that were very frustrating in your time there. Obviously, we know how that works. Politics, unfortunately, is… It’s just really not always a fun place to work. When you have administration changes, leadership changes, and I know people mean well, but again, that’s just just sometimes such a mess, and it moves so slow.
So I, I can appreciate that. But you’ve done some great work, and, and that’s what we appreciate the most, and, and I’m glad that you’re able to focus on your own endeavors right now, so thank you. And so N- Nick, let’s talk about askSage. You founded it in 2022 and made it the first generative AI platform to achieve FedRAMP High authorization, eventually serving over 100,000 users across the government defense before selling it.
What gap did you see that no one else was filling, and why were you able to move so fast in an environment famous for moving so slow?
Nicolas M. Chaillan: It is very difficult to get software accredited in the, in the Pentagon and, and even in the US government, right? And if you build it right from the get-go, it’s actually pretty easy if you understand what you gotta do.
But most people don’t know what they gotta do anyways, and companies, when they build software, they don’t particularly think of the, the US government as a prime target. Which, makes sense. It’s expensive, and you gotta know a lot of things to make things happen to get contracts with the US government.
So with me, I was lucky enough to have spent three years in the Pentagon and know what you gotta do. So, that barrier to entry of like, understanding what needs to be done was not there. So… And I knew if I didn’t do it, and I knew the power of the technology right away after using it for a few weeks, I knew I had to bring it to the Pentagon so we have, a fighting chance of, of the Pentagon getting access to it when China was already starting to use, you know GPT stuff across the, the, the agencies.
So we had to do it. And within four months, I had a, I had a complete capability online and ready to go. It took it took about another, probably five to six months to get it authorized, which was way too slow. Particularly for someone like me, despite everything I know, it still took way too long which tells you there is still massive bottlenecks, in, in software authorization.
But we got, like you said, FedRAMP High. We’ve got it on the secret networks, the top secret networks, which was also, a, a big achievement. And what was important with Assage is we were bringing all the models. We– I, I know from experience with clouds and other things that you don’t know who’s gonna win.
You wanna have access to all, all the best of breed capabilities. You don’t wanna be locked in. And that, that was a big thing for me with Assage. We, we brought all the models, all the, the frontier models, all the open source models. And, and then, we, we got a great buyer with Big Bear publicly traded company, amazing people that can take it to the next level.
I knew it was time for me to also, after three years, it was perfect timing to give the baby to, to someone that can actually take it to, to the next level. And, and they’re doing that. You know, unfortunately, the Pentagon- A current leader. I’m not that great in, in AI. They’ve, they’ve burned bridges with Anthropic, calling them a, a national threat, which really makes zero sense.
They were actually the biggest partner of the Pentagon for years across all classification levels, and really did nothing wrong, right? And, and that, A- and shooting ourself in the foot for stuff like that is, is very shortsighted. I think it’s gonna, it’s gonna be a massive impact to startups willing to work with the Pentagon now when you can have a target like this, and if you don’t behave, they’re gonna, they’re gonna label you a national security threat and, and blacklist you from the world.
That, that, that is just a terrible precedent and, and very shortsighted thing. And, you know, people are gonna say I’m anti-Trump or whatever, which is nonsense, right? I was appointed by President Trump during my first term. So, y- clearly, I, I, that’s… I’m gonna say what I think is right, regardless of the party making the mistakes, and I’m a Republican, and despite that, I, I, I still think that was a, a massive mistake and, and very shortsighted.
And then they, they doubled down by creating this kind of GenAI.mil new capability where they only have one model each and, and it’s like different websites. So if you wanna go to ChatGPT, you go to ChatGPT. If you wanna go to Claude… And so if you build agents, that’s not gonna work, right? ‘Cause you wanna have an agent that can tap all the models in one place and be able to train data once and be able to tap all the models.
And so the whole concept is, is broken. It’s completely nonsense. But, we joke about this stuff, but we don’t understand the, the cost impact and the, the, the global impact on the war fighters not having those capabilities and also getting locked into, like, Google, right? The, the, the cost of that stuff.
They, they gave it away for a dollar, by the way, which was very shady, right? You don’t do that in the government. In fact, it’s the first time it’s happened where OpenAI and Google and all these companies gave unlimited access to their models for a dollar for a year with no plan of, what’s next and how much it’s gonna cost once it’s time to renew, and the time to renew is now.
And now it’s like, “Oh, we don’t have the funding.” Okay. And now you’re locked in, right? So these shenanigans should never have been allowed. The, the government officials’ duty is to protect the, the interests of the taxpayer and the funding of the, the, the Pentagon. And clearly that was completely amiss.
They, they wanted a quick win to pretend they were doing g- cool, cool stuff with AI and, you can’t trade off common sense for quick wins. That never sticks, and the, the impact of that kind of stuff ends up in the billions, right, with a B. And, and, and that is something that, as taxpayers, we should be pretty upset about.
Brian Thomas: Agreed. Thank you. Gosh, you impact so much there and I appreciate that. You talked about, how to really get things moving in the, the government. As you know, took you many months to get Ask Sage even approved. But the bigger thing is what I took away and, and just real quick, is the fact that you’ve got these segregated environments, as you talked about, with the different models.
And here we are trying to make our war fighters successful in their jobs, and when we’re limiting them or giving them substandard tools to be successful in what they do that, that’s not a good thing. And I’m with you there 100%. And, and you spoke up and you spoke eloquently and honestly, so thank you.
I, I, I do appreciate that. And of course, the last question of the day. Nick, if you could briefly share, you’ve said AI is the most powerful tool you’ve ever seen. Now you’re managing unbiased headlines, your portfolio, raising your three daughters, and hosting In the Nick of Time. You have a bird’s-eye view of where this is all going.
If you look maybe, let’s say, five, 10 years out, maybe too long, but what excites you most and what worries you most about AI, and what should govern- leaders in government and industry be doing right now to be ready for it?
Nicolas M. Chaillan: Well, you know, I, I’m gonna start with the scary part, right? Back in January, I started using OpenClaw, which is kind of this open source harness to manage AI agents.
And for the first time, you would move from augmenting people, which, you know, at our stage, we would easily turn one quarter to 50x velocity, so five-zero, which is, which is insane. But for the first time in January, I could actually automate end-to-end tasks. In fact, I started coding, like you said, at seven.
I’m 42, and for the first time I have not coded a single line of code or looked at a line of code in nine months since January, which is, which is scary, right? And so when you s- that’s why I, I decided to write, my book, Replacement. I wanted to bring the tools for people to be able to have a chance of, having a job in five years particularly in white-collar jobs, right?
Too many people made fun of blue-collar jobs, not me, but many did, and, and we’re gonna pay that price. But, Replacement was written to first explain a little bit about me and, and, like, what’s going on and, and the cyber risk, the, the Chinese risk. But then I dig, deep dive into the skills you need to build, right?
And a lot of it is what I had to do because I didn’t go to school, created my company, I was 15. And, you have to, to have this self-learning and eagerness to learn and reinvent yourself. Now, you could get away with it back then, to doing it maybe a couple of times, every five years or whatever.
But now it’s like every six months, right? It, it, the, the, the pace of IT is insane. And so you have to have the skills to learn without someone holding your hand and telling you what to do and, and, and, and that someone, by the way, could be an AI agent like mine telling me what to watch every week so I can keep up and see what else is coming to, to disrupt my my day-to-day.
But You know, so, so that was a big moment in January. We wrote the book in five days. By the way, bestseller, right? People love it. But it’s not a doomsday book. I mean, it’s a little scary, but it tells you what to do. But then, right, I, I… my dad is a journalist. He’s retired now, but you know, it always mattered to me and the media, and I, I felt that the, the nation is divided.
And I think a big reason as to why this is happening is, people not getting facts and, and opinions on, on the left and the right and CNN and Fox News, and they’re, they’re, they’re crumbling. I mean, you go to those websites and you see the number of ads they have. It’s mind-boggling to me that anyone can even go on the website and stay there.
It is just like bombarding you with pop-ups and ads when you’re scrolling. It’s unusable. So I said, number one, free, no ads. We’re gonna build, you know, Unbiased Headlines, and it’s gonna be… Initially, I built it for me because I just wanted to get the news, and it was so good and so awesome that I said I, I have to put it out there.
And now we have 400,000 users in five months. And and it’s, it’s AI agents with 110 sources and social media and whatever, and it’s pulling the sources. It’s writing factual article, 150 articles a day, which is insane. You would never be able to do that with people without spending, 10 million bucks of payroll.
And then it built the iOS app, the Android app. And by the way, the AI agents built it end to end with no human intervention and published it on the stores, including, Chrome extensions and Alexa apps and all this stuff, managing the ads, managing the marketing, managing the, the releases. And we have no ads in the app.
It’s completely free. No subscription. We get sponsored articles, but it’s more like op-eds and, and, stuff that AI agents still write. So it’s not even humans writing so it’s never biased. It, it’s always balanced. It’s always factual. And people love it. And we just will launch a podcast where people can listen to it if they prefer to listen.
We have a video format. You know, it’s, it’s all this stuff. What, what is mind-boggling to me and, and, and I could– I didn’t even think it would be possible, is to have this end-to-end company, right? Fully managed by AI agents. I think it probably replaces, unfortunately, whether we like it or not, 150 jobs that I would have to, to…
Which I, I probably couldn’t do anyways. Don’t get me wrong. I, I would not have the funding, and I would not be able to do this free offering and no subscription if, if I had to pay 10 million bucks of payroll, right? So, so the reason why it’s even possible to do it is because it’s driven by AI agents. And so unbiasedheadlines.com, you know, it, it, it is So insane to me, the, the quality of the, the, the pieces, but also you can see the sources, you can see, all the facts, and then you have all these format, audio, text, video.
And, and, people love it. And what I love is no ads. I mean, going there and not be bombarded. I don’t even know how people go to the other websites because it’s in your face 24/7, so.
Brian Thomas: I, I, I really appreciate that. That’s, that’s amazing. And I, I’m the same way. I do not like… I, I mean, and I work in publication as well.
I do a lot of work. I’ve, I’ve written for cio.com and other big publications. And every one of those publications have in-your-face ads, and it’s, it’s just clutter. It slows down the site, and it, your ex- the, the user experience, not… It’s just not good. Right. And so just like you, my tech publication is the same way.
No ads. We, we wanna keep that clean and crisp and I totally get it. And I appreciate what you’re doing. Brother, this is amazing for you to have the just the fortitude to get out there and be a game changer. You’re a pioneer in this space, and I wish you the best of success.
Nicolas M. Chaillan: Oh, thank you.
Brian Thomas: Awesome. Well, again, Nick, it has been a pleasure having you on, and I look forward to speaking with you real soon.
Nicolas M. Chaillan: Thank you so much for having me.
Brian Thomas: Bye for now.
Nicolas M. Chaillan Podcast Transcript. Listen to the audio on the guest’s Podcast Page.
