MilCom Founders Podcast, Episode 61: Building an AI-Run Newsroom After a $250 Million Exit with Nicolas Chaillan
Join host Rod Loges and guest Nicolas Chaillan as they talk about his time as the first Chief Software Officer of the US Air Force and Space Force and what he has built since. After selling Ask Sage to BigBear.ai for $250 million, Nicolas started Unbiased Headlines, a free news organization run entirely by AI agents, with no ads and no human editorial review.
- Nicolas describes starting Ask Sage in January 2023, shortly after ChatGPT came out, to bring generative AI to the Pentagon. The company earned FedRAMP authorization and Impact Level 5 accreditation in six months, which he says was unheard of for a small business, and BigBear.ai bought it in December 2025 for $250 million.
- He explains how he came to government work with no military background, not even knowing the ranks. After serving as chief architect at DHS, he reached out to Pentagon leaders on LinkedIn and brought DevSecOps into the Department of Defense.
- As the first Chief Software Officer of the Air Force and Space Force under Dr. Roper, he helped create Cloud One and Platform One, and he says hundreds of companies now do business with the Pentagon because of that work.
- He shares why AI scared him for the first time in January, after he saw tools like OpenClaw automate complex work from end to end. He has been coding since he was seven and says he hasn’t written a line of code since.
- Nicolas talks about how his three daughters run their own company, Quest Books, using AI agents to write picture books about their family trips. They take orders through Shopify and handle the packing and shipping themselves.
- He walks through how Unbiased Headlines works. AI agents pull from 110 sources and run each article through an 18 to 20 step fact-checking process, publishing about 150 articles a day with no human review.
- AI agents also built the company’s iOS and Android apps in one day, and they launched a daily podcast that went from idea to live in 48 hours.
- Nicolas breaks down the cost. He estimates the same work would take at least 150 people and a $10 million payroll, and he runs it for about $10,000 a month in AI tokens.
- He explains the sponsor model that keeps the site free with no ads. Companies pay for two sponsored stories a month, but the same AI agent writes them with no bias, and the sponsor can’t change the content.
- He tells founders that generalists who learn to direct AI agents now have about one to two years before the field gets crowded. He also explains why he thinks blue collar trades are safer from disruption than white collar work.
- He talks about his book, Replacement, which he wrote to give people practical tools to still have a job in five years.
- Generalists have an edge right now. If you know a little about many parts of the business, you can direct AI agents across all of them.
- AI agents only do as well as the person directing them. Nicolas could push his agents further on coding than on ad buying because he knew coding better, so keep learning the areas where you’re weakest.
- The barrier to building software is close to gone. If anyone can copy your idea in ten minutes, it isn’t a business yet, so build around something you understand deeply.
- You may not need to raise money. Nicolas says a founder can now build a business for a few hundred dollars in tokens instead of spending months raising a seed round.
- The window is short. Nicolas thinks founders have about one to two years before everyone is building the same things and it gets much harder to stand out.
- It’s hard to stay hungry once money isn’t the reason. What keeps Nicolas building is caring about the problem, which for him is media bias.
- LinkedIn: https://www.linkedin.com/in/nicolaschaillan/
- Website: https://unbiasedheadlines.com
Nicolas M. Chaillan is a serial entrepreneur, cybersecurity expert, and former senior U.S. government technology leader. He served as the first Air Force and Space Force Chief Software Officer under Dr. William Roper, bringing DevSecOps, continuous Authority to Operate (c-ATO), and modern software practices across the entire Department of Defense.
In January 2023, he founded Ask Sage, Inc., the first generative AI platform to achieve FedRAMP High Authorization for government teams. Ask Sage was acquired by Big Bear.ai in 2025 for $250M, and Nicolas served briefly as Big Bear.ai’s CTO before departing in February 2026.
In 2026, he founded Unbiased Headlines (UnbiasedHeadlines.com), an independent news organization built on one promise: Facts. Not Spin.
Previously, he served as Special Advisor for Cloud Security and DevSecOps at the Department of Defense and Special Advisor for Cybersecurity and Chief Architect for Cyber.gov at the Department of Homeland Security.
Nicolas founded 14 companies starting at age 15, created and sold over 187 innovative software products to Fortune 500 companies, and is recognized as a pioneer of PHP. He has over 25 years of experience in cybersecurity, software development, and government modernization.
He is currently focused on building Unbiased Headlines (UnbiasedHeadlines.com), AI investing, and hosting “In the Nic of Time” on LinkedIn and YouTube. He is the author of “Replacement”, a book on AI’s impact on the workforce.
The MilCom Founders Podcast champions and celebrates military community business founders. Each episode brings practical insights from successful veteran entrepreneurs.
Sponsored by One Degree Financial www.onedegreefinancial.com
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