Air Traffic Control Is Running on Windows 95 | Dan Rickert | Ep. 469
September 14, 2026
AI Summary
5 min readAir Traffic Control Is Running on Windows 95
Dan Rickert spent nine years in the military—cavalry officer, then Green Beret—before transitioning to Palantir and eventually becoming chief of staff at the defense tech company. Today he's at Airspace Intelligence (ASI), a software company that just won a major contract to rebuild the FAA's air traffic control system. The punchline he delivers early in the conversation: some of the critical systems managing American airspace are still running on Windows 95-era software.
The State of the Systems That Keep Planes Apart
Rickert's company builds "software engines for critical industry." They started with commercial airlines, optimizing flight routes and network management, then moved into energy sector work and Department of Defense contracts. The core capability is modeling complex geospatial networks—understanding the health of hubs, the movement of assets across those hubs, and the environmental variables (weather, wind, congestion) that affect decision-making.
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What you'll learn
- 1 (00:00) **Opening Banter & Guest Introduction** - Casual conversation about the host's son's 21st birthday and the guest's background.
- 2 (03:37) **Biggest Threat to the US & Defense Tech Misconceptions** - Dan identifies internal division as the primary threat and defends the defense industry's intent.
- 3 (10:44) **The Challenge for Small Defense Startups** - The discussion covers how small companies compete against massive primes like Raytheon and Boeing.
- 4 (14:56) **Critical Infrastructure Runs on Windows 95** - Dan reveals that many critical government systems are decades old, creating a need for modernization.
- 5 (16:01) **The Evolution of Drone Warfare** - A conversation on the shift from Predator drones to small, FPV drones and the psychological impact of different combat roles.
- 6 (19:56) **Locus of Control in Transition** - The discussion pivots to how the loss of control in leaving the military mirrors other life challenges.
- 7 (24:25) **Path to Service: West Point & Family Influence** - Dan recounts his upbringing, the influence of 9/11, and his decision to attend West Point.
+ Full timestamped outline available in the app
Show Notes
Dan Rickert graduated from West Point and commissioned into the cavalry, running Bradleys and gun trucks through Iraq in 2008 before going to selection and finishing his nine years in uniform on a Special Forces team with 10th Group. He left the Army in 2015 and spent the next eight years at Palantir, moving from project management to international work and eventually to chief of staff on the defense side. He is now VP of Operations at Air Space Intelligence, the company the FAA selected to rebuild the software that runs the national airspace.
Much of this conversation is about what people get wrong about the defense industry. He argues that competition produces a better product for the people using it, that a human has to stay in the loop on any decision that matters, and that skepticism is healthy either way. We also worked through privacy and security, and whether the two actually have to be traded against each other.
From there we covered drone warfare and trench fighting in the same conflict, rebuilding an identity after the uniform comes off, and the work of modernizing air traffic control.
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