Bill Williams is Failing Daily

Inspiring Entrepreneurs through Failure….and Humor

Entrepreneur, retired Air Force Lt. Col., and CEO. Everything I'm working on, in one place.

Join the Failing Daily community

Talk shop with founders and GovCon operators, share what isn’t working, and help shape the 2027 road trip.

Join the community on Discord ↗

The 2027 Failing Daily road trip

AI Can’t Shake Your Hand

Building something for 2027. AI planned the route. It can’t shake your hand. That part’s on me.

#AICantShakeYourHand #ShakeHandsFD

How 10 Kids

All shorts ↗

Failing Daily, the show

All episodes ↗

Roundtables

Short takes

Two minutes on the things that actually go wrong.

About Bill

I'm a history major who ended up running a technology company. That should tell you what I think of plans.

I own and run IPTA, a federal technology integrator. We work for the Department of Defense, the Department of the Air Force, Army Futures Command and the FAA. Agile, cloud, data science, IT and cyber. I ran business development and operations from 2005 to 2015, which put us on the Inc. 500|5000 list. I bought the company in 2015. In 2022 we won the largest VETS2 task ever awarded, supporting the Army's Aviation and Missile Command in Huntsville.

There’s also Staffility, where government contractors find and keep talent, and Blue Orbit Global, which builds edge devices that talk over Bluetooth and satellite. Pharmaceutical cold chain on one side, defense on the other. I started B2 Medical, a medical staffing firm, along the way.

Before any of it I was in the Air Force. I retired as a Lt. Col. after serving as an acquisition officer, an ROTC instructor, and a liaison officer to the Air Force Academy. B.S. from the Academy. M.B.A. in entrepreneurial studies from Northeastern.

That list leaves out everything that didn't work. There was plenty. That's what this site is for.

On the Road

2025. I got in the car and drove — the passenger seat turned out to be the best interview room I've ever used.

The series ↗
7Weeks
6,000+Miles
38Stops
23States

What else I'm building

Join the Failing Daily community

Talk shop with founders and GovCon operators, share what isn’t working, and help shape the 2027 road trip.

Join the community on Discord ↗