Seamlessly transition into a fulfilling civilian career.

Uncover your internal drivers and instinctive strengths with resources built for veterans and their civilian employers.

Leaders in the military are leaders everywhere.

You swore an oath to support and defend the Constitution of the United States against all enemies. With less than 0.5% of the population willing to make that commitment, just by doing so, you set yourself apart.

But as your military career progresses and the dynamics of your personal life evolve, you start to wonder, “What’s my trajectory here? Should I stay in the 20 years? If not, what else would I do?”

Enter Five & Fly. We are here to help you, and your employer, achieve success off the battlefield. With us as your battle buddy, you’ll go from:


Meet Daniel, separated Captain and the founder of Five & Fly.

As an unconventional leader passionate about building teams that catalyze growth, I was ready for a new challenge after serving our nation for five years.

My transition from the US Army to civilian life was anything but seamless, not for a lack of effort but for a lack of career support resources, coaching, and accountability.

Where the US Army has filled the gap to help soldiers transition, they are missing the mark when it comes to the nuances officers face. I’m here to coach you through that process.

How We Help Service Members & Their Civilian Employers

We empower active duty service members and veterans to seamlessly transition into fulfilling civilian careers. We do this by helping them and their employers understand internal drivers and instinctive strengths through data-validated assessments, personalized training, and long-term accountability.







Five & Fly aims to prevent veteran suicide in the five years following military separation by empowering veterans to find fulfillment in their civilian careers. We serve veterans and their civilian employers with intentionality, unconventionality, and longevity in mind.