Startup Junkies Podcast
My Conversation on the Startup Junkies Podcast
I recently had the chance to join the Startup Junkies Podcast for a conversation about aviation, entrepreneurship, and the unlikely role Northwest Arkansas is beginning to play in the future of aviation technology. What started as a simple interview became a great opportunity to reflect on the journey so far — and where Flying Company is headed next.
Below is a recap of some of the major themes we covered.
From Failed Child Actor to Air Force Pilot
When Daniel asked about my “origin story,” I shared something most people don’t know about me: I grew up just outside Manhattan, surrounded by actors. Aviation wasn’t part of my upbringing at all.
Everything changed after 9/11. I decided I wanted to serve, and after a long conversation with my mom, I chose the officer route and joined Air Force ROTC. That decision led to a 14-year career in Air Force Special Operations as a pilot, instructor, evaluator, and eventually a deployed squadron commander.
Those years shaped nearly everything about how I operate today — discipline, humility, quiet professionalism, and the stubbornness to keep working until something works.
The Pain Point That Started It All
When I transitioned out of the military, I stepped into the private aviation world as a chief pilot managing a business jet in Bentonville. I quickly realized something:
Finding pilots in the private sector was broken.
The process was shockingly outdated:
- Posting for pilots in Facebook groups
- Piecing together certificates, ratings, medicals, training records, and personal documents
- Manually verifying everything with insurance
- Providing scattered trip details
- Signing a pilot services agreement
- Looping in accounting
- Waiting 30–60 days for pilots to get reimbursed or paid
What was a simple ask (“I need a copilot next Wednesday…”) turned into a week of admin work before every trip.
I built a scrappy alpha version of a platform to solve this for myself and shared it with friends. It worked. Then I iterated. Then it grew. That was the beginning of Flying Company.
What Flying Company Is Today
Flying Company has evolved into a true marketplace and management platform for business aviation. The way I described it on the podcast was:
“It’s like care.com — but instead of finding childcare, you’re finding pilots.”
Operators can:
- Build their fleet
- Create a trip
- Receive standardized quotes from qualified pilots
- Assess pilots in a clean dashboard (certificates, ratings, hours, insurance compliance, quotes)
- Message, hire, sign agreements, and pay through Stripe
- Receive matching invoices
- Let us handle 1099s at year end
For management companies, dispatchers, and flight departments, we’re saving five hours of touch time per event and several days of cycle time.
For pilots, we’re providing faster information, more transparency, and reliable payment in three days, not sixty.
Aha Moment: Enterprise Needs This Even More
For a long time, I assumed that Fortune-500 flight departments and major management companies had robust hiring and staffing systems.
They didn’t.
When one manager told me that a huge management company gave him a “list of two pilots to call,” I realized the market was far more broken at the enterprise level than I had originally considered.
That shifted the entire trajectory of Flying Company. Today, we’re onboarding multi-aircraft fleets and partnering with organizations that manage dozens or hundreds of jets. The need is real — and far larger than I expected.
Looking Ahead: The Next Five Years
Our roadmap is ambitious but focused:
1. Expand aircraft support
We’ve gone from 2 models to 30. Next up: Embraer, Gulfstream, Bombardier, Dassault.
2. Move into full-time staffing
Once you build a trusted database of thousands of pilots, it’s natural to help them find full-time roles too.
3. Build a true pilot career progression platform
From student pilot at 16 to at 65, I want Flying Company to support a pilot’s entire professional journey.
4. Elevate safety and professionalism
Simply put: hours are a terrible proxy for skill.
We’re building tools that highlight training, professionalism, and safety — not just flight time. And we expect to share more about this soon.
Want to Listen to the Full Conversation?
You can find the full episode on the Startup Junkies Podcast across Apple Podcasts, Spotify, and YouTube.
