Then I learned the other side of trust.
I spent the next fifteen-plus years in technology sales, working with executives, founders, and other people whose time was valuable and whose tolerance for a sales pitch was understandably low.
I learned pretty quickly that the best relationships weren't built by selling harder.
They were built by listening.
Remember what someone told you the last time you spoke. Understand what matters to them before recommending something. Don't make them repeat themselves. Don't waste their time. And tell them the truth, even when the truth isn't the answer that makes you the most money.
Do that consistently enough, and something changes.
"You stop being someone they buy from. You become someone they call."
That distinction ended up mattering a lot when I found private aviation.
Private aviation showed me what was missing.
I entered the industry three years ago, almost by chance. I was ready for something new after technology sales, and the fit was immediate.
I learned the aircraft, the operators, the economics, the safety standards, and the mechanics of charter. But the part that came most naturally wasn't finding airplanes. It was the client relationship.
And something kept happening.
Clients who had flown privately for years started calling me directly. They stayed with me when they had plenty of other options. They told me things that had nothing to do with an itinerary because they knew I'd remember why those things mattered the next time they called.
Some eventually told me I should start my own company.
They weren't asking for another charter broker. They were asking to keep the relationship.
The longer I worked in private aviation, the more clearly I saw the disconnect. These were people who could access almost anything, flying on aircraft that represented the highest end of travel, yet the relationship surrounding the experience could still feel remarkably transactional.
A different representative. The same questions again. Another quote. Another trip. Start over.
I thought private aviation could be better than that.
So I built Cypress Jet.
Cypress Jet brings together the two sides of trust I've spent my career learning.
The Marine Corps taught me the standard: be prepared, take responsibility, and execute when people are counting on you.
Fifteen years in sales taught me the relationship: listen, remember, tell the truth, and earn the next call.
Private aviation showed me where both were needed.
That's what we're building here.
We want to know how you like to fly and which aircraft you don't. Who usually travels with you. Your dog's name. Whether you care more about finding the smartest value or getting the newest aircraft available.
And we want to know the things that aren't really about aviation at all.
Maybe there's a meeting you absolutely cannot miss. Maybe you're making the same trip every week for a reason you don't want to explain every time you call. Maybe your arrival time matters more than usual because someone is waiting for you on the other end.
Those details are part of the trip, too.
The longer we work together, the less of that you should have to tell us again.
United States Marine Corps
Two voluntary combat tours in Iraq: perimeter security, then CH-46 field maintenance. Promoted to E-5 in 3.5 years.
Built on relationships
A career in technology sales spent earning trust with the same kind of clients I serve today.
Moved into private aviation
Trained, then outpaced peers with years more tenure by building my own approach on that foundation.
Cypress Jet is founded
Built around one standard: put the client first, every time, without exception.
