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Founder & CEO, Cypress Jet

I design journeys for people who've already tried doing it themselves.

Three years in private aviation, on top of fifteen-plus years earning the trust of executives and founders in technology sales, now channeled into building Cypress Jet. I started this company because too much of this industry optimizes for commissions instead of the client, and I wanted to build the version that doesn't.

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EVERY ENQUIRY READ PERSONALLY · RESPONSE WITHIN 24 HOURS · STRICTLY CONFIDENTIAL
Steve Simard, Founder & CEO of Cypress Jet
3 YRS
Private aviation experience
15+ YRS
Building client relationships
5 YRS
Marine Corps aircraft mechanic
24 HR
Enquiry response window
Recent Journeys

A small sample. The rest stay off the record.

Most of my work is arranged under strict confidentiality and never shown publicly. What follows is a representative sample of the kind of journeys I build. Client details are anonymized by design.

NYC→AMALFI
ClientFounder, family of four
Duration9 days
ArrangementPrivate villa + day charter yacht
Notice11 days

"Rebuilt the itinerary twice around a storm system. The clients never knew there was a problem to solve."

BOARDING · CONFIRMED
LON→KYOTO
ClientRetired executive, solo
Duration12 days
ArrangementPrivate ryokan buyouts, cultural immersion
Notice3 weeks

"He wanted silence, not sightseeing. The whole trip was built around that one instruction."

BOARDING · CONFIRMED
MIA→ST. BARTS
ClientFamily office principal
DurationLong weekend
ArrangementFull villa staff, chef flown in from Paris
Notice96 hours

"Confirmed with four days' notice. The chef's flight was the hardest part. The villa was already ours."

BOARDING · CONFIRMED
LAX→QUEENSTOWN
ClientTech founder + partner
Duration10 days
ArrangementHeli-skiing, vineyard stays, private chef
Notice5 weeks

"Their only brief was 'somewhere neither of us has been.' I gave them three options. They took all three."

BOARDING · CONFIRMED
Steve Simard, Founder & CEO of Cypress Jet
About

Fifteen years earning trust. Three years spending it on you.

I spent over fifteen years in technology sales, building long-term relationships with the same kind of clients I work with now: executives and founders who've stopped tolerating guesswork from the people they hire. That's where I learned what it actually means to put a client first.

Three years ago, I moved into private aviation and built my approach on that foundation. Now I'm founding Cypress Jet on that same standard, after watching too many advisors in this industry optimize for their commission instead of your trip. I didn't come from a travel background originally, and I've come to think that's exactly why this works. I'm bringing that discipline in, instead of inheriting the old one.

  • ✓Fifteen-plus years building trust with executives and founders, long before the first itinerary
  • ✓A client-first standard imported from outside the travel industry, not inherited from it
  • ✓Every client relationship covered by a standing confidentiality agreement
  • ✓A deliberately small client list: availability, not a sales funnel
Working Together

No forms. No template itineraries.

Every journey starts as a conversation, not a questionnaire.

01 / CONVERSATION

We talk it through

A short call covering what you want the trip to feel like, what's non-negotiable, what's flexible. No forms to fill out first.

02 / PROPOSAL

You get one itinerary, not ten options

I don't send a menu of choices to sort through. You get a single, considered proposal built for you specifically.

03 / JOURNEY

I stay reachable the entire trip

If anything changes mid-trip (weather, a closed venue, a change of mind), I handle it before you notice there was a problem.

In Their Words

What clients say once they stop planning trips themselves.

"

I've used two other advisors before Steve. He's the first one who asked what would ruin the trip for me before asking where I wanted to go.

FOUNDER, PRIVATE EQUITY · CLIENT SINCE YEAR ONE
"

Something went wrong with our villa two days before departure. I only found out about it after it was already fixed.

FAMILY OFFICE PRINCIPAL
Start Here

Start with a conversation.

No forms to fill out beyond this. Tell me what you're dreaming up, and I'll read it myself, usually within 24 hours.

Prefer to skip the form entirely?

steven@cypressjet.example +1 (000) 000-0000, call or text
Read personally. Always confidential. Response within 24 hours.
Operating carrier, our role in the transaction, and insurance details are disclosed in writing before you're bound by any contract.
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