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Stephen Simpson.

How did you end up in the Pensacola area?

I’m a Navy brat. My mother, a native Pensacolian married my father after flight school at NAS Pensacola. I was born in Philadelphia and spent my childhood bouncing to different duty stations, but always spent summer vacations in Pensacola. My company, Heliworks originated out of upstate New York.
Helicopters needed to be inspected annually for serviceability and required special equipment, so I flew the helicopter from NY to Peachtree DeKalb for my annual inspection. I noticed a US map on the wall with different colored pins showing cities throughout the southern region and discovered the green pins represented where we have active contractors. I exclaimed, “What’s this place with no green pin -, Navarre?” They explained it is Eglin AFB where we don’t have a contractor nearby. I thought to myself that’s close to Pensacola.” After a few moments, I thought here goes nothing — “I’ll go!” He replied “are you
serious?” I explained, “I have a lot of family in Pensacola, activate my contract today, I’ll fly direct to the Pensacola Airport and start the contract tomorrow morning.” He signed the agreement without hesitating and I was on my way. That was 23 years ago. One of my greatest decisions.

What is your Profession?

I started a Helicopter company soon after leaving the Army. My passion has always been flying. I (along with my employees) created “Heliworks,” a helicopter transportation company servicing the offshore oil industry, several government agencies, and the US. Army and Navy training centers. After selling Heliworks to a major government defense contractor I figured out that retirement isn’t for me! I now serve as the Principal and Managing Director of S2 Investments, a holding company for Waterview Management Group, responsible for Executive Business Operations both national and international working with the FAA and DoD.

What are some of your favorite things about Pensacola?

People from all over come to Pensacola for a vacation or business trip and fall in love with our city and what it has to offer. Of those, many become new friends, new neighbors and new business associates. It happened to me!

Three words that best describe you.

Driven. Innovative. Grounded.

Finish this statement, I AM PENSACOLA because…

I love the little town big city vibe. Pensacola has become our family.


Jenna Murphy.

WSET Level 3