History of WestWind Airlines

How it all began…

WestWind Co-founder, Sean "Crash" Reilly, takes us back to our "roots"…

I'm not sure what year WWAL officially began – my best guess is 1995-96ish.  Hal Groce, Gary Madore and others were flying for an airline called Air America which – back in those days – was in terrible shape.  I joined and was assigned to the SFO hub but never heard from my hub captain.  Communication was non-existent and I really had no idea how the whole virtual airline thing worked.  I received an e-mail from Gary who also was frustrated saying that he and Hal were thinking of starting up their own VA and inquiring if I'd join them.  I said sure and joined as a pilot.  Gary was my hub captain (WA Hub).  Because I was in from the beginning, I had much communication with Gary, Hal and another great guy named Richard Beasley.  I always had ideas, minor complaints, suggestions (in other words, I was a pain in the rear) so Gary elevated me to Hub Captain of WA and then PDX also.  I ran those hubs for a while.

During this time, our web site was in several locations and no two locations looked the same. This annoyed me as I really thought that the web site was a key feature to attracting new pilots.  I took several web related business seminars for my real-world profession and wanted to put to practice what I was learning.  WestWind was the perfect opportunity.Again, open mouth, insert foot.  I wrote a business plan and then got the green light to – from the ground up – take control over the web look/feel/content.  I began work on our existing site after securing server space (gratis) from Vivid.net.  While the original site was still active, I created our existing site.  Then, when finished, we launched the new site to much fanfare/hype.  It quickly became a huge success (thankfully).

I was anointed VP of Marketing and New Biz Development (basically, I was the "hype" guy).  In this role, I got key flight sim mags to look at us and write about us.  I also got us mentioned in AOPA Pilot Magazine.  I established a relationship with key flight sim folks, software vendors and real-world aviation folks.  This lead to quick growth.  Another stroke of luck/genius was acquiring Cielo Cargo Airlines from Bill Schultz – right at the time when VIP Classic Wings was about to hit the shelves.  Hal handled this and actually got to write about the new "WestWind-Cielo Airline" in the manual that came with the software.  This got many, many more perspective pilots to log on and join – really a stroke of luck.  Classic Wings was a big seller.

Our early team had great division of labor.  Hal was the main mind behind the entire operation. He handled plane design and master-minded most of the operational things (aircraft, most of the initial routes and schedules, etc.)  Gary and Richard handled most of the day-to-day operations and interfaced with the pilots.  As we grew, Richard really came to the front of the pack and helped us grow.  Gary resigned due to real-world responsibilities (Canadian Airforce) but was dragged back in during one of our difficult (growing pains) times.  We very rapidly went from fewer than 100 pilots to several hundred and didn't have the infrastructure to deal with this growth.  Once back on track, Gary had to re-resigned.  Gary was a great guy.  Last I heard he was working one of those "secret black boxes" on a carrier based helicopter. To the best of my knowledge, the only two guys – in our group of "founding fathers" – who actually met in person were Hal and I.  He and I get together (even today) when I'm in Atlanta on biz.  As we continued to grow, Richard had to resign due to real-world responsibilities.  He was sorely missed. 

Fortunately, other very talented guys joined the crew – including Gene Popma, Rodney Redwin and many, many others.  Hal and I quickly recognized these guys had what it took to run the show.  Gene and Rodney were great complainers... er... I mean idea people so they quickly got management positions (open mouth, insert foot).  Gene, Rodney and the great crew they assembled helped WestWind through more tough (growth-related) times, got things nailed down, smoothed out rough edges and, in the process, took WestWind to an even higher level.  All of this growth wasn't easy or painless.  There were many differences of opinion and, on more than one occasion, hard feelings between key staff members.  We lost a few very talented guys – some of who went on to start other VAs – some of which are doing well today.  Still, those who hung together bonded (even though we didn't always agree on all things) and continued to grow the airline. One thing was clear... there certainly wasn't a lack of passion from the team of managers!  I dare not even guess how many combined hours we all put into the WestWind effort. Our wives might be able to give you a number, however.  Most of them think we're nuts. This is why we started the WestWind Widows Club.

Ultimately, my real-world career and family responsibilities made it virtually impossible for me to give WWAL the effort I once gave it and felt it deserved.  Hal was feeling the same way.  By then, Gene and his excellent team were running the day-to-day operation and doing a great job. Hal and I discussed things and decided that WestWind was in great hands and, after much soul searching, decided to hang up our virtual wings and turn the keys of our virtual offices over to Gene and his team.  We're delighted that this team has continued to improve on things and, today, WestWind is 700+ (active) pilots strong.  WestWind is in great hands. 

Hal and I continue to monitor and discuss WestWind.  I stay in touch with Gene (who lives nearby).  I still fly WWAL planes and try to keep my hours up.  Hal, I believe, is doing the same.   Hal still owns the our domain name "www.flywestwind.com".  Even though he's not active in management, he still has his hat in the ring to a lesser extent.  Hal and I want to see WWAL continue to grow and thrive.  We're confident it will.


Sean "Crash" Reilly
Ex-EVP Marketing & New Biz Development/Co-Founder
WestWind Airlines

Future Private Pilot (Summer 2000)
AOPA and EAA Member

Click here to read the official press release: "WestWind Founders Pass The Baton".

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