It isn't easy, but i wouldn't call it hard. Just a long and tedious process. And you had better be extremely thorough with regulations or find someone who is.
Starting a fresh Certificate, plan on about a year or a bit more to recieve it.
One thing you might consider doing is purchasing a certificate from someone who already has one. While you cant purchase the certificate itself, you can buy the company which holds the certificate, if that makes any sense. Some companys create a seperate entity to register their certificate to, so it may be possible to purchase a company that does nothing put provide a place to register the certificate to. As i read this, it doesnt make much sense, but i hope you can extract some useful info from it.
Depending on a few variables, purchasing a company that is already established may be a quicker road.
If you buy a company you will then inform the FAA that you will be the President. Then request a name change. Next you will want to ask for a recertification to aquire a new cert. # and erase the history of the previous certificate.
All company manuals will have to be reprinted in the new name and reflect the new ops specs issued.
There is a lot of work to do either way you go, but if you have the money to buy a company, you can get there a little faster.
When I was flying charter I was offered a substantial amount of money to do the "process" and obtain a certificate from the owner of two aircraft that were "piggy backing" on our ticket. After speaking to our POI as well as others I ran in the opposite direction and said it was a no-go. It is not difficult by any means, in fact it is rather easy but it can be a very long and time consuming process. There is a company in Denver that will do all the paper work and you the ticket for between $4,000-$6,000. I do not recall the exact fees but it is in somewhere in that range and it would be well worth it considering how much time and effort have to go into this venture.
If you have the time then go for it, just expect to be "buried" in paper work for a decent amount of time. NBAA has a complete 135 packet that will walk you though it step by step from start to finish. I highly suggest getting this from them, it is "priceless".
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if need be, pm me with any "specifics" since I spent quite a bit of of time researching this topic.
To a large extent it depends on what kind of an operation you want to run. There is Single Pilot, Single PIC, Basic Operator and then a full blown 135 operator. Single Pilot is the easiest to get, no company manual or training program required. If you're operating piston equipment it's a lot easier than trying to get turbine equipment going.
Some of the biggest headaches you'll probably run into are the 135 airworthiness conformity inspections on the aircraft. Aircraft maintenance records have to be in picture-perfect shape, and have to stay that way.
The other big thing you'll face on any operation is your Statement of Compliance. You need to go through each and every 135 reg and state how you will comply (if it's applicable).
The process is long, not because it's hard but because you're dealing with the FAA, which by nature, doesn't move very fast at all, especially on initial certification. Be sure to negotiate a Schedule of Events with your Certification Program Manager as a part of the deal. Last time we went through a major change to our operation, we didn't get a Schedule of Events, and it strung the process out to 6 months.
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