Best way to start is to modify your money this could be done with 'Cheat Engine' or modifying your files as not all players abide by the rules so your vehicles may be damaged very fast.
Now the next decision you will have is if you want to abide by the rules.
After this decide if you want to be a lone driver or join a convoy. ( I would suggest C.T.L as a great starting convoy to join very welcoming )
Good luck!