The really solid piece of advice I thought, is to surround yourself with a team that all believes in the same path. No matter whether indie or big label or any other way of reaching an audience, you need to all be singing from the same song sheet.
(Once you are rich and famous you can all tear each other apart, but when you start out you should all be moving in the same direction.)
As for Will's band, if I went to a few of their shows I could become a fan (building local buzz). Of course I will never see them as they are not touring any more and I am in FL and they were in TN.
Finally, the other thing I gleaned, is that there is all this technology in the artists hands with the potential for producing professional results and reaching mass audiences, but managers and lawyers are still needed. Even the best product does not sell itself, needs an industry weasel or two to grease the skids.
So build a great team with great music and great players, and then hire a weasel to handle the business. ( I guess not much has really changed)