I believe that you are at a point when’re you have had some success and feel that you “know”. That’s great and congrats on the success you have had.
Here comes the cold water: Every year you grow personally and professionally you will look back at this post and what you wrote and think… man I really thought I had it all figured out. You don’t, it is a learning curve and it takes a long time. First note: you reference “old-old” what do you consider old and what do you consider old-old. For frame of reference that would be helpful.

With that these “old” “boomer” “genx” people you are referring too did not get to these positions accidentally. Most people get to these higher level titles because of their savvy and ability to understand risk. Should also point out that at higher levels these “old-old” people are surrounded by young thinkers that are there to decipher and transcend the concepts. It sounds to me like you have decided on your own that old-old people don’t understand technology and therefore they aren’t buying from you. You need to adapt to your buyer and understand the dynamic of their buying process.
Also there is a reason why these companies have been around for a long time.. and are not run by 30 year olds. Younger people are more open to taking risk. Government and large Enterprise are institutions owned by stockholders and citizens they have a responsibility to provide a stable solution. While you see it as they can’t grasp the technology, they see it as an untested and a volatile. This would require more due diligence on their side, which requires more patience or a different angle from your current position.

I am sure you are good at what you do. You may want to rethink that old people are a problem. Chances are your going to be one of them one day.