Sorry to hear. Hopefully, there will be something for others to learn from the NTSB reports that came out. I'm just grasping at straws here, but maybe it might have been possible for your friend to have started Private and Instrument in the Mooney, then hung out there for 300 hours or so before stepping up to the TBM for another 300 hours or so, and then to a larger and more complex turboprop twin for the next 2,000-3,000 hours building time in something that prepares him for the Phenom?

I once knew a pilot (a very long time ago) who went from a C-182 Trainer in which he obtained all his basic ratings. He flew that for about 250 hours honing his IFR/IMC skills. From there, he stepped up to a Piper PA-31 Navajo that he flew with AmeriFlight. I was working at AmeriFlight at the time trying to get through school. He flew that PA-31 for 3 years until upgrading to a King Air 100. He put on about 1,000 hours in that until upgrading again to a Lear 35A. I don't know how long he remained with AmeriFlight after that, but I later learned that he was working the right seat of a Boeing 737. He's now a 777 Captain and has a five day work week.

I used to fly with him from KOAK-KBUR-KOAK before the Ks were added. The night departure on Friday, was cool. However, I remember those early morning approaches flying down into Bay Area fog. We'd break out like clockwork underneath and either 27R or 27L was always sitting right there on cue. This was before the heading change to 28R/28L, of course. It was fun flying with him - an experience I'll never forget.