I've yet to hear any real insight from him, and I read the DPR postings back when they came out. I've also listened to the 45 interview call he did from prison. In that call he acknowledged the stress he had put on his family (which his mother nearly died from) and that Silk Road may not have been good for Bitcoin (I don't think it was). So I acknowledge the greater maturity he showed in that call, but that maturity came from the self reflection that getting caught and going to prison can bring. He's certainly lived an interesting life and yes, SR was a part of the late early part of Bitcoin's history (but not part of the really interesting pre 2011 period). Karpeles also lived an interesting experience running Mt Gox but I also wouldn't look to him for insight into Bitcoin. Both were just operational players. Few ppl do actually have novel insights into Bitcoin to share. I just don't see why we should expect Ross to have any, when there's no history so far of him sharing any previously (that I'm aware of).