Just watched the webinar linked to. For me, one of the most interesting points, was the competitive advantage that freemium pricing combined with value based pricing can bring. Profit Well seems to be a case in point - there are a bunch of options for Stripe (et al.) analytics at the moment but it's got to be tough to compete with a fairly full featured freemium offering...
For those who haven't come across it before and have already dockerized there is a nice solution for some of these issues from replicated (http://www.replicated.com).
And since the $100k to charity would be tax deductible, it's really only circa half that for the publicity. But that too is not symmetric - if Sam wins it's more likely he will be able to put the deduction to good use immediately as he will have more gains.
I was just looking at Connect a few days ago and had one issue - the fact that the customer account needed to bear the fees. Very happy to see the option for the platform account to bear the fees. Much simpler for the customer to understand!