His math and sentiment is correct. In real life, if he tells Bob to invest all his investment saving in an index fund with less than 5 years before retirement (all his investment at this point will be 100% allocated to stocks), Ben should lose whatever license he holds.
"Second, he allowed his investments to compound through the decades by never selling out of the market over his 40+ years of investing. He gave himself a really long runway."
I don't think you get my point, but that's OK. Ben's example is wrong because he's suggesting someone to hold 100% equity all the way up to the end, which is wrong in most cases.
"Obviously, this story was for illustrative purposes and I wouldn’t recommend a portfolio consisting of 100% in stocks of a single market in the S&P 500 unless you have an extremely high risk tolerance. Even then a more balanced portfolio in different global markets with a sound rebalancing policy makes much more sense."