This is a deliberate misquote (lie) by Rob....who has no scruples. The quote is "It's not whether you win or lose; it's whether or not you had a good bet."
Unlike Rob and Alan, I have absolutely no problem understanding the meaning of Shack's statement. It is similar to Mike Caro's "Poker is not about winning pots; it's about making correct decisions."
Example 1. If anyone here wants to lay me 11 to 10 flipping coins I will gladly play you until you are broke.
Example 2. If you ask me to lay 11 to 10 flipping coins I will turn you down.
In both cases I will be making the correct decision. But in Example 1, if I'm getting 11 to 10 on each flip I'm going to lose half the flips but I still have a good bet. My position in the game would be so strong that if Bill Gates played me long enough I would take every dime he has. This is what Shack's statement means. If you make correct decisions the winning will take care of itself....even if you don't win every bet.