The first problem is calling ANY show "The Winner". It like calling a show "The New Hit Show". Its just begging to go down in flames.
The real problem is the plot. Someone else said it best "He's a 32 yr-old loser living with his parents... that's all you need to know. " That about sums it up, though the shows problems go much deeper than that. After all this guy is clearly a LOSER, not a WINNER, despite its alleged premise the guy eventually becomes a winner which is silly. The next episode "Glens New Friend" is the obligatory gay themed episode. The awful "Knights of Prosperity" tried this gay thing too and rating crashed, though there were 100 other reason why it died. A show like "Wil and Grace", though gay themed, succeeded because it was part of the premise. In shows where it isnt, it just doesnt work. This episode may be the one that torpedoes it for good.
Some critics have compared this to "Ed". What are those guys smoking. I wasnt a huge fan of Ed, but this show in now way compares to that one. I at least understood why people like Ed. This one? No idea. No wait, I guess the target demographic is 32 year old guys living in their parents basement dreaming they will one day be rich and successful. Thats a pretty small demo. They would get more laughs watching the movie "The 40 Year Old Virgin".