Even if we put aside the fact that he looks and talks and gestures like a douche, he has plenty of douchey bullet points to put him very high on the douche point scale.
• He's a financial planner. (+5 DP)
• He's read the WSJ since he was 11 (+10 DP)
• He grew up near old money (+3 DP)
• He's written two financial planning books (+2 DP)
• He hosts a local talk radio show (+11 DP)
• Runs his own website for financial planning, with his headshot—taken a few years ago, it seems—squarely on the front (+5 DP)
• He was on season two of the Apprentice (+30 DP)
• He was fired from season two of the Apprentice (+5 DP)
• His name is Wes Moss (+1 DP)
That's a 72 on the douche point scale. In comparison, Shia LeBouf only scores a 32, and this guy on the left with the collars only hits a 14.