Thinking Outside The Street Podcast – Episode 5 – Dumb Money Vs. Smart Money


In This Episode:  Paul and Cliff discuss the mistakes many investors make by investing emotionally and not rationally.

  • Most investors wait until it is too late to enter the markets and then exit much  later than they should.
  • The emotional and psychological dynamics of investing are probably the hardest to master.
  • One can always find a justification for the mistakes one is making at any given time.
  • Many investors resort to buy and hold or sit-in-cash strategies because they don’t know any other way to invest.
  • The cocktail party tip approach to investing rarely works in the short term and is not a good long term strategy. How many cocktail parties are you planning on attending?


  • John Nofsinger. The Psychology of Investing. A good book about the psychological dynamics that play into the trading of your account.
Source - Stephan Cheplick

Source – Stephan Cheplick

Episode 1 – Thinking Outside The Street – Huh?

What in the World?


In This Episode:

  • Portfolio managers Cliff and Paul Montgomery talk about the ideas behind starting this blog and podcast.
  • Explain what they mean by Unconventional Wisdom.
  • Talk about how much hair Cliff lost in 2008.
  • Reveal that they live on a farm – Really! They are not Wall Street!
  • Talk about upcoming episodes.