Episode 44: Money Never Sleeps

In this fourth part of four episodes on movies about trading, Rob Booker and Jason Pyles focus their discussion around the trading movie of all trading movies, Oliver Stone’s 1987 classic, “Wall Street.”

With this backdrop, Rob and Jason talk about the temptations and pitfalls of insider trading, the meaning behind “greed is good,” how you know if you’ve got what it takes to be a trader, what sacrifices being the best at trading for a living will require, the price of making a million dollars and why it’s not difficult to make money (if you’re willing).

Jason’s show about how to write songs: The Songwriting Podcast

Jason’s show about horror movies: Horror Movie Podcast

4 comments on Episode 44: Money Never Sleeps

  1. Bruce Mars says:

    After listening to this I am glad I waited until I was older before I started trading. Early thirtys and now late fiftys….cause after I hit 40 and everything made so much sence and the rules of the game were clear…..that is when my thirst…the true zesty dyin of thirst for knowledge and data, kicked in. Trading is a passion.. and when you love something…the money will follow. So….my passion is to make money so the money has to follow…. hahahahhaa What a great life this is…

  2. Chris says:


    Yes, you are very entertaining. But what I hear from you is an underlying excuse for yourself to not have the love of family and success financially. I really like you. But I hear you more speaking for yourself than to others. Most broke people don’t spend time with their families. So it’s not the money–it’s you/it’s us.
    Still a Fan

    1. robbooker says:


      I have the love of my family. I don’t know how or why, but I do. I have the love of people who aren’t even my family. I give an incredible amount of time to my family. I intentionally walk away from financial opportunities all the time in order to focus on family. And yes, at times, I have asked my family to understand as I work for something that comes from somewhere deep inside, and sometimes it involves money, and because I am blessed with some of the most understanding and caring people I could ever hope for, we make it work. Everyone has a choice, is what I am saying. And it is up to each one of us to stop feeling guilty about making them.

      And how dare you talk about what most broke people do or do not do with their families. How pretentious of you to make an assumption like that. How many broke people do you know? Do you know MOST broke people? That is the most ignorant comment I have heard in a year. Maybe even longer than that. It infuriates me to read that. Have you traveled to Africa (I have). Do you know what most broke people there do? I don’t. But I saw a shitload of people spending time with not just their families, but their communities. I have not been to India because it scares the hell of out of me, but one day I might get there and because of you I will try to pay close attention to what broke people spend time doing all day. My guess is that it won’t be posting comments on my blog about what rich people do all day.

      Last of all, I don’t know enough about you to pass judgment on what was running through your mind when you wrote your comment, so let me say one thing and make one request:

      1. I appreciate that you listened critically. And that you took the time to write to the show. I am a fan of yours too, especially for taking the time to write.

      2. What is it that is most important, in your opinion? What motivates you? What is the balance, in your opinion, between great personal accomplishment and achievement – on one side – and the family and spiritual responsibilities on the other?


  3. Chris says:

    Out of genuine respect for you and your other readers, I won’t respond to the dare, or the ignorant comment, except to say that if making that statement makes you feel more noble than me, then fine, we can leave it there. I’m comfortable enough with my own faults, spirituality, love of family, friends, and concern for others–the need for growth in all those areas; to include, of course, my perceived virtues, to feel quite comfortable with my statement about “broke people”.

    I don’t make the assumption as you seem to, that because someone is broke or poor that these conditions automatically grant them the intangible virtues(love, charity, kindness, sacrifice) –I just don’t think it works that way. I seek those daily.

    I’m sure you have traveled more places than I have, and even met more people. But I have experiences–good and bad, and have met a few people in divers situations in my life’s walk. And I have never been able to help someone whom I have felt sorry for.

    The difference in guys like you who are so self righteous and myself, is that when we come upon someone who is severely lacking material things, we both may help–but you pat them on the head, and would never DREAM they could stand where you stand. Me—I know better.


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