SI26: Is it more profitable to invest longer-term? and Druckenmiller on being greedy

Is it more profitable to be longer-term? When is Trend Following the wrong strategy to use?  Should you ‘ease’ into a trade, or go all in, and how should you adjust position size?  Other talking points include where to trade Single Stock Futures, how to include Options into a Trend Following strategy, as well as recent quotes from Stanley Druckenmiller about being greedy in the markets, and the quotes from Howard Marks on the psychology of the markets.

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Episode TimeStamps:

00:00 – Intro

01:35 – Weekly review of performance

06:15 – Top tweets

29:35 – Question 1: Antonio; How do you determine if your Trend Following model is broken?

45:00 – Question 2: Seth; How does Jerry diversify his single stock portfolio?

47:20 – Question 3: Dave; Could you discuss specific details of your systems?

48:15 – Question 4/5/6: Carlos; How does Jerry trade single stock futures given liquidity? What is your opinion on using alternative data for position sizing/signal generation? What is your opinion on adjusting position sizes using momentum/pyramiding/etc.?

58:20 – Question 7: Walter; What exchange does Jerry use to trade single stock futures/where is the liquidity?

01:03:30 – Question 8: Brian; Do you use options strategies? If so would you discuss your strategies?

01:09:50 – Question 9: Glen; Please discuss your execution process once a system provides a signal.

01:15:00 – Question 10/11: Keith; If establishing a new system, do you put on all positions as of a specific date or sit in cash...