This week I have a very special guest years in the making. Like another favorite episode, with anonymous guest Modest Proposal, this conversation is with one of the stars of the financial twitter universe who writes anonymously and goes by the pseudonym Jesse Livermore. I met Jesse 6 years ago after reading his unbelievably unique investing research, which tackled all the big and interesting issues in markets. He now also works with me as a research partner at OSAM, where’s he’s used our data to continue to his search for truth in markets. Despite being one of the brightest minds I’ve encountered he is also as humble and unassuming as they come. I’m at least a slightly better person because of trying to emulate how he conducts himself. I get to have many conversations with him that go from 0-100 fast, and I’m thrilled to be able to share one of those with you.

Show Notes

1:33 – (First Question) – Jesse’s origin story for investing

4:37 – Exploring his ways of problem solving starting with intuitive

7:53 – David Epstein Podcast Episode

11:46 – Looking at the analytical way of problem solving

15:42 – Statistical inference

24:45 – Should we opt for simplicity in the investment process

25:26 – Does his own investing include all three, intuition, analysis, and statistics

26:09 – The evolution of his research, process, and thinking on various investment factors.

31:38 – Thoughts on inflation and its impact on market valuation

40:05 – The Earnings Mirage

46:25 – Free Cash flow and valuations

50:51 – What should investors take away from this research

53:01 – Thoughts on trend as an interesting market signal

59:00 – The problems with trend

1:00:34 – Post on “The Single Greatest Predictor of Future Stock Market Returns”

1:11:15 – His work into understanding factors

1:15:36 – Looking at momentum

1:18:16 – His curiosity into the current market cycle

1:20:04 – Lessons learned from his time in the military, an effective way to create an environment where people can safely disagree with their co-workers

1:30:10 – The concept of progress in meaningful work

1:33:08 – Kindest thing anyone has done for him